Quarterlytics / Financial Services / Insurance - Specialty / Tiptree Inc. / FY2023 Annual Report

Tiptree Inc.
Annual Report 2023

TIPT · NASDAQ Financial Services
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Ticker TIPT
Exchange NASDAQ
Sector Financial Services
Industry Insurance - Specialty
Employees 1496
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FY2023 Annual Report · Tiptree Inc.
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2023 

1 

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
Annual percentage change in share price of Tiptree Inc. vs. equity indices as of 12/31/23*: 

1 Year 
3 Year 
5 Year 
10 Year 
From Inception (June 2007) 

*Including dividends 

To	Our	Fellow	Shareholders: 

Tiptree	
38.4%	
58.5%	
29.8%	
11.1%	
10.6%	

Russell 2000 
16.9% 
2.2% 
10.0% 
7.2% 
7.1% 

S&P 500 
26.3% 
10.0% 
15.7% 
12.0% 
9.4% 

2023 was a year of strong performance for Tiptree. Our businesses continued to build upon their 
history of growth and profitability, producing an 18% increase in revenues to $1.6 billion for the year, 
and an adjusted return on equity of 15.2%. Tiptree’s share price appreciation and dividends produced a 
total return of 38.4% for the year, compared to 16.9% for the Russell 2000 and 26.3% for the S&P 500. 
We are proud of our 2023 results, yet we keep a greater focus on long-term performance, and like to 
compare our results to other investment strategies. With this in mind, Tiptree’s performance over 
three, five, and ten years (and since inception) are worth noting in the chart above. We are also pleased 
to have increased our quarterly dividend by 20% to $0.06 per share, payable to shareholders of record 
as of March 11, 2024. 

The	Fortegra	Group, our specialty insurance business under the leadership of CEO Rick Kahlbaugh, 
achieved record results for the year, with premium and premium equivalent growth of 21%, and an 
adjusted return on equity of 29%. Although the recent market environment was unconducive for a public 
offering, we firmly believe Fortegra is strategically positioned to maintain a trajectory of consistent top-
line growth and sustained underwriting profitability over the long-term.  

Tiptree	Capital, our subsidiary through which we invest opportunistically in a broad range of assets and 
businesses, finished the year with a book value of $178 million consisting primarily of 1) cash, 2) our 
mortgage origination and servicing business, Reliance First Capital, and 3) a liquid investment portfolio. 
At Reliance, led by CEO Hugh Miller, origination volumes remained muted given the interest rate 
environment, although the income and sustained market value of our retained servicing book allowed the 
business to remain stable for the year; this performance contrasts significantly with the havoc taking 
place in the mortgage industry writ large. Given Reliance’s proven nimbleness, we maintain a positive 
outlook for the business. We see greater potential for future profit as mortgage rates stabilize, in addition 
to the increased potential of finding bolt-on acquisitions.  

We are always looking for new investment opportunities, with the objective of generating attractive “all-
weather”, absolute returns. Having no set holding period and no risk of redemption of our capital gives us 
a distinct advantage, as we are able to take a long-term view on our outlook for returns.	

1 

 
 
	
 
 
 
 
Looking ahead, we see significant opportunities to expand our businesses and remain confident in the 
long-term outlook for the company. 2023 was a year of strong performance, with our businesses 
continuing their history of growth and profitability. Once again, we credit these results to the 
experience and expertise of Tiptree’s team of professionals and those of our related companies. We 
begin 2024 well positioned financially, and we could not be more excited about Tiptree’s future. 

We welcome any and all questions from our shareholders and look forward to speaking with you. 

With best regards,  

Michael Barnes 
Executive Chairman 

Jonathan Ilany  
Chief Executive Officer 

2 

 
 
 
UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549
FORM 10-K

(Mark One)

☒

☐

Annual Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934

For the fiscal year ended December 31, 2023
OR

Transition Report Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934

For the transition period from            to            
Commission File Number: 001-33549
Tiptree Inc. 
(Exact name of Registrant as Specified in Its Charter)   

Maryland

38-3754322

(State or Other Jurisdiction of Incorporation)

(I.R.S. Employer Identification No.)

660 Steamboat Road, 2nd Floor, Greenwich, Connecticut  
(Address of Principal Executive Offices)

06830
(Zip Code)

(Registrant’s telephone number, including area code) (212) 446-1400 

Securities registered pursuant to Section 12(b) of the Act:

 Title of each class
common stock, par value $0.001 per share

Trading Symbol(s) Name of each exchange on which registered

TIPT

NASDAQ Capital Market

Securities Registered Pursuant to Section 12(g) of the Act: None

Indicate by check mark if the registrant is a well-known seasoned issuer, as defined in Rule 405 of the Securities Act. Yes ¨	No x

Indicate by check mark if the registrant is not required to file reports pursuant to Section 13 or Section 15(d) of the Act. Yes ¨	No x

Indicate by check mark whether the registrant: (1) has filed all reports required to be filed by Section 13 or 15(d) of the Securities Exchange Act of 1934 during the 
preceding 12 months (or for such shorter period that the registrant was required to file such reports), and (2) has been subject to such filing requirements for the past 
90 days.     Yes  x		No ¨

Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T 
(§232.405 of this chapter) during the preceding 12 months (or for such shorter period that the registrant was required to submit such files).   Yes x     No  	¨

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or emerging growth 
company.  See  the  definitions  of  “large  accelerated  filer,”  “accelerated  filer,”  “smaller  reporting  company,”  and  “emerging  growth  company”  in  Rule  12b-2  of  the 
Exchange Act.

Large accelerated filer  ¨	
Non-accelerated filer    ¨	

Accelerated filer  x
Smaller reporting company ☐
Emerging growth company ☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised 
financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ¨
Indicate  by  check  mark  whether  the  registrant  has  filed  a  report  on  and  attestation  to  its  management’s  assessment  of  the  effectiveness  of  its  internal  control  over 
financial reporting under Section 404(b) of the Sarbanes-Oxley Act (15 U.S.C. 762(b)) by the registered public accounting firm that prepared or issued its audit report. 
☒

If securities are registered pursuant to Section 12(b) of the Act, indicate by check mark whether the financial statements of the registrant included in the filing reflect the 
correction of an error to previously issued financial statements.  ¨

Indicate by check mark whether any of those error corrections are restatements that required a recovery analysis of incentive-based compensation received by any of the 
registrant’s executive officers during the relevant recovery period pursuant to §240.10D-1(b).   ¨
Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Exchange Act.)   Yes ☐     No ☒ 

As of June 30, 2023, the last business day of the registrant’s most recently completed second fiscal quarter, the aggregate market value of the registrant’s voting and 
non-voting common equity held by non-affiliates of the registrant was approximately $368,186,354, based upon the closing sales price of $15.01 per share as reported 
on the Nasdaq Capital Market. For purposes of this calculation, all of the registrant’s directors and executive officers were deemed to be affiliates of the registrant.

As of February 20, 2024, there were 36,761,206 shares, par value $0.001, of the registrant’s common stock outstanding.

Documents Incorporated by Reference

  
 
 
 
 
	
	
	
	
	
	
	
	
 
 
 
 
 
 
 
Certain  information  in  the  registrant’s  definitive  proxy  statement  to  be  filed  with  the  Securities  and  Exchange  Commission  relating  to  the  registrant’s 2024  Annual 
Meeting of Stockholders is incorporated by reference into Part III.    

TIPTREE INC.
Annual Report on Form 10-K
December 31, 2023
Table of Contents

ITEM
PART I 
Item 1. Business
Item 1A. Risk Factors
Item 1B. Unresolved Staff Comments
Item 1C. Cybersecurity
Item 2. Properties
Item 3. Legal Proceedings
Item 4. Mine Safety Disclosures
PART II
Item 5. Market for Registrant’s Common Equity, Related Stockholder Matters and Issuer Purchases of Equity Securities
Item 6. Reserved.
Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations
Item 7A. Quantitative and Qualitative Disclosures About Market Risk
Item 8. Financial Statements and Supplementary Data

Report of Independent Registered Public Accounting Firm
Consolidated Balance Sheets for December 31, 2023 and 2022
Consolidated Statements of Operations for the three years ended December 31, 2023, 2022, and 2021
Consolidated Statements of Comprehensive Income (Loss) for the three years ended December 31, 2023, 2022, and 2021
Consolidated Statement of Changes in Stockholders’ Equity for the three years ended December 31, 2023, 2022, and 2021
Consolidated Statements of Cash Flows for the three years ended December 31, 2023, 2022, and 2021
Notes to Consolidated Financial Statements

(1) Organization
(2) Summary of Significant Accounting Policies
(3) Acquisitions
(4) Dispositions and Assets and Liabilities Held for Sale
(5) Operating Segment Data
(6) Investments
(7) Notes and Accounts Receivable, net
(8) Reinsurance Receivables
(9) Goodwill and Intangible Assets, net
(10) Derivative Financial Instruments and Hedging
(11) Debt, net
(12) Fair Value of Financial Instruments
(13) Liability for Unpaid Claims and Claim Adjustment Expenses
(14) Revenue from Contracts with Customers
(15) Other Assets and Other Liabilities and Accrued Expenses
(16) Other Revenue and Other Expenses
(17) Stockholders’ Equity
(18) Accumulated Other Comprehensive Income (Loss)
(19) Stock Based Compensation
(20) Income Taxes
(21) Commitments and Contingencies
(22) Earnings Per Share
(23) Related Party Transactions
(24) Subsequent Events

Item 9. Changes in and Disagreements with Accountants on Accounting and Financial Disclosure
Item 9A. Controls and Procedures
Item 9B. Other Information
Item 9C. Disclosure Regarding Foreign Jurisdictions that Prevent Inspections.
PART III
Item 10. Directors, Executive Officers and Corporate Governance
Item 11. Executive Compensation

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TIPTREE INC.
Annual Report on Form 10-K
December 31, 2023
Table of Contents

ITEM
Item 12. Security Ownership of Certain Beneficial Owners and Management and Related Stockholder Matters
Item 13. Certain Relationships and Related Transactions, and Director Independence
Item 14. Principal Accountant Fees and Services
PART IV
Item 15. Exhibits, Financial Statement Schedules
Item 16. Form 10-K Summary
Signatures

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PART I

Forward-Looking Statements 

Except for the historical information included and incorporated by reference in this Annual Report on Form 10-K, the information 
included  and  incorporated  by  reference  herein  are  “forward-looking  statements”  within  the  meaning  of  Section  27A  of  the 
Securities Act and Section 21E of the Exchange Act. Forward-looking statements provide our current expectations or forecasts of 
future  events  and  are  not  statements  of  historical  fact.  These  forward-looking  statements  include  information  about  possible  or 
assumed  future  events,  including,  among  other  things,  discussion  and  analysis  of  our  future  financial  condition,  results  of 
operations  and  our  strategic  plans  and  objectives.  When  we  use  words  such  as  “anticipate,”  “believe,”  “estimate,”  “expect,” 
“intend,”  “seek,”  “may,”  “might,”  “plan,”  “project,”  “should,”  “target,”  “will,”  or  similar  expressions,  we  intend  to  identify 
forward-looking statements. 

Forward-looking statements are not guarantees of future performance and are subject to risks, uncertainties and other factors, many 
of which are beyond our control, are difficult to predict and could cause actual results to differ materially from those expressed or 
forecasted  in  the  forward-looking  statements.  Our  actual  results  could  differ  materially  from  those  anticipated  in  these  forward-
looking statements as a result of various factors, including, but not limited to, those described in the section entitled “Risk Factors” 
and elsewhere in this Annual Report on Form 10-K and in our other public filings with the SEC. 

The factors described herein are not necessarily all of the important factors that could cause actual results or developments to differ 
materially  from  those  expressed  in  any  of  our  forward-looking  statements.  Other  unknown  or  unpredictable  factors  also  could 
affect  our  forward-looking  statements.  Consequently,  our  actual  performance  could  be  materially  different  from  the  results 
described  or  anticipated  by  our  forward-looking  statements.  Given  these  uncertainties,  you  should  not  place  undue  reliance  on 
these  forward-looking  statements.  Except  as  required  by  the  applicable  law,  we  undertake  no  obligation  to  update  any  forward-
looking statements.

Market and Industry Data

This Annual Report on Form 10-K includes certain market and industry data and statistics, which are based on publicly available 
information,  industry  publications  and  surveys,  reports  by  market  research  firms  and  our  own  estimates  based  on  our 
management’s  knowledge  of,  and  experience  in,  the  insurance  industry  and  market  segments  in  which  we  compete.  Third-party 
industry publications and forecasts generally state that the information contained therein has been obtained from sources generally 
believed  to  be  reliable.  In  addition,  certain  information  contained  in  this  Form  10-K,  including  information  relating  to  the 
proportion  of  new  opportunities  we  pursue,  represents  management  estimates.  While  we  believe  our  internal  estimates  to  be 
reasonable, they have not been verified by any independent sources. Such data involve risks and uncertainties and are subject to 
change  based  on  various  factors,  including  those  discussed  under  the  captions  “Risk  Factors,”  “Cautionary  Note  Regarding 
Forward-Looking Statements and Information” and “Management’s Discussion and Analysis of Financial Condition and Results of 
Operations.”

5

 
Summary Risk Factors

Our business is subject to a number of risks, including risks that may prevent us from achieving our business objectives or may 
adversely affect our business, financial condition, results of operations, cash flows and prospects. These risks are discussed more 
fully in Item 1A. Risk Factors herein. These risks include, but are not limited to, the following:

•

•

A portion of our assets are illiquid or have limited liquidity, which may limit our ability to sell those assets at favorable 
prices or at all and creates uncertainty in connection with valuing such assets.

Our investment in Invesque shares is subject to market volatility.

• We operate in highly competitive markets for business opportunities and personnel, which could impede our growth and 

negatively impact our results of operations.

•

•

•

•

The  amount  of  statutory  capital  and  reserve  requirements  applicable  to  our  insurance  subsidiaries  can  increase  due  to 
factors outside of our control.

Our insurance subsidiaries’ actual claims losses may exceed their reserves for claims, which may require them to establish 
additional reserves.

Performance of our insurance subsidiaries’ investment portfolio is subject to a variety of investment risks.

Our insurance subsidiaries could be forced to sell investments to meet their liquidity requirements.

• We  may  need  to  raise  additional  capital  in  the  future  or  may  need  to  refinance  existing  indebtedness,  but  there  is  no 

assurance that such capital will be available on a timely basis, on acceptable terms or at all.

•

•

•

•

•

•

•

•

•

•

•

•

•

•

•
•
•

•

Cybersecurity attacks or information system failures could disrupt our businesses, including our insurance businesses. 

Third-party vendors our insurance subsidiaries rely upon to provide certain business and administrative services on their 
behalf  may  not  perform  as  anticipated.  These  include  independent  financial  institutions,  lenders,  distribution  partners, 
agents, brokers and retailers for distribution of its products and services, and the loss of these distribution sources, or their 
failure to sell our insurance business’s products and services could be adverse.

A  downgrade  in  our  insurance  subsidiaries’  claims  paying  ability  or  financial  strength  ratings  could  increase  policy 
surrenders and withdrawals, adversely affecting relationships with distributors and reducing new policy sales.

If  market  conditions  cause  reinsurance  to  be  more  costly  or  unavailable,  our  insurance  subsidiaries  may  be  required  to 
bear increased risks or reduce the level of their underwriting commitments.

Our  insurance  subsidiaries  may  incur  losses  if  reinsurers  are  unwilling  or  unable  to  meet  their  obligations  under 
reinsurance contracts.

New lines of business, new products and services or new geographic markets may subject our insurance subsidiaries to 
additional risks.

The effects of emerging claim and coverage issues on our insurance subsidiaries’ business are uncertain.

Our  insurance  subsidiaries’  international  operations  expose  them  to  investment,  political  and  economic  risks,  including 
foreign currency and credit risk.

Our insurance subsidiaries’ continued growth depends partly on the continued growth of their business’s customer base.

Our results of operations have in the past varied quarterly and may not be indicative of our long-term prospects.

Adverse  economic  factors,  including  recession,  inflation,  periods  of  high  unemployment  or  lower  economic  activity, 
could result in the sale of fewer policies than expected or an increase in the frequency of claims and premium defaults, 
and  even  the  falsification  of  claims,  or  a  combination  of  these  effects,  which,  in  turn,  could  affect  our  insurance 
subsidiaries’ growth and profitability.

Our  business’s  risk  management  policies  and  procedures  may  prove  to  be  ineffective  and  leave  them  exposed  to 
unidentified or unanticipated risk.

Our  insurance  subsidiaries  may  not  be  able  to  generate  sufficient  cash  to  service  all  of  their  indebtedness  and  may  be 
forced to take other actions to satisfy their obligations under their indebtedness, which may not be successful.

Restrictive  covenants  in  the  agreements  governing  our  insurance  subsidiaries’  indebtedness  may  restrict  their  ability  to 
pursue their business strategies.
Retentions in various lines of business and catastrophic events expose our insurance subsidiaries to potential losses.
The exit of the United Kingdom from the European Union could adversely affect our insurance subsidiaries’ business.
Due to the structure of some of our insurance business’s commissions, it is exposed to risks related to the creditworthiness 
of some of its independent agents and program partners.
Our insurance subsidiaries may act based on inaccurate or incomplete information regarding the accounts they underwrite.

6

•

•

•

•

•

•

The insurance industry is cyclical in nature, competition is intense and our insurance business may lose clients or business 
as a result of consolidation within the financial services industry or otherwise.

Any failure to establish, maintain, protect or enforce our insurance subsidiaries’ intellectual property rights could impair 
their  intellectual  property,  technology  platform  and  brand.  In  addition,  they  may  be  sued  for  alleged  infringement, 
misappropriation or other violation of their proprietary rights.

Our businesses employ third-party licensed software, and the inability to maintain these licenses, errors in the software 
they license or the terms of open source licenses could result in increased costs or reduced service levels, which would 
adversely affect their business.

Some of our investments are made jointly with other persons or entities, which may limit our flexibility with respect to 
such jointly owned investments.

Our mortgage business is significantly impacted by interest rates. Changes in prevailing interest rates or U.S. monetary 
policies that affect interest rates may have a detrimental effect on our mortgage business. 

Our mortgage business is highly dependent upon programs administered by GSEs to generate revenues through mortgage 
loan  sales  to  institutional  investors.  Any  changes  in  existing  U.S.  government-sponsored  mortgage  programs  could 
materially and adversely affect our mortgage business, financial condition and results of operations.

• We may be unable to obtain sufficient capital to meet the financing requirements of our mortgage business.

•

In our mortgage business, we may sustain losses and/or be required to indemnify or repurchase loans we originated, or 
will originate, if, among other things, our loans fail to meet certain criteria or characteristics. 

• We may be limited in the future in utilizing net operating losses incurred during prior periods to offset taxable income.

• We  may  leverage  certain  of  our  assets  and  a  decline  in  the  fair  value  of  such  assets  may  adversely  affect  our  financial 

condition and results of operations.

•

•

•

•

•

•

Certain of our and our subsidiaries’ assets are subject to credit risk, market risk, interest rate risk, credit spread risk, call 
and redemption risk and refinancing risk, and any one of these risks may materially and adversely affect the value of our 
assets, our results of operations and our financial condition.

Our risk mitigation or hedging strategies could result in our experiencing significant losses.

The values we record for certain investments and liabilities are based on estimates of fair value made by our management, 
which may cause our operating results to fluctuate and may not be indicative of the value we can realize on a sale.

The accounting rules applicable to certain of our transactions are highly complex and require the application of significant 
judgment and assumptions by our management. In addition, changes in accounting interpretations or assumptions could 
impact our financial statements.

Because we are a holding company, our ability to meet our obligations and pay dividends to stockholders will depend on 
distributions from our subsidiaries that may be subject to restrictions and income from assets.

Some  provisions  of  our  charter  may  delay,  deter  or  prevent  takeovers  and  business  combinations  that  stockholders 
consider in their best interests.

• Maryland takeover statutes may prevent a change of our control, which could depress our stock price.

•

Our holding company structure with multiple lines of business, may adversely impact the market price of our common 
stock and our ability to raise equity and debt capital.

• Maintenance of our 1940 Act exemption imposes limits on our operations.

•

•

•

•

Increasing regulatory focus on privacy issues and expanding laws could affect our various subsidiaries’ business models 
and expose them to increased liability.

Our insurance subsidiaries could be adversely affected if their controls to ensure compliance with guidelines, policies and 
legal and regulatory standards are not effective.

Our businesses are subject to risks related to litigation and regulatory actions, including increased compliance costs.

Our  international  activities  increase  the  compliance  risks  associated  with  economic  and  trade  sanctions  imposed  by  the 
United States, the EU and other jurisdictions.

• We could be materially adversely affected by violations of the U.S. Foreign Corrupt Practices Act, the U.K. Bribery Act 

•

•

and anti-corruption laws in other applicable jurisdictions.
Assessments  and  premium  surcharges  for  state  guaranty  funds,  secondary-injury  funds,  residual  market  programs  and 
other mandatory pooling arrangements may reduce our insurance subsidiaries’ profitability. 
Operation  of  dry  bulk  vessels  and  product  tankers  is  subject  to  complex  laws  and  regulations,  including  environmental 
laws and regulations that, if any of our vessel owner subsidiaries are found guilty of violation, can result in substantial 
fines and costs to the Company.

7

Note to Reader

In reading this Annual Report on Form 10-K, references to: 

“1940 Act” means the Investment Company Act of 1940, as amended. 
“A.M. Best” means A.M. Best Company, Inc. 
“BSBY” means the Bloomberg Short-Term Bank Yield Index.
“CAGR” means compound annual growth rate.
“CFPB” means the Consumer Financial Protection Bureau. 
“Code” means the Internal Revenue Code of 1986, as amended.
“Common Stock” or “Common Shares” means Tiptree’s common stock $0.001 par value per share.
“Corvid Peak” means collectively: Corvid Peak Holdings, L.P., Corvid Peak Capital Management, LLC, Corvid Peak GP 
Holdings, LLC and Corvid Peak Holdings GP, LLC.
“Corvid Peak Funds” means Corvid Peak Restructuring Partners Onshore Fund LLC and Albatross CP LLC.
“Defend” means Defend Insurance Group. 
“Dodd-Frank Act” means the Dodd-Frank Wall Street Reform and Consumer Protection Act. 
“E&S” means excess and surplus. 
“EBITDA” means earnings before interest, taxes, depreciation and amortization. 
“EBITDAR” means earnings before interest, taxes, depreciation and amortization, and restructuring or rent costs. 
“EU” means European Union. 
“Exchange Act” means the Securities Exchange Act of 1934, as amended.
“Fannie Mae” means Federal National Mortgage Association.
“Fortegra” or “The Fortegra Group” means The Fortegra Group, LLC and its subsidiaries prior to June 21, 2022 and The Fortegra 
Group, Inc. on or after June 21, 2022.
“Fortegra Additional Warrants” means the additional warrants issued to Warburg and Tiptree Holdings to acquire Fortegra 
Common Stock.
“Fortegra Additional Warrants (Warburg)” means the Fortegra Additional Warrants issued to Warburg.
“Fortegra Common Stock” means the common stock of Fortegra.
“Fortegra Financial” means Fortegra Financial Corporation.
“Fortegra Plan” means the 2022 Equity Incentive Plan of Fortegra.
“Fortegra Preferred Stock” means the 5,333,333 shares of Series A Preferred Stock of Fortegra issued to Warburg.
“Fortegra Warrants” means the warrants to purchase shares of Fortegra Common Stock. 
“Fortegra Warranty” mean Fortegra Warranty Holdings, LLC.
“Fortress” means Fortress Credit Corp., as administrative agent, collateral agent and lead arranger, and affiliates of Fortress that are 
lenders under the Credit Agreement among the Company, Fortress and the lenders party thereto.
“Freddie Mac” means Federal Home Loan Mortgage Corporation.
“GAAP” means U.S. generally accepted accounting principles. 
“Ginnie Mae” means Government National Mortgage Association.
“GSE” means government-sponsored enterprise.
“GWPPE” means gross written premium and premium equivalents.
“Invesque” means Invesque Inc.
“ITC” means ITC Compliance GRP Limited.
“Luxury” means Luxury Mortgage Corp.
“MGAs” means managing general agents. 
“NAIC” means the National Association of Insurance Commissioners.
“Operating Company” means Tiptree Operating Company, LLC.
“Premia” means Premia Solutions Limited. 
“Reliance” means Reliance First Capital, LLC. 
“ROAE” means return on average equity.
“SEC” means the U.S. Securities and Exchange Commission. 
“Securities Act” means the Securities Act of 1933, as amended.
“Sky Auto” means Sky Services LLC.
“Smart AutoCare” means the following entities and their subsidiaries operating under the Smart AutoCare brand: SAC Holdings, 
Inc., Freedom Insurance Company, Ltd., Dealer Motor Services, Inc., Independent Dealer Group, Inc., Ownershield, Inc. and 
Accelerated Service Enterprise, LLC.
“SOFR” means the Secured Overnight Financing Rate.
“Tiptree”, the “Company”, “we”, “its”, “us” and “our” means, unless otherwise indicated by the context, Tiptree Inc. and its 
consolidated subsidiaries.
“Tiptree Holdings” means Tiptree Holdings LLC.

8

“Transition Services Agreement” means the Amended and Restated Transition Services Agreement between Corvid Peak and 
Tiptree Inc., effective as of January 1, 2019.
“VSC” means vehicle service contracts.
“Warburg” means WP Falcon Aggregator, L.P., a Delaware limited partnership affiliated with funds advised or managed by 
Warburg Pincus LLC.
“WP Transaction” means the $200 million strategic investment in Fortegra by Warburg.

9

Item 1. Business

OVERVIEW

Our Business

At  Tiptree,  our  mission  is  to  build  long-term  value  by  allocating  capital  to  select  small  and  middle  market  companies  across 
industries. We have a significant track record investing in the insurance and credit-related financial sectors. With proprietary access 
and a flexible capital base, we seek to uncover compelling investment opportunities and support management teams in unlocking 
the full value potential of their businesses. This investment philosophy, executed by our experienced leadership, is our hallmark 
and has delivered consistent risk-adjusted returns to our stockholders since 2007.

We categorize our businesses into: Insurance and Tiptree Capital. 

Insurance:  Our  Insurance  segment  consists  of  Fortegra,  which  is  a  growing,  consistently  profitable,  and  multinational  specialty 
insurance company focused on underwriting complex and niche risks in underserved markets. Founded in 1978, the business has a 
long-standing track record of disciplined and stable underwriting results while generating strong growth and attractive returns on 
capital. Fortegra is an underwriting-focused company, with deep expertise within the admitted and E&S insurance lines and capital 
light fee-based services markets. It targets moderate risk limits and utilizes a sophisticated reinsurance strategy to reduce volatility 
and  protect  its  capital.  The  business  differentiates  itself  through  its  go-to-market  strategy,  expertise  in  customized  underwriting 
solutions and the value-added services offered to its distribution partners.

Tiptree  Capital:  We  own  a  diversified  group  of  businesses  and  investments  that  are  owned  and  managed  separately  as  Tiptree 
Capital,  which  include  our  Mortgage  segment  operations.  We  manage  Tiptree  Capital  with  a  long-term  focus,  balancing  current 
cash  flow  and  long-term  value  appreciation.  Today,  Tiptree  Capital  consists  primarily  of  our  mortgage  operations  and  principal 
investments.

Our Operating Principles

We acquire controlling interests and invest in businesses that we believe (i) operate in industries with long-term macroeconomic 
growth opportunities, (ii) have positive and stable cash flows, (iii) offer scalable business models with embedded optionality, and 
(iv) have strong management teams. We believe that our patient capital approach and long-term outlook enhances the ability for 
our businesses to grow earnings and cash flows across market cycles. 

Underwrite to a Profit. Our principal strategic objective is to continue expanding Fortegra’s operations, particularly the specialty 
insurance and service contract businesses. Our highest priority is to maintain strong underwriting practices, with attention paid to 
the insurance disciplines of pricing, underwriting and claims management.

Invest for Long-term Returns. Our financial goals are to generate consistent and growing earnings and cash flow, and to enhance 
stockholder  value  as  measured  by  growth  in  stock  price  plus  dividends  paid.  We  manage  Tiptree  with  a  long-term  perspective, 
balancing cash-flowing investments with opportunities for capital appreciation. We focus on targeting investment returns that have 
a  combination  of  current  earnings  and  long-term  capital  appreciation,  understanding  that  temporary  accounting  gains  and  losses 
may vary significantly from one period to the next.

Think Like Owners. Efficient deployment of capital is our top priority. We aim to find the best use of capital to create long-term 
value  for  our  stockholders.  We  hope  to  achieve  this  through  a  combination  of  investments  in  our  existing  businesses,  select 
acquisitions and monetization opportunities, opportunistic share repurchases and paying a consistent dividend. As of December 31, 
2023, directors, officers, employees and related trusts owned 33% of the Company. 

As  of  December  31,  2023,  Tiptree  and  its  consolidated  subsidiaries  had  1,504  employees,  21  of  whom  were  at  our  corporate 
headquarters.  Corporate  employees  are  responsible  for  overall  strategy,  capital  allocation  and  investment  decisions,  as  well  as 
public company reporting and compliance.

Our businesses are subject to regulation as described below. The 1940 Act may limit the types and nature of businesses that we 
engage in and assets that we may acquire. See “Risk Factors-Risks Related to Regulatory and Legal Matters-Maintenance of our 
1940 Act exemption will impose limits on our operations.”

Insurance

Fortegra  is  a  growing,  consistently  profitable,  and  multinational  specialty  insurance  company  focused  on  underwriting  complex 
and niche risks in underserved markets. Founded in 1978, the business has a long-standing track record of disciplined and stable 
underwriting results while generating strong growth and attractive returns on capital. Fortegra is an underwriting-focused company, 

10

with deep expertise within the admitted and E&S insurance lines and capital light fee-based services markets. It targets moderate 
risk limits and utilizes a sophisticated reinsurance strategy to reduce volatility and protect its capital. The business differentiates 
itself through its go-to-market strategy, expertise in customized underwriting solutions and the value-added services offered to its 
distribution partners. Fortegra’s financial success is demonstrated through its GWPPE CAGR of 26%, average combined ratio of 
91%, average ROAE of 15% and average adjusted ROAE of 21%, each measured since January 1, 2019 through December 31, 
2023. 

Fortegra’s  balanced  business  mix  allows  it  to  opportunistically  allocate  capital  as  market  conditions  change  and  utilize  the  cash 
flows  generated  through  capital  light,  fee-based  businesses  to  partially  fund  the  growth  capital  required  across  its  insurance 
businesses.  Fortegra  has  proven  its  ability  to  opportunistically  take  advantage  of  market  dynamics  throughout  its  history,  and 
remains well positioned to benefit from an increasingly complex world, leading to secular growth in the specialty P&C market.

Fortegra  underwrites  specialty  programs  which  are  distributed  primarily  through  MGAs,  retail  agents  and  other  distributors, 
collectively referred to as distribution partners. We believe this agent-centric specialty focus provides Fortegra with a competitive 
advantage and enables them to provide distribution partners with value-added services to improve their underwriting and operating 
performance,  driving  high  agent  retention.  We  believe  this  “one-to-many”  distribution  model  is  more  efficient  for  the  types  of 
specialty risks Fortegra underwrites and allows the business to leverage its agents’ specialization in a particular market as well as 
their  extensive  retail  network.  To  align  economic  interests,  distribution  partners  receive  variable  forms  of  commission  based  on 
underwriting performance which supports the consistency and stability of Fortegra’s underwriting results. We believe this agent-
centric  distribution  model  is  positioned  for  success  given  the  continued  growth  of  MGAs  as  a  distribution  channel  and  the 
differentiated approach Fortegra takes in this market.

Our Insurance Products and Services

Business and Product Mix by Gross Written Premiums and Premium Equivalents

($ in thousands)

Property and short-tail
Contractual liability
General liability
Alternative risks
Professional liability
Europe

Commercial lines
Personal lines
Insurance

Auto and consumer goods warranty
Other services
Services
Total

Year Ended December 31, 
2022

2021

2023

$ 

$ 
$ 
$ 

$ 
$ 

548,984  $ 
396,861
353,011
330,171
232,944
141,208
2,003,179  $ 
382,397  $ 
2,385,576  $ 
302,746
59,532

362,278  $ 
2,747,854  $ 

263,933  $ 
351,869
305,325
363,362
82,340
125,150
1,491,979  $ 
397,423  $ 
1,889,402  $ 
318,550
55,176

373,726  $ 
2,263,128  $ 

100,462 
347,776
182,336
409,807
32,028
95,917
1,168,326 
432,522 
1,600,848 
285,591
49,535
335,126 
1,935,974 

Insurance: Includes lines of business that pertain to coverages written or reinsured, on an admitted or E&S basis, through one of 
Fortegra’s licensed and regulated insurance entities. Insurance lines of business are further presented as those providing benefits to 
commercial  entities,  and  those  which  provide  personal  coverage  benefits  to  end-consumers.  Additionally,  Fortegra’s  European 
lines of business includes auto and consumer goods warranty products, as they are regulated insurance products in their locally-
issued  countries.  Fortegra  gives  limited  delegated  underwriting  authority  to  its  distribution  partners,  allowing  them  authority  to 
quote,  bind  and  issue  policies  within  specifically  agreed-upon  underwriting  guidelines.  Fortegra’s  distribution  partners  do  not 
establish the policy pricing and terms or place reinsurance on its behalf and in most instances do not manage claims on its behalf. 
To  align  economic  interests  in  both  commercial  and  personal  lines  of  business,  distribution  partners  receive  variable  forms  of 
commission based on underlying losses and underwriting performance, which supports the consistency and stability of Fortegra’s 
underwriting results.

•

Commercial:  Through  Fortegra’s  network  of  partner  MGAs,  wholesale  agents,  retail  agents,  and  brokers,  bespoke  admitted 
and E&S coverages are cultivated, ultimately benefiting commercial insureds. The business offers general liability, professional 
liability,  property  and  other  short-tail  coverages,  contractual  liability  protection,  and  alternative  risks  products.  Fortegra 
continues  to  experience  favorable  trends  in  the  E&S  market  in  the  U.S.  while  broadening  its  reach  globally,  including 
throughout Europe. The E&S insurance business launched in 2020 and has grown to more than $820 million of GWPPE for the 
year  ended  December  31,  2023.  By  scaling  operations  to  support  international  growth,  Fortegra  is  able  to  capitalize  on 

11

commonalities across geographies and leverage its shared service platform to drive cost efficiencies. Primarily, the following 
products are offered:

– General Liability, including but not limited to, general and occurrence-basis other liability; commercial multi-peril 

liability;

–

–

Professional  Liability,  including  but  not  limited  to,  professional  and  claims-made  other  liability;  miscellaneous 
errors & omissions; cyber liability;

Property  and  Other  Short-Tail,  including  but  not  limited  to,  commercial  auto  physical  damage;  commercial 
property; earthquake; homeowners; and inland marine;

– Contractual Liability Protection (“CLIP”), within portions of auto & consumer goods warranty lines, an embedded 
CLIP is provided. In these cases, the issuing party separately buys an insurance policy, called a “contractual liability 
insurance  policy”  CLIP  from  an  insurance  company  to  insure  the  financial  obligations  assumed  by  the  issuing 
company;

– Alternative Risks, including credit insurance products designed to offer lenders protection from events that limit a 
borrower’s  ability  to  make  payments  on  outstanding  loan  balances.  Collateral  protection  products  are  designed  to 
primarily  protect  the  commercial  entity  from  losses  to  collateral  pledged  to  secure  an  installment  loan.  In  most 
instances, these products offer lenders the option to protect collateral from a comprehensive loss due to fire, wind, 
flood and theft. Additionally, if the collateral is an automobile, the coverage protects against collision losses.

•

•

Personal:  In  addition  to  commercial  products,  Fortegra’s  distribution  partners  offer  a  range  of  products  which  insure 
consumers, including credit protection surrounding loan payments. These products offer consumers the option to protect loan 
balance  repayment  in  the  event  of  death,  involuntary  unemployment  or  disability.  Additionally,  while  the  business  has 
strategically  and  intentionally  deemphasized  non-standard  auto  coverage,  it  offers  these  products  on  a  limited  basis  through 
select partners.

Services: Includes lines of business that generate service fees and other sources of income through non-insurance services entities. 
Services lines of business are further presented as those servicing auto warranty contracts and all other services. To align economic 
interests with partners and reduce the volatility of underwriting results related to various auto warranty, consumer warranty and 
motor  club  administration  products,  distribution  partners  receive  variable  forms  of  commission  based  on  underlying  losses  and 
overall  program  performance.  A  substantial  portion  of  underwriting  risk  is  typically  ceded  via  third-party  captive  reinsurance 
arrangements.

Auto  &  Consumer  Warranty:  Through  Fortegra’s  network  of  partner  MGAs,  wholesale  agents,  retail  agents,  brokers,  and 
mobile device retailers, many of which also distribute insurance products, the business provides various auto warranty programs 
(including  but  not  limited  to,  vehicle  service  contracts,  GAP,  and  other  ancillary  products),  and  consumer  goods  warranty 
programs  (including  but  not  limited  to,  mobile  devices,  consumer  electronics,  appliances,  furniture,  etc.).  Within  auto  & 
consumer warranty, service fee income is earned for providing any combination of administrator and/or obligor services, both 
within the U.S. and Europe.

• Other  Services:  Fortegra  administers  multiple  forms  of  motor  clubs  marketed  by  distribution  partners,  which  are 
complementary to, and typically embedded within, other insurance or services programs. As part of the expansion into Europe, 
Fortegra  also  provides  regulatory  support  and  compliance  services  to  the  retail  automotive  sector  in  the  U.K.  Included  in 
Fortegra’s  vertically  integrated  insurance  and  services  offerings,  the  business  generates  additional  sources  of  fee  income 
through value-add services, including but not limited to, premium or warranty contract financing, lead generation support, and 
business process outsourcing.

Our Insurance Competitive Strengths

We believe that Fortegra’s competitive strengths include:

Highly  diversified  and  complementary  business  mix  with  an  exclusive  focus  on  underserved  specialty  insurance  markets 
requiring distinct industry expertise. Fortegra has a highly diverse set of specialty programs, focused on classes of business where 
its  underwriters  have  extensive  experience.  The  exclusive  focus  on  programs  that  we  believe  are  frequently  underserved  in  the 
market provides Fortegra a distinct competitive advantage. For example, Fortegra often targets smaller limit lines of business that it 
believes are consistently profitable with significant growth potential but have been overlooked by traditional insurance carriers. Its 
dedicated  underwriters  have  specific  expertise  in  their  given  specialty  markets,  and  will  only  enter  a  new  market  segment  after 
extensive analysis and assessment.

12

Track record of profitable growth driven by disciplined strategic actions. Fortegra delivered GWPPE CAGR of 26%, net income 
CAGR  of  39%  and  an  adjusted  net  income  CAGR  of  37%,  each  measured  from  January  1,  2019  through  December  31,  2023, 
while  increasing  its  return  on  equity  over  that  time,  highlighted  by  its  2023  ROAE  of  26%  and  adjusted  ROAE  of  29%.  The 
business targets and hires underwriters with strong reputations in their areas of expertise and empowers them to source specialty 
programs from their proprietary networks. Once onboarded, Fortegra’s platform is dedicated to improving its agents’ performance 
through  aligned  incentives,  underwriting  and  structural  expertise,  technology  and  data  analytics,  and  ancillary  services  (e.g. 
claims). The platform has expanded into new lines of business and geographies, all while maintaining a disciplined approach to 
risk selection. Growth has been supported by multiple industry tailwinds in recent years, including the continued trend of insurance 
distribution  through  MGAs,  the  secular  migration  of  risks  into  the  U.S.  E&S  market,  the  need  for  reliable  carrier  capacity  as 
traditional insurance carriers, reinsurance providers and alternative capital solutions have experienced dislocation and the persistent 
U.S. P&C insurance hard-market environment.

Stable  and  highly  predictable  underwriting  results  driven  by  differentiated  expertise,  rigorous  data  driven  approach  to  risk 
selection and a fully aligned distribution network. Fortegra has a long-standing track record of consistent underwriting results that 
have  experienced  limited  volatility,  which  is  the  result  of  a  deliberate  organizational  design.  Its  underwriting  track  record  is 
demonstrated through its average combined ratio of 90.9% from 2019 through the year ended December 31, 2023. The business 
takes a disciplined approach to program selection, due diligence, pricing and structuring led by long-tenured, specialty insurance 
underwriting and actuarial experts, with active input from compliance, information technology and legal teams. Fortegra does not 
write  commoditized,  longer-tail  classes  of  business  which  can  experience  periods  of  volatility  such  as  workers  compensation  or 
commercial  auto.  The  stability  of  its  financial  results  is  also  driven  by  an  intense  data  driven  underwriting  approach,  which  is 
enhanced  by  AI  and  machine  learning  to  constantly  refine  pricing  and  risk  appetite.  Lastly,  Fortegra’s  selected  group  of 
distribution partners are fully aligned as a result of variable commission structures which support the consistency and stability of 
underwriting results. 

Agent-centric and highly efficient operating platform driven by scalable and proprietary data, analytics and technology stack. 
Fortegra  complements  underwriting  expertise  with  robust  technology  platforms  supported  by  highly  trained  data  science  and 
engineering teams to improve the scale and profitability of its programs. The platform allows the business to launch new programs 
and  grow  premiums  without  significant  incremental  upfront  expenses.  Fortegra’s  technology  delivers  low-cost,  automated 
administrative  services  to  partners,  enabling  the  business  to  automate  core  business  processes,  reduce  operating  costs,  increase 
operating efficiency and secure high agent retention, highlighted by Fortegra’s five year annual average agent retention of greater 
than 95%. Fortegra uses the data collected to quickly analyze claims, which feeds into underwriting and actuarial teams and their 
decision  making.  Data  and  technology  capabilities  are  used  to  monitor  existing  program  performance,  implement  necessary 
underwriting  action  and  if  appropriate,  exit  programs  which  do  not  meet  Fortegra’s  underwriting  standards.  We  believe  that 
Fortegra’s technology platform provides an advantage in partnering with and delivering value-added capabilities to its distribution 
network. 

Dynamic  capital  allocator  with  a  sophisticated  reinsurance  program  to  optimize  risk  and  return  while  maintaining  a 
conservative  financial  profile.  Fortegra  actively  manages  its  capital  to  ensure  disciplined,  profitable  growth  across  cycles.  Its 
complementary business mix allows the business to pivot rapidly as market conditions change. The business mix is intentionally 
designed  to  have  a  balance  of  risk-bearing  and  capital  light,  fee-based  earnings,  which  we  believe  provides  a  significant 
diversification  benefit  and  allows  us  to  allocate  our  capital  and  focus  as  market  conditions  change.  Additionally,  the  diverse 
business mix enables Fortegra to use the cash flows generated through capital light, fee-based businesses to help fund the growth 
capital  required  in  insurance  businesses.  Fortegra  utilizes  a  sophisticated  reinsurance  strategy  to  optimize  capital  deployed  and 
reduce volatility while generating attractive economics. This strategy is further augmented by Fortegra’s conservative balance sheet 
and highly liquid fixed income investment portfolio which has an average S&P rating of AA.

Visionary, proven, and deep leadership team with a collaborative culture. Fortegra’s executive management team is comprised of 
highly  experienced  professionals  with  an  average  of  over  25  years  of  industry  experience.  The  team  includes  a  deep  bench  of 
seasoned  underwriters  who  have  expertise  in  their  designated  specialization  driving  underwriting  performance.  The  culture  is 
highly  collaborative  focused  on  continuous  improvement  across  underwriting,  claims,  technology  and  operations  to  ensure 
enterprise-wide connectivity as the business scales. Fortegra is led by its Chief Executive Officer, Rick Kahlbaugh, who has been 
in executive leadership positions with the Company for over 20 years. Fortegra prioritizes attracting and investing in the best talent 
in the industry to continue to drive profitable growth. The interests of Fortegra’s executive management team are closely aligned 
with investors through a combination of a long-term incentive plan and management bonus pool tied to operating results. 

13

Our Insurance Strategy

We will seek to continue to execute upon our strategy, which focuses on providing specialty lines to underserved markets where 
Fortegra  has  significant  expertise.  We  believe  this  approach  will  enable  Fortegra  to  continue  to  generate  profitable  growth  and 
attractive returns on capital. The core drivers of this strategy include:

Leveraging our deep expertise and efficient distribution to continue driving profitable growth. Fortegra’s core strategy centers on 
its  deep  expertise  in  underserved  markets  and  a  distinctive  approach  to  program  business.  We  expect  to  actively  pursue  new 
specialty opportunities through: 

•

•

•

Continuing to successfully recruit and hire talented specialty underwriters that have a favorable track record, sector expertise 
and strong agent following; 

Leveraging Fortegra’s distribution partner network to enter new specialty programs where it has underwriting expertise;

Partnering with reinsurers who are looking for highly experienced specialty carriers like Fortegra that can deliver a breadth of 
services and favorable underwriting results;

• Working  with  reinsurance  intermediaries  that  are  seeking  to  move  their  business  away  from  the  fronting/hybrid  model  to  a 

fully integrated specialty insurance company model;

•

•

Expanding into new geographies including the specialty insurance and warranty markets in Europe; and

Deepening Fortegra’s auto warranty footprint through dealership expansion and build-out of a direct salesforce.

Utilizing technology to strengthen Fortegra’s operational scalability and continue to refine underwriting performance. At the 
core  of  the  strategic  vision  is  a  profound  commitment  to  technology  as  a  driving  force  behind  its  success.  The  scalability  and 
adaptability of its technology seamlessly aligns with an expanding business landscape. This dynamic technological infrastructure 
empowers the Fortegra team through the integration of data tools across claims, underwriting, and actuarial functions, providing a 
significant competitive edge and contributing to a low expense ratio. Technology and data capabilities are leveraged to enhance 
agent  experience  and  performance  through  elevated  service,  improved  underwriting  insights,  and  streamlined  claims  processes. 
Fortegra’s technology and data also generate underwriting-qualified leads for its distribution partners, while ensuring the business 
remains within the boundaries of its risk parameters. This scalable technology platform was designed to support continued growth 
while necessitating minimal incremental investment.

Empowering  partners  for  enhanced  performance  through  its  differentiated  underwriting  approach.  Fortegra’s  distinctive 
underwriting approach involves the recruitment of experienced underwriters which are typically very well known to the business 
and  have  established  networks  of  experienced  distribution  partners.  These  partners  play  a  pivotal  role  in  identifying  attractive, 
smaller  programs  that  align  within  Fortegra’s  risk  parameters.  Alignment  of  interests  with  distribution  partners  provides  them 
access  to  pricing,  underwriting,  and  robust  risk  management  processes,  which  enhance  the  collective  financial  performance. 
Fortegra’s  organizational  culture  is  rooted  in  sound  underwriting  practices  that  enable  it  to  achieve  targeted  growth  objectives 
while consistently delivering desired profitability.

Sustaining  a  highly  disciplined  underwriting  approach  with  focus  on  profitability.  Fortegra  constantly  assesses  the  risks  in  its 
portfolio to assure sound pricing and risk management in accordance with its underwriting guidelines with the goal of increasing 
returns  and  maintaining  the  stability  of  its  combined  ratio.  Underwriting  integrity  or  risk  selection  will  not  be  sacrificed  for  the 
sake of premium growth. As Fortegra assesses market pricing, to the extent it is below its underwriting return objectives, capital 
will not be put at risk for premium growth.

Maintaining  a  high-quality  balance  sheet  with  strong  ratings.  Fortegra  has  and  seeks  to  maintain  a  strong  and  conservative 
balance  sheet,  supported  by  a  comprehensive  risk  management  program  reflected  by  its  financial  strength  ratings  of 
“A-” (Excellent) (Outlook Stable) from A.M. Best. Fortegra has a short duration, liquid and high-quality investment portfolio, with 
90% invested in cash and investment grade fixed income securities, which have an average S&P rating of AA, as of December 31, 
2023. Fortegra has highly rated and well capitalized reinsurance partners and retains excess collateral where applicable to support 
its outstanding reinsurance recoverable.

Distribution & Marketing 

Fortegra  distributes  its  products  through  MGAs,  retail  agents,  and  other  distributors,  collectively  referred  to  as  distribution 
partners.  The  business  generally  targets  markets  that  are  niche  and  specialty  in  nature,  which  it  believes  are  underserved  by 

14

competitors and have high barriers to entry. Fortegra focuses on establishing quality relationships, emphasizing customer service, 
and providing underwriting expertise and value-added services. This agent-centric focus, along with its ability to help distribution 
partners enhance revenue and optimize underwriting profitability and operational efficiencies, provides Fortegra with a competitive 
advantage  that  has  enabled  it  to  develop  and  maintain  numerous  long-term  client  relationships,  as  evidenced  by  its  high  agent 
retention  rate  of  greater  than  95%  (over  the  last  five  years).  Fortegra  believes  this  “one-to-many”  distribution  model  is 
operationally  more  efficient  for  the  types  of  risks  it  underwrites,  leveraging  its  partners’  specialized  experience  in  their  specific 
markets, lines of business and associated risks, as well as their extensive retail networks. To align economic interests, distribution 
partners  receive  variable  forms  of  commission  based  on  underwriting  performance,  which  reduces  the  volatility  of  underwriting 
results and promotes further profitable growth. 

Fortegra’s distribution partner relationships vary across the insurance products and services that it offers as follows:

•

•

Insurance  products  are  distributed  primarily  through  a  network  of  MGAs,  who  in  turn  market  and  distribute  through 
independent agents, retailers and wholesale brokers, or direct through lenders and financial institutions. 

Service products are distributed by automobile dealerships, retailers (regional and specialty retailers, furniture stores, regional 
cellular  service  providers,  and  mobile  device  service  providers),  and  MGAs,  as  well  as  financial  services  companies. 
Fortegra’s  vertically  integrated  platform  also  allows  it  to  engage  in  direct  relationships  with  distributors  for  premium  and 
service contract financing options, and regulatory compliance. 

Fortegra’s  partners  receive  a  commission-based  fee  for  the  distribution  of  its  products.  A  significant  portion  of  Fortegra’s 
commission agreements are on a variable or sliding scale commission basis, which allows Fortegra to adjust commissions based 
upon underlying underwriting performance, economically aligning itself with distribution partners.

Fortegra  has  a  highly  diverse  set  of  programs  designed  to  limit  concentration  risk  to  its  distribution  partners,  with  its  largest 
distribution partners each representing less than 6% of GWPPE for the year ended December 31, 2023. 

Fortegra’s marketing department focuses on building tailored solutions for its distribution partners, playing a pivotal role in driving 
brand  recognition,  revenue  growth,  and  partner  engagement.  Utilizing  a  data-driven  approach,  the  team  develops  and  executes 
marketing strategies that support Fortegra’s sales activities, and the customer acquisition efforts of distribution partners. Extending 
marketing capabilities to distribution partners is a key differentiator that contributes to revenue growth and promotes longstanding 
distribution relationships.

Underwriting

Fortegra is an underwriting focused company with deep expertise within admitted and E&S insurance lines, as well as fee-based 
services markets, with a focus on underwriting complex and niche risks in underserved markets. Throughout the organization there 
is  a  strong  culture  of  collaboration.  Underwriting,  claims  and  actuarial  teams  are  closely  integrated  and  aligned  to  facilitate 
operational efficiency, continuously monitor results, and make changes to programs as necessary. Centralized data systems allow 
for the real-time identification of pricing and claims trends within a program. Fortegra believes its approach to partner and program 
diligence, underwriting (including risk selection and pricing), and claims management, combined with its alignment and ability to 
improve  its  partner’s  performance,  has  contributed  to  a  superior  combined  ratio,  which  averaged  90.9%  from  2019  through 
December 31, 2023.

Fortegra’s underwriting team consisted of over 90 professionals as of December 31, 2023. Fortegra hires experienced underwriters 
with  a  proven  track  record  of  underwriting  profitability,  deep  knowledge  of  the  specialty  products  that  they  underwrite,  and 
longstanding  relationships  with  its  distribution  partners.  This  approach  accelerates  expansion  within  particular  lines  due  to  the 
underwriters’ historical experience. Fortegra benefits from the underwriters’ prior experience within a particular line of business 
without the cost and volatility associated with unproven, blue-sky initiatives. 

Fortegra’s  underwriters  work  with  its  distribution  partners  to  develop  the  underwriting  guidelines  for  each  program.  Limited 
delegated underwriting authority is given to its MGAs, including the ability to quote, bind, and issue policies within specifically 
agreed-upon  underwriting  guidelines.  Fortegra’s  distribution  partners  do  not  establish  the  policy  pricing  and  terms,  nor  do  they 
place reinsurance on its behalf. Fortegra has an established data and process-based approach to initial due diligence, structuring and 
onboarding, and regular maintenance and oversight.

Fortegra’s  underwriting  team  prices  to  a  target  margin,  accounting  for  claims  and  administrative  services.  Fortegra  continually 
seeks risk exposures where it can sustainably improve loss ratios and adjust its underwriting accordingly. Each program must be 
profitable  on  its  own  or  adjustments  are  made,  including  underwriting  guideline  changes,  pricing  adjustments,  or  ultimately 
program cancellation if an underperforming program cannot be rehabilitated. This benefits underwriting results, and also earns its 
partners additional economic benefits through its variable commission structures.

15

Fortegra’s partners are compensated through variable or sliding-scale commission agreements, which allows the business to adjust 
commissions based upon underlying underwriting performance. Under these types of arrangements, its partners are paid an upfront 
provisional  commission  based  on  volumes.  Subsequent  adjustments  to  these  commissions  are  calculated  on  underlying 
performance based upon the actual losses incurred compared to premiums or service fee income earned. Fortegra believes these 
types of contractual arrangements align economic interests by sharing the risks and rewards of its programs, which help Fortegra to 
better  manage  its  risk  exposures  and  deliver  more  consistent  profit  margins.  This  alignment  underpins  all  of  Fortegra’s 
partnerships; it fosters collaboration, lasting relationships and consistent profitability.

Claims

Fortegra’s claims department consisted of over 300 claims professionals as of December 31, 2023. Fortegra organizes its claims 
department  by  product  and  geography,  with  specialized  teams  aligned  by  area  of  expertise.  The  business  maintains  claims 
disposition authority for the majority of its claims across both insurance and services. In-house claims professionals have specific 
niche  expertise  to  accurately  assess  claims,  which  is  crucial  for  the  unique  risks  the  business  underwrites.  Fortegra’s  claims 
department  maintains  close  collaboration  with  its  underwriting  and  actuarial  teams  as  to  current  claims  trends  and  ongoing 
underwriting performance. 

On certain occasions where a TPA or external specialist possesses specific expertise, Fortegra may contract with them to provide 
services  within  its  defined  framework,  subject  to  oversight  while  Fortegra  retains  ultimate  claims  settlement  authority.  When 
necessary, the claims team has access to a panel of expert attorneys, mediators, investigators, and independent adjusters who will 
be retained in connection with litigation or loss inspection. This allows Fortegra’s claims professionals to focus on more complex 
claims and enhances the efficiency and work quality of its claims department. The business seeks to adjudicate claims efficiently 
while maintaining strict compliance with all licensing, regulatory, and statutory requirements.

Fortegra continues to invest in claims technology that enables it to add new programs and scale rapidly. Its centralized data systems 
allow for the real-time identification of claims trends within a program, which can be fed back to underwriting and actuarial teams 
to adjust its underwriting accordingly.

Technology

Technology  is  core  to  Fortegra’s  strategy  and  a  competitive  advantage  for  the  business.  Fortegra  has  invested  in  technology  to 
complement and enhance its underwriting, actuarial, and claims expertise, including systems, data science and engineering, and AI. 
These investments have strengthened Fortegra’s overall operational framework, improving scalability and profitability for both the 
business  and  its  partners.  Core  system  enhancements  afford  better  claims  adjudication,  inform  precise  claims  data  capture,  and 
provide  improved  customer  service,  while  data  engineering  connects  existing  systems  to  reduce  human  intervention.  The 
enrichment of claims data enhances underwriting decisions and actuarial analyses with extensive integrated data science tools. 

The business is supported by technology in multiple ways, including: 

•

•

•

•

Assisting  underwriting  and  actuarial  teams  by  providing  data  and  insight  that  feeds  into  its  decision  making  processes. 
Fortegra’s  underwriting  is  complemented  by  its  highly  trained  data  science  and  engineering  teams.  These  teams  deploy 
machine learning tools and a scalable data platform to support a collaborative approach that has allowed Fortegra to improve 
the scale and profitability of its business. The machine learning tools that the data science team build start with input from the 
underwriting  and  actuarial  teams  to  build  bespoke  models  for  select  lines  that  provide  meaningful  insight  back  to  the 
underwriters  in  their  processes.  Fortegra  leverages  machine  learning  in  its  marketing  processes  to  produce  underwriting-
qualified leads for its distribution partners. In the claims process, Fortegra utilizes machine learning document processing to 
streamline claims intake and improve data quality;

Improving  its  service  platform  to  make  it  easier  to  do  business  with  its  distribution  partners  and  effectively  serve  a  high 
volume  of  policies  in  an  efficient  manner.  This  integrated,  proprietary  technology  efficiently  manages  the  high  volume  of 
policies  and  claims  that  result  from  servicing  a  large  volume  of  small  policyholders  and  contract  holders.  Its  technology  is 
highly automated, scalable and allows Fortegra to operate efficiently;

Enhancing its ability to generate business leads that fit Fortegra’s risk profile using AI. Fortegra’s flexible technology platform 
provides  value-added  services  that  it  believes  creates  stronger  relationships  with  its  distribution  partners.  Fortegra’s 
technology  platform  is  connected  to  its  distribution  partners  and  provides  them  with  access  to  claims  and  performance 
dashboards.  These  value-added  services  deepen  its  relationships  and  contribute  to  the  high  persistency  rate  with  Fortegra’s 
distribution partners; and

Providing a scalable platform to grow the business and add new product lines with minimal incremental expense. Fortegra’s 
technology  infrastructure  is  scalable  and  affords  it  the  opportunity  to  add  new  partners  and  services  without  significant 

16

additional  expense.  Fortegra  designed  its  scalable  technology  platform  to  support  the  business’s  continued  growth  while 
necessitating only minimal incremental investment.

Reinsurance Strategy

Fortegra’s reinsurance strategy fosters efficient capital management to enable continued growth of its specialty insurance platform. 
The  business  leverages  both  quota  share  and  excess  of  loss  reinsurance  arrangements  with  a  diverse,  highly  rated,  and 
appropriately  capitalized  panel  of  reinsurers.  Reinsurance  is  also  a  key  element  of  its  enterprise  risk  management  framework, 
limiting extreme loss events, reducing volatility, and driving consistent underwriting profitability for the stockholders. 

Quota  share  reinsurance:  refers  to  a  reinsurance  contract  whereby  the  reinsurer  agrees  to  assume  a  specified  percentage  of  the 
ceding  company’s  losses  arising  out  of  a  defined  class.  Fortegra  has  various  quota  share  contracts  that  cover  its  insurance 
programs. Fortegra’s whole account quota share reinsurance agreement, which covers a portion of its commercial P&C insurance 
gross written premium (including general liability, professional liability, property and short-tail), provides a 60% quota share of 
losses  and  significant  ceding  fees  to  offset  administrative,  underwriting  and  acquisition  expenses.  Additionally,  this  reinsurance 
agreement generates ceding commission income based on underlying underwriting performance, and investment income earned by 
the assuming reinsurers.

Excess of loss reinsurance: refers to a reinsurance contract whereby the reinsurer agrees to assume all or a portion of the ceding 
company’s losses for an individual claim or an event in excess of a specified amount in exchange for a premium payable amount 
negotiated between the parties. Fortegra utilizes an excess of loss reinsurance agreement related to catastrophic property exposures, 
with limits in excess of a 1:200-year event.

Captive  Reinsurance  Arrangements:  A  significant  portion  of  partners  within  contractual  liability  and  alternative  risk  lines  of 
insurance business, as well as its auto and consumer goods line of services business, have created captive reinsurance companies to 
assume  the  underwriting  risk  on  the  products  it  delivers.  These  captive  reinsurance  companies  are  known  as  Producer-Owned 
Reinsurance  Companies  (“PORCs”)  and,  in  most  instances,  each  PORC  assumes  predominantly  all  of  the  underwriting  risk 
associated with the products they deliver. In such PORC relationships, as is typically required by applicable laws and insurance 
regulations,  Fortegra  acts  in  a  fronting  and  administrative  capacity  on  behalf  of  the  PORC,  providing  underwriting  and  claims 
services.  It  receives  ceding  and  administration  fees  associated  with  underwriting  and  servicing  the  underlying  policies.  Because 
reinsurance does not relieve Fortegra of its primary liability to the policyholder, Fortegra generally requires cash or other forms of 
collateral posted by the PORC to secure the reinsurance receivable if a PORC is unable to pay the claims it has assumed. 

Fortegra’s reinsurance treaties renew on an annual basis throughout the year. At each treaty renewal, Fortegra considers several 
factors that influence its reinsurance program, including any plans to change the underlying insurance coverage it offers, changes 
in loss trends, its capital levels, changes in its risk appetite and the cost and market capacity.

The following table reflects Fortegra’s key reinsurance treaties: 

Treaty

Whole Account Quota Share

Description
Covers general liability, professional 
liability, property and short-tail lines 
accounting for 40% of commercial 
P&C insurance gross written 
premiums

Net Retention

Reinsurance Coverage

40%, $5 million per aggregate

60% Placed

Property Catastrophe Excess of Loss

Protection in excess of a 1:200-year 
catastrophic event

$8 million, 50% co-participation on 
$4 million excess of $8 million

$40 million excess of $8 million per 
event, $80 million in aggregate

For  the  limited  amount  of  gross  property  exposures  that  are  in  excess  of  desired  retentions,  Fortegra  works  with  its  distribution 
partners  to  purchase  facultative  reinsurance  to  cover  those  individual  risks.  In  addition  to  the  purchase  of  property  catastrophe 
reinsurance, Fortegra also manages its property exposures by leveraging catastrophe models to monitor risk aggregations that are 
measured in terms of probable maximum loss (“PML”) and Tail Value-at-Risk (“TVAR”), both of which estimate the amount of 
loss it would expect in extreme loss scenarios. 

In Fortegra’s commercial insurance lines, its reinsurers tend to be highly rated, well-capitalized, professional third-party reinsurers. 
Fortegra typically contracts with third-party reinsurers that have attained an “A-” or better financial strength rating from A.M. Best. 
Those reinsurers that fall below this threshold are required to post collateral on a funds held basis or with letters of credit.

Counterparty Risk

Fortegra  monitors  its  counterparty  risk  monthly  through  both  adjustments  to  the  sliding  scale  commission  arrangements  and  a 
thorough evaluation of its reinsurance receivables and prepaid insurance premiums, and associated collateral.

17

($ in millions)

Third-party captives (1)
Reinsurance receivables and prepaid reinsurance premiums
Collateral
% Collateralized
Professional Reinsurers (2)
Reinsurance receivables and prepaid reinsurance premiums
Collateral
% Collateralized
Total
Reinsurance receivables and prepaid reinsurance premiums
Collateral
% Collateralized

__________________
(1) Includes domestic insurance companies owned by distribution partners.
(2) “Professional reinsurers” include all reinsurers except for third-party captives.

As of December 31,

2023

2022

$ 
$ 

$ 
$ 

$ 
$ 

$ 
$ 

$ 
$ 

$ 
$ 

871 
1,036 

 119 %

984 
644 
 65 %

1,854 
1,680 

 91 %

603 
700 
 116 %

573 
611 
 107 %

1,176 
1,311 

 112 %

Total reinsurance receivables and prepaid reinsurance premiums were $1,854 million and $1,176 million as of December 31, 2023 
and  2022,  respectively.  Of  those  amounts,  $871  million  and  $603  million,  respectively,  related  to  contracts  with  third-party 
captives  in  which  Fortegra  holds  collateral  or  receives  letters  of  credit  in  excess  of  the  reinsurance  receivables  and  prepaid 
reinsurance  premiums.  The  remainder  relates  to  receivables  held  with  high  quality  professional  reinsurers.  Additionally,  any 
receivable  held  with  unrated  professional  reinsurers  is  fully  collateralized.  The  following  table  sets  forth  the  percentage  of 
Fortegra’s reinsurance receivables broken out by the A.M. Best financial strength rating of those professional reinsurers, excluding 
gross-up adjustments, as of December 31, 2023 and 2022.

Rating:
A++
A+
A
A-
Unrated

Reserves

Percentage as of December 31,

2023

2022

 1 %
 19 %
 26 %
 28 %
 26 %

 1 %
 33 %
 13 %
 30 %
 23 %

Fortegra  establishes  loss  reserves  to  cover  its  estimated  ultimate  losses  under  all  insurance  policies  that  it  underwrites,  and  loss 
adjustment expenses relating to the investigation and settlement of policy claims. These reserves include estimates of the cost of 
the  claims  reported  to  Fortegra  (case  reserves)  and  estimates  of  the  cost  of  claims  that  have  been  incurred  but  not  yet  reported. 
Fortegra’s reserving process is built upon expected loss and loss adjustment expense ratio picks at the program, line of business, 
and accident year level, which are set by management with input from underwriting, actuarial and claims. Management reviews 
results monthly against expected results to monitor underwriting performance. When determined necessary, underwriting actions 
are discussed and implemented, and reserve changes are made.

Regular internal actuarial analyses are performed on a quarterly basis by program, line of business, and accident year/treaty year. 
Quarterly, an independent third-party actuarial review is completed to provide management with additional information related to 
reserve  adequacy.  Where  the  internal  and  external  projections  differ,  a  comparison  is  examined  to  determine  the  drivers. 
Information  provided  by  the  independent  actuaries  is  considered  as  part  of  the  input  in  the  internal  reserving  process.  Unpaid 
claims reserves represent Fortegra’s best estimates at a given time, based on actuarial estimates. Actual claim costs are dependent 
upon  a  number  of  complex  factors  such  as  changes  in  doctrines  of  legal  liabilities  and  damage  awards.  These  factors  are  not 
directly  quantifiable,  particularly  on  a  prospective  basis.  Fortegra  regularly  reviews  and  updates  its  method  of  estimating  such 
unpaid claims reserves based on actual claims experience.

Fortegra’s  actuaries  apply  a  variety  of  generally  accepted  actuarial  methods  (including  loss  development  methods,  Bornhuetter-
Ferguson  methods,  Cape  Cod  methods,  and  expected  loss  methods)  to  historical  loss  experience  when  calculating  indicated 
reserves. Key assumptions underlying these analyses, including anticipated future loss development patterns and expected ultimate 
loss  and  loss  adjustment  expense  ratios,  are  reviewed  regularly  and  updated  as  needed  based  on  actual  claims  experience.  In 
accordance with applicable statutory insurance company regulations, Fortegra’s recorded unpaid claims reserves are evaluated by 

18

appointed independent third-party actuaries, who perform this function in compliance with the Standards of Practice and Codes of 
Conduct of the American Academy of Actuaries. 

As of December 31, 2023, Fortegra’s reserves were found to be consistent with reserves computed in accordance with actuarial 
standards of practice and make a reasonable provision for all of its unpaid loss and loss adjustment expense obligations, as well as 
its unearned premium reserves for long duration contracts, by the appointed independent third-party actuaries.

Insurance Investments

Fortegra  seeks  to  maintain  a  balanced  and  well-diversified  investment  portfolio  with  the  primary  investment  objectives  of 
remaining  liquid  to  fund  expected  reserve  payments,  capital  preservation,  and  a  stable  level  of  investment  income  enabling 
continued  growth  of  core  and  new  business  lines.  Its  investment  portfolio,  including  cash  and  cash  equivalents  and  total 
investments, were $1,327 million as of December 31, 2023.

Fortegra’s investment policy establishes the investment parameters, such as maximum percentage of investment in a certain type of 
security  and  minimum  levels  of  credit  quality  and  is  designed  to  manage  investment  risk.  Corvid  Peak  Capital  Management,  a 
credit  oriented  asset  manager  owned  by  the  Company,  manages  Fortegra’s  investment  portfolio  consistent  with  its  internally 
prescribed  guidelines  and  with  oversight  from  Tiptree.  Fortegra’s  investments  are  subject  to  general  economic  conditions  and 
market risks in addition to risks inherent to particular securities and risks relating to the performance of its investment advisers. 
Fortegra conducts monthly stress tests and uses predictive analytics to manage its investments, which it believes reduces risk to its 
investment performance. Fortegra also maintains an investment committee that meets monthly to ensure its investment objectives 
remain aligned with its broader strategic and financial objectives.

As of December 31, 2023, the majority of its investments, $772 million or 58.2%, of total cash and invested assets, was comprised 
of fixed maturity securities that are classified as available for sale and carried at fair value with unrealized gains and losses on these 
securities,  net  of  applicable  taxes,  reported  as  a  separate  component  of  AOCI.  Cash  &  cash  equivalents  were  $410  million,  or 
approximately 30.9% of total cash and invested assets as of December 31, 2023, as Fortegra has intentionally maintained a larger 
cash portion in its portfolio to capitalize on current short-term yields and maintain liquidity. Also included in its investments were 
$26 million of equity securities, $11 million of loans, at fair value, $1 million of exchange traded fixed income funds, at fair value, 
and $107 million of other investments.

