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Tiptree Inc.

tipt · NASDAQ Financial Services
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Ticker tipt
Exchange NASDAQ
Sector Financial Services
Industry Insurance - Specialty
Employees 1496
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FY2021 Annual Report · Tiptree Inc.
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2021 

Annual Report to Shareholders 

April 22, 2022 

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
To Our Fellow Shareholders, 

2021 proved to be one of the best years for Tiptree since its founding in June 2007. Tiptree’s share 
price appreciation plus dividends for the year produced a total return for shareholders of 178.7%. 
Revenues for the year increased to $1.2 billion, up 48.2% from the prior year, and adjusted net 
income increased to $63.9 million, up 24.2%, a record year for both metrics. 

All of Tiptree’s cornerstone businesses were profitable in 2021. Under the guidance of Fortegra’s 
CEO Rick Kahlbaugh and his team, our specialty insurance business, the Fortegra Group, continued 
to build upon its exceptional multi-year track record, producing a record adjusted return on equity of 
22% while growing top-line premiums at 32% for the year. 

Our businesses in Tiptree Capital also performed well in 2021, with a combined return on average 
equity of 22.2%. Our ownership of Reliance First Capital, which originates and services residential 
mortgages, as well as Tiptree Marine, which holds our various shipping interests, reported excellent 
results for the year, benefiting from favorable market conditions as interest rates remained low and 
global economies continued their recovery from the depths of the Covid-19 pandemic. Also, in spite of 
our significant share-price appreciation, we were able to buy back 528,662 shares of Tiptree at a 
weighted average price of $5.45, a substantial discount to our intrinsic value. 

In summary, we were very pleased with Tiptree’s results for 2021, and believe there is a clear path to 
continued growth in the coming years. 

Our consolidated results for 2021 are summarized below: 

TIPTREE CONSOLIDATED RESULTS 

GAAP FINANCIAL HIGHLIGHTS 
(dollars in millions, except per share data) 

2021 

2020 

2019 

2018 

2017 

Net income attributable to Common Stockholders 
Diluted earnings per Common Share 
Cash dividends paid per share 

38.1 
1.09 
0.16 

(29.2) 
(0.86) 
0.16 

18.4 
0.50 
0.155 

23.9 
0.69 
0.135 

3.6 
0.11 
0.12 

Total assets 
Total investments and cash and cash equivalents  1,165.9 
393.3 
Debt, net 
400.2 
Total stockholders’ equity 

3,599.1  2,995.8  2,198.3  1,864.9  1,989.7 
636.0 
870.1 
346.1 
374.5 
396.8 
411.4 

948.3 
366.2 
373.5 

782.9 
354.1 
399.3 

NON-GAAP FINANCIAL HIGHLIGHTS1 

2021 

2020 

2019 

2018 

2017 

Adjusted EBITDA 
Adjusted Net Income 
Shares outstanding2 
Book Value per share2 
Total cash returned to shareholders 

100.8 
63.9 
34.1 
11.22 
8.2 

4.5 
54.1 
32.7 
10.90 
19.3 

68.1 
27.6 
34.6 
11.52 
14.4 

26.7 
22.3 
35.9 
10.79 
19.1 

38.4 
21.4 
37.9 
9.97 
11.8 

1 For a reconciliation to GAAP financials, see “Non-GAAP Measures” beginning on p. 66 of the attached Form 10-K. Combined ratio has 
been adjusted for impacts of purchase price accounting amortization for 2014-2017. 
2 For periods prior to April 10, 2018, book value per share assumes the full exchange of the limited partner units of TFP for Common Stock. 
1 

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
INSURANCE 

Our largest business, The Fortegra Group, is focused on providing niche and specialty insurance 
coverages which are generally underserved or require specialized product knowledge. We prioritize 
high frequency contracts which experience low severity claims activity and have limited exposure to 
catastrophic events. As previously mentioned, Fortegra’s core operations continued to grow in 2021, 
with gross written premiums and premium equivalents increasing 32% for the year driven by growth in 
U.S. specialty insurance lines and service contract businesses in U.S. and Europe. As a function of 
Fortegra’s premium growth, the combination of unearned premiums and deferred revenues on the 
balance sheet grew to $1,658.8 million, up $399.1 million, or 32%, from the prior year-end, providing a 
solid and stable base to Fortegra’s future earnings. In addition, Fortegra’s investment portfolio grew 
by 28% to $910 million, the bulk of which is now managed by Tiptree’s affiliate Corvid Peak Capital 
Management. Importantly, Fortegra’s combined ratio improved to an impressive 90.6% for the year, 
demonstrating Fortegra’s ability to continue to grow profitably. 