The following table provides a summary of Fortegra’s investments and cash and cash equivalents as of December 31, 2023 and 
December 31, 2022:

($ in millions)

December 31, 2023

December 31, 2022

As of

Investments:
Cash and cash equivalents   .................................................................................................... $ 
Available for sale securities, at fair value     ............................................................................
Loans, at fair value     ...............................................................................................................
Common and preferred equity securities    .............................................................................
Exchange traded funds     .........................................................................................................
Other investments    .................................................................................................................

Total cash and invested assets ......................................................................................... $ 

Fair Value
410 
772 
11 
26 
1 
107 
1,327 

% of Total 
Fair Value

 30.9 % $ 
 58.2 %  
 0.8 %  
 1.9 %  
 0.1 %  
 8.0 %  
 100.0 % $ 

Fair Value
388 
612 
14 
17 
56 
66 
1,154 

% of Total 
Fair Value
 33.7 %
 53.0 %
 1.2 %
 1.5 %
 4.9 %
 5.7 %
 100.0 %

Fixed Maturity Securities

As  of  December  31,  2023,  Fortegra’s  fixed  maturity  securities  totaled  $1,191.5  million  and  included  cash  and  cash  equivalents, 
available for sale securities, at fair value and investment grade securities classified in other investments. It had a weighted-average 
effective duration of 2.5 years, an average S&P rating of AA, and a book yield of 3.3%. Fixed maturity securities represented 90% 
of total investments.

19

 
 
 
 
 
The  following  table  provides  a  summary  of  Fortegra’s  amortized  cost  and  fair  value  on  available  for  sale  securities  as  of 
December 31, 2023 and December 31, 2022: 

($ in millions)

Fixed Maturity Securities:
Obligations of the U.S. Treasury and U.S. Government 

December 31, 2023

December 31, 2022

Amortized 
Cost

Fair Value

% of Total 
Fair Value

Amortized 
Cost

Fair Value

% of Total 
Fair Value

As of

agencies     ............................................................................. $ 

Obligations of state and political subdivisions     ........................
Corporate securities  .................................................................
Asset-backed securities  ............................................................
Certificate of deposits   ..............................................................
Obligations of foreign governments    ........................................

Total available for sale investments      ................................... $ 

467  $ 
49 
261 
29 
1 
5 
812 

441 
45 
255 
26 
1 
5 
$772

 57.1 % $ 
 5.8 %  
 33.0 %  
 3.4 %  
 0.1 %  
 0.6 %  
 100 % $ 

417  $ 
54 
176 
20 
1 
3 
671 

382 
49 
162 
15 
1 
2 
$612

 62.4 %
 8.0 %
 26.5 %
 2.5 %
 0.2 %
 0.3 %
 100 %

The following table provides the credit quality of Fortegra’s available for sale investments as of December 31, 2023 and December 
31, 2022: 

($ in millions)

December 31, 2023

December 31, 2022

As of

Amortized 
Cost

% of Total 
Fair Value

Amortized 
Cost

Rating:
AAA    .................................................................................. $ 
AA    .....................................................................................
A   ........................................................................................
BBB   ..................................................................................
BB    .....................................................................................
B or unrated  .......................................................................

Total available for sale investments  ............................ $ 

Fair Value
27 
509 
154 
65 
12 
5 
772 

29  $ 
540 
162 
64 
12 
5 
812  $ 

 3.5 % $ 
 65.9 %  
 19.9 %  
 8.4 %  
 1.6 %  
 0.6 %  
 100 % $ 

Fair Value
19 
440 
150 
— 
1 
1 
611 

21  $ 
480 
164 
— 
1 
4 
670  $ 

% of Total 
Fair Value
 3.1 %
 72.0 %
 24.5 %
 — %
 0.2 %
 0.2 %
 100 %

The  amortized  cost  and  fair  value  of  Fortegra’s  available  for  sale  investments  is  summarized  by  contractual  maturity  as  of 
December 31, 2023 in the table below. Expected maturities may differ from contractual maturities because borrowers may have the 
right to call or prepay obligations.

($ in millions)

As of December 31, 2023

Amortized 
Cost

Fair Value

% of Total 
Fair Value

Due in one year or less    ..................................................................................................................... $ 
Due after one year through five years  ..............................................................................................
Due after five years through ten years   .............................................................................................
Due after ten years      ...........................................................................................................................
Asset-backed securities   ....................................................................................................................

Total available for sale investments  ........................................................................................... $ 

217  $ 
319
46
200
29

812  $ 

216 
307
39
183
26
772 

 28 %
 40 %
 5 %
 24 %
 3 %
 100 %

Competition

Fortegra  operates  in  several  niche  markets  and  believes  that  no  single  company  competes  against  it  in  all  of  its  business  lines. 
Fortegra may compete with other specialty insurance carriers within a given line of business, but it identifies no specific insurers as 
clear competition across all underwritten lines. Within the United States, Fortegra competes with specialty insurers such as RLI 
Corporation, W.R. Berkley Corporation, Kinsale, Skyward Specialty and Markel Corporation. Across Fortegra’s varying lines of 
business, it competes with a number of companies that write similar products, including: AIG, Allstate, Assurant, Asurion, LLC, 
AXA SA, Securian Financial, and Great American. These lists are not exhaustive and are constantly evolving as underwritten lines 
for Fortegra and its competitors evolves.

In  general,  the  insurance  markets  in  which  Fortegra  operates  in  are  highly  competitive.  The  competition  faced  is  driven  by  a 
confluence of factors, including product pricing, industry knowledge and expertise, quality of customer service, effectiveness of 
distribution  channels,  technology  platforms  and  underwriting  processes,  the  quality  of  information  systems,  financial  strength 
ratings,  size,  breadth  of  products  offered,  overall  reputation,  and  other  factors.  Fortegra  primarily  competes  by  leveraging  its 

20

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
proprietary technological innovations, decades of underwriting expertise, robust distribution relationships, data-driven marketing 
initiatives, its “agent-centric” mentality, and best-in-class reputation.

Ratings

Fortegra currently has a rating of “A-” (Excellent) (Outlook Stable) from A.M. Best, which rates insurance companies based on 
factors  of  concern  to  policyholders.  A.M.  Best  currently  assigns  16  ratings  to  insurance  companies,  which  currently  range  from 
“A++” (Superior) to “S” (Rating Suspended). “A-” (Excellent) is the fourth highest rating. In evaluating a company’s financial and 
operating  performance,  A.M.  Best  performs  quantitative  and  qualitative  analyses,  which  includes  a  review  of  the  company’s 
balance sheet strength, operating performance and business profile. Each of A.M. Best’s ratings reflect its opinion of an insurance 
company’s financial strength, operating performance and ability to meet its obligations to policyholders. These evaluations are not 
directed to purchasers of an insurance company’s securities.

Seasonality

Fortegra’s financial results have historically been, and we expect will continue to be, affected by seasonal variations. Fortegra’s 
commercial P&C lines of business are subject to underlying program renewal dates, while a significant portion of revenues related 
to  the  alternative  risks  and  auto  and  consumer  goods  warranty  lines  of  business  may  fluctuate  seasonally  based  on  consumer 
spending,  which  has  historically  been  higher  in  September  and  December,  corresponding  to  auto-sales  events  and  the  back-to-
school and holiday seasons. Accordingly, its insurance revenues have historically been higher in the third and fourth quarters than 
in the first half of the year.

Intellectual Property

Fortegra owns or licenses a number of trademarks, trade names, service marks, trade secrets and other intellectual property rights 
that relate to its services and products within the various jurisdictions in which it operates. Although Fortegra believes that these 
intellectual property rights are, in the aggregate, important to Fortegra, it also believes that the business is not materially dependent 
upon  any  particular  trademark,  trade  name,  copyright,  service  mark,  license  or  other  intellectual  property  right.  Additionally, 
Fortegra’s insurance subsidiaries have entered into confidentiality agreements with its partners that impose restrictions on partners’ 
use of proprietary software and other intellectual property rights.

Regulation

Fortegra  is  subjected  to  federal,  state,  local  and  foreign  regulation  and  supervision.  The  type  and  degree  of  regulation  and 
supervision  varies  depending  on  which  type  of  license  may  be  involved,  such  as:  insurance  company,  administrator  and  agency 
licenses;  or  service  contract  administration  and  obligor  licenses;  or  premium  finance  and  consumer  finance  licenses.  Fortegra  is 
also subject to the related federal, state and foreign data privacy and data protection laws. Its insurance subsidiaries are active in 50 
states in the United States.

Its  U.S.  insurance  company  subsidiaries  are  domiciled  in  several  states,  including  Arizona,  California,  Delaware,  Georgia, 
Kentucky  and  Louisiana.  The  regulation,  supervision  and  administration  by  state  departments  of  insurance  relate,  among  other 
things, to: standards of solvency that must be met and maintained, restrictions on the payment of dividends, changes in control of 
insurance  companies,  the  licensing  of  insurers  and  their  agents  and  other  producers,  the  types  of  insurance  that  may  be  written, 
privacy practices, the ability to enter and exit certain insurance markets, the nature of and limitations on investments and premium 
rates, or restrictions on the size of risks that may be insured under a single policy, reserves and provisions for unearned premiums, 
losses and other obligations, deposits of securities for the benefit of policyholders, payment of sales compensation to third parties, 
approval of policy forms and premium rates, the types of risks that are not subject to form and rate regulation, the regulation of 
market  conduct,  including  advertising,  underwriting,  claims  practices,  policy  cancellation  or  non-renewal,  and  the  insurer’s 
oversight of its agents. As part of their routine regulatory oversight process, state insurance departments conduct periodic detailed 
financial examinations of the books, records, accounts and operations of insurance companies that are domiciled in their states. In 
addition, our insurance subsidiaries are generally restricted by the insurance laws of their respective domiciles as to the amount of 
dividends they may pay without the prior approval of the respective regulatory authorities. Generally, the maximum dividend that 
may be paid by an insurance subsidiary during any year without prior regulatory approval is limited to a stated percentage of that 
subsidiary’s statutory surplus as of a certain date, or net income of the subsidiary for the preceding year.

Fortegra’s insurance company subsidiaries are also subject to certain state regulations that define eligible investments and establish 
diversification requirements and concentration limits among asset classes. Failure to comply with these regulations would cause 
non-conforming investments to be treated as non-admitted assets in the states in which it is licensed to sell insurance policies for 
purposes of measuring statutory surplus and, in some instances, would require Fortegra to sell those investments. Such investment 
laws are generally permissive with respect to federal, state and municipal obligations, and more restrictive with respect to corporate 
obligations, particularly non-investment grade obligations, foreign investment, equity securities and real estate investments. Each 

21

insurance company is therefore limited by the investment laws of its state of domicile from making excessive investments in any 
given security (such as single issuer limitations) or in certain classes or riskier investments (such as aggregate limitation in non-
investment grade bonds) or in its affiliates.

The  NAIC  provides  model  insurance  laws  and  regulations  for  adoption  by  the  states  and  standardized  insurance  industry 
accounting  and  reporting  guidance.  However,  model  insurance  laws  and  regulations  only  become  effective  when  adopted  and 
enacted  by  the  states,  and  statutory  accounting  and  reporting  principles  continue  to  be  established  by  individual  state  laws, 
regulations and permitted practices. The NAIC has adopted a model act with risk-based capital (“RBC”) formulas to be applied to 
insurance  companies  to  measure  the  minimum  amount  of  capital  appropriate  for  an  insurance  company  to  support  its  overall 
business operations in light of its size and risk profile. State insurance regulators use RBC standards as a tool to monitor capital 
adequacy  and  to  determine  appropriate  actions  relating  to  insurers  that  show  signs  of  weak  or  deteriorating  conditions.  The 
domiciliary states of our insurance company subsidiaries have adopted laws substantially similar to the NAIC’s RBC model act. 

Fortegra’s  insurance  holding  company  is  subject  to  the  respective  state  insurance  holding  company  statutes  which  may  require 
prior regulatory approval or non-disapproval of material transactions between an insurance company and an affiliate or of a change 
in control of a domestic insurer or of payments of extraordinary dividends or distributions.

Fortegra’s insurance, service contract, and premium finance businesses are subject to U.S. federal and state regulations governing 
the  protection  of  personal  confidential  information  and  data  security,  including  the  Gramm-Leach-Bliley  Act,  New  York 
Department  of  Financial  Services  Cybersecurity  Regulation  and  California  Consumer  Privacy  Act.  Fortegra’s  subsidiaries 
operating in the EU are subject to the General Data Protection Regulation, or the “GDPR,” which regulates data protection for all 
individuals within the EU. 

Fortegra  is  active  and  subject  to  regulation  in  twenty  foreign  jurisdictions  and  intends  to  write  business  in  additional  foreign 
jurisdictions. A portion of its foreign business is conducted via our insurance company in Malta. Malta is a member country of the 
EU,  and  as  of  December  31,  2023,  Fortegra  is  active  in  eighteen  countries  in  the  EU.  The  EU’s  executive  body,  the  European 
Commission,  implemented  insurance  directives  and  capital  adequacy  and  risk  management  regulations.  EU  member  countries 
follow the insurance directives approved by the European Commission. The insurance directives set forth a regulatory regime for 
the authorization and supervision of insurers, with a broad set of principles and standards for protecting policyholders across the 
EU. 

These directives give insurers authorized in any one EU country or territory the freedom to conduct insurance business in any other 
EU country or territory, referred to as passporting. Procedures are in place regarding the notifications and approvals by the home 
state regulator for passporting. Insurers exercising this freedom continue to be regulated by their home state regulator, although the 
host state is entitled to impose domestic rules with which passporting insurers are required to follow for its business in the host 
state,  in  the  interest  of  the  general  good.  Within  this  context,  our  Malta  company  is  authorized  and  supervised  by  the  Malta 
Financial Services Authority (“MFSA”) and passports across EU member states. 

In  addition  to  the  regulation  of  authorization  and  distribution,  the  European  Commission  established  capital  adequacy  and  risk 
management regulations, called Solvency II, that apply to insurers within the EU. Solvency II includes capital requirements, risk 
management and corporate governance frameworks, and financial reporting requirements, which are subject to MFSA regulatory 
oversight.

Even  though  the  United  Kingdom  exited  the  EU,  United  Kingdom  insurance  regulation  generally  follows  the  same  insurance 
directives and Solvency II principles, with the Prudential Regulatory Authority overseeing Solvency II principles and the Financial 
Conduct  Authority  overseeing  the  market  conduct  principles  within  those  insurance  directives.  After  Brexit,  United  Kingdom 
regulators established the Temporary Permissions Regime, (TPR), which permits passporting insurers to continue operating in the 
United Kingdom for up to three years post-Brexit. Fortegra’s Malta company was passporting into the United Kingdom prior to 
Brexit and registered to operate under the TPR until its branch was granted permanent authority by United Kingdom regulators in 
July 2022. Aspects of the relationship between the United Kingdom and the EU remain to be negotiated and their relationship will 
continue  to  evolve,  including  with  respect  to  the  cross-border  provision  of  products  and  services  and  related  compliance 
requirements.  Post-transition  period  changes  to  the  EU  and  United  Kingdom  legal,  trade  and  regulatory  frameworks,  as  well  as 
changes to United Kingdom regulatory requirements for insurers operating in that host country, could increase its compliance costs 
and  subject  Fortegra  to  operational  challenges  in  the  region.  Actions  taken  by  the  prudential  regulator  and/or  conduct  regulator 
could  result  in  additional  capital  requirements  or  restrict  or  prohibit  the  sale  of  its  products,  which  would  adversely  affect 
Fortegra’s business, revenues and results of operations.

Additionally, a portion of its US and EU business is also ceded to Fortegra’s reinsurance company subsidiary domiciled in Turks 
and Caicos. Fortegra’s Turks and Caicos company is subject to Solvency II type of regulation by the domestic regulator. 

22

Fortegra is also subject to federal and state laws and regulations related to the administration of insurance products on behalf of 
other  insurers.  In  order  for  it  to  process  and  administer  insurance  products  of  other  companies,  Fortegra  is  required  to  maintain 
licenses of a third-party administrator in the states where those insurance companies operate. 

Similar to the federal and state regulations related to its insurance companies, Fortegra’s service contract companies, motor club 
companies  and  premium  and  consumer  finance  companies  are  subject  to  federal  and  state  rules  pertaining  to  authorization  to 
operate, scope of permitted benefits and terms of service, disclosures, benefits requests, cancellation and termination. For example, 
some states require that forms be filed for prior review or require that its distributors hold a license to sell. 

Employees

As of December 31, 2023, Fortegra had 1,132 employees across 25 offices in nine countries.

Tiptree Capital 

We own a diversified group of investments that are owned and managed separately as Tiptree Capital, and include our Mortgage 
segment operations. Consistent with our operating principles, we manage Tiptree Capital with a long-term focus, balancing current 
cash flow and long-term value appreciation.

We  expect  the  investments  within  Tiptree  Capital  to  change  over  time  as  we  exit  investments  and  reallocate  capital  to  new 
investment  opportunities.  Though  we  do  not  have  any  specific  sector  focus,  historically,  the  majority  of  our  investments  have 
occurred within four major sectors: asset management, real assets, specialty finance and credit investments. 

Tiptree Capital – Mortgage Operations

Our mortgage operations are conducted through Reliance First Capital, LLC. Our mortgage business has been focused on primarily 
originating  and  servicing  agency-eligible  (Federal  Housing  Administration  (“FHA”)  and  Veterans  Administration  (“VA”))  and 
conventional  and  government  loans  that  can  be  transferred  to  Ginnie  Mae  pools  or  sold  on  a  servicing-retained  or  servicing-
released basis to Fannie Mae, Freddie Mac or secondary market investors and aggregators. Revenues are primarily generated from 
gain  on  sale  income,  loan  fee  income,  servicing  fee  income,  and  net  interest  income.  The  growth  in  our  mortgage  business  is 
expected  primarily  to  come  from  increased  origination  volume,  retention  of  additional  mortgage  servicing  rights,  and  new 
products.

Competition

The residential mortgage market is highly competitive. There are a large number of institutions offering these products, including 
many  that  operate  on  a  national  scale,  as  well  as  local  savings  banks,  commercial  banks,  and  other  lenders.  Many  of  our 
competitors are larger and have access to greater financial resources. In addition, many of the largest competitors are banks or are 
affiliated with banking institutions, the advantages of which include, but are not limited to, having access to financing with more 
favorable terms, including lower interest rate bank deposits as a favorable source of funding.

Regulation

Our  mortgage  operations  are  subject  to  extensive  regulation  focused  on  consumer  protection  by  U.S.  federal,  state  and  local 
governmental authorities, including the New York Department of Financial Services, CFPB, the Federal Trade Commission and 
various  federal  and  state  agencies  that  license,  audit  and  conduct  examinations.  Our  mortgage  operations  must  comply  with  a 
number of federal, state and local consumer protection and privacy laws including laws that apply to loan origination, fair lending, 
debt collection, use of credit reports, safeguarding of non-public personally identifiable information about customers, foreclosure 
and claims handling, investment of and interest payments on escrow balances and escrow payment features, and mandate certain 
disclosures and notices to borrowers.

Employees

As of December 31, 2023, our Mortgage operations had 338 employees.

Tiptree Capital - Other

Tiptree Capital - Other currently includes:

•

Our principal investments which include cash and cash equivalents, government bonds and select equity securities, including 
Invesque, a publicly traded real estate investment company that specializes in health care and senior living property investment 
throughout North America.

23

•

•

Our ownership of a credit oriented, special situations asset manager, Corvid Peak.

Our remaining assets in the maritime transportation sector.

Competitive Strengths

The  depth  and  breadth  of  experience  of  our  management  team  enables  us  to  source,  structure,  execute  and  manage  the  capital 
allocated to Tiptree Capital. In addition, in each of our investments, we benefit by partnering with experienced management teams 
and third-party managers, which we have hired or chosen based on their depth of experience in their respective sectors.

Competition

In the sectors in which Tiptree Capital participates, the markets are highly competitive. There are a large number of competitors 
offering similar products and services, including many that operate on an international scale, and which are often affiliated with 
major  multi-national  companies.  Many  of  these  organizations  have  substantially  more  personnel  and  greater  financial  and 
commercial resources than we do. Some of these competitors have proprietary products and distribution capabilities that may make 
it more difficult for us to compete with them. Some competitors also have greater name recognition, have managed their businesses 
for longer periods of time, have greater experience over a wider range of products or have other competitive advantages. 

Regulation

In the sectors in which Tiptree Capital participates, we are subject to extensive regulation by international, federal, state and local 
governmental  authorities,  including  the  SEC,  the  Federal  Trade  Commission,  the  EU,  the  United  Kingdom  and  various  state 
agencies. Our asset manager is registered with the SEC as an investment advisor and is subject to various federal and state laws and 
regulations and rules of various securities regulators and exchanges. These laws and regulations primarily are intended to protect 
clients and generally grant supervisory agencies broad administrative powers, including the power to limit or restrict the carrying 
on of business for failure to comply with such laws and regulations. 

Our  international  operations  and  activities  also  expose  us  to  risks  associated  with  trade  and  economic  sanctions,  prohibitions  or 
other restrictions, including environmental and cybersecurity regulations, imposed by the United States or other governments or 
organizations,  including  the  United  Nations,  the  EU  and  its  member  countries.  Under  economic  and  trade  sanctions  laws, 
governments may seek to impose modifications to, prohibitions/restrictions on business practices and activities, and modifications 
to compliance programs, which may increase compliance costs, and, in the event of a violation, may subject us to fines and other 
penalties. In our international activities, we are subject to anti-corruption, anti-bribery, anti-money laundering and similar laws and 
regulations in various jurisdictions in which we conduct business, including the U.S. Foreign Corrupt Practices Act and the U.K. 
Bribery Act 2010. 

Employees

As of December 31, 2023, Tiptree Capital - Other’s combined operations had 13 employees.

Human Capital

The success of our businesses depends on our ability to attract and retain experienced personnel and seasoned key executives who 
are knowledgeable about their industry and business. We recruit talent in diverse communities. Tiptree’s seven member board of 
directors includes two women and one underrepresented minority. Tiptree’s seven person senior management team includes two 
women and one underrepresented minority. Our talent strategy is focused on employee engagement and investments in programs to 
support  career  development,  as  well  as  recognizing  and  rewarding  performance.  An  important  element  of  our  talent  strategy  is 
succession planning and building leadership at various levels across the organization.

We strive to: 

•

Provide employee wages that are competitive and consistent with employee positions, skill levels, experience, knowledge 
and geographic location. 

• Align executives’ long-term equity compensation with stockholders’ interests by linking realizable pay with earnings and 

total stockholder return. 

•

Ensure that annual increases and incentive compensation are based on merit, which is communicated to employees at the 
time of hiring and documented through their talent management process as part of the annual review procedures and upon 
internal transfer and/or promotion. 

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•

Ensure  that  all  employees  are  eligible  for  health  insurance,  paid  and  unpaid  leaves,  and  life  and  disability/accident 
coverage as well as access to wellness programs.

The Fortegra Foundation (the “Foundation”), a non-profit corporation chaired by Fortegra’s Chief Executive Officer, Mr. Richard 
S.  Kahlbaugh,  is  a  501(c)(3)  tax-exempt  charity  committed  to  giving  back  to  its  communities  in  which  we  live  and  work.  The 
Foundation accomplishes this objective through monetary donations to local, national, and global organizations providing support 
to military families and improving the health and welfare of children and families— two primary areas of focus. For example, the 
Foundation has supported clean water initiatives in Africa and, in 2022 alone, helped build three life-changing water wells in The 
Republic of Zambia.

Fortegra  has  developed  program  that  assists  employees  in  developing  key  skills  that  enable  them  to  perform  their  jobs  and  to 
advance their careers. For example, Fortegra has a Leadership Development Program (“LDP”), an early career program designed 
to attract and develop talent. The LDP includes recent college graduates who typically rotate through several departments over a 
two-year period, with the intent of gaining a deeper understanding of Fortegra and ultimately becoming better equipped with the 
knowledge  and  experience  needed  to  excel  as  future  leaders.  Fortegra’s  N.O.W.  (Network  of  Women),  its  employee  resource 
group, works to foster a supportive and equitable environment within Fortegra. The group achieves this by providing networking 
opportunities, educational initiatives, mentoring programs, and policies that support the unique needs of women in the workforce. 
Although led by women, the programming and resources provided are available to all Fortegra employees.

We invest in our employees’ career growth and provide employees with a wide range of training and development opportunities, 
including face-to-face, virtual and self-directed learning, mentoring, external development opportunities and continuing education 
required by certain professional organizations.

AVAILABLE INFORMATION

We are required to file annual, quarterly and current reports, proxy statements and other information with the SEC. 

Our  Annual  Reports  on  Form  10-K,  Quarterly  Reports  on  Form  10-Q,  Current  Reports  on  Form  8-K,  proxy  statements  and 
amendments to those reports filed or furnished pursuant to Section 13(a) or 15(d) of the Exchange Act, are also available free of 
charge on our Internet site at www.tiptreeinc.com as soon as reasonably practicable after such reports are electronically filed with 
or furnished to the SEC. The information on our website is not, and shall not be deemed to be, a part hereof or incorporated into 
this or any of our other filings with the SEC.

Our  Investor  Relations  Department  can  be  contacted  at  Tiptree  Inc.,  660  Steamboat  Road,  2nd  Floor,  Greenwich,  Connecticut 
06830, Attn: Investor Relations, telephone: (212) 446-1400, email: IR@tiptreeinc.com.

25

Item 1A. Risk Factors

We  are  subject  to  certain  risks  and  uncertainties  in  our  business  operations  which  are  described  below.  The  risks  and 
uncertainties described below are not the only risks we face. Additional risks and uncertainties that are not presently known or are 
currently deemed immaterial may also impair our business, results of operations and financial condition. 

Risks Related to our Businesses

A portion of our assets are illiquid or have limited liquidity, which may limit our ability to sell those assets at favorable 

prices or at all and creates uncertainty in connection with valuing such assets.

Our assets include equity securities, real estate, non-controlling interests in credit assets and related equity interests which 
may be illiquid or have limited liquidity. It may be difficult for us to dispose of assets with limited liquidity rapidly, or at favorable 
prices, if at all. In addition, assets with limited liquidity may be more difficult to value and may be sold at a substantial discount or 
experience more volatility than more liquid assets. We may not be able to dispose of assets at the carrying value reflected in our 
financial  statements.  Our  results  of  operations  and  cash  flows  may  be  materially  and  adversely  affected  if  our  determinations 
regarding the fair value of our illiquid assets are materially higher than the values ultimately realized upon their disposal.

Our investment in Invesque shares is subject to market volatility.

As of December 31, 2023, we owned 16.98 million shares, or approximately 30%, of Invesque, a real estate investment 
company that specializes in health care real estate and senior living property investment throughout North America. The value of 
our  Invesque  shares  is  reported  at  fair  market  value  on  a  quarterly  basis  and  fluctuates.  A  loss  in  the  fair  market  value  of  our 
Invesque  shares  could  have  a  material  adverse  effect  on  our  financial  condition  and  results  of  operations.  To  the  extent  we 
determine to sell all or a portion of our Invesque shares, there can be no assurance that we will be able to do so on a timely basis or 
at acceptable prices. 

We operate in highly competitive markets for business opportunities and personnel, which could impede our growth 

and negatively impact our results of operations.

We  operate  in  highly  competitive  markets  for  business  opportunities  in  each  of  our  areas  of  focus.  Many  of  our 
competitors  have  financial,  personnel  and  other  resource  advantages  relative  to  us  and  may  be  better  able  to  react  to  market 
conditions. These factors may place us at a competitive disadvantage in successfully competing for future business opportunities 
and personnel, which could impede our growth and negatively impact our business, financial condition and results of operations.

Our insurance subsidiaries face competition from other specialty insurance companies, standard insurance companies and 
underwriting agencies, as well as from diversified financial services companies that are larger than we are and that have greater 
financial,  marketing,  personnel  and  other  resources  than  we  do.  Many  of  these  competitors  have  more  experience  and  market 
recognition than our insurance subsidiaries. In addition, it may be difficult or prohibitively expensive for our insurance subsidiaries 
to implement technology systems and processes that are competitive with the systems and processes of these larger companies.

In  particular,  competition  in  the  insurance  industry  is  based  on  many  factors,  including  price  of  coverage,  general 
reputation and perceived financial strength, relationships with brokers, terms and conditions of products offered, ratings assigned 
by independent rating agencies, speed of claims payment and reputation, and the experience and reputation of the members of an 
underwriting team in the particular lines of insurance they seek to underwrite. In recent years, the insurance industry has undergone 
increasing consolidation, which may further increase competition.

A  number  of  new,  proposed  or  potential  industry  or  legislative  developments  could  further  increase  competition  in  the 

insurance industry. These developments include:

•

•

an increase in capital raising by companies in the industry, which could result in new entrants to the insurance markets 
and an excess of capital in the industry; and

the  deregulation  of  commercial  insurance  lines  in  certain  states  and  the  possibility  of  federal  regulatory  reform  of  the 
insurance industry, which could increase competition from standard carriers.

Our  insurance  subsidiaries  may  not  be  able  to  continue  to  compete  successfully  in  one  or  more  insurance  markets. 
Increased  competition  in  these  markets  could  result  in  a  change  in  the  supply  and  demand  for  insurance,  affect  our  insurance 

26

subsidiaries’  ability  to  price  their  products  at  risk-adequate  rates  and  retain  existing  business,  or  underwrite  new  business  on 
favorable  terms.  If  this  increased  competition  limits  our  insurance  subsidiaries’  ability  to  transact  business,  their  results  of 
operations would be adversely affected.

Additionally, our E&S insurance operations cover risks that are typically more complex and unusual than standard risks 
and require a high degree of specialized underwriting. As a result, E&S risks do not often fit the underwriting criteria of standard 
insurance  carriers,  and  are  generally  considered  higher  risk  than  those  covered  in  the  standard  market.  If  our  underwriting  staff 
inadequately judges and prices the risks associated with the business underwritten in the E&S market, our financial results could be 
adversely impacted.

Warburg  exerts  substantial  influence  on  Fortegra,  potentially  in  a  manner  that  is  not  in  Tiptree’s  shareholders’ 

interests.

Warburg  acquired  an  approximate  24%  ownership  in  Fortegra  on  an  as  converted  basis  from  us  as  part  of  the  WP 
Transaction and has contractual consent rights over Fortegra, including but not limited to certain acquisitions or dispositions, a sale 
or  change  of  control  of  Fortegra  that  does  not  achieve  certain  thresholds,  an  initial  public  offering  that  does  not  achieve  certain 
gross proceeds thresholds, incurrence of certain indebtedness, the issuance of equity senior in right to shares of Fortegra common 
or preferred stock, or amendments to the terms thereof, affiliated or related party transactions and transactions between Fortegra 
and us, any hiring or firing of certain management of Fortegra, and any material change in the nature of the business conducted by 
Fortegra.  Warburg  would  also  have  pro  rata  representation  on  the  Fortegra  board  of  directors.  As  a  result  of  their  substantial 
ownership  in  Fortegra,  Warburg  may  exert  a  substantial  influence  on  Fortegra,  potentially  in  a  manner  that  is  not  in  Tiptree’s 
shareholder’s interests.

We are exposed to risks associated with acquiring or divesting businesses or business operations.

We  regularly  evaluate  strategic  acquisition  opportunities  for  growth.  Acquired  companies  and  operations  may  have 
unforeseen operating difficulties and may require greater than expected financial and other resources. In addition, potential issues 
associated with acquisitions could among other things, include:

•

•
•
•
•

our ability to realize the full extent of the benefits, synergies or cost savings that we expect to realize as a result 
of the completion and integration of an acquisition within the anticipated time frame, or at all; 
receipt of necessary consents, clearances and approvals in connection with the acquisition; 
diversion of management’s attention from other strategies and objectives; 
motivating, recruiting and retaining executives and key employees; and 
conforming  and  integrating  financial  reporting,  standards,  controls,  procedures  and  policies,  business  cultures 
and compensation structures. 

If  an  acquisition  is  not  successfully  completed  or  integrated  into  our  existing  operations,  our  business,  results  of 

operations and financial condition could be materially adversely effected.

We have also divested, and may in the future divest, businesses or business operations. Any divestitures may involve a 
number  of  risks,  including  the  diversion  of  management’s  attention,  significant  costs  and  expenses,  the  loss  of  customer 
relationships  and  cash  flow,  and  the  disruption  of  the  affected  business  or  business  operations.  Failure  to  timely  complete  or  to 
consummate  a  divestiture  may  negatively  affect  the  valuation  of  the  affected  business  or  business  operations  or  result  in 
restructuring charges.

We may need to raise additional capital in the future or may need to refinance existing indebtedness, but there is no 

assurance that such capital will be available on a timely basis, on acceptable terms or at all.

We may need to raise additional funds or refinance our indebtedness in order to grow our business or fund our strategy or 
acquisitions. Additional financing may not be available in sufficient amounts, if at all, or on terms acceptable to us and may be 
dilutive to existing stockholders. Additionally, any securities issued to raise such funds may have rights, preferences and privileges 
senior  to  those  of  our  existing  stockholders.  We  also  cannot  predict  the  extent  and  duration  of  future  economic  and  market 
disruptions, the impact of government interventions into the market to address these disruptions and their combined impact on our 
industries, businesses and our insurance subsidiaries’ investment portfolios. If adequate funds are not available on a timely basis, if 
at all, or on acceptable terms, our ability to expand, develop or enhance our subsidiaries’ services and products, enter new markets, 
consummate acquisitions or respond to competitive pressures could be materially limited.

The amount of statutory capital and reserve requirements applicable to our insurance subsidiaries can increase due to 

27

factors outside of our control.

Our insurance subsidiaries are subject to regulation by state and, in some cases, foreign insurance authorities with respect 
to statutory capital, reserve and other requirements, including statutory capital and reserve requirements established by applicable 
insurance regulators based on RBC and Solvency II formulas. In any particular year, these requirements may increase or decrease 
depending  on  a  variety  of  factors,  most  of  which  are  outside  our  control,  such  as  the  amount  of  statutory  income  or  losses 
generated, changes in equity market levels, the value of fixed-income and equity securities in the subsidiary’s investment portfolio, 
changes in interest rates and foreign currency exchange rates, as well as changes to the RBC and Solvency II formulas used by 
insurance regulators. The laws of the various states in which our insurance subsidiaries operate establish insurance departments and 
other regulatory agencies with broad powers to preclude or temporarily suspend our insurance subsidiaries from carrying on some 
or  all  of  these  activities  or  otherwise  fine  or  penalize  our  insurance  subsidiaries  in  any  jurisdiction  in  which  we  operate.  Such 
regulation  or  compliance  could  reduce  our  insurance  subsidiaries’  profitability  or  limit  their  growth  by  increasing  the  costs  of 
compliance, limiting or restricting the products or services they sell, or the methods by which they sell services and products, or 
subject them to the possibility of regulatory actions or proceedings. Additionally, increases in the amount of additional statutory 
reserves  that  our  insurance  subsidiaries  are  required  to  hold  could  have  a  material  adverse  effect  on  our  business,  results  of 
operations, financial condition and cash flows.

Our  insurance  subsidiaries’  actual  claims  losses  may  exceed  their  reserves  for  claims,  which  may  require  them  to 
establish  additional  reserves  that  may  materially  and  adversely  affect  their  business,  results  of  operations  and  financial 
condition.

Our insurance subsidiaries maintain reserves to cover their estimated ultimate exposure for claims with respect to reported 
claims, and incurred, but not reported, claims as of the end of each accounting period. Reserves, whether calculated under GAAP 
or  statutory  accounting  principles,  do  not  represent  an  exact  calculation  of  exposure.  Instead,  they  represent  our  insurance 
subsidiaries’  best  estimates,  generally  involving  actuarial  projections,  of  the  ultimate  settlement  and  administration  costs  for  a 
claim or group of claims, based on our assessment of facts and circumstances known at the time of calculation. The adequacy of 
reserves  will  be  impacted  by  future  trends  in  claims  severity,  frequency,  judicial  theories  of  liability  and  other  factors.  These 
variables  are  affected  by  external  factors  such  as  changes  in  the  economic  cycle,  unemployment,  inflation,  judicial  trends, 
legislative  changes,  as  well  as  changes  in  claims  handling  procedures.  Many  of  these  items  are  not  directly  quantifiable, 
particularly on a prospective basis. Reserve estimates are refined as experience develops. Adjustments to reserves, both positive 
and  negative,  are  reflected  in  the  statement  of  operations  of  the  period  in  which  such  estimates  are  updated.  Because  the 
establishment of reserves is an inherently uncertain process involving estimates of future losses, we can give no assurances that 
ultimate losses will not exceed existing claims reserves. In general, future loss development could require reserves to be increased, 
which could have a material adverse effect on our insurance subsidiaries’ business, results of operations and financial condition.

Performance of our insurance subsidiaries’ investment portfolio is subject to a variety of investment risks.

Our  insurance  subsidiaries’  results  of  operations  depend  significantly  on  the  performance  of  their  investment  portfolio. 
We manage our insurance subsidiaries’ portfolio of investments along with one or more additional advisers. Such investments are 
subject to general economic conditions and market risks in addition to risks inherent to particular securities and risks relating to the 
performance of our investment advisers.

Our  primary  market  risk  exposures  are  to  changes  in  interest  rates.  See  “Management’s  Discussion  and  Analysis  of 
Financial  Condition  and  Results  of  Operations—Quantitative  and  Qualitative  Disclosures  About  Market  Risk.”  Prior  to  2022, 
interest rates had been at or near historic lows for an extended period of time. A protracted low interest rate environment places 
pressure  on  our  insurance  subsidiaries’  net  investment  income,  which,  in  turn,  would  have  a  material  adverse  effect  on  our 
profitability. During 2022 and 2023, interest rates increased rapidly and significantly, which caused a significant decrease in the 
value  of  our  fixed  income  securities,  the  majority  of  which  were  unrealized  and  recorded  in  equity.  Future  increases  in  interest 
rates could cause the values of our insurance subsidiaries’ fixed income securities portfolios to decline further, with the magnitude 
of the decline depending on the duration of securities included in our insurance subsidiaries’ portfolio and the amount by which 
interest rates increase. Some fixed income securities have call or prepayment options, which create possible reinvestment risk in 
declining rate environments. Other fixed income securities, such as mortgage-backed and asset-backed securities, carry prepayment 
risk or, in a rising interest rate environment, may not prepay as quickly as expected when purchased, which can affect the value of 
these securities and the amount and timing of cash flows therefrom.

The  value  of  our  insurance  subsidiaries’  investment  portfolio  is  also  subject  to  the  risk  that  certain  investments  may 
default or become impaired due to deterioration in the financial condition of one or more issuers of the securities our insurance 
subsidiaries’  hold,  or  due  to  deterioration  in  the  financial  condition  of  an  insurer  that  guarantees  an  issuer’s  payments  on  such 

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investments.  Downgrades  in  the  credit  ratings  of  fixed  maturities  may  also  have  a  significant  negative  effect  on  the  market 
valuation of such securities.

Such factors could reduce our insurance subsidiaries’ net investment income and result in realized investment losses. Our 
insurance  subsidiaries’  investment  portfolio  is  subject  to  increased  valuation  uncertainties  when  investment  markets  are  illiquid. 
The valuation of investments is more subjective when markets are illiquid, thereby increasing the risk that the estimated fair value 
(i.e., the carrying amount) of the securities our insurance subsidiaries’ hold in their portfolio does not reflect prices at which actual 
transactions would occur.

The performance of our insurance subsidiaries’ investments also depends heavily on our skills and those of our insurance 
subsidiaries’  other  investment  advisers,  in  analyzing,  selecting  and  managing  the  investments.  Our  insurance  subsidiaries’ 
investment policy establishes investment parameters such as maximum percentages of investment in certain types of securities and 
minimum  levels  of  credit  quality  and  is  designed  to  manage  investment  risk.  Achievement  of  our  insurance  subsidiaries’ 
investment objectives will depend, in part, on our ability and other investment advisers’ ability to provide competent, attentive and 
efficient services to our insurance subsidiaries’ portfolio under the terms of the respective investment management agreement and 
to successfully manage their investment risk. There can be no assurance that, over time, we or our insurance subsidiaries’ other 
investment advisers will be able to provide services on that basis or that we or they will be able to invest such assets on attractive 
terms  or  generate  any  investment  returns  for  stockholders  or  avoid  investment  losses.  Our  insurance  subsidiaries’  investment 
objectives  may  not  be  achieved  and  results  may  vary  substantially  over  time.  In  addition,  although  we  and  our  insurance 
subsidiaries’ other investment advisers seek to employ investment strategies that are not correlated with our insurance subsidiaries’ 
insurance and reinsurance exposures, losses in their investment portfolio may occur at the same time as underwriting losses.

The performance of our insurance subsidiaries’ investment portfolio is highly dependent on the financial and managerial 
experience of certain investment professionals associated with our insurance subsidiaries’ investment advisers, none of whom are 
under any contractual obligation to our insurance subsidiaries to continue to be associated with such investment advisers. The loss 
of  one  or  more  of  these  individuals  could  have  a  material  adverse  effect  on  the  performance  of  our  insurance  subsidiaries’ 
investment portfolio.

A shift in our insurance subsidiaries’ investment strategy could increase the riskiness of our insurance subsidiaries’ 

investment portfolio and the volatility of our results, which, in turn, may have a material adverse effect on our profitability.

Our insurance subsidiaries’ investment strategy has historically been largely focused on fixed income securities which are 
subject to less volatility but also lower returns as compared to certain other asset classes. In the future, our insurance subsidiaries’ 
investment  strategy  may  include  a  greater  focus  on  investments  in  equity  securities,  which  are  subject,  among  other  things,  to 
changes in value that may be attributable to market perception of a particular issuer or to general stock market fluctuations that 
affect all issuers. Investments in equity securities may be more volatile than investments in other asset classes such as fixed income 
securities. Common stocks generally subject their holders to more risks than preferred stocks and debt securities because common 
stockholders’ claims are subordinated to those of holders of preferred stocks and debt securities upon the bankruptcy of the issuer. 
An increase in the riskiness of our insurance subsidiaries’ investment portfolio could lead to volatility of our results, which, in turn, 
may have a material adverse effect on our profitability.

Our insurance subsidiaries could be forced to sell investments to meet their liquidity requirements.

Our insurance subsidiaries invest a portion of the premiums they receive from their insureds until they are needed to pay 
policyholder claims. Consequently, our insurance subsidiaries seek to manage the duration of their investment portfolio based on 
the  duration  of  their  losses  and  loss  adjustment  expenses  reserves  to  ensure  sufficient  liquidity  and  avoid  having  to  liquidate 
investments  to  fund  claims.  Risks  such  as  inadequate  losses  and  loss  adjustment  expenses  reserves  or  unfavorable  trends  in 
litigation could potentially result in the need to sell investments to fund these liabilities. Our insurance subsidiaries may not be able 
to sell their investments at favorable prices or at all. Sales could result in significant realized losses depending on the conditions of 
the general market, interest rates and credit issues with individual securities.

Cybersecurity attacks, technology breaches or failures of our or our third-party service providers’ information systems 
could disrupt our various business operations and could result in the loss of critical and personally identifiable information, 
which could result in the loss of reputation and customers, reduce profitability, subject our businesses to fines, penalties and 
litigation and have a material adverse effect on our business’s results of operation, financial condition and cash flows. 

Tiptree’s  businesses  are  highly  dependent  upon  the  effective  operation  of  their  information  systems  and  those  of  their 
third-party service providers and their ability to collect, use, store, transmit, retrieve and otherwise process personally identifiable 

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information and other data, manage significant databases and expand and upgrade their information systems. Our businesses rely 
on these systems for a variety of functions, including marketing and selling their products and services, performing their services, 
managing their operations, processing claims and applications, providing information to customers, performing actuarial analyses 
and maintaining financial records. Some of these systems may include or rely on third-party systems not located on their premises 
or  under  their  control.  The  interruption  or  loss  of  their  information  processing  capabilities,  or  those  of  their  third-party  service 
providers,  through  cybersecurity  attacks,  computer  hacks,  theft,  malicious  software,  phishing,  employee  error,  ransomware, 
malware, denial-of-service attacks, social engineering, viruses, worms, other malicious software programs, the loss of stored data, 
programming  errors,  the  breakdown  or  malfunctioning  of  computer  equipment  or  software  systems,  telecommunications  and 
electrical failure or damage caused by weather or natural disasters, war, catastrophes, terrorist attacks, industrial accidents or any 
other significant disruptions or security breaches could harm our businesses by hampering their ability to generate revenues and 
could negatively affect their partner relationships, competitive position and reputation.

In addition, our business’s information systems may be vulnerable to physical or electronic intrusions, computer viruses 
or  other  attacks  which  could  disable  their  information  systems  and  their  security  measures  may  not  prevent  such  attacks.  Such 
information  systems  are  additionally  vulnerable  to  security  incidents  from  inadvertent  or  intentional  actions  by  our  employees, 
third-party  vendors,  contractors,  consultants,  business  partners,  or  other  third  parties,  or  from  cyberattacks  by  malicious  third 
parties. There are numerous and evolving risks to cybersecurity and privacy from cyber threat actors, including criminal hackers, 
state-sponsored  intrusions,  industrial  espionage  and  employee  malfeasance.  There  is  also  a  potential  heightened  risk  of 
cybersecurity  incidents  as  a  result  of  geopolitical  events  outside  of  our  control,  such  as  the  ongoing  Russia-Ukraine  conflict,  as 
well  as  other  geographical  conflicts.  Global  cybersecurity  threats  can  range  from  uncoordinated  individual  attempts  to  gain 
unauthorized  access  to  our  IT  systems  and  those  of  our  business  partners  or  third-party  service  providers  to  sophisticated  and 
targeted  measures  known  as  advanced  persistent  threats.  These  cyber  threat  actors  are  becoming  more  sophisticated  and 
coordinated  in  their  attempts  to  access  IT  systems  and  data,  including  the  IT  systems  of  cloud  providers  and  third  parties  with 
whom our businesses conduct or may conduct business. Although our businesses devote significant resources to prevent, detect, 
address  and  mitigate  unwanted  intrusions  and  other  threats  and  protect  their  systems  and  data,  whether  such  data  is  housed 
internally or by external third parties, such internal controls may not be adequate or successful in protecting against all security 
breaches  and  cybersecurity  attacks,  social-engineering  attacks,  computer  break-ins,  theft  and  other  improper  activity.  Our 
businesses have experienced immaterial cybersecurity incidents and they and their third-party service providers will likely continue 
to experience cybersecurity incidents of varying degrees. Because the techniques used to obtain unauthorized access or to sabotage 
systems change frequently, generally are not recognized until launched against a target and can originate from a wide variety of 
sources,  our  businesses  and  the  third  parties  with  whom  they  do  business  may  be  unable  to  anticipate  these  techniques  or  to 
implement  adequate  preventative  measures  effective  against  all  such  security  threats.  With  the  increasing  frequency  of  cyber-
related  fraud  to  obtain  inappropriate  payments  and  other  threats  related  to  cybersecurity  attacks,  our  businesses  may  find  it 
necessary  to  expend  resources  to  remediate  cyber-related  incidents  or  to  enhance  and  strengthen  their  cybersecurity.  Such 
remediation efforts may not be successful and could result in interruptions, delays or cessation of service.

Our businesses have also implemented physical, administrative and logical security systems with the intent of maintaining 
the physical security of their facilities and systems and protecting their and their customers’ confidential and personally identifiable 
information  against  unauthorized  access  through  their  information  systems  or  by  other  electronic  transmission  or  through 
misdirection, theft or loss of data. Despite such efforts, they have in the past, and may in the future, be subject to a breach of their 
security systems that results in unauthorized access to their facilities or the information they are trying to protect. Anyone who is 
able to circumvent their security measures or those of their third-party service providers and penetrate their information systems 
could  access,  view,  misappropriate,  alter,  destroy,  misuse  or  delete  any  information  in  such  systems,  including  personally 
identifiable  information  and  proprietary  business  information  (their  own  or  that  of  third  parties)  or  compromise  of  their  control 
networks or other critical systems and infrastructure, resulting in disruptions to their business operations or access to their financial 
reporting systems. While our businesses have implemented business contingency plans and other reasonable plans to protect their 
systems,  sustained  or  repeated  system  failures  or  service  denials  could  severely  limit  their  ability  to  write  and  process  new  and 
renewal business, provide customer service or otherwise operate in the ordinary course of business. In addition, most states require 
that customers be notified if a security breach results in the disclosure of personally identifiable customer information and the trend 
toward general public notification of such incidents could exacerbate the harm to our companies’ business, financial condition and 
results of operations. Any failure, interruption or compromise of the security of our business’s information systems or those of their 
third-party  service  providers  that  result  in  inappropriate  disclosure  of  such  information  could  result  in,  among  other  things, 
significant financial losses, unfavorable publicity and damage to their reputation, governmental inquiry and oversight, difficulty in 
marketing their services, loss of customers, significant civil and criminal liability related to legal or regulatory violations, litigation 
and  the  incurrence  of  significant  technical,  legal  and  other  expenses,  any  of  which  may  have  a  material  adverse  effect  on  their 
business, results of operations, financial condition and cash flows. Additionally, the costs related to significant security breaches or 
disruptions  could  be  material  and  cause  our  businesses  to  incur  significant  expenses,  and  any  cybersecurity  insurance  that  our 
businesses may have in place may not cover such expenses.

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In some cases, our businesses rely on the safeguards put in place by third parties to protect against security threats. These 
third parties, including vendors that provide products and services for their operations, could also be a source of security risk to 
them  in  the  event  of  a  failure  or  a  security  incident  affecting  such  third  parties’  own  security  systems  and  infrastructure.  If  the 
information technology systems of our business’s third-party service providers become subject to disruptions or security breaches, 
our  businesses  may  have  insufficient  recourse  against  such  third  parties  and  our  businesses  may  have  to  expend  significant 
resources to mitigate the impact of such an event and to develop and implement protections to prevent future events of this nature 
from  occurring.  Our  business’s  network  of  ecosystem  partners  could  also  be  a  source  of  vulnerability  to  the  extent  their 
applications interface with our businesses, whether unintentionally or through a malicious backdoor. Our businesses do not review 
the software code included in third-party integrations in all instances. 

Our  insurance  business  is  dependent  on  independent  financial  institutions,  lenders,  distribution  partners,  agents, 
brokers and retailers for distribution of its products and services, and the loss of these distribution sources, or their failure to 
sell our insurance business’s products and services could materially and adversely affect its business, results of operations and 
financial condition and cash flows.

Our insurance business is dependent on independent financial institutions, lenders, distribution partners, agents, brokers 
and  retailers  to  distribute  its  products  and  services  and  its  revenue  is  dependent  on  the  level  of  business  conducted  by  such 
distributors as well as the effectiveness of their sales efforts, each of which is beyond our insurance business’s control because such 
distributors  typically  do  not  have  any  minimum  performance  or  sales  requirements.  Further,  although  its  program  arrangements 
with these distributors can be exclusive, they can be canceled on relatively short notice. Therefore, our insurance business’s growth 
is dependent, in part, on its ability to identify and attract new distribution relationships and successfully integrate its information 
systems  with  those  of  its  new  distributors.  The  impairment  of  our  insurance  business’s  distribution  relationships,  the  loss  of  a 
significant  number  of  its  distribution  relationships,  the  failure  to  establish  new  distribution  relationships,  the  failure  to  offer 
increasingly competitive products, the increase in sales of competitors’ services and products by these distributors or the decline in 
distributors’ overall business activity or the effectiveness of their sales of our insurance business’s products could materially reduce 
our  insurance  business’s  sales  and  revenues  and  have  a  material  adverse  effect  on  its  business,  results  of  operations,  financial 
condition and cash flows.

Our  insurance  business  may  lose  distributors  or  business  as  a  result  of  consolidation  within  the  financial  services 

industry or otherwise.

There has been considerable consolidation in the financial services industry, driven primarily by the acquisition of small 
and mid-size organizations by larger entities. We expect this trend to continue. Our insurance business may lose business or suffer 
decreased revenues if one or more of its significant distributors consolidate or align themselves with other companies. While our 
insurance  business  has  not  been  materially  affected  by  consolidation  to  date,  it  may  be  affected  by  industry  consolidation  that 
occurs in the future, particularly if any of its significant clients are acquired by organizations that already possess the operations, 
services and products that it provides.

A downgrade in our insurance subsidiaries’ claims paying ability or financial strength ratings could increase policy 

surrenders and withdrawals, adversely affecting relationships with distributors and reducing new policy sales.

Participants in the insurance industry use ratings from independent ratings agencies, such as A.M. Best and KBRA, as an 
important  means  of  assessing  the  financial  strength  and  quality  of  insurers,  including  their  ability  to  pay  claims.  In  setting  its 
ratings,  A.M.  Best  and  KBRA  perform  quantitative  and  qualitative  analyses  of  a  company’s  balance  sheet  strength,  operating 
performance  and  business  profile.  A.M.  Best  financial  strength  ratings  range  from  “A++”  (Superior)  to  “F”  for  insurance 
companies  that  have  been  publicly  placed  in  liquidation.  KBRA’s  ratings  range  from  AAA  (extremely  strong)  to  R  (under 
regulatory supervision).

Currently,  A.M.  Best  has  assigned  a  financial  strength  of  “A-”  (Excellent)  (Outlook  Stable)  and  KBRA  has  assigned  a 
financial  strength  rating  of  “A–”  (Outlook  Stable)  to  our  insurance  subsidiaries.  A.M.  Best  and  KBRA  assign  ratings  that  are 
intended  to  provide  an  independent  opinion  of  an  insurance  company’s  ability  to  meet  its  obligations  to  policyholders.  These 
analyses  include  comparisons  to  peers  and  industry  standards  as  well  as  assessments  of  operating  plans,  philosophy  and 
management.  A.M.  Best  and  KBRA  periodically  review  our  insurance  subsidiaries’  financial  strength  ratings  and  may,  at  their 
discretion, revise downward or revoke their ratings based primarily on their analyses of our insurance subsidiaries’ balance sheet 
strength (including capital adequacy and loss adjustment expense reserve adequacy), operating performance and business profile. 
Other independent ratings agencies may also assign our insurance subsidiaries’ financial strength ratings in the future, and these 
ratings may be below expectations. Factors that could affect such analyses include:

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•

•

•

•

•

•

•

if our insurance subsidiaries change their business practices from their organizational business plan in a manner that no 
longer supports A.M. Best’s or KBRA’s ratings;

if unfavorable financial, regulatory or market trends affect our insurance subsidiaries, including excess market capacity;

if our insurance subsidiaries’ losses exceed their loss reserves;

if our insurance subsidiaries have unresolved issues with government regulators;

if our insurance subsidiaries are unable to retain their senior management or other key personnel;

if our insurance subsidiaries’ investment portfolio incurs significant losses; or

if A.M. Best or KBRA alters its capital adequacy assessment methodology in a manner that would adversely affect our 
insurance subsidiaries’ ratings.

These and other factors could result in a downgrade of our insurance subsidiaries’ financial strength ratings. A downgrade 

or withdrawal of our insurance subsidiaries’ ratings could result in any of the following consequences, among others:

•

•

•

causing  our  insurance  subsidiaries’  current  and  future  distribution  partners  and  insureds  to  choose  other,  more  highly-
rated competitors;

increasing the cost or reducing the availability of reinsurance to our insurance subsidiaries; or

severely limiting or preventing our insurance subsidiaries from writing new and renewal insurance contracts.

In addition, in view of the earnings and capital pressures experienced by many financial institutions, including insurance 
companies,  it  is  possible  that  rating  organizations  will  heighten  the  level  of  scrutiny  that  they  apply  to  such  institutions,  will 
increase the frequency and scope of their credit reviews, will request additional information from the companies that they rate or 
will increase the capital and other requirements employed in the rating organizations’ models for maintenance of certain ratings 
levels. We can offer no assurance that our insurance subsidiaries’ ratings will remain at their current levels. It is possible that such 
reviews of our insurance subsidiaries may result in adverse ratings consequences, which could have a material adverse effect on 
our insurance subsidiaries’ business, results of operations, financial condition and cash flows.

If market conditions cause reinsurance to be more costly or unavailable, our insurance subsidiaries may be required to 

bear increased risks or reduce the level of their underwriting commitments.

Our  insurance  subsidiaries’  reinsurance  facilities  are  generally  subject  to  annual  renewal.  They  may  not  be  able  to 
maintain their current reinsurance facilities and their customers may not be able to continue to operate their captive reinsurance 
companies.  As  a  result,  even  where  highly  desirable  or  necessary,  they  may  not  be  able  to  obtain  other  reinsurance  facilities  in 
adequate amounts and at favorable rates. If our insurance subsidiaries are unable to renew their expiring facilities or to obtain or 
structure new reinsurance facilities, either their net exposures would increase or, if they are unwilling to bear an increase in net 
exposures,  they  may  have  to  reduce  the  level  of  their  underwriting  commitments.  Either  of  these  potential  developments  could 
have a material adverse effect on their business, results of operations, financial condition and cash flows.

Our insurance subsidiaries’ failure to accurately pay claims in a timely manner could have a material adverse effect 

on their business, results of operations, financial condition and cash flows.

Our insurance subsidiaries must accurately and timely evaluate and pay claims that are made under their policies. Many 
factors affect their ability to pay claims accurately and timely, including the training and experience of their claims representatives, 
including their distribution partners, the effectiveness of their management, and their ability to develop or select and implement 
appropriate procedures and systems to support their claims functions and other factors. Their failure to pay claims accurately and 
timely could lead to regulatory and administrative actions or material litigation, undermine their reputation in the marketplace and 
have  a  material  adverse  effect  on  their  business,  financial  condition,  results  of  operations  and  cash  flows.  In  addition,  if  our 
insurance subsidiaries do not manage their distribution partners effectively, or if their distribution partners are unable to effectively 
handle their volume of claims, their ability to handle an increasing workload could be adversely affected. In addition to potentially 
requiring that growth be slowed in the affected markets, our insurance subsidiaries’ business could suffer from decreased quality of 
claims work which, in turn, could have a material adverse effect on their operating margins.

Our  insurance  subsidiaries  may  incur  losses  if  reinsurers  are  unwilling  or  unable  to  meet  their  obligations  under 

reinsurance contracts.

Our insurance subsidiaries use reinsurance to reduce the severity and incidence of claims costs, and to provide relief with 

32

regard  to  certain  reserves.  Under  these  reinsurance  arrangements,  other  insurers  assume  a  portion  of  our  losses  and  related 
expenses; however, we remain liable as the direct insurer on all risks reinsured. Consequently, reinsurance arrangements do not 
eliminate our obligation to pay claims and we assume credit risk with respect to our ability to recover amounts due from reinsurers. 
The  inability  or  unwillingness  of  any  reinsurer  to  meet  its  financial  obligations  could  negatively  affect  our  business,  results  of 
operations,  financial  condition  and  cash  flows.  As  credit  risk  is  generally  a  function  of  the  economy,  our  insurance  subsidiaries 
face  a  greater  credit  risk  in  an  economic  downturn.  While  our  insurance  subsidiaries  attempt  to  manage  credit  risks  through 
underwriting guidelines, collateral requirements and other oversight mechanisms, their efforts may not be successful. For example, 
to  reduce  such  credit  risk,  our  insurance  subsidiaries  require  certain  third  parties  to  post  collateral  for  some  or  all  of  their 
obligations  to  them.  In  cases  where  our  insurance  subsidiaries  receive  letters  of  credit  from  banks  as  collateral  and  one  of  their 
counterparties is unable to honor its obligations, our insurance subsidiaries are exposed to the credit risk of the banks that issued 
the letters of credit.

New lines of business, new products and services or new geographic markets may subject our insurance subsidiaries to 

additional risks.

From  time  to  time,  our  insurance  subsidiaries  may  implement  new  lines  of  business,  offer  new  products  and  services 
within existing lines of business, or expand into new geographic markets. In addition, our insurance subsidiaries will continue to 
make  investments  in  development  and  marketing  for  new  products  and  services.  There  are  substantial  risks  and  uncertainties 
associated with these efforts. In developing and marketing new lines of business, new products or services and/or expansions into 
new  geographic  markets,  our  insurance  subsidiaries  may  invest  significant  time  and  resources.  Initial  timetables  for  the 
development and introduction of new lines of business and/or new products or services and/or expansions into new geographies, 
may  not  be  achieved  and  price  and  profitability  targets  may  not  prove  feasible.  Furthermore,  new  lines  of  business  and/or  new 
product or service offerings may not gain market acceptance. Our insurance subsidiaries also may not gain market acceptance in 
new geographies. External factors, such as compliance with regulations, competitive alternatives, and shifting market preferences, 
may also impact the successful implementation of a new line of business or a new product or service. Furthermore, the burden on 
management  and  our  insurance  subsidiaries’  IT  of  introducing  any  new  line  of  business  or  new  product  or  service  and/or  new 
geographic market could have a significant impact on the effectiveness of their system of internal controls. Failure to successfully 
manage  these  risks  in  the  development  and  implementation  of  new  lines  of  business  or  new  products  or  services  could  have  a 
material adverse effect on our insurance subsidiaries’ business, financial condition, results of operations and cash flows.

If our insurance subsidiaries fail to manage future growth effectively, their business, results of operations, financial 

condition and cash flows would be harmed.

Our  insurance  subsidiaries  have  expanded  their  operations  significantly  and  anticipate  that  further  expansion  will  be 
required  in  order  for  them  to  significantly  grow  their  business.  In  particular,  they  may  require  additional  capital,  systems 
development and skilled personnel. Their growth has placed and may continue to place increasing and significant demands on their 
management,  operational  and  financial  systems  and  infrastructure  and  their  other  resources.  If  our  insurance  subsidiaries  do  not 
effectively manage their growth, the quality of their services could suffer, which could harm their business, results of operations, 
financial condition and cash flows. In order to manage future growth, they may need to hire, integrate and retain highly skilled and 
motivated employees. Our insurance subsidiaries may not be able to hire new employees quickly enough to meet their needs. If 
they fail to effectively manage their hiring needs and successfully integrate new hires, their efficiency and their employee morale, 
productivity  and  retention  could  suffer,  and  their  business,  results  of  operations,  financial  condition  and  cash  flows  could  be 
harmed.  They  may  also  be  required  to  continue  to  improve  their  existing  systems  for  operational  and  financial  management, 
including their reporting systems, procedures and controls. These improvements may require significant capital expenditures and 
place  increasing  demands  on  their  management.  They  may  not  be  successful  in  managing  or  expanding  their  operations  or  in 
maintaining  adequate  financial  and  operating  systems  and  controls.  If  they  do  not  successfully  implement  any  required 
improvements in these areas, their business, results of operations, financial condition and cash flows could be harmed.

The effects of emerging claim and coverage issues on our insurance subsidiaries’ business are uncertain.

As  industry  practices  and  economic,  legal,  judicial,  social  and  other  environmental  conditions  change,  unexpected  and 
unintended issues related to claims and coverage may emerge. These issues may have a material adverse effect on our insurance 
subsidiaries’ business by either extending coverage beyond their underwriting intent or by increasing the number or size of claims. 
In  some  instances,  these  emerging  issues  may  not  become  apparent  for  some  time  after  they  have  issued  the  affected  insurance 
policies. As a result, the full extent of liability under their insurance policies may not be known until many years after the policies 
are  issued.  In  addition,  the  potential  passage  of  new  legislation  designed  to  expand  the  right  to  sue,  to  remove  limitations  on 
recovery, to extend the statutes of limitations or otherwise to repeal or weaken tort reforms could have an adverse impact on their 

33

business. The effects of these and other unforeseen emerging claim and coverage issues are difficult to predict and could harm their 
business and have a material adverse effect on their results of operations.

Our  insurance  subsidiaries’  international  operations  expose  them  to  investment,  political  and  economic  risks, 

including foreign currency and credit risk.

Our insurance subsidiaries’ expanding international operations in the United Kingdom, continental Europe and the Asia-
Pacific region, expose them to increased investment, political and economic risks, including foreign currency exchange rate risk 
with certain assets and liabilities, and credit risk. Changes in the value of the U.S. dollar relative to the value of the British Pound 
Sterling, Euro and other currencies in the jurisdictions in which they operate could have a material adverse effect on their business, 
results  of  operations,  financial  condition  and  cash  flows.  Their  investments  in  non-U.S.-denominated  assets  are  subject  to 
fluctuations in non-U.S. securities and currency markets, and those markets can be volatile. Non-U.S. currency fluctuations also 
affect the value of any dividends paid by their non-U.S. subsidiaries to their parent companies in the United States.

Our  insurance  subsidiaries  use  AI,  machine  learning  and  statistical  models  to  assist  their  decision-making  in  key 
areas, such as underwriting, claims, reserving, and catastrophe risk, but actual results could differ materially from the model 
outputs and related analyses. 

Our  insurance  subsidiaries  use  various  modeling  techniques,  including  Stochastic,  Bayesian  statistics,  classification, 
regression, clustering and other advanced machine learning techniques along with data analytics to analyze and estimate loss trends 
and other risks associated with their underwriting and claims operations. Our insurance subsidiaries use the modeled outputs and 
related analyses to assist them in certain decisions involving underwriting, pricing, claims, reserving, reinsurance, and catastrophe 
risk.  As  with  many  technological  innovations,  AI  and  machine  learning  present  risks  and  challenges  that  could  affect  their 
adoption,  and  therefore  our  insurance  subsidiaries’  business.  The  assumptions  used  in  deriving  modeled  outputs  and  related 
analyses  are  subject  to  uncertainties,  model  errors  and  the  limitations  of  historical  internal  and  industry  data.  In  addition,  the 
modeled outputs and related analyses may from time to time contain inaccuracies, which could have a material adverse effect on 
our  insurance  subsidiaries’  results  of  operations,  if,  based  upon  these  models,  they  misprice  their  products,  underestimate  the 
frequency  and/or  severity  of  loss  events,  or  overestimate  the  risks  they  are  exposed  to.  Persistent  inaccuracies  may  adversely 
impact new business growth and retention of our insurance subsidiaries’ existing clients which could have a material adverse effect 
on our insurance subsidiaries’ results of operations and financial condition.

Additionally,  there  are  significant  risks  involved  in  developing  and  deploying  AI,  such  as  an  increase  in  intellectual 
property  infringement  or  misappropriation,  data  privacy,  cybersecurity,  operational  and  technological  risks,  harmful  content, 
accuracy, bias, toxicity and discrimination, any of which could affect our insurance subsidiaries’ further development, adoption, 
and  use  of  AI,  and  may  cause  them  to  incur  additional  research  and  development  costs  to  resolve  such  issues.  In  addition,  no 
assurance  can  be  provided  that  the  usage  of  such  AI  will  enhance  our  insurance  subsidiaries’  business  or  assist  in  being  more 
efficient  or  profitable.  The  introduction  of  AI  technologies  into  new  or  existing  products  may  result  in  new  or  enhanced 
governmental or regulatory scrutiny, litigation, confidentiality or security risks, ethical concerns, or other complications that could 
adversely affect our insurance subsidiaries’ results of operations and financial condition. It is not possible to predict all of the risks 
related to the use of AI, and changes in laws, rules, directives and regulations governing AI may adversely affect our insurance 
subsidiaries’ ability to develop and use AI or subject them to legal liability.

Our businesses could be adversely affected by the loss of one or more key executives or by an inability to attract and 

retain qualified personnel.

The  success  of  our  businesses  depend  on  their  ability  to  attract  and  retain  experienced  personnel  and  seasoned  key 
executives who are knowledgeable about their industry and business. The pool of talent from which they actively recruit is limited 
and may fluctuate based on market dynamics specific to their industry and independent of overall economic conditions. As such, 
higher  demand  for  employees  having  the  desired  skills  and  expertise  could  lead  to  increased  compensation  expectations  for 
existing  and  prospective  personnel,  making  it  difficult  for  them  to  retain  and  recruit  key  personnel  and  maintain  labor  costs  at 
desired levels. Should any of their key executives cease to be employed by them, or if they are unable to retain and attract talented 
personnel,  they  may  be  unable  to  maintain  their  current  competitive  position  in  the  specialized  markets  in  which  they  operate, 
which could have a material adverse effect on their results of operations.

Our insurance subsidiaries’ continued growth depends in part on their ability to continue to grow their customer base.

Increasing  the  customer  base  of  our  insurance  subsidiaries  will  depend,  to  a  significant  extent,  on  their  ability  to 
effectively expand their sales and marketing activities, as well as their partner ecosystem and other customer referral sources. They 

34

may not be able to recruit qualified sales and marketing personnel, train them to perform and achieve an acceptable level of sales 
production from them on a timely basis or at all. If our insurance subsidiaries are unable to maintain effective sales and marketing 
activities and maintain and expand their partner network, their ability to attract new customers could be harmed and their business, 
results of operations, financial condition and cash flows would suffer.

Our  insurance  subsidiaries  may  not  be  able  to  effectively  start  up  or  integrate  new  program  opportunities,  and  they 

may invest in new program opportunities or initiatives that are ultimately unsuccessful.

Our  insurance  subsidiaries’  ability  to  grow  their  business  depends,  in  part,  on  their  creation,  implementation  and 
acquisition of new insurance programs that are profitable and fit within their business model. New program launches as well as 
resources  to  integrate  business  acquisitions  are  subject  to  many  obstacles,  including  ensuring  they  have  sufficient  business  and 
systems processes, determining appropriate pricing, obtaining reinsurance, assessing opportunity costs and regulatory burdens and 
planning  for  internal  infrastructure  needs.  If  they  cannot  accurately  assess  and  overcome  these  obstacles  or  they  improperly 
implement new insurance programs, their ability to grow profitably will be impaired. Additionally, they may be unsuccessful in 
identifying new program opportunities, or they may be unable to develop or market new programs or initiatives in a timely or cost-
effective  manner.  In  addition,  new  programs  or  initiatives  may  not  achieve  the  market  penetration  or  price  levels  necessary  for 
profitability. If they are unable to develop timely enhancements to, and new features for, their existing programs and services or if 
they  are  unable  to  develop  new  programs  and  services,  their  programs  and  services  may  become  less  marketable  and  less 
competitive, and their business, results of operations, financial condition and cash flows would be harmed.

If  our  businesses  are  unable  to  maintain  a  high  level  of  service,  their  business,  results  of  operations,  financial 

condition and cash flows may be harmed.

One of the key attributes of our various businesses is providing high quality service to their partners and customers. They 
may be unable to sustain these levels of service, which would harm their reputation and our business. Alternatively, they may only 
be  able  to  sustain  high  levels  of  service  by  significantly  increasing  their  operating  costs,  which  would  materially  and  adversely 
affect their results of operations. The level of service they are able to provide depends on their personnel to a significant extent. 
Their personnel must be well-trained in their processes and able to handle customer calls effectively and efficiently. Any inability 
of  their  personnel  to  meet  service  level  demands,  whether  due  to  absenteeism,  training,  turnover,  disruptions  at  their  facilities, 
including due to health emergencies, such as pandemics, bad weather, power outages or other reasons, could adversely impact their 
business. If they are unable to maintain high levels of service performance, their reputation could suffer and their business, results 
of operations, financial condition and cash flows would be harmed.

Our business’s results of operations have in the past varied from quarter to quarter and may not be indicative of our 

long-term prospects.

Our  business’s  results  of  operations  are  subject  to  fluctuation  and  have  historically  varied  from  quarter  to  quarter.  We 
expect  our  quarterly  results  to  continue  to  fluctuate  in  the  future  due  to  a  number  of  factors,  including  the  general  economic 
conditions  in  the  markets  where  we  operate,  the  frequency,  occurrence  or  severity  of  catastrophic  or  other  insured  events  or 
otherwise,  fluctuating  interest  rates,  claims  exceeding  our  insurance  subsidiaries’  loss  reserves,  competition  in  the  industries  in 
which  our  subsidiaries  operate,  deviations  from  expected  renewal  rates  of  existing  policies  and  contracts,  adverse  investment 
performance and the cost of reinsurance coverage.

In particular, our insurance subsidiaries seek to underwrite products and make investments to achieve favorable returns on 
tangible stockholders’ equity over the long-term. In addition, their opportunistic nature may result in fluctuations in gross written 
premiums  from  period  to  period  as  they  concentrate  on  underwriting  contracts  that  they  believe  will  generate  better  long-term, 
rather  than  short-term,  results.  Accordingly,  their  short-term  results  of  operations  may  not  be  indicative  of  their  long-term 
prospects.

The industries in which our businesses operate are cyclical in nature.

The financial performance of the insurance industry has historically fluctuated with periods of lower premium rates and 
excess underwriting capacity resulting from increased competition (a “soft market”) followed by periods of higher premium rates 
and reduced underwriting capacity resulting from decreased competition (a “hard market”). Soft markets occur when the supply of 
insurance capital in a given market or territory is greater than the amount of insurance coverage demanded by all potential insureds 
in  that  market.  When  this  occurs,  insurance  prices  tend  to  decline  and  policy  terms  and  conditions  become  more  favorable  to 
insureds. Conversely, hard markets occur when there is not enough insurance capital capacity in the market to meet the needs of 
potential insureds, causing insurance prices to generally rise and policy terms and conditions to become more favorable to insurers. 

35

Although  an  individual  insurance  company’s  financial  performance  depends  on  its  own  specific  business  characteristics,  the 
profitability of most P&C insurance companies tends to follow this cyclical market pattern. Further, this cyclical market pattern 
can be more pronounced in the E&S market than in the standard insurance market. When the standard insurance market hardens, 
the  E&S  market  typically  hardens,  and  growth  in  the  E&S  market  can  be  significantly  more  rapid  than  growth  in  the  standard 
insurance market. Similarly, when conditions begin to soften, many customers that were previously driven into the E&S market 
may return to the admitted carrier market, exacerbating the effects of rate decreases. Some of our insurance subsidiaries’ specialty 
programs  are  exposed  to  these  hard  and  soft  market  cycles.  Our  insurance  subsidiaries’  business  generally  impacted  by  P&C 
commercial  market  cycles  is  primarily  reported  in  their  property  and  short-tail,  general  liability  and  professional  liability  lines. 
Across these lines, they manage various multiline and monoline programs that are impacted in different ways by market cycles. 
Currently, our insurance subsidiaries believe the following specialty programs and lines of business are in, to varying degrees, a 
hard market: programs in the property and short-tail lines; within general liability line of business, contractors, excess liability and 
manufactured home parks programs; and programs in the professional liability line of business. Our insurance subsidiaries seek to 
limit  the  potential  impact  of  these  trends  through  their  underwriting  process  that  includes,  but  is  not  limited  to,  maintaining  a 
diverse book of business with exposures to various lines, and products, limiting their risk exposures through reinsurance, carefully 
crafting their underwriting guidelines and monitoring how their distribution partners adhere to those guidelines. Additionally, our 
insurance subsidiaries believe that other insurance lines, specifically personal lines and alternative risks, are not influenced by the 
hard and soft market cycles to the same degree as P&C commercial lines. 

Furthermore, adverse economic factors, including recession, inflation, periods of high unemployment or lower economic 
activity, could result in the sale of fewer policies than expected or an increase in the frequency of claims and premium defaults, and 
even the falsification of claims, or a combination of these effects, which, in turn, could affect our insurance subsidiaries’ growth 
and  profitability.  In  an  economic  downturn  that  is  characterized  by  higher  unemployment,  declining  spending  and  reduced 
corporate revenue, the demand for insurance products is generally adversely affected, which directly affects their premium levels 
and profitability. Negative economic factors may also affect their ability to receive the appropriate rate for the risk they insure with 
their policyholders and may adversely affect the number of policies they can write, and their opportunities to underwrite profitable 
business.  In  an  economic  downturn,  our  insurance  subsidiaries’  customers  may  have  less  need  for  insurance  coverage,  cancel 
existing  insurance  policies,  modify  their  coverage  or  not  renew  their  policies.  Existing  policyholders  may  exaggerate  or  even 
falsify claims to obtain higher claims payments. Some of our insurance subsidiaries’ lines of business that provide reconstruction, 
replacement or repair benefits may be negatively affected by higher rates for labor or the cost of replacement parts, and they have 
also experienced temporarily higher claims severities, in particular for their service contracts lines of business. In addition, high 
inflation may impact the creditworthiness of reinsurers and counterparties that our insurance subsidiaries contract with, which may 
negatively impact the ability of such parties to make timely payments pursuant to our insurance subsidiaries’ contracts with them. 
These  outcomes  would  reduce  their  underwriting  profit  to  the  extent  these  factors  are  not  reflected  in  the  rates  they  charge, 
including to the extent their distribution partners are unable or unwilling to effectively implement pricing or coverage to mitigate 
these impacts.

The  financial  performance  of  the  mortgage  segment  largely  depends  on  the  health  of  the  U.S.  residential  real  estate 
industry, which is seasonal, cyclical, and affected by changes in general economic conditions beyond our control. Economic factors 
such as increased interest rates, slow economic growth or recessionary conditions, the pace of home price appreciation or the lack 
of it, changes in household debt levels, and increased unemployment or stagnant or declining wages affect our clients’ income and 
thus  their  ability  and  willingness  to  make  loan  payments.  National  or  global  events  affect  all  such  macroeconomic  conditions. 
Weak or a significant deterioration in economic conditions reduce the amount of disposable income consumers have, which in turn 
reduces consumer spending and the willingness of qualified potential clients to take out loans. As a result, such economic factors 
affect loan origination volume.

If  our  insurance  subsidiaries  are  not  able  to  maintain  and  enhance  their  brand,  their  business  and  results  of 
operations  will  be  harmed.  Damage  to  their  reputation  and  negative  publicity  could  have  a  material  adverse  effect  on  their 
business, results of operations, financial condition and cash flows.

We believe that maintaining and enhancing our insurance subsidiaries’ brand identity is critical to their relationships with 
their existing customers and partners and to their ability to attract new customers and partners. They also intend to grow their brand 
awareness among consumers and potential program partners in order to further expand their reach and attract new customers and 
program partners. The promotion of their brand in these and other ways may require them to make substantial investments and it is 
anticipated that, as their market becomes increasingly competitive, these branding initiatives may become increasingly difficult and 
expensive.  Our  insurance  subsidiaries’  brand  promotion  activities  may  not  be  successful  or  yield  increased  revenue,  and  to  the 
extent that these activities yield increased revenue, the increased revenue may not offset the expenses they incur and their results of 
operations could be harmed. If they do not successfully maintain and enhance their brand, their business may not grow and they 
could  lose  their  relationships  with  customers  or  partners,  which  would  harm  their  business,  results  of  operations,  financial 
condition and cash flows.

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Our insurance subsidiaries may be adversely affected by negative publicity relating to brand and activities. For instance, if 
their brand receives negative publicity, the number of customers visiting their platforms could decrease, and their cost of acquiring 
customers  could  increase  as  a  result  of  a  reduction  in  the  number  of  consumers  coming  from  their  direct  customer  acquisition 
channel.

Our  business’s  risk  management  policies  and  procedures  may  prove  to  be  ineffective  and  leave  them  exposed  to 
unidentified or unanticipated risk, which could adversely affect their business, results of operations, financial condition or cash 
flows.

Our  businesses  have  developed  and  continue  to  develop  enterprise-wide  risk  management  policies  and  procedures  to 
mitigate risk and loss to which they are exposed. There are, however, inherent limitations to risk management strategies because 
there may exist, or develop in the future, risks that they have not appropriately anticipated or identified. If their risk management 
policies  and  procedures  are  ineffective,  they  may  suffer  unexpected  losses  and  could  be  materially  adversely  affected.  As  their 
business changes and the markets in which they operate evolve, their risk management framework may not evolve at the same pace 
as  those  changes.  As  a  result,  there  is  a  risk  that  new  products  or  new  business  strategies  may  present  risks  that  are  not 
appropriately identified, monitored or managed. In times of market stress, unanticipated market movements or unanticipated claims 
experience, the effectiveness of their risk management strategies may be limited, resulting in losses to them. In addition, there can 
be  no  assurance  that  they  can  effectively  review  and  monitor  all  risks  or  that  all  of  their  employees  will  follow  their  risk 
management policies and procedures.

Moreover, state legislatures and regulators have increased their focus on risks within an insurer’s holding company system 
that  may  pose  enterprise  risk  to  insurers  and  within  mortgage  originators  that  may  pose  risk  to  borrowers.  Our  insurance  and 
mortgage  subsidiaries  operate  within  an  enterprise  risk  management  (“ERM”)  framework  designed  to  assess  and  monitor  their 
risks. However, there can be no assurance that they can effectively review and monitor all risks, or that all of their employees will 
operate within the ERM framework or that their ERM framework will result in their accurately identifying all risks and accurately 
limiting their exposures based on our business’s assessments.

Our insurance subsidiaries may not be able to generate sufficient cash to service all of their indebtedness and may be 

forced to take other actions to satisfy their obligations under their indebtedness, which may not be successful.

Our  insurance  subsidiaries’  ability  to  make  scheduled  payments  on  or  refinance  their  debt  obligations  depends  on  their 
financial condition and operating performance, which are subject to prevailing economic and competitive conditions and to certain 
financial, business, legislative, regulatory and other factors beyond their control. They may be unable to maintain a level of cash 
flows from operating activities sufficient to permit us to pay the principal and interest on their indebtedness.

If their cash flows and capital resources are insufficient to fund their debt service obligations, they could face substantial 
liquidity problems and could be forced to reduce or delay investments and capital expenditures, or to dispose of material assets or 
operations, alter their dividend policy, seek additional debt or equity capital or restructure or refinance their indebtedness. They 
may not be able to effect any such alternative measures on commercially reasonable terms or at all and, even if successful, those 
alternative  actions  may  not  allow  them  to  meet  their  scheduled  debt  service  obligations.  The  instruments  that  will  govern  their 
indebtedness may restrict their ability to dispose of assets and may restrict the use of proceeds from those dispositions and may 
also restrict their ability to raise debt or equity capital to be used to repay other indebtedness when it becomes due. They may not 
be able to consummate those dispositions or to obtain proceeds in an amount sufficient to meet any debt service obligations when 
due.

Our insurance subsidiaries’ inability to generate sufficient cash flows to satisfy their debt obligations, or to refinance their 
indebtedness  on  commercially  reasonable  terms  or  at  all,  may  materially  adversely  affect  their  business,  results  of  operations, 
financial condition and cash flows.

Restrictive covenants in the agreements governing our insurance subsidiaries’ indebtedness may restrict their ability to 

pursue their business strategies.

The agreements governing our insurance subsidiaries’ indebtedness contain a number of restrictive covenants that impose 
significant operating and financial restrictions on them and may limit their ability to pursue their business strategies or undertake 
actions that may be in their best interests. The agreements governing their indebtedness include covenants restricting, among other 
things, their ability to:

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•
•
•
•
•
•
•

incur or guarantee additional debt;
incur liens;
complete mergers, consolidations and dissolutions;
enter into transactions with affiliates;
pay dividends or other distributions;
sell certain of their assets that have been pledged as collateral; and
undergo a change in control.

A breach of the covenants under the indenture that governs our insurance subsidiaries’ 8.50% Fixed Rate Resetting Junior 
Subordinated Notes due in October 2057 (the “Notes”) and Second Amended and Restated Credit Agreement dated as of October 
21, 2022 by and among The Fortegra Group, Inc., Fortegra Financial and Lots Intermediate Co., as borrowers, Fifth Third Bank, 
N.A., as administrative agent and issuing lender could result in an event of default. Such default may result in the acceleration of 
any other debt to which a cross-acceleration or cross-default provision applies. In the event our insurance subsidiaries’ lenders or 
noteholders accelerate the repayment of their indebtedness, they and their subsidiaries may not have sufficient assets to repay that 
indebtedness. As a result of these restrictions, they may be:

•
•

unable to raise additional debt or equity financing to operate during general economic or business downturns; or
unable to compete effectively or to take advantage of new business opportunities.

These  restrictions  may  affect  their  ability  to  grow  in  accordance  with  their  strategy.  In  addition,  their  financial  results, 

substantial indebtedness and credit ratings could materially adversely affect the availability and terms of future financing.

Retentions in various lines of business expose our insurance subsidiaries to potential losses.

Our insurance subsidiaries retain risk for their own account on business underwritten by their insurance subsidiaries. The 
determination  to  reduce  the  amount  of  reinsurance  they  purchase,  or  not  to  purchase  reinsurance  for  a  particular  risk,  customer 
segment or category is based on a variety of factors, including market conditions, pricing, availability of reinsurance, their capital 
levels and their loss history. Such determinations increase their financial exposure to losses associated with such risks, customer 
segments or categories and, in the event of significant losses associated with such risks, customer segments or categories, could 
have a material adverse effect on their business, results of operations, financial condition and cash flows.

The exit of the United Kingdom from the European Union could adversely affect our insurance subsidiaries’ business.

The United Kingdom ceased to be a part of the EU on December 31, 2020 (which is commonly referred to as “Brexit”). 
Aspects of the relationship between the United Kingdom and the EU remain to be negotiated and their relationship will continue to 
evolve,  including  with  respect  to  the  cross-border  provision  of  products  and  services  and  related  compliance  requirements.  The 
effects  of  Brexit  on  our  insurance  subsidiaries’  business  will  depend  on  the  manner  in  which  it  is  implemented  and  any  other 
relevant agreements between the United Kingdom and the EU, among other factors. For example, the United Kingdom ratified a 
trade and cooperation agreement governing its future relationship with the EU. Among other things, the agreement, which became 
effective  in  mid-2021,  addresses  trade,  economic  arrangements,  law  enforcement,  judicial  cooperation  and  governance.  Because 
the agreement merely sets forth a framework in many respects that requires complex additional bilateral negotiations between the 
United Kingdom and the EU, significant uncertainty remains about how the precise terms of the relationship between the parties 
will differ from the terms before withdrawal. Because our insurance subsidiaries conduct business in both the United Kingdom and 
the EU and because they rely on their Malta insurance subsidiary’s ability to conduct business in the United Kingdom, they face 
risks associated with the uncertainty and disruptions relating to Brexit, including the risk of additional regulatory and other costs 
and  challenges  and/or  limitations  on  their  ability  to  sell  particular  products  and  services.  As  a  result,  the  ongoing  uncertainty 
surrounding  Brexit  could  have  a  material  adverse  effect  on  their  business  (including  their  European  growth  plans),  results  of 
operations, financial condition and cash flows.

Proposed or potential industry or legislative developments in the E&S market could further increase competition in our 

insurance subsidiaries’ industry and have a material adverse effect on their premiums, underwriting results and profits.

A  number  of  new,  proposed  or  potential  industry  or  legislative  developments  could  further  increase  competition  in  the 
E&S market and have a material adverse effect on our insurance subsidiaries’ premiums, underwriting results and profits. These 
developments include:

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•

•

•

Changing distribution practices caused by the internet, including shifts in the way in which E&S insurance is purchased 
by consumers. Our insurance subsidiaries currently depend largely on distribution through third-party agents and brokers. 
If their distribution model were to be significantly altered by changes in the way E&S insurance is regulated, marketed, or 
sold including, without limitation, through the use of the internet, it could have a material adverse effect on our insurance 
subsidiaries’ premiums, underwriting results and profits;

Admitted products may be preferred from a regulatory or legislative perspective in certain jurisdictions; and 

The  market  for  E&S  as  compared  to  admitted  products  may  shift  based  on  the  availability  of  admitted  products  at 
competitive prices and consumer, agent or broker preferences, among other factors.

Due  to  the  structure  of  some  of  our  insurance  business’s  commissions,  it  is  exposed  to  risks  related  to  the 

creditworthiness of some of its independent agents and program partners.

Our insurance business is subject to the credit risk of some of the independent agents and program partners with which it 
contracts to sell its products and services. Our insurance business typically advances commissions as part of its product offerings. 
These advances are a percentage of the premiums charged. If our insurance business over-advances such commissions, the agents 
and  program  partners  may  not  be  able  to  fulfill  their  payback  obligations,  which  could  have  a  material  adverse  effect  on  our 
insurance businesses, results of operations and financial condition.

Failure of our insurance subsidiaries’ distribution partners to properly market, underwrite or administer policies could 

adversely affect our insurance subsidiaries.

The marketing, underwriting, claims administration and other administration of policies in connection with our insurance 
subsidiaries’  issuing  carrier  services  are  the  responsibility  of  their  distribution  partners.  Any  failure  by  them  to  properly  handle 
these  functions  could  result  in  liability  to  our  insurance  subsidiaries.  Even  though  their  distribution  partners  may  be  required  to 
compensate  them  for  any  such  liability,  there  are  risks  that  they  do  not  pay  them  because  such  partners  become  insolvent  or 
otherwise.  Any  such  failures  could  create  regulatory  issues  or  harm  our  insurance  subsidiaries’  reputation,  which  could  have  a 
material adverse effect on their business, results of operations, financial condition and cash flows.

Third-party vendors our businesses rely upon to provide certain business and administrative services on their behalf 
may not perform as anticipated, which could have an adverse effect on their business, results of operations, financial condition 
and cash flows.

Our businesses have taken action to reduce coordination costs and take advantage of economies of scale by transitioning 
multiple functions and services to third-party providers. They periodically negotiate provisions and renewals of these relationships, 
and  there  can  be  no  assurance  that  such  terms  will  remain  acceptable  to  us  or  such  third  parties.  If  such  third-party  providers 
experience disruptions or do not perform as anticipated, or our businesses experience problems with a transition to a third-party 
provider, they may experience operational difficulties, an inability to meet obligations (including policyholder obligations), a loss 
of business and increased costs, or suffer other negative consequences, all of which may have a material adverse effect on their 
business, results of operations, liquidity and cash flows.

Our  insurance  subsidiaries  may  act  based  on  inaccurate  or  incomplete  information  regarding  the  accounts  they 

underwrite.

Our insurance subsidiaries rely on information provided by insureds or their representatives when underwriting insurance 
policies.  While  they  may  make  inquiries  to  validate  or  supplement  the  information  provided,  they  may  make  underwriting 
decisions  based  on  incorrect  or  incomplete  information.  It  is  possible  that  they  will  misunderstand  the  nature  or  extent  of  the 
activities or facilities and the corresponding extent of the risks that they insure because of their reliance on inadequate or inaccurate 
information.

Any failure to protect or enforce our insurance subsidiaries’ intellectual property rights could impair their intellectual 
property,  technology  platform  and  brand.  In  addition,  they  may  be  sued  by  third  parties  for  alleged  infringement  of  their 
proprietary rights.

Our insurance subsidiaries’ success and ability to compete depend in part on their ability to establish, maintain, protect 
and  enforce  their  intellectual  property  and  proprietary  rights,  which  includes  their  rights  in  their  technology  platform  and  their 
brand. Our insurance subsidiaries primarily rely on a combination of intellectual property rights, such as copyrights, trade secrets 
and  trademarks,  in  addition  to  confidentiality  agreements,  procedures  and  contractual  provisions  with  their  employees,  clients, 
service  providers,  partners  and  other  third  parties  to  establish,  maintain,  protect  and  enforce  their  proprietary  or  confidential 

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information and intellectual property rights. Our insurance subsidiaries also rely on agreements under which they contract to own, 
or license rights to use, intellectual property developed by employees, contractors and other third parties. In addition, while they 
generally enter into confidentiality agreements with employees and third parties to protect their trade secrets, know-how, business 
strategy  and  other  proprietary  information,  such  confidentiality  agreements  could  be  breached  or  otherwise  may  not  provide 
meaningful protection for their trade secrets and know-how. Similarly, while they seek to enter into agreements with all of their 
employees  who  develop  intellectual  property  during  their  employment  to  assign  the  rights  in  such  intellectual  property  to  our 
insurance subsidiaries, they may fail to enter into such agreements with all relevant employees, such agreements may be breached 
or may not be self-executing, and they may be subject to claims that such employees misappropriated relevant rights from their 
previous employers.

The steps our insurance subsidiaries take to protect their intellectual property may be inadequate and despite their efforts 
to protect their proprietary rights and intellectual property, unauthorized parties may attempt to copy aspects of their solutions or to 
obtain  and  use  information  that  they  regard  as  proprietary,  and  third  parties  may  attempt  to  independently  develop  similar 
technology.  Policing  unauthorized  use  of  their  technology  and  intellectual  property  rights  may  be  difficult  and  may  not  be 
effective. 

Litigation brought to protect and enforce their intellectual property rights could be costly, time-consuming and distracting 
to management and could result in the impairment or loss of portions of their intellectual property. The litigation process is subject 
to inherent uncertainties, and they may not prevail in litigation matters regardless of the merits of their position. Further, adequate 
remedies may not be available in the event of an unauthorized use or disclosure of their trade secrets. Additionally, their efforts to 
enforce  their  intellectual  property  rights  may  be  met  with  defenses,  counterclaims  and  countersuits  attacking  the  validity  and 
enforceability  and  scope  of  their  intellectual  property  rights.  Our  insurance  subsidiaries’  failure  to  secure,  protect,  defend  and 
enforce their intellectual property rights could adversely affect their brand and adversely affect their business.

Our insurance subsidiaries’ success also depends in part on them not infringing, misappropriating or otherwise violating 
the intellectual property rights of others. Their competitors and other third parties may own or claim to own intellectual property 
relating  to  our  insurance  subsidiaries’  industry  and,  in  the  future,  may  claim  that  our  insurance  subsidiaries  are  infringing, 
misappropriating  or  otherwise  violating  their  intellectual  property  rights,  and  our  insurance  subsidiaries  may  be  found  to  be 
infringing on such rights. The outcome of any claims or litigation, regardless of the merits, is inherently uncertain. The disposition 
of  any  such  claims,  whether  through  settlement  or  licensing  discussions  or  litigation,  could  cause  our  insurance  subsidiaries  to 
incur significant expenses and, if successfully asserted against them, could require that they pay substantial damages or ongoing 
royalty  payments,  prevent  them  from  offering  certain  of  their  products  and  services,  require  them  to  change  their  technology  or 
business practices or require that they comply with other unfavorable terms. Even if our insurance subsidiaries were to prevail in 
such a dispute, any litigation could be costly and time-consuming, divert the attention of their management and key personnel from 
their business operations and materially adversely affect their business, financial condition and results of operations.

Our businesses employ third-party licensed software, and the inability to maintain these licenses, errors in the software 
they license or the terms of open source licenses could result in increased costs or reduced service levels, which would adversely 
affect their business.

Our businesses rely on certain third-party software obtained under licenses from other companies and anticipate that they 
will  continue  to  rely  on  such  third-party  software  in  the  future.  Although  they  believe  that  there  are  commercially  reasonable 
alternatives to the third-party software they currently license, this may not always be the case, or it may be difficult or costly to 
replace  their  existing  third-party  software.  In  addition,  integration  of  new  third-party  software  may  require  significant  work  and 
require  substantial  investment  of  their  time  and  resources.  Our  business’s  use  of  additional  or  alternative  third-party  software 
would  require  them  to  enter  into  license  agreements  with  third  parties,  which  may  not  be  available  on  commercially  reasonable 
terms  or  at  all.  Many  of  the  risks  associated  with  the  use  of  third-party  software  cannot  be  eliminated,  and  these  risks  could 
negatively impact their respective business.

Additionally, some of the software powering our business’s technology systems incorporates software covered by open 
source  licenses.  The  terms  of  many  open  source  licenses  have  not  been  interpreted  by  U.S.  courts,  and  there  is  a  risk  that  the 
licenses  could  be  construed  in  a  manner  that  imposes  unanticipated  conditions  or  restrictions  on  their  ability  to  operate  their 
systems. In the event that portions of their proprietary software are determined to be subject to an open source license, they could 
be required to publicly release the affected portions of their source code, which could allow our business’s clients and competitors 
to  freely  use  such  source  code  without  compensation  to  us,  or  re-engineer  all  or  a  portion  of  their  technology  systems,  each  of 
which could reduce or eliminate the value of their technology systems. While our businesses take steps to monitor the use of all 
software covered by open source licenses in our technology systems to ensure that no such software is used in such a way as to 
require us to disclose the source code to the related technology when they do not wish to do so, such use could inadvertently occur 

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and  could  harm  our  businesses,  results  of  operations,  financial  condition  and  cash  flows.  In  addition,  the  source  code  for  open 
source software is publicly available, which may make it easier for hackers and other third parties to determine how to breach our 
business’s  systems  that  rely  on  open  source  software  and  may  present  additional  security  risks.  Such  risk  could  be  difficult  or 
impossible to eliminate and could adversely affect our business’s, results of operations, financial condition and cash flows. Such 
risk could be difficult or impossible to eliminate and could adversely affect our business’s results of operations, financial condition 
and cash flows.

Some of our investments are made jointly with other persons or entities, which may limit our flexibility with respect to 
such jointly owned investments and could, thereby, have a material adverse effect on our business, results of operations and 
financial condition and our ability to sell these investments.

Some  of  our  current  investments  are,  and  future  investments  may  be,  made  jointly  with  other  persons  or  entities  when 
circumstances  warrant  the  use  of  such  structures  and  we  may  continue  to  do  so  in  the  future.  Our  participation  in  such  joint 
investments is subject to the risks that:

•

•

•

•
•
•

•

we could experience an impasse on certain decisions because we do not have sole decision-making authority, which could 
require us to expend additional resources on resolving such impasses or potential disputes; 
our  partners  could  have  investment  goals  that  are  not  consistent  with  our  investment  objectives,  including  the  timing, 
terms and strategies for any investments; 
our  partners  might  become  bankrupt,  fail  to  fund  their  share  of  required  capital  contributions  or  fail  to  fulfill  their 
obligations as partners, which may require us to infuse our own capital into such venture(s) on behalf of the partner(s) 
despite other competing uses for such capital; 
our partners may have competing interests in our markets that could create conflict of interest issues; 
any sale or other disposition of our interest in such a venture may require consents which we may not be able to obtain; 
such transactions may also trigger other contractual rights held by a partner, lender or other third-party depending on how 
the transaction is structured; and 
there may be disagreements as to whether consents and/or approvals are required in connection with the consummation of 
a  particular  transaction  with  a  partner,  lender  and/or  other  third-party,  or  whether  such  transaction  triggers  other 
contractual rights held by a partner, lender and/or other third-party, and in either case, those disagreements may result in 
litigation. 

Our mortgage business is significantly impacted by interest rates. Changes in prevailing interest rates or U.S. monetary 

policies that affect interest rates may have a detrimental effect on our mortgage business.

Changes  in  interest  rates  and  the  level  of  interest  rates  are  key  drivers  that  impact  the  volatility  of  our  mortgage  loan 
originations. The historically low interest rate environment over the last several years created strong demand for mortgages. While 
long-term  residential  mortgage  interest  rates  were  at  or  near  record  lows  for  an  extended  period,  in  2022  and  2023,  the  Federal 
Reserve initiated a rapid series of interest rate increases that resulted in lower revenue and profitability in our mortgage business. 
The overwhelming majority of our mortgage loan originations have historically been refinancing existing homeowner’s mortgage 
loans, with a particular emphasis on cash out refinancings. With the recent rise in interest rates, we may not be able to continue to 
grow our mortgage originations in the future. 

With regard to the portion of our mortgage business that is centered on refinancing existing mortgages, we generally note 
that the refinance market experiences more significant fluctuations than the purchase market as a result of interest rate changes, 
with the rate and term financing market impacted the most by the volatility in mortgage rates. As interest rates rise, refinancing 
generally becomes a smaller portion of the market as fewer consumers are interested in refinancing their mortgages. With regard to 
our  purchase  mortgage  loan  business,  higher  interest  rates  may  also  reduce  demand  for  purchase  mortgages  as  home  ownership 
becomes  more  expensive.  This  could  adversely  affect  our  mortgage  business’s  revenues  or  require  our  mortgage  business  to 
increase marketing expenditures in an attempt to increase or maintain its volume of mortgages. Decreases in interest rates can also 
adversely affect our mortgage business’s financial condition, the value of its mortgage servicing rights (“MSRs”) portfolio, and its 
results of operations. Even in sustained low interest rate environments, refinancing transactions decline over time, as many clients 
and potential clients have already taken advantage of the low interest rates.

Changes  in  interest  rates  are  also  a  key  driver  of  the  performance  of  our  servicing  business,  particularly  because  our 
mortgage  business’s  portfolio  is  composed  primarily  of  MSRs  related  to  high-quality  loans,  the  values  of  which  are  highly 
sensitive to changes in interest rates. Historically, the value of MSRs has increased when interest rates rise as higher interest rates 
lead  to  decreased  prepayment  rates,  and  has  decreased  when  interest  rates  decline  as  lower  interest  rates  lead  to  increased 
prepayment rates. As a result, decreases in interest rates could have a detrimental effect on our mortgage business.

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Borrowings under some of our mortgage business’s finance and warehouse facilities are at variable rates of interest, which 
also  expose  us  to  interest  rate  risk.  As  interest  rates  increase,  our  mortgage  business’s  debt  service  obligations  on  certain  of  its 
variable-rate  indebtedness  have  increased  even  though  the  amount  borrowed  remains  the  same,  and  net  income  and  cash  flows, 
including cash available for servicing indebtedness, have correspondingly decreased. Our mortgage business currently has entered 
into, and in the future may continue to enter into, interest rate swaps that involve the exchange of floating for fixed-rate interest 
payments to reduce interest rate volatility. However, our mortgage business may not maintain interest rate swaps with respect to all 
of its variable-rate indebtedness, and any such swaps may not fully mitigate its interest rate risk, may prove disadvantageous, or 
may create additional risks.

In  addition,  our  mortgage  business  is  materially  affected  by  the  monetary  policies  of  the  U.S.  government  and  its 
agencies. Our mortgage business is particularly affected by the policies of the Federal Reserve, which influence interest rates and 
impact the size of the loan origination market. In 2017, the Federal Reserve ended its quantitative easing program and started its 
balance  sheet  reduction  plan.  The  Federal  Reserve's  balance  sheet  consists  of  U.S.  Treasuries  and  mortgage-backed  securities 
(“MBS”) issued by Fannie Mae, Freddie Mac and Ginnie Mae. To shrink its balance sheet, the Federal Reserve had slowed the 
pace of MBS purchases to a point at which natural runoff exceeded new purchases, resulting in a net reduction. In response to the 
COVID-19 pandemic, state and federal authorities took several actions to provide relief to those negatively affected by COVID-19, 
such  as  the  CARES  Act  and  the  Federal  Reserve's  support  of  the  financial  markets.  The  lasting  results  of  these  policies  by  the 
Federal Reserve are unknown at this time.

Our  mortgage  business’s  MSRs  are  highly  volatile  assets  with  continually  changing  values,  and  these  changes  in 
value, or inaccuracies in estimates of their value, could adversely affect our mortgage business’s financial condition and results 
of operations.

The value of our mortgage business’s MSRs is based on the cash flows projected to result from the servicing of the related 
mortgage loans and continually fluctuates due to a number of factors. These factors include changes in interest rates; historically, 
the  value  of  MSRs  has  increased  when  interest  rates  rise  as  higher  interest  rates  lead  to  decreased  prepayment  rates,  and  has 
decreased  when  interest  rates  decline  as  lower  interest  rates  lead  to  increased  prepayment  rates  and  refinancings.  Other  market 
conditions also affect the number of loans that are refinanced and thus no longer result in cash flows, and the number of loans that 
become delinquent.

Our mortgage business uses two external valuation firms to fair value its MSR assets. These valuation firms utilize market 
participant data and actual MSR market trades to value our MSRs for purposes of financial reporting, These models are complex 
and use asset-specific collateral data and market inputs for interest and discount rates. In addition, the modeling requirements of 
MSRs  are  complex  because  of  the  high  number  of  variables  that  drive  cash  flows  associated  with  MSRs,  and  because  of  the 
complexity  involved  with  anticipating  such  variables  over  the  life  of  the  MSR.  Even  if  the  general  accuracy  of  their  valuation 
models is validated, valuations are highly dependent upon the reasonableness of their assumptions and the results of the models. If 
loan  delinquencies  or  prepayment  speeds  are  higher  than  anticipated  or  other  factors  perform  worse  than  modeled,  the  recorded 
value of certain of their MSRs may decrease, which could adversely affect their business and financial condition.

Our mortgage business is highly dependent upon programs administered by GSEs, such as Fannie Mae and Freddie 
Mac,  as  well  as  Ginnie  Mae,  to  generate  revenues  through  mortgage  loan  sales  to  institutional  investors.  Any  changes  in 
existing U.S. government-sponsored mortgage programs could materially and adversely affect our mortgage business, financial 
condition and results of operations.

There is uncertainty regarding the future of Fannie Mae and Freddie Mac, including with respect to how long they will 
continue to be in existence, the extent of their roles in the market and what forms they will have. The future roles of Fannie Mae 
and  Freddie  Mac  could  be  reduced  or  eliminated  and  the  nature  of  their  guarantees  could  be  limited  or  eliminated  relative  to 
historical measurements. The elimination or modification of the traditional roles of Fannie Mae or Freddie Mac could adversely 
affect  our  mortgage  business,  financial  condition  and  results  of  operations.  Furthermore,  any  discontinuation  of,  or  significant 
reduction  in,  the  operation  of  these  GSEs  and  Ginnie  Mae,  or  any  significant  adverse  change  in  the  level  of  activity  of  these 
agencies  in  the  primary  or  secondary  mortgage  markets  or  in  the  underwriting  criteria  of  these  agencies  could  materially  and 
adversely affect our business, financial condition and results of operations.

We may be unable to obtain sufficient capital to meet the financing requirements of our mortgage business.

We fund substantially all of the loans which we originate through borrowings under warehouse financing and repurchase 
facilities. Our borrowings are in turn repaid with the proceeds we receive from selling such loans through securitizations, and to a 
lesser extent given our business model, whole loan sales. As we expand our operations, we will require increased financing.

There can be no assurance that such financing will be available on terms reasonably satisfactory to us or at all. An event 

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of default, an adverse action by a regulatory authority or a general deterioration in the economy that constricts the availability of 
credit-similar to the market conditions experienced in recent years-may increase our cost of funds and make it difficult for us to 
obtain new, or retain existing, warehouse financing facilities. If we fail to maintain, renew or obtain adequate funding under these 
warehouse financing facilities or other financing arrangements, or there is a substantial reduction in the size of or increase in the 
cost of such facilities, we would have to curtail our mortgage loan production activities, which could have a material adverse effect 
on our business, financial condition and operating results in our mortgage business.

If the value of the collateral underlying certain of our mortgage business’s loan funding facilities decreases, they could 

be required to satisfy a margin call, and an unanticipated margin call could have a material adverse effect on their liquidity.

Certain of our mortgage business’s loan funding, early buy-out facilities, and MSR-backed facilities are subject to margin 
calls based on the lender's opinion of the value of the loan collateral securing such financing and certain of their hedges related to 
newly originated mortgages are also subject to margin calls. A margin call would require our mortgage business to repay a portion 
of the outstanding borrowings. A large, unanticipated margin call could have a material adverse effect on their liquidity.

In our mortgage business, we may sustain losses and/or be required to indemnify or repurchase loans we originated, or 

will originate, if, among other things, our loans fail to meet certain criteria or characteristics. 

Securitizations  guaranteed  by  government  agencies  and  contracts  with  purchasers  of  our  mortgage  loans  contain 
provisions  that  require  us  to  indemnify  or  repurchase  the  related  loans  under  certain  circumstances.  While  these  contractual 
relationships vary, they contain provisions that require us to repurchase loans if: 

•

•
•
•

our  representations  and  warranties  concerning  loan  quality  and  loan  circumstances  are  inaccurate,  including 
representations concerning the licensing of a mortgage broker;
we fail to secure adequate mortgage insurance within a certain period after closing; 
a mortgage insurance provider denies coverage; or 
we  fail  to  comply,  at  the  individual  loan  level  or  otherwise,  with  regulatory  requirements  in  the  current  dynamic 
regulatory environment. 

We  maintain  reserves  that  we  believe  are  appropriate  to  cover  potential  loan  repurchase  or  indemnification  losses,  but 
there can be no assurance that such reserves will, in fact, be sufficient to cover future repurchase and indemnification claims. If we 
are  required  to  indemnify  or  repurchase  loans  that  we  originate  and  sell  that  result  in  losses  that  exceed  our  reserve,  this  could 
adversely affect our business, financial condition and results of operations. 

Furthermore, in the ordinary course of our mortgage business, we are subject to claims made against us by borrowers and 
private investors arising from, among other things, losses that are claimed to have been incurred as a result of alleged breaches of 
fiduciary  obligations,  misrepresentations,  errors  and  omissions  of  our  employees,  officers  and  agents  (including  our  appraisers), 
incomplete documentation and our failure to comply with various laws and regulations applicable to our business. 

In addition, should the mortgage loans we originate sustain higher levels of delinquencies and/or defaults, we may lose the 
ability to originate and/or sell FHA loans, or to do so profitably and investors to whom we currently sell our mortgage loans may 
refuse to continue to do business with us, or may reduce the prices they are willing to purchase our mortgage loans and it may be 
difficult  or  impossible  to  sell  any  of  our  mortgage  loans  in  the  future.  Any  of  the  foregoing  risks  could  adversely  affect  our 
business, financial condition and results of operations in our mortgage business.

We may be limited in the future in utilizing net operating losses incurred during prior periods to offset taxable income.

We previously incurred net operating losses. In the event that we experience an “ownership change” within the meaning 
of  Section  382  of  the  Code,  our  ability  to  use  those  net  operating  losses  to  offset  taxable  income  could  be  subject  to  an  annual 
limitation. The annual limitation would be equal to a percentage of our equity value at the time the ownership change occurred. In 
general, such an “ownership change” would occur if the percentage of our stock owned by one or more 5% stockholders (including 
certain groups or persons acting in concert) were to increase by 50 percentage points during any three-year period. All stockholders 
that own less than 5% of our stock are treated as a single 5% stockholder. In addition, the Treasury Regulations under Section 382 
of the Code contain additional rules the effect of which is to make it more likely that an ownership change could be deemed to 
occur. Accordingly, our ability to use prior net operating losses to offset future taxable income would be subject to a limitation if 
we experience an ownership change.

We may leverage certain of our assets and a decline in the fair value of such assets may adversely affect our financial 

condition and results of operations.

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We  leverage  certain  of  our  assets,  including  through  borrowings,  generally  through  warehouse  credit  facilities,  secured 
loans,  securitizations  and  other  borrowings.  A  rapid  decline  in  the  fair  value  of  our  leveraged  assets  may  adversely  affect  us. 
Lenders may require us to post additional collateral to support the borrowing. If we cannot post the additional collateral, we may 
have to rapidly liquidate assets, which we may be unable to do on favorable terms or at all. Even after liquidating assets, we may 
still be unable to post the required collateral, further harming our liquidity and subjecting us to liability to lenders for the declines 
in  the  fair  values  of  the  collateral.  A  reduction  in  credit  availability  may  adversely  affect  our  business,  financial  condition  and 
results of operations.

Certain of our and our subsidiaries’ assets are subject to credit risk, market risk, interest rate risk, credit spread risk, 
call and redemption risk and refinancing risk, and any one of these risks may materially and adversely affect the value of our 
assets, our results of operations and our financial condition.

Some of our assets, including our direct investments, are subject to credit risk, market risk, interest rate risk, credit spread 

risk, call and redemption risk and refinancing risk.

Credit risk is the risk that the obligor will be unable to pay scheduled principal and/or interest payments. Defaults by third 
parties in the payment or performance of their obligations could reduce our income and realized gains or result in the recognition of 
losses. The fair value of our assets may be materially and adversely affected by increases in interest rates, downgrades in our direct 
investments and by other factors that may result in the recognition of other-than-temporary impairments. Each of these events may 
cause us to reduce the fair value of our assets.

Interest rate risk is the risk that general interest rates will rise or that the risk spread used in our financings will increase. 
Although interest rates were at historically low levels for the last several years, the recent period of sharply rising interest rates has 
resulted  in  unrealized  losses  on  the  fair  value  of  certain  of  our  investments  and  has  had  an  adverse  impact  on  our  business  by 
negatively impacting our results and increasing our cost of borrowing to finance operations. 

On March 5, 2021, the ICE Benchmark Administration and the United Kingdom Financial Conduct Authority confirmed 
that most USD LIBOR tenors will continue to be published through the second quarter of 2023. We have exposure to LIBOR–
based  contracts  within  certain  of  our  finance  receivables  and  loans  primarily  related  to  corporate  finance  loans,  and  mortgage 
loans, as well as certain investment securities, derivative contracts, and trust preferred securities, among other arrangements. The 
Federal  Reserve,  in  conjunction  with  the  Alternative  Reference  Rates  Committee,  a  steering  committee  comprised  of  large  U.S. 
financial institutions, has recommended the Secured Overnight Finance Rate (SOFR), as an alternative to LIBOR. SOFR is a broad 
measure of the cost of borrowing cash in the overnight U.S. treasury repo market. There can be no assurance that rates linked to 
SOFR, or associated changes related to the adoption of SOFR, will be as favorable to us as LIBOR and may result in an effective 
increase  in  the  applicable  interest  rate  on  our  current  or  future  debt  obligations.  As  a  result,  the  discontinuation  of  LIBOR  or 
LIBOR–based rates will present risks to our business. 

Market risk is the risk that one or more markets to which the assets relate will decline in value, including the possibility 

that such markets will deteriorate sharply and unpredictably, which will likely impair the market value of the related instruments.

Credit  spread  risk  is  the  risk  that  the  market  value  of  fixed  income  investments  will  change  in  response  to  changes  in 

perceived or actual credit risk beyond changes that would be attributable to changes, if any, in interest rates.

Call and redemption risk is the risk that fixed income investments will be called or redeemed prior to maturity at a time 
when yields on other debt instruments in which the call or redemption proceeds could be invested are lower than the yield on the 
called or redeemed investments.

Refinancing risk is the risk that we will be unable to refinance some or all of our indebtedness or that any refinancing will 
not  be  on  terms  as  favorable  as  those  of  our  existing  indebtedness,  which  could  increase  our  funding  costs,  limit  our  ability  to 
borrow, or result in a sale of the leveraged asset on disadvantageous terms.

Any one of the risks described above may materially and adversely affect the value of our assets, our results of operations 

and our financial condition.

Our  risk  mitigation  or  hedging  strategies  could  result  in  our  experiencing  significant  losses  that  may  materially 

adversely affect us.

We may pursue risk mitigation and hedging strategies to seek to reduce our exposure to losses from adverse credit events, 
interest rate changes, market risk and other risks. These strategies may include short Treasury positions, interest rate swaps, foreign 

44

exchange derivatives, credit derivatives, freight forward agreements, fuel oil swaps and other derivative hedging instruments. Since 
we  account  for  derivatives  at  fair  market  value,  changes  in  fair  market  value  are  reflected  in  net  income  other  than  derivative 
hedging  instruments  which  are  reflected  in  accumulated  other  comprehensive  income  in  stockholders’  equity.  Some  of  these 
strategies could result in our experiencing significant losses that may materially adversely affect our business, financial condition 
and results of operations.

The  values  we  record  for  certain  investments  and  liabilities  are  based  on  estimates  of  fair  value  made  by  our 
management, which may cause our operating results to fluctuate and may not be indicative of the value we can realize on a 
sale.

Some of our investments and liabilities are not actively traded and the fair value of such investments and liabilities are not 
readily determinable. Each of these carrying values is based on an estimate of fair value by our management. Management reports 
the estimated fair value of these investments and liabilities quarterly, which may cause our quarterly operating results to fluctuate. 
Therefore,  our  past  quarterly  results  may  not  be  indicative  of  our  performance  in  future  quarters.  In  addition,  because  such 
valuations  are  inherently  uncertain,  in  some  cases  based  on  internal  models  and  unobservable  inputs,  may  fluctuate  over  short 
periods of time and may be based on estimates, our determinations of fair value may differ materially from the values that would 
have been used if a ready market for these investments and liabilities existed. As such, we may be unable to realize the carrying 
value upon a sale of these investments or liabilities.

The  accounting  rules  applicable  to  certain  of  our  transactions  are  highly  complex  and  require  the  application  of 
significant judgment and assumptions by our management. In addition, changes in accounting interpretations or assumptions 
could impact our financial statements.

Accounting rules for consolidations, income taxes, business acquisitions, transfers of financial assets and other aspects of 
our  operations  are  highly  complex  and  require  the  application  of  judgment  and  assumptions  by  our  management.  In  addition, 
changes in accounting rules, interpretations or assumptions could materially impact the presentation, disclosure and usability of our 
financial statements. For more information see Item 7. “Management’s Discussion and Analysis of Financial Condition and Results 
of Operations — Critical Accounting Policies and Estimates”. 

Changes in accounting practices and future pronouncements may materially affect our reported financial results.

Developments in accounting practices may require us to incur considerable additional expenses to comply with new rules, 
particularly if we are required to prepare information relating to prior periods for comparative purposes or to otherwise apply the 
new  requirements  retroactively.  The  impact  of  changes  in  current  accounting  practices  and  future  pronouncements  cannot  be 
predicted but may affect the calculation of net income, stockholders’ equity and other relevant financial statement line items.

Our insurance subsidiaries are required are required to comply with Statutory Accounting Principles (“SAP”). SAP and 
various  components  of  SAP  are  subject  to  constant  review  by  the  NAIC  and  its  task  forces  and  committees,  as  well  as  state 
insurance departments, in an effort to address emerging issues and otherwise improve financial reporting. Various proposals are 
pending  before  committees  and  task  forces  of  the  NAIC,  some  of  which,  if  enacted,  could  have  negative  effects  on  insurance 
industry participants. The NAIC continuously examines existing laws and regulations. Whether or in what form such reforms will 
be enacted and, if so, whether the enacted reforms will positively or negatively affect us is unknown.

Catastrophic events could significantly impact the Company’s businesses.

Unforeseen or catastrophic events, such as severe weather, natural disasters, pandemics (e.g. the COVID 19 pandemic) 
cybersecurity attacks, acts of war or terrorism and other adverse external events could have a significant impact on the Company’s 
ability  to  conduct  business.  Although  the  Company  and  its  subsidiaries  have  established  disaster  recovery  plans,  there  is  no 
guarantee that such plans will allow the Company and its subsidiaries to operate without disruption if such an event was to occur 
and the occurrence of any such event could have a material adverse effect on the Company’s business, which, in turn, could have a 
material adverse effect on the Company’s financial condition and results of operations.

Acts of war may disrupt international trade, create market volatility in debt, equity and commodities markets and result in 
import bans, export control regulations, increased costs, and sanctions by governmental authorities. These effects, individually or 
in the aggregate, could materially adversely impact our businesses, operations, financial condition, operating results, liquidity and 
cash flows and such adverse impacts may be material to our results of operations and liquidity position.

Whether  or  to  what  extent  damage  that  may  be  caused  by  natural  events,  such  as  wildfires,  severe  tropical  storms  and 
hurricanes, will affect our insurance subsidiaries’ ability to write new insurance policies and reinsurance contracts is unknown, but, 

45

to the extent our insurance subsidiaries’ policies are concentrated in the specific geographic areas in which these events occur, any 
increase in frequency and severity of such events and the total amount of our loss exposure in the impacted areas of such events 
may adversely affect their business, financial condition and results of operations. In addition, although our insurance subsidiaries 
have historically had limited exposure to catastrophic risk, claims from catastrophe events could reduce their earnings and cause 
substantial volatility in their business, financial condition and results of operations for any period. Assessing the risk of loss and 
damage associated with natural and catastrophic events remains a challenge and might adversely affect their business, results of 
operations, financial condition and cash flows.

Our  business,  particularly  our  insurance  subsidiaries’  business,  is  exposed  to  risks  associated  with  severe  weather 
conditions  and  other  catastrophes.  Catastrophes  can  be  caused  by  various  events,  including  natural  events  such  as  severe  winter 
weather, tornadoes, windstorms, earthquakes, hailstorms, severe thunderstorms and fires, and other events such as explosions, war, 
terrorist attacks and riots. The incidence and severity of catastrophes and severe weather conditions are inherently unpredictable. 
For example, our insurance subsidiary underwrites property risks in geographies that are subject to earthquakes, such as California, 
in  geographies  that  are  subject  to  wildfires,  such  as  the  southwestern  United  States,  and  in  geographies  that  are  subject  to 
windstorms,  such  as  the  southeastern  United  States.  The  extent  of  losses  from  catastrophes  is  a  function  of  the  total  amount  of 
insured value, the number of insureds affected, the frequency and severity of the events, the effectiveness of our catastrophe risk 
management  program  and  the  adequacy  of  our  reinsurance  coverage.  Insurance  companies  are  not  permitted  to  reserve  for  a 
catastrophe until it has occurred. Severe weather conditions and catastrophes can cause losses in our property lines and generally 
result in both an increase in the number of claims incurred and an increase in the dollar amount of each claim asserted, which may 
require us to increase our reserves, causing our liquidity and financial condition to deteriorate. In addition, our inability to obtain 
reinsurance coverage at reasonable rates, and in amounts adequate to mitigate the risks associated with severe weather conditions 
and other catastrophes, could have a material adverse effect on our business and results of operations. Further toward mitigating 
these risks, we underwrite a diversified mix of programs that span across multiple lines of business, industries, geographies and 
distribution channels. 

In  addition,  while  policy  terms  and  conditions  for  our  insurance  subsidiaries’  lines  of  business  preclude  coverage  for 
virus-related claims, court decisions and governmental actions may challenge the validity of any exclusions or our interpretation of 
how such terms and conditions operate. If pandemics, disease outbreaks and other events occur or re-occur and measures that are 
put  into  place  by  various  governmental  authorities  to  stabilize  the  economy  are  not  effective,  our  business,  financial  condition, 
results of operations and cash flows may be materially adversely affected.

U.S. insurers are required by state and federal law to offer coverage for acts of terrorism in certain commercial lines. The 
Terrorism  Risk  Insurance  Act,  as  extended  by  the  Terrorism  Risk  Insurance  Program  Reauthorization  Act  of  2015  (“TRIPRA”) 
requires commercial property and casualty (“P&C”) insurance companies to offer coverage for acts of terrorism, whether foreign 
or domestic, and established a federal assistance program through the end of 2020 to help cover claims related to future terrorism-
related losses. The likelihood and impact of any terrorist act is unpredictable, and the ultimate impact on our insurance subsidiaries 
would depend upon the nature, extent, location and timing of such an act. Although our insurance subsidiaries reinsure a portion of 
the terrorism risk they retain under TRIPRA, such terrorism reinsurance does not provide full coverage for an act stemming from 
nuclear, biological or chemical terrorism. To the extent an act of terrorism, whether a domestic or foreign act, is certified by the 
Secretary  of  Treasury,  our  insurance  subsidiaries  may  be  covered  under  TRIPRA  for  their  losses  for  certain  P&C  lines  of 
insurance. However, any such coverage would be subject to a mandatory deductible based on 20% of earned premium for the prior 
year for the covered commercial P&C insurance.

Risks Related to our Structure

Because we are a holding company, our ability to meet our obligations and pay dividends to stockholders will depend 

on distributions from our subsidiaries that may be subject to restrictions and income from assets.

We are a holding company and do not have any significant operations of our own, other than our principal investments. 
Our  ability  to  meet  our  obligations  will  depend  on  distributions  from  our  subsidiaries  and  income  from  assets.  The  amount  of 
dividends  and  other  distributions  that  our  subsidiaries  may  distribute  to  us  may  be  subject  to  restrictions  imposed  by  state  law, 
restrictions that may be imposed by state regulators and restrictions imposed by the terms of any current or future indebtedness that 
these  subsidiaries  may  incur.  Such  restrictions  would  also  affect  our  ability  to  pay  dividends  to  stockholders,  if  and  when  we 
choose to do so. 

Our insurance business’s Junior Subordinated Notes due 2057 and $200 million revolving credit facility restrict dividends 
to  us  based  on  the  leverage  ratio  of  our  insurance  business  and  its  subsidiaries.  Additionally,  our  regulated  insurance  company 
subsidiaries are required to satisfy minimum capital and surplus requirements according to the laws and regulations of the states in 
which  they  operate,  which  regulate  the  amount  of  dividends  and  distributions  we  receive  from  them.  In  general,  dividends  in 

46

excess of prescribed limits are deemed “extraordinary” and require insurance regulatory approval. Ordinary dividends, for which 
no regulatory approval is generally required, are limited to amounts determined by a formula, which varies by state. Some states 
have an additional stipulation that dividends may only be paid out of earned surplus. States also regulate transactions between our 
insurance company subsidiaries and us or our other subsidiaries, such as those relating to compensation for shared services, and in 
some instances, require prior approval of such transactions within the holding company structure. If insurance regulators determine 
that payment of an ordinary dividend or any other payments by our insurance company subsidiaries to us or our other subsidiaries 
(such  as  payments  for  employee  or  other  services)  would  be  adverse  to  policyholders  or  creditors,  the  regulators  may  block  or 
otherwise  restrict  such  payments  that  would  otherwise  be  permitted  without  prior  approval.  In  addition,  there  could  be  future 
regulatory  actions  restricting  the  ability  of  our  insurance  company  subsidiaries  to  pay  dividends  or  share  services.  The  primary 
factor  in  determining  the  amount  of  capital  available  for  potential  dividends  is  the  level  of  capital  needed  to  maintain  desired 
financial  strength  ratings  from  rating  agencies  for  our  insurance  company  subsidiaries.  Given  recent  economic  events  that  have 
affected  the  insurance  industry,  both  regulators  and  rating  agencies  could  become  more  conservative  in  their  methodology  and 
criteria, including increasing capital requirements for our insurance company subsidiaries which, in turn, could negatively affect 
our capital resources.

Some  provisions  of  our  charter  may  delay,  deter  or  prevent  takeovers  and  business  combinations  that  stockholders 

consider in their best interests.

Our  charter  restricts  any  person  that  owns  9.8%  or  more  of  our  capital  stock,  other  than  stockholders  approved  by 
applicable state insurance regulators, from voting in excess of 9.8% of our voting securities. This provision is intended to satisfy 
the  requirements  of  applicable  state  regulators  in  connection  with  insurance  laws  and  regulations  that  prohibit  any  person  from 
acquiring control of a regulated insurance company without the prior approval of the insurance regulators. In addition, our charter 
provides for the classification of our board of directors into three classes, one of which is to be elected each year. Our charter also 
generally only permits stockholders to act without a meeting by unanimous consent. These provisions may delay, deter or prevent 
takeovers and business combinations that stockholders consider in their best interests.

Maryland takeover statutes may prevent a change of our control, which could depress our stock price.

Maryland law provides that “control shares” of a corporation acquired in a “control share acquisition” will have no voting 
rights  except  to  the  extent  approved  by  a  vote  of  two-thirds  of  the  votes  entitled  to  be  cast  on  the  matter  under  the  Maryland 
Control  Share  Acquisition  Act.  “Control  shares”  means  voting  shares  of  stock  that,  if  aggregated  with  all  other  shares  of  stock 
owned by the acquirer or in respect of which the acquirer is able to exercise or direct the exercise of voting power (except solely by 
virtue of a revocable proxy), would entitle the acquirer to exercise voting power in electing directors within one of the following 
ranges of voting power: one-tenth or more but less than one-third; one-third or more but less than a majority; or a majority or more 
of all voting power. A “control share acquisition” means the acquisition of issued and outstanding control shares, subject to certain 
exceptions.

Under  Maryland  law,  “business  combinations”  between  a  Maryland  corporation  and  an  interested  stockholder  or  an 
affiliate of an interested stockholder are prohibited for five years after the most recent date on which such stockholder became an 
interested stockholder. These business combinations include a merger, consolidation, share exchange or, in circumstances specified 
in the statute, an asset transfer or issuance or reclassification of equity securities.

Our bylaws contain a provision exempting from the control share statute any and all acquisitions by any person of our 
shares of stock. Our board of directors has also adopted a resolution which provides that any business combination between us and 
any other person is exempted from the provisions of the business combination statute, provided that the business combination is 
first  approved  by  the  board  of  directors.  However,  our  board  of  directors  may  amend  or  eliminate  this  provision  in  our  bylaws 
regarding the control share statute or amend or repeal this resolution regarding the business combination statute. If our board takes 
such  action  in  the  future,  the  control  share  and  business  combination  statutes  may  prevent  or  discourage  others  from  trying  to 
acquire control of us and increase the difficulty of consummating any offer, including potential acquisitions that might involve a 
premium price for our common stock or otherwise be in the best interest of our stockholders.

Our holding company structure with multiple lines of business, may adversely impact the market price of our common 

stock and our ability to raise equity and debt capital.

Tiptree holds and manages multiple lines of business. Analysts, investors and lenders may have difficulty analyzing and 
valuing a company with multiple lines of business, which could adversely impact the market price of our common stock and our 
ability  to  raise  equity  and  debt  capital  at  a  holding  company  level.  Moreover,  our  management  is  required  to  make  decisions 
regarding the allocation of capital among the different lines of business, and such decisions could materially and adversely affect 
our business or one or more of our lines of business.

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Risks Related to Regulatory and Legal Matters

Maintenance of our 1940 Act exemption imposes limits on our operations.

We  conduct  our  operations  so  that  we  are  not  required  to  register  as  an  investment  company  under  the  1940  Act. 
Therefore,  we  must  limit  the  types  and  nature  of  businesses  in  which  we  engage  and  assets  that  we  acquire.  We  monitor  our 
compliance  with  the  1940  Act  on  an  ongoing  basis  and  may  be  compelled  to  take  or  refrain  from  taking  actions,  to  acquire 
additional income or loss generating assets or to forgo opportunities that might otherwise be beneficial or advisable, including, but 
not limited to selling assets that are considered to be investment securities or forgoing the sale of assets that are not investment 
securities,  in  order  to  ensure  that  we  (or  a  subsidiary)  may  continue  to  rely  on  the  applicable  exceptions  or  exemptions.  These 
limitations on our freedom of action could have a material adverse effect on our financial condition and results of operations.

If we fail to maintain an exemption, exception or other exclusion from registration as an investment company, we could, 
among  other  things,  be  required  to  substantially  change  the  manner  in  which  we  conduct  our  operations  either  to  avoid  being 
required  to  register  as  an  investment  company  or  to  register  as  an  investment  company.  If  we  were  required  to  register  as  an 
investment company under the 1940 Act, we would become subject to substantial regulation with respect to, among other things, 
our  capital  structure  (including  our  ability  to  use  leverage),  management,  operations,  transactions  with  affiliated  persons  (as 
defined in the 1940 Act), portfolio composition, including restrictions with respect to diversification and industry concentration, 
and our financial condition and results of operations may be adversely affected. If we did not register despite being required to do 
so,  criminal  and  civil  actions  could  be  brought  against  us,  our  contracts  would  be  unenforceable  unless  a  court  were  to  require 
enforcement, and a court could appoint a receiver to take control of us and liquidate our business.

A  change  in  law,  regulation  or  regulatory  enforcement  applicable  to  insurance  products  could  adversely  affect  our 

financial condition and results of operations.

A change in state or U.S. federal tax laws could materially affect our insurance businesses. For example, tax legislation 
commonly  referred  to  as  the  Tax  Cuts  and  Jobs  Act  (the  “TCJA”),  which  was  signed  into  law  on  December  22,  2017, 
fundamentally overhauled the U.S. tax system by, among other significant changes, reducing the U.S. corporate income tax rate to 
21%. In the context of the taxation of U.S. P&C insurance companies such as our insurance companies, the TCJA also modified 
the  loss  reserve  discounting  rules  and  the  proration  rules  that  apply  to  reduce  reserve  deductions  to  reflect  the  lower  corporate 
income tax rate, which could have an adverse impact on our insurance subsidiaries. It is possible that other legislation could be 
introduced  and  enacted  by  the  current  Congress  or  future  Congresses  that  could  have  an  adverse  impact  on  our  insurance 
subsidiaries.  Additional  regulations  or  pronouncements  interpreting  or  clarifying  provisions  of  the  TCJA  have  been  and  will 
continue to be issued, and such regulations or pronouncements may be different from our insurance subsidiaries’ interpretation and 
thus  adversely  affect  their  results.  If,  when  or  in  what  form  such  regulations  or  pronouncements  may  be  provided  or  finalized, 
whether  such  guidance  will  have  a  retroactive  effect  or  such  regulations’  or  pronouncements’  potential  impact  on  our  insurance 
subsidiaries is unknown.

Currently,  our  insurance  business  does  not  collect  sales  or  other  related  taxes  on  its  services.  Whether  sales  of  our 
insurance business’s services are subject to state sales and use taxes is uncertain, due in part to the nature of its services and the 
relationships through which its services are offered, as well as changing state laws and interpretations of those laws. One or more 
states may seek to impose sales or use tax or other tax collection obligations on our insurance business, whether based on sales by 
our insurance business or its resellers or clients, including for past sales. A successful assertion that our insurance business should 
be collecting sales or other related taxes on its services could result in substantial tax liabilities for past sales, discourage customers 
from  purchasing  its  services,  discourage  clients  from  offering  or  billing  for  its  services,  or  otherwise  cause  material  harm  to  its 
business, financial condition and results of operations.

With regard to our insurance business’s payment protection products and financing of VSCs, there are federal and state 
laws and regulations that govern the disclosures related to the sales of those products. Our insurance business’s ability to offer and 
administer these products on behalf of their distribution partners is dependent upon their continued ability to sell such products. To 
the extent that federal or state laws or regulations change to restrict or prohibit the sale of these products, our insurance business’s 
revenues  would  be  adversely  affected.  For  example,  the  CFPB’s  enforcement  actions  have  resulted  in  large  refunds  and  civil 
penalties against financial institutions in connection with their marketing of payment protection and other products. Due to such 
regulatory actions, some lenders may reduce their sales and marketing of payment protection and other ancillary products, which 
may adversely affect our insurance business’s revenues. The full impact of the CFPB’s oversight is unpredictable and continues to 
evolve.  With  respect  to  the  P&C  insurance  policies  our  insurance  business  underwrites,  federal  legislative  proposals  regarding 
national  catastrophe  insurance,  if  adopted,  could  reduce  the  business  need  for  some  of  the  related  products  that  our  insurance 
business provides. 

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Increasing  regulatory  focus  on  privacy  issues  and  expanding  laws  could  affect  our  various  subsidiaries’  business 

model and expose them to increased liability.

Some  of  our  subsidiaries  collect,  use,  store,  transmit,  retrieve,  retain  and  otherwise  process  confidential  and  personally 
identifiable  information  in  their  information  systems  in  and  across  multiple  jurisdictions,  and  they  are  subject  to  a  variety  of 
confidentiality obligations and privacy, data protection and information security laws, regulations, orders and industry standards in 
the  jurisdictions  in  which  they  do  business.  The  regulatory  environment  surrounding  information  security,  data  privacy  and 
cybersecurity is evolving and increasingly demanding and there has been an increasing focus on privacy and data protection issues 
with the potential to affect our businesses. A number of our subsidiaries are subject to numerous U.S. federal and state laws and 
non-U.S. regulations governing the collection, transmission, storage, use and protection of personally identifiable and confidential 
information  of  their  customers  and  employees.  Failure  to  comply  with  any  of  these  laws  and  regulations  could  result  in 
enforcement  action  against  us,  including  fines,  imprisonment  of  company  officials  and  public  censure,  claims  for  damages  by 
affected  individuals,  damage  to  our  reputation  and  loss  of  goodwill,  any  of  which  could  have  a  material  adverse  effect  on  our 
business,  results  of  operations,  financial  condition  and  cash  flows.  On  October  24,  2017,  the  NAIC  adopted  an  Insurance  Data 
Security  Model  Law,  which  requires  licensed  insurance  entities  to  comply  with  detailed  information  security  requirements.  The 
NAIC model law has been adopted by certain states and is under consideration by others. It is not yet known whether or not, and to 
what  extent,  states  legislatures  or  insurance  regulators  where  our  insurance  subsidiaries  operate  will  enact  the  Insurance  Data 
Security Model Law in whole or in part, or in a modified form. Such enactments, especially if inconsistent between states or with 
existing  laws  and  regulations,  could  raise  compliance  costs  or  increase  the  risk  of  noncompliance,  and  noncompliance  could 
subject our insurance subsidiaries to regulatory enforcement actions and penalties, as well as reputational harm. Any such events 
could potentially have an adverse impact on our insurance subsidiaries’ business, results of operations, financial condition and cash 
flows.

Our insurance and mortgage subsidiaries are subject to the privacy regulations of the Gramm-Leach-Bliley Act of 1999 
(the “Gramm-Leach-Bliley Act”), along with its implementing regulations, which restricts certain collection, processing, storage, 
use  and  disclosure  of  personal  information,  requires  notice  to  individuals  of  privacy  practices,  provides  individuals  with  certain 
rights to prevent the use and disclosure of certain nonpublic or otherwise legally protected information and imposes requirements 
for the safeguarding and proper destruction of personal information through the issuance of data security standards or guidelines. In 
addition, on March 1, 2017, new cybersecurity rules took effect for financial institutions, insurers and certain other companies, like 
our  insurance  and  mortgage  subsidiaries,  supervised  by  the  NY  Department  of  Financial  Services  (the  “NY  DFS  Cybersecurity 
Regulation”).  The  NY  DFS  Cybersecurity  Regulation  imposes  significant  regulatory  burdens  intended  to  protect  the 
confidentiality,  integrity  and  availability  of  information  systems.  Our  insurance  and  mortgage  subsidiaries  also  have  contractual 
obligations to protect confidential and personally identifiable information we obtain from third parties. These obligations generally 
require them, in accordance with applicable laws, to protect such information to the same extent that they protect their own such 
information. 

Many states in which our insurance and mortgage subsidiaries operate have laws that protect the privacy and security of 
sensitive  and  personal  information.  Certain  current  or  proposed  state  laws  may  be  more  stringent  or  broader  in  scope,  or  offer 
greater individual rights, with respect to sensitive and personal information than federal, international or other state laws, and such 
laws may differ from each other, which may complicate compliance efforts. For example, certain of our insurance and mortgage 
businesses are subject to the California Consumer Privacy Act of 2018, as amended by the California Privacy Rights Act of 2020 
(collectively,  the  “CCPA”),  which  among  other  things,  requires  companies  covered  by  the  legislation  to  provide  disclosures  to 
California  consumers  and  affords  such  consumers  rights  of  access  and  deletion  of  personal  information.  Internationally,  many 
jurisdictions have established their own data security and privacy legal framework with which our insurance subsidiaries operating 
in  such  jurisdictions,  or  their  customers,  may  need  to  comply,  including,  but  not  limited  to,  the  EU.  The  EU  has  adopted  the 
General Data Protection Regulation, or the GDPR, which contains numerous requirements, robust obligations on data processors 
and heavier documentation requirements for data protection compliance programs by companies. The GDPR imposes significant 
penalties  for  non-compliance  with  fines  of  up  to  4%  of  total  annual  worldwide  turnover  or  €20  million  (whichever  is  higher), 
depending  on  the  type  and  severity  of  the  violation.  In  addition,  following  Brexit,  the  U.K.  General  Data  Protection  Regulation 
(i.e., a version of the GDPR as implemented into U.K. law) went into effect, which may expose us to burdens and risks comparable 
to those of the GDPR.