On October 12, 2021, Tiptree announced a $200 million investment in Fortegra from Warburg Pincus, 
which upon closing will result in an approximate 24% ownership of the business on an as converted 
basis. As we progress through the regulatory approval process, which we anticipate will be completed 
in the second quarter of this year, we are looking forward to working closely with Warburg’s team of 
seasoned professionals and welcome their partnership in guiding Fortegra’s continued growth. 

TIPTREE CAPITAL 

Tiptree Capital has invested in a broad range of businesses over the years, but currently holds three 
primary investments: 1) Reliance First Capital, a residential mortgage originator and servicer, 2)  
Tiptree Marine, which holds our interests in shipping related investments, and 3) publicly listed shares 
representing an approximately 30% ownership interest in Invesque Inc., a real estate investment 
company which focuses on senior living and health care related properties. For 2021, all three of 
Tiptree Capital’s primary investments were profitable, generating an aggregate pretax income of 
$45.6 million, driven by continued strong performance in our mortgage operations and significant 
appreciation of dry bulk shipping rates. Although 2021 was unquestionably a very favorable 
environment for our primary areas of focus, we will continue to look for ways to optimize our 
investments held at Tiptree Capital with the objective of generating “all-weather” absolute returns that 
exceed other available equity investment opportunities. With no set holding period objective, and no 
risk of redemption on our capital, we believe we have a distinct advantage over hedge funds or private 
equity, and are able to take a very long-term view on our outlook for returns. 

LOOKING AHEAD 

2021 was an exceptional year, with all of our major businesses performing well. Although we certainly 
experienced benefits from a market recovering from the pandemic, it may also be directly attributed to 
the hard work and expertise of Tiptree’s team of professionals and those of our related companies. 
We could not be more excited for Tiptree’s future and we are confident in the long-term outlook of the 
company. 

We welcome any and all questions and suggestions 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, 2021
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.)

299 Park Avenue

13th Floor New York New York  

(Address of Principal Executive Offices)

10171
(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 if disclosure of delinquent filers pursuant to Item 405 of Regulation S-K (§ 229.405) is not contained herein, and will not be contained, to the 
best of registrant’s knowledge, in definitive proxy or information statements incorporated by reference in Part III of this Form 10-K or any amendment to this Form 10-
K.  ¨

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 is a shell company (as defined in Rule 12b-2 of the Exchange Act.)   Yes ☐     No ☒ 

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. 
☒

As of June 30, 2021, 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 $226,808,986, based upon the closing sales price of $9.30 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 March 7, 2022, there were 34,385,602 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 2022  Annual 
Meeting of Stockholders is incorporated by reference into Part III.    

 
 
 
 
  
	
	
	
	
	
	
	
	
 
 
 
 
 
 
 
 
TIPTREE INC.
Annual Report on Form 10-K
December 31, 2021
Table of Contents

ITEM
PART I 
Item 1. Business
Item 1A. Risk Factors
Item 1B. Unresolved Staff Comments
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

Consolidated Balance Sheets for December 31, 2021 and 2020
Consolidated Statements of Operations for the three years ended December 31, 2021, 2020 and 2019
Consolidated Statements of Comprehensive Income (Loss) for the three years ended December 31, 2021, 2020 and 2019
Consolidated Statement of Changes in Stockholders’ Equity for the three years ended December 31, 2021, 2020 and 2019
Consolidated Statements of Cash Flows for the three years ended December 31, 2021, 2020 and 2019
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) 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
Item 12. Security Ownership of Certain Beneficial Owners and Management and Related Stockholder Matters
Item 13. Certain Relationships and Related Transactions, and Director Independence

2

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TIPTREE INC.
Annual Report on Form 10-K
December 31, 2021
Table of Contents

ITEM
Item 14. Principal Accountant Fees and Services
PART IV
Item 15. Exhibits, Financial Statement Schedules
Item 16. Form 10-K Summary
Signatures

Page Number
57
58
58
61
62

3

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, the closing of the transaction with Warburg Pincus, 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.”