Because  the  interpretation  and  application  of  many  privacy  and  data  protection  laws  along  with  contractually  imposed 
industry standards are uncertain, it is possible that these laws may be interpreted and applied in a manner that is inconsistent with 
our  insurance  subsidiaries’  existing  data  management  practices  or  the  features  of  their  services  and  platform  capabilities.  Any 
failure or perceived failure by our insurance subsidiaries, or any third parties with which they do business, to comply with their 
posted privacy policies, changing consumer expectations, evolving laws, rules and regulations, industry standards, or contractual 
obligations  to  which  they  or  such  third  parties  are  or  may  become  subject,  may  result  in  actions  or  other  claims  against  our 

49

insurance subsidiaries by governmental entities or private actors, the expenditure of substantial costs, time and other resources or 
the incurrence of significant fines, penalties or other liabilities. In addition, any such action, particularly to the extent our insurance 
subsidiaries were found to be guilty of violations or otherwise liable for damages, would damage their reputation and adversely 
affect their business, financial condition and results of operations. Even if our businesses are not determined to have violated these 
laws, government investigations into these issues typically require the expenditure of significant resources and generate negative 
publicity, which could harm our businesses, financial condition, and results of operations.

Compliance with existing and new regulations affecting our business in regulated industries may increase costs and 

limit our ability to pursue business opportunities.

We  are  subject  to  extensive  laws  and  regulations  administered  and  enforced  by  a  number  of  different  federal  and  state 
governmental authorities in the industries in which we operate. Regulation of such industries may increase. In the past, there has 
been significant legislation affecting financial services and insurance, including the Dodd-Frank Act. In addition, we are subject to 
regulations governing the protection of personal confidential information and data security including the Gramm-Leach-Bliley Act, 
the GDPR, the NY DFS Cybersecurity Regulation and the CCPA. Accordingly, the impact that any new laws and regulations will 
have  on  us  is  unknown.  The  costs  to  comply  with  these  laws  and  regulations  may  be  substantial  and  could  have  a  significant 
negative impact on us and limit our ability to pursue business opportunities. We can give no assurances that with changes to laws 
and regulations, our businesses can continue to be conducted in each jurisdiction in the manner as we have in the past.

Our insurance subsidiaries are subject to regulation by state and, in some cases, foreign insurance authorities with respect 
to statutory capital, reserve and other requirements, including statutory capital and reserve requirements established by applicable 
insurance regulators based on RBC and Solvency II formulas. In any particular year, these requirements may increase or decrease 
depending on a variety of factors, most of which are outside our insurance subsidiaries’ control, such as the amount of statutory 
income  or  losses  generated,  changes  in  equity  market  levels,  the  value  of  fixed-income  and  equity  securities  in  our  investment 
portfolio, changes in interest rates and foreign currency exchange rates, as well as changes to the RBC formulas used by insurance 
regulators.  The  laws  of  the  various  states  in  which  our  insurance  businesses  operate  establish  insurance  departments  and  other 
regulatory agencies with broad powers to preclude or temporarily suspend our insurance subsidiaries from carrying on some or all 
of their activities or otherwise fine or penalize them in any jurisdiction in which they operate. Such regulation or compliance could 
reduce our insurance business’s profitability or limit their growth by increasing the costs of compliance, limiting or restricting the 
products  or  services  they  sell,  or  the  methods  by  which  they  sell  their  services  and  products,  or  subjecting  their  business  to  the 
possibility  of  regulatory  actions  or  proceedings.  Additionally,  increases  in  the  amount  of  additional  statutory  reserves  that  our 
insurance subsidiaries are required to hold could have a material adverse effect on their business, results of operations, financial 
condition and cash flows.

While the CFPB does not have direct jurisdiction over insurance products, it is possible that regulatory actions taken by 
the CFPB may affect the sales practices related to these products and thereby potentially affect our insurance business or the clients 
that  it  serves.  In  2017,  the  CFPB  issued  rules  under  its  unfair,  deceptive  and  abusive  acts  and  practices  rulemaking  authority 
relating  to  consumer  installment  loans,  among  other  things.  Such  CFPB  rules  regarding  consumer  installment  loans  could 
adversely impact our insurance business’s volume of insurance products and services and cost structure. Due to such regulatory 
actions,  some  lenders  may  reduce  their  sales  and  marketing  of  payment  protection  and  other  ancillary  products,  which  may 
adversely affect our insurance business’s revenues.

Due to the highly regulated nature of the residential mortgage industry, our mortgage subsidiaries are required to comply 
with a wide array of federal, state and local laws and regulations that regulate licensing, allowable fees and loan terms, permissible 
servicing  and  debt  collection  practices,  limitations  on  forced-placed  insurance,  special  consumer  protections  in  connection  with 
default and foreclosure, and protection of confidential, nonpublic consumer information. These laws and regulations are constantly 
changing  and  the  volume  of  new  or  modified  laws  and  regulations  has  increased  in  recent  years  as  states  and  local  cities  and 
counties  continue  to  enact  laws  that  either  restrict  or  impose  additional  obligations  in  connection  with  certain  loan  origination, 
acquisition and servicing activities in those cities and counties. These laws and regulations are complex and vary greatly among 
different states and localities, and in some cases, these laws are in conflict with each other or with U.S. federal law. A failure by us 
or our servicers to comply with applicable laws or regulations could subject our mortgage business and/or our mortgage servicers 
to  lawsuits  or  governmental  actions,  which  could  result  in  the  loss  or  suspension  of  our  licenses  in  the  applicable  jurisdictions 
where  such  violations  occur  and/or  monetary  fines  or  changes  in  our  mortgage  operations.  If  we  were  to  determine  to  change 
servicers,  there  is  no  assurance  that  we  could  find  servicers  that  satisfy  our  requirements  or  with  whom  we  could  enter  into 
agreements on satisfactory terms. Any of these outcomes could materially and adversely affect our mortgage business.

The CFPB continues to be active in its monitoring of the loan origination and servicing sectors, and its recently issued 

rules increase our regulatory compliance burden and associated costs.

50

Our  mortgage  business  is  subject  to  the  regulatory,  supervisory  and  examination  authority  of  the  CFPB,  which  has 
oversight of federal and state non-depository lending and servicing institutions, including residential mortgage originators and loan 
servicers. The CFPB has rulemaking authority with respect to many of the federal consumer protection laws applicable to mortgage 
lenders and servicers, including the Truth in Lending Act, the Real Estate Settlement Procedures Act and the Fair Debt Collections 
Practices Act. The CFPB has issued a number of regulations under the Dodd-Frank Act relating to loan origination and servicing 
activities, including ability to repay and "Qualified Mortgage" standards and other origination standards and practices.

The  CFPB’s  examinations  have  increased,  and  will  likely  continue  to  increase,  our  mortgage  business’s  administrative 
and  compliance  costs.  They  could  also  greatly  influence  the  availability  and  cost  of  residential  mortgage  credit  and  increase 
servicing costs and risks. These increased costs of compliance, the effect of these rules on the lending industry and loan servicing, 
and any failure in our mortgage business’s ability to comply with the new rules by their effective dates, could be detrimental to 
their business. The CFPB also issued guidelines on sending examiners to banks and other institutions that service and/or originate 
mortgages to assess whether consumers' interests are protected.

The CFPB also has broad enforcement powers, and can order, among other things, rescission or reformation of contracts, 
the refund of moneys or the return of real property, restitution, disgorgement or compensation for unjust enrichment, the payment 
of  damages  or  other  monetary  relief,  public  notifications  regarding  violations,  limits  on  activities  or  functions,  remediation  of 
practices, external compliance monitoring and civil money penalties. The CFPB has been active in investigations and enforcement 
actions and, when necessary, has issued civil money penalties to parties the CFPB determines has violated the laws and regulations 
it enforces. Our mortgage business’s failure to comply with the federal consumer protection laws, rules and regulations to which 
they are subject, whether actual or alleged, could expose them to enforcement actions or potential litigation liabilities.

Our insurance subsidiaries could be adversely affected if their controls to ensure compliance with guidelines, policies 

and legal and regulatory standards are not effective.

Our  insurance  business  is  highly  dependent  on  the  ability  of  our  insurance  subsidiaries  to  engage  on  a  daily  basis  in  a 
large  number  of  insurance  underwriting,  claim  processing  and  investment  activities,  many  of  which  are  highly  complex.  These 
activities often are subject to internal guidelines and policies, as well as legal and regulatory standards, including those related to 
privacy,  anti-corruption,  anti-bribery  and  global  finance  and  insurance  matters.  The  continued  expansion  into  new  products  and 
geographic markets has brought about additional requirements. A control system, no matter how well designed and operated, can 
provide only reasonable assurance that the control system’s objectives will be met. If our insurance subsidiaries’ controls are not 
effective, it could lead to financial loss, unanticipated risk exposure (including underwriting, credit and investment risk) or damage 
to their reputation.

Our businesses are subject to risks related to litigation and regulatory actions.

Over  the  last  several  years,  businesses  in  many  areas  of  the  financial  services  industry  have  been  subject  to  increasing 
amounts of regulatory scrutiny. In addition, there has been an increase in litigation involving firms in the financial services industry 
and public companies generally, some of which have involved new types of legal claims, particularly in the insurance industry. We 
may be materially and adversely affected by judgments, settlements, fines, penalties, unanticipated costs or other effects of legal 
and  administrative  proceedings  now  pending  or  that  may  be  instituted  in  the  future,  including  from  investigations  by  regulatory 
bodies  or  administrative  agencies.  An  adverse  outcome  of  any  investigation  by,  or  other  inquiries  from,  any  such  bodies  or 
agencies  also  could  result  in  non-monetary  penalties  or  sanctions,  loss  of  licenses  or  approvals,  changes  in  personnel,  increased 
review  and  scrutiny  of  us  by  our  clients,  counterparties,  regulatory  authorities,  potential  litigants,  the  media  and  others,  any  of 
which could have a material adverse effect on us.

We are involved in various litigation matters from time to time. For example, we are a defendant in Mullins v. Southern 
Financial  Life  Insurance  Co.,  a  class  action  lawsuit  alleging  violations  of  the  Consumer  Protection  Act  and  certain  insurance 
statutes,  as  well  as  common  law  fraud.  This  and  other  such  matters  can  be  time-consuming,  divert  management’s  attention  and 
resources and cause us to incur significant expenses. Our insurance and indemnities may not cover all claims that may be asserted 
against  us,  and  any  claims  asserted  against  us,  regardless  of  merit  or  eventual  outcome,  may  harm  our  reputation.  If  we  are 
unsuccessful in our defense in these litigation matters, or any other legal proceeding, we may be forced to pay damages or fines, 
enter into consent decrees or change our business practices, any of which could have a material adverse effect our business, results 
of operations, financial condition or cash flows.

Our international activities increase the compliance risks associated with economic and trade sanctions imposed by the 

United States, the EU and other jurisdictions.

51

Our international operations and activities expose us to risks associated with trade and economic sanctions, prohibitions or 
other restrictions imposed by the United States or other governments or organizations, including the United Nations, the EU and its 
member  countries.  Under  economic  and  trade  sanctions  laws,  governments  may  seek  to  impose  modifications  to,  prohibitions/
restrictions on business practices and activities, and modifications to compliance programs, which may increase compliance costs, 
and, in the event of a violation, may subject us to fines and other penalties.

We could be materially adversely affected by violations of the U.S. Foreign Corrupt Practices Act, the U.K. Bribery Act 

and anti-corruption laws in other applicable jurisdictions.

We  are  subject  to  anti-corruption,  anti-bribery,  anti-money  laundering  and  similar  laws  and  regulations  in  various 
jurisdictions in which we conduct business, including the U.S. Foreign Corrupt Practices Act and the U.K. Bribery Act 2010. We 
operate in countries known to present heightened risks for corruption and our dry bulk shipping and product tankers and related 
operations requires us to interact with government officials, including port officials, harbor masters, maritime regulators, customs 
officials and pilots.

Non-compliance  with  anti-corruption,  anti-bribery  or  anti-money  laundering  laws  could  subject  us  to  whistleblower 
complaints,  adverse  media  coverage,  investigations,  and  severe  administrative,  civil  and  criminal  sanctions,  collateral 
consequences, remedial measures and legal expenses, all of which could materially and adversely affect our business, results of 
operations, financial condition and reputation. 

Assessments and premium surcharges for state guaranty funds, secondary-injury funds, residual market programs and 

other mandatory pooling arrangements may reduce our insurance subsidiaries’ profitability.

Most  states  require  insurance  companies  licensed  to  do  business  in  their  state  to  participate  in  guaranty  funds,  which 
require the insurance companies to bear a portion of the unfunded obligations of impaired, insolvent or failed insurance companies. 
These  obligations  are  funded  by  assessments,  which  are  expected  to  continue  in  the  future.  State  guaranty  associations  levy 
assessments,  up  to  prescribed  limits,  on  all  member  insurance  companies  in  the  state  based  on  their  proportionate  share  of 
premiums written in the lines of business in which the impaired, insolvent or failed insurance companies are engaged. Accordingly, 
the  assessments  levied  on  our  insurance  subsidiaries  may  increase  as  they  increase  their  written  premiums.  These  funds  are 
supported by either assessments or premium surcharges based on incurred losses.

In  addition,  as  a  condition  to  conducting  business  in  some  states,  insurance  companies  are  required  to  participate  in 
residual  market  programs  to  provide  insurance  to  those  who  cannot  procure  coverage  from  an  insurance  carrier  on  a  negotiated 
basis.  Insurance  companies  generally  can  fulfill  their  residual  market  obligations  by,  among  other  things,  participating  in  a 
reinsurance pool where the results of all policies provided through the pool are shared by the participating insurance companies. 
Although  our  insurance  subsidiaries  price  their  insurance  to  account  for  their  potential  obligations  under  these  pooling 
arrangements,  they  may  not  be  able  to  accurately  estimate  their  liability  for  these  obligations.  Accordingly,  mandatory  pooling 
arrangements may cause a decrease in their profits. Further, the impairment, insolvency or failure of other insurance companies in 
these  pooling  arrangements  would  likely  increase  the  liability  for  other  members  in  the  pool.  The  effect  of  assessments  and 
premium  surcharges  or  increases  in  such  assessments  or  surcharges  could  reduce  our  insurance  subsidiaries’  profitability  in  any 
given period or limit the ability to grow their business.

Operation of dry bulk vessels and product tankers is subject to complex laws and regulations, including environmental 

laws and regulations that, if any of our vessel owner subsidiaries are found guilty of violation, can result in substantial fines 
and costs to the Company.

The  shipping  business  and  vessel  ownership  are  subject  to  government  regulation  in  the  form  of  international 
conventions, national, state and local laws, and regulations in force in the jurisdictions in which vessels operate, as well as in the 
country  or  countries  of  their  registration.  The  principal  international  convention  governing  marine  pollution  prevention  and 
response  is  the  International  Convention  for  the  Prevention  of  Pollution  from  Ships  (“MARPOL”).  MARPOL  regulates,  among 
other  things,  the  management  and  discharge  of  oil  and  garbage,  as  well  as  air  emissions  from  vessels  with  a  view  of  reducing 
pollution to the marine environment. One of MARPOL’s key requirements is that transfers and discharges of oily water must be 
recorded in an Oil Record Book. Similar requirements exist for garbage records and recording changeovers between high and low 
sulfur  fuel  due  to  the  impact  on  air  emissions.  The  Act  to  Prevent  Pollution  from  Ships,  33  U.S.C.  §  1901,  et  seq.  (“APPS”), 
implements MARPOL in the United States. The U.S. Coast Guard (“USCG”) is the responsible regulatory and enforcement agency 
and has promulgated regulations implementing APPS at 33 C.F.R. Part 151. Civil and administrative violations of APPS and the 
implementing USCG regulations may be enforced by the USCG, whereas criminal violations are enforced by the U.S. Department 
of Justice. 

52

Item 1B. Unresolved Staff Comments
None.

Item 1C. Cybersecurity

The  Company  has  adopted  processes  designed  to  identify,  assess  and  manage  material  risks  from  cybersecurity  threats.  Those 
processes  include  response  to  and  an  assessment  of  internal  and  external  threats  to  the  security,  confidentiality,  integrity  and 
availability of Company data and systems along with other material risks to our Company, at least annually or whenever there are 
material changes to the Company’s systems or operations. As part of our risk management process, the Company engages outside 
providers to conduct periodic internal and external penetration testing. Our information security management system is based upon 
industry leading frameworks, including CIS-18, ISO 27001, and NIST CSF. The Company stores Company data in cloud and local 
server environments with security appropriate to the data involved and has adopted controls around, among other things, vendor 
risk  assessment,  access  and  acceptable  use  and  backup  and  recovery.  We  have  implemented  security  monitoring  capabilities 
designed  to  alert  us  to  suspicious  activity  and  developed  an  incident  response  program  that  includes  periodic  testing  and  is 
designed  to  restore  business  operations  as  quickly  and  as  orderly  as  possible  in  the  event  of  a  breach.  In  addition,  employees 
participate  in  an  ongoing  program  of  mandatory  annual  training  and  receive  communications  regarding  the  cybersecurity 
environment  to  increase  awareness  throughout  the  Company.  The  Company  also  performs  periodic  cybersecurity  security 
assessments of our key vendors to help protect Company data when it leaves our network.

Operational  responsibility  for  overseeing  the  adequacy  and  effectiveness  of  the  Company’s  risk  management,  control  and 
governance processes is the responsibility of the Chief Operating Officer (“COO”) in consultation with senior management of the 
Company  and  the  Chief  Information  Security  Officers  (“CISO”)  of  the  Company  and  its  operating  subsidiaries.  Aspects  of  the 
information systems of the parent holding company and each material operating business are distinct so each has its own CISO, 
which  in  the  case  of  the  parent  holding  company  is  an  independent  third-party  service  provider.  The  CISOs’  expertise  in 
information  technology  and  cybersecurity  has  been  gained  from  a  combination  of  education,  including  relevant  degrees  and/or 
certifications, and prior work experience. Each of the CISOs has more than 10 years’ experience in information technology and 
cybersecurity. The COO reports regularly, and at least annually, to the Company’s Audit Committee and such report may address 
overall  assessment  of  the  Company’s  compliance  with  the  Company’s  cybersecurity  policies,  and  include  topics  such  as  risk 
assessment, risk management and control decisions, service provider arrangements, test results, security incidents and responses, 
and recommendations for changes and updates to policies and procedures. 

We  are  not  aware  of  any  material  risks  from  cybersecurity  threats,  that  have  materially  affected  or  are  reasonably  likely  to 
materially affect the Company, including our business strategy, results of operations or financial condition, but we cannot provide 
assurance that we will not be materially affected in the future by such risks or any future material incidents. See “Risk Factors-
Cybersecurity  attacks,  technology  breaches  or  failures  of  our  or  our  third-party  service  providers’  information  systems  could 
disrupt our various business operations and could result in the loss of critical and personally identifiable information, which could 
result in the loss of reputation and customers, reduce profitability, subject our businesses to fines, penalties and litigation and have 
a  material  adverse  effect  on  our  business’s  results  of  operation,  financial  condition  and  cash  flows”  for  additional  information 
regarding cybersecurity risks.

Item 2. Properties

Our  principal  executive  office  is  located  at  660  Steamboat  Road,  2nd  Floor,  Greenwich,  Connecticut  06830.  We  and  our 
subsidiaries lease properties throughout the United States and Europe, all of which are used as administrative offices. We believe 
that  the  terms  of  the  leases  at  each  of  our  subsidiaries  are  sufficient  to  meet  our  present  needs  and  we  do  not  anticipate  any 
difficulty in securing additional space, as needed, on acceptable terms.

Item 3. Legal Proceedings

Our legal proceedings are discussed under the heading “Litigation” in Note (21) — Commitments and Contingencies in the Notes 
to the consolidated financial statements in this report.

Item 4. Mine Safety Disclosures

Not applicable.

PART II

53

Item 5. Market for Registrant’s Common Equity, Related Stockholder Matters and Issuer Purchases of Equity Securities

Market Information
Tiptree’s common stock is traded on the Nasdaq Capital Market under the ticker symbol “TIPT”. 

Holders
As of December 31, 2023, there were 46 common stockholders of record. This number does not include beneficial owners whose 
shares are held by nominees in street name. 

Item 6. Reserved.

54

Item 7. Management’s Discussion and Analysis of Financial Condition and Results of Operations

Our Management’s Discussion and Analysis of Financial Condition and Results of Operations is presented in this section as 
follows:

•
•
•
•
•

Overview
Results of Operations
Non-GAAP Measures and Reconciliations
Liquidity and Capital Resources
Critical Accounting Policies and Estimates

OVERVIEW

Tiptree  allocates  capital  to  select  small  and  middle  market  companies  with  the  mission  of  building  long-term  value. 
Established  in  2007,  we  have  a  significant  track  record  investing  in  the  insurance  sector  and  across  a  variety  of  other 
industries,  including  mortgage,  specialty  finance  and  shipping.  Our  largest  operating  subsidiary,  Fortegra,  is  a  leading 
provider  of  specialty  insurance  products  and  related  services.  We  also  generate  earnings  from  a  diverse  group  of  select 
investments that we refer to as Tiptree Capital, which includes our Mortgage segment and other, non-insurance businesses 
and  assets.  We  evaluate  performance  primarily  by  the  comparison  of  stockholders’  long-term  total  return  on  capital,  as 
measured by growth in stock price plus dividends paid, in addition to Adjusted Net Income. 

Our 2023 highlights include:

Overall:

•

•

Tiptree reported net income of $14.0 million for the year ended December 31, 2023, compared to a net loss of $8.3 
million in the prior year period, driven by growth in insurance operations and the decrease in tax expense related to the 
tax  deconsolidation  of  Fortegra  from  $33.1  million  in  2022  to  $19.1  million  in  2023,  partially  offset  by  lower 
mortgage and shipping revenues. Return on average equity was 3.4%, compared to (2.1)% in 2022. 
Adjusted  net  income  of  $61.9  million  increased  $8.9  million  from  $53.0  million  in  2022,  driven  by  growth  in 
insurance operations. Adjusted return on average equity was 15.2%, as compared to 13.6% in 2022.

Insurance:

•

•

•

•

•

•

•

•

•

Gross written premiums and premium equivalents were $2.7 billion for the year ended December 31, 2023, an increase 
of $484.7 million, or 21.4%, from the prior year period as a result of growth in specialty E&S and admitted insurance 
lines in the U.S. and Europe, along with benefits from a book-roll transaction with one of Fortegra’s MGA partners.
Net written premiums were $1.3 billion for the year ended December 31, 2023, an increase of 21.2%, consistent with 
growth  in  gross  written  premiums,  and  as  a  result  of  increased  retention  on  Fortegra’s  whole  account  quota  share 
reinsurance arrangement from 30% to 40%, effective April 1, 2023.
Total revenues were $1.6 billion, an increase of $344.3 million, or 27.6%, from 2022, driven by premium growth in 
specialty E&S and admitted insurance lines in the U.S. and Europe, along with growth in net investment income. 
Combined ratio of 90.3%, driven by consistent underwriting performance and the scalability of Fortegra’s operating 
platform.
Income before taxes of $129.8 million as compared to $68.2 million in 2022. Return on average equity was 25.7% in 
2023  as  compared  to  14.6%  in  2022.  The  increases  were  driven  by  growth  in  underwriting  and  fee  revenues  and 
increased net investment income.
Adjusted net income (before NCI) was $115.7 million, an increase of $31.9 million, or 38.0%, from 2022. Adjusted 
return on average equity was 29.2%, as compared to 26.1% in 2022.
Fortegra’s total stockholders’ equity was $452.6 million as of December 31, 2023, compared to $338.7 million as of 
December  31,  2022,  with  the  increase  driven  by  net  income  during  the  year  as  well  as  an  improvement  in  the 
accumulated other comprehensive loss position, which was $31.1 million as of December 31, 2023, compared to $52.7 
million as of December 31, 2022.
As of December 31, 2023, Fortegra held an outstanding balance of $130.0 million on its revolving line of credit, as 
compared to a balance of $46.0 million as of September 30, 2023. The increase in borrowings was primarily to fund 
statutory capital requirements and general corporate purposes. 
In December 2023, Fortegra entered into a commutation agreement with a partner resulting in a reduction of policy 
liabilities and unpaid claims of $75.6 million relating to policies written in the 2020 and 2021 treaty years.

55

 
Tiptree Capital:

• Mortgage loss before taxes was $3.3 million for the year ended December 31, 2023, as compared to income of $0.9 

million in 2022, with the decrease driven by declines in origination volumes and negative fair value adjustments on the 
mortgage servicing portfolio.

Key Trends:

Our results of operations are affected by a variety of factors including, but not limited to, general economic conditions and 
GDP  growth,  market  liquidity  and  volatility,  consumer  confidence,  U.S.  demographics,  employment  and  wage  growth, 
business confidence and investment, inflation, interest rates and spreads, the impact of the regulatory environment, and the 
other factors set forth in Part I, Item 1A in the Annual Report on Form 10-K. Generally, our businesses are positively affected 
by  a  healthy  U.S.  consumer,  stable  to  gradually  rising  interest  rates,  stable  markets  and  business  conditions,  and  global 
growth and trade flows. Conversely, rising unemployment, volatile markets, rapidly rising interest rates, inflation, changing 
regulatory requirements and slowing business conditions can have a material adverse effect on our results of operations or 
financial condition.

Insurance  results  primarily  depend  on  pricing,  underwriting,  risk  retention  and  the  accuracy  of  reserves,  reinsurance 
arrangements,  returns  on  invested  assets,  and  policy  and  contract  renewals  and  run-off.  Factors  affecting  these  items, 
including conditions in financial markets, the global economy and the markets in which we operate, fluctuations in exchange 
rates, interest rates and inflation, including the current period of inflationary pressures, may have a material adverse effect on 
our  results  of  operations  or  financial  condition.  Fortegra  designs,  markets  and  underwrites  specialty  property  and  casualty 
insurance products for select target markets or niches. The types of products Fortegra offers tend to have limited aggregation 
risk  and  limited  exposure  to  catastrophic  and  residual  risk.  The  business  has  historically  generated  significant  fee-based 
revenues  by  incorporating  value-add  coverages  and  services.  Underwriting  risk  is  mitigated  through  a  combination  of 
reinsurance  and  sliding  scale  commission  structures  with  agents,  distribution  partners  and/or  third-party  reinsurers.  To 
mitigate  counterparty  risk,  Fortegra  ensures  its  reinsurance  receivables  are  placed  with  highly  rated  and  appropriately 
capitalized  counterparties  or  with  our  distribution  partners’  captive  insurance  vehicles  which  are  collateralized  with  highly 
liquid investments, cash or letters of credit. While Fortegra’s insurance operations have historically maintained a relatively 
stable  combined  ratio,  initiatives  to  change  the  business  mix  along  with  these  economic  factors  could  generate  different 
results than the business has historically experienced. In particular, rising inflation can have an impact on replacement costs 
associated  with  claims  from  our  customers  to  the  extent  we  are  unable  to  pass  the  higher  costs  of  claims  through  higher 
premiums.  In  addition,  fluctuations  of  the  U.S.  dollar  relative  to  other  currencies,  including  the  British  pound  and  Euro, 
would have an impact on book value between periods.

Fortegra’s investment portfolio includes fixed maturity securities, loans, credit investment funds, and equity securities. Many 
of those investments are held at fair value. In recent periods, the U.S. fixed income markets experienced a significant rise in 
interest rates. Rising interest rates have and could continue to impact the value of Fortegra’s fixed maturity securities, with 
any unrealized losses recorded in equity, and if realized, could impact our results of operations. Offsetting the impact of a 
rising interest rate environment, new investments in fixed rate instruments from both maturities and portfolio growth have 
and could continue to result in higher interest income on investments. The weighted average duration of our fixed income 
available for sale securities is less than three years. While our asset and liability mix is relatively matched, should we need to 
liquidate any of these investments before maturity to pay claims, any realized losses could materially negatively impact our 
results of operations. Changes in fair value for loans, credit investment funds, and equity securities in Fortegra’s investment 
portfolio are reported as unrealized gains or losses in revenues and can be impacted by changes in interest rates, credit risk, 
currency risk, or market risk, including specific company or industry factors. In addition, our equity holdings are relatively 
concentrated.  General  equity  market  trends,  along  with  company  and  industry  specific  factors,  can  impact  the  fair  value 
which can result in unrealized gains and losses affecting our results. 

Rising  10-year  treasury  yields,  and  the  tapering  of  the  Federal  Reserve’s  purchases  of  mortgage-backed  securities,  has 
resulted  in  substantial  increases  in  mortgage  interest  rates.  Low  mortgage  interest  rates  driven  by  the  Federal  Reserve 
intervention in mortgage markets, and rising home prices in certain markets, provided tailwinds to the mortgage markets in 
2020 and 2021, which benefited our mortgage operations and margins. The substantial rise in rates in recent periods resulted 
in a sharp reversal of those trends, with volumes and margins declining significantly. Only partially offsetting the declines in 
mortgage  originations  is  an  increase  in  the  fair  value  of  our  mortgage  servicing  portfolio  as  rising  rates  slow  prepayment 
speeds,  with  a  resulting  increase  in  servicing  income.  Continued  rising  or  elevated  mortgage  rates  could  have  a  materially 
negative  impact  on  our  mortgage  operations,  and  is  likely  to  be  only  partially  mitigated  by  the  improvement  in  mortgage 
servicing revenues. A sustained period of negative profitability in the mortgage industry could also impact the availability of 
funding sources for our mortgage business.

Rising interest rates can also impact the cost of floating interest rate debt obligations, while declining rates can decrease the 
cost of debt. Our secured revolving and term credit agreements, preferred trust securities and asset based revolving financing 
are all floating rate obligations. A continuation of rising rates could have a material impact on our costs of floating rate debt. 

56

RESULTS OF OPERATIONS

The  following  is  a  summary  of  our  consolidated  financial  results  for  the  years  ended  December  31,  2023  and  2022.  In 
addition  to  GAAP  results,  management  uses  the  Non-GAAP  measures  Adjusted  net  income,  Adjusted  return  on  average 
equity and book value per share as measurements of operating performance. Management believes these measures provide 
supplemental  information  useful  to  investors  as  they  are  frequently  used  by  the  financial  community  to  analyze  financial 
performance and comparison among companies. 

Adjusted Net Income and Adjusted Return on Average Equity. Adjusted net income is defined as income before taxes, less 
provision (benefit) for income taxes, and excluding the after-tax impact of various expenses that we consider to be unique and 
non-recurring  in  nature,  including  merger  and  acquisition  related  expenses,  stock-based  compensation,  net  realized  and 
unrealized gains (losses) and intangibles amortization associated with purchase accounting, all of which is reduced for non-
controlling interests. The calculation of adjusted net income excludes net realized and unrealized gains (losses) that relate to 
investments or assets rather than business operations. Adjusted net income is presented before the impacts of non-controlling 
interests. Adjusted return on average equity represents adjusted net income expressed on an annualized basis as a percentage 
of average beginning and ending stockholders’ equity during the period. Management uses adjusted net income and adjusted 
return on average equity as part of its capital allocation process and to assess comparative returns on invested capital. We 
believe adjusted net income provides additional clarity on the results of the Company’s underlying business operations as a 
whole  for  the  periods  presented  by  excluding  distortions  created  by  the  unpredictability  and  volatility  of  realized  and 
unrealized gains (losses). We also believe adjusted net income provides useful supplemental information to investors as it is 
frequently  used  by  the  financial  community  to  analyze  financial  performance  between  periods  and  for  comparison  among 
companies. 

Adjusted net income and adjusted return on average equity are not measurements of financial performance or liquidity under 
GAAP and should not be considered as an alternative or substitute for GAAP net income. See “Non-GAAP Reconciliations” 
for a reconciliation of these measures to their GAAP equivalents.

Selected Key Metrics

($ in thousands, except per share information)
GAAP:

Total revenues
Net income (loss) attributable to common stockholders
Diluted earnings per share
Cash dividends paid per common share
Return on average equity

Non-GAAP: (1)

Adjusted net income
Adjusted return on average equity
Book value per share

Year Ended December 31,

2023
$  1,649,031 
13,951 
$ 
0.33 
$ 
0.20 
$ 

 3.4 %

2022
$  1,397,752 
(8,274) 
$ 
(0.23) 
$ 
0.16 
$ 
 (2.1) %

$ 

$ 

61,917 

 15.2 %

11.34 

$ 

$ 

53,034 

 13.6 %

10.92 

(1) 

See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures. Adjusted	net	income	is	presented	after	the	impacts	of	non-controlling	interests.

Revenues

For the year ended December 31, 2023, revenues were $1,649.0 million, which increased $251.3 million, or 18.0%, compared 
to  the  prior  year  period.  The  changes  were  primarily  driven  by  growth  in  earned  premiums,  net,  and  service  and 
administrative fees in our insurance business, partially offset by lower mortgage and shipping revenues compared to the prior 
year periods.

The  table  below  provides  a  break  down  between  net  realized  and  unrealized  gains  and  losses  from  Invesque  and  other 
securities which impacted our consolidated results on a pre-tax basis. Many investments are carried at fair value and marked 
to market through unrealized gains and losses. As a result, we expect earnings related to these investments to be relatively 
volatile between periods. Fixed income securities are primarily marked to market through AOCI in stockholders’ equity and 
do not impact net realized and unrealized gains and losses until they are sold. 

57

($ in thousands)

Net realized gains - Maritime transportation
Net realized and unrealized gains (losses) - Invesque
Net realized and unrealized gains (losses)(1)
(1) 

Excludes Invesque, Maritime transportation and Mortgage realized and unrealized gains and losses.

Net Income (Loss) Attributable to common stockholders

Year Ended December 31,

2023

2022

$ 
$ 
$ 

—  $ 
(11,293)  $ 
(64)  $ 

34,803 
(19,360) 
(9,999) 

For the year ended December 31, 2023, the net income attributable to common stockholders was $14.0 million, compared to 
a  net  loss  of  $8.3  million  in  the  prior  year  period.  The  increase  was  driven  by  growth  in  Fortegra’s  underwriting  and  fee 
operations, and tax expense associated with the tax deconsolidation of Fortegra of $19.1 million in 2023, compared to $33.1 
million in 2022, partially offset by the gain on the sale of our vessels in 2022.

Adjusted net income & Adjusted return on average equity - Non-GAAP

Adjusted net income for the year ended December 31, 2023 was $61.9 million, an increase of $8.9 million, or 16.7%, from 
the year ended December 31, 2022, driven by growth in our insurance operations. For the year ended December 31, 2023, 
adjusted return on average equity was 15.2%, as compared to 13.6% for the year ended December 31, 2022, driven by the 
increase in adjusted net income.

Book Value per share - Non-GAAP

Total  stockholders’  equity  was  $576.6  million  as  of  December  31,  2023  compared  to  $533.6  million  as  of  December  31, 
2022,  with  the  increase  driven  by  comprehensive  income,  partially  offset  by  net  changes  in  non-controlling  interests  and 
dividends  paid.  In  the  year  ended  December  31,  2023,  Tiptree  returned  $7.3  million  to  common  stockholders  through 
dividends paid.

Book value per share for the period ended December 31, 2023 was $11.34, an increase from book value per share of $10.92 
as of December 31, 2022, driven by comprehensive income per share, partially offset by dividends paid of $0.20 per share, 
net changes in non-controlling interests and preferred dividends paid at Fortegra.

Results by Segment

We  classify  our  business  into  two  reportable  segments,  Insurance  and  Mortgage,  with  the  remainder  of  our  operations 
aggregated into Tiptree Capital - Other. Corporate activities include holding company interest expense, corporate employee 
compensation and benefits, and other expenses, including public company expenses.

58

The  following  tables  present  the  components  of  Revenue,  Income  (loss)  before  taxes  and  Adjusted  net  income  for  the 
following periods:

($ in thousands)

Revenues:
Insurance
Mortgage
Tiptree Capital - other
Corporate

Total revenues

Income (loss) before taxes:

Insurance
Mortgage
Tiptree Capital - other
Corporate

Total income (loss) before taxes

Non-GAAP - Adjusted net income: (1)

Insurance
Mortgage
Tiptree Capital - other
Corporate

Total adjusted net income

Year Ended December 31,

2023

2022

$ 

1,593,070  $ 
53,864 
2,097 
— 

$ 

1,649,031  $ 

1,248,796 
70,246 
78,710 
— 
1,397,752 

$ 

$ 

$ 

$ 

129,816  $ 
(3,285)   
(3,264)   
(40,214)   
83,053  $ 

91,963  $ 
(1,082)   
923 
(29,887)   
61,917  $ 

68,150 
874 
31,403 
(46,416) 
54,011 

73,465 
(4,658) 
13,627 
(29,400) 
53,034 

(1) 

See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures.

Insurance

Our  principal  operating  subsidiary,  Fortegra,  is  a  specialty  insurance  underwriter  and  service  provider,  which  focuses  on 
niche  lines  and  fee-oriented  services.  The  combination  of  specialty  insurance  underwriting,  service  contract  products,  and 
related service solutions delivered through a vertically integrated business model creates a blend of traditional underwriting 
revenues,  investment  income  and  unregulated  fee  revenues.  The  business  is  an  agent-driven  model,  distributing  products 
through  independent  insurance  agents,  consumer  finance  companies,  online  retailers,  auto  dealers,  and  regional  big  box 
retailers to deliver products that complement the consumer transaction.

As  of  December  31,  2023,  Fortegra  was  owned  approximately  79.5%  by  Tiptree,  17.5%  by  Warburg  and  3.0%  by 
management  and  directors  of  Fortegra,  before  giving  effect  to  the  exercise  of  outstanding  warrants  and  the  conversion  of 
outstanding  preferred  stock.  The  following  tables  and  discussion  present  the  Insurance  segment  results,  including  non-
controlling interests, for the year ended December 31, 2023 and 2022.

Components of our Results of Operations

Revenues

Earned Premiums, net represents the earned portion of gross written and assumed premiums, less the earned portion that is 
ceded  to  third-party  reinsurers  under  reinsurance  agreements.  Fortegra’s  insurance  policies  generally  have  a  term  of  six 
months to seven years depending on the underlying product and premiums are earned pro rata over the term of the policy. At 
the  end  of  each  reporting  period,  premiums  written  but  not  earned  are  classified  as  unearned  premiums  and  are  earned  in 
subsequent periods over the remaining term of the policy.

Service and Administrative Fees represent the earned portion of gross written premiums and premium equivalents, which is 
generated from non-insurance products including warranty service contracts, motor club contracts and other services offered 
as  part  of  Fortegra’s  vertically  integrated  product  offerings.  Such  fees  are  typically  positively  correlated  with  transaction 
volume and are recognized as revenue when realized and earned. At the end of each reporting period, gross written premiums 
and  premium  equivalents  written  for  service  contracts  not  earned  are  classified  as  deferred  revenue,  which  are  earned  in 
subsequent periods over the remaining term of the policy.

59

 
 
 
 
 
 
 
 
 
 
 
 
 
Ceding  Commissions  and  Other  Revenue  consists  of  commissions  earned  on  policies  written  on  behalf  of  third-party 
insurance companies with no exposure to the insured risk and certain fees earned in conjunction with underwriting policies. 
Other revenue also includes the interest income earned on the premium finance product offering.

Net  Investment  Income  represents  earned  investment  income  on  our  portfolio  of  invested  assets.  Our  invested  assets  are 
primarily comprised of fixed maturity securities, and may also include cash and cash equivalents and equity securities. The 
principal factors that influence net investment income are the size of our investment portfolio, the yield on that portfolio and 
expenses  due  to  external  investment  managers.  The  insurance  investment  portfolio  includes  investments  held  in  statutory 
insurance companies and in unregulated entities. The portfolios held in statutory insurance companies are subject to different 
regulatory considerations, including with respect to types of assets, concentration limits, affiliate transactions and the use of 
leverage.

Net Realized and Unrealized Gains (Losses) on investments are a function of the difference between the amount received by 
us on the sale of a security and the security’s cost-basis, as well as any “other-than-temporary” impairments and allowances 
for credit losses which are recognized in earnings. In addition, equity securities and certain other investments are carried at 
fair  value  with  unrealized  gains  and  losses  included  in  this  line.  Fortegra’s  investment  strategy  is  designed  to  achieve 
attractive  risk-adjusted  returns  across  select  asset  classes,  sectors  and  geographies  while  maintaining  adequate  liquidity  to 
meet claims payment obligations. As such, volatility from realized and unrealized gains and losses may impact period-over-
period performance. Unrealized gains and losses on equity securities and loans held at fair value impact current period net 
income, while unrealized gains and losses on AFS securities impact AOCI.

Expenses

Net Losses and Loss Adjustment Expenses represent actual insurance claims paid, changes in unpaid claim reserves, net of 
amounts  ceded  and  the  costs  of  administering  claims  for  insurance  lines.  Incurred  claims  are  impacted  by  loss  frequency, 
which is a measure of the number of claims per unit of insured exposure, and loss severity, which is based on the average size 
of claims. Factors affecting loss frequency and loss severity include the volume of underwritten contracts, changes in claims 
reporting patterns, claims settlement patterns, judicial decisions, economic conditions, morbidity patterns and the attitudes of 
claimants towards settlements, and original pricing of the product for purposes of the loss ratio in relation to loss emergence 
over time. Losses and loss adjustment expenses are based on an actuarial analysis of the estimated losses, including losses 
incurred during the period and changes in estimates from prior periods.

Member Benefit Claims represent the costs of services and replacement devices incurred in warranty and motor club service 
contracts.  Member  benefit  claims  represent  claims  paid  on  behalf  of  contract  holders  directly  to  third-party  providers  for 
roadside assistance and for the repair or replacement of covered products. Claims can also be paid directly to contract holders 
as a reimbursement payment, provided supporting documentation of loss is submitted to the Company. Claims are recognized 
as expense when incurred.

Commission Expenses reflect commissions paid to retail agents, program administrators and managing general underwriters, 
net  of  ceding  commissions  received  on  business  ceded  under  certain  reinsurance  contracts.  Commission  expenses  are 
deferred and amortized to expense in proportion to the premium earned over the policy life. Commission expense is incurred 
on most product lines. The majority of commissions are retrospective commissions paid to agents, distributors and retailers 
selling the Company’s products, including credit insurance policies, warranty service contracts and motor club memberships. 
When  claims  increase,  in  most  cases  distribution  partners  bear  the  risk  through  a  reduction  in  their  retrospective 
commissions.  Commission  rates  are,  in  many  cases,  set  by  state  regulators,  such  as  in  credit  and  collateral  protection 
programs and are also impacted by market conditions and the retention levels of distribution partners.

Operating and Other Expenses represent the general and administrative expenses of insurance operations including employee 
compensation and benefits and other expenses, including, technology costs, office rent, and professional services fees, such 
as legal, accounting and actuarial services.

Interest Expense consists primarily of interest expense on corporate revolving debt, notes, preferred trust securities due June 
15,  2037  (Preferred  Trust  Securities)  and  asset  based  debt  for  premium  finance  and  warranty  service  contract  financing, 
which is non-recourse to Fortegra. 

60

Depreciation  Expense  is  primarily  associated  with  furniture,  fixtures  and  equipment.  Amortization  Expense  is  primarily 
associated  with  purchase  accounting  amortization  including  values  associated  with  acquired  customer  relationships,  trade 
names and internally developed software and technology.

Key Performance Metrics

We discuss certain key performance metrics, described below, which provide useful information about our business and the 
operational factors underlying its financial performance.

Gross  written  premiums  and  premium  equivalents  represent  total  gross  written  premiums  from  insurance  policies  and 
warranty  service  contracts  issued  during  a  reporting  period.  They  represent  the  volume  of  insurance  policies  written  or 
assumed and warranty service contracts issued during a specific period of time without reduction for policy acquisition costs, 
reinsurance costs or other deductions. Gross written premiums is a volume measure commonly used in the insurance industry 
to compare sales performance by period. Premium equivalents are used to compare sales performance of warranty service and 
administrative contract volumes to gross written premiums. Similar to how management considers gross written premiums to 
be  a  relevant  measure  of  volume,  regardless  of  the  impact  of  reinsurance  on  net  earned  premiums,  management  considers 
premium  equivalents  to  be  a  relevant  measure  of  contract  volume,  regardless  of  whether  the  Company  retains  the  full 
obligation. Investors also use these measures to compare sales growth among comparable companies, while management uses 
these measures to evaluate the relative performance of various sales channels.

Net  written  premiums  are  gross  written  premiums  less  ceded  written  premiums.  Gross  written  premiums  are  the  amounts 
received, or to be received, for insurance policies written or assumed by us during a specific period of time without reduction 
for policy acquisition costs, reinsurance costs or other deductions. The volume of our gross written premiums in any given 
period is generally influenced by new business submissions, binding of new business submissions into policies, renewals of 
existing  policies,  and  average  size  and  premium  rate  of  bound  policies.  Ceded  written  premiums  are  the  amount  of  gross 
written  premiums  ceded  to  reinsurers.  We  enter  into  reinsurance  contracts  to  limit  our  exposure  to  potential  large  losses. 
Ceded  written  premiums  are  earned  over  the  reinsurance  contract  period  in  proportion  to  the  period  of  risk  covered.  The 
volume of our ceded written premiums is impacted by the level of our gross written premiums and any decision we make to 
increase or decrease retention levels, policy limits and co-participations.

Combined Ratio, Loss Ratio, Acquisition Ratio, Underwriting Ratio and Operating Expense Ratio

Combined ratio is an operating measure, which equals the sum of the underwriting ratio and the operating expense ratio. Loss 
ratio  is  the  ratio  of  the  GAAP  line  items  net  losses  and  loss  adjustment  expenses  and  member  benefit  claims  to  earned 
premiums,  net,  service  and  administrative  fees  (excluding  ceding  fees),  and  other  revenue  (excluding  cash  and  cash 
equivalent interest income). Acquisition ratio is the ratio of the GAAP line items commission expense (less ceding fees and 
ceding  commissions)  to  earned  premiums,  net,  service  and  administrative  fees  (excluding  ceding  fees),  and  other  revenue 
(excluding  cash  and  cash  equivalent  interest  income).  Underwriting  ratio  is  the  combination  of  the  loss  ratio  and  the 
acquisition ratio. Operating expense ratio is the ratio of the GAAP line items employee compensation and benefits and other 
expenses to earned premiums, net, service and administrative fees (excluding ceding fees) and other revenue (excluding cash 
and cash equivalent interest income). 

A combined ratio under 100% generally indicates an underwriting profit. A combined ratio over 100% generally indicates an 
underwriting  loss.  These  ratios  are  commonly  used  in  the  insurance  industry  as  a  measure  of  underwriting  profitability, 
excluding earnings on the insurance portfolio. Investors commonly use these measures to compare underwriting performance 
among companies separate from the performance of the investment portfolio. Management uses these measures to compare 
the profitability of various products we underwrite as well as profitability among our various agents and sales channels.

Return  on  average  equity  is  expressed  as  the  ratio  of  net  income  to  average  stockholders’  equity  during  the  period. 
Management uses this ratio as a measure of the on-going performance of the totality of the Company’s operations. 

Non-GAAP Financial Measures

Underwriting and Fee Revenues and Underwriting and Fee Margin

In order to better explain to investors the underwriting performance of the Company’s programs and the respective retentions 
between  the  Company  and  its  agents  and  reinsurance  partners,  we  use  the  non-GAAP  metrics  –  underwriting  and  fee 
revenues  and  underwriting  and  fee  margin.  We  generally  manage  our  exposure  to  the  risks  we  underwrite  using  both 
reinsurance  (e.g.,  quota  share  and  excess  of  loss)  and  sliding  scale  commission  agreements  with  our  agents  (e.g., 

61

commissions  paid  are  adjusted  based  on  the  actual  underlying  losses  incurred),  which  mitigates  our  risk.  Generally,  when 
losses are incurred, the risk which is retained by our agents and reinsurers is reflected in a reduction in commissions paid.

Underwriting and fee revenues represents earned premiums, net, service and administrative fees (excluding ceding fees) and 
other  income  (excluding  cash  and  cash  equivalent  interest  income).  We  reconcile  underwriting  and  fee  revenues  as  total 
revenues excluding net investment income, net realized gains (losses) and net unrealized gains (losses), ceding fees, ceding 
commissions and cash and cash equivalent interest income as reported in other income. See “—Non-GAAP Reconciliations” 
for a reconciliation of underwriting and fee revenues to total revenues in accordance with GAAP.

Underwriting and fee margin represents income before taxes excluding net investment income, net realized gains (losses), net 
unrealized  gains  (losses),  cash  and  cash  equivalent  interest  income,  employee  compensation  and  benefits,  other  expenses, 
interest expense and depreciation and amortization. We deliver our products and services on a vertically integrated basis to 
our agents. As such, underwriting and fee margin exclude general and administrative expenses, interest income, depreciation 
and  amortization  and  other  corporate  expenses,  including  income  taxes,  as  these  corporate  expenses  support  our  vertically 
integrated  delivery  model  and  are  not  specifically  supporting  any  individual  business  line.  See  “—Non-GAAP 
Reconciliations” for a reconciliation of underwriting and fee margin to total revenues in accordance with GAAP.

Adjusted  net  income  represents  income  before  taxes,  less  provision  (benefit)  for  income  taxes,  and  excluding  the  after-tax 
impact  of  various  expenses  that  we  consider  to  be  unique  and  non-recurring  in  nature,  including  merger  and  acquisition 
related  expenses,  stock-based  compensation,  net  realized  and  unrealized  gains  (losses),  and  intangibles  amortization 
associated with purchase accounting. 

Adjusted  return  on  average  equity  represents  adjusted  net  income  expressed  on  an  annualized  basis  as  a  percentage  of 
average beginning and ending stockholders’ equity during the period. 

Results of Operations - Year Ended December 31, 2023 compared to 2022

62

($ in thousands)

Revenues:

Earned premiums, net
Service and administrative fees
Ceding commissions
Net investment income
Net realized and unrealized gains (losses)
Other revenue

Total revenues

Expenses:

Net losses and loss adjustment expenses
Member benefit claims
Commission expense
Employee compensation and benefits
Interest expense
Depreciation and amortization
Other expenses

Total expenses

Income (loss) before taxes (1)

Key Performance Metrics:

Gross written premiums and premium equivalents
Net written premiums
Loss ratio
Acquisition ratio
Underwriting ratio
Operating expense ratio
Combined ratio
Return on average equity

Non-GAAP Financial Measures (2):
Adjusted net income (before NCI)
Adjusted return on average equity
Adjusted net income

2023

Year Ended December 31, 
Change

2022

% Change

 24.7 %
 23.5 %
 7.5 %
 118.3 %
 (79.3) %
 81.6 %
 27.6 %

 33.4 %
 31.1 %
 15.4 %
 30.1 %
 28.8 %
 15.5 %
 22.8 %
 23.9 %
 90.5 %

 21.4 %
 21.2 %

223,069 
75,249 
1,035 
14,455 
16,140 
14,326 
344,274 

120,905 
28,284 
80,347 
26,423 
5,782 
2,874 
17,993 
282,608 
61,666 

484,726 
230,558 

$  1,127,834 
395,969 
14,915 
26,674 
(4,207) 
31,885 
$  1,593,070 

$ 

904,765 
320,720 
13,880 
12,219 
(20,347) 
17,559 
$  1,248,796 

482,506 
119,288 
603,033 
114,341 
25,836 
21,425 
96,825 
$  1,463,254 
129,816 
$ 

361,601 
91,004 
522,686 
87,918 
20,054 
18,551 
78,832 
$  1,180,646 
68,150 
$ 

$  2,747,854 
$  1,319,948 

$  2,263,128 
$  1,089,390 

$ 

$ 

$ 
$ 

$ 
$ 

 40.1 %
 36.2 %
 76.3 %
 14.0 %
 90.3 %
 25.7 %

 37.7 %
 39.0 %
 76.7 %
 13.7 %
 90.4 %
 14.6 %

$ 

115,705 

 29.2 %

$ 

91,963 

$ 

$ 

83,832 

 26.1 %

73,465 

$ 

$ 

31,873 

 38.0 %

18,498 

 25.2 %

(1) 

(2) 

Net income was $101.3 million for the year ended December 31, 2023 compared to $46.4 million for the year ended December 31, 2022. 

See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures. 

Revenues - Year Ended December 31, 2023 compared to 2022

For the year ended December 31, 2023, total revenues increased 27.6%, to $1,593.1 million, as compared to $1,248.8 million 
for the year ended December 31, 2022. Earned premiums, net of $1,127.8 million increased $223.1 million, or 24.7%, driven 
by growth in specialty E&S and admitted insurance lines. Earned premiums assumed from other insurance companies were 
$404.7 million, or 35.9% of total earned premiums, net, compared to $310.4 million, or 34.3%, in the prior year period. As it 
expands to new geographies and expands product offerings, the Company works to obtain necessary licenses and intends to 
write this business directly upon obtaining necessary licenses. The Company views direct written and assumed business as 
having  similar  characteristics.  For  the  presented  periods,  earned  premiums,  net,  did  not  include  any  significant  regional 
geographic concentrations. Service and administrative fees of $396.0 million increased by 23.5% primarily driven by growth 
in vehicle service contract revenues. Ceding commissions of $14.9 million increased by $1.0 million, or 7.5%, in line with 
growth  in  ceded  premiums.  Other  revenues  increased  by  $14.3  million,  or  81.6%,  driven  by  growth  in  premium  finance 
product offerings and interest income on cash and cash equivalents. 

For the year ended December 31, 2023, 27.8% of revenues were derived from fees that were not solely dependent upon the 
underwriting  performance  of  Fortegra’s  insurance  products,  resulting  in  more  diversified  earnings.  For  the  year  ended 
December 31, 2023, 81.1% of fee-based revenues were generated in non-regulated service companies, with the remainder in 
regulated insurance companies.

63

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
For the year ended December 31, 2023, net investment income was $26.7 million as compared to $12.2 million in the prior 
year  period,  primarily  driven  by  growth  in  investments  and  the  increase  in  yields.  Net  realized  and  unrealized  losses  were 
$4.2 million, an improvement of $16.1 million, as compared to net realized and unrealized losses of $20.3 million in the prior 
year  period,  primarily  driven  by  the  change  in  fair  value  of  certain  equity  and  other  investments  carried  at  fair  value. 
Unrealized  gains  on  AFS  securities  impacting  OCI  for  the  year  ended  December  31,  2023  were  $19.0  million,  driven  by 
positive fair value adjustments on mortgage-backed securities and corporate bonds and other investments.

Expenses - Year Ended December 31, 2023 compared to 2022

For the year ended December 31, 2023, net losses and loss adjustment expenses were $482.5 million, member benefit claims 
were $119.3 million and commission expense was $603.0 million, as compared to $361.6 million, $91.0 million, and $522.7 
million,  respectively,  for  the  year  ended  December  31,  2022.  The  increase  in  net  losses  and  loss  adjustment  expenses  of 
$120.9 million, or 33.4%, was driven by growth in U.S. and European insurance lines and the shift in business mix toward 
commercial lines, which tend to have higher loss ratios and lower commission and expense ratios. In addition, the Company 
experienced  favorable  prior  year  development  of  $11.2  million  for  the  year  ended  December  31,  2023,  primarily  by  a 
commutation agreement with a partner resulting in a reduction of policy liabilities and unpaid claims of $75.6 million relating 
to  policies  written  in  the  2020  and  2021  treaty  years.  For  the  year  ended  December  31,  2022,  the  Company  experienced 
favorable  prior  year  development  of  $0.9  million,  primarily  as  a  result  of  lower-than-expected  claim  severity  in  our 
commercial lines of business. For the periods presented, net losses and adjustment expenses did not include any significant 
catastrophic  losses  or  regional  concentration  exposure.  The  increase  in  member  benefit  claims  of  $28.3  million,  or  31.1%, 
was  driven  by  growth  in  vehicle  service  contracts  and  the  impacts  of  inflation  on  replacement  costs  and  labor  rates. 
Commission expenses increased by $80.3 million, or 15.4%, generally in line with the growth in earned premiums, net and 
service and administrative fees, partially offset by the impacts from sliding scale commission structures.

For the year ended December 31, 2023, employee compensation and benefits were $114.3 million and other expenses were 
$96.8  million,  as  compared  to  $87.9  million  and  $78.8  million,  respectively,  for  the  year  ended  December  31,  2022. 
Employee compensation and benefits increased by $26.4 million, or 30.1%, driven by continued investment in data science, 
European platform expansion, and to support continued growth in the U.S. insurance business. Other expenses increased by 
$18.0  million,  or  22.8%,  driven  primarily  by  investment  in  data  science,  technology  and  marketing  expenses,  and 
professional fees associated with the acquisition of Premia.

For the year ended December 31, 2023, interest expense was $25.8 million as compared to $20.1 million for the year ended 
December 31, 2022. The increase in interest expense of $5.8 million, or 28.8%, was primarily driven by the rise in short-term 
interest rates and increased borrowings on Fortegra’s corporate revolver and asset based debt for premium finance lines.

For the year ended December 31, 2023, depreciation and amortization expense was $21.4 million, including $16.9 million of 
intangible  amortization  related  to  purchase  accounting  associated  with  the  acquisitions  of  Fortegra,  Smart  AutoCare,  Sky 
Auto,  ITC  and  Premia,  as  compared  to  $18.6  million,  including  $16.2  million  of  intangible  amortization  from  purchase 
accounting in 2022.

Gross Written Premiums and Premium Equivalents(1,2)

($ in thousands)

Property and short-tail
Contractual liability
General liability
Alternative risks
Professional liability
Europe

Commercial lines
Personal lines
Insurance

Auto and consumer goods warranty
Other services
Services
Total

Year Ended December 31, 
2022

2021

2023

$ 

$ 
$ 
$ 

$ 
$ 

548,984  $ 
396,861 
353,011 
330,171 
232,944 
141,208 
2,003,179  $ 
382,397  $ 
2,385,576  $ 
302,746
59,532

362,278  $ 
2,747,854  $ 

263,933  $ 
351,869 
305,325 
363,362 
82,340 
125,150 
1,491,979  $ 
397,423  $ 
1,889,402  $ 
318,550
55,176

373,726  $ 
2,263,128  $ 

100,462 
347,776
182,336
409,807
32,028
95,917
1,168,326 
432,522 
1,600,848 
285,591
49,535
335,126 
1,935,974 

64

 
 
 
 
 
 
 
 
 
 
(1) The total gross written premiums and premium equivalents of $2,747.9 million, $2,263.1 million and $1,936.0 million for the years ended December 31, 2023, 2022 and 2021, 
respectively, were comprised of gross written premiums of $1,896.5 million, $1,515.1 million and $1,380.1 million, plus assumed premiums of $489.1 million, $374.3 million and 
$220.7  million,  plus  gross  service  and  administrative  fee  additions  of  $362.3  million,  $373.7  million  and  $335.1  million.  See  Note  (8)  Reinsurance  Recoverable  and  Prepaid 
Reinsurance Premiums and Note (14) Revenue from Contracts with Customers within the respective periods for more information. 

(2) The premium equivalents metric excludes amounts received from failure to perform vehicle service contracts held in off-balance sheet trusts and premium finance volumes as it 
was  determined  to  be  unlikely  these  amounts  will  be  recognized  as  revenue.  Amounts  for  the  years  ended  December  31,  2022  and  2021  have  been  conformed  resulting  in  a 
reduction of premium equivalents of $418 million and $258 million, respectively. This change only impacted the premium equivalents metric and did not impact the Company’s 
financial statements, including its notes to the consolidated financial statements.

Total  gross  written  premiums  and  premium  equivalents  for  the  year  ended  December  31,  2023  were  $2,747.9  million, 
representing an increase of $484.7 million, or 21.4%. The growth is driven by a combination of factors including expanding 
Fortegra’s distribution partner network, growing specialty admitted and E&S insurance lines, and increasing penetration in 
the vehicle service contract sector.

For  the  year  ended  December  31,  2023,  Insurance  increased  by  $496.2  million,  or  26.3%,  driven  by  growth  in  specialty 
commercial lines, including E&S and admitted business. The year ended December 31, 2023, also benefited from a book-roll 
transaction of $125.1 million with one of Fortegra’s distribution partners. For the year ended December 31, 2023, Services 
decreased  by  $11.4  million,  or  3.1%,  driven  by  lower  volume  in  consumer  goods  and  vehicle  service  contracts,  partially 
offset by the acquisition of Premia.

The  combination  of  unearned  premiums  and  deferred  revenues  on  Fortegra’s  balance  sheet  grew  to  $2,368.1  million, 
representing an increase of $361.6 million, or 18.0%, from December 31, 2022 to December 31, 2023, as a result of growth 
in  gross  written  premiums  and  premium  equivalents,  primarily  related  to  E&S  and  admitted  insurance  lines,  including  the 
book roll transaction with one of Fortegra’s MGA partners.

Net written premiums

($ in thousands)

Property and short-tail
Contractual liability
General liability
Alternative risks
Professional liability
Europe

Commercial lines
Personal lines
Insurance

Year Ended December 31, 
2022

2021

2023

$ 

$ 
$ 
$ 

411,674  $ 
68,368 
163,567 
246,431 
84,380 
141,208 
1,115,628  $ 
204,320  $ 
1,319,948  $ 

188,069  $ 
100,338 
147,442 
268,775 
52,073 
125,150 
881,847  $ 
207,543  $ 
1,089,390  $ 

69,770 
109,345
94,617
313,805
25,028
95,917
708,482 
186,258 
894,740 

Net  written  premiums  for  the  year  ended  December  31,  2023  were  $1,319.9  million,  representing  an  increase  of  $230.6 
million,  or  21.2%,  driven  by  growth  in  commercial  E&S  lines.  For  the  year  ended  December  31,  2023,  commercial  lines 
increased  by  $233.8  million,  or  26.5%,  driven  by  growth  in  specialty  E&S  and  admitted  business,  including  a  book-roll 
transaction of $125.1 million with one of Fortegra’s distribution partners. For the year ended December 31, 2023, personal 
lines decreased by $3.2 million, or 1.6%, driven by declines in personal credit lines. Property and short-tail lines represented 
$411.7  million,  or  31.2%,  of  the  total  net  written  premiums  for  the  year  ended  December  31,  2023  compared  to  $188.1 
million,  or  17.3%,  for  the  prior  year  period.  Property  and  short-tail  net  written  premiums  were  diversified  by  geographic 
location,  exposure  and  risk  type  with  substantial  reinsurance  protection.  As  of  December  31,  2023,  the  net  loss  to  the 
Company  in  a  1-in-250  year  catastrophe  event  represented  approximately  2.4%  of  Fortegra’s  stockholders’  equity.  This 
reported  loss  includes  the  impact  of  incurred  losses  based  on  the  estimated  frequency  and  severity  of  potential  events, 
reinstatements premiums, reinsurance recoveries and taxes.

Combined Ratio

The  combined  ratio  was  90.3%  for  the  year  ended  December  31,  2023,  compared  to  90.4%  for  the  prior  year  period, 
reflecting  the  consistent  underwriting  performance  and  scalability  of  the  Company’s  operating  platform.  The  underwriting 
ratio was 76.3%, a decrease of 0.4% from the prior year period, which consists of a loss ratio of 40.1%, compared to 37.7% 
in the prior year period, and an acquisition ratio of 36.2%, compared to 39.0% in the prior year period. The loss ratio increase 
was  driven  by  a  shift  in  business  mix  towards  commercial  lines  and  increases  in  repair  and  labor  costs  on  vehicle  service 
contracts. The decrease in the acquisition ratio was driven by the shift in business mix toward commercial lines and impacts 
from sliding scale commission structures. The operating expense ratio was 14.0%, as compared to 13.7% in the prior year 

65

 
 
 
 
 
 
 
 
 
 
period. The increase in the operating expense ratio was a result of continued investment in data science, European platform 
expansion, and to support continued growth in U.S. insurance lines.

Underwriting and Fee Revenues and Margin - Non-GAAP 

The below table shows underwriting and fee revenues and underwriting and fee margin by business mix for the year ended 
December 31, 2023 and 2022.

($ in thousands)

Underwriting and Fee Revenues (1)

Net losses and loss adjustment expenses
Member benefit claims
Commission expense (2)

Underwriting and Fee Margin (1)

Insurance
$ 1,141,019 

  482,456 
— 
  411,012 
$ 247,551 

2023
Services
$ 359,004 

50 
  119,288 
  132,478 
$ 107,188 

Year Ended December 31,

Total
$ 1,500,023 

Insurance
$ 917,542 

  482,506 
  119,288 
  543,490 
$ 354,739 

  361,476 
— 
  371,638 
$ 184,428 

2022
Services
$ 282,843 

125 
91,004 
97,014 
$  94,700 

Total
$ 1,200,385 

  361,601 
91,004 
  468,652 
$ 279,128 

Loss ratio
Acquisition ratio
Underwriting ratio

 42.3 %
 36.0 %
 78.3 %

 33.2 %
 36.9 %
 70.1 %

 40.1 %
 36.2 %
 76.3 %

 39.4 %
 40.5 %
 79.9 %

 32.2 %
 34.3 %
 66.5 %

 37.7 %
 39.0 %
 76.7 %

See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures.

(1) 
(2)   Commission expense in this table is presented net of ceding fees and ceding commissions of $44.6 million and $14.9 million, respectively, for the year ended December 31, 

2023, and $40.2 million and $13.9 million, respectively, for  the year ended December 31, 2022. 

Underwriting and fee revenues were $1,500.0 million for the year ended December 31, 2023 as compared to $1,200.4 million 
for the year ended December 31, 2022. Total underwriting and fee revenues increased $299.6 million, or 25.0%, driven by 
growth in all business lines. The increase in insurance was $223.5 million, or 24.4%, driven by growth in specialty E&S and 
admitted insurance lines. The increase in services was $76.2 million, or 26.9%, driven by growth in vehicle service contracts 
and premium finance offerings, in addition to acquisitions of Premia in 2023 and ITC in 2022.

Underwriting and fee margin was $354.7 million for the year ended December 31, 2023 as compared to $279.1 million for 
the year ended December 31, 2022. Total underwriting and fee margin increased $75.6 million, or 27.1%, driven by growth 
in  all  product  lines.  Insurance  grew  by  $63.1  million,  or  34.2%,  driven  by  revenue  growth  in  specialty  E&S  and  admitted 
lines.  Services  increased  by  $12.5  million,  or  13.2%,  driven  by  growth  in  vehicle  service  contracts  and  the  acquisition  of 
Premia and ITC, partially offset by increased member benefit claims associated with the impacts of inflation on replacement 
costs and labor rates.

Return on Average Equity

Return  on  average  equity  was  25.7%  for  the  year  ended  December  31,  2023,  as  compared  to  14.6%  for  the  year  ended 
December 31, 2022. The increase in net income and annualized return on average equity was driven by revenue growth and 
consistent combined ratio, in addition to improvements in net investment income and net realized and unrealized gains and 
losses.

Adjusted Net Income and Adjusted Return on Average Equity - Non-GAAP

For the year ended December 31, 2023, adjusted net income (before NCI) and adjusted return on average equity were $115.7 
million  and  29.2%,  respectively,  as  compared  to  $83.8  million  and  26.1%,  respectively,  for  the  year  ended  December  31, 
2022.  The  improvement  of  adjusted  net  income  was  driven  by  the  growth  in  revenues  and  consistent  combined  ratio,  in 
addition to improvements in net investment income.

Tiptree Capital

Tiptree Capital consists of our Mortgage segment, which includes the operating results of Reliance, our mortgage business, 
and  Tiptree  Capital  -  Other,  which  consists  of  our  other  non-insurance  operating  businesses  and  investments.  As  of 
December 31, 2023, Tiptree Capital - Other includes our Invesque shares and other investments. 

66

 
 
 
 
 
 
 
Mortgage

Through our Mortgage operating subsidiary, Reliance, we originate, sell, securitize and service one-to-four-family, residential 
mortgage  loans,  comprised  of  conforming  mortgage  loans,  Federal  Housing  Administration  (“FHA”),  Veterans 
Administration (“VA”), United States Department of Agriculture (“USDA”), and to a lesser extent, non-agency jumbo prime.

We are an approved seller/servicer for Fannie Mae and Freddie Mac. We are also an approved issuer and servicer for Ginnie 
Mae. We originate residential mortgage loans through our retail distribution channel (directly to consumers) in 39 states and 
the District of Columbia as of December 31, 2023.

Components of our Results of Operations

Revenues

Net  Realized  and  Unrealized  Gains  (Losses)  include  gains  on  sale  of  mortgage  loans  and  the  fair  value  adjustment  in 
mortgage servicing rights. Gains on the sale of mortgage loans represent the difference between the selling price and carrying 
value of loans sold and are recognized upon settlement. Such gains also include the changes in fair value of loans held for 
sale and loan-related hedges and derivatives. We transfer the risk of loss or default to the loan purchaser, however, in some 
cases  we  are  required  to  indemnify  purchasers  for  losses  related  to  non-compliance  with  borrowers’  creditworthiness  and 
collateral requirements. Because of this, we recognize gains on sale net of required indemnification and premium recapture 
reserves.  The  fair  value  adjustment  on  mortgage  servicing  rights  represents  fair  value  adjustments  considering  estimated 
prepayments  and  other  factors  associated  with  changes  in  interest  rates,  plus  actual  run-off  in  the  servicing  portfolio.  We 
report these adjustments separate from servicing income and servicing expense.

Other  Revenue  includes  loan  origination  fees,  interest  income,  and  mortgage  servicing  income.  Loan  origination  fees  are 
earned  as  mortgage  loans  are  funded.  Servicing  fees  are  earned  over  the  life  of  the  loan.  Interest  income  includes  interest 
earned on loans held for sale and interest income on bank balances and short-term investments.

Expenses

Employee  Compensation  and  Benefits  includes  salaries,  commissions,  benefits,  bonuses,  other  incentive  compensation  and 
related taxes for employees. Commissions expense for sales staff generally varies with loan origination volumes.

Interest  Expense  represents  borrowing  costs  under  warehouse  and  other  credit  facilities  used  primarily  to  fund  loan 
originations. Amortization of deferred financing costs, including commitment fees, is included in interest expense.

Depreciation is mainly associated with furniture, fixtures and equipment. Amortization is primarily associated with a trade 
name and internally developed software.

Other Expenses include loan origination expenses, namely, leads, appraisals, credit reporting and licensing fees, general and 
administrative  expenses,  including  office  rent,  insurance,  legal,  consulting  and  payroll  processing  expenses,  and  servicing 
expense.

67

 
The following tables present the Mortgage segment results for the following periods:

Results of Operations

($ in thousands)

Revenues:

Net realized and unrealized gains (losses)
Other revenue

Total revenues

Expenses:

Employee compensation and benefits
Interest expense
Depreciation and amortization
Other expenses

Total expenses

Income (loss) before taxes

Key Performance Metrics:

Origination volumes
Gain on sale margins
Return on average equity

Non-GAAP Financial Measures (1):

Adjusted net income (1)
Adjusted return on average equity (1)

Year Ended December 31,

2023

2022

$ 

$ 

$ 

$ 
$ 

34,232 
19,632 
53,864 

34,040 
1,856 
617 
20,636 
57,149 
(3,285) 

$ 

$ 

$ 

$ 
$ 

51,345 
18,901 
70,246 

41,637 
1,631 
799 
25,305 
69,372 
874 

$ 

876,914 

$ 

1,134,351 

 4.7 %
 (4.6) %

 4.7 %
 0.9 %

$ 

(1,082) 

$ 

(4,658) 

 (2.0) %

 (8.1) %

(1) 

See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures.

Revenues - Year Ended December 31, 2023 compared to 2022

For the year ended December 31, 2023, $876.9 million of loans were funded, compared to $1,134.4 million for the prior year 
period,  a  decrease  of  $257.4  million,  or  22.7%,  driven  by  increase  in  mortgage  interest  rates  compared  to  the  prior  year 
period. Gain on sale margins remained consistent at 4.7% for the year ended December 31, 2023.

Net realized and unrealized gains for the year ended December 31, 2023 were $34.2 million, compared to $51.3 million in the 
prior  year  period,  a  decrease  of  $17.1  million  or  33.3%.  The  primary  driver  of  decreased  gain  on  sale  revenues  was  the 
decline  in  volumes  and  negative  fair  value  adjustment  in  mortgage  servicing  rights  of  $1.9  million  in  2023  compared  to  a 
positive fair value adjustment of $7.0 million in the prior year period.

Other revenue for the year ended December 31, 2023 was $19.6 million, compared to $18.9 million in the prior year period, 
an  increase  of  $0.7  million,  or  3.9%,  driven  by  increased  servicing  revenues.  As  of  December  31,  2023,  the  mortgage 
servicing asset was $40.8 million, a decrease from $41.4 million as of December 31, 2022.

Expenses - Year Ended December 31, 2023 compared to 2022 

For the year ended December 31, 2023, employee compensation and benefits were $34.0 million, compared to $41.6 million 
in the prior year period, a decrease of $7.6 million or 18.2%. The decrease was driven primarily by reduced commissions on 
lower origination volumes. 

For the year ended December 31, 2023, interest expense was at $1.9 million, an increase of $0.2 million, or 13.8%, with the 
increase driven by higher interest rates.

For  the  year  ended  December  31,  2023,  other  expenses  were  $20.6  million,  compared  to  $25.3  million  in  the  prior  year 
period,  a  decrease  of  $4.7  million,  with  the  decrease  driven  by  a  reduction  of  mortgage  operational  expenses,  including 
marketing costs.

68

 
 
 
 
 
 
 
 
Income (loss) before taxes

The  loss  before  taxes  for  the  year  ended  December  31,  2023  was  $3.3  million,  compared  to  income  before  taxes  of  $0.9 
million in the prior year period driven by a decline in volumes. 

Tiptree Capital - Other

The following tables present a summary of Tiptree Capital - Other results for the following periods:

Results of Operations

($ in thousands)

Senior living (Invesque)
Maritime transportation(1)
Other (2)
Total

Year Ended December 31, 

Total revenue

Income (loss) before taxes

2023

2022

2023

2022

$ 

$ 

(9,342)  $ 
842 
10,597 
2,097  $ 

(16,015)  $ 
64,947 
29,778 
78,710  $ 

(9,342)  $ 
(4,517)   
10,595 
(3,264)  $ 

(16,015) 
49,809 
(2,391) 
31,403 

(1) 

(2) 

Includes $5.4 million and $15.1 million of expenses related to our Maritime transportation operations for the years ended December 31, 2023 and 2022, respectively.
Includes asset management, our formerly held for sale mortgage originator (Luxury) for the year ended December 31, 2022, as it was deconsolidated on July 1, 2022, and 
certain intercompany elimination transactions.

Revenues

Tiptree Capital - Other earns revenues from the following sources: net interest income; revenues on our formerly held for sale 
mortgage  originator  (Luxury);  realized  and  unrealized  gains  and  losses  on  the  Company’s  investment  holdings  (including 
Invesque);  and  charter  revenues  from  vessels  within  the  Company’s  maritime  transportation  operations.  Subsequent  to  the 
sale of our dry bulk and tanker vessels, operations include two smaller vessels and other ancillary assets. 

Revenues for the year ended December 31, 2023 were $2.1 million compared to $78.7 million in the prior year period with 
the decline driven by the deconsolidation of Luxury effective July 1, 2022, and the sale of five vessels, partially offset by 
investment gains on securities in the Company’s investment holdings and decreased investment losses on Invesque in 2023 
compared to 2022.

Income (loss) before taxes

The loss before taxes from Tiptree Capital - Other for the year ended December 31, 2023 was $3.3 million, compared to the 
income  before  taxes  of  $31.4  million  in  the  prior  year  period.  The  decrease  was  driven  by  the  same  factors  that  impacted 
revenues.

Adjusted net income - Non-GAAP(1)

($ in thousands)

Senior living (Invesque)
Maritime transportation
Other
Total 

Year Ended December 31,

2023

2022

$ 

$ 

—  $ 

(2,769) 
3,692 

923  $ 

— 
12,707 
920 
13,627 

(1) 

See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures.

Adjusted net income decreased to $0.9 million for the year ended December 31, 2023 compared to $13.6 million in 2022. The 
decrease was driven from the sale of five vessels in 2022, partially offset by interest income on cash and cash equivalents and 
U.S. Treasury securities recorded in other income.

69

 
 
 
 
 
 
 
 
 
 
 
Corporate

The following table presents a summary of corporate results for the following periods:

Results of Operations

($ in thousands)

Employee compensation and benefits
Employee incentive compensation expense
Interest expense
Depreciation and amortization
Other expenses
Total expenses

Year Ended December 31,

2023

2022

$ 

$ 

8,885  $ 
21,230 
— 
1,327 
8,772 
40,214  $ 

7,948 
19,240 
4,225 
807 
14,196 
46,416 

Corporate expenses include expenses of the holding company for employee compensation and benefits, interest expense, and 
public company and other expenses. Corporate employee compensation and benefits includes the expense of management, 
legal and accounting staff. Other expenses primarily consisted of audit and professional fees, insurance, office rent and other 
related expenses.

Employee  compensation  and  benefits,  including  incentive  compensation  expense,  were  $30.1  million  for  the  year  ended 
December 31, 2023, compared to $27.2 million for the prior year period, driven by an increase in accrued bonus expense. Of 
the  incentive  compensation  expense  in  the  year  ended  December  31,  2023  and  2022,  $6.3  million  was  stock-based 
compensation expense. As of December 31, 2023, the Company had no outstanding borrowings at the holding company and 
therefore  incurred  no  interest  expense  for  the  year  ended  December  31,  2023  compared  to  $4.2  million  in  2022.  Other 
expenses of $8.8 million decreased by $5.4 million from the year ended December 31, 2022, primarily driven by decreased 
consulting and professional fees.

Provision for Income Taxes

The total income tax expense of $43.1 million for the year ended December 31, 2023 and $50.5 million for the year ended 
December 31, 2022 is reflected as a component of net income (loss). For the year ended December 31, 2023, the Company’s 
effective tax rate was equal to 51.8%. For the year ended December 31, 2022, the Company’s effective tax rate was equal to 
93.4%. The effective rates for the year ended December 31, 2023 and 2022 were significantly higher than the U.S. statutory 
income tax rate of 21.0%, primarily due to the impact of outside basis deferred taxes on Tiptree’s investment in Fortegra.

Tiptree  owns  less  than  80%  of  Fortegra  and  is  required  to  record  deferred  taxes  on  the  outside  basis  on  its  investment  in 
Fortegra. This deferred tax liability represents the tax that would be due, before consideration of loss carryforwards, if Tiptree 
were to sell all of its Fortegra stock at its carrying value on Tiptree’s balance sheet. 

As of December 31, 2023, this deferred tax liability relating to Fortegra was $61.7 million, which was an increase of $21.7 
million from the year ended December 31, 2022, of which $3.8 million expense was recorded in OCI, $1.2 million benefit 
was recorded directly in stockholders’ equity, and $19.1 million expense was recorded as a provision for income taxes. As of 
December  31,  2022,  this  deferred  tax  liability  was  $40.0  million,  of  which  $14.1  million  was  recorded  directly  in 
stockholders’ equity, a benefit of $2.4 million in other comprehensive income and $28.3 million as a provision for income 
taxes in the consolidated statements of operations for the year ended December 31, 2022. Additional one time impacts from 
the  transaction  incurred  in  2022  caused  $4.8  million  of  expense,  leading  to  $33.1  million  of  expense  in  the  statement  of 
operations. Excluding the impact of these deferred taxes, the effective tax rates for the twelve months ended December 31, 
2023 and 2022 were 28.8% and 32.1%, respectively.

On August 16, 2022, the U.S. government enacted Public Law no. 117-169, commonly referred to as the Inflation Reduction 
Act, which, among other things, establishes a corporate minimum tax on book earnings and an excise tax on stock buybacks. 
It is not expected that this legislation will have a material financial impact on the Company or its operations.

Balance Sheet Information

Tiptree’s  total  assets  were  $5.1  billion  as  of  December  31,  2023,  compared  to  $4.0  billion  as  of  December  31,  2022.  The 
$1,099.8 million increase in assets is primarily attributable to the growth in the Insurance segment. 

70

 
 
 
 
 
 
 
 
Total  stockholders’  equity  was  $576.6  million  as  of  December  31,  2023,  compared  to  $533.6  million  as  of  December  31, 
2022,  with  the  increase  primarily  driven  by  comprehensive  income  for  the  year  ended  December  31,  2023.  As  of 
December  31,  2023,  there  were  36,756,187  shares  of  common  stock  outstanding  as  compared  to  36,385,299  shares  as  of 
December  31,  2022,  with  the  increase  driven  by  the  vesting  of  share-based  incentive  compensation  and  the  exercise  of 
options.

The following table is a summary of certain balance sheet information:

As of December 31, 2023

Tiptree Capital

Insurance

Mortgage

Other

Corporate

4,835,685  $ 

160,147  $ 

126,624  $ 

16,857  $ 

Total
5,139,313 

$ 

290,000  $ 
67,138 

—  $ 

54,350 

—  $ 
— 

—  $ 
— 

290,000 
121,488 

$ 

292,914  $ 

52,297  $ 

125,819  $ 

(54,164)  $ 

416,866 

($ in thousands)
Total assets

Corporate debt
Asset based debt

Tiptree Inc. stockholders’ equity (1)
Non-controlling interests:
Fortegra preferred interests
Common interests

Total stockholders’ equity

$ 

77,679 
82,020 
452,613  $ 

— 
— 
52,297  $ 

— 
— 
125,819  $ 

— 
— 
(54,164)  $ 

77,679 
82,020 
576,565 

(1) 

Included in Corporate equity is the deferred tax liability on the outside basis on Tiptree’s investment in Fortegra of $61.7 million as of December 31, 2023. 

71

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
NON-GAAP MEASURES AND RECONCILIATIONS

Non-GAAP Reconciliations

In  addition  to  GAAP  results,  management  uses  the  non-GAAP  financial  measures  underwriting  and  fee  revenues  and 
underwriting and fee margin in order to better explain to investors the underwriting performance and the respective retentions 
between the Company and its agents and reinsurance partners. We also use the non-GAAP financial measures adjusted net 
income and adjusted return on average equity as measures of operating performance and as part of our resource and capital 
allocation  process,  to  assess  comparative  returns  on  invested  capital.  Management  believes  these  measures  provide 
supplemental  information  useful  to  investors  as  they  are  frequently  used  by  the  financial  community  to  analyze  financial 
performance  and  to  compare  relative  performance  among  comparable  companies.  Adjusted  net  income,  adjusted  return  on 
average  equity,  underwriting  and  fee  revenues  and  underwriting  and  fee  margin  are  not  measurements  of  financial 
performance or liquidity under GAAP and should not be considered as an alternative or substitute for earned premiums, net 
income or any other measure derived in accordance with GAAP.

Underwriting and Fee Revenues and Underwriting and Fee Margin — Non-GAAP (Insurance only)

Underwriting and Fee Revenues — Non-GAAP — We define underwriting and fee revenues as earned premiums, net, service 
and administrative fees (excluding ceding fees) and other income (excluding cash and cash equivalent interest income). We 
reconcile underwriting and fee revenues as total revenues excluding net investment income, net realized gains (losses) and net 
unrealized gains (losses), ceding fees, ceding commissions and cash and cash equivalent interest income as reported in other 
income.  Underwriting  and  fee  revenues  represents  revenues  generated  by  our  underwriting  and  fee-based  operations  and 
allows us to evaluate our underwriting performance without regard to investment income. We use this metric as we believe it 
gives our management and other users of our financial information useful insight into our underlying business performance. 
Underwriting and fee revenues should not be viewed as a substitute for total revenues calculated in accordance with GAAP, 
and other companies may define underwriting and fee revenues differently.

($ in thousands)

Total revenues
Less: Net investment income
Less: Net realized and unrealized gains (losses)
Less: Ceding fees (1)
Less: Ceding commissions
Less: Cash and cash equivalent interest income (2)

Underwriting and fee revenues (3)

Year Ended December 31,

2023
1,593,070  $ 
(26,674)   
4,207 
(44,628)   
(14,915)   
(11,037)   
1,500,023  $ 

2022
1,248,796 
(12,219) 
20,347 
(40,154) 
(13,880) 
(2,505) 
1,200,385 

$ 

$ 

(1) Ceding fees were included in service and administrative fees on the statement of operations. 
(2) Cash and cash equivalent interest income were included in other revenue on the statement of operations.
(3) Underwriting and fee revenues exclude ceding fees, ceding commissions and cash and cash equivalent interest income from other revenue. The year ended December 31, 2022 
has been conformed resulting in a reduction of underwriting and fee revenues of $56.5 million. This change only impacted the underwriting and fee revenues metric and did not 
impact the Company’s consolidated financial statements, including its notes to the consolidated financial statements.

Underwriting and Fee Margin — Non-GAAP — We define underwriting and fee margin as income before taxes, excluding 
net  investment  income,  net  realized  gains  (losses),  net  unrealized  gains  (losses),  cash  and  cash  equivalent  interest  income, 
employee compensation and benefits, other expenses, interest expense and depreciation and amortization. Underwriting and 
fee margin represents the underwriting performance of our underwriting and fee-based programs. As such, underwriting and 
fee  margin  excludes  general  administrative  expenses,  interest  expense,  depreciation  and  amortization  and  other  corporate 
expenses  as  those  expenses  support  the  vertically  integrated  business  model  and  not  any  individual  component  of  our 
business mix. We use this metric as we believe it gives our management and other users of our financial information useful 
insight into the specific performance of our underlying underwriting and fee programs. Underwriting and fee income should 
not be viewed as a substitute for income before taxes calculated in accordance with GAAP, and other companies may define 
underwriting and fee margin differently.

72

 
 
 
 
 
 
($ in thousands)

Income (loss) before income taxes
Less: Net investment income
Less: Net realized and unrealized gains (losses)
Less: Cash and cash equivalent interest income (1)
Plus: Depreciation and amortization
Plus: Interest expense
Plus: Employee compensation and benefits
Plus: Other expenses

Underwriting and fee margin (2)

Year Ended December 31,

2023

2022

$ 

$ 

129,816  $ 
(26,674)   
4,207 
(11,037)   
21,425 
25,836 
114,341 
96,825 
354,739  $ 

68,150 
(12,219) 
20,347 
(2,505) 
18,551 
20,054 
87,918 
78,832 
279,128 

(1) Cash and cash equivalent interests income were included in other revenue on the statement of operations.
(2)  Underwriting  and  fee  margin  exclude  the  cash  and  cash  equivalent  interest  income.  The  year  ended  December  31,  2022  has  been  conformed  resulting  in  a  reduction  of 
underwriting  and  fee  margin  of  $2.5  million.  This  change  only  impacted  the  underwriting  and  fee  margin  metric  and  did  not  impact  the  Company’s  consolidated    financial 
statements, including its notes to the consolidated financial statements.

Adjusted Net Income — Non-GAAP

We define adjusted net income as income before taxes, less provision (benefit) for income taxes, and excluding the after-tax 
impact  of  various  expenses  that  we  consider  to  be  unique  and  non-recurring  in  nature,  including  merger  and  acquisition 
related  expenses,  stock-based  compensation,  net  realized  and  unrealized  gains  (losses)  and  intangibles  amortization 
associated  with  purchase  accounting,  all  of  which  is  reduced  for  non-controlling  interests.  The  calculation  of  adjusted  net 
income excludes net realized and unrealized gains (losses) that relate to investments or assets rather than business operations. 
Adjusted net income should not be viewed as a substitute for income before taxes calculated in accordance with GAAP, and 
other  companies  may  define  adjusted  net  income  differently.  Adjusted  net  income  (before  NCI)  is  presented  before  the 
impacts of non-controlling interests. 

We present adjustments for amortization associated with acquired intangible assets. The intangible assets were recorded as 
part of purchase accounting in connection with Tiptree’s acquisition of Fortegra Financial in 2014, Defend in 2019, Smart 
AutoCare, Sky Auto in 2020, ITC in 2022 and Premia in 2023. The intangible assets acquired contribute to overall revenue 
generation, and the respective purchase accounting adjustments will continue to occur in future periods until such intangible 
assets are fully amortized in accordance with the respective amortization periods required by GAAP.

Adjusted Return on Average Equity — Non-GAAP

We  define  adjusted  return  on  average  equity  as  adjusted  net  income  expressed  on  an  annualized  basis  as  a  percentage  of 
average  beginning  and  ending  stockholders’  equity  during  the  period.  See  “—Adjusted  Net  Income—Non-GAAP”  above. 
Adjusted return on average equity should not be viewed as a substitute for return on average equity calculated in accordance 
with GAAP, and other companies may define adjusted return on average equity differently. 

73

 
 
 
 
 
 
 
 
 
 
 
 
($ in thousands)

Income (loss) before taxes
Less: Income tax (benefit) expense
Less: Net realized and unrealized gains (losses) (1)
Plus: Intangibles amortization (2)
Plus: Stock-based compensation expense
Plus: Non-recurring expenses (3)
Plus: Non-cash fair value adjustments (4)
Plus: Impact of tax deconsolidation of Fortegra (5)
Less: Tax on adjustments (6)

Adjusted net income (before NCI)
Less: Impact of non-controlling interests

Adjusted net income 

Adjusted net income (before NCI)

Average stockholders’ equity

Adjusted return on average equity (7)

($ in thousands)

Income (loss) before taxes
Less: Income tax (benefit) expense
Less: Net realized and unrealized gains (losses) (1)
Plus: Intangibles amortization (2)
Plus: Stock-based compensation expense
Plus: Non-recurring expenses (3)
Plus: Non-cash fair value adjustments (4)
Plus: Impact of tax deconsolidation of Fortegra (5)
Less: Tax on adjustments (6)

Adjusted net income (before NCI)
Less: Impact of non-controlling interests

Adjusted net income 

Adjusted net income (before NCI)

Average stockholders’ equity

Adjusted return on average equity (7)

Year Ended December 31, 2023
Tiptree Capital

Mortgage

Other

Corporate

Total

(3,285) 
837 
1,861 
— 
— 
— 
— 
— 
(495) 
(1,082) 
— 
(1,082) 

(1,082) 
53,520 

 (2.0) %

$ 

$ 

$ 

$ 
$ 

(3,264) 
153 
5,289 
— 
— 
— 
— 
— 
(1,255) 
923 
— 
923 

923 
100,325 

 0.9 %

$ 

$ 

$ 

$ 
$ 

(40,214)  $ 
(15,822) 
— 
— 
6,251 
— 
— 
19,101 
797 
(29,887)  $ 
— 
(29,887)  $ 

83,053 
(43,056) 
11,357 
16,919 
8,269 
2,824 
(1,769) 
19,101 
(11,039) 
85,659 
(23,742) 
61,917 

(29,887)  $ 
5,564  $ 
NM%

85,659 
555,070 

 15.4 %

Year Ended December 31, 2022
Tiptree Capital

Mortgage
874 
(363) 
(7,003) 
— 
— 
— 
— 
— 
1,834 
(4,658) 
— 
(4,658) 

(4,658) 
57,575 

Other

31,403 
(5,545) 
(18,788) 
— 
— 
(729) 
3,555 
— 
3,731 
13,627 
— 
13,627 

13,627 
98,373 

$ 

$ 
$ 
$ 

$ 
$ 

Corporate
(46,416) 
(23,291) 
— 
— 
7,093 
2,108 
— 
31,573 
(467) 
(29,400) 
— 
(29,400) 

(29,400) 
(10,390) 

$ 

$ 
$ 
$ 

$ 
$ 

Total

54,011 
(50,450) 
(5,444) 
16,229 
9,516 
4,753 
2,616 
33,133 
(963) 
63,401 
(10,367) 
53,034 

63,401 
466,878 

$ 

$ 

$ 

$ 
$ 

Insurance
129,816 
(28,224) 
4,207 
16,919 
2,018 
2,824 
(1,769) 
— 
(10,086) 
115,705 
(23,742) 
91,963 

115,705 
395,661 

 29.2 %

Insurance
68,150 
(21,251) 
20,347 
16,229 
2,423 
3,374 
(939) 
1,560 
(6,061) 
83,832 
(10,367) 
73,465 

83,832 
321,320 

$ 

$ 

$ 

$ 
$ 

$ 

$ 

$ 

$ 
$ 

$ 

$ 

$ 

$ 
$ 

$ 

$ 
$ 
$ 

$ 
$ 

 26.1 %

 (8.1) %

 13.9 %

NM%

 13.6 %

The footnotes below correspond to the tables above, under “—Adjusted Net Income - Non-GAAP” and “—Adjusted Return on Average Equity - Non-GAAP”.
(1) Net realized and unrealized gains (losses) added back in Adjusted net income excludes net realized and unrealized gains (losses) from the mortgage segment, those relating to 
our held-for-sale mortgage originator (Luxury), and unrealized gains (losses) on mortgage servicing rights.
(2) Specifically associated with acquisition purchase accounting. See Note (9) Goodwill and Intangible Assets, net.
(3) For the year ended December 31, 2023 and 2022, included in other expenses were expenses related to banker and legal fees associated with the acquisitions of Premia and ITC.
(4) For the year ended December 31, 2023 and 2022. non-cash fair-value adjustments represent a change in fair value of the Fortegra Additional Warrant liability which are added-
back to adjusted net income. For the 2022 periods, maritime transportation depreciation and amortization was deducted as a reduction in the value of the vessels.
(5) For the year ended December 31, 2023 and 2022, included in the adjustment is an add-back of $19.1 million and $33.1 million, respectively,  related to deferred tax expense 
from the WP Transaction.
(6) Tax on adjustments represents the tax applied to the total non-GAAP adjustments and includes adjustments for non-recurring or discrete tax impacts.
(7) Total Adjusted return on average equity after non-controlling interests was 15.2% and 13.6% for the years ended December 31, 2023 and 2022, respectively, based on $61.9 
million and $53.0 million of Adjusted net income over $407.1 million and $390.2 million of average Tiptree Inc. stockholders’ equity.

Book Value per share - Non-GAAP

Management believes the use of this financial measure provides supplemental information useful to investors as book value is 
frequently  used  by  the  financial  community  to  analyze  company  growth  on  a  relative  per  share  basis.  The  following  table 
provides a reconciliation between total stockholders’ equity and total shares outstanding, net of treasury shares.

74

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 ($ in thousands, except per share information)

Total stockholders’ equity

Less: Non-controlling interests
Total stockholders’ equity, net of non-controlling interests

Total common shares outstanding

Book value per share

LIQUIDITY AND CAPITAL RESOURCES

As of December 31, 
2022
2023

$ 

$ 

576,565  $ 
159,699 
416,866  $ 

533,573 
136,208 
397,365 

36,756 

36,385 

$ 

11.34  $ 

10.92 

Our principal sources of liquidity are unrestricted cash, cash equivalents and other liquid investments and distributions from 
operating subsidiaries, including income from our investment portfolio and sales of assets and investments. We intend to use 
our cash resources to continue to fund our operations and grow our businesses. We may seek additional sources of cash to 
fund  acquisitions  or  investments.  These  additional  sources  of  cash  may  take  the  form  of  debt  or  equity  and  may  be  at  the 
parent,  subsidiary  or  asset  level.  We  are  a  holding  company  and  our  liquidity  needs  are  primarily  for  compensation, 
professional fees, office rent and insurance costs. 

Our  subsidiaries’  ability  to  generate  sufficient  net  income  and  cash  flows  to  make  cash  distributions  will  be  subject  to 
numerous business and other factors, including restrictions contained in agreements for the strategic investment by Warburg 
in  Fortegra,  our  subsidiaries’  financing  agreements,  regulatory  restrictions,  availability  of  sufficient  funds  at  such 
subsidiaries, general economic and business conditions, tax considerations, strategic plans, financial results and other factors 
such as target capital ratios and ratio levels anticipated by rating agencies to maintain or improve current ratings. We expect 
our cash and cash equivalents and distributions from operating subsidiaries, our subsidiaries’ access to financing, and sales of 
investments to be adequate to fund our operations for at least the next 12 months, as well as the long term.

As  of  December  31,  2023,  cash  and  cash  equivalents,  excluding  restricted  cash,  were  $468.7  million,  compared  to  $538.1 
million at December 31, 2022, a decrease of $69.4 million, primarily driven by an increase in investments.

Our mortgage business relies on short term uncommitted sources of financing as a part of their normal course of operations. 
To  date,  we  have  been  able  to  obtain  and  renew  uncommitted  warehouse  credit  facilities.  If  we  were  not  able  to  obtain 
financing, then we may need to draw on other sources of liquidity to fund our mortgage business. See Note (11) Debt, net in 
the notes to consolidated financial statements, for additional information regarding our mortgage warehouse borrowings. 

We believe that cash flow from operations will provide sufficient capital to continue to grow the business and fund interest on 
the outstanding debt, capital expenditures and other general corporate needs over the next several years. As we continue to 
expand our business, including by any acquisitions we may make, we may, in the future, require additional working capital 
for increased costs.

For purposes of determining enterprise value, we consider corporate credit agreements and preferred trust securities, which 
we refer to as corporate debt, as corporate financing and associated interest expense is added back. The below table outlines 
this amount by debt outstanding and interest expense at the insurance company and corporate level.

Corporate Debt

($ in thousands)

Insurance
Corporate
Total 

Corporate Debt Outstanding 
as of December 31, 
2022

2023

Interest Expense for the year 
ended December 31, 
2022
2023

$ 

$ 

290,000  $ 
— 
290,000  $ 

160,000  $ 
— 
160,000  $ 

19,531  $ 
— 
19,531  $ 

14,675 
4,615 
19,290 

The balance of the corporate credit facility was repaid during June 2022 as part of the WP Transaction. See Note (11) Debt, 
net in the notes to consolidated financial statements for details for prior periods.

75

 
 
 
 
 
 
 
 
As of December 31, 2023 and 2022, a total of $130.0 million and $0, respectively, was outstanding under the revolving line 
of credit in our insurance business. The maximum borrowing capacity under the agreements as of December 31, 2023 and 
2022  was  $200.0  million.  The  increase  in  borrowings  was  primarily  to  fund  statutory  capital  requirements  and  general 
corporate purposes. 

On October 21, 2022, a subsidiary of Fortegra entered into a Second Amended and Restated Credit Agreement by and among 
Fortegra,  and  its  subsidiary,  LOTS  Intermediate  Co.,  as  borrowers,  the  lenders  from  time  to  time  party  thereto,  certain  of 
Fortegra’s  subsidiaries,  as  guarantors,  and  Fifth  Third  Bank,  National  Association,  as  the  administrative  agent  and  issuing 
lender  (the  “Fortegra  Credit  Agreement”).  The  Fortegra  Credit  Agreement  provides  for  a  $200.0  million  revolving  credit 
facility, all of which is available for the issuance of letters of credit, with a sub-limit of $25.0 million for swing loans and 
matures on October 1, 2027.

Consolidated Comparison of Cash Flows

($ in thousands)

Cash and cash equivalents provided by (used in):

Operating activities
Investing activities
Financing activities
Effect of exchange rate changes on cash

Change in cash, cash equivalents and restricted cash

Operating Activities

Year Ended December 31,

2023

2022

$ 

71,452  $ 

(244,669) 
113,406 
1,525 
(58,286)  $ 

$ 

463,073 
9,514 
(115,186) 
(1,828) 
355,573 

Cash provided by operating activities was $71.5 million for the year ended December 31, 2023. In 2023, the primary sources 
of cash from operating activities included growth in insurance premiums written resulting in increases in deferred revenues, 
unearned  premiums,  policy  liabilities  and  unpaid  claims,  reinsurance  payables  and  other  liabilities  and  accrued  expenses 
which  were  partially  offset  by  increases  in  notes  and  accounts  receivable,  reinsurance  recoverable  and  prepaid  reinsurance 
premiums.

Cash  provided  by  operating  activities  was  $463.1  million  for  the  year  ended  December  31,  2022.  In  2022,  the  primary 
sources  of  cash  from  operating  activities  included  proceeds  from  mortgage  loans  outpacing  originations  and  growth  in 
insurance  premiums  written  resulting  in  increases  in  unearned  premiums,  policy  liabilities  and  unpaid  claims  and  deferred 
revenues,  which  were  partially  offset  by  increases  in  deferred  acquisition  costs,  reinsurance  recoverable  and  prepaid 
reinsurance premiums.

Investing Activities 

Cash used in investing activities was $244.7 million for the year ended December 31, 2023. In 2023, the primary uses of cash 
were the purchases of investments outpacing the proceeds from the sale of investments, as well as the acquisition of Premia.

Cash provided by investing activities was $9.5 million for the year ended December 31, 2022. In 2022, the primary sources of 
cash were the proceeds of sales and maturities of investments outpacing the purchases of investments offset by the acquisition 
of ITC.

Financing Activities

Cash provided by financing activities was $113.4 million for the year ended December 31, 2023. In 2023, the cash provided 
was  primarily  proceeds  from  corporate  borrowings  at  Fortegra  and  mortgage  warehouse  facilities  which  exceeded 
repayments, partially offset by non-controlling interests distributions and the payment of common and preferred dividends.

Cash used in financing activities was $115.2 million for the year ended December 31, 2022. In 2022, principal repayments on 
mortgage warehouse facilities exceeded proceeds from borrowings, which was partially offset by cash received from the WP 
Transaction and the exercise of warrants.

CRITICAL ACCOUNTING POLICIES AND ESTIMATES

76

 
 
 
 
 
 
The  Company’s  significant  accounting  policies  are  described  in  Note  (2)  Summary  of  Significant  Accounting  Policies.  As 
disclosed  in  Note  (2),  the  preparation  of  financial  statements  in  conformity  with  GAAP  requires  management  to  make 
estimates and assumptions about future events that affect the amounts reported in the financial statements and accompanying 
notes. Actual results could differ significantly from those estimates.

The Company believes that the following discussion addresses the Company’s most critical accounting policies, which are 
those  that  are  most  important  to  the  portrayal  of  the  Company’s  financial  condition  and  results  of  operations  and  require 
management’s most difficult, subjective and complex judgments.

Impairment

Goodwill and Intangible Assets, net

The initial measurement of goodwill and intangibles requires judgment concerning estimates of the fair value of the acquired 
assets  and  liabilities.  Goodwill  and  indefinite-lived  intangible  assets  are  not  amortized  but  subject  to  tests  for  impairment 
annually or if events or circumstances indicate it is more likely than not they may be impaired. Finite-lived intangible assets 
are  subject  to  impairment  if  events  or  circumstances  indicate  a  possible  inability  to  realize  the  carrying  amount.  At  both 
December  31,  2023  and  2022,  we  had  two  reporting  units  for  goodwill  impairment  testing,  of  which  the  fair  value 
substantially exceeded carrying value as of that date. See Note (9) Goodwill and Intangible Assets, net.

Reserves

Unpaid claims are reserve estimates that include an amount determined from individual case estimates and loss reports, and 
an  amount,  based  on  past  experience,  for  losses  incurred  but  not  reported  (IBNR)  that  are  established  in  accordance  with 
GAAP  using  generally  accepted  actuarial  methods.  The  Company  uses  a  number  of  algorithms  in  establishing  its  unpaid 
claims reserves. These algorithms are used to calculate unpaid claims as a function of paid losses, earned premiums, target 
loss  ratios,  in-force  amounts,  unearned  premium  reserves,  industry  recognized  morbidity  tables  or  a  combination  of  these 
factors. 

In  arriving  at  the  IBNR  reserves,  the  Company  conducts  an  actuarial  analysis  on  a  basis  gross  of  reinsurance.  The  same 
estimates  used  as  a  basis  in  calculating  the  gross  IBNR  reserves  are  then  used  as  the  basis  for  calculating  the  net  IBNR 
reserves,  which  take  into  account  the  impact  of  reinsurance.  Anticipated  future  loss  development  patterns  form  a  key 
assumption underlying these analyses. Our claims are generally reported and settled quickly, resulting in consistent historical 
loss development patterns. From the anticipated loss development patterns, a variety of actuarial loss projection techniques 
are employed, such as the chain ladder method, the Bornhuetter-Ferguson method and expected loss ratio method.

The unpaid claims reserves represent the Company’s best estimates, generally involving actuarial projections at a given time. 
Actual  claim  costs  are  dependent  upon  a  number  of  complex  factors  such  as  changes  in  doctrines  of  legal  liabilities  and 
damage  awards.  These  factors  are  not  directly  quantifiable,  particularly  on  a  prospective  basis.  The  Company  periodically 
reviews and updates its methods of making such unpaid claims reserve estimates and establishing the related liabilities based 
on  our  actual  experience.  The  Company  has  not  made  any  changes  to  its  methodologies  for  determining  unpaid  claims 
reserves in the periods presented.

During the year ended December 31, 2023 and 2022, the Company experienced favorable prior year development of $11.2 
million and $0.9 million, respectively, compared to unfavorable prior year development of $1.2 million for the year ended 
December  31,  2021.  In  2023,  the  $11.2  million  favorable  prior  year  development  was  primarily  driven  by  lower  than 
expected claims paid development in our commercial lines of business for the 2018 and 2020 accident years. In 2022, the 
$0.9 million favorable prior year development is primarily due to lower-than-expected claim severity in our commercial lines 
business. In 2021, the $1.2 million increase in prior year development is primarily due to higher-than-expected claim severity 
from business written by a small group of producers of our personal and commercial lines of business. 

Management considers the prior year development for all three years to be insignificant when considered in the context of our 
annual earned premiums, net as well as our net losses and loss adjustment expenses and member benefit claims expenses. For 
the  year  ended  December  31,  2023,  net  losses  and  loss  adjustment  expenses  were  $482.5  million,  which  resulted  to  a  loss 
ratio  of  40.1%.  Without  the  $11.2  million  of  favorable  prior  year  development,  the  2023  loss  ratio  would  have  been 
approximately 0.8% higher. For comparison, the 2022 and 2021 loss ratios were 37.7% and 35.1%, respectively. In general, 
the Company's loss ratio results have been predictable and consistent over time. Actuarial estimates are subject to estimation 
variability,  and  while  management  uses  its  best  judgment  in  establishing  the  estimate  of  required  unpaid  claims,  different 

77

assumptions and variables could lead to significantly different unpaid claims estimates. The variability in these estimates can, 
and have in the past, been significant to pretax income.

We analyze our development on a quarterly basis and given the short duration nature of our products, favorable or adverse 
development  emerges  quickly  and  allows  for  timely  reserve  strengthening,  if  necessary,  or  modifications  to  our  product 
pricing or offerings.

Based upon our internal analysis and our review of the statement of actuarial opinions provided by our actuarial consultants, 
we believe that the amounts recorded for policy liabilities and unpaid claims reasonably represents the amount necessary to 
pay all claims and related expenses which may arise from incidents that have occurred as of the balance sheet date.

While management has used its best judgment in establishing the estimate of required unpaid claims, different assumptions 
and variables could lead to significantly different unpaid claims estimates. The determination of best estimates is affected by 
many factors, including but not limited to:

the quality and applicability of historical data,
current and future economic conditions,
trends in loss frequencies and severities for various causes of loss,
changes in claims reporting patterns,
claims settlement patterns and timing,
regulatory, legislative and judicial decisions,

•
•
•
•
•
•
• morbidity patterns, and
•

the attitudes of claimants towards settlements.

The adequacy of our unpaid claims reserves will be impacted by future trends that impact these factors. Two key measures of 
loss activity are loss frequency, which is the measure of the number of claims per unit of insured exposure, and loss severity, 
which is a measure of the average size of claims. Factors affecting loss frequency include the effectiveness of loss controls, 
changes in economic activity and weather patterns. Factors affecting loss severity include changes in policy limits, retentions, 
rate of inflation and judicial interpretations.

If  the  actual  level  of  loss  frequency  and  severity  are  higher  or  lower  than  expected,  the  ultimate  reserves  required  will  be 
different than management’s estimate. Based on our actuarial analysis, we have determined that an aggregate change that is 
greater than 5% in loss frequency and loss severity is not reasonably likely given the Company’s low limit underwriting and 
low  severity  philosophies.  The  effect  of  higher  and  lower  levels  of  loss  frequency  and  severity  on  our  ultimate  costs  for 
claims occurring in 2023 would be as follows:

Accident Year 2023 Sensitivity Test
Change in Loss & Frequency & Severity on Ultimate 
($ in millions)
Scenario
5% higher
3% higher
1% higher
Base scenario
1% lower
3% lower
5% lower

Ultimate Cost

Change

$ 
$ 
$ 
$ 
$ 
$ 
$ 

518  $ 
508  $ 
498  $ 
493  $ 
488  $ 
478  $ 
468  $ 

25 
15 
5 
— 
(5) 
(15) 
(25) 

Based upon our internal analysis and our review of the statement of actuarial opinions provided by our actuarial consultants, 
we believe that the amounts recorded for policy liabilities and unpaid claims reasonably represents the amount necessary to 
pay all claims and related expenses which may arise from incidents that have occurred as of the balance sheet date.

Deferred Acquisition Costs

The Company defers certain costs of acquiring new and renewal insurance policies, and other products as follows:

Insurance  policy  related  deferred  acquisition  costs  are  limited  to  direct  costs  that  resulted  from  successful  contract 
transactions and would not have been incurred by the Company’s insurance company subsidiaries had the transactions not 
occurred. These capitalized costs are amortized as the related premium is earned.

78

Other deferred acquisition costs are limited to prepaid direct costs, typically commissions and contract transaction fees, that 
resulted  from  successful  contract  transactions  and  would  not  have  been  incurred  by  the  Company  had  the  transactions  not 
occurred. These capitalized costs are amortized as the related service and administrative fees are earned.

The Company evaluates whether all deferred acquisition costs are recoverable at year end, and considers investment income 
in  the  recoverability  analysis  for  insurance  policy  related  deferred  acquisition  costs.  As  a  result  of  the  Company’s 
evaluations, no write-offs for unrecoverable deferred acquisition costs were recognized during the years ended December 31, 
2023 and 2022.

Amortization  of  deferred  acquisition  costs  was  $583.6  million,  $479.1  million  and  $375.1  million  for  the  years  ended 
December 31, 2023, 2022, and 2021, respectively. 

Revenue Recognition

The Company earns revenues from a variety of sources:

Earned Premiums, net

Net earned premiums is from direct and assumed earned premiums consisting of revenue generated from the direct sale of 
insurance policies by the Company’s distributors and premiums written for insurance policies by another carrier and assumed 
by  the  Company.  Whether  direct  or  assumed,  the  premium  is  earned  over  the  life  of  the  respective  policy  using  methods 
appropriate to the pattern of losses for the type of business. Methods used include pro rata, Rule of 78’s, and other actuarial 
methods. Management selects the appropriate method based on available information, and periodically reviews the selections 
as additional information becomes available. Direct and assumed premiums are offset by premiums ceded to the Company’s 
reinsurers, including PORCs, earned in the same manner. The amount ceded is proportional to the amount of risk assumed by 
the reinsurer.

Service and Administrative Fees 

The Company earns service and administrative fees from a variety of activities. Such fees are typically positively correlated 
with transaction volume and are recognized as revenue as they become both realized and earned. Revenues from contracts 
with customers were $341.4 million and $300.2 million for the years ended December 31, 2023 and 2022, respectively, and 
include auto and consumer goods service contracts, motor clubs, other service and administrative fees, vessel related revenue 
and management fee income. See Note (14) Revenue from Contracts with Customers for more detailed disclosure regarding 
these revenues.

Service fee revenue is recognized as the services are performed. Administrative fee revenue includes the administration of 
premium  associated  with  our  producers  and  their  PORCs.  In  addition,  we  also  earn  fee  revenue  from  debt  cancellation 
programs, motor club memberships and warranty programs. Related administrative fee revenue is recognized consistent with 
the earnings recognition pattern of the underlying insurance policies, debt cancellation contracts and motor club memberships 
being  administered,  using  pro  rata,  Rule  of  78’s,  modified  Rule  of  78’s,  or  other  methods  as  appropriate  for  the  contract. 
Management  selects  the  appropriate  method  based  on  available  information,  and  periodically  reviews  the  selections  as 
additional information becomes available. In addition, we also record on an earned basis a ceding fee paid by our reinsurers 
on ceded insurance premiums. This fee reimburses us for administrative, underwriting, and acquisition expenses. These fees 
are earned primarily pro-rata over the remaining term of the policy.

Income Taxes

The  Company  accounts  for  income  taxes  under  the  asset  and  liability  method.  Deferred  tax  assets  and  liabilities  are 
recognized for the future tax consequences attributable to the differences between the financial statement carrying amounts of 
existing assets and liabilities and their respective tax bases. Deferred tax assets and liabilities are measured using enacted tax 
rates  expected  to  apply  to  taxable  income  in  the  years  in  which  the  temporary  differences  are  expected  to  be  recovered  or 
settled.

The  effect  on  deferred  tax  assets  and  liabilities  of  a  change  in  the  tax  rates  is  recognized  in  earnings  in  the  period  that 
includes the enactment date. Additionally, taxing jurisdictions could retroactively disagree with our tax treatment of certain 
items,  and  some  historical  transactions  have  income  tax  effects  going  forward.  Accounting  guidance  requires  these  future 
effects  to  be  evaluated  using  current  laws,  rules  and  regulations,  each  of  which  can  change  at  any  time  and  in  an 

79

 
unpredictable manner.

The  Company  establishes  valuation  allowances  for  deferred  tax  assets  when,  in  its  judgment,  it  concludes  that  it  is  more 
likely than not that the deferred tax assets will not be realized. These judgments are based on projections of future income, 
including  tax-planning  strategies,  by  individual  tax  jurisdictions.  Changes  in  economic  conditions  and  the  competitive 
environment  may  impact  the  accuracy  of  the  Company’s  projections.  On  a  quarterly  basis,  the  Company  assesses  the 
likelihood that its deferred tax assets will be realized and determines if adjustments to the Company’s valuation allowance is 
appropriate.

Recently Issued Accounting Standards

For a discussion of recently issued accounting standards, see Note (2) Summary of Significant Accounting Policies, in the 
accompanying consolidated financial statements.

80

Item 7A. Quantitative and Qualitative Disclosures About Market Risk

Interest Rate Risk

We are exposed to interest rate risk related to borrowings in various businesses. These risks result primarily from changes in 
SOFR rates and the spread over SOFR rates related to the credit risks of our businesses.

For fixed rate debt, interest rate fluctuations generally affect the fair value of our liabilities, but do not impact our earnings. 
Therefore, interest rate risk does not have a significant impact on our fixed rate debt obligations until such obligations mature 
or until we elect to prepay and refinance such obligations. If interest rates have risen at the time our fixed rate debt matures or 
is refinanced, our future earnings could be adversely affected by additional borrowing costs. Conversely, lower interest rates 
at  the  time  of  maturity  or  refinancing  may  lower  our  overall  interest  expense.  As  of  December  31,  2023,  the  Company’s 
insurance subsidiary had $125.0 million of general purpose fixed rate debt outstanding maturing in 2057. 

For general purpose floating rate debt, interest rate fluctuations primarily affect interest expense and cash flows. If market 
interest rates rise, our earnings could be adversely affected by an increase in interest expense. In contrast, lower interest rates 
may reduce our interest expense and improve our earnings, except to the extent that our borrowings are subject to interest rate 
floors. The floating interest rate risk of asset based financing is generally offset as the financing and the purchased financial 
asset are generally subject to the same interest rate risk. As of December 31, 2023, the Company’s insurance subsidiary had 
$165.0 million of floating rate corporate debt with a weighted average rate of 7.3% compared to $35.0 million of floating rate 
corporate  debt  as  of  December  31,  2022,  with  a  weighted  average  rate  of  5.7%.  For  floating  rate  risk  of  other  asset  based 
financing such as borrowings to finance acquisitions of real estate, we generally hedge our exposure to the variability of the 
benchmark index with an interest rate swap. As of December 31, 2023 and 2022, Tiptree’s holding company had no general 
purpose floating rate debt as it was repaid in June 2022. 

Our  consolidated  results  include  investments  in  bonds,  loans  or  other  interest  bearing  instruments.  The  fair  values  of  such 
investments  fluctuate  in  response  to  changes  in  market  interest  rates.  Increases  and  decreases  in  interest  rates  generally 
translate into decreases and increases in fair values of these instruments. Some of these investments bear a floating rate of 
interest  which  subjects  the  Company  to  cash  flow  risk  based  upon  changes  in  the  underlying  interest  rate  index.  As  noted 
above  in  the  discussion  of  risks  related  to  floating  rate  borrowings,  the  Company  mitigates  a  significant  amount  of  our 
floating  rate  risk  by  matching  the  funding  of  such  investments  with  borrowings  based  upon  the  same  interest  rate  index. 
Additionally,  fair  values  of  interest  rate  sensitive  instruments  may  be  affected  by  the  creditworthiness  of  the  issuer, 
prepayment  options,  relative  values  of  alternative  investments,  the  liquidity  of  the  instrument  and  other  general  market 
conditions. 

As of December 31, 2023, we had $879.6 million invested in interest bearing instruments, which represents 66% of the total 
investment portfolio (including cash and cash equivalents). The estimated effects of a hypothetical increase in interest rates of 
100  bps  would  result  in  a  decrease  to  the  fair  value  of  the  portfolio  by  $26.8  million.  As  of  December  31,  2022,  we  had 
$706.4  million  invested  in  interest  bearing  instruments,  which  represented  61%  of  the  total  investment  portfolio.  The 
estimated  effects  of  a  hypothetical  increase  in  interest  rates  of  100  bps  would  result  in  a  decrease  to  the  fair  value  of  the 
portfolio by $24.8 million.

81

Credit Risk

We are exposed to credit risk in the form of available for sale securities, investments in loans, and other investments as 
follows:

($ in thousands)

Available for sale securities, at fair value (1)

Obligations of state and political subdivisions
Corporate securities
Asset backed securities 
Certificates of deposit
Obligations of foreign governments

Loans, at fair value(2)
Corporate loans
Other investments(3)

Corporate bonds, at fair value
Debentures
Investment in credit fund
Other

Total

As of December 31,
2022
2023

$ 

$ 

45,459  $ 
254,598 
26,186 
1,724 
4,557 

49,454 
161,999 
15,349 
756 
2,362 

11,218 

14,312 

62,081 
25,648 
11,830 
7,201 
450,502  $ 

42,080 
23,853 
— 
230 
310,395 

(1) 

(2) 

(3) 

The Company also holds investments in U.S. Treasury securities and obligations of U.S. government authorities and agencies of $470.1 million and 
$382.1 million as of December 31, 2023 and 2022, respectively. These investments do not represent a credit risk and are excluded.
The  Company  also  holds  investments  in  mortgage  loans  held  for  sale  of  $58.3  million  and  $50.5  million  as  of  December  31,  2023  and  2022, 
respectively. These investments do not represent a credit risk and are excluded.
The Company also holds other investments of $4.3 million and $6.9 million as of December 31, 2023 and 2022, respectively, primarily comprised of 
vessels and other investments. These investments do not represent a credit risk and are excluded.

Credit  risk  within  the  Company’s  investments  represents  the  exposure  to  the  adverse  changes  in  the  creditworthiness  of 
individual investment holdings, issuers, groups of issuers, industries, and countries. As of December 31, 2023 and 2022, 72% 
and 76%, respectively, of the investments subject to credit risk had investment grade ratings. A widening of credit spreads by 
100 bps for the investments subject to credit risk would result in a decrease of $8.2 million and $5.8 million to the fair value 
of the portfolio as of December 31, 2023 and 2022, respectively. 

In  addition,  our  mortgage  business  also  underwrites  mortgage  loans  for  the  purpose  of  selling  them  into  the  secondary 
market. Due to the relatively short holding period, the credit risk associated with mortgage loans held for sale is not expected 
to be significant. 

See Note (6) Investments to the consolidated financial statements for more information regarding our investments in loans by 
type.

Market Risk

We are primarily exposed to market risk related to the following investments: 

($ in thousands)

As of December 31, 2023

As of December 31, 2022

Insurance

Tiptree Capital 
- Other

Total

Insurance

Tiptree Capital 
- Other

Total

Invesque
$ 
Fixed income exchange traded fund  
Other equity securities

Total equity securities

$ 

719  $ 

1,349 
25,045 
27,113  $ 

3,442  $ 
— 
37,753 
41,195  $ 

4,161  $ 
1,349 
62,798 
68,308  $ 

2,670  $ 
56,256 
14,066 
72,992  $ 

12,784  $ 
— 
— 
12,784  $ 

15,454 
56,256 
14,066 
85,776 

A 10% increase or decrease in the fair value of such investments would result in $6.8 million and $8.6 million of unrealized 
gains and losses as of December 31, 2023 and 2022, respectively. 

As  of  December  31,  2023  and  2022,  the  Company  owned  16.98  million  shares  of  common  stock,  respectively,  or 
approximately 30%, of Invesque, a real estate investment company that specializes in health care real estate and senior living 
property  investment  throughout  North  America.  The  value  of  our  Invesque  shares  is  reported  at  fair  market  value  on  a 
quarterly basis. Invesque historically paid monthly dividends until April 2020, when dividends were discontinued. A loss in 

82

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
the fair market value of our Invesque shares or a reduction or discontinuation in the dividends paid on our Invesque shares 
could have a material adverse effect on our financial condition and results of operations. As of December 31, 2023 and 2022, 
the fair value of the Invesque shares was based on the market price.

See “Risk Factors — Risks Related to our Business - Our investment in Invesque shares is subject to market volatility and the 
risk that Invesque changes its dividend policy”.

Foreign Currency Exchange Rate Risk

We have foreign currency exchange rate risk associated with certain assets and liabilities related to our foreign operations. At 
December 31, 2023 and 2022, 93% and 93%, respectively of our invested assets were denominated in United States (U.S.) 
Dollars.  At  December  31,  2023  and  2022,  92%  and  93%,  respectively,  of  our  insurance  subsidiary’s  combined  unpaid 
premiums  and  deferred  revenue  were  denominated  in  U.S.  Dollars.  At  that  date,  the  largest  foreign  currency  denominated 
balance was a fixed income exchange traded fund in British Pound Sterling reported within equity securities.

Counterparty Risk

We are subject to counterparty risk to the extent that we engage in derivative activities for hedging or other purposes. As of 
December 31, 2023 and 2022, the total fair value of derivative assets subject to counterparty risk, including the effect of any 
legal  right  of  offset,  totaled  $4.0  million  and  $4.3  million,  respectively.  We  generally  manage  our  counterparty  risk  to 
derivative counterparties by entering into contracts with counterparties of high credit quality.

Total reinsurance receivables and prepaid reinsurance premiums were $1,854.4 million and 1,176.1 million of December 31, 
2023  and  2022,  respectively.  Of  those  amounts,  $870.5  million  and  $603.4  million,  respectively,  related  to  contracts  with 
third-party  captives  in  which  we  hold  collateral  or  receive  letters  of  credit  in  excess  of  the  reinsurance  receivables.  The 
remainder  is  held  with  high  quality  reinsurers,  substantially  all  of  which  have  a  rating  of  A  or  better  by  A.M.  Best.  As  of 
December  31,  2023,  the  non-affiliated  reinsurers  from  whom  our  insurance  business  has  the  largest  reinsurance  receivable 
balances  represented  $235.7  million,  or  12.7%  of  the  total,  and  included:  Accelerant  Specialty  Insurance  Company  (A.M. 
Best  Rating:  A-  rated),  Allianz  Global  Corporate  &  Specialty  SE  (A.M.  Best  Rating:  A+  rated),  and  Homesite  Insurance 
Company (A.M. Best Rating: A rated). A majority of the related receivables from these reinsurers are collateralized by assets 
on  hand  and  letters  of  credit;  receivable  balances  from  authorized  reinsurers  do  not  require  collateral.  Allianz  Global 
Corporate  &  Specialty  SE  is  an  authorized  reinsurer  in  the  states  in  which  Fortegra’s  U.S.  based  insurance  entities  are 
domiciled.  The  Company  monitors  authorization  status  and  A.M.  Best  ratings  of  its  reinsurers  periodically.  As  of 
December  31,  2023,  the  Company  does  not  believe  there  is  a  risk  of  loss  due  to  the  concentration  of  credit  risk  in  the 
reinsurance program given the collateralization.

($ in thousands)

Third-party captives

Reinsurance receivables and prepaid reinsurance premiums
Collateral
% Collateralized

Professional Reinsurers

Reinsurance receivables and prepaid reinsurance premiums
Collateral
% Collateralized

Total

Reinsurance receivables and prepaid reinsurance premiums
Collateral
% Collateralized

As of December 31,
2022
2023

$ 
870,511 
$  1,035,728 

 119 %

$ 
$ 

983,900 
643,853 

$ 
$ 

$ 
$ 

603,428 
700,086 

 116 %

572,662 
611,360 

 65 %

 107 %

$  1,854,410 
$  1,679,581 

$  1,176,090 
$  1,311,446 

 91 %

 112 %

We were also exposed to counterparty risk of approximately $250.8 million and $191.1 million as of December 31, 2023 and 
2022,  respectively,  related  to  our  retrospective  commission  arrangements;  associated  risks  are  offset  by  the  Company’s 
contractual  ability  to  withhold  future  commissions  against  the  retrospective  balances.  In  addition,  we  are  exposed  to 
counterparty  risk  of  approximately  $134.1  million  and  $121.4  million  as  of  December  31,  2023  and  2022,  respectively, 
related to our premium financing business. The risk associated with such arrangements is mitigated by the fact that we have 
the  contractual  ability  to  cancel  the  insurance  policy  and  have  premiums  refunded  to  us  by  the  insurer  in  the  event  of  a 
counterparty default.

83

Item 8. Financial Statements and Supplementary Data

Index to Consolidated Financial Statements

Report of Independent Registered Public Accounting Firm (PCAOB ID No. 34)
Consolidated Balance Sheets as of December 31, 2023 and 2022
Consolidated Statements of Operations for the years ended December 31, 2023, 2022 and 2021
Consolidated Statements of Comprehensive Income (Loss) for the years ended December 31, 2023, 2022 and 2021
Consolidated Statements of Changes in Stockholders’ Equity for the years ended December 31, 2023, 2022 and 2021
Consolidated Statements of Cash Flows for the years ended December 31, 2023, 2022 and 2021
Notes to Consolidated Financial Statements

Page
F- 2
F- 5
F- 6
F- 7
F- 8
F- 10
F- 12

F-1

REPORT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM

To the stockholders and the Board of Directors of Tiptree Inc. 

Opinion on the Financial Statements 

We have audited the accompanying consolidated balance sheets of Tiptree Inc. and subsidiaries (the “Company”) as of 
December 31, 2023 and 2022, the related consolidated statements of operations, comprehensive income (loss), changes 
in  stockholders’  equity,  and  cash  flows,  for  each  of  the  three  years  in  the  period  ended  December  31,  2023,  and  the 
related notes and the schedule listed in the Index at Item 15 (collectively referred to as the “financial statements”). In our 
opinion,  the  financial  statements  present  fairly,  in  all  material  respects,  the  financial  position  of  the  Company  as  of 
December 31, 2023 and 2022, and the results of its operations and its cash flows for each of the three years in the period 
ended December 31, 2023, in conformity with accounting principles generally accepted in the United States of America.

We  have  also  audited,  in  accordance  with  the  standards  of  the  Public  Company  Accounting  Oversight  Board  (United 
States)  (PCAOB),  the  Company’s  internal  control  over  financial  reporting  as  of  December  31,  2023,  based  on  criteria 
established in Internal Control — Integrated Framework (2013) issued by the Committee of Sponsoring Organizations 
of  the  Treadway  Commission  and  our  report  dated  February  29,  2024,  expressed  an  unqualified  opinion  on  the 
Company’s internal control over financial reporting.

Basis for Opinion 

These  financial  statements  are  the  responsibility  of  the  Company’s  management.  Our  responsibility  is  to  express  an 
opinion on the Company’s financial statements based on our audits. We are a public accounting firm registered with the 
PCAOB and are required to be independent with respect to the Company in accordance with the U.S. federal securities 
laws and the applicable rules and regulations of the Securities and Exchange Commission and the PCAOB.

We  conducted  our  audits  in  accordance  with  the  standards  of  the  PCAOB.  Those  standards  require  that  we  plan  and 
perform  the  audit  to  obtain  reasonable  assurance  about  whether  the  financial  statements  are  free  of  material 
misstatement, whether due to error or fraud. Our audits included performing procedures to assess the risks of material 
misstatement of the financial statements, whether due to error or fraud, and performing procedures that respond to those 
risks.  Such  procedures  included  examining,  on  a  test  basis,  evidence  regarding  the  amounts  and  disclosures  in  the 
financial statements. Our audits also included evaluating the accounting principles used and significant estimates made 
by  management,  as  well  as  evaluating  the  overall  presentation  of  the  financial  statements.  We  believe  that  our  audits 
provide a reasonable basis for our opinion.

Critical Audit Matter

The critical audit matter communicated below is a matter arising from the current-period audit of the financial statements 
that  was  communicated  or  required  to  be  communicated  to  the  audit  committee  and  that  (1)  relates  to  accounts  or 
disclosures  that  are  material  to  the  financial  statements  and  (2)  involved  our  especially  challenging,  subjective,  or 
complex judgments. The communication of critical audit matters does not alter in any way our opinion on the financial 
statements,  taken  as  a  whole,  and  we  are  not,  by  communicating  the  critical  audit  matter  below,  providing  a  separate 
opinion on the critical audit matter or on the accounts or disclosures to which it relates.

Policy liabilities and unpaid claims – Refer to Notes 2 and 13 to the financial statements

Critical Audit Matter Description

Policy  liabilities  and  unpaid  claims  include  claims  in  the  normal  course  of  settlement  and  reserve  estimates.  The 
Company estimates policy liabilities and unpaid claims by applying a variety of generally accepted actuarial methods to 
historical loss development patterns, which require numerous assumptions and significant judgment. 

We  identified  policy  liabilities  and  unpaid  claims  as  a  critical  audit  matter  because  of  the  significant  estimates  and 
assumptions management made in forecasting ultimate losses. This critical audit matter required a high degree of auditor 
judgment and an increased extent of audit effort, including the need to involve our actuarial specialists, when performing 
audit procedures to evaluate management’s selection of various assumptions in determining unpaid claims reserves. 

How the Critical Audit Matter Was Addressed in the Audit

F-2

Our audit procedures related to testing management’s significant estimates and assumptions used in determining policy 
liabilities and unpaid claims included the following, among others:

• We tested the design and operating effectiveness of controls over policy liabilities and unpaid claims, including 
those related to the estimation and management’s review of the estimates as well as the selection of underlying 
assumptions. 

• We tested the design and operating effectiveness of controls over the completeness and accuracy of the 

premium and claim data utilized by management and their third-party actuaries.

• We evaluated the methods and assumptions used by the Company to estimate the policy liabilities and unpaid 

claims through the following procedures:

◦ With assistance from our actuarial specialists:

▪ We developed an independent expected range of policy liabilities and unpaid claims reserves 
based on historical and industry claim development factors or performed actuarial peer review 
procedures to evaluate management’s application of actuarial methods and significant 
assumptions.

▪ We performed retrospective procedures comparing actual loss development with expected 
development to assess the reasonableness of assumptions used, including consideration of 
potential bias, in the estimation of policy liabilities and unpaid claims.

◦ We tested the underlying data that served as the basis for the actuarial analysis, including historical 

claims data, to test that the inputs to the actuarial estimates were complete and accurate.   

/s/Deloitte & Touche LLP
New York, New York
February 29, 2024

We have served as the Company's auditor since 2017.    

F-3

REPORT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM

To the stockholders and the Board of Directors of Tiptree Inc. 

Opinion on Internal Control over Financial Reporting 

We  have  audited  the  internal  control  over  financial  reporting  of  Tiptree  Inc.  and  subsidiaries  (the  “Company”)  as  of 
December  31,  2023,  based  on  criteria  established  in  Internal  Control  —  Integrated  Framework  (2013)  issued  by  the 
Committee  of  Sponsoring  Organizations  of  the  Treadway  Commission  (COSO).  In  our  opinion,  the  Company 
maintained, in all material respects, effective internal control over financial reporting as of December 31, 2023, based on 
criteria established in Internal Control — Integrated Framework (2013) issued by COSO.

We  have  also  audited,  in  accordance  with  the  standards  of  the  Public  Company  Accounting  Oversight  Board  (United 
States) (PCAOB), the consolidated financial statements as of and for the year ended December 31, 2023, of the Company 
and our report dated February 29, 2024 expressed an unqualified opinion on those financial statements.

Basis for Opinion 

The Company’s management is responsible for maintaining effective internal control over financial reporting and for its 
assessment of the effectiveness of internal control over financial reporting, included in the accompanying Management’s 
Report  on  Internal  Control  over  Financial  Reporting.  Our  responsibility  is  to  express  an  opinion  on  the  Company’s 
internal control over financial reporting based on our audit. We are a public accounting firm registered with the PCAOB 
and are required to be independent with respect to the Company in accordance with the U.S. federal securities laws and 
the applicable rules and regulations of the Securities and Exchange Commission and the PCAOB.

We  conducted  our  audit  in  accordance  with  the  standards  of  the  PCAOB.  Those  standards  require  that  we  plan  and 
perform  the  audit  to  obtain  reasonable  assurance  about  whether  effective  internal  control  over  financial  reporting  was 
maintained  in  all  material  respects.  Our  audit  included  obtaining  an  understanding  of  internal  control  over  financial 
reporting, assessing the risk that a material weakness exists, testing and evaluating the design and operating effectiveness 
of internal control based on the assessed risk, and performing such other procedures as we considered necessary in the 
circumstances. We believe that our audit provides a reasonable basis for our opinion.

Definition and Limitations of Internal Control over Financial Reporting 

A company’s internal control over financial reporting is a process designed to provide reasonable assurance regarding 
the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with 
generally accepted accounting principles. A company’s internal control over financial reporting includes those policies 
and procedures that (1) pertain to the maintenance of records that, in reasonable detail, accurately and fairly reflect the 
transactions  and  dispositions  of  the  assets  of  the  company;  (2)  provide  reasonable  assurance  that  transactions  are 
recorded  as  necessary  to  permit  preparation  of  financial  statements  in  accordance  with  generally  accepted  accounting 
principles, and that receipts and expenditures of the company are being made only in accordance with authorizations of 
management  and  directors  of  the  company;  and  (3)  provide  reasonable  assurance  regarding  prevention  or  timely 
detection of unauthorized acquisition, use, or disposition of the company’s assets that could have a material effect on the 
financial statements.

Because  of  its  inherent  limitations,  internal  control  over  financial  reporting  may  not  prevent  or  detect  misstatements. 
Also,  projections  of  any  evaluation  of  effectiveness  to  future  periods  are  subject  to  the  risk  that  controls  may  become 
inadequate  because  of  changes  in  conditions,  or  that  the  degree  of  compliance  with  the  policies  or  procedures  may 
deteriorate.

/s/Deloitte & Touche LLP
New York, New York
February 29, 2024

F-4

TIPTREE INC. AND SUBSIDIARIES
Consolidated Balance Sheets
(in thousands, except share data)

As of December 31,

2023

2022

Assets:
Investments:

Available for sale securities, at fair value, net of allowance for credit losses
Loans, at fair value
Equity securities
Other investments

Total investments
Cash and cash equivalents 
Restricted cash
Notes and accounts receivable, net
Reinsurance recoverable
Prepaid reinsurance premiums
Deferred acquisition costs
Goodwill
Intangible assets, net
Other assets

Total assets

Liabilities and Stockholders’ Equity
Liabilities:
Debt, net
Unearned premiums
Policy liabilities and unpaid claims
Deferred revenue
Reinsurance payable
Other liabilities and accrued expenses

Total liabilities

Stockholders’ Equity:

Preferred stock: $0.001 par value, 100,000,000 shares authorized, none issued or outstanding
Common stock: $0.001 par value, 200,000,000 shares authorized, 36,756,187 and 36,385,299 
shares issued and outstanding, respectively
Additional paid-in capital
Accumulated other comprehensive income (loss), net of tax
Retained earnings
Total Tiptree Inc. stockholders’ equity

Non-controlling interests:

Fortegra preferred interests
Common interests
Total non-controlling interests
Total stockholders’ equity

Total liabilities and stockholders’ equity

$ 

$ 

802,609  $ 
69,556 
68,308 
111,088 
1,051,561 
468,711 
23,850 
684,608 
953,886 
900,524 
565,746 
206,155 
118,757 
165,515 
5,139,313  $ 

$ 

402,411  $ 

1,695,058 
844,848 
673,085 
543,602 
403,744 
4,562,748  $ 

611,980 
64,843 
85,776 
73,025 
835,624 
538,065 
12,782 
502,311 
450,620 
725,470 
498,925 
186,608 
117,015 
172,143 
4,039,563 

259,366 
1,357,436 
567,193 
649,150 
305,097 
367,748 
3,505,990 

$ 

$ 

$ 

—  $ 

— 

37 
382,239 
(26,073) 
60,663 
416,866 

36 
382,645 
(39,429) 
54,113 
397,365 

77,679 
82,020 
159,699 
576,565 
5,139,313  $ 

77,679 
58,529 
136,208 
533,573 
4,039,563 

See accompanying notes to consolidated financial statements. 

F-5

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Consolidated Statements of Operations
(in thousands, except share data)

For the Year Ended December 31,
2022

2021

2023

Revenues:

Earned premiums, net
Service and administrative fees
Ceding commissions
Net investment income
Net realized and unrealized gains (losses)
Other revenue
Total revenues

Expenses:

Policy and contract benefits
Commission expense
Employee compensation and benefits
Interest expense
Depreciation and amortization
Other expenses
Total expenses

Income (loss) before taxes

Less: provision (benefit) for income taxes

Net income (loss)

Less: net income (loss) attributable to non-controlling interests
Net income (loss) attributable to common stockholders

Net income (loss) per common share:

Basic earnings per share
Diluted earnings per share

Weighted average number of common shares:

Basic
Diluted

$ 

$ 

$ 
$ 

1,127,834  $ 
395,969 
14,915 
26,674 
24,736 
58,903 
1,649,031 

601,794 
603,033 
179,075 
27,692 
23,466 
130,918 
1,565,978 
83,053 
43,056 
39,997 
26,046 
13,951  $ 

904,765  $ 
320,720 
13,880 
12,219 
69,983 
76,185 
1,397,752 

452,605 
522,686 
182,657 
30,240 
22,973 
132,580 
1,343,741 
54,011 
50,450 
3,561 
11,835 
(8,274)  $ 

685,552 
260,525 
11,784 
17,896 
151,350 
73,407 
1,200,514 

327,012 
396,683 
207,322 
37,674 
24,437 
142,044 
1,135,172 
65,342 
21,291 
44,051 
5,919 
38,132 

0.38  $ 
0.33  $ 

(0.23)  $ 
(0.23)  $ 

1.13 
1.09 

36,693,204 
37,619,095 

35,531,149 
35,531,149 

33,223,792 
33,688,256 

Dividends declared per common share

$ 

0.20  $ 

0.16  $ 

0.16 

See accompanying notes to consolidated financial statements. 