4

 
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.

•

•

•

•

•

Failure to consummate the proposed WP Transaction could have a material adverse impact on our business.

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 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 or new products and services 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.

5

•

•

•

•

•

•

•

•

•

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  protect  our  insurance  subsidiaries’  intellectual  property  rights  could  impair  their  intellectual  property, 
technology platform and brand. In addition, they may be sued for alleged infringement of their proprietary rights.

Our  insurance  subsidiaries  employ  third-party  licensed  software  for  use  in  their  business,  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.

A significant decrease of the market values of our vessels could cause us to incur impairment losses.

Our vessels may suffer damage and we may face unexpected drydocking costs.

The operation of dry bulk vessels and product tankers has certain unique operational risks, including piracy.

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, 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.

• 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. 

6

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. 
“CFPB” means the Consumer Financial Protection Bureau. 
“CLOs” means collateralized loan obligations.
“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.
“Defend” means Defend Insurance Group. 
“Dodd-Frank Act” means the Dodd-Frank Wall Street Reform and Consumer Protection Act. 
“EBITDA” means earnings before interest, taxes, depreciation and amortization. 
“E&S” means excess and surplus. 
“EU” means European Union. 
“Exchange Act” means the Securities Exchange Act of 1934, as amended.
“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. 
“Fortegra” or “The Fortegra Group” means The Fortegra Group, LLC.
“Fortegra Financial” means Fortegra Financial Corporation.
“Fortegra Warranty” mean Fortegra Warranty Holdings, LLC.
“GAAP” means U.S. generally accepted accounting principles. 
“GSE” means government-sponsored enterprise.
“Invesque” means Invesque Inc.
“Luxury” or “Luxury Mortgage” means Luxury Mortgage Corp.
“MGAs” means managing general agents. 
“NAIC” means the National Association of Insurance Commissioners.
“Operating Company” means Tiptree Operating Company, LLC.
“Reliance” means Reliance First Capital, LLC. 
“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.
“Tiptree”, the “Company”, “we”, “its”, “us” and “our” means, unless otherwise indicated by the context, Tiptree Inc. and its 
consolidated subsidiaries.
“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.
“WP Transaction” means the $200 million strategic investment in Fortegra by Warburg Pincus pursuant to the Securities Purchase 
Agreement between and among Tiptree, Fortegra and WP Falcon Aggregator, L.P. dated October 11, 2021. 

7

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 shareholders since 2007.

We categorize our businesses into: Insurance and Tiptree Capital. 

Insurance:  Our  Insurance  segment  is  a  group  of  companies  operating  as  part  of  The  Fortegra  Group  (“Fortegra”),  which  is  a 
leading  provider  of  specialty  insurance  products  and  related  services.  Fortegra  designs,  markets  and  underwrites  specialty 
commercial  and  personal  property  and  casualty  insurance  products  incorporating  value-added  coverages  and  services  for  select 
target  markets  or  niches.  We  target  markets  with  specialized  areas  of  demand,  including  smaller  niche  lines,  and  by  offering 
innovative policy features. We believe this approach allows us to compete by offering customized coverage and solutions, rather 
than competing solely on price. Our products are distributed through a diverse multi-channel delivery system centered around our 
production  underwriting  organization  and  large  independent  agent  network.  We  use  proprietary  technology  to  efficiently  and 
effectively administer business to specialty markets that we believe are underserved by larger, less agile insurers. Our underwriting 
expertise,  strong  agent  relationships  and  proprietary  technology  empower  us  to  remain  agile  and  take  advantage  of  attractive 
opportunities.