F-6

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Consolidated Statements of Comprehensive Income (Loss) 
(in thousands)

For the Year Ended December 31,
2022

2021

2023

Net income (loss)

$ 

39,997  $ 

3,561  $ 

44,051 

Other comprehensive income (loss), net of tax:

Change in unrealized gains (losses) on available for sale securities
Change in unrealized currency translation adjustments
Related (provision) benefit for income taxes

Other comprehensive income (loss), net of tax

Comprehensive income (loss)

Less: comprehensive income (loss) attributable to non-controlling interests
Comprehensive income (loss) attributable to common stockholders

$ 

19,003 
7,213 
(8,105) 
18,111 
58,108 
30,801 
27,307  $ 

(55,290) 
(7,351) 
14,973 
(47,668) 
(44,107) 
8,104 
(52,211)  $ 

(10,750) 
— 
2,362 
(8,388) 
35,663 
5,890 
29,773 

See accompanying notes to consolidated financial statements.

F-7

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Consolidated Statements of Changes in Stockholders’ Equity
(in thousands, except shares)

Common stock

Non-controlling interests

Additional 
paid-in 
capital

Number of 
shares

2,331 
3,563 
105 
(2,881) 
— 
(770) 
— 
— 
97 
— 
— 
— 

— 
596,601 
1,166,307 
(528,662) 
207,445 
— 
— 
— 
— 
— 
— 
— 

Par 
value 
  32,682,462  $  33  $  315,014  $ 
  — 
  — 
2 
(1) 
  — 
  — 
  — 
  — 
  — 
  — 
  — 
  — 
  34,124,153  $  34  $  317,459  $ 
  — 
  — 
  — 
  — 
2 
  — 
  — 
  — 
  — 
  — 
  — 
  — 
  — 
  — 
  — 
  36,385,299  $  36  $  382,645  $ 

— 
292,548 
114,353 
(165,040) 
1,999,989 
19,296 
— 
— 
— 
— 
— 
— 
— 
— 
— 

6,600 
(172) 
866 
(1,727) 
13,722 
— 
4,847 
41,092 
— 
— 
(42) 
— 
— 
— 
— 

Accumulated 
other 
comprehensive 
income (loss)

Retained 
earnings

Total
Tiptree Inc. 
stockholders’ 
equity

Fortegra 
preferred 
interests

Common 
interests

Total 
stockholders' 
equity

5,674  $ 
— 
— 
— 
— 
— 
— 
— 
— 
— 
— 
(8,359) 
— 
(2,685)  $ 
— 
— 
— 
— 
— 
— 
— 
7,193 
— 
— 
— 
— 
(43,937) 
— 
— 
(39,429)  $ 

35,423  $  356,144  $ 

— 
— 
— 
— 
— 
— 
— 
— 
— 
(5,409) 
— 
38,132 
68,146  $  382,954  $ 

2,331 
3,563 
107 
(2,882) 
— 
(770) 
— 
— 
97 
(5,409) 
(8,359) 
38,132 

— 
— 
— 
— 
— 
— 
— 
— 
— 
— 
— 
(5,759) 
— 
(3,384) 
(4,890) 
54,113  $  397,365  $ 

6,600 
(172) 
866 
(1,727) 
13,724 
— 
4,847 
48,285 
— 
— 
(42) 
(5,759) 
(43,937) 
(3,384) 
(4,890) 

—  $ 
— 
— 
— 
— 
— 
— 
— 
— 
— 
— 
— 
— 
—  $ 
— 
— 
— 
— 
— 
— 
— 
77,679 
— 
— 
— 
— 
— 
— 
— 
77,679  $ 

17,394  $  373,538 
4,056 
1,725 
(1,253) 
(4,816) 
(1,458) 
(1,565) 
(2,882) 
— 
— 
— 
(1,079) 
(309) 
100 
100 
(1,095) 
(1,095) 
— 
(97) 
(5,409) 
— 
(8,388) 
(29) 
5,919 
44,051 
17,227  $  400,181 
7,469 
869 
(1,258) 
(1,086) 
(181) 
(1,047) 
(1,727) 
— 
13,724 
— 
— 
— 
4,847 
— 
167,008 
41,044 
250 
250 
(3,939) 
(3,939) 
449 
491 
(5,759) 
— 
(47,668) 
(3,731) 
(3,384) 
— 
8,451 
3,561 
58,529  $  533,573 

Balance at December 31, 2020
Amortization of share-based incentive compensation
Vesting of share-based incentive compensation
Shares issued in exchange for vested subsidiary awards (1)
Shares purchased under stock purchase plan
Shares issued upon exercise of warrants
Repurchase of vested subsidiary awards
Non-controlling interest contributions
Non-controlling interest distributions
Net change in non-controlling interests and other
Common stock dividends declared
Other comprehensive income (loss), net of tax
Net income (loss)
Balance at December 31, 2021
Amortization of share-based incentive compensation
Vesting of share-based incentive compensation
Shares issued in exchange for vested subsidiary awards (2)
Shares purchased under stock purchase plan
Shares issued upon exercise of warrants
Shares issued upon exercise of options
Transfer of liability awards
WP Transaction
Non-controlling interest contributions
Non-controlling interest distributions
Net change in non-controlling interests and other
Common stock dividends declared
Other comprehensive income (loss), net of tax
Subsidiary preferred dividends declared
Net income (loss)
Balance at December 31, 2022

F-8

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Consolidated Statements of Changes in Stockholders’ Equity
(in thousands, except shares)

Common stock

Non-controlling interests

Additional 
paid-in 
capital

Number of 
shares

Par 
value 
  36,385,299  $  36  $  382,645  $ 
  — 
1 
  — 
  — 
  — 
  — 
  — 
  — 
  — 
  36,756,187  $  37  $  382,239  $ 

— 
315,881 
55,007 
— 
— 
— 
— 
— 
— 

5,845 
(250) 
— 
(1,751) 
(4,250) 
— 
— 
— 
— 

Accumulated 
other 
comprehensive 
income (loss)

Retained 
earnings

Total
Tiptree Inc. 
stockholders’ 
equity

Fortegra 
preferred 
interests

Common 
interests

Total 
stockholders' 
equity

(39,429)  $ 
— 
— 
— 
— 
— 
— 
13,356 
— 
— 
(26,073)  $ 

54,113  $  397,365  $ 

— 
— 
— 
— 
— 
(7,401) 
— 
(6,400) 
20,351 
60,663  $  416,866  $ 

5,845 
(249) 
— 
(1,751) 
(4,250) 
(7,401) 
13,356 
(6,400) 
20,351 

77,679  $ 
— 
— 
— 
— 
— 
— 
— 
— 
— 
77,679  $ 

58,529  $  533,573 
7,708 
1,863 
(719) 
(470) 
— 
— 
(4,959) 
(3,208) 
(3,345) 
905 
(7,401) 
— 
18,111 
4,755 
(6,400) 
— 
19,646 
39,997 
82,020  $  576,565 

Balance at December 31, 2022
Amortization of share-based incentive compensation
Vesting of share-based incentive compensation
Shares issued upon exercise of options
Non-controlling interest distributions
Net change in non-controlling interests and other
Common stock dividends declared
Other comprehensive income (loss), net of tax
Subsidiary preferred dividends declared
Net income (loss)
Balance at December 31, 2023

(1)    Exchange included $1,458 in cash.
(2)    Exchange included $181 in cash.

See accompanying notes to consolidated financial statements.

F-9

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Consolidated Statements of Cash Flows
(in thousands)

For the Year Ended December 31,
2022

2021

2023

Operating Activities:

Net income (loss) attributable to common stockholders
Net income (loss) attributable to non-controlling interests

Net income (loss)

Adjustments to reconcile net income to net cash provided by (used in) operating activities
Net realized and unrealized (gains) losses 
Net (gain) loss on held for sale of business
Non-cash compensation expense
Amortization/accretion of premiums and discounts
Depreciation and amortization expense
Non-cash lease expense
Deferred provision (benefit) for income taxes
Amortization of deferred financing costs
Change in fair value of liability classified warrants
Other

$ 

13,951  $ 
26,046 
39,997 

(8,274)  $ 
11,835 
3,561 

38,132 
5,919 
44,051 

(24,736)   

— 
8,275 
(7,556)   
23,466 
7,951 
37,024 
1,125 
(1,769)   
148 

(69,983)   
(3,825)   
9,705 
976 
22,973 
9,301 
47,548 
1,341 
(939)   
1,137 

(151,350) 
1,928 
11,130 
2,947 
24,437 
8,924 
17,730 
1,607 
— 
291 

Changes in operating assets and liabilities:

Mortgage loans originated for sale
Proceeds from the sale of mortgage loans originated for sale
(Increase) decrease in notes and accounts receivable
(Increase) decrease in reinsurance recoverable
(Increase) decrease in prepaid reinsurance premiums
(Increase) decrease in deferred acquisition costs
(Increase) decrease in other assets
Increase (decrease) in unearned premiums
Increase (decrease) in policy liabilities and unpaid claims
Increase (decrease) in deferred revenue
Increase (decrease) in reinsurance payable
Increase (decrease) in other liabilities and accrued expenses
Net cash provided by (used in) operating activities

Investing Activities:

Purchases of investments
Proceeds from sales and maturities of investments
Purchases of property, plant and equipment
Proceeds from the sale of businesses and other assets
Proceeds from notes receivable
Issuance of notes receivable
Business and asset acquisitions, net of cash and deposits
Net cash provided by (used in) investing activities

Financing Activities:

Dividends paid
Cash received for the exercise of warrants
Net non-controlling interest (redemptions) contributions and other
Issuance of Fortegra Common Stock
Issuance of Fortegra Warrants
Issuance of Fortegra Additional Warrants (Warburg)
Issuance of Fortegra Preferred Stock
Payment of WP Transaction costs
Payment of debt issuance costs
Proceeds from borrowings and mortgage notes payable
Principal paydowns of borrowings and mortgage notes payable
Repurchases of common stock and other changes in additional paid-in capital
Net cash provided by (used in) financing activities
Effect of exchange rate changes on cash

Net increase (decrease) in cash, cash equivalents and restricted cash

Cash, cash equivalents and restricted cash – beginning of period
Cash, cash equivalents and restricted cash – beginning of period - held for sale
Cash, cash equivalents and restricted cash – end of period
Less: Reclassification of cash to held for sale

Cash, cash equivalents and restricted cash – end of period

F-10

 2,403,223 

(876,914)   (2,136,005)   (3,884,533) 
  3,925,984 
903,354 
(54,378) 
(160,501)   
(13,227)   
(78,932) 
(505,700)    (203,874)   
(73,895) 
(175,054)   
(91,380)   
(149,943) 
(65,404)    (119,552)   
(7,065) 
20,921 
263,262 
337,622 
98,265 
277,655 
135,652 
14,613 
40,909 
238,505 
27,295 
(21,570)   
204,316 
71,452 

7,463 
  233,484 
  235,490 
  113,899 
39,528 
(27,771)   

  463,073 

(14,030)   

 (1,492,227)   (1,197,383)   (1,430,879) 
  1,172,044 
 1,260,594 
  1,296,337 
(2,764) 
8,729 
56,055 
(77,077) 
133 
(273,759) 

— 
117,834 
(132,857)    (114,187)   
(14,960)   
(19,726)   
9,514 
(244,669)   

(10,727)   
742 
85,435 

— 

(13,731)   

(14,783)   

— 
— 
— 
— 
— 
(1,487)   

(7,775)   
13,724 
(5,590)   
98,433 
13,101 
6,230 
83,486 
(12,910)   
(1,380)   

(5,409) 
— 
(3,532) 
— 
— 
— 
— 
— 
(114) 
  1,431,526 
  4,084,299 
 2,365,320 
 (1,288,119)   (2,666,098)   (3,993,364) 
(8,145) 
73,735 
— 
4,292 
195,275 
4,879 
204,446 
9,360 
$  492,561  $  550,847  $  195,086 

(58,286)    355,573 
  195,086 
550,847 
9,360 
— 
  560,019 
492,561 
9,172 
— 

(1,727)   
  (115,186)   
(1,828)   

— 
113,406 
1,525 

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Consolidated Statements of Cash Flows
(in thousands)

Supplemental Disclosure of Cash Flow Information:
Cash paid during the period for interest expense
Cash (received) paid during the period for income taxes
Supplemental Schedule of Non-Cash Investing and Financing Activities:

Right of use asset obtained in exchange for lease liability
Bonds and trade receivables exchanged for corporate loans and equity securities
Shares issued in exchange for vested subsidiary awards

Reconciliation of cash, cash equivalents and restricted cash

Cash and cash equivalents 
Restricted cash

Total cash, cash equivalents and restricted cash shown in the statements of cash flows

For the Year Ended December 31,
2022

2021

2023

$ 
$ 

26,513  $  29,442  $ 
2,259  $ 
(15,178)  $ 

36,885 
2,079 

$ 
$ 
$ 

4,281 
— 
107 

3,338  $  14,698  $ 
—  $  19,846  $ 
—  $ 
866  $ 
As of December 31,
2022
$  468,711  $  538,065  $  175,718 
19,368 
$  492,561  $  550,847  $  195,086 

23,850 

12,782 

2023

2021

See accompanying notes to consolidated financial statements.

F-11

 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

(1) Organization 

Tiptree Inc. (together with its consolidated subsidiaries, collectively, Tiptree, the Company, or we) is a Maryland Corporation 
that was incorporated on March 19, 2007. Tiptree’s common stock trades on the Nasdaq Capital Market under the symbol 
“TIPT”.  Tiptree  is  a  holding  company  that  allocates  capital  across  a  broad  spectrum  of  businesses,  assets  and  other 
investments. We classify our business into two reportable segments: Insurance and Mortgage. We refer to our non-insurance 
operations,  assets  and  other  investments,  which  is  comprised  of  our  Mortgage  reportable  segment  and  our  non-reportable 
segments and other business activities, as Tiptree Capital.

On June 21, 2022, the Company closed the WP Transaction whereby Warburg invested $200,000 in Fortegra in exchange for 
Fortegra  Common  Stock,  Fortegra  Preferred  Stock,  Fortegra  Warrants  and  Fortegra  Additional  Warrants.  See  Note  (17) 
Stockholders' Equity for additional information regarding the terms of the securities issued in connection with the closing of 
the WP Transaction. As of December 31, 2023, Fortegra was owned approximately 79.5% by Tiptree Holdings, 17.5% by 
Warburg and 3.0% by management and directors of Fortegra, before giving effect to the exercise of outstanding warrants and 
the conversion of outstanding preferred stock.

(2) Summary of Significant Accounting Policies

Basis of Presentation and Principles of Consolidation

The accompanying consolidated financial statements of Tiptree have been prepared in accordance with GAAP and include 
the  accounts  of  the  Company  and  its  subsidiaries.  The  consolidated  financial  statements  are  presented  in  U.S.  dollars,  the 
main operating currency of the Company. 

Non-controlling  interests  on  the  consolidated  financial  statements  represent  the  ownership  interests  in  certain  consolidated 
subsidiaries held by entities or persons other than Tiptree. Accounts and transactions between consolidated entities have been
eliminated.

Reclassifications

As  a  result  of  changes  in  presentation,  certain  prior  year  amounts  have  been  reclassified  to  conform  to  the  current 
presentation. These reclassifications had no effect on the reported results of operations.

Use of Estimates

The preparation of the Company’s consolidated financial statements in conformity with GAAP requires management to make 
estimates  and  assumptions  that  affect  the  amounts  reported  in  the  Company’s  consolidated  financial  statements  and 
accompanying notes. Management makes estimates and assumptions that include, but are not limited to, the determination of 
the following significant items:

•
•
•
•

•

•
•
•

Fair value of financial assets and liabilities, including, but not limited to, securities, loans and derivatives
Value of acquired assets and liabilities;
Carrying value of goodwill and other intangibles, including estimated amortization period and useful lives;
Reserves for unpaid losses and loss adjustment expenses, estimated future claims and losses, potential litigation and 
other claims;
Revenue  recognition  including,  but  not  limited  to,  the  timing  and  amount  of  insurance  premiums,  service  and 
administration fees, and loan origination fees;
Deferred acquisition costs
The realization of deferred tax assets, and recognition and measurement of uncertain tax positions; and
Other  matters  that  affect  the  reported  amounts  and  disclosure  of  contingencies  in  the  consolidated  financial 
statements

Although  these  and  other  estimates  and  assumptions  are  based  on  the  best  available  estimates,  actual  results  could  differ 
materially from management’s estimates.

F-12

 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Business Combination Accounting

The Company accounts for business combinations by applying the acquisition method of accounting. The acquisition method 
requires, among other things, that the assets acquired and liabilities assumed in a business combination be measured at fair 
value as of the closing date of the acquisition. The net assets acquired may consist of tangible and intangible assets and the 
excess of purchase price over the fair value of identifiable net assets acquired, or goodwill. The determination of estimated 
useful  lives  and  the  allocation  of  the  purchase  price  to  the  intangible  assets  requires  significant  judgment  and  affects  the 
amount of future amortization and possible impairment charges. Contingent consideration, if any, is measured at fair value on 
the date of acquisition. The fair value of any contingent consideration liability is remeasured at each reporting date with any 
change recorded in other expense in the consolidated statements of operations. Acquisition and transaction costs are expensed 
as incurred. 

In certain instances, the Company may acquire less than 100% ownership of an entity, resulting in the recording of a non-
controlling interest. The measurement of assets and liabilities acquired and non-controlling interest is initially established at a 
preliminary  estimate  of  fair  value,  which  may  be  adjusted  during  the  measurement  period,  primarily  due  to  the  results  of 
valuation studies applicable to the business combination. 

Acquisitions that do not meet the criteria for the acquisition method of accounting are accounted for as acquisitions of assets. 

Dispositions and Assets and Liabilities Held for Sale

The  results  of  operations  of  a  business  that  has  either  been  disposed  of  or  are  classified  as  held  for  sale  are  reported  in 
discontinued operations if the disposal of the business represents a strategic shift that has (or will have) a major effect on an 
entity’s operations and financial results. The Company carries assets and liabilities held for sale at the lower of carrying value 
on the date the asset is initially classified as held for sale or fair value less costs to sell. At the time of reclassification to held 
for sale, the Company ceases the recording of depreciation and amortization on assets transferred.

Accounting policies specific to our dispositions and assets and liabilities held for sale are described in more detail in Note (4) 
Dispositions and Assets and Liabilities Held for Sale.

Fair Value Measurement

Fair value is defined as the price that would be received to sell an asset or paid to transfer a liability in an orderly transaction 
between market participants at the measurement date.

The  valuation  hierarchy  is  based  upon  the  transparency  of  inputs  to  the  valuation  of  an  asset  or  liability  as  of  the 
measurement date. The three levels, from highest to lowest, are defined as follows:

• Level  1  –  Unadjusted,  quoted  prices  in  active  markets  for  identical  assets  or  liabilities  that  the  Company  has  the 
ability to access at the measurement date.

• Level 2 – Significant inputs other than quoted prices that are observable for the asset or liability, either directly or 
indirectly  through  corroboration  with  observable  market  data.  Level  2  inputs  include  quoted  prices  for  similar 
instruments  in  active  markets,  and  inputs  other  than  quoted  prices  that  are  observable  for  the  asset  or  liability.  The 
types of financial assets and liabilities carried at Level 2 are valued based on one or more of the following:

a)  Quoted prices for similar assets or liabilities in active markets;
b) Quoted prices for identical or similar assets or liabilities in nonactive markets;
c)  Pricing models whose inputs are observable for substantially the full term of the asset or liability;
d)  Pricing  models  whose  inputs  are  derived  principally  from  or  corroborated  by  observable  market  data 
through correlation or other means for substantially the full term of the asset or liability.

• Level 3 – Significant inputs that are unobservable inputs for the asset or liability, including the Company’s own data 
and assumptions that are used in pricing the asset or liability.

The availability of observable inputs can vary depending on the financial asset or liability and is affected by a wide variety of 

F-13

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

factors, including, for example, the type of product, whether the product is new, whether the product is traded on an active 
exchange or in the secondary market, and the current market conditions. To the extent that valuation is based on models or 
inputs  that  are  less  observable  or  unobservable  in  the  market,  the  determination  of  fair  value  requires  more  judgment. 
Accordingly,  the  degree  of  judgment  exercised  by  the  Company  in  determining  fair  value  is  greatest  for  instruments 
categorized within Level 3 of the fair value hierarchy. In certain cases, the inputs used to measure fair value may fall into 
different levels of the fair value hierarchy. In such cases, for disclosure purposes, the level in the fair value hierarchy within 
which the fair value measurement in its entirety is determined based on the lowest level input that is significant to the fair 
value measurement in its entirety. Tiptree’s assessment of the significance of a particular input to the fair value measurement 
in  its  entirety  requires  judgment  and  the  consideration  of  factors  specific  to  the  instrument.  From  time  to  time,  Tiptree’s 
assets  and  liabilities  will  transfer  between  one  level  to  another  level.  It  is  Tiptree’s  policy  to  recognize  transfers  between 
different levels at the end of each reporting period. 

Tiptree  utilizes  both  observable  and  unobservable  inputs  in  its  valuation  methodologies.  Observable  inputs  include 
benchmark yields, reported trades, broker-dealer quotes, issuer spreads, benchmark securities, bids, offers and reference data. 
In addition, specific issuer information and other market data is used. For broker quotes, quotes are obtained from sources 
recognized to be market participants. Unobservable inputs may include expected cash flow streams, default rates, supply and 
demand considerations and market volatility. 

Fair Value Option

In addition to the financial instruments that the Company is required to measure at fair value, the Company has elected to 
make  an  irrevocable  election  to  utilize  fair  value  as  the  initial  and  subsequent  measurement  attribute  for  certain  eligible 
financial  assets  and  liabilities.  Unrealized  gains  and  losses  on  items  for  which  the  fair  value  option  has  been  elected  are 
reported in Net realized and unrealized gains (losses) within the consolidated statements of operations. The decision to elect 
the fair value option is determined on an instrument-by-instrument basis and must be applied to an entire instrument and is 
irrevocable once elected. 

Derivative Financial Instruments and Hedging

The  Company  utilizes  derivative  financial  instruments  as  part  of  its  overall  investment  and  hedging  activities.  Derivative 
contracts  are  subject  to  additional  risk  that  can  result  in  a  loss  of  all  or  part  of  an  investment.  The  Company’s  derivative 
activities  are  primarily  entered  into  in  order  to  manage  underlying  credit  risk,  market  risk,  interest  rate  risk  and  currency 
exchange  rate  risk.  As  a  matter  of  policy,  derivatives  are  not  used  for  speculative  purposes.  Derivative  instruments  are 
measured at fair value on a recurring basis and are included in other investments or other liabilities and accrued expenses on 
the consolidated balance sheets. See Note (10) Derivative Financial Instruments and Hedging.

The Fortegra Additional Warrants (Warburg) are classified as a derivative liability given that (i) the holder can exercise the 
warrant  for  a  variable  number  of  shares  and  (ii)  and  the  value  of  the  warrant  varies  inversely  with  the  value  of  Fortegra’s 
common stock. As such, the derivative liability is marked to fair value at each reporting period and its change in fair value is 
recorded in other expenses. See Note (10) Derivative Financial Instruments and Hedging, Note (12) Fair Value of Financial 
Instruments and Note (17) Stockholders' Equity for additional information.

Stock Based Compensation

The Company accounts for share-based compensation issued to employees, directors, and affiliates of the Company using the 
current fair value methodology based on the type of vesting condition – time based, performance based or market based or 
combination. See Note (19) Stock Based Compensation.

The Company initially measures the cost of all share-based compensation incentive awards at fair value on the date of grant, 
whether accounted for as an equity or liability award. The compensation cost is recognized over the required service period, 
generally  defined  as  the  vesting  period  using  the  straight-line  method.  When  the  share-based  compensation  awards  are 
accounted for as equity awards, the compensation cost is charged to expense with a corresponding credit to additional paid-in 
capital. If the share-based compensation awards are accounted for as liability awards, their fair value is remeasured at each 
reporting period, with the compensation cost charged to expense with a corresponding credit to other liabilities.

Grants of restricted stock units (RSUs) and options are accounted for as equity based upon their expected settlement method. 
The Company recognizes the cost of such awards over the vesting period using the straight-line method and uses the graded-

F-14

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

vesting  method  to  recognize  compensation  expense  for  the  performance  vesting  RSUs.  Compensation  expense  will  be 
recognized  to  the  extent  that  it  is  probable  that  the  performance  condition  will  be  achieved.  The  Company  reassesses  the 
probability of satisfaction of the performance condition for the performance vesting RSUs for each reporting period.

Income Taxes

Deferred tax assets and liabilities are determined using the asset and liability method. Under this method, deferred tax assets 
and liabilities are established for future tax consequences of temporary differences between the financial statement carrying 
amounts of assets and liabilities and their tax basis. Deferred tax assets and liabilities are measured using enacted tax rates 
expected to apply to taxable income in the year in which those temporary differences are expected to reverse. A valuation 
allowance is established when necessary to reduce a deferred tax asset to the amount expected to be realized. Several of the 
Company’s subsidiaries file state tax returns on a standalone basis. As of June 21, 2022, Fortegra began filing federal and 
state  tax  returns  on  a  stand-alone  basis.  These  U.S.  federal  and  state  income  tax  returns,  when  filed,  will  be  subject  to 
examination by the Internal Revenue Service and state departments of revenue. See Note (20) Income Taxes.

The Company evaluates tax positions taken or expected to be taken in the course of preparing its tax returns to determine 
whether  the  tax  positions  are  “more  likely  than  not”  of  being  sustained  by  the  applicable  tax  authority.  The  Company’s 
provision or benefit for income taxes is adjusted accordingly for tax positions not deemed to meet the more likely than not 
threshold. The Company’s policy is to account for interest as a component of interest expense and penalties as a component 
of other expenses.

Earnings Per Share

The  Company  presents  both  basic  and  diluted  earnings  per  Common  Share  in  its  consolidated  financial  statements  and 
footnotes thereto. Basic earnings per Common Share (Basic EPS) excludes dilution and is computed by dividing net income 
or loss available to common stockholders by the weighted average number of common shares outstanding, which includes 
vested  RSUs,  for  the  period.  Diluted  earnings  per  Common  Share  (Diluted  EPS)  reflects  the  potential  dilution  that  could 
occur if securities or other contracts to issue common shares were exercised or converted into common shares where such 
exercise or conversion would result in a lower earnings per share amount.

The Company calculates EPS using the two-class method, which is an earnings allocation formula that determines EPS for 
common  shares  and  participating  securities.  Unvested  RSUs  contain  non-forfeitable  rights  to  distributions  or  distribution 
equivalents (whether paid or unpaid) and are participating securities that are included in the computation of EPS using the 
two-class method. Accordingly, all earnings (distributed and undistributed) are allocated to common shares and participating 
securities  based  on  their  respective  rights  to  receive  distributions.  The  participating  securities  do  not  have  a  contractual 
obligation to absorb losses and are only allocated in periods where there is income.

See Note (22) Earnings Per Share, for EPS computations.

Investments

The  Company  records  all  investment  transactions  on  a  trade-date  basis.  Realized  gains  (losses)  are  determined  using  the 
specific-identification method. The Company classifies its investments in debt securities as available for sale, trading or held-
to-maturity based on the Company’s intent and ability to hold the debt security to maturity. The Company did not have any 
held-to-maturity securities at December 31, 2023 and 2022. See Note (6) Investments.

Available for Sale Securities, at Fair Value (AFS) 

AFS are securities that are not classified as trading or held-to-maturity and are intended to be held for indefinite periods of 
time. AFS securities include those debt securities that management may sell as part of its asset/liability management strategy 
or in response to changes in interest rates, resultant prepayment risk or other factors. AFS securities are held at fair value on 
the  consolidated  balance  sheet  with  changes  in  fair  value  including  non-credit  related  losses,  net  of  related  tax  effects, 
recorded in the AOCI component of stockholders’ equity in the period of change. Upon the disposition of an AFS security, 
the  Company  reclassifies  the  gain  or  loss  on  the  security  from  AOCI  to  net  realized  and  unrealized  gains  (losses)  on  the 
consolidated statements of operations. 

F-15

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

For AFS securities, the Company reviews its securities portfolio for impairment and determines if impairment is related to 
credit  loss  or  non-credit  loss.  In  making  the  assessment  of  whether  a  loss  is  from  credit  or  other  factors,  management 
considers  the  extent  to  which  fair  value  is  less  than  amortized  cost,  any  changes  to  the  rating  of  the  security  by  a  rating 
agency,  and  adverse  conditions  related  to  the  security,  among  other  factors.  If  this  assessment  indicates  that  a  credit  loss 
exists, the present value of cash flows expected to be collected from the security is compared to the amortized cost basis of 
the security. If the present value of cash flows is less than the amortized cost basis, a credit loss exists and an allowance is 
created, limited by the amount that the fair value is less than the amortized cost basis.

Subsequent activity related to the credit loss component (e.g. write-offs, recoveries) is recognized as part of the allowance for 
credit losses on AFS securities. For AFS securities which have an expectation of zero risk of nonpayment of the amortized 
cost basis (e.g. U.S. Treasury securities or agency securities), the expected credit loss is zero.

Loans, at Fair Value

Loans,  at  fair  value  is  substantially  comprised  of  (i)  corporate  loans  and  (ii)  loans  originated  by  the  Company’s  mortgage 
finance business. Changes in their fair value are reported within net realized and unrealized gains (losses) in our consolidated 
statements of operations. 

Corporate Loans 

Corporate  loans  are  comprised  of  middle  market  loans  and  bank  loans  which  are  carried  at  fair  value.  In  general,  the  fair 
value is obtained from an independent pricing service which provides coverage of secondary market participants. The values 
represent  a  composite  of  mark-to-market  bid/offer  prices.  In  certain  circumstances,  the  Company  will  make  its  own 
determination of fair value of loans based on internal models and other unobservable inputs.

Mortgage Loans Held for Sale

Mortgage  loans  held  for  sale  represent  loans  originated  and  held  until  sold  to  secondary  market  investors.  Such  loans  are 
typically warehoused for a period after origination or purchase before sale into the secondary market. Loans are sold either 
servicing  released,  or  in  select  instances,  servicing  retained  into  the  secondary  loan  market.  The  Company  has  elected  to 
measure all mortgage loans held for sale at fair value. These loans are considered sold when the Company surrenders control 
to the purchaser. The gains or losses on sales of such loans, net of any accrual for standard representations and warranties, are 
reported in operating results as a component of net realized and unrealized gains (losses) in the consolidated statements of 
operations in the period when the sale occurs.

Equity Securities

Equity securities are investments consisting of equity securities that are purchased principally for the purpose of selling them 
in  the  near  term.  Changes  in  fair  value  are  recorded  in  net  realized  and  unrealized  gains  (losses)  on  investments  on  the 
consolidated statements of operations in the period of change.

Other Investments

Corporate Bonds

Corporate bonds are generally classified under Level 2 in the fair value hierarchy and fair value is based on quoted market 
prices. We perform internal price verification procedures to ensure that the prices provided are reasonable.

Vessels, net

Investments in vessels, net are carried at cost (inclusive of capitalized acquisition costs, where applicable) less accumulated 
depreciation.  Subsequent  expenditures  are  also  capitalized  when  they  appreciably  extend  the  life,  increase  the  earning 
capacity  or  improve  the  efficiency  or  safety  of  the  vessels;  otherwise,  these  amounts  are  expensed  as  incurred.  Vessels 
acquired are recognized at their fair value as of the date of the acquisition.

F-16

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Depreciation is computed using the straight-line method over the vessel’s estimated remaining useful life, after considering 
the estimated salvage value. A vessel’s salvage value is equal to the product of its lightweight tonnage and estimated scrap 
rate.  Vessels  are  depreciated  from  the  date  of  their  acquisition  through  their  remaining  estimated  useful  life.  Upon 
transferring  the  vessels  and  related  assets  to  held  for  sale  on  the  consolidated  balance  sheets,  the  vessels  are  no  longer 
depreciated.

Vessels are reviewed for potential impairment when events or changes in circumstances indicate that the carrying amount of a 
particular vessel may not be fully recoverable. Potential impairment indicators are primarily based upon a comparison of the 
market value of a vessel to its carrying value. Market values are based upon quoted prices from industry-recognized sources. 
The  Company  evaluates  market  quotes  of  vessels  for  reasonableness  by  comparison  to  available  market  transactions  or 
internal valuation models. An impairment charge would be recognized if the estimated undiscounted future net cash flows 
expected to result from the operation and subsequent disposal of the vessel are less than the vessel’s carrying amount. 

The  Company  concluded  during  its  annual  impairment  testing  its  remaining  two  vessels  were  partially  impaired  as  of 
December 31, 2023. The Company had no impairment as of year ended 2022. As of December 31, 2023, all remaining tanker 
and dry-bulk vessels had been sold. See Note (4) Dispositions and Assets and Liabilities Held for Sale.

Cash and Cash Equivalents

Cash and cash equivalents consist of cash on hand, cash held in banks, money market funds, and all highly liquid investments 
of sufficient credit quality purchased with an initial maturity of three months or less to be cash equivalents, including U.S. 
and foreign government securities.

Restricted Cash

The  Company’s  restricted  cash  primarily  consists  of  cash  for  unremitted  premiums  received  from  agents  and  insurers, 
fiduciary cash for reinsurers and pledged assets for the protection of policy holders in various state jurisdictions. Restricted 
cash also includes cash posted as collateral under credit facilities to maintain borrowing base sufficiency, borrower escrow 
funds for taxes, insurance, rate-lock fees and servicing related escrow funds and collateral on warehouse borrowings.

Notes and Accounts Receivable, Net

Notes Receivable, Net

The  Company’s  notes  receivable,  net  includes  receivables  related  to  the  insurance  business  for  its  premium  financing 
programs.  The  Company  accrues  interest  income  on  its  notes  receivable  based  on  the  contractual  terms  of  the  respective 
note. The Company monitors all notes receivable for delinquency and provides for estimated losses for specific receivables 
that are not likely to be collected. In addition to allowances for bad debt for specific notes receivable, a general provision for 
bad debt is estimated for the Company’s notes receivable based on history. Account balances are generally charged against 
the allowance when the Company believes it is probable that the note receivable will not be recovered and has exhausted its 
contractual  and  legal  remedies.  Generally,  receivables  overdue  more  than  120  days  are  written  off  when  the  Company 
determines it has exhausted reasonable collection efforts and remedies, see Note (7) Notes and Accounts Receivable, net.

Accounts and Premiums Receivable, Net

Accounts and premiums receivable, net are primarily trade receivables from the insurance business that are carried at their 
approximate  fair  value.  Accounts  and  premiums  receivable  from  the  Company’s  insurance  business  consist  primarily  of 
advance commissions and agents' balances in course of collection and billed but not collected policy premiums, presented net 
of the allowance for doubtful accounts. For policy premiums that have been billed but not collected, the Company records a 
receivable on its consolidated balance sheets for the full amount of the premium billed, with a corresponding liability, net of 
its commission, to insurance carriers. The Company earns interest on the premium cash during the period of time between 
receipt  of  the  funds  and  payment  of  these  funds  to  insurance  carriers.  The  Company  maintains  an  allowance  for  doubtful 
accounts based on an estimate of uncollectible accounts. 

Retrospective commissions receivable, Trust receivables and Other receivables

F-17

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Retrospective  commissions  receivable,  trust  receivables  and  other  receivables  are  primarily  trade  receivables  from  the 
insurance business that are carried net of allowance at their approximate fair value.

Reinsurance Recoverable & Prepaid Reinsurance Premiums

Through  the  insurance  business,  the  Company  has  various  reinsurance  agreements  in  place  whereby  the  amount  of  risk  in 
excess of its retention goals is reinsured by unrelated domestic and foreign insurance companies. The Company is required to 
pay  losses  even  if  a  reinsurer  fails  to  meet  its  obligations  under  the  applicable  reinsurance  agreement.  Reinsurance 
receivables  include  amounts  related  to  paid  benefits,  unpaid  benefits  and  prepaid  reinsurance  premiums.  Reinsurance 
receivables are based upon estimates and are reported on the consolidated balance sheets separately as assets, as reinsurance 
does not relieve the Company of its legal liability to policyholders. Management continually monitors the financial condition 
and  agency  ratings  of  the  Company’s  reinsurers  and  believes  that  the  reinsurance  receivables  accrued  are  collectible. 
Balances recoverable from reinsurers and amounts ceded to reinsurers relating to the unexpired portion of reinsured policies 
are  presented  as  assets.  Experience  refunds  from  reinsurers  are  recognized  based  on  the  underwriting  experience  of  the 
underlying contracts.

Deferred Acquisition Costs

The Company defers certain costs of acquiring new and renewal insurance policies and other products as follows within the 
Company’s  insurance  business.  Amortization  of  deferred  acquisition  costs  was  $583,589,  $479,125,  and  $375,052  for  the 
years ended December 31, 2023, 2022 and 2021, respectively.

Insurance  policy  related  deferred  acquisition  costs  are  limited  to  direct  costs  that  resulted  from  successful  contract 
transactions and would not have been incurred by the Company’s insurance company subsidiaries had the transactions not 
occurred. These capitalized costs are amortized as the related premium is earned.

Other deferred acquisition costs are limited to prepaid direct costs, typically commissions and contract transaction fees, that 
resulted  from  successful  contract  transactions  and  would  not  have  been  incurred  by  the  Company  had  the  transactions  not 
occurred. These capitalized costs are amortized as the related service and administrative fees are earned.

The Company evaluates whether all deferred acquisition costs are recoverable at year end, and considers investment income 
in  the  recoverability  analysis  for  insurance  policy  related  deferred  acquisition  costs.  As  a  result  of  the  Company’s 
evaluations, no write-offs for unrecoverable deferred acquisition costs were recognized during the years ended December 31, 
2023, 2022 and 2021.

Goodwill and Intangible Assets, net

The initial measurement of goodwill and intangibles requires judgment concerning estimates of the fair value of the acquired 
assets  and  liabilities.  Goodwill  and  indefinite-lived  intangible  assets  are  not  amortized  but  subject  to  tests  for  impairment 
annually or if events or circumstances indicate it is more likely than not they may be impaired. Finite-lived intangible assets 
are amortized over their estimated useful lives principally using a pattern of economic benefit for customer relationships and 
a  straight-line  method  for  other  intangible  assets.  Finite-lived  intangible  assets  are  subject  to  impairment  if  events  or 
circumstances  indicate  a  possible  inability  to  realize  the  carrying  amount.  The  Company  carries  intangible  assets,  which 
represent  customer  and  agent  relationships,  trade  names,  insurance  licenses  (certificates  of  authority  granted  by  individual 
state departments of insurance), the value of in-force insurance policies acquired, software acquired or internally developed 
and fishing licenses. Management has deemed the insurance licenses to have an indefinite useful life. Costs incurred to renew 
or maintain insurance licenses are recorded as operating costs in the period in which they arise. See Note (9) Goodwill and 
Intangible Assets, net.

Other Assets

Other  assets  primarily  consist  of  mortgage  servicing  rights,  loans  eligible  for  repurchase,  right  of  use  assets,  prepaid 
expenses, and furniture, fixtures and equipment, net. See Note (15) Other Assets and Other Liabilities and Accrued Expenses.

F-18

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Mortgage Servicing Rights

Mortgage servicing rights represent the fair value of the right to service the underlying mortgage loans. The estimated fair 
value is provided by a third-party valuation service and represents the price that a willing buyer would currently pay for the 
Company’s mortgage servicing rights. Changes in fair value are recorded in net realized and unrealized gains (losses) on the 
consolidated statements of operations in the period of change.

Debt, net

Debt is carried on the consolidated balance sheets at an amount equal to the unpaid principal balance, net of any remaining 
unamortized  discount  or  premium  and  direct  and  any  incremental  costs  attributable  to  issuance.  Discounts,  premiums  and 
direct and incremental costs are amortized as a component of interest expense in the consolidated statements of operations 
over the life of the debt. See Note (11) Debt, net. 

Unearned Premiums

Premiums written are earned over the life of the respective policy using pro rata, Rule of 78’s, modified Rule of 78’s, or other 
methods  as  appropriate  for  the  contract.  Unearned  premiums  represent  the  portion  of  premiums  that  will  be  earned  in  the 
future. A premium deficiency reserve is recorded if anticipated losses, loss adjustment expenses, deferred acquisition costs 
and  policy  maintenance  costs  exceed  the  recorded  unearned  premium  reserve  and  anticipated  investment  income.  As  of 
December 31, 2023 and 2022, no deficiency reserves were recorded.

Policy Liabilities and Unpaid Claims

Policyholder account balances relate to investment-type individual annuity contracts in the accumulation phase. Policyholder 
account  balances  are  carried  at  accumulated  account  values,  which  consist  of  deposits  received,  plus  interest  credited,  less 
withdrawals and assessments. Minimum guaranteed interest credited to these contracts ranges from 3.0% to 4.0%. 

The  Company’s  claims  are  generally  reported  and  settled  quickly,  resulting  in  consistent  historical  loss  development 
patterns. The Company’s actuaries apply a variety of generally accepted actuarial methods to the historical loss development 
patterns, to derive cumulative development factors. These cumulative development factors are applied to reported losses for 
each accident quarter to compute ultimate losses. The indicated required reserve is the difference between the ultimate losses 
and the reported losses. The actuarial methods used include but are not limited to the chain ladder method, the Bornhuetter-
Ferguson  method,  and  the  expected  loss  ratio  method.  The  actuarial  analyses  are  performed  on  a  basis  gross  of  ceded 
reinsurance, and the resulting factors and estimates are then used in calculating the net loss reserves which take into account 
the impact of reinsurance. The Company has not made any changes to its methodologies for determining claim reserves in the 
periods presented.

Credit  life  and  accidental  death  and  dismemberment  (AD&D)  unpaid  claims  reserves  include  claims  in  the  course  of 
settlement  and  incurred  but  not  reported  (IBNR).  Credit  disability  unpaid  claims  reserves  also  include  continuing  claim 
reserves  for  open  disability  claims.  For  all  other  product  lines,  unpaid  claims  reserves  include  case  reserves  for  reported 
claims  and  bulk  reserves  for  IBNR  claims.  The  Company  uses  a  number  of  algorithms  in  establishing  its  unpaid  claims 
reserves. These algorithms are used to calculate unpaid claims as a function of paid losses, earned premium, reported incurred 
losses, target loss ratios, and in-force amounts or a combination of these factors. 

Anticipated  future  loss  development  patterns  form  a  key  assumption  underlying  these  analyses.  Generally,  unpaid  claims 
reserves, and associated incurred losses, are impacted by loss frequency, which is the measure of the number of claims per 
unit of insured exposure, and loss severity, which is based on the average size of claims. Factors affecting loss frequency and 
loss  severity  may  include  changes  in  claims  reporting  patterns,  claims  settlement  patterns,  judicial  decisions,  legislation, 
economic conditions, morbidity patterns and the attitudes of claimants towards settlements. 

The unpaid claims reserves represent the Company’s best estimates at a given time, based on the projections and analyses 
discussed above. Actual claim costs are dependent upon a number of complex factors such as changes in doctrines of legal 
liabilities and damage awards. These factors are not directly quantifiable, particularly on a prospective basis. The Company 
periodically  reviews  and  updates  its  methods  of  making  such  unpaid  claims  reserve  estimates  and  establishing  the  related 

F-19

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

liabilities  based  on  our  actual  experience.  The  Company  has  not  made  any  changes  to  its  methodologies  for  determining 
unpaid claims reserves in the periods presented.

In accordance with applicable statutory insurance company regulations, the Company’s recorded unpaid claims reserves are 
evaluated  by  appointed  independent  third-party  actuaries,  who  perform  this  function  in  compliance  with  the  Standards  of 
Practice  and  Codes  of  Conduct  of  the  American  Academy  of  Actuaries.  The  independent  actuaries  perform  their  actuarial 
analyses annually and prepare opinions, statements, and reports documenting their determinations. For December 31, 2023 
and 2022, our appointed independent third-party actuaries found the Company’s reserves to be adequate.

Deferred Revenue

Deferred revenues represent the portion of income that will be earned in the future attributable to motor club memberships 
and non-insurance service contracts that are earned over the respective contract periods using pro rata, Rule of 78’s, modified 
Rule of 78’s, or other methods as appropriate for the contract. A deficiency reserve would be recorded if anticipated contract 
benefits,  deferred  acquisition  costs  and  contract  service  costs  exceed  the  recorded  deferred  revenues  and  anticipated 
investment income. As of December 31, 2023 and 2022, no deficiency reserves were recorded.

Other Liabilities and Accrued Expenses

Other liabilities and accrued expenses primarily consist of lease liabilities, accounts payable and accrued expenses, deferred 
tax liabilities, net, securities sold, not yet purchased, commissions payable and accrued interest payable. See Note (15) Other 
Assets and Other Liabilities and Accrued Expenses.

Revenue Recognition

The Company earns revenues from a variety of sources:

Earned Premiums, Net

Net  earned  premium  is  from  direct  and  assumed  earned  premium  consisting  of  revenue  generated  from  the  direct  sale  of 
insurance policies by the Company’s distributors and premiums written for insurance policies by another carrier and assumed 
by  the  Company.  Whether  direct  or  assumed,  the  premium  is  earned  over  the  life  of  the  respective  policy  using  methods 
appropriate to the pattern of losses for the type of business. Methods used include the Rule of 78's, modified Rule of 78’s, pro 
rata,  and  other  actuarial  methods.  Management  selects  the  appropriate  method  based  on  available  information,  and 
periodically reviews the selections as additional information becomes available. Direct and assumed premiums are offset by 
premiums ceded to the Company’s reinsurers, including producer owned reinsurance companies (PORCs), earned in the same 
manner. The amount ceded is proportional to the amount of risk assumed by the reinsurer.

Service and Administrative Fees 

The Company earns service and administrative fees from a variety of activities. Such fees are typically positively correlated 
with transaction volume and are recognized as revenue as they become both realized and earned. 

Service and administrative fees are generated from non-insurance programs including warranty service contracts, motor clubs 
and  other  services.  Service  and  administrative  fees  are  recognized  consistent  with  the  earnings  recognition  pattern  of  the 
underlying  insurance  policies,  debt  cancellation  contracts  and  motor  club  memberships  being  administered,  using  pro  rata, 
Rule of 78’s, modified Rule of 78’s, or other methods as appropriate for the contract. Management selects the appropriate 
method based on available information, and periodically reviews the selections as additional information becomes available.

In  addition,  ceding  fees  paid  by  our  reinsurers  on  ceded  insurance  premiums  are  recorded  on  an  earned  basis.  These  fees 
reimburse us for administrative, underwriting, and acquisition expenses. These fees are earned in subsequent periods over the 
remaining term of the policy.

Ceding Commissions

Ceding commissions earned under reinsurance agreements are based on contractual formulas that take into account, in part, 

F-20

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

underwriting  performance  and  investment  returns  experienced  by  the  assuming  companies.  As  experience  changes, 
adjustments  to  the  ceding  commissions  are  reflected  in  the  period  incurred  and  are  based  on  the  claim  experience  of  the 
related  policy.  The  adjustment  is  calculated  by  adding  the  earned  premium  and  investment  income  from  the  assets  held  in 
trust for the Company’s benefit less earned commissions, incurred claims and the reinsurer's fee for the coverage. 

Vessel Related Revenue

The Company generates its revenues from charterers for the charter hire of its vessels. Vessels are chartered under time or 
voyage charters, where a contract is entered into for the use of a vessel for a specific voyage or a specific period of time and 
at a specified daily charter rate. Charter revenues are recognized as earned on a straight-line basis over the term of the charter 
as service is provided. 

Revenue  is  recognized  when  a  charter  agreement  exists,  the  vessel  is  made  available  to  the  charterer  and  collection  of  the 
related revenue is reasonably assured. Unearned revenue includes revenue received prior to the balance sheet date relating to 
services to be rendered after the balance sheet date. Vessel related revenue is recorded in other investment income as a part of 
other revenue. See Note (16) Other Revenue and Other Expenses.

Policy and Contract Benefits

Member Benefit Claims

Member  benefit  claims  represent  claims  paid  on  behalf  of  contract  holders  directly  to  third-party  providers  for  roadside 
assistance  as  well  as  warranty  and  service  contracts  for  the  repair  or  replacement  of  covered  products.  Claims  can  also  be 
paid directly to contract holders as a reimbursement payment, provided supporting documentation of loss is submitted to the 
Company. Claims are recognized as expense when incurred.

Net Losses and Loss Adjustment Expenses

Net  losses  and  loss  adjustment  expenses  represent  losses  and  related  claim  adjudication  and  processing  costs  on  insurance 
contract claims, net of amounts ceded. Net losses include actual claims paid and the change in unpaid claim reserves.

Commissions Payable and Expense

Commissions are paid to distributors and retailers selling credit insurance policies, motor club memberships, mobile device 
protection,  and  vehicle  service  contracts,  and  are  generally  deferred  and  expensed  in  proportion  to  the  earning  of  related 
revenue. Credit insurance commission rates, in many instances, are set by state regulators and are also impacted by market 
conditions.  In  certain  instances,  credit  insurance  commissions  are  subject  to  retrospective  adjustment  based  on  the 
profitability of the related policies. Under these retrospective commission arrangements, the producer of the credit insurance 
policies receives a retrospective commission if the premium generated by that producer in the accounting period exceeds the 
costs associated with those policies, which includes the Company’s administrative fees, claims, reserves, and premium taxes. 
The Company analyzes the retrospective commission calculation periodically for each producer and, based on the analysis 
associated with each such producer, the Company records a liability for any positive net retrospective commission earned and 
due to the producer or, conversely, records a receivable, net of allowance, for amounts due from such producer for instances 
where  the  net  result  of  the  retrospective  commission  calculation  is  negative.  Commissions  payable  are  included  in  other 
liabilities and accrued expenses. See Note (15) Other Assets and Other Liabilities and Accrued Expenses.

F-21

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Recent Accounting Standards

Recently Adopted Accounting Pronouncements

Accounting Standard 
Update

2020-06, Debt with 
Conversion and Other 
Options (Subtopic 
470-20) and Derivatives 
and Hedging - Contracts 
in Entity’s Own Equity 
(Subtopic 815-40)

2021-08, Business 
Combinations (Topic 
805) - Accounting for 
Contract Assets and 
Contract Liabilities from 
Contracts with 
Customers

2019-12, Income Taxes 
(Topic 740): 
Simplifying the 
Accounting for Income 
Taxes

Description
The standard simplifies the accounting for certain financial instruments. The 
guidance reduces the number of accounting models for convertible debt 
instruments by eliminating the cash conversion and beneficial conversion 
models and simplifies the derivative scope exception guidance pertaining to 
equity classification of contracts in an entity’s own equity. The new standard 
also introduces additional disclosures for convertible debt and freestanding 
instruments that are indexed to and settled in an entity’s own equity. This 
standard amends the diluted earnings per share guidance, including the 
requirement to use the if-converted method for all convertible instruments. 
Either a full or modified retrospective method of transition is permissible for 
the adoption of this standard.

This standard addresses diversity in practice and inconsistency related to 
recognition of an acquired contract liability, and payment terms and their effect 
on subsequent revenue recognized by the acquirer. This standard is effective 
for annual periods beginning after December 15, 2023, including interim 
periods within those fiscal years. Entities should apply the provisions of the 
new standard prospectively to business combinations occurring on or after the 
effective date of the standard. Early adoption is permitted, including in an 
interim period. The Company early adopted this standard and applied it to all 
2022 business combinations. 
The standard eliminates the need for an organization to analyze whether the 
following apply in a given period (1) exception to the incremental approach for 
intraperiod tax allocation, (2) exceptions to accounting for basis differences 
when there are ownership changes in foreign investments and (3) exceptions in 
interim period income tax accounting for year-to-date losses that exceed 
anticipated losses. The ASU also is designed to improve financial statement 
preparers’ application of income tax-related guidance and simplify GAAP for 
(1) franchise taxes that are partially based on income, (2) transactions with a 
government that result in a step-up in the tax basis of goodwill, (3) separate 
financial statements of legal entities that are not subject to tax, and (4) enacted 
changes in tax laws in interim periods.

Impact on Financial 
Statements
Adoption Date
January 1, 2022 The adoption of the 

standard did not materially 
impact the Company’s 
consolidated financial 
statements.

January 1, 2022 The adoption of the 

standard did not materially 
impact the Company’s 
consolidated financial 
statements.

January 1, 2021 The standard makes 

changes to areas of tax 
accounting for transactions 
and situations which do not 
currently apply to the 
Company’s activity, so the 
adoption of the standard has 
not had an impact the 
Company’s financial 
statements.

F-22

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Recently Issued Accounting Pronouncements, Not Yet Adopted

Accounting Standard 
Update

2020-04, Reference 
Rate Reform (Topic 
848): Facilitation of the 
Effects of Reference 
Rate Reform on 
Financial Reporting and 
2022-06 Reference Rate 
Reform (Topic 848): 
Deferral of the Sunset 
Date of Topic 848

2023-07 (Topic 280) 
Improvements to 
Reportable Segment 
Disclosures

2023-09, Income Taxes 
(Topic 740) 
Improvements to 
Income Tax Disclosures

Description

The amendments in these updates provide optional guidance for a limited 
period to ease the potential burden in accounting for (or recognizing the effects 
of) reference rate reform on financial reporting. The amendments provide 
optional expedients and exceptions for applying GAAP to contracts, hedging 
relationships, and other transactions that reference LIBOR or another reference 
rate expected to be discontinued because of reference rate reform if certain 
criteria are met. 

In November 2023, the Financial Accounting Standards Board (FASB) issued 
ASU No. 2023-07, Segment Reporting (Topic 280): Improvements to 
Reportable Segment Disclosures (ASU 2023-07), which requires an enhanced 
disclosure of significant segment expenses on an annual and interim basis. This 
guidance will be effective for the annual periods beginning the year ended 
December 31, 2024, and for interim periods beginning January 1, 2025. Early 
adoption is permitted. Upon adoption, the guidance should be applied 
retrospectively to all prior periods presented in the financial statements. 

The amendments in this Accounting Standards Update enhance the 
transparency and decision usefulness of income tax disclosures. Investors, 
lenders, creditors, and other allocators of capital (collectively, “investors”) 
indicated that the existing income tax disclosures should be enhanced to 
provide information to better assess how an entity’s operations and related tax 
risks and tax planning and operational opportunities affect its tax rate and 
prospects for future cash flows. Investors currently rely on the rate 
reconciliation table and other disclosures, including total income taxes paid, to 
evaluate income tax risks and opportunities. While investors find these 
disclosures helpful, they suggested possible enhancements to better (1) 
understand an entity’s exposure to potential changes in jurisdictional tax 
legislation and the ensuing risks and opportunities, (2) assess income tax 
information that affects cash flow forecasts and capital allocation decisions, 
and (3) identify potential opportunities to increase future cash flows.

Impact on Financial 
Statements

The Company is 
evaluating its option to 
adopt the guidance when 
it is applicable.

The Company  does not 
expect the adoption of 
this guidance to have a 
material impact on our 
consolidated financial 
statements

The Company is 
evaluating timing on 
when to adopt the 
guidance when it is 
applicable.

Adoption Date
The standard is 
effective for all 
entities as of 
March 12, 2020, 
through 
December 31, 
2024. 

The amendments 
in this update are 
effective for 
annual periods 
beginning after 
December 31, 
2024.

The amendments 
in this update are 
effective for 
annual periods 
beginning after 
December 15, 
2024.

(3) Acquisitions

Acquisition of Premia Solutions Limited

On  February  6,  2023,  a  subsidiary  of  Fortegra  acquired  a  majority  of  the  equity  interests  in  Premia  for  total  cash 
consideration  of  approximately  $19,726,  net  of  cash  acquired  of  $3,873.  Premia  is  an  intermediate  provider  of  automotive 
protection products in the United Kingdom.

The  preliminary  purchase  price  allocation  has  been  developed  based  on  preliminary  estimates  of  fair  value  using  the 
historical  financial  statements  of  Premia  as  of  the  acquisition  date  and  is  subject  to  the  completion  of  management’s  final 
analysis. Identifiable assets acquired were primarily made up of goodwill and intangible assets. Management’s preliminary 
allocation  of  the  purchase  price  to  the  net  assets  acquired  resulted  in  the  recording  of  goodwill  and  intangible  assets  of 
$18,359  and  $18,152,  respectively,  which  the  Company  may  modify  during  the  one  year  period  allowed  for  purchase 
accounting adjustments during the measurement period. See Note (9) Goodwill and Intangible Assets, net. 

Acquisition of ITC Compliance GRP Limited 

On April 1, 2022, Fortegra Europe Limited, a subsidiary of the Company, acquired all of the equity interests of ITC for total 
cash consideration of approximately $15,000, net of cash acquired of $6,123, plus earn out payments based on achievement 
of  specific  performance  metrics.  ITC  is  a  provider  of  regulatory  support  and  compliance  services  to  the  retail  automotive 
sector in the United Kingdom.

Identifiable  assets  acquired  were  primarily  made  up  of  goodwill  and  intangible  assets.  Management’s  allocation  of  the 
purchase price to the net assets acquired resulted in the recording of goodwill and intangible assets of $8,044 and $10,964, 
respectively. See Note (9) Goodwill and Intangible Assets, net.

F-23

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

(4) Dispositions and Assets and Liabilities Held for Sale

Dispositions

As  of  December  31,  2023,  all  remaining  tanker  and  dry-bulk  vessels  had  been  sold.  During  the  year  ended  December  31, 
2022,  the  Company  completed  the  sale  of  three  dry  bulk  vessels  and  two  product  tankers  from  its  maritime  shipping 
operations. The Company recognized a net gain of $34,803, based on proceeds of $116,678 plus final settlement of assets. 
The transactions did not meet the requirements to be classified as discontinued operations.

Assets and Liabilities Held for Sale

The Company entered into a definitive agreement to sell Luxury, which was classified as held for sale at December 31, 2021. 
The  Company  deconsolidated  Luxury  effective  as  of  July  1,  2022  due  to  the  execution  of  an  amendment  to  the  definitive 
agreement to sell Luxury on that date. As of that date, Tiptree no longer had a variable interest in Luxury and all of the risks 
and  rewards  associated  with  Luxury  were  transferred  to  the  buyer.  The  transaction  did  not  meet  the  requirements  to  be 
classified as a discontinued operation.

Luxury’s earnings had no impact on net income (loss) attributable to common stockholders for the years ended December 31, 
2023, 2022 and 2021.

(5) Operating Segment Data

Tiptree  is  a  holding  company  that  allocates  capital  across  a  broad  spectrum  of  businesses,  assets  and  other  investments. 
Tiptree’s principal operating subsidiary, Fortegra, is a leading provider of specialty insurance, service contract products and 
related service solutions. Based on the quantitative analysis performed related to Accounting Standard Codification (“ASC”) 
280,  Segment  Reporting,  our  reportable  segments  are  Insurance  and  Mortgage.  We  refer  to  our  non-insurance  operations, 
assets and other investments, comprised of our Mortgage reportable segment and our non-reportable operating segments and 
other  business  activities,  as  Tiptree  Capital.  Corporate  activities  include  holding  company  interest  expense,  employee 
compensation and benefits, and other expenses.

Our  reportable  segments’  income  or  loss  is  reported  before  income  taxes  and  non-controlling  interests.  Segment  results 
incorporate  the  revenues  and  expenses  of  these  subsidiaries  since  they  commenced  operations  or  were  acquired. 
Intercompany transactions are eliminated.

Descriptions  of  our  Insurance  reportable  segment  and  Tiptree  Capital,  including  our  Mortgage  reportable  segment,  are  as 
follows:

Insurance operations are conducted through Fortegra, which is a leading provider of specialty insurance products and related 
services. Fortegra designs, markets and underwrites specialty property and casualty insurance products incorporating value-
added coverages and services for select target markets or niches. Fortegra’s products and services include niche commercial 
and personal lines, service contracts, and other insurance services.

Tiptree Capital:

Mortgage  operations  are  conducted  through  Reliance.  The  Company’s  mortgage  business  originates  loans  for  sale  to 
institutional investors, including GSEs and FHA/VA and services loans on behalf of Fannie Mae, Freddie Mac, and Ginnie 
Mae.

Other  includes  our  remaining  maritime  shipping  operations,  asset  management,  other  investments  (including  our  Invesque 
shares), and Luxury mortgage operations (deconsolidated effective as of July 1, 2022).

The  tables  below  present  the  components  of  revenue,  expense,  income  (loss)  before  taxes,  and  assets  for  our  reportable 
segments as well as Tiptree Capital - Other for the following periods: 

F-24

 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Total revenue
Total expense
Corporate expense
Income (loss) before taxes

Less: provision (benefit) for income taxes

Net income (loss)

Less: net income (loss) attributable to non-controlling interests
Net income (loss) attributable to common stockholders

Total revenues
Total expenses
Corporate expenses
Income (loss) before taxes

Less: provision (benefit) for income taxes

Net income (loss)

Less: net income (loss) attributable to non-controlling interests
Net income (loss) attributable to common stockholders

Total revenues
Total expenses
Corporate expenses
Income (loss) before taxes

Less: provision (benefit) for income taxes

Net income (loss)

Less: net income (loss) attributable to non-controlling interests
Net income (loss) attributable to common stockholders

For the Year Ended December 31, 2023
Tiptree Capital

Insurance

Mortgage

Other

$ 

$ 

1,593,070  $ 
(1,463,254)   

— 
129,816  $ 

53,864  $ 
(57,149) 
— 
(3,285)  $ 

2,097  $ 
(5,361) 
— 
(3,264)  $ 

$ 

$ 

For the Year Ended December 31, 2022

Tiptree Capital

Insurance

Mortgage

Other

$ 

$ 

1,248,796  $ 
(1,180,646) 
— 
68,150  $ 

70,246  $ 
(69,372)   

— 
874  $ 

78,710  $ 
(47,307) 
— 
31,403  $ 

$ 

$ 

For the Year Ended December 31, 2021

Tiptree Capital

Insurance

Mortgage

Other

$ 

$ 

984,130  $ 
(914,273) 
— 
69,857  $ 

111,295  $ 
(82,888)   

— 
28,407  $ 

105,089  $ 
(87,879) 
— 
17,210  $ 

$ 

$ 

Total
1,649,031 
(1,525,764) 
(40,214) 
83,053 
43,056 
39,997 
26,046 
13,951 

Total
1,397,752 
(1,297,325) 
(46,416) 
54,011 
50,450 
3,561 
11,835 
(8,274) 

Total
1,200,514 
(1,085,040) 
(50,132) 
65,342 
21,291 
44,051 
5,919 
38,132 

The Company conducts its operations primarily in the U.S. with 6.0%, 8.8%, and 7.2% of total revenues generated overseas 
for the years ended December 31, 2023, 2022 and 2021, respectively.

The following table presents the reportable segments, Tiptree Capital - Other and Corporate assets for the following periods:

As of December 31, 2023

Tiptree Capital

As of December 31, 2022

Tiptree Capital

Insurance Mortgage

Other

Corporate

Total

Insurance Mortgage

Other

Corporate

Total

Total assets

$ 4,835,685  $  160,147  $  126,624  $  16,857  $ 5,139,313 

$ 3,702,577  $  156,122  $  86,402  $  94,462  $ 4,039,563 

F-25

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

(6) Investments

The following table presents the Company's investments related to insurance operations and other Tiptree investing activities, 
measured at fair value as of the following periods:

Available for sale securities, at fair value, net of allowance for 
credit losses
Loans, at fair value
Equity securities
Other investments
Total investments

Available for sale securities, at fair value, net of allowance for 
credit losses
Loans, at fair value
Equity securities
Other investments
Total investments

Available for Sale Securities, at fair value

As of December 31, 2023
Tiptree Capital

Insurance

Mortgage

Other

Total

772,135  $ 
11,218 
27,113 
106,760 
917,226  $ 

—  $ 

58,338 
— 
3,931 
62,269  $ 

30,474  $ 
— 
41,195 
397 
72,066  $ 

802,609 
69,556 
68,308 
111,088 
1,051,561 

As of December 31, 2022
Tiptree Capital

Insurance

Mortgage

Other

Total

611,980  $ 
14,312 
72,992 
66,163 
765,447  $ 

—  $ 

50,531 
— 
4,038 
54,569  $ 

—  $ 
— 
12,784 
2,824 
15,608  $ 

611,980 
64,843 
85,776 
73,025 
835,624 

$ 

$ 

$ 

$ 

A  majority  of  the  Company’s  investments  in  Available  for  Sale  Securities,  at  fair  value,  net  of  allowance  for  credit  losses 
(AFS securities) as of December 31, 2023 and 2022 are held by subsidiaries in the insurance segment. The following tables 
present the Company's investments in AFS securities:

Amortized 
cost

Allowance for 
credit losses(1)

As of December 31, 2023
Gross
unrealized 
gains

Gross
unrealized 
losses

Fair value

U.S.  Treasury  securities  and  obligations  of  U.S. 
government authorities and agencies
Obligations of state and political subdivisions
Corporate securities
Asset backed securities
Certificates of deposit
Obligations of foreign governments

Total

$ 

$ 

496,731  $ 
48,762 
260,961 
29,275 
1,724 
4,705 
842,158  $ 

—  $ 
(1) 
(73) 
(10) 
— 
— 
(84)  $ 

515  $ 
51 
2,445 
3 
— 
— 
3,014  $ 

(27,161)  $ 
(3,353) 
(8,735) 
(3,082) 
— 
(148) 
(42,479)  $ 

470,085 
45,459 
254,598 
26,186 
1,724 
4,557 
802,609 

Amortized 
cost

Allowance for 
credit losses(1)

As of December 31, 2022
Gross
unrealized 
gains

Gross
unrealized 
losses

Fair value

U.S.  Treasury  securities  and  obligations  of  U.S. 
government authorities and agencies
Obligations of state and political subdivisions
Corporate securities
Asset backed securities
Certificates of deposit
Obligations of foreign governments

Total

$ 

$ 

417,278  $ 
54,390 
176,187 
19,596 
756 
2,629 
670,836  $ 

—  $ 
(3) 
(183) 
(1) 
— 
(3) 
(190)  $ 

844  $ 
4 
1 
— 
— 
— 
849  $ 

(36,062)  $ 
(4,937) 
(14,006) 
(4,246) 
— 
(264) 
(59,515)  $ 

382,060 
49,454 
161,999 
15,349 
756 
2,362 
611,980 

F-26

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

(1) Represents the amount of impairment that has resulted from credit-related factors, and therefore was recognized in net realized and unrealized gains (losses) as a credit loss on 
AFS securities. Amount excludes unrealized losses relating to non-credit factors.

The  amortized  cost  and  fair  values  of  AFS  securities,  by  contractual  maturity  date,  are  shown  below.  Expected  maturities 
may differ from contractual maturities because borrowers may have the right to call or prepay obligations with or without call 
or prepayment penalties.

Due in one year or less 
Due after one year through five years
Due after five years through ten years
Due after ten years
Asset backed securities

Total

As of

December 31, 2023

December 31, 2022

Amortized 
cost

Fair value

Amortized 
cost

Fair value

$ 

$ 

247,613  $ 
318,763 
46,377 
200,130 
29,275 
842,158  $ 

246,489  $ 
307,423 
39,221 
183,290 
26,186 
802,609  $ 

52,265  $ 
300,767 
54,419 
243,789 
19,596 
670,836  $ 

51,315 
280,965 
49,465 
214,887 
15,348 
611,980 

The following tables present the gross unrealized losses on AFS securities by length of time that individual AFS securities 
have been in a continuous unrealized loss position for less than twelve months, and twelve months or greater and do not have 
an allowance for credit losses:

As of December 31, 2023

Less Than or Equal to One Year
Gross
unrealized 
losses

# of 
Securities(1)

Fair value

More Than One Year
Gross 
unrealized 
losses

# of 
Securities(1)

Fair value

U.S. Treasury securities and obligations of U.S. 

government authorities and agencies

Obligations of state and political subdivisions
Corporate securities
Asset backed securities
Certificates of deposit
Obligations of foreign governments

Total

$  109,011  $ 

537 
83,747 
2,187 
— 
2,904 
$  198,386  $ 

(6,522) 
(53) 
(4,881) 
(259) 
— 
— 
(11,715) 

459  $  185,950  $ 
43 
868 
54 
— 
3 

39,319 
57,679 
23,999 
— 
1,653 

1,427  $  308,600  $ 

(20,639) 
(3,300) 
(3,854) 
(2,823) 
— 
(148) 
(30,764) 

480 
131 
148 
129 
— 
7 
895 

As of December 31, 2022

Less Than or Equal to One Year
Gross
unrealized 
losses

# of 
Securities(1)

Fair value

More Than One Year
Gross 
unrealized 
losses

# of 
Securities(1)

Fair value

U.S. Treasury securities and obligations of U.S. 

government authorities and agencies

Obligations of state and political subdivisions
Corporate securities
Asset backed securities
Obligations of foreign governments

Total

$  164,593  $ 
25,507 
45,016 
10,298 
309 

$  245,723  $ 

(9,357) 
(1,076) 
(1,446) 
(3,642) 
(1) 
(15,522) 

354  $  186,591  $ 
97 
176 
46 
1 

20,219 
114,683 
5,051 
2,054 

674  $  328,598  $ 

(26,705) 
(3,861) 
(12,560) 
(604) 
(263) 
(43,993) 

385 
78 
417 
34 
8 
922 

(1) 

Presented in whole numbers.

Management believes that it is more likely than not that the Company will be able to hold the fixed maturity AFS securities 
that were in an unrealized loss position as of December 31, 2023 until full recovery of their amortized cost basis.

F-27

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

The  table  below  presents  a  roll-forward  of  the  activity  in  the  allowance  for  credit  losses  on  AFS  securities  by  type  as  of 
December 31, 2023:

Balance at December 31, 2021
(Increase) in allowance for credit losses
Gains from recoveries of amounts previously written off
Balance at December 31, 2022
(Increase) in allowance for credit losses
Additions for AFS securities purchased with credit 
deterioration during the year
Reduction in credit losses due to AFS securities sold 
during the year
Gains from recoveries of amounts previously written off
Balance at December 31, 2023

$ 

$ 

Obligations 
of state and 
political 
subdivisions
$ 

Corporate 
securities

Asset 
backed 
securities

Obligations 
of foreign 
governments

Total

—  $ 
(3) 
— 
(3)  $ 
— 

(241)  $ 
(69) 
127 
(183)  $ 
(33) 

—  $ 
(1) 
— 
(1)  $ 
(10) 

(4)  $ 
(1) 
2 
(3)  $ 
— 

— 

(2) 

— 

— 

— 
2 
(1)  $ 

1 
144 
(73)  $ 

— 
1 
(10)  $ 

— 
3 
—  $ 

(245) 
(74) 
129 
(190) 
(43) 

(2) 

1 
150 
(84) 

The  Company  applies  a  discounted  cash  flow  model,  based  on  assumptions  and  model  outputs  provided  by  an  investment 
management  company,  in  determining  its  lifetime  expected  credit  losses  on  AFS  securities.  This  includes  determining  the 
present value of expected future cash flows discounted at the book yield of the security.

The table below presents the amount of gains from recoveries (credit losses) on AFS securities recorded by the Company for 
the following period:

For the Year Ended December 31,
2022

2021

2023

Net gains from recoveries (credit losses) on AFS securities

106 

55 

(245) 

Pursuant to certain reinsurance agreements and statutory licensing requirements, the Company has deposited invested assets 
in custody accounts or insurance department safekeeping accounts. The Company cannot remove or replace investments in 
regulatory  deposit  accounts  without  prior  approval  of  the  contractual  party  or  regulatory  authority,  as  applicable.  The 
following table presents the Company's restricted investments included in the Company's AFS securities:

Fair value of restricted investments in trust pursuant to reinsurance agreements
Fair value of restricted investments for special deposits required by state insurance departments

Total fair value of restricted investments

The following table presents additional information on the Company’s AFS securities:

As of December 31,
2022
2023

$ 

$ 

49,735  $ 
16,694 
66,429  $ 

34,386 
16,816 
51,202 

For the Year Ended December 31,
2022

2021

2023

Purchases of AFS securities

Proceeds from maturities, calls and prepayments of AFS securities

Gross proceeds from sales of AFS securities

$ 

$ 

$ 

622,045  $ 

233,541  $ 

368,913 

370,586  $ 

77,703  $ 

68,923 

89,906  $ 

63,066  $ 

86,981 

The following table presents the gross realized gains and gross realized losses from sales and redemptions of AFS securities: 

F-28

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

For the Year Ended December 31,
2022

2021

2023

Gross realized gains
Gross realized (losses)

Total net realized gains (losses) from investment sales and redemptions

$ 

$ 

225  $ 

(3,056) 
(2,831)  $ 

1,543  $ 
(184)   
1,359  $ 

661 
(23) 
638 

Loans, at fair value

The following table presents the Company’s investments in loans measured at fair value and the Company’s investments in 
loans measured at fair value pledged as collateral:

As of December 31, 2023

As of December 31, 2022

Unpaid 
principal 
balance 
(UPB)

Fair 
value 
exceeds / 
(below) 
UPB

Fair 
value

Pledged 
as 
collateral

Fair 
value

Unpaid 
principal 
balance 
(UPB)

Fair 
value 
exceeds / 
(below) 
UPB

Pledged 
as 
collateral

$  11,218  $  14,671  $ 

(3,453)  $ 

—  $  14,312  $  16,032  $ 

(1,720)  $ 

— 

Insurance:

Corporate loans (1)

Mortgage:

Mortgage loans held for sale (2)
Total loans, at fair value

  58,338 
$  69,556  $  71,152  $ 

56,481 

1,857 
(1,596)  $  57,248  $  64,843  $  65,393  $ 

  50,531 

57,248 

49,361 

1,170 
50,113 
(550)  $  50,113 

(1) 

(2) 

The cost basis of Corporate loans was approximately $14,671 and $16,032 at December 31, 2023 and 2022, respectively. 
As of December 31, 2023, there were three mortgage loans held for sale that were 90 days or more past due. As of December 31, 2022, there were no mortgage loans held 
for sale that were 90 days or more past due.

Equity Securities

Equity securities consist mainly of publicly traded common and preferred stocks and fixed income exchange traded funds. 
Included within the equity securities balance are 16.98 million shares of Invesque as of December 31, 2023 and 2022, for 
which the Company has elected to apply the fair value option. The following table presents information on the cost and fair 
value of the Company’s equity securities related to Insurance and Tiptree Capital as of the following periods:

As of December 31, 2023
Tiptree Capital - Other

Total

Fair Value

Fair Value

Cost
111,490  $ 
— 
29,942 
141,432  $ 

3,442  $ 
— 
37,753 
41,195  $ 

Cost
134,829  $ 
1,339 
52,683 
188,851  $ 

4,161 
1,349 
62,798 
68,308 

As of December 31, 2022
Tiptree Capital - Other

Total

Fair Value

Fair Value

Cost
111,491  $ 
— 
— 
111,491  $ 

12,784  $ 
— 
— 
12,784  $ 

Cost
134,830  $ 
56,263 
15,773 
206,866  $ 

15,454 
56,256 
14,066 
85,776 

Invesque
Fixed income exchange traded funds
Other equity securities

Total equity securities

Invesque
Fixed income exchange traded funds
Other equity securities

Total equity securities

Insurance

Cost

Fair Value

23,339  $ 
1,339 
22,741 
47,419  $ 

719  $ 

1,349 
25,045 
27,113  $ 

Insurance

Cost

Fair Value

23,339  $ 
56,263 
15,773 
95,375  $ 

2,670  $ 
56,256 
14,066 
72,992  $ 

$ 

$ 

$ 

$ 

F-29

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Other Investments

The following table contains information regarding the Company’s other investments as of the following periods:

Corporate bonds, at fair value (1)
Debentures
Investment in credit fund
Other

Total other investments

Corporate bonds, at fair value (1)
Debentures
Other

Total other investments

As of December 31, 2023
Tiptree Capital

Insurance

Mortgage

Other

Total

62,081  $ 
25,648 
11,830 
7,201 
106,760  $ 

—  $ 
— 
— 
3,931 
3,931  $ 

—  $ 
— 
— 
397 
397  $ 

62,081 
25,648 
11,830 
11,529 
111,088 

As of December 31, 2022
Tiptree Capital

Insurance

Mortgage

Other

Total

42,080  $ 
23,853 
230 
66,163  $ 

—  $ 
— 
4,038 
4,038  $ 

—  $ 
— 
2,824 
2,824  $ 

42,080 
23,853 
7,092 
73,025 

$ 

$ 

$ 

$ 

(1) 

The cost basis of corporate bonds was $59,315 and $45,630 as of December 31, 2023 and 2022, respectively.

Net Investment Income - Insurance

Net  investment  income  represents  investment  income  and  expense  from  investments  related  to  insurance  operations  as 
disclosed  within  net  investment  income  on  the  consolidated  statements  of  operations.  The  following  table  presents  the 
components of net investment income by source of income:

For the Year Ended December 31,
2022

2021

2023

Interest:

AFS securities
Loans, at fair value
Other investments

Dividends from equity securities

Subtotal

Less: investment expenses

Net investment income

Other Investment Income - Tiptree Capital

$ 

$ 

22,783  $ 
716 
8,311 
1,398 
33,208 
6,534 
26,674  $ 

11,262  $ 
780 
5,346 
1,398 
18,786 
6,567 
12,219  $ 

7,153 
802 
5,792 
7,355 
21,102 
3,206 
17,896 

Other  investment  income  represents  revenue  from  non-insurance  activities  as  disclosed  within  other  revenue  on  the 
consolidated  statements  of  operations,  see  Note  (16)  Other  Revenue  and  Other  Expenses.  The  following  tables  present  the 
components of other investment income by type:

For the Year Ended December 31,
2022

2021

2023

Interest income from Loans, at fair value (1)
Loan fee income (1)
Other

Other investment income

$ 

$ 

3,111  $ 
16,449 
4,703 
24,263  $ 

5,384  $ 
18,132 
30,144 
53,660  $ 

7,184 
21,834 
35,562 
64,580 

(1) 

Includes income related to Loans at fair value classified as Held for Sale for the periods prior to July 1, 2022. 

F-30

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Net Realized and Unrealized Gains (Losses)

The  following  table  presents  the  components  of  net  realized  and  unrealized  gains  (losses)  recorded  on  the  consolidated 
statements  of  operations.  Net  unrealized  gains  (losses)  on  AFS  securities  are  included  within  other  comprehensive  income 
(loss)  (“OCI”),  net  of  tax,  and,  as  such,  are  not  included  in  this  table.  Net  realized  and  unrealized  gains  (losses)  on  non-
investment related financial assets and liabilities are included below:

For the Year Ended December 31,
2022

2021

2023

Net realized gains (losses)
Insurance:

Reclass of unrealized gains (losses) on AFS securities from OCI 
Net gains from recoveries (credit losses) on AFS securities
Net realized gains (losses) on loans 
Net realized gains (losses) on equity securities 
Net realized gains (losses) on corporate bonds
Other 
Tiptree Capital
Mortgage:
Net realized gains (losses) on loans
Other
Other:
Net realized gains (losses) on loans (1)
Net realized gains on vessel sales
Other 

Total net realized gains (losses)

Net unrealized gains (losses)
Insurance:

Net change in unrealized gains (losses) on loans 
Net unrealized gains (losses) on equity securities held at period end
Reclass of unrealized (gains) losses from prior periods for equity securities sold 
Other 
Tiptree Capital
Mortgage:
Net change in unrealized gains (losses) on loans
Other
Other:
Net change in unrealized gains (losses) on loans (1)
Net unrealized gains (losses) on equity securities held at period end
Other 

Total net unrealized gains (losses)

Total net realized and unrealized gains (losses)

(1) 

Relates to Loans, at fair value classified as Held for Sale for the periods prior to July 1, 2022. 

$ 

$ 

$ 

$ 

(2,830)  $ 
106 
(2,826) 
(2,937) 
(3,065) 
993 

39,288 
1,413 

— 
— 
— 
30,142  $ 

1,359  $ 
55 
(1,505) 
(4,231) 
(3,542) 
(2,432) 

38,608 
16,942 

24,403 
34,803 
761 
105,221 

(1,733)  $ 
923 
357 
6,805 

117 
(6,462) 
(142) 
(3,564) 

687 
(7,156) 

(2,049) 
(2,156) 

— 
(1,531) 
(3,758) 
(5,406) 
24,736  $ 

(4,513) 
(16,015) 
(454) 
(35,238) 
69,983  $ 

638 
(245) 
(389) 
(10,434) 
3,917 
1,346 

91,538 
2,165 

61,312 
— 
1,632 
151,480 

1,330 
12,445 
(814) 
(9,800) 

(1,127) 
(268) 

815 
3,090 
(5,801) 
(130) 
151,350 

F-31

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

(7) Notes and Accounts Receivable, net

The following table presents the total notes and accounts receivable, net:

Accounts and premiums receivable, net
Retrospective commissions receivable
Notes receivable, net
Other receivables

Total notes and accounts receivable, net

As of December 31,

2023

2022

$ 

$ 

260,383  $ 
250,788 
134,131 
39,306 
684,608  $ 

142,011 
191,092 
121,419 
47,789 
502,311 

The following table presents the total valuation allowance and bad debt expense for the following periods:

Valuation allowance
As of December 31,
2022
2023

Bad Debt Expense
For the Year Ended December 31,
2021
2022
2023

Notes receivable, net - premium financing program (1)

Accounts and premiums receivable, net

$ 

$ 

46  $ 

66  $ 

85  $ 

94  $ 

119  $ 

141  $ 

18  $ 

56  $ 

274 

33 

(1) 

As of December 31, 2023 and 2022, there were $219 and $168 in balances classified as 90 days plus past due, respectively.

(8) Reinsurance Recoverable and Prepaid Reinsurance Premiums

The  following  table  presents  the  effect  of  reinsurance  on  premiums  written  and  earned  by  our  insurance  business  for  the 
following periods:

As of December 31, 2023
Life insurance in force

For the Year Ended December 31, 2023
Premiums written:
Life insurance
Accident and health insurance
Property and liability insurance
Total premiums written

Premiums earned:
Life insurance
Accident and health insurance
Property and liability insurance
Total premiums earned

Direct 
Amount

Ceded to 
Other 
Companies

Assumed 
from Other 
Companies

Net Amount

Percentage of 
Amount - 
Assumed to 
Net

$ 

5,909,645 

$ 

2,806,307 

$ 

— 

$ 

3,103,338 

$ 

$ 

$ 

$ 

80,597 
131,006 
1,684,907 
1,896,510 

82,514 
137,868 
1,407,659 
1,628,041 

$ 

$ 

$ 

$ 

40,925 
89,627 
935,077 
1,065,629 

41,248 
94,905 
768,762 
904,915 

$ 

$ 

$ 

$ 

289 
6,176 
482,602 
489,067 

274 
6,215 
398,219 
404,708 

$ 

$ 

$ 

$ 

39,961 
47,555 
1,232,432 
1,319,948 

41,540 
49,178 
1,037,116 
1,127,834 

 0.7 %
 13.0 %
 39.2 %
 37.1 %

 0.7 %
 12.6 %
 38.4 %
 35.9 %

F-32

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Direct 
Amount

Ceded to 
Other 
Companies

Assumed 
from Other 
Companies

Net Amount

Percentage of 
Amount - 
Assumed to 
Net

$ 

6,139,755 

$ 

2,892,889 

$ 

— 

$ 

3,246,866 

 0.4 %
 14.3 %
 37.1 %
 34.4 %

 1.2 %
 14.7 %
 37.3 %
 34.3 %

 1.8 %

 11.3 %

 26.8 %

 24.7 %

 3.4 %

 15.0 %

 33.9 %

 31.0 %

As of December 31, 2022
Life insurance in force

For the Year Ended December 31, 2022
Premiums written:
Life insurance
Accident and health insurance
Property and liability insurance
Total premiums written

Premiums earned:
Life insurance
Accident and health insurance
Property and liability insurance
Total premiums earned

As of December 31, 2021

Life insurance in force

For the Year Ended December 31, 2021

Premiums written:

Life insurance

Accident and health insurance

Property and liability insurance

$ 

$ 

$ 

$ 

88,430 
142,132 
1,284,543 
1,515,105 

82,730 
141,662 
1,090,744 
1,315,136 

$ 

$ 

$ 

$ 

41,218 
96,923 
661,871 
800,012 

41,359 
96,725 
582,711 
720,795 

$ 

$ 

$ 

$ 

193 
7,519 
366,585 
374,297 

522 
7,734 
302,168 
310,424 

$ 

$ 

$ 

$ 

47,405 
52,728 
989,257 
1,089,390 

41,893 
52,671 
810,201 
904,765 

$ 

5,921,446 

$ 

3,068,761 

$ 

— 

$ 

2,852,685 

$ 

91,865 

$ 

46,920 

$ 

808 

$ 

146,256 

1,141,979 

100,717 

558,471 

5,790 

214,150 

45,753 

51,329 

797,658 

Total premiums written

$ 

1,380,100 

$ 

706,108 

$ 

220,748 

$ 

894,740 

Premiums earned:

Life insurance

Accident and health insurance

Property and liability insurance

74,151 

126,501 

902,439 

39,881 

85,457 

504,785 

1,194 

7,219 

204,171 

35,464 

48,263 

601,825 

Total premiums earned

$ 

1,103,091 

$ 

630,123 

$ 

212,584 

$ 

685,552 

The following table presents the components of policy and contract benefits, including the effect of reinsurance on losses and 
loss adjustment expenses (LAE) incurred:

Direct 
Amount

Ceded to 
Other 
Companies

Assumed from 
Other 
Companies

Net Amount

Percentage of 
Amount - 
Assumed to 
Net

F-33

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

For the Year Ended December 31, 2023
Losses and LAE Incurred

Life insurance
Accident and health insurance
Property and liability insurance
Total losses and LAE incurred

For the Year Ended December 31, 2022
Losses and LAE Incurred

Life insurance
Accident and health insurance
Property and liability insurance
Total losses and LAE incurred

For the Year Ended December 31, 2021
Losses and LAE Incurred

Life insurance
Accident and health insurance
Property and liability insurance
Total losses and LAE incurred

$ 

$ 

46,595 
23,694 
647,840 
$ 
718,129 
Member benefit claims (1)
Total policy and contract benefits

25,120 
17,867 
438,953 
481,940 

$ 

$ 

$ 

52,186 
29,221 
447,294 
$ 
528,701 
Member benefit claims (1)
Total policy and contract benefits

28,214 
21,860 
307,052 
357,126 

$ 

$ 

$ 

59,526 
21,509 
354,308 
$ 
435,343 
Member benefit claims (1)
Total policy and contract benefits

34,030 
18,091 
239,678 
291,799 

$ 

$ 

$ 

$ 

$ 

$ 

$ 

122 
5,608 
240,587 
246,317 

504 
6,780 
182,742 
190,026 

869 
2,225 
106,835 
109,929 

(1) Member benefit claims are not covered by reinsurance.

The following table presents the components of the reinsurance recoverable:

Ceded claim reserves:
Life insurance
Accident and health insurance
Property and liability insurance

Total ceded claim reserves recoverable
Other reinsurance settlements recoverable

Total reinsurance recoverable

The following table presents the components of prepaid reinsurance premiums:

Prepaid reinsurance premiums:

Life insurance (1)
Accident and health insurance (1)
Property and liability insurance

Total prepaid reinsurance premiums

(1)

Including policyholder account balances ceded.

$ 

$ 

$ 

$ 

$ 

$ 

$ 

$ 

$ 

$ 

$ 

$ 

$ 

 0.6 %
 49.0 %
 53.5 %
 51.0 %

 2.1 %
 47.9 %
 56.6 %
 52.6 %

 3.3 %
 39.4 %
 48.2 %
 43.4 %

21,597 
11,435 
449,474 
482,506 
119,288 
601,794 

24,476 
14,141 
322,984 
361,601 
91,004 
452,605 

26,365 
5,643 
221,465 
253,473 

73,539 
327,012 

As of December 31,
2022

2023

4,733  $ 
22,660 
420,894 
448,287 
505,599 
953,886  $ 

3,965 
19,408 
243,726 
267,099 
183,521 
450,620 

As of December 31,

2023

2022

74,815  $ 
76,440 
749,269 
900,524  $ 

75,553 
81,718 
568,199 
725,470 

The following table presents the aggregate amount included in reinsurance receivables that is comprised of the three largest 
receivable balances from non-affiliated reinsurers:

Total of the three largest receivable balances from non-affiliated reinsurers

As of
December 31, 2023

$ 

235,672 

F-34

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

As of December 31, 2023, the non-affiliated reinsurers from whom our insurance business has the largest receivable balances 
were:  Accelerant  Specialty  Insurance  Company  (A.M.  Best  Rating:  A-  rated),  Allianz  Global  Corporate  &  Specialty  SE 
(A.M.  Best  Rating:  A+  rated),  and  Homesite  Insurance  Company  (A.M.  Best  Rating:  A  rated).  A  majority  of  the  related 
receivables  from  these  reinsurers  are  collateralized  by  assets  on  hand  and  letters  of  credit;  receivable  balances  from 
authorized  reinsurers  do  not  require  collateral.  Allianz  Global  Corporate  &  Specialty  SE  is  an  authorized  reinsurer  in  the 
states in which Fortegra’s U.S. based insurance entities are domiciled. The Company monitors authorization status, financial 
statements and A.M. Best ratings of its reinsurers periodically. As of December 31, 2023, the Company does not believe there 
is a risk of loss due to the concentration of credit risk in the reinsurance program given the collateralization.

 (9) Goodwill and Intangible Assets, net

The following table presents identifiable finite and indefinite-lived intangible assets, accumulated amortization, and goodwill 
by operating segment and/or reporting unit, as appropriate:

As of December 31, 2023
Other

Total

Insurance

As of December 31, 2022
Other

Total

Insurance

Finite-Lived Intangible Assets:

Customer relationships

Accumulated amortization

Trade names

Accumulated amortization

Software licensing

Accumulated amortization

Insurance policies and contracts acquired

Accumulated amortization

Other

Accumulated amortization

Total finite-lived intangible assets
Indefinite-Lived Intangible Assets: (1)

Insurance licensing agreements
Other

Total indefinite-lived intangible assets

$ 

162,844  $ 
(74,776) 
16,227 
(8,452) 
17,372 
(9,891) 
36,500 
(36,500) 
1,088 
(536) 
103,876 

13,761 
— 
13,761 

Total intangible assets, net

$ 

117,637  $ 

—  $ 
— 
800 
(680) 
640 
(640) 
— 
— 
— 
— 
120 

162,844 
(74,776) 
17,027 
(9,132) 
18,012 
(10,531) 
36,500 
(36,500) 
1,088 
(536) 
103,996 

— 
1,000 
1,000 
1,120  $ 

13,761 
1,000 
14,761 
118,757 

$ 

$ 

$ 

149,835  $ 
(60,401) 
15,028 
(7,039) 
12,386 
(9,084) 
36,500 
(36,374) 
751 
(276) 
101,326 

13,761 
— 
13,761 
115,087  $ 

—  $ 
— 
800 
(600) 
640 
(640) 
— 
— 
— 
— 
200 

149,835 
(60,401) 
15,828 
(7,639) 
13,026 
(9,724) 
36,500 
(36,374) 
751 
(276) 
101,526 

— 
1,728 
1,728 
1,928  $ 

13,761 
1,728 
15,489 
117,015 

184,900 
299,987  $ 

1,708 
3,636  $ 

186,608 
303,623 

Goodwill 

Total goodwill and intangible assets, net $ 

204,447 
322,084  $ 

1,708 
2,828  $ 

206,155 
324,912 

(1) 

Impairment tests are performed at least annually on indefinite-lived intangible assets.

Goodwill

The following table presents the activity in goodwill, by operating segment and/or reporting unit, as appropriate, and includes 
the adjustments made to the balance of goodwill to reflect the effect of the final valuation adjustments made for acquisitions, 
as well as the reduction to any goodwill attributable to impairment related charges:

Balance at December 31, 2021

Goodwill acquired (1)

Foreign currency translation and other
Balance at December 31, 2022

Goodwill acquired (1)
Foreign currency translation and other

Balance at December 31, 2023

(1) 

See Note (3) Acquisitions for more information.

Insurance

Other

Total

$ 

$ 

$ 

177,395  $ 
8,112 
(607) 
184,900  $ 
18,359 
1,188 
204,447  $ 

1,708  $ 
— 
— 
1,708  $ 
— 
— 
1,708  $ 

179,103 
8,112 
(607) 
186,608 
18,359 
1,188 
206,155 

The  Company  conducts  annual  impairment  tests  of  its  goodwill  as  of  October  1.  For  the  years  ended  December  31,  2023, 
2022 and 2021, no impairments were recorded on the Company’s goodwill. There is no accumulated impairment recorded in 
the goodwill balance as of December 31, 2023 or 2022.

F-35

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Intangible Assets, net

The following table presents the activity, by operating segment and/or reporting unit, as appropriate, in finite and indefinite-
lived  other  intangible  assets  and  includes  the  adjustments  made  to  the  balance  to  reflect  the  effect  of  any  final  valuation 
adjustments made for acquisitions, as well as any reduction attributable to impairment-related charges:

Balance at December 31, 2021
Intangible assets acquired (1)
Amortization expense
Foreign currency translation and other

Balance at December 31, 2022
Intangible assets acquired (1)
Amortization expense (2)
Foreign currency translation and other
Impairment

Balance at December 31, 2023

Insurance

Other

Total

$ 

$ 

$ 

121,308  $ 
10,964 
(16,229) 
(956) 
115,087  $ 
18,152 
(16,921) 
1,319 
— 
117,637  $ 

1,450  $ 
604 
(126) 
— 
1,928  $ 
— 
(80) 
— 
(728) 
1,120  $ 

122,758 
11,568 
(16,355) 
(956) 
117,015 
18,152 
(17,001) 
1,319 
(728) 
118,757 

(1) See Note (3) Acquisitions for more information.
(2) Does not include foreign currency translation adjustment of $60 as of December 31, 2023.

The following table presents the amortization expense on finite-lived intangible assets for the following periods:

For the Year Ended December 31,
2022

2021

2023

Amortization expense on intangible assets

$ 

17,001  $ 

16,355  $ 

15,581 

For the year ended December 31, 2023, the Company partially impaired its other indefinite lived intangible assets as a result 
of oversupply of fishing licenses which has driven valuations lower. For the years ended December 31, 2022 and 2021, no 
impairments were recorded on the Company’s intangible assets.

The following table presents the amortization expense on finite-lived intangible assets for the next five years and thereafter 
by operating segment and/or reporting unit, as appropriate:

2024
2025
2026
2027
2028
2029 and thereafter

Total (1)

As of December 31, 2023
Other

Insurance

Total

$ 

$ 

15,354  $ 
13,240 
10,894 
9,543 
8,341 
46,101 
103,473  $ 

80  $ 
40 
— 
— 
— 
— 
120  $ 

15,434 
13,280 
10,894 
9,543 
8,341 
46,101 
103,593 

(1) 

Does not include foreign currency translation adjustment of $403 as of December 31, 2023.

(10) Derivative Financial Instruments and Hedging

The  Company  utilizes  derivative  financial  instruments  as  part  of  its  overall  investment  and  hedging  activities.  Derivative 
contracts  are  subject  to  additional  risk  that  can  result  in  a  loss  of  all  or  part  of  an  investment.  The  Company’s  derivative 
activities  are  primarily  entered  into  in  order  to  manage  underlying  credit  risk,  market  risk,  interest  rate  risk  and  currency 
exchange  rate  risk.  In  addition,  the  Company  is  also  subject  to  counterparty  risk  should  its  counterparties  fail  to  meet  the 
contract terms. Derivative assets are reported in other investments. Derivative liabilities are reported within other liabilities 
and accrued expenses.

Interest Rate Lock Commitments

F-36

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Derivatives for our mortgage business are primarily comprised of interest rate lock commitments (IRLCs), forward delivery 
contracts, and TBA mortgage-backed securities. The fair value of these instruments is based upon valuation pricing models, 
which represent the amount the Company would expect to receive or pay at the balance sheet date to exit the position. Our 
mortgage origination subsidiary issues IRLCs to their customers, which are carried at estimated fair value on the Company’s 
consolidated  balance  sheets.  The  estimated  fair  values  of  these  commitments  are  generally  calculated  by  reference  to  the 
value of the underlying loan associated with the IRLC net of costs to produce and an expected pull through assumption. The 
fair values of these commitments generally fall under Level 3 in the fair value hierarchy. 

Forward Delivery Contracts and TBA Mortgage-Backed Securities

Our  mortgage  origination  subsidiary  manages  their  exposure  by  entering  into  forward  delivery  commitments  with  loan 
investors.  For  loans  not  locked  with  investors  under  a  forward  delivery  commitment,  the  Company  enters  into  hedge 
instruments,  primarily  TBAs,  to  protect  against  movements  in  interest  rates.  The  fair  values  of  TBA  mortgage-backed 
securities and forward delivery contracts generally fall under Level 2 in the fair value hierarchy.

The  remaining  derivatives  are  generally  comprised  of  a  combination  of  swaps,  currency  forwards  and  options,  which  are 
generally  classified  as  Level  2  in  the  fair  value  hierarchy.  In  addition,  the  Fortegra  Additional  Warrant  (Warburg)  is  a 
derivative  liability  and  classified  as  Level  3  in  the  fair  value  hierarchy.  See  Note  (17)  Stockholders'  Equity  for  additional 
information regarding the Fortegra Additional Warrant.

The  following  table  presents  the  gross  notional  and  fair  value  amounts  of  derivatives  (on  a  gross  basis)  categorized  by 
underlying risk:

As of December 31, 2023

As of December 31, 2022

Notional
values

Asset 
derivatives

Liability
derivatives

Notional
values

Asset 
derivatives

Liability
derivatives

Interest rate lock commitments
Forward delivery contracts
TBA mortgage-backed securities
Fortegra Additional Warrants 
(Warburg)(1)
Other

Total

$ 

$ 

129,675  $ 
19,675 
139,000 

— 
24,346 
312,696  $ 

3,818  $ 
9 
104 

— 
52 
3,983  $ 

—  $ 
98 
815 

147,963  $ 
32,160 
133,500 

3,522 
68 
4,503  $ 

— 
13,427 
327,050  $ 

3,652  $ 
112 
273 

— 
230 
4,267  $ 

— 
39 
141 

5,291 
7,730 
13,201 

(1) See Note (17) Stockholders' Equity for additional information.

F-37

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

(11) Debt, net

The following table presents the balance of the Company’s debt obligations, net of discounts and deferred financing costs for 
our corporate and asset based debt. Asset based debt is generally recourse only to specific assets and related cash flows. 

Corporate debt

Secured revolving credit agreements (1)
Preferred trust securities (LIBOR + 4.10%)
8.50% Junior subordinated notes 
Total corporate debt

Asset based debt

Asset based revolving financing (SOFR + 2.75%)
Residential mortgage warehouse borrowings (1.75% to 2.75% over SOFR) (2)(3)
Total asset based debt

Total debt, face value

Unamortized deferred financing costs

Total debt, net

Corporate debt

Secured revolving credit agreements (1)
Preferred trust securities (LIBOR + 4.10%)
8.50% Junior subordinated notes 
Total corporate debt

Asset based debt

Asset based revolving financing (LIBOR + 2.75%)
Residential mortgage warehouse borrowings (1.88% to 2.50% over SOFR; 2.00% 
to 3.00% over BSBY) (2)(3)
Total asset based debt

Total debt, face value

Unamortized deferred financing costs

Total debt, net

As of December 31, 2023
Mortgage

Insurance

Total

130,000  $ 
35,000 
125,000 
290,000 

67,138 
— 
67,138 
357,138 
(8,950) 
348,188  $ 

—  $ 
— 
— 
— 

130,000 
35,000 
125,000 
290,000 

— 
54,350 
54,350 
54,350 
(127) 
54,223  $ 

67,138 
54,350 
121,488 
411,488 
(9,077) 
402,411 

As of December 31, 2022
Mortgage

Insurance

Total

—  $ 

35,000 
125,000 
160,000 

—  $ 
— 
— 
— 

— 
35,000 
125,000 
160,000 

60,628 

— 

60,628 

— 
60,628 
220,628 
(8,703) 
211,925  $ 

47,454 
47,454 
47,454 
(13) 
47,441  $ 

47,454 
108,082 
268,082 
(8,716) 
259,366 

$ 

$ 

$ 

$ 

(1) 

(2) 

(3) 

The secured credit agreements include separate tranches with multiple rate structures that are adjustable based on Fortegra’s senior leverage ratio, which as of December 31, 
2023 and 2022 was SOFR + 1.50%.
As of December 31, 2023, included (i) a $50,000 line of credit at 1.75%, 2.00% and 2.50% over the one month SOFR rate, and (ii) a $65,000 line of credit at 1.75%, 2.25% 
and  2.75%  over  the  one  month  SOFR  rate,  with  a  floor  of  4.00%.  The  balance  credit  rate  on  the  $50,000  line  of  credit  was  25  basis  points  lower  than  the  floor.  As  of 
December 31, 2022, included (i) a $60,000 line of credit at 2.00%, 2.50% and 3.00% over the BSBY rate with a BSBY floor of 0.5% and (ii) a $50,000 line of credit at 
1.875%, 2.00% and 2.50% over the one month SOFR rate. The balance credit rate on the $50,000 line of credit was 25 basis points lower than the floor. 
The weighted average coupon rate for residential mortgage warehouse borrowings was 7.15% and 6.31% at December 31, 2023 and 2022, respectively.

The following table presents the amount of interest expense the Company incurred on its debt for the following periods:

For the Year Ended December 31,
2022

2021

2023

Total Interest expense - corporate debt
Total Interest expense - asset based debt

Interest expense on debt

$ 

$ 

19,531  $ 
8,161 
27,692  $ 

19,290  $ 
10,950 
30,240  $ 

24,425 
13,018 
37,443 

F-38

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

The following table presents the contractual principal payments and future maturities of the unpaid principal balance on the 
Company’s debt for the following periods: 

2024
2025
2026
2027
2028
2029 and thereafter

Total

As of 
December 31, 2023
54,350 
$ 
— 
67,138 
130,000 
— 
160,000 
411,488 

$ 

The following narrative is a summary of certain terms of our debt agreements for the year ended December 31, 2023:

Corporate Debt

Secured Revolving Credit Agreements

As of December 31, 2023 and 2022, a total of $130,000 and $0, respectively, was outstanding under the revolving line of 
credit in our insurance business. The maximum borrowing capacity under the agreements as of December 31, 2023 and 2022 
was $200,000.

On October 21, 2022, a subsidiary of Fortegra entered into a Second Amended and Restated Credit Agreement by and among 
Fortegra,  and  its  subsidiary,  LOTS  Intermediate  Co.,  as  borrowers,  the  lenders  from  time  to  time  party  thereto,  certain  of 
Fortegra’s  subsidiaries,  as  guarantors,  and  Fifth  Third  Bank,  National  Association,  as  the  administrative  agent  and  issuing 
lender (the “Fortegra Credit Agreement”). The Fortegra Credit Agreement provides for a $200,000 revolving credit facility, 
all  of  which  is  available  for  the  issuance  of  letters  of  credit,  with  a  sub-limit  of  $25,000  for  swing  loans  and  matures  on 
October 1, 2027.

Junior Subordinated Notes

On October 16, 2017, a subsidiary of Fortegra issued $125,000 of 8.50% Fixed Rate Resetting Junior Subordinated Notes due 
October  2057.  Substantially  all  of  the  net  proceeds  were  used  to  repay  the  existing  secured  credit  agreement  at  that  time, 
which was terminated thereafter. The notes are unsecured obligations of the subsidiary and rank in right of payment and upon 
liquidation, junior to all of the Fortegra subsidiary’s current and future senior indebtedness. The notes are not obligations of 
or guaranteed by any other subsidiaries of Fortegra, or any other Tiptree entities. So long as no event of default has occurred 
and is continuing, all or part of the interest payments on the notes can be deferred on one or more occasions for up to five 
consecutive years per deferral period. This credit agreement contains customary financial covenants that require, among other 
items, maximum leverage and limitations on restricted payments under certain circumstances.

Preferred Trust Securities

On June 20, 2007, a subsidiary of Fortegra issued $35,000 of preferred trust securities due June 15, 2037. Interest is payable 
quarterly at an interest rate of LIBOR plus 4.10%. The Company may redeem the preferred trust securities, in whole or in 
part, at a price equal to the full outstanding principal amount of such preferred trust securities outstanding plus accrued and 
unpaid interest.

F-39

 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Asset Based Debt

Asset Based Revolving Financing

On October 16, 2020, subsidiaries of Fortegra entered into a three year $75,000 secured credit agreement, which replaced the 
individual  agreements  in  its  premium  finance  and  warranty  service  contract  finance  businesses.  The  borrowers  can  select 
from various borrowing and rate options under the agreement, as well the option to convert certain borrowings to term loans, 
if no default or event of default exists. The agreement extends up to $20,000 for the Company’s premium finance business 
and up to $55,000 for its warranty service contract finance business, and is secured by substantially all of the assets of the 
borrowers  thereunder.  The  obligations  under  the  agreement  are  non-recourse  to  The  Fortegra  Group  and  its  subsidiaries 
(other  than  the  borrowers  and  their  subsidiaries).  On  January  31,  2023,  subsidiaries  of  Fortegra  amended  the  asset  based 
revolving financing to increase the revolving commitment to $100,000 and transition to SOFR. 

On October 6, 2023, subsidiaries of Fortegra entered into a three-year $125 million secured credit agreement that amends and 
restates the prior credit agreement dated October 16, 2020. The agreement extends the maturity date of the revolving credit 
facility  from  October  2023  to  October  2026  and  increases  the  total  revolving  credit  commitments  from  $100  million  to 
$125 million. 

As  of  December  31,  2023  and  2022,  a  total  of  $67,138  and  $60,628,  respectively,  was  outstanding  under  the  borrowing 
related to our premium finance offerings in our insurance business. 

Residential Mortgage Warehouse Borrowings

In January 2023, a $60,000 warehouse line of credit was renewed and the maturity date was extended from January 2023 to 
January  2024.  In  June  2023,  the  Company  received  notification  that  the  warehouse  lending  partners  was  exiting  the 
warehouse lending market for this renewed line.  In October 2023, the line was terminated and paid in full as the provider 
exited the warehouse lending market. The Company entered into a new $65,000 warehouse line of credit on September 20, 
2023 with similar terms with a maturity date of August 2024.

As  of  December  31,  2023  and  2022,  a  total  of  $54,350  and  $47,454,  respectively,  was  outstanding  under  such  financing 
agreements.

Vessel-Backed Term Loan

The remaining balance of the vessel backed term loan totaling $13,050 was fully repaid at a discount during May 2022, for a 
net gain of $1,168 during the year ended 2022.

(12) Fair Value of Financial Instruments

The Company maximizes the use of observable inputs and minimizes the use of unobservable inputs to the extent possible to 
measure  a  financial  instrument’s  fair  value.  Observable  inputs  reflect  the  assumptions  market  participants  would  use  in 
pricing an asset or liability, and are affected by the type of product, whether the product is traded on an active exchange or in 
the secondary market, as well as current market conditions. To the extent that valuation is based on models or inputs that are 
less observable or unobservable in the market, the determination of fair value requires more judgment. In certain cases, the 
inputs  used  to  measure  fair  value  may  fall  into  different  levels  of  the  fair  value  hierarchy.  In  such  cases,  for  disclosure 
purposes, the level in the fair value hierarchy within which the fair value measurement in its entirety falls is determined based 
on the lowest level input that is significant to the fair value measurement in its entirety. Fair value is estimated by applying 
the hierarchy discussed in Note (2) Summary of Significant Accounting Policies which prioritizes the inputs used to measure 
fair value into three levels and bases the categorization within the hierarchy upon the lowest level of input that is available 
and significant to the fair value measurement. Accordingly, the degree of judgment exercised by the Company in determining 
fair value is greatest for instruments categorized within Level 3 of the fair value hierarchy.

The Company’s fair value measurements are based primarily on a market approach, which utilizes prices and other relevant 
information generated by market transactions involving identical or comparable financial instruments. Sources of inputs to 

F-40

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

the market approach include third-party pricing services, independent broker quotations and pricing matrices. Management 
analyzes the third-party valuation methodologies and its related inputs to perform assessments to determine the appropriate 
level within the fair value hierarchy and to assess reliability of values. Further, management has a process in place to review 
all  changes  in  fair  value  that  occurred  during  each  measurement  period.  Any  discrepancies  or  unusual  observations  are 
followed through to resolution through the source of the pricing as well as utilizing comparisons, if applicable, to alternate 
pricing sources.

The  Company  utilizes  observable  and  unobservable  inputs  within  its  valuation  methodologies.  Observable  inputs  may 
include:  benchmark  yields,  reported  trades,  broker-dealer  quotes,  issuer  spreads,  benchmark  securities,  bids,  offers  and 
reference data. In addition, specific issuer information and other market data is used. Broker quotes are obtained from sources 
recognized to be market participants. Unobservable inputs may include: expected cash flow streams, default rates, supply and 
demand considerations and market volatility. 

Available for Sale Securities, at fair value

The fair values of AFS securities are based on prices provided by an independent pricing service and a third-party investment 
manager. The Company obtains an understanding of the methods, models and inputs used by the independent pricing service 
and the third-party investment manager by analyzing the investment manager-provided pricing report.

The following details the methods and assumptions used to estimate the fair value of each class of AFS securities and the 
applicable level each security falls within the fair value hierarchy:

U.S.  Treasury  Securities,  Obligations  of  U.S.  Government  Authorities  and  Agencies,  Obligations  of  State  and  Political 
Subdivisions,  Corporate  Securities,  Asset  Backed  Securities,  and  Obligations  of  Foreign  Governments:  Fair  values  were 
obtained from an independent pricing service and a third-party investment manager. The prices provided by the independent 
pricing service and third-party investment manager are based on quoted market prices, when available, non-binding broker 
quotes, or matrix pricing and fall under Level 2 or Level 3 in the fair value hierarchy. 

Certificates of Deposit: The estimated fair value of certificates of deposit approximate carrying value and fall under Level 1 
of the fair value hierarchy.

Equity Securities

The fair values of publicly traded common and preferred equity securities and exchange traded funds (“ETFs”) are obtained 
from market value quotations provided by an independent pricing service and fall under Level 1 in the fair value hierarchy. 
The  fair  values  of  non-publicly  traded  common  and  preferred  stocks  are  based  on  prices  derived  from  multiples  of 
comparable public companies and fall under Level 3 in the fair value hierarchy. 

Loans, at fair value

Corporate Loans: These loans are comprised of middle market loans and bank loans and are generally classified under either 
Level  2  or  Level  3  in  the  fair  value  hierarchy.  To  determine  fair  value,  the  Company  uses  quoted  prices,  including  those 
provided  from  pricing  vendors,  which  provide  coverage  of  secondary  market  participants,  where  available.  The  values 
represent  a  composite  of  mark-to-market  bid/offer  prices.  In  certain  circumstances,  the  Company  will  make  its  own 
determination of fair value of loans based on internal models and other unobservable inputs.

Mortgage Loans Held for Sale: Mortgage loans held for sale are generally classified under Level 2 in the fair value hierarchy 
and fair value is based upon forward sales contracts with third-party investors, including estimated loan costs. 

Derivative Assets and Liabilities

Derivatives  for  our  mortgage  business  are  primarily  comprised  of  IRLCs,  forward  delivery  contracts  and  TBA  mortgage-
backed securities. The fair value of these instruments is based upon valuation pricing models, which represent the amount the 
Company would expect to receive or pay at the balance sheet date to exit the position. Our mortgage origination subsidiaries 
issue IRLCs to their customers, which are carried at estimated fair value on the Company’s consolidated balance sheets. The 
estimated  fair  values  of  these  commitments  are  generally  calculated  by  reference  to  the  value  of  the  underlying  loan 

F-41

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

associated  with  the  IRLC  net  of  costs  to  produce  and  an  expected  pull  through  assumption.  The  fair  values  of  these 
commitments  generally  fall  under  Level  3  in  the  fair  value  hierarchy.  Our  mortgage  origination  subsidiaries  manage  their 
exposure  by  entering  into  forward  delivery  commitments  with  loan  investors.  For  loans  not  locked  with  investors  under  a 
forward delivery commitment, the Company enters into hedge instruments, primarily TBAs, to protect against movements in 
interest rates. The fair values of TBA mortgage-backed securities and forward delivery contracts generally fall under Level 2 
in the fair value hierarchy. 

The  remaining  derivatives  are  generally  comprised  of  a  combination  of  swaps,  currency  forwards  and  options,  which  are 
generally  classified  as  Level  2  in  the  fair  value  hierarchy.  In  addition,  the  Fortegra  Additional  Warrants  (Warburg)  are  a 
derivative  liability  and  classified  as  Level  3  in  the  fair  value  hierarchy.  See  Note  (17)  Stockholders'  Equity  for  additional 
information regarding the Fortegra Additional Warrant.

Corporate Bonds

Corporate bonds are generally classified under Level 2 in the fair value hierarchy and fair value is based on quoted market 
prices. We perform internal price verification procedures to ensure that the prices provided are reasonable.

Securities Sold, Not Yet Purchased

Securities sold, not yet purchased are generally classified under Level 1 or Level 2 in the fair value hierarchy, based on the 
leveling of the securities sold short, and fair value is provided by a third-party investment manager, based on quoted market 
prices. We perform internal price verification procedures monthly to ensure that the prices provided are reasonable.

Mortgage Servicing Rights

Mortgage servicing rights are classified under Level 3 in the fair value hierarchy and fair value is provided by a third-party 
valuation service. Various observable and unobservable inputs are used to determine fair value, including discount rate, cost 
to service and weighted average prepayment speed. 

F-42

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

The following tables present the Company’s fair value hierarchies for financial assets and liabilities, measured on a recurring 
basis: 

As of December 31, 2023

Quoted
prices in
active
markets 
Level 1

 Other 
significant
 observable 
inputs 
 Level 2 

 Significant 
unobservable 
inputs
Level 3

Fair value

Assets:
Available for sale securities, at fair value:

U.S. Treasury securities and obligations of U.S. government 
authorities and agencies
Obligations of state and political subdivisions
Obligations of foreign governments
Certificates of deposit
Asset backed securities
Corporate securities
Total available for sale securities, at fair value

$ 

—  $ 
— 
— 
1,724 
— 
— 
1,724 

470,085  $ 
45,459 
4,557 
— 
26,171 
254,598 
800,870 

—  $ 
— 
— 
— 
15 
— 
15 

Loans, at fair value:
Corporate loans
Mortgage loans held for sale
Total loans, at fair value

Equity securities:

Invesque
Fixed income ETFs
Other equity securities

Total equity securities

Other investments, at fair value:

Corporate bonds
Derivative assets
Other
Total other investments, at fair value

Mortgage servicing rights (1)

— 
— 
— 

4,161 
1,349 
55,072 
60,582 

— 
— 
— 
— 

— 

2,051 
58,338 
60,389 

— 
— 
— 
— 

62,081 
162 
18,979 
81,222 

9,167 
— 
9,167 

— 
— 
7,726 
7,726 

— 
3,821 
— 
3,821 

— 

40,836 

40,836 

Total

$ 

62,306  $ 

942,481  $ 

61,565  $ 

1,066,352 

Liabilities: (2)
Derivative liabilities
Fortegra Additional Warrants (Warburg)
Contingent consideration payable

Total

— 
— 
— 
—  $ 

937 
— 
— 
937  $ 

44 
3,522 
2,604 
6,170  $ 

981 
3,522 
2,604 
7,107 

$ 

(1) 

(2) 

Included in other assets. See Note (15) Other Assets and Other Liabilities and Accrued Expenses.
Included in other liabilities and accrued expenses. See Note (15) Other Assets and Other Liabilities and Accrued Expenses.

F-43

470,085 
45,459 
4,557 
1,724 
26,186 
254,598 
802,609 

11,218 
58,338 
69,556 

4,161 
1,349 
62,798 
68,308 

62,081 
3,983 
18,979 
85,043 

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Assets:
Available for sale securities, at fair value:

U.S. Treasury securities and obligations of U.S. government 
authorities and agencies
Obligations of state and political subdivisions
Obligations of foreign governments
Certificates of deposit
Asset backed securities
Corporate securities
Total available for sale securities, at fair value

Loans, at fair value:
Corporate loans
Mortgage loans held for sale
Total loans, at fair value

Equity securities:

Invesque
Fixed income ETFs
Other equity securities

Total equity securities

Other investments, at fair value:

Corporate bonds
Derivative assets
Other
Total other investments, at fair value

Mortgage servicing rights (1)

Total

Liabilities: (2)
Securities sold, not yet purchased
Derivative liabilities
Fortegra Additional Warrants (Warburg)
Contingent consideration payable

Total

$ 

$ 

$ 

$ 

Quoted
prices in
active
markets 
Level 1

As of December 31, 2022
 Other 
significant
 observable 
inputs 
 Level 2 

 Significant 
unobservable 
inputs
Level 3

Fair value

—  $ 
— 
— 
756 
— 
— 
756 

382,060  $ 
49,454 
2,362 
— 
15,254 
161,999 
611,129 

—  $ 
— 
— 
— 
95 
— 
95 

382,060 
49,454 
2,362 
756 
15,349 
161,999 
611,980 

— 
— 
— 

3,104 
50,531 
53,635 

11,208 
— 
11,208 

— 
— 
— 
— 

42,080 
608 
— 
42,688 

— 
— 
6,885 
6,885 

— 
3,652 
324 
3,976 

15,454 
56,256 
7,181 
78,891 

— 
7 
— 
7 

— 

14,312 
50,531 
64,843 

15,454 
56,256 
14,066 
85,776 

42,080 
4,267 
324 
46,671 

— 

41,426 

41,426 

79,654  $ 

707,452  $ 

63,590  $ 

850,696 

10,263  $ 
— 
— 
— 
10,263  $ 

6,312  $ 
7,910 
— 
— 
14,222  $ 

—  $ 
— 
5,291 
2,904 
8,195  $ 

16,575 
7,910 
5,291 
2,904 
32,680 

(1) 

(2) 

Included in other assets. See Note (15) Other Assets and Other Liabilities and Accrued Expenses.
Included in other liabilities and accrued expenses. See Note (15) Other Assets and Other Liabilities and Accrued Expenses.

F-44

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Transfers between Level 2 and 3 were a result of subjecting third-party pricing on assets to various liquidity, depth, bid-ask 
spread and benchmarking criteria as well as assessing the availability of observable inputs affecting their fair valuation. 

The following table presents additional information about assets that are measured at fair value on a recurring basis for which 
the Company has utilized Level 3 inputs to determine fair value for the following periods:

Balance at January 1,

Net realized and unrealized gains or losses included in:

Earnings
OCI

Origination of IRLCs
Purchases
Sales and repayments
Conversions to mortgage loans held for sale
Settlement of trade claims
Exchange of bonds for term loans
Exchange of trade receivables for equity securities
Transfer out of Level 3
Conversions to real estate owned

Balance at December 31, 

Changes in unrealized gains (losses) included in earnings related to assets still held at period end
Changes in unrealized gains (losses) included in OCI related to assets still held at period end

For the Year Ended
December 31, 

2023

2022

$ 

63,590  $ 

61,443 

(4,825)   
2,569 
43,875 
31 
(6)   
(43,709)   

— 
— 
— 
(41)   
81 
61,565  $ 

9,467 
(520) 
52,932 
13 
(3,815) 
(56,794) 
(19,169) 
12,673 
7,360 
— 
— 
63,590 

(4,824)  $ 
2,569  $ 

(3,870) 
(520) 

$ 

$ 
$ 

The following table presents the range and weighted average (WA) used to develop significant unobservable inputs for the 
fair value measurements of Level 3 assets and liabilities:

As of December 31,

2023

2022

Fair value

$ 

3,818  $ 

3,652 

40,836 

41,426 

7,726 

6,837 

9,167 

11,208 

Assets

IRLCs

Mortgage 
servicing 
rights

Equity 
securities

Corporate 
loans

Total

$ 

61,547  $ 

63,123 

Valuation 
technique
Internal 
model

Unobservable 
input(s)

Pull through rate

Discount rate

Cost to service

Prepayment 
speed

Forecast 
EBITDAR

Bid marks/
EBITDA

External 
model

Internal 
model

External/
Internal 
model

As of December 31,

2023

Range

45%

10%

$65

3%

to

to

to

to

95%

13%

$3,000

82%

WA 
(1)

59%

11%

$113

9%

2022

Range

55% to

9%

$65

4%

to

to

to

95%

14%

$80

85%

WA 
(1)

65%

9%

$72

9%

$1,039,000 to $1,422,000 N/A $728,000 to $1,039,000 N/A

$71

to

$75

$73

$170,000

N/A

Liabilities
Fortegra 
Additional 
Warrants 
(Warburg)

Contingent 
consideration 
payable

$ 

3,522  $ 

5,291 

External 
Model

2,604 

2,904 

Cash Flow 
model

Discount rate

Implied Equity 
Volatility

Forecast Cash 
EBITDA

Forecast 
Underwriting 
EBITDA

3%

40%

$2,500

$—

to

to

to

to

5%

3.8%

3%

50%

45%

40%

$4,000

N/A

$2,500

to

to

to

5%

3.3%

50%

45%

$4,000

N/A

$2,000

N/A

$— to

$2,000

N/A

Total

$ 

6,126  $ 

8,195 

F-45

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

(1) 

Unobservable inputs were weighted by the relative fair value of the instruments.

The  following  table  presents  the  carrying  amounts  and  estimated  fair  values  of  financial  assets  and  liabilities  that  are  not 
recorded at fair value and their respective levels within the fair value hierarchy:

As of December 31, 2023

As of December 31, 2022

Level within
fair value
hierarchy

Fair value

Carrying 
value

Level within
fair value
hierarchy

Fair value

Carrying 
value

2
2

3

$ 

$ 

$ 
$ 

25,648  $ 
134,131 
159,779  $ 

25,648 
134,131 
159,779 

406,801  $ 
406,801  $ 

411,488 
411,488 

2
2

3

$ 

$ 

$ 
$ 

23,853  $ 
121,419 
145,272  $ 

23,853 
121,419 
145,272 

262,932  $ 
262,932  $ 

268,082 
268,082 

Assets:

Debentures (1)
Notes receivable, net

Total assets

Liabilities:
Debt

Total liabilities

(1)

Included in other investments. 

Debentures:  Since  interest  rates  on  debentures  are  at  current  market  rates  for  similar  credit  risks,  the  carrying  amount 
approximates fair value. These values are net of allowance for doubtful accounts. 

Notes  Receivable,  net:  To  the  extent  that  carrying  amounts  differ  from  fair  value,  fair  value  is  determined  based  on 
contractual cash flows discounted at market rates for similar credits. Categorized under Level 2 in the fair value hierarchy. 
See Note (7) Notes and Accounts Receivable, net.

Debt: The carrying value, which approximates fair value of floating rate debt, represents the total debt balance at face value 
excluding the unamortized discount. The fair value of the Junior subordinated notes is determined based on dealer quotes. 
Categorized under Level 3 in the fair value hierarchy.

Additionally, the following financial assets and liabilities on the consolidated balance sheets are not carried at fair value, but 
whose carrying amounts approximate their fair value: 

Cash and Cash Equivalents: The carrying amounts of cash and cash equivalents are carried at cost which approximates fair 
value. Categorized under Level 1 in the fair value hierarchy.

Accounts  and  Premiums  Receivable,  net,  Retrospective  Commissions  Receivable  and  Other  Receivables:  The  carrying 
amounts approximate fair value since no interest rate is charged on these short duration assets. Categorized under Level 2 in 
the fair value hierarchy. See Note (7) Notes and Accounts Receivable, net.

Due from Brokers, Dealers, and Trustees and Due to Brokers, Dealers and Trustees: The carrying amounts are included in 
other  assets  and  other  liabilities  and  accrued  expenses  and  approximate  their  fair  value  due  to  their  short  term  nature. 
Categorized under Level 2 in the fair value hierarchy. 

F-46

 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

(13) Liability for Unpaid Claims and Claim Adjustment Expenses

Roll forward of Claim Liability

The following table presents the activity in the net liability for unpaid losses and allocated loss adjustment expenses of short 
duration contracts for the following periods: 

Policy liabilities and unpaid claims balance as of January 1,
     Less: liabilities of policy-holder account balances, gross
     Less: non-insurance warranty benefit claim liabilities
Gross liabilities for unpaid losses and loss adjustment expenses
     Less: reinsurance recoverable on unpaid losses - short duration
     Less: other lines, gross
Net balance as of January 1, short duration

Incurred (short duration) related to:
     Current year
     Prior years
Total incurred

Paid (short duration) related to:
     Current year
     Prior years
Total paid

Net balance as of December 31, short duration
     Plus: reinsurance recoverable on unpaid losses - short duration
     Plus: other lines, gross
Gross liabilities for unpaid losses and loss adjustment expenses
     Plus: liabilities of policy-holder account balances, gross
     Plus: non-insurance warranty benefit claim liabilities
Policy liabilities and unpaid claims balance as of December 31, 

For the Year Ended December 31,

2023

2022

$ 

$ 

567,193  $ 
(1,923) 
(140) 
565,130 
(266,889) 
(184) 
298,057 

493,187 
(11,187) 
482,000 

234,723 
151,879 
386,602 

393,455 
448,117 
295 
841,867 
878 
2,103 
844,848  $ 

331,703 
(801) 
(10,785) 
320,117 
(165,129) 
(576) 
154,412 

361,462 
(858) 
360,604 

165,710 
51,249 
216,959 

298,057 
266,889 
184 
565,130 
1,923 
140 
567,193 

The following schedule reconciles the total amount of losses incurred on short duration contracts per the table above to the 
amount of total losses incurred as presented in the consolidated statements of operations, excluding the amount for member 
benefit claims:

Short duration incurred
Other lines incurred
Unallocated loss adjustment expenses

Total losses incurred

$ 

$ 

For the Year Ended December 31,
2022
2021
360,604  $ 
354 
643 
361,601  $ 

2023
482,000  $ 
30 
476 
482,506  $ 

252,906 
(284) 
851 
253,473 

During the year ended December 31, 2023, the Company experienced favorable prior year development of $11,187, primarily 
driven by lower-than-expected claims paid development in our commercial lines of business for the 2018 and 2020 accident 
years.

During the year ended December 31, 2022, the Company experienced favorable prior year development of $858, primarily as 
a result of lower-than-expected claim severity in our commercial lines of business.

During  the  year  ended  December  31,  2021,  the  Company  experienced  unfavorable  prior  year  development  of  $2,606, 
primarily  as  a  result  of  higher-than-expected  claim  severity  from  business  written  by  a  small  group  of  producers  of  our 

F-47

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

personal and commercial lines of business.

Management considers the prior year development for each of these years to be insignificant when considered in the context 
of  our  annual  earned  premiums,  net  as  well  as  our  net  losses  and  loss  adjustment  expenses  and  member  benefit  claims 
expenses. We analyze our development on a quarterly basis and given the short duration nature of our products, favorable or 
adverse  development  emerges  quickly  and  allows  for  timely  reserve  strengthening,  if  necessary,  or  modifications  to  our 
product  pricing  or  offerings.  The  favorable  prior  year  development  of  $11,187  in  the  year  ended  December  31,  2023 
represented 8.6% of our insurance business income before taxes of $129,816 and 3.8% of the opening net liability for losses 
and loss adjustment expenses of $298,057, as of January 1, 2023. The favorable prior year development of $858 in the year 
ended  December  31,  2022  represented  1.3%  of  our  insurance  business  income  before  taxes  of  $68,150,  and  0.6%  of  the 
opening net liability for losses and loss adjustment expenses of $154,412, as of January 1, 2022. The unfavorable prior year 
development of $2,606 in 2021 represented 3.7% of pretax income of $69,857 and 3.1% of the opening net liability for losses 
and loss adjustment expenses of $83,945, as of January 1, 2021.

Based upon our internal analysis and our review of the statement of actuarial opinions provided by our actuarial consultants, 
we believe that the amounts recorded for policy liabilities and unpaid claims reasonably represent the amount necessary to 
pay all claims and related expenses which may arise from incidents that have occurred as of the balance sheet date.

F-48

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Incurred and Paid Development

The  following  table  presents  information  about  incurred  and  paid  loss  development  and  average  claim  duration  as  of 
December 31, 2023, net of reinsurance, as well as cumulative claim frequency and the total of IBNR liabilities plus expected 
development on reported claims included within the net incurred claims amounts. The cumulative number of reported claims 
represents  open  claims,  claims  closed  with  payment,  and  claims  closed  without  payment.  It  does  not  include  an  estimated 
count of unreported claims. The number of claims is measured by claim event. The Company considers a claim that does not 
result in a liability as a claim closed without payment. 

Incurred Losses and Allocated Loss Adjustment Expenses, Net of Reinsurance

As of December 31, 2023

For the Years Ended December 31,

Unaudited

2014

2015

2016

2017

2018

2019

2020

2021

2022

2023

Total of 
IBNR 
Liabilities 
Plus 
Expected 
Development 
of Reported 
Claims

Cumulative 
Number of 
Reported 
Claims

$  43,449  $  39,614  $  39,914  $  39,887  $  39,874  $  39,869  $  39,883  $  39,884  $ 39,932  $  39,928  $ 

  59,579 

  57,470 

  57,588 

  57,815 

  58,141 

  58,194 

  58,248 

  58,285 

58,309  $ 

  84,178 

  87,290 

  87,993 

  88,615 

  89,629 

  89,981 

  89,516 

89,579  $ 

  103,306 

  104,898 

  105,601 

  105,787 

  106,446 

 106,517 

  106,592  $ 

  129,352 

  133,225 

  133,158 

  134,392 

 123,228 

  118,721  $ 

  144,925 

  149,166 

  151,772 

 153,325 

  151,994  $ 

— 

— 

93 

128 

1,679 

6,677 

  172,007 

  169,706 

 165,820 

  163,363  $ 

18,057 

  250,300 

 263,249 

  263,226  $ 

9,772 

 361,462 

  358,434  $ 

44,697 

  493,187  $ 

179,443 

Total $ 1,843,333 

122 

178 

257 

326 

399 

422 

344 

493 

542 

539 

Cumulative Paid Losses and Allocated Loss Adjustment Expenses, Net of Reinsurance

Unaudited

2014

2015

2016

2017

2018

2019

2020

2021

2022

2023

$  30,435  $  38,752  $  39,596  $  39,822  $  39,818  $  39,874  $  39,878  $  39,881  $ 39,927  $  39,885 

  41,578 

  56,445 

  57,130 

  57,610 

  58,096 

  58,175 

  58,243 

  58,274 

  62,989 

  84,185 

  86,531 

  88,482 

  88,976 

  89,474 

  89,286 

58,307 

89,390 

  84,493 

  102,620 

  105,075 

  105,852 

  106,402 

 106,249 

  106,416 

  105,740 

  112,619 

  114,490 

  115,407 

 114,756 

  115,500 

  122,348 

  128,787 

  132,747 

 131,885 

  134,261 

  127,721 

  129,832 

 132,997 

  138,004 

  174,334 

 224,193 

  234,328 

Accident 
Year

2014

2015

2016

2017

2018

2019

2020

2021

2022

2023

Accident 
Year

2014

2015

2016

2017

2018

2019

2020

2021

2022

2023

 165,710 

  299,064 

  234,723 

Total $ 1,449,878 

— 

$  393,455 

All outstanding liabilities before 2014, net of reinsurance

Liabilities for loss and loss adjustment expenses, net of reinsurance

Duration

The following table presents supplementary information about average historical claims duration as of December 31, 2023 
for short duration contracts:

Average Annual Percentage Payout of Incurred Claims by Age, Net of Reinsurance (Unaudited)

Years

1

2

3

4

5

6

Short duration

70.5%

17.2%

2.3%

1.1%

0.5%

0.3%

7

—%

8

0.1%

9

—%

10

—%

F-49

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Reconciliation of Reserves to Balance Sheet

The  following  table  presents  a  reconciliation  of  net  outstanding  liabilities  for  unpaid  loss  and  loss  adjustment  expenses  of 
short-duration contracts to the consolidated balance sheets value of policy liabilities and unpaid claims:

Net outstanding liabilities:
Short duration
Insurance lines other than short duration

Total liabilities for unpaid losses and loss adjustment expenses, net of reinsurance

Reinsurance recoverable on unpaid losses and loss adjustment expenses:
Short duration
Other insurance lines

Total reinsurance recoverable on unpaid losses and loss adjustment expenses

Total gross liability for unpaid losses and loss adjustment expenses

Liabilities of policy-holder account balances, gross
Non-insurance warranty benefit claim liabilities

Total policy liabilities and unpaid claims

As of 
December 31, 2023

$ 

$ 

393,455 
125 
393,580 

448,117 
170 
448,287 

841,867 
878 
2,103 
844,848 

(14) Revenue from Contracts with Customers

The Company’s revenues from insurance and contractual and liability insurance operations are primarily accounted for under 
Financial Services-Insurance (ASC 944) that are not within the scope of Revenue for Contracts with Customers (ASC 606). 
The  Company’s  remaining  revenues  that  are  within  the  scope  of  Topic  606  are  primarily  comprised  of  revenues  from 
contracts with customers for monthly membership dues for motor clubs, monthly administration fees for services provided 
for premiums, claims and reinsurance processing revenues, vehicle service contracts, vessel related revenue and revenues for 
household goods and appliances service contracts (collectively, remaining contracts). 

The  following  table  presents  the  disaggregated  amounts  of  revenue  from  contracts  with  customers  by  product  type  for  the 
following periods:

For the Year Ended December 31,
2022

2021

2023

Service and Administrative Fees:

Service contract revenue
Motor club revenue
Other

Revenue from contracts with customers

Service and Administrative Fees

$ 

$ 

289,660  $ 
46,394 
5,305 
341,359  $ 

210,817  $ 
53,346 
36,060 
300,223  $ 

163,583 
41,634 
53,346 
258,563 

Service and administrative fees are generated from non-insurance programs including warranty service contracts, motor clubs 
and  other  services.  Service  and  administrative  fees  are  recognized  consistent  with  the  earnings  recognition  pattern  of  the 
underlying policies, debt cancellation contracts and motor club memberships being administered, using pro rata, Rule of 78’s, 
modified Rule of 78’s, or other methods as appropriate for the contract. Management selects the appropriate method based on 
available information, and periodically reviews the selections as additional information becomes available. 

Management reviews the financial results under each significant contract on a monthly basis. Any losses that may occur due 
to a specific contract would be recognized in the period in which the loss is determined to be probable. 

We  do  not  disclose  information  about  remaining  performance  obligations  pertaining  to  contracts  that  have  an  original 
expected  duration  of  one  year  or  less.  The  transaction  price  allocated  to  remaining  unsatisfied  or  partially  unsatisfied 
performance obligations with an original expected duration exceeding one year was not material as of December 31, 2023.

F-50

 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

The timing of our revenue recognition may differ from the timing of payment by our customers. We record a receivable when 
revenue  is  recognized  prior  to  payment  and  we  have  an  unconditional  right  to  payment.  Alternatively,  when  payment 
precedes the provision of the related services, we record deferred revenue until the performance obligations are satisfied.

The following table presents the activity in the significant deferred assets and liabilities related to revenue from contracts with 
customers for the following period:

Deferred acquisition costs

Service and Administrative Fees:

Service contract revenue
Motor club revenue

Total

Deferred revenue

Service and Administrative Fees:

Service contract revenue
Motor club revenue
Other

Total

January 1, 2023

December 31, 2023

Beginning balance

Additions

Amortization

Ending balance

$ 

$ 

$ 

$ 

172,129  $ 
17,142 
189,271  $ 

122,537  $ 
36,085 
158,622  $ 

92,763  $ 
36,591 
129,354  $ 

581,882  $ 
22,949 
— 
604,831  $ 

313,203  $ 
45,122 
3,953 
362,278  $ 

289,660  $ 
46,394 
3,953 
340,007  $ 

201,903 
16,636 
218,539 

605,425 
21,677 
— 
627,102 

For the periods presented, no write-offs for unrecoverable deferred acquisition costs and deferred revenue were recognized.

(15) Other Assets and Other Liabilities and Accrued Expenses

Other Assets

The following table presents the components of other assets as reported in the consolidated balance sheets:

Accrued investment income
Loans eligible for repurchase
Mortgage servicing rights
Right of use assets - operating leases (1)
Income tax receivable
Furniture, fixtures and equipment, net
Prepaid expenses
Other

Total other assets

As of December 31,
2022
2023

$ 

$ 

6,269  $ 
32,183 
40,836 
31,469 
1,275 
29,624 
12,985 
10,874 
165,515  $ 

3,919 
32,136 
41,426 
31,499 
19,790 
21,829 
18,526 
3,018 
172,143 

 (1) See Note (21) Commitments and Contingencies for additional information.
The following table presents the depreciation expense related to furniture, fixtures and equipment for the following periods:

For the Year Ended December 31,
2022

2021

2023

Depreciation expense related to furniture, fixtures and equipment

$ 

6,370  $ 

3,954  $ 

3,621 

F-51

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Other Liabilities and Accrued Expenses

The following table presents the components of other liabilities and accrued expenses as reported in the consolidated balance 
sheets:

Accounts payable and accrued expenses
Loans eligible for repurchase liability
Deferred tax liabilities, net
Operating lease liabilities (1)
Commissions payable
Securities sold, not yet purchased
Derivative liabilities
Due to broker/trustee
Other

Total other liabilities and accrued expenses

  (1) See Note (21) Commitments and Contingencies for additional information.

(16) Other Revenue and Other Expenses

Other Revenue

As of December 31,

2023

2022

114,568  $ 
32,183 
139,845 
40,403 
36,728 
— 
4,503 
17,054 
18,460 
403,744  $ 

119,394 
32,136 
90,391 
38,031 
42,741 
16,575 
13,201 
39 
15,240 
367,748 

$ 

$ 

The following table presents the components of other revenue as reported in the consolidated statement of operations. Other 
revenue is primarily generated by Tiptree Capital’s non-insurance activities except as noted in the footnote to the table.