Tiptree  Capital:  We  own  a  diversified  group  of  businesses  and  investments  that  are  owned  and  managed  separately  as  Tiptree 
Capital, and 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 origination operations, maritime 
shipping operations and investments in shares of Invesque.

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 
shareholder  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  shareholders.  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  March  7, 
2022, directors, officers, employees and related trusts owned 32% of the Company. 

As  of  December  31,  2021,  Tiptree  and  its  consolidated  subsidiaries  had  1,472  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.”

8

 
 
Insurance 

Overview

Fortegra is an established, growing and consistently profitable specialty insurer. We focus on niche business lines and fee-oriented 
services,  providing  us  with  a  unique  combination  of  insurance,  service  contract  products  and  related  service  solutions.  Our 
vertically integrated business model creates an attractive blend of traditional underwriting revenues, unregulated fee revenues and 
investment  income.  This  differentiated  approach  has  led  to  robust  growth,  consistent  profitability  and  high  cash  flows.  The 
business was founded in 1978 and is headquartered in Jacksonville, Florida. 

We target lines of business with lower risk limits and use risk mitigation to limit both aggregation and catastrophic exposures. We 
believe  this  focus  has  allowed  us  to  produce  superior  underwriting  results  through  a  more  granular  spread  of  risk.  We  use 
proprietary  technology  to  efficiently  and  effectively  administer  business  to  specialty  markets  that  we  feel  are  underserved  by 
larger, less agile insurers. Our underwriting expertise, strong distribution relationships and proprietary technology empower us to 
remain agile and take advantage of attractive opportunities in all market conditions.

We use an agent-focused distribution model, employing a “one-to-many” strategy, which allows us to leverage our high-quality 
partners and their customer bases. We deliver our insurance products through independent insurance agents. We also partner with 
agents that are embedded in consumer finance companies, online and regional big box retailers, auto dealers and other companies 
to deliver our products that complement retail and consumer purchases. We use artificial intelligence (“A.I.”) technology to create 
a distinct lead generation advantage for our insurance distribution partners and over the past five years have maintained a greater 
than  95%  persistency  rate,  which  represents  the  annual  retention  of  the  number  of  our  producing  agents.  We  align  our  agents’ 
economics  with  their  underwriting  results  via  risk-sharing  agreements,  which  we  believe  has  enabled  us  to  better  manage 
uncertainties  and  deliver  more  consistent  profit  margins.  Combined  with  our  underwriting  expertise  and  technology-enabled 
administration, we provide a high-value proposition to our distribution relationships.

Products and Services

U.S. Insurance: Provides niche, specialty insurance products distributed through managing general agents (“MGAs”), wholesale 
agents, retail agents and brokers. We offer an array of commercial programs with a particular focus on casualty lines. These lines 
include  professional  liability,  contractual  liability,  energy,  allied  health,  general  liability,  directors  and  officers  liability,  life 
sciences, inland marine, contractors equipment, contractors liability, student legal liability, hospitality and business owner policy. 
We also offer a range of personal lines programs including storage unit contents, manufactured housing, GAP, auto, credit life and 
disability and collateral insurance products. Additionally, we offer related fee-earning, unregulated products and services, such as 
captive administration services, program administration and premium financing, to our U.S. Insurance customers. We are active in 
50 states in the United States.

•

•

Commercial Lines: Our business is focused on underwriting specialty commercial insurance coverages for agents, retail 
agents, MGAs, brokers and other program managers that require broad licensure, an “A-” or better A.M. Best rating, and 
specialized knowledge and expertise to deliver our products. Our commercial lines include a wide array of niche products, 
including admitted and excess and surplus (“E&S”) lines. With each program, we grant agents and program managers the 
authority to produce, underwrite and administer policies subject to our pricing and underwriting guidelines. We typically 
transfer  a  substantial  portion  of  the  underwriting  risk  to  third-party  reinsurers  for  which  we  are  paid  a  ceding  fee.  We 
generally retain between 40-60% of the premium on a net basis.