For the Year Ended December 31,
2022

2021

2023

Other investment income (1)
Financing interest income
Other (2)

Total other revenue

$ 

$ 

24,263  $ 
16,035 
18,605 
58,903  $ 

53,660  $ 
12,290 
10,235 
76,185  $ 

64,580 
7,592 
1,235 
73,407 

(1)

(2) 

See Note (6) Investments for the components of Other investment income.
Includes $15,654, $5,269 and $2,792 for the years ended December 31, 2023, 2022 and 2021, respectively, related to Insurance. 

Other Expenses

The following table presents the components of other expenses as reported in the consolidated statement of operations:

For the Year Ended December 31,
2022

2021

2023

General and administrative
Professional fees
Premium taxes
Mortgage origination expenses
Rent and related
Other

Total other expenses

$ 

$ 

38,086  $ 
28,292 
19,137 
12,248 
15,871 
17,284 
130,918  $ 

26,216  $ 
26,614 
22,362 
17,540 
17,635 
22,213 
132,580  $ 

36,654 
27,285 
20,196 
17,451 
17,009 
23,449 
142,044 

F-52

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

(17) Stockholders' Equity

Stock Repurchases

The  Board  of  Directors  authorized  the  Company  to  make  repurchases  of  up  to  $20,000  of  shares  of  the  Company’s 
outstanding common stock in the aggregate, at the discretion of the Company's Executive Committee. There were no shares 
repurchased  during  the  year  ended  December  31,  2023.  As  of  December  31,  2023,  the  remaining  repurchase  authorization 
was $11,945.

Tiptree Warrants

In  the  year  ended  December  31,  2022,  warrants  were  exercised  for  1,999,989  shares  of  Tiptree  common  stock,  with 
1,979,325 warrants exercised for $13,724 in cash, and 20,664 exercised cashless. As of December 31, 2023 and 2022, there 
were no warrants for shares of Tiptree common stock outstanding.

Dividends

The Company declared cash dividends per share for the following periods presented below:

Dividends per share for the
For the Year Ended December 31,
2022

2021

2023

First quarter
Second quarter
Third quarter
Fourth quarter

Total cash dividends declared

Fortegra Non-Controlling Interests

$ 

$ 

0.05  $ 
0.05 
0.05 
0.05 
0.20  $ 

0.04  $ 
0.04 
0.04 
0.04 
0.16  $ 

0.04 
0.04 
0.04 
0.04 
0.16 

On June 21, 2022, the Company closed the WP Transaction. On that date, Fortegra converted to a Delaware corporation and 
Warburg  made  a  $200,000  investment  in  Fortegra  in  exchange  for  Fortegra  Common  Stock,  Fortegra  Preferred  Stock, 
Fortegra  Warrants  and  Fortegra  Additional  Warrants.  Also,  in  connection  with  the  closing  of  the  WP  Transaction,  Tiptree 
was issued Fortegra Additional Warrants, and management’s interests in LOTS Intermediate were exchanged for interests in 
Fortegra. As of December 31, 2022, Fortegra was owned approximately 79.5% by Tiptree Holdings, 17.4% by Warburg and 
3.1% by management and directors of Fortegra. As a result of the WP Transaction, for the year ended December 31, 2022, 
the  Company  recorded  an  increase  of  $167,008  to  total  stockholders’  equity  of  which  $48,285  impacted  Tiptree  Inc. 
stockholders’  equity  and  $118,723  impacted  non-controlling  interests.  Of  the  increase  to  Tiptree  Inc.  stockholders’  equity, 
$41,092  impacted  additional  paid  in  capital  and  $7,193  impacted  accumulated  other  comprehensive  income  (loss). 
Additionally, the Company recognized $9,059 of net income attributable to non-controlling interests during the year ended 
December  31,  2022  due  to  the  increase  in  non-controlling  interest.  As  of  December  31,  2023,  Fortegra  was  owned 
approximately 79.5% by Tiptree Holdings, 17.5% by Warburg and 3.0% by management and directors of Fortegra. 

Fortegra Preferred Stock

The face amount of the Fortegra Preferred Stock is $80,000. Dividends are cumulative and accrue at a rate of 8% per annum, 
compounding quarterly. Any quarterly dividend may be paid in cash, at Fortegra’s option. For the years ended December 31, 
2023 and 2022, cash dividends declared were $6,400 and $3,384, respectively.

F-53

 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Warburg has the option to convert, at any time, its shares of Fortegra Preferred Stock into shares of Fortegra Common Stock 
at an initial conversion premium of 33% to Warburg’s initial investment valuation (the “Fortegra Preferred Stock Conversion 
Price”).  The  Fortegra  Preferred  Stock  Conversion  Price  is  adjusted  for  any  Fortegra  Common  Stock  splits,  dividends, 
extraordinary dividends and similar transactions. All of the Fortegra Preferred Stock will automatically convert into shares of 
Fortegra  Common  Stock  at  the  Fortegra  Preferred  Stock  Conversion  Price  upon  the  closing  of  a  qualifying  initial  public 
offering,  subject  to  a  five  year  make-whole  provision.  Upon  conversion,  the  Fortegra  Preferred  Stock  would  result  in 
Warburg owning an additional 6.6% interest in Fortegra, for a total as converted ownership of 24.0% (including its ownership 
of Fortegra Common Stock).

Fortegra Warrants

The Fortegra Warrants have a seven-year term and an exercise premium of 33% to Warburg’s initial investment valuation 
(the  “Fortegra  Warrant  Exercise  Price”).  The  Fortegra  Warrant  Exercise  Price  will  be  reduced  by  any  Fortegra  Common 
Stock cash dividends made by Fortegra and adjusted for stock splits, common stock dividends, extraordinary dividends and 
similar  transactions.  The  Fortegra  Warrants,  if  exercised  with  cash,  would  result  in  Warburg  owning  an  additional  3.8% 
interest in Fortegra.

Fortegra Additional Warrants

The Fortegra Additional Warrants issued to both Warburg and Tiptree have a seven-year term and an exercise price of $0.01 
per  share  of  Fortegra  Common  Stock.  The  Fortegra  Additional  Warrants  issued  to  Warburg  will  be  forfeited  based  on 
Warburg achieving an all-in return on its investment in excess of 23%, as measured primarily by Fortegra’s Common Stock 
price. The Fortegra Additional Warrants issued to Warburg are classified as liabilities, at fair value. The Fortegra Additional 
Warrants  issued  to  Tiptree  will  vest  based  on  Warburg  achieving  an  all-in  return  on  its  investment  in  excess  of  30%,  as 
measured  primarily  by  Fortegra’s  Common  Stock  price.  The  number  of  shares  of  Fortegra  Common  Stock  issuable  to 
Warburg  or  Tiptree  with  respect  to  the  Fortegra  Additional  Warrants  is  subject  to  adjustment  for  Fortegra  Common  Stock 
splits, stock or cash dividends and similar transactions. The Fortegra Additional Warrants are exercisable from the earlier of a 
transaction  that  results  in  Warburg  having  sold  50%  of  its  Fortegra  Common  Stock  or  the  fifth  anniversary  of  the  closing 
date.  The  maximum  number  of  shares  issued  to  Warburg  or  Tiptree,  if  exercised  with  cash,  would  be  an  additional  1.7% 
interest in Fortegra on an as converted basis (including its ownership of Fortegra Common and Preferred Stock).

The following table presents the components of non-controlling interests as reported in the consolidated balance sheets:

Fortegra preferred interests
Fortegra common interests
Other third-party common interests
Total non-controlling interests

As of December 31,
2022
2023

$ 

$ 

77,679  $ 
82,020 
— 
159,699  $ 

77,679 
55,364 
3,165 
136,208 

Statutory Reporting and Insurance Company Subsidiaries Dividend Restrictions

The Company’s U.S. insurance subsidiaries prepare financial statements in accordance with Statutory Accounting Principles 
(SAP)  prescribed  or  permitted  by  the  insurance  departments  of  their  states  of  domicile.  Prescribed  SAP  includes  the 
Accounting Practices and Procedures Manual of the NAIC as well as state laws, regulations and administrative rules. 

Statutory Capital and Surplus

The Company’s insurance company subsidiaries must maintain minimum amounts of statutory capital and surplus as required 
by regulatory authorities, including the NAIC; their capital and surplus levels exceeded respective minimum requirements as 
of December 31, 2023 and 2022.

Combined statutory capital and surplus of the Company's insurance company subsidiaries

Required minimum statutory capital and surplus

As of December 31,
2022
2023

$ 

$ 

454,540  $ 

370,340 

75,750  $ 

75,750 

F-54

 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Under the NAIC Risk-Based Capital Act of 1995, a company's Risk-Based Capital (RBC) is calculated by applying certain 
risk factors to various asset, claim and reserve items. If a company's adjusted surplus falls below calculated RBC thresholds, 
regulatory intervention or oversight is required. The Company's U.S. domiciled insurance company subsidiaries' RBC levels, 
as calculated in accordance with the NAIC’s RBC instructions, exceeded all RBC thresholds as of December 31, 2023 and 
2022.

The following table presents the statutory net income of the Company’s U.S. domiciled statutory insurance companies for the 
following periods:

Net income of statutory insurance companies

For the Year Ended December 31,
2021
2022
2023

$ 

47,384  $ 

12,964  $ 

33,999 

The Company also has a foreign insurance subsidiary that is not subject to SAP. The statutory capital and surplus amounts 
and statutory net income presented above do not include the foreign insurance subsidiary in accordance with SAP.

Statutory Dividends

The  Company’s  U.S.  domiciled  insurance  company  subsidiaries  may  pay  dividends  to  the  Company,  subject  to  statutory 
restrictions. Payments in excess of statutory restrictions (extraordinary dividends) to the Company are permitted only with 
prior approval of the insurance department of the applicable state of domicile. The Company eliminates all dividends from its 
subsidiaries in the consolidated financial statements. 

The following table presents the dividends paid to the Company by its U.S domiciled insurance company subsidiaries and the 
combined amount available for ordinary dividends of the Company's U.S. domiciled insurance company subsidiaries for the 
following periods:

Ordinary dividends
Total dividends

For the Year Ended 
December 31, 

2023

2022

$ 
$ 

27,114  $ 
27,114  $ 

— 
— 

As of

December 31,
2023

December 31, 
2022

Amount available for ordinary dividends of the Company's insurance company subsidiaries

$ 

24,327  $ 

35,145 

At December 31, 2023, the maximum amount of dividends that our U.S. domiciled insurance company subsidiaries could pay 
under  applicable  laws  and  regulations  without  regulatory  approval  was  approximately  $24,327.  The  Company  may  seek 
regulatory  approval  to  pay  dividends  in  excess  of  this  permitted  amount,  but  there  can  be  no  assurance  that  the  Company 
would receive regulatory approval if sought.

F-55

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

(18) Accumulated Other Comprehensive Income (Loss) (AOCI)

The following table presents the activity of AFS securities in AOCI, net of tax, for the following periods:

Unrealized 
gains (losses) 
on available 
for sale 
securities

Foreign 
currency 
translation 
adjustment

Total AOCI

Amount 
attributable 
to non-
controlling 
interests

Total AOCI 
to Tiptree 
Inc.

Balance at December 31, 2021

$ 

(2,686)  $ 

Other comprehensive income (losses) before reclassifications
Amounts reclassified from AOCI
WP Transaction

OCI

Balance at December 31, 2022

Balance at December 31, 2022

Other comprehensive income (losses) before reclassifications
Amounts reclassified from AOCI

OCI

Balance at December 31, 2023

$ 

$ 

$ 

(39,514) 
(843) 
— 
(40,357) 
(43,043)  $ 

—  $ 
(7,311)   
— 
— 
(7,311)   
(7,311)  $ 

(2,686)  $ 
(46,825) 
(843) 
— 
(47,668) 
(50,354)  $ 

(43,043)  $ 
8,716 
2,182 
10,898 
(32,145)  $ 

(7,311)  $ 
7,213 
— 
7,213 

(98)  $ 

(50,354)  $ 
15,929 
2,182 
18,111 
(32,243)  $ 

1  $ 

3,731 
— 
7,193 
10,924 
10,925  $ 

10,925  $ 
(4,755) 
— 
(4,755) 
6,170  $ 

(2,685) 
(43,094) 
(843) 
7,193 
(36,744) 
(39,429) 

(39,429) 
11,174 
2,182 
13,356 
(26,073) 

The following table presents the reclassification adjustments out of AOCI included in net income and the impacted line items 
on the consolidated statement of operations for the following periods:

For the Year Ended December 31,

Components of AOCI
Unrealized gains (losses) on available for 
sale securities
Related tax (expense) benefit

Net of tax

2023

2022

2021

$ 

$ 

(2,812)  $ 

1,359  $ 

630 
(2,182)  $ 

(516)   
843  $ 

638 

(139) 
499 

Affected line item in consolidated 
statements of operations
Net realized and unrealized gains (losses)

Provision for income tax

(19) Stock Based Compensation

Tiptree Equity Plans

The  table  below  summarizes  changes  to  the  issuances  under  the  Company’s  2017  Omnibus  Incentive  Equity  Plan  for  the 
periods  indicated,  excluding  awards  granted  under  the  Company’s  subsidiary  incentive  plans  that  are  exchangeable  for 
Tiptree common stock:

2017 Equity Plan
Available for issuance as of December 31, 2020

RSU, stock and option awards granted
Forfeited
Exchanged for vested subsidiary awards
Available for issuance as of December 31, 2021

RSU, stock and option awards granted
Forfeited
Amendment to 2017 Equity Plan
PRSU awards granted
Exchanged for vested subsidiary awards
Available for issuance as of December 31, 2022

RSU, stock and option awards granted

Available for issuance as of December 31, 2023

F-56

Number of 
shares 
3,788,417 
(61,713) 
(215,583) 
(1,166,307) 
2,344,814 
(247,093) 
5,276 
4,000,000 
(3,616,667) 
(114,353) 
2,371,977 
(111,427) 
2,260,550 

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Restricted Stock Units (RSUs) and Stock Awards

The Company values RSUs at their grant-date fair value as measured by Tiptree’s common stock price. Generally, the Tiptree 
RSUs vest and become non-forfeitable either (i) after the third anniversary, or (ii) with respect to one-third of Tiptree shares 
granted  on  each  of  the  first,  second  and  third  year  anniversaries  of  the  grant  date.  RSU  awards  are  expensed  using  the 
straight-line method over the requisite service period. The RSUs granted after 2019 include a retirement provision and are 
amortized over the lesser of the service condition or expected retirement date. Stock awards issued as director compensation 
are deemed to be granted and immediately vested upon issuance. 

The following table presents changes to the issuances of RSUs and stock awards under the 2017 Omnibus Incentive Equity 
Plan for the periods indicated:

Unvested units as of December 31, 2020

Granted
Vested

Unvested units as of December 31, 2021

Granted
Vested
Forfeited 

Unvested units as of December 31, 2022

Granted
Vested

Unvested units as of December 31, 2023 (1)
(1)   

 Includes 62,940 shares that vest ratably over two years and 108,418 and 81,874 shares that cliff vest in 2025 and 2026, respectively.

Number of 
shares 
issuable

Weighted 
average grant 
date fair value
6.52 
7.81 
6.62 
6.59 
12.83 
7.13 
10.10 
9.63 
16.09 
8.38 
14.25 

953,145  $ 
61,713 
(415,846) 
599,012  $ 
247,093 
(339,822) 
(5,276) 
501,007  $ 
111,427 
(359,203) 
253,231  $ 

The following tables present the detail of the granted and vested RSUs and stock awards for the periods indicated:

For the Year Ended December 31,
2022

2023

2021

Vested

For the Year Ended December 31,
2022

2023

2021

Granted
Directors
Employees 

29,553 
81,874 

39,517 
207,576 

61,713  Directors

—  Employees

Total Granted

111,427 

247,093 

61,713 

Total 
Vested

Taxes

Net Vested

Tiptree Senior Management Incentive Plan

29,553 
329,650 

359,203 
(43,322) 
315,881 

39,517 
300,305 

339,822 
(47,274)   
292,548 

61,713 
354,133 

415,846 
(34,828) 
381,018 

On  August  4,  2021,  a  total  of  3,500,000  Performance  Restricted  Stock  Units  (PRSUs)  were  awarded  to  members  of  the 
Company’s senior management. An additional 350,000 PRSUs were awarded on October 14, 2022. The PRSUs have a 10-
year  term  and  are  subject  to  the  recipient’s  continuous  service  and  a  market  requirement.  A  portion  of  the  PRSUs  will 
generally vest upon the achievement of each of five Tiptree share price target milestones ranging from $15 to $60, adjusted 
for dividends paid, within five pre-established determination periods (subject to a catch-up vesting mechanism) occurring on 
the second, fourth, sixth, eighth and tenth anniversaries of the grant date.

In November 2021, the first tranche of the PRSUs vested, resulting in a net issuance of 215,583 shares of Tiptree common 
stock. As of December 31, 2023, 3,616,667 PRSUs are unvested. The below table illustrates the aggregate number of PRSUs 
that will vest upon the achievement of each Tiptree share price target. Such price targets are adjusted down for cumulative 
dividends paid by the Company since grant (e.g., the next share price target is $19.56 as adjusted for cumulative dividends 
paid to date).

Original Tiptree Share Price Target
$20
$30

Number of PRSUs that Vest
516,667
775,000

F-57

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

$45
$60

1,033,333
1,291,667

Upon vesting, the Company will issue shares, or if shares are not available under the 2017 Equity Plan, then the Company 
may in its sole discretion instead deliver cash equal to the fair market value of the underlying shares. The fair value of the 
PRSUs was estimated using a Black-Scholes-Merton option pricing formula embedded within a Monte Carlo model used to 
simulate  the  future  stock  prices  of  the  Company,  which  assumes  that  the  market  requirement  is  achieved.  The  historical 
volatility was computed based on historical daily returns of the Company’s stock price simulated over the performance period 
using a lookback period of 10 years. The valuation was done under a risk-neutral framework using the 10-year zero-coupon 
risk-free interest rate derived from the Treasury Constant Maturities yield curve on the reporting date. The current quarterly 
dividend rates in effect as of the reporting date are used to calculate a spot dividend yield for use in the model.

The following table presents the assumptions used to measure the fair value of the PRSUs as of June 7, 2022, when they were 
converted to equity awards.

Valuation Input 

Historical volatility
Risk-free rate
Dividend yield
Cost of equity
Expected term (years)

Stock Option Awards

Assumption
38.75%
3.04%
1.45%
11.72%
6

Between  2016  and  2020,  option  awards  were  granted  to  the  Executive  Committee  with  an  exercise  price  equal  to  the  fair 
market  value  of  our  common  stock  on  the  date  of  grant.  The  option  awards  have  a  10-year  term  and  are  subject  to  the 
recipient’s continuous service, a market requirement, and vest one third on each of the three, four, and five-year anniversaries 
of  the  grant  date.  As  of  December  31,  2023,  the  market  requirement  for  all  outstanding  options  has  been  achieved.  There 
were no stock option awards granted in 2022 or 2023.

The following table presents the Company's stock option activity for the current period: 

Balance, December 31, 2022

Balance, December 31, 2023

Options 
outstanding

Weighted average 
exercise price (in 
dollars per stock 
option)

Weighted average 
grant date value 
(in dollars per 
stock option)

1,675,514  $ 

1,583,873  $ 

6.50  $ 

6.51  $ 

2.30 

2.25 

Options 
exercisable

1,018,805 

1,225,083 

Weighted average remaining contractual term at 
December 31, 2023 (in years)

4.3

Subsidiary Equity Plans

Certain  of  the  Company’s  subsidiaries  have  established  incentive  plans  under  which  they  are  authorized  to  issue  equity  of 
those  subsidiaries  to  certain  of  their  employees.  Such  awards  are  accounted  for  as  equity  unless  otherwise  noted.  These 
awards are subject to performance-vesting criteria based on the performance of the subsidiary (performance vesting awards) 
and time-vesting subject to continued employment (time vesting awards). The Company has the option, but not the obligation 
to settle the exchange right in cash.

Fortegra Equity Incentive Plan

Fortegra adopted the 2022 Equity Incentive Plan (“Fortegra Plan”) on June 21, 2022, which permits the grant of RSUs, stock 
based awards and options up to 7.2% of Fortegra Common Stock (assuming conversion of the Fortegra Preferred Stock), of 
which the substantial majority is expected to be delivered in options. As of December 31, 2023, time vesting RSUs and time 
and performance vesting options representing approximately 5.3% of Fortegra Common Stock (assuming conversion of the 
Fortegra  Preferred  Stock)  have  been  granted  and  remain  unvested.  The  general  purpose  of  the  Fortegra  Plan  is  to  attract, 
motivate  and  retain  selected  employees  of  Fortegra,  to  provide  them  with  incentives  and  rewards  for  performance  and  to 

F-58

 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

better  align  their  interests  with  those  of  Fortegra’s  stockholders.  Unless  otherwise  extended,  the  Fortegra  Plan  terminates 
automatically on June 21, 2032. The awards under the Fortegra Plan are not exchangeable for Tiptree common stock. 

In May 2023 and November 2023, Fortegra granted management options with a strike price equal to the per share price on 
the date of the WP Transaction, delivered in equal portions of time and performance vested grants equal to approximately 
5.0% of Fortegra Common Stock (assuming cash exercise and after conversion of the Fortegra Preferred Stock). The time 
vested options vest in equal parts over five years and expire on the ten year anniversary of the grant date. The performance 
vested options vest based on specific internal rate of return targets determined at the time of a change of control of Fortegra 
or sale by Warburg of more than 50% of its Fortegra securities (on an as converted basis) acquired in 2022. The fair value 
option grants were estimated on the date of grant using a Black-Scholes Merton option pricing formula embedded within a 
Monte Carlo model used to simulate the future value of Fortegra Common Stock, which assumes the market requirement is 
achieved. Key assumptions used in the model were a historical volatility of 45.0%, a risk free rate of 3.7%, no dividend yield 
and an expected term of 4.2 years.

In  May  2023,  Fortegra  granted  time  vesting  RSUs  equal  to  approximately  0.1%  of  Fortegra  Common  Stock  (assuming 
conversion of the Fortegra Preferred Stock). The RSUs include a retirement provision and are amortized over the lesser of the 
service condition or expected retirement date.

In  May  2023  and  November  2023,  Fortegra  granted  performance  based  restricted  stock  units  (Fortegra  PRSUs)  that  vest 
based on the achievement of specified gross written premium volume targets and underwriting ratios for selected specialty 
insurance  lines  written  in  2024.  Upon  vesting,  the  Fortegra  PRSUs  entitle  recipients  to  participate  in  an  aggregate  pool  of 
between $5,000 and $20,000 payable in shares of Fortegra. The Fortegra PRSUs are accounted for as liability awards and 
were unvested as of December 31, 2023.

The  following  table  presents  changes  to  the  issuances  of  subsidiary  awards  under  the  subsidiary  incentive  plans  for  the 
periods indicated: 

Unvested balance as of December 31, 2019

Granted
Vested
Performance assumption adjustment
Unvested balance as of December 31, 2020

Granted
Vested
Performance assumption adjustment
Unvested balance as of December 31, 2022

Granted
Vested

Unvested balance as of December 31, 2023

Grant date 
fair value of 
equity shares 
issuable

$ 

$ 

$ 

$ 

4,279 
1,108 
(4,237) 
3,155 
4,305 
1,278 
(3,472) 
123 
1,487 
19,930 
(808) 
20,609 

F-59

 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Stock Based Compensation Expense

The following table presents total stock based compensation expense and the related income tax benefit recognized on the 
consolidated statements of operations: 

For the Year Ended December 31,
2022

2021

2023

Employee compensation and benefits
Director compensation
Income tax benefit

Net stock based compensation expense

$ 

$ 

7,866  $ 
409 
(1,738) 
6,537  $ 

9,219  $ 
469 
(2,034) 
7,654  $ 

10,665 
465 
(2,338) 
8,792 

Additional information on total non-vested stock based compensation is as follows:

As of December 31, 2023

Unrecognized compensation cost related to non-vested awards (1)
Weighted - average recognition period (in years)

Stock options
$ 

17,031  $ 
2.2

Restricted 
stock awards 
and RSUs

Performance 
Restricted 
Stock Units

1,497  $ 
0.8

4,280 
1.0

(1) 

Includes unrecognized compensation cost of $17,031 related to stock options, $779 related to RSUs, and $583 related to PRSUs at The Fortegra Group.

(20) Income Taxes

The following table presents the Company’s provision (benefit) for income taxes reflected as a component of income (loss):

For the Year Ended December 31,
2022

2021

2023

Current provision (benefit) for income taxes:

Federal
State
Foreign
Total current provision (benefit) for income taxes

Deferred provision (benefit) for income taxes:

Federal
State
Foreign

Total deferred provision (benefit) for income taxes

Total provision (benefit) for income taxes

$ 

$ 

2,118  $ 
940 
2,974 
6,032 

250  $ 

1,612 
1,041 
2,903 

38,126 
(1,446) 
344 
37,024 
43,056  $ 

39,983 
7,155 
409 
47,547 
50,450  $ 

1,393 
1,330 
838 
3,561 

13,819 
4,435 
(524) 
17,730 
21,291 

On  June  21,  2022,  the  WP  Transaction  was  completed,  in  which  Warburg  invested  $200,000  in  Tiptree’s  insurance 
subsidiary,  Fortegra.  The  WP  Transaction,  along  with  Fortegra  management’s  ownership,  reduced  Tiptree’s  ownership  in 
Fortegra  below  80%  such  that,  while  still  consolidated  for  GAAP  financial  reporting  purposes,  Fortegra  will  no  longer  be 
included  in  the  consolidated  tax  return  group  with  Tiptree.  Tiptree  recorded  deferred  tax  liabilities  related  to  the  basis 
difference  in  Tiptree’s  investment  in  Fortegra  as  of  December  31,  2022.  This  deferred  tax  liability  represents  the  tax  that 
would be due, before consideration of loss carryforwards, if Tiptree were to sell any of its Fortegra stock at its carrying value 
on  the  Company’s  balance  sheet.  The  deferred  tax  liability  as  of  December  31,  2022  relating  to  the  WP  Transaction  was 
$39,970, of which $14,064 was recorded directly in stockholders’ equity, a benefit of $2,424 in other comprehensive income 
and $28,330 as a provision for income taxes in the consolidated statements of operations for the year ended December 31, 
2022.  Additional  one  time  impacts  from  the  transaction  caused  $4,803  of  expense,  leading  to  $33,133  of  expense  in  the 
statement of operations.

For the year ended December 31, 2023, the deferred tax liability relating to Fortegra was $61,673, an increase of $21,703, of 
which $3,819 of expense was recorded in OCI, $1,217 of benefit was recorded directly in stockholders’ equity, and $19,101 
expense was recorded as a provision for income taxes.

Excluding the impact of these deferred taxes, the effective tax rates for the years ended December 31, 2023 and 2022, were 
28.8% and 32.1%, respectively.

F-60

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

The U.S. federal rate is before the consideration of rate reconciling items. A reconciliation of the expected federal provision 
(benefit) for income taxes on income using the federal statutory income tax rate to the actual provision (benefit) for income 
taxes and resulting effective income tax rate is as follows for the periods indicated below:

Income (loss) before income taxes

Federal statutory income tax rate

Expected federal provision (benefit) for income taxes at the federal statutory income 
tax rate

Effect of state provision (benefit) for income taxes, net of federal benefit
Effect of non-deductible compensation
Effect of tax deconsolidation of subsidiaries
Effect of change in valuation allowance
Effect of foreign operations
Effect of stock-based compensation
Effect of return-to-accrual
Effect of other items
Tax (benefit) on income

For the Year Ended December 31,

2023
83,053 

$ 

2022
54,011 

$ 

2021
65,342 

$ 

 21.0 %

 21.0 %

 21.0 %

17,441 
(1,971) 
3,376 
19,101 
518 
2,743 
(233) 
1,580 
501 
43,056 

$ 

11,342 
2,034 
3,292 
33,133 
3,285 
(18) 
(556) 
(509) 
(1,553) 
50,450 

$ 

13,721 
2,858 
4,518 
— 
1,692 
(541) 
(1,642) 
154 
531 
21,291 

$ 

Effective tax rate

 51.8 %

 93.4 %

 32.6 %

For the year ended December 31, 2023, the Company’s effective tax rate on income was equal to 51.8%. The effective tax 
rate  for  the  year  ended  December  31,  2023  is  higher  than  the  U.S.  statutory  income  tax  rate  of  21.0%  primarily  from  the 
impact of the tax deconsolidation of Fortegra and non-deductible compensation.

For the year ended December 31, 2022, the Company’s effective tax rate on income was equal to 93.4%. The effective tax 
rate  for  the  year  ended  December  31,  2022  is  higher  than  the  U.S.  statutory  income  tax  rate  of  21.0%  primarily  from  the 
impact of the tax deconsolidation of Fortegra and non-deductible compensation.

For the year ended December 31, 2021, the Company’s effective tax rate on losses was equal to 32.6%. The effective tax rate 
for the year ended December 31, 2021 is higher than the U.S. statutory income tax rate of 21.0% primarily from the impact of 
expected refunds arising from the CARES Act.

The table below presents the components of the Company’s net deferred tax assets and liabilities as of the respective balance 
sheet dates:

F-61

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Deferred tax assets:

Net operating loss carryforwards
Unrealized losses
Accrued expenses
Unearned premiums
Deferred revenue
Claims reserve
Lease liability
Other deferred tax assets

Total deferred tax assets

Less: Valuation allowance

Total net deferred tax assets

Deferred tax liabilities:

Property
Unrealized gains
Other deferred tax liabilities
Deferred acquisition cost
Advanced commissions
Right of use asset
Intangibles
Investment in Fortegra

Total deferred tax liabilities
Net deferred tax liability 

As of December 31,
2022
2023

$ 

$ 

30,834  $ 
28,926 
2,041 
61,112 
15,655 
6,351 
8,357 
3,311 
156,587 
(12,366) 
144,221 

3,266 
9,648 
246 
135,628 
48,975 
6,236 
18,394 
61,673 
284,066 
139,845  $ 

37,857 
31,482 
2,409 
52,904 
15,700 
5,705 
6,834 
1,966 
154,857 
(11,848) 
143,009 

3,058 
9,812 
411 
116,373 
43,961 
5,531 
14,284 
39,970 
233,400 
90,391 

As of January 2016, Tiptree established a U.S. federal consolidated income tax group and filed on a consolidated basis, with 
limited  exceptions.  As  of  June  2022,  Fortegra  and  its  subsidiaries  are  no  longer  part  of  Tiptree’s  consolidated  income  tax 
group  and  formed  their  own  tax  consolidation  group.  Tiptree’s  consolidated  group,  and  certain  subsidiaries  on  a  separate 
basis,  filed  returns  in  various  state  jurisdictions,  and  as  such  may  have  state  tax  obligations.  Additionally,  as  needed  the 
Company will take all necessary steps to comply with any income tax withholding requirements.

F-62

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

As  of  December  31,  2023,  the  Company  had  total  U.S.  Federal  net  operating  loss  carryforwards  (NOLs)  of  $51,099.  The 
following table presents the U.S. Federal NOLs by tax year of expiration:

Tax Year of Expiration
2026
2027
2028
2029
2030
2031
2032
2033
2034
2035
2036
2037
2038
2039
2040
2041
Indefinite

Total

As of
December 31, 2023

$ 

$ 

— 
— 
— 
— 
360 
— 
— 
— 
— 
— 
— 
— 
— 
— 
26,561 
— 
24,178 
51,099 

In addition to the U.S. Federal NOL, Tiptree and its subsidiaries have NOLs in various state jurisdictions totaling $19,757 as 
of December 31, 2023. Valuation allowances of $12,366 have been established for primarily state deferred tax assets, which 
are  primarily  state  NOLs,  since  management  has  concluded  it  is  more  likely  than  not  they  will  expire  unutilized  based  on 
existing positive and negative evidence. Management believes it is more likely than not the remaining NOLs and deferred tax 
assets will be utilized prior to their expiration dates. 

As  of  December  31,  2023,  the  consolidated  valuation  allowance  for  the  Company  was  $12,366.  In  2023,  the  Company 
recorded a net increase in its valuation allowances equal to $518, compared to a net increase in its valuation allowance of 
$3,285 in 2022.

As  of  December  31,  2023  and  2022,  the  Company  had  no  material  unrecognized  tax  benefits  or  accrued  interest  and 
penalties. Federal tax years 2015 and onward are open for examination as of December 31, 2023.

(21) Commitments and Contingencies

Operating Leases

All leases are office space leases and are classified as operating leases that expire through 2033. Some of our office leases 
include the option to extend for up to 5 years or less at management’s discretion. Such extension options were not included in 
the measurement of the lease liability. 

Below is a summary of our right of use asset and lease liability as of December 31, 2023:

F-63

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Right of use asset - Operating leases

Operating lease liability

Weighted-average remaining lease term (years)

Weighted-average discount rate (1)

As of
December 31, 2023
$31,469

$40,403

7.00

7.98%

(1) 

Discount rate was determined by applying available market rates to lease obligations based upon their term.

As of December 31, 2023, the approximate aggregate minimum future lease payments required for our lease liability over the 
remaining lease periods are as follows:

2024
2025
2026
2027
2028
2029 and thereafter

Total minimum payments
Less: present value adjustment

Total

As of
December 31, 2023
9,706 
$ 
9,670 
9,048 
7,217 
6,867 
16,864 
59,372 
18,969 
40,403 

$ 

The  following  table  presents  rent  expense  for  the  Company’s  office  leases  recorded  in  other  expenses  on  the  consolidated 
statements of operations for the following periods:

Rent expense for office leases (1)

For the Year Ended December 31,

2023

2022

2021

$ 

7,951  $ 

9,301  $ 

8,924 

(1)  

Includes lease expense of $0, $202, and $609 for the years ended December 31, 2023, 2022 and 2021, respectively, for assets classified as held for sale for the periods prior 
to July 1, 2022.

The Company entered into a sublease of their former corporate office space in December 2022. As a result of the sublease, 
future lease payments will be offset by $1,842 annually from July 2023 through and August 2029.

Litigation

The Company is a defendant in Mullins v. Southern Financial Life Insurance Co., a class action filed in February 2006, in 
Pike County Circuit Court in the Commonwealth of Kentucky on behalf of Kentucky consumers that purchased certain credit 
life  and  disability  insurance  coverage  between  1997-2007.  The  action  alleges  violations  of  the  Kentucky  Consumer 
Protection Act (“KCPA”) and certain insurance statutes, common law fraud and breach of contract and the covenant of good 
faith and fair dealing. The plaintiffs seek compensatory and punitive damages, attorneys’ fees and interest. 

Two classes were certified in June 2010: Subclass A includes class members who suffered a disability during the coverage 
period but allegedly received less than full disability benefits; Subclass B includes all class members whose loan termination 
date extended beyond the termination date of the credit disability coverage period. 

In a series of orders issued in October 2022 on competing motions for partial summary judgment, the court found in favor of 
the  plaintiffs  as  to  the  Subclass  A  breach  of  contract  claim  (the  Subclass  A  Order)  and,  as  to  Subclass  B,  found  that  the 
Company was unjustly enriched to the extent the premium it collected exceeded the proportion of the premium for which the 
Company provided benefits coverage (the Subclass B Order). The court found in favor of the Company as to the plaintiffs’ 
claims for common law fraud and violation of Kentucky’s insurance statutes and ordered the plaintiffs’ Motion for Sanctions 

F-64

 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

for Spoliation of Evidence held in abeyance. The Company has appealed the Subclass A Order and Subclass B Order and all 
interlocutory orders made final by entry of the Subclass A Order and Subclass B Order. 

In December 2022, the court dismissed the plaintiffs’ KCPA claims as to both Subclass A Order and Subclass B Order. The 
court  also  dismissed  the  plaintiffs’  breach  of  covenant  of  good  faith  and  fair  dealing  claim  as  to  Subclass  B  Order  but 
declined  to  dismiss  such  claim  as  to  Subclass  A  Order  pending  resolution  of  the  Company’s  appeal.  The  trial,  previously 
scheduled for December 2023 has been remanded while the matter is on appeal.

The Company considers such litigation customary in the insurance industry. In management's opinion, based on information 
available  at  this  time,  the  ultimate  resolution  of  such  litigation,  which  it  is  vigorously  defending,  should  not  be  materially 
adverse to the financial position of the Company. It should be noted that large punitive damage awards, bearing little relation 
to actual damages sustained by plaintiffs, have been awarded in certain states against other companies in the credit insurance 
business. At this time, the Company cannot estimate a range of loss that is reasonably possible.

The  Company  and  its  subsidiaries  are  parties  to  other  legal  proceedings  in  the  ordinary  course  of  business.  Although  the 
Company’s  legal  and  financial  liability  with  respect  to  such  proceedings  cannot  be  estimated  with  certainty,  the  Company 
does not believe that these proceedings, either individually or in the aggregate, are likely to have a material adverse effect on 
the Company’s financial position.

(22) Earnings Per Share

The  Company  calculates  basic  net  income  per  share  of  common  stock  (common  share)  based  on  the  weighted  average 
number  of  common  shares  outstanding,  which  includes  vested  corporate  RSUs.  Unvested  corporate  RSUs  have  a  non-
forfeitable right to participate in dividends declared and paid on the Company’s common stock on an as vested basis and are 
therefore considered a participating security. The Company calculates basic earnings per share using the “two-class” method 
under which the income available to common stockholders is allocated to the unvested corporate RSUs.

Diluted net income attributable to common stockholders includes the effect of unvested subsidiaries’ RSUs, when dilutive. 
The  assumed  exercise  of  all  potentially  dilutive  instruments  is  included  in  the  diluted  net  income  per  common  share 
calculation, if dilutive.

The following table presents a reconciliation of basic and diluted net income per common share for the following periods:

Net income (loss)
Less:

Net income (loss) attributable to non-controlling interests
Net income allocated to participating securities
Net income (loss) attributable to Tiptree Inc. common shares - basic

Effect of Dilutive Securities:
Securities of subsidiaries
Adjustments to income relating to exchangeable interests and contingent considerations, net 
of tax
Net income (loss) attributable to Tiptree Inc. common shares - diluted
Weighted average number of shares of common stock outstanding - basic

Weighted average number of incremental shares of common stock issuable from 
exchangeable interests and contingent considerations

Weighted average number of shares of common stock outstanding - diluted

Basic net income (loss) attributable to common shares
Diluted net income (loss) attributable to common shares

(23) Related Party Transactions

For the Year Ended December 31,
2022

2023

2021

$ 

39,997  $ 

3,561  $ 

44,051 

26,046 
100 
13,851 

11,835 
— 
(8,274)   

5,919 
703 
37,429 

(1,298)   

— 

(780) 

— 
12,553  $ 

$ 
 36,693,204 

— 
(8,274)  $ 

9 
36,658 
 33,223,792 

 35,531,149 

925,891 
 37,619,095 

— 
 35,531,149 

464,464 
 33,688,256 

$ 
$ 

0.38  $ 
0.33  $ 

(0.23)  $ 
(0.23)  $ 

1.13 
1.09 

Corvid  Peak  is  a  related  party  of  the  Company  because  Corvid  Peak  is  deemed  to  be  controlled  by  Michael  Barnes,  the 

F-65

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2023
(in thousands, except share data)

Company’s Executive Chairman. The Company is invested in funds managed by Corvid Peak (the Corvid Peak Funds) and 
Corvid Peak manages investment portfolio accounts of Fortegra and certain of its subsidiaries under an investment advisory 
agreement (the IAA). With respect to the Corvid Peak Funds and IAA, the Company incurred $5,206, $3,808, and $1,988 of 
management and incentive fees for the years ended December 31, 2023, 2022 and 2021, respectively.

Beginning  January  1,  2021,  Tiptree  has  been  allocated  10.2%  of  certain  profits  interests  earned  by  Corvid  Peak  with  an 
additional  10.2%  interest  for  each  of  the  next  consecutive  four  years.  Beginning  on  January  1,  2024,  Tiptree’s  percentage 
interest increased to 42.0% (including interests acquired from former Corvid Peak equity holders). 

On November 10, 2022, the Company contributed $505 of cash (representing its pro rata share) to Corvid Peak to fund an 
escrow account for the repurchase of a revenue share by a third party effective as of January 1, 2025.

Pursuant to the Transition Services Agreement, Tiptree and Corvid Peak have mutually agreed to provide certain services to 
one another. Payments under the Transition Services Agreement in the years ended December 31, 2023 and 2022 were not 
material.

Pursuant to a Partner Emeritus Agreement, Tiptree agreed to provide Mr. Inayatullah, a greater than 5% stockholder of the 
Company, support services and reimburse Mr. Inayatullah for a portion of benefit expenses in exchange for advice and other 
consulting  services  as  requested  by  the  Company’s  Executive  Committee.  Transactions  related  to  the  Partner  Emeritus 
Agreement in the years ended December 31, 2023 and 2022 were not material.

(24) Subsequent Events

On  January  1,  2024,  Tiptree  granted  550,000  performance  restricted  stock  units  (PRSUs)  to  each  of  Michael  Barnes, 
Executive Chairman and Jonathan Ilany, Chief Executive Officer and awarded 183,333 PRSUs to Randy Maultsby, President 
and 137,500 PRSUs to Scott McKinney, Chief Financial Officer (together, the “Grantees”). The PRSUs will generally vest 
upon achievement of a $70 Tiptree share price target (adjusted for dividends paid) prior to the tenth anniversary of the date of 
grant, subject to the Grantee’s continued employment with Tiptree. This special award reflects Tiptree’s desire for Messrs. 
Barnes,  Ilany,  Maultsby  and  McKinney  to  continue  to  lead  the  Company  for  a  further  significant  number  of  years  and  to 
create significant shareholder value over time.

On February 27, 2024, the Company’s board of directors declared a quarterly cash dividend of $0.06 per share to holders of 
common stock with a record date of March 11, 2024, and a payment date of March 18, 2024.

F-66

Item 9. Changes in and Disagreements with Accountants on Accounting and Financial Disclosure 

Not applicable. 

Item 9A. Controls and Procedures

(a)  Evaluation of Disclosure Controls and Procedures

The  Company’s  management,  with  the  participation  of  its  Executive  Chairman,  Chief  Executive  Officer  and  Chief 
Financial Officer, have evaluated the effectiveness of the design and operation of the Company’s disclosure controls and 
procedures (as defined in Rule 13a-15(e) or 15d-15(e) of the Exchange Act) as of December 31, 2023. Based upon that 
evaluation,  the  Company’s  Executive  Chairman,  Chief  Executive  Officer  and  Chief  Financial  Officer  have  concluded 
that the Company’s disclosure controls and procedures were effective as of December 31, 2023.

The  Company  is  committed  to  maintaining  a  strong  internal  control  environment  which  is  accompanied  by 
management’s  ongoing  focus  on  processes  and  related  controls  to  achieve  accurate  and  reliable  financial  reporting. 
However, all systems of internal control, no matter how well designed, have inherent limitations. Therefore, even those 
systems deemed to be effective can provide only reasonable assurance with respect to financial statement preparation and 
presentation. Projections of the effectiveness of internal control to future periods are subject to the risk that controls may 
become inadequate because of changes in conditions, or that the degree of compliance with the policies or procedures 
may deteriorate. 

(b)  Management’s Report on Internal Control over Financial Reporting

Management is responsible for establishing and maintaining adequate internal control over financial reporting, as such 
term is defined in Rule 13a-15(f) of the Exchange Act. The Company conducted an evaluation of the effectiveness of its 
internal  control  over  financial  reporting  based  upon  the  framework  established  in  the  Internal  Control  -  Integrated 
Framework (2013) issued by the Committee of Sponsoring Organizations of the Treadway Commission (“COSO”). 

Our internal control over financial reporting includes policies and procedures that pertain to the maintenance of records 
that,  in  reasonable  detail,  accurately  and  fairly  reflect  transactions  and  dispositions  of  assets;  provide  reasonable 
assurances that transactions are recorded as necessary to permit preparation of financial statements in accordance with 
U.S. generally accepted accounting principles, and that receipts and expenditures are made only in accordance with the 
authorization of management and the Board of Directors of the Company; and provide reasonable assurance regarding 
prevention or timely detection of unauthorized acquisition, use, or disposition of the Company’s assets that could have a 
material effect on our financial statements. 

If the Company identifies any material weaknesses, the COSO Framework does not allow the Company to conclude that 
our  internal  control  over  financial  reporting  is  effective.  A  material  weakness  is  a  deficiency,  or  combination  of 
deficiencies,  in  internal  control  over  financial  reporting,  such  that  there  is  a  reasonable  possibility  that  a  material 
misstatement of the Company’s annual or interim consolidated financial statements will not be prevented or detected on 
a timely basis.

Based  upon  its  assessment,  management  concluded  that  the  Company’s  internal  control  over  financial  reporting  as  of 
December 31, 2023 was effective using the COSO Framework.

The effectiveness of the Company’s internal control over financial reporting as of December 31, 2023 has been audited 
by Deloitte & Touche LLP, an independent registered public accounting firm that audited the Company’s consolidated 
financial statements as of and for the year ended December 31, 2023, as stated in their report, included in Item 8 of this 
Form 10-K, which expresses an unqualified opinion on the effectiveness of the Company’s internal control over financial 
reporting as of December 31, 2023.

(c)  Changes in Internal Control over Financial Reporting

67

There  were  no  changes  in  internal  control  over  financial  reporting  (as  such  term  is  defined  in  Rules  13a-15(f)  and 
15d-15(f) under the Exchange Act) during the twelve months ended December 31, 2023 that have materially affected, or 
are reasonably likely to materially affect, our internal control over financial reporting.

Item 9B. Other Information

None of the Company’s directors or officers adopted or terminated a Rule 10b5-1 trading arrangement or a non-Rule 10b5-1 
trading arrangement during the Company’s fiscal quarter ended December 31, 2023..

Item 9C. Disclosure Regarding Foreign Jurisdictions that Prevent Inspections.

Not applicable.

PART III

Item 10. Directors, Executive Officers and Corporate Governance 

Information  concerning  our  executive  officers  is  incorporated  herein  by  reference  to  information  included  in  the  Proxy 
Statement for the Company’s 2024 Annual Meeting of Stockholders. 

Information  with  respect  to  our  directors  and  the  nomination  process  is  incorporated  herein  by  reference  to  information 
included in the Proxy Statement for the Company’s 2024 Annual Meeting of Stockholders. 

Information regarding our audit committee and our audit committee financial experts is incorporated herein by reference to 
information included in the Proxy Statement for the Company’s 2024 Annual Meeting of Stockholders. 

Information required by Item 405 of Regulation S-K is incorporated herein by reference to information included in the Proxy 
Statement for the Company’s 2024 Annual Meeting of Stockholders.

Item 11. Executive Compensation

Information with respect to executive compensation is incorporated herein by reference to information included in the Proxy 
Statement for the Company’s 2024 Annual Meeting of Stockholders.

Item 12. Security Ownership of Certain Beneficial Owners and Management and Related Stockholder Matters 

Information  with  respect  to  security  ownership  of  certain  beneficial  owners  and  management  is  incorporated  herein  by 
reference to information included in the Proxy Statement for the Company’s 2024 Annual Meeting of Stockholders.

Item 13. Certain Relationships and Related Transactions, and Director Independence 

Information  with  respect  to  such  contractual  relationships  and  independence  is  incorporated  herein  by  reference  to  the 
information in the Proxy Statement for the Company’s 2024 Annual Meeting of Stockholders. 

Item 14. Principal Accountant Fees and Services 

Information  with  respect  to  principal  accounting  fees  and  services  and  pre-approval  policies  are  incorporated  herein  by 
reference to information included in the Proxy Statement for the Company’s 2024 Annual Meeting of Stockholders. 

68

PART IV
Item 15. Exhibits, Financial Statement Schedules 

The following documents are filed as a part of this Form 10-K:
(a)(1) All Financial Statements

Index to Financial Statements:
Consolidated Balance Sheets as of December 31, 2023 and 2022
Consolidated Statements of Operations for the years ended December 31, 2023, 2022 and 2021
Consolidated Statements of Comprehensive Income (Loss) for the years ended December 31, 2023, 
2022 and 2021
Consolidated  Statements  of  Changes  in  Stockholders’  Equity  for  the  years  ended  December  31, 
2023, 2022 and 2021
Consolidated Statements of Cash Flows for the years ended December 31, 2023, 2022 and 2021
Notes to Consolidated Financial Statements 

Page
F- 5
F- 6

F- 7

F- 8
F- 10
F- 12

(a)(2) Financial Statement Schedules

Schedule II—“Financial Information of Registrant”, is filed as part of this Annual Report on Form 10-K and should be read 
in conjunction with the financial statements and notes thereto contained in Item 8—“Financial Statements and Supplementary 
Data.”

All  other  financial  statements  and  financial  statement  schedules  for  which  provision  is  made  in  the  applicable  accounting 
regulations  of  the  SEC  are  not  required  under  the  related  instruction,  are  not  material  or  are  not  applicable  and,  therefore, 
have been omitted. 

(a)(3) Exhibits

Exhibit 
No.

Description

3.1

3.2

3.3

4.1

4.2

10.1

10.2

10.3

10.4

Fifth Articles of Amendment and Restatement of the Registrant, effective June 6, 2018 (previously filed as 
Exhibit 3.1 to the Registrant’s Current Report on Form 8-K (File No. 001-33549), filed on June 7, 2018 and 
herein incorporated by reference).

Fifth Amended and Restated Bylaws of the Registrant (previously filed as Exhibit 3.1 to the Registrant’s 
Current Report on Form 8-K (File No. 001-33549), filed on January 25, 2023 and herein incorporated by 
reference).

Articles Supplementary of the Registrant, dated December 29, 2014 (previously filed as Exhibit 3.1 to the 
Registrant’s Current Report on Form 8-K (File No. 001-33549), filed on December 29, 2014 and herein 
incorporated by reference).
Form of Certificate of Common Stock (previously filed as Exhibit 4.1 to the Registrant’s Current Report on 
Form 8-A/A (File No. 001-33549), filed on June 7, 2018 and herein incorporated by reference.

Description of the Registrant’s Securities Registered under Section 12 of the Securities Exchange Act of 1934 
(previously filed as Exhibit 4.3 to the Registrant’s Annual Report on Form 10-K (File No. 001-33549), filed on 
March 12, 2020 and herein incorporated by reference).

Registrant’s 2017 Omnibus Incentive Plan (previously filed as Exhibit 10.1 to the Registrant’s Form S-8 
Registration Statement (File No. 333-218827), filed on June 19, 2017 and herein incorporated by reference).**
Amendment No. 1 to 2017 Omnibus Incentive Plan (previously filed as Annex A to the Registrant’s Proxy 
Statement for the 2022 Annual Meeting of Shareholders (File No. 001-33549), and herein incorporated by 
reference).**

Form of Non-Qualified Stock Option Agreement under the Registrant’s 2017 Omnibus Incentive Plan 
(previously filed as Exhibit 10.3 to the Registrant’s Annual Report on Form 10-K (File No. 001-33549), filed 
on March 14, 2018 and herein incorporated by reference)**

Form of Non-Qualified Stock Option Agreement under the Registrant’s 2017 Omnibus Incentive Plan) 
(previously filed as Exhibit 10.5 to the Registrant’s Annual Report on Form 10-K (File No. 001-33549), filed 
on March 12, 2020 and herein incorporated by reference).**

69

 
 
Exhibit 
No.

10.5

10.6

10.7

10.8

10.9

10.10

10.11

10.12

10.13

10.14

10.15

10.16

10.17

10.18

10.19

10.20

10.21

10.22

10.23

Description
Form of Restricted Stock Unit Agreement under the Registrant’s 2017 Omnibus Incentive Plan (previously 
filed as Exhibit 10.6 to the Registrant’s Annual Report on Form 10-K (File No. 001-33549), filed on March 12, 
2020 and herein incorporated by reference).**
Form of Restricted Stock Unit Agreement under the Registrant’s 2017 Omnibus Incentive Plan (previously 
filed as Exhibit 10.7 to the Registrant’s Annual Report on Form 10-K (File No. 001-33549), filed on March 12, 
2020 and herein incorporated by reference).**
Form of Restricted Stock Unit Agreement under the Registrant’s 2017 Omnibus Incentive Plan (2024 Form) 
(filed herewith).**
Form of Performance Restricted Stock Unit Agreement (previously filed as Exhibit 10.1 to the Registrant’s 
Quarterly Report on Form 10-Q (File No. 001-33549), filed on August 8, 2022 and herein incorporated by 
reference).**
Form of Performance Restricted Stock Unit Agreement under the Registrant’s 2017 Omnibus Incentive Plan 
(2024 Form) (filed herewith).** 
Form of Indemnification Agreement (previously filed as Exhibit 10.9 to the Registrant’s Registration Statement 
on Form S-11, as amended (File No. 333-141634), filed on June 7, 2007 and herein incorporated by reference).
Tiptree Inc. 2023 Deferred Compensation Plan (previously filed as Exhibit 10.1 to the Registrant’s Quarterly 
Report on Form 10-Q (File No. 001-33549), filed on August 2, 2023 and herein incorporated by reference).**
Amended and Restated Transition Services Agreement between Tricadia Holdings, L.P. and Tiptree Inc., dated 
as of February 15, 2019 (previously filed as Exhibit 10.2 to the Registrant’s Current Report on Form 8-K (File 
No. 001-33549), filed on April 22, 2019 and herein incorporated by reference).
Second Amended and Restated Credit Agreement, dated as of October 21, 2022 by and among Fortegra 
Financial Corporation, LOTS Intermediate Co. and The Fortegra Group, Inc., as borrowers, the lenders from 
time to time party thereto, certain of Fortegra’s subsidiaries, as guarantors, and Fifth Third Bank, NA, as the 
administrative agent and issuing lender (previously filed as Exhibit 10.1 to Form 8-K (File No. 001-33549), 
filed October 25, 2022 and herein incorporated by reference).
Second Amendment to Credit Agreement, dated as of January 31, 2023, by and among South Bay Acceptance 
Corporation, South Bay Funding LLC, the lenders from time to time party thereto and Fifth Third Bank, 
National Association as the administrative agent (previously filed as Exhibit 10.11 to the Registrant’s Annual 
Report on Form 10-K (File No. 001-33549) filed on March 8, 2023 and herein incorporated by reference).
Amended and Restated Credit Agreement dated as of October 6, 2023 by and among South Bay Acceptance 
Corporation, South Bay Funding LLC, the lenders from time to time party thereto and Fifth Third Bank, 
National Association as the administrative agent (previously filed as Exhibit 10.1 to the Registrant’s Current 
Report on Form 8-K (File No. 001-33549), filed on October 11, 2023 and herein incorporated by reference.
Equity Interest Purchase Agreement, dated December 16, 2019, by and among Tiptree Warranty Holdings, LLC 
and Peter Masi (previously filed as Exhibit 10.1 to the Registrant’s Current Report on Form 8-K (File No. 
001-33549), filed on December 17, 2019 and herein incorporated by reference).
First Amendment to the Equity Interest Purchase Agreement, effective November 3, 2021, by and among 
Fortegra Warranty Holdings, LLC and Peter Masi (previously filed as Exhibit 10.1 to the Registrant’s Quarterly 
Report on Form 10-Q (File No. 001-33549) filed on November 3, 2021 and herein incorporated by reference).
Amendment No. 5 to Partner Emeritus Agreement, effective December 1, 2023, by and between Tiptree Inc. 
and Arif Inayatullah (filed herewith).
Stockholders Agreement between and among Tiptree Holdings LLC, The Fortegra Group Inc. and WP Falcon 
Aggregator, L.P. (previously filed as Exhibit 10.5 to the Registrant’s Current Report on Form 8-K (File No. 
001-33549) filed on June 21, 2022 and herein incorporated by reference).
Warrant to Purchase Common Stock (previously filed as Exhibit 10.1 to the Registrant’s Current Report on 
Form 8-K (File No. 001-33549) filed on June 21, 2022 and herein incorporated by reference).
Investor Additional Warrants to Purchase Common Stock (previously filed as Exhibit 10.2 to the Registrant’s 
Current Report on Form 8-K (File No. 001-33549) filed on June 21, 2022 and herein incorporated by 
reference).
Tiptree Additional Warrants to Purchase Common Stock (previously filed as Exhibit 10.3 to the Registrant’s 
Current Report on Form 8-K (File No. 001-33549) filed on June 21, 2022 and herein incorporated by 
reference).
Certificate of Designation of Series A Preferred Stock (previously filed as Exhibit 10.4 to the Registrant’s 
Current Report on Form 8-K (File No. 001-33549) filed on June 21, 2022 and herein incorporated by 
reference).

70

Exhibit 
No.

10.24

10.25

10.26

10.27

21.1
23.1

31.1

31.2

31.3

32.1

32.2

32.3

97

Description
Registration Rights Agreement between and among Tiptree Holdings LLC, The Fortegra Group Inc., WP 
Falcon Aggregator, L.P. and the other holders set forth therein (previously filed as Exhibit 10.6 to the 
Registrant’s Current Report on Form 8-K (File No. 001-33549) filed on June 21, 2022 and herein incorporated 
by reference).
Investment Advisory Agreement by and among Tiptree Inc., The Fortegra Group, LLC and subsidiaries and 
Corvid Peak Capital Management, LLC effective as of May 3, 2021 and July 1, 2021 (previously filed as 
Exhibit 10.1 to the Registrant’s Quarterly Report on Form 10-Q (File No. 001-33549) filed on August 4, 2021 
and herein incorporated by reference).
Amended and Restated Executive Separation and Transition Agreement by and among Tiptree Inc. and Sandra 
Bell, dated as of February 28, 2023 (previously filed as Exhibit 10.24 to the Registrant’s Annual Report on 
Form 10-K (File No. 001-33549) filed on March 8, 2023 and herein incorporated by reference).**
Executive Employment Agreement by and among Tiptree Inc. and Scott McKinney, dated as of October 14, 
2022 (previously filed as Exhibit 10.2 to the Registrant’s Current Report on Form 8-K (File No. 001-33549), 
filed on October 17, 2022 and herein incorporated by reference).**
Subsidiaries of the Registrant (filed herewith).
Consent of Independent Registered Public Accounting Firm (filed herewith).
Certification  of  Executive  Chairman  pursuant  to  Section  302  of  the  Sarbanes-Oxley  Act  of  2002  (filed 
herewith).
Certification  of  Chief  Executive  Officer  pursuant  to  Section  302  of  the  Sarbanes-Oxley  Act  of  2002  (filed 
herewith).
Certification  of  Chief  Financial  Officer  pursuant  to  Section  302  of  the  Sarbanes-Oxley  Act  of  2002  (filed 
herewith).
Certification  of  Executive  Chairman  pursuant  to  Section  906  of  the  Sarbanes-Oxley  Act  of  2002  (furnished 
herewith).
Certification of Chief Executive Officer pursuant to Section 906 of the Sarbanes-Oxley Act of 2002 (furnished 
herewith).
Certification of Chief Financial Officer pursuant to Section 906 of the Sarbanes-Oxley Act of 2002 (furnished 
herewith).
Policy for Recoupment of Incentive Compensation (filed herewith).**

101.INS XBRL Instance Document*
101.SCH  XBRL Taxonomy Extension Schema Document*
101.CAL XBRL Taxonomy Extension Calculation Linkbase Document*
101.LAB XBRL Taxonomy Extension Label Linkbase Document*
101.PRE XBRL Taxonomy Extension Presentation Linkbase Document*
101.DEF XBRL Taxonomy Extension Definition Linkbase Document*

104

Cover Page Interactive Data File (embedded within the iXBRL document and included in Exhibit 101).

* Attached as Exhibit 101 to this Annual Report on Form 10-K are the following materials, formatted in XBRL (eXtensible 
Business  Reporting  Language):  (i)  the  Consolidated  Balance  Sheets  (audited)  for  December  31,  2023  and  2022,  (ii)  the 
Consolidated  Statements  of  Operations  (audited)  for  the  years  ended  December  31,  2023,  2022  and  2021,  (iii)  the 
Consolidated Statements of Comprehensive Income (Loss) (audited) for the years ended December 31, 2023, 2022 and 2021, 
(iv) the Consolidated Statements of Changes in Stockholders’ Equity (audited) for the years ended December 31, 2023, 2022 
and 2021, (v) the Consolidated Statements of Cash Flows (audited) for the years ended December 31, 2023, 2022 and 2021 
and (vi) the Notes to the Consolidated Financial Statements (audited). 

** Denotes a management contract or compensatory plan, contract or arrangement.

Item 16. Form 10-K Summary

None. 

71

SIGNATURES

Pursuant to the requirements of Section 13 or 15(d) of the Securities Exchange Act of 1934, Tiptree Inc. has duly caused this 
Report to be signed on its behalf by the undersigned, thereunto duly authorized.

Date: 

February 29, 2024

Tiptree Inc.

By:/s/ Jonathan Ilany

Jonathan Ilany

Chief Executive Officer

Pursuant to the requirements of the Securities Exchange Act of 1934, this Report has been signed by the following persons on 
behalf of the Registrant and in the capacities and on the dates indicated:

Signature

Title

Date

/s/ Jonathan Ilany
Jonathan Ilany

/s/ Scott McKinney
Scott McKinney

/s/ Michael G. Barnes
Michael G. Barnes

/s/ Randy S. Maultsby
Randy S. Maultsby

/s/ Paul M. Friedman
Paul M. Friedman

/s/ Lesley Goldwasser 
Lesley Goldwasser

/s/ Bradley E. Smith
Bradley E. Smith

/s/ Dominique Mielle
Dominique Mielle

Chief Executive Officer and 

Director                               

February 29, 2024

(Principal Executive Officer)

Chief Financial Officer         

(Principal Financial Officer and
Principal Accounting Officer)

February 29, 2024

Executive Chairman and Director

February 29, 2024

President and Director

February 29, 2024

February 29, 2024

February 29, 2024

February 29, 2024

February 29, 2024

Director

Director

Director

Director

72

 
 
 
 
Schedule II — Financial Information of Registrant

TIPTREE INC.
PARENT COMPANY ONLY STATEMENTS OF INCOME

(All amounts in thousands)

Revenues

Net realized and unrealized gains (losses)
Interest income
Other revenue
Total revenues

Expenses

Employee compensation and benefits
Interest expense (1)
Professional fees
Rent and facilities
General and administrative
Depreciation and amortization
Other expenses
Total expenses

$ 

Equity in earnings (losses) of subsidiaries, net of tax (1)
Income (loss) before taxes

Less: provision (benefit) for income taxes

Net income (loss) attributable to Tiptree Inc. common stockholders

$ 

(1)      Eliminated in consolidation.

TIPTREE INC.
PARENT COMPANY ONLY BALANCE SHEETS

(All amounts in thousands, except share data)

Assets

Investment in subsidiaries (1)
Cash and cash equivalents
Available for sale securities, at fair value
Equity securities
Notes and accounts receivable, net
Income taxes receivable
Deferred tax assets
Right of use assets - operating leases
Other assets
Total assets

Liabilities and Stockholders’ Equity
Liabilities

Operating lease liability
Intercompany payables, net (1)
Accrued expenses
Total liabilities

Stockholders' Equity

Preferred stock: $0.001 par value, 100,000,000 shares authorized, none issued or outstanding
Common stock: $0.001 par value, 200,000,000 shares authorized, 36,756,187 and 36,385,299 shares issued 
and outstanding, respectively
Additional paid-in capital
Accumulated other comprehensive income (loss), net of tax
Retained earnings
Total stockholders’ equity
Total liabilities and stockholders' equity

(1)      Eliminated in consolidation.

73

For the Year Ended December 31,
2022

2021

2023

6,126  $ 
4,522 
302 
10,950 

30,115 
163 
4,511 
2,003 
868 
1,327 
1,390 
40,377 
40,386 
10,959 
(2,992) 
13,951  $ 

—  $ 
277 
4 
281 

27,188 
123 
6,532 
3,126 
755 
805 
1,675 
40,204 
24,778 
(15,145) 
(6,871) 
(8,274)  $ 

— 
259 
67 
326 

28,060 
— 
6,656 
1,993 
1,254 
805 
1,305 
40,073 
73,164 
33,417 
(4,715) 
38,132 

As of December 31,
2022
2023

304,866  $ 
45,098 
30,475 
37,753 
2,124 
304 
22,636 
12,021 
12,338 
467,615  $ 

293,050 
126,111 
— 
— 
3,300 
15,956 
17,571 
13,570 
8,768 
478,326 

15,829  $ 
16,865 
18,055 
50,749  $ 

18,079 
48,186 
14,696 
80,961 

—  $ 

— 

37 
382,239 
(26,073) 
60,663 
416,866 
467,615  $ 

36 
382,645 
(39,429) 
54,113 
397,365 
478,326 

$ 

$ 

$ 

$ 

$ 

$ 

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC.
PARENT COMPANY ONLY STATEMENTS OF CASH FLOWS

(All amounts in thousands)

Operating Activities:
Net income (loss) attributable to Tiptree Inc. common stockholders
Adjustments to reconcile net income to net cash provided by operating activities

Equity in earnings of subsidiaries(1)
Net realized and unrealized (gains) losses 
Amortization/accretion of premiums and discounts
Depreciation expense
Deferred provision (benefit) for income taxes
Non-cash lease expense
Non-cash compensation expense
Net changes in other operating assets and liabilities

Net cash provided by (used in) operating activities

Investing Activities:

Purchases of investments
Proceeds from sales and maturities of investments
Proceeds from the sale of businesses
Proceeds from notes receivable
Issuance of notes receivable

Net cash flows provided by (used in) provided by investing activities

Financing Activities:
Distributions from subsidiaries (1)
Proceeds from intercompany notes payable (1)
Repayment of intercompany notes payable (1)
Cash received for the exercise of warrants
Dividends paid
Repurchases of common stock
Subsidiary RSU exchanges
Cash paid in connection with the vesting of units

Net cash provided by (used in) financing activities
Net increase (decrease) in cash and cash equivalents
Cash and cash equivalents at beginning of period
Cash and cash equivalents at end of period

Cash (received) paid for income taxes

(1)      Eliminated in consolidation.

Note 1. Basis of Presentation 

For the Year Ended December 31,
2022

2021

2023

$ 

13,951  $ 

(8,274)  $ 

38,132 

(40,386) 
(6,126) 
(1,899) 
1,327 
(5,453) 
1,970 
5,845 
13,032 
(17,739) 

(149,309) 
90,811 
— 
— 
— 
(58,498) 

(24,778) 
— 
— 
805 
1,048 
2,512 
7,093 
(4,054) 
(25,648) 

— 
— 
— 
— 
— 
— 

35,906 
— 
(33,281) 
— 
(7,401) 
— 
— 
— 
(4,776) 
(81,013) 
126,111 
45,098  $ 

99,965 
43,281 
— 
13,724 
(5,759) 
(1,727) 
(181) 
— 
149,303 
123,655 
2,456 
126,111  $ 

(73,164) 
— 
— 
805 
(528) 
1,843 
8,580 
5,412 
(18,920) 

— 
— 
125 
169 
(432) 
(138) 

30,996 
— 
— 
— 
(5,409) 
(2,882) 
(1,458) 
(445) 
20,802 
1,744 
712 
2,456 

(15,708)  $ 

(155)  $ 

61 

$ 

$ 

Tiptree Inc. (together with its consolidated subsidiaries, collectively, Tiptree, the Company, or we) is a Maryland Corporation that 
was  incorporated  on  March  19,  2007.  Tiptree’s  common  stock  trades  on  the  Nasdaq  Capital  Market  under  the  symbol  “TIPT”. 
Tiptree is a holding company that combines specialty insurance operations with investment management capabilities. We allocate 
our  capital  across  our  insurance  operations  and  other  investments.  We  classify  our  business  into  two  reportable  segments: 
Insurance  and  Mortgage.  We  refer  to  our  non-insurance  operations,  assets  and  other  investments,  which  is  comprised  of  our 
Mortgage reportable segment and our non-reportable segments and other business activities, as Tiptree Capital. 

Pursuant  to  the  terms  discussed  in  Note—(11)  Debt,  net  in  the  notes  to  consolidated  financial  statements,  indebtedness  of 
subsidiaries of Tiptree limits that subsidiary’s ability to pay dividends or make distribution to Tiptree Inc. In addition, certain other 
subsidiaries’ activities are regulated, or subject to specific restriction on transfers as a result of financing arrangements. As a result 
of these restrictions, these financial statements of the Registrant have been prepared in accordance with Rule 12-04 of Regulation 
S-X, as restricted net assets of the Company's subsidiaries (as defined in Rule 4-08(e)(3) of Regulation S-X) exceed 25% of the 
Company's consolidated net assets as of December 31, 2023. 

These financial statements have been prepared on a "parent-only" basis. Under a parent-only presentation, the Parent Company's 
investments  in  subsidiaries  are  presented  under  the  equity  method  of  accounting.  Certain  information  and  footnote  disclosures 

74

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
  
normally included in financial statements prepared in accordance with GAAP have been or omitted. The accompanying financial 
information should be read in conjunction with the Tiptree Inc. consolidated financial statements and related Notes thereto.

Note 2. Dividends Received

The  Company  received  distributions  of  $35,906,  $99,965  and  $30,996  for  the  years  ended  December  31,  2023,  2022  and  2021, 
respectively.

75