Personal Lines: Our personal lines offer a diverse set of specialty products including credit insurance, collateral insurance, 
non-standard auto and other niche personal lines. Credit insurance products offer consumers and lenders protection from 
life events that limit a borrower’s ability to make payments on outstanding loan balances. These products offer consumers 
and lenders the option to protect loan balance repayment in the event of death, involuntary unemployment or disability. 
Our collateral insurance products are designed to primarily protect the lender 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  does  protect  against 
collision losses.

U.S.  Warranty  Solutions:  Provides  consumers  with  protection  from  certain  covered  losses  on  automobiles,  mobile  devices, 
consumer electronics, appliances and furniture in the United States. Our offerings include, but are not limited to, vehicle service 
contracts, roadside assistance and motor clubs, GAP, automobile dent and ding repair, key replacement, cellular handset protection 

9

 
and  service  contracts  on  other  consumer  goods.  We  distribute  our  products  through  agents,  retailers,  auto  dealerships  and  cell-
phone carriers. We are active in 50 states in the United States.

Our  service  contract  products  and  solutions  provide  consumers  with  coverage  for  specific  losses  to  automobiles,  recreation 
vehicles,  mobile  devices,  consumer  electronics,  appliances  and  furniture  and  bedding.  These  products  offer  benefits  such  as 
replacement,  service  or  repair  coverage  in  the  event  of  mechanical  breakdown,  accidental  damage  and  water  or  spill  damage.  
Some of our service contract products are extensions of coverage provided by their original equipment manufacturers. As part of 
our  vertically  integrated  offering,  we  provide  valuable  services  to  our  distribution  partners  including  premium  financing,  lead 
generation support, insurance sales, and business process outsourcing.

Europe  Warranty  Solutions:  Provides  consumers  with  protection  from  certain  covered  losses  on  automobiles,  mobile  devices, 
consumer  electronics,  appliances  and  furniture  in  the  European  region.  We  offer  a  variety  of  programs,  including  GAP,  VSCs, 
automobile dent and ding repair, tire and wheel protection, cellular handset protection, consumer products accidental damage and 
others. We distribute our programs through MGAs, retail agents and auto dealerships.

Our Competitive Strengths

Focus on Niche, Underserved Specialty Lines with Significant Fee-Based Income

We focus on specialty insurance business and have continued to diversify our revenues. We use three distinct approaches to grow 
our business: (i) we pursue and acquire agents with select books of business that we believe will maintain risk-appropriate rates; 
(ii) we seek agents with what we believe is distinct underwriting expertise to select specific niches; and (iii) we target the lines of 
business we believe are overlooked by the standard markets. For example, we often target the smaller premium-per-risk lines that 
we believe are highly profitable, have the potential to grow and are underserved by our competitors. We believe we have a unique 
ability to source small programs that meet our rate, form and risk threshold through our extensive distribution network and A.I. 
technology. 

We believe our underwriting expertise, proprietary technology and deep distribution relationships allow us to serve our specialty 
markets  and  capture  share.  We  cross-sell  multiple  products  to  our  customers  through  the  breadth  of  our  products  and  solutions, 
including fee-based services. We believe the combination of a low limits profile, low severity products and attractive fee income 
provides higher underwriting margin and earnings stability for our business. While low limits and low severity constitute most of 
our  underwritten  business,  we  believe  we  are  agile  enough  to  take  advantage  of  attractive  opportunities  in  challenging  market 
conditions. For the year ended December 31, 2021, Fortegra produced gross written premium and premium equivalents of $2,194 
million, an increase from $963 million in 2017, representing a 23% compounded annual growth rate over the past five years.

Track Record of Growth, Profitable Underwriting and Strong Economic Alignment with Our Distribution Network

Consistent underwriting is a function of rate adequacy and risk selection by our specialized agents. While we regularly establish 
sound actuarial rates similar to our insurance peers, we believe our stringent risk selection requires unique underwriting expertise 
by our agents and a high degree of specialty underwriting skillsets. After we establish relationships with our targeted agents, we 
further solidify our alliance by creating additional value for our distribution partners through our technology platform. We believe 
our A.I. algorithm and machine learning assisted underwriting drives a distinct lead generation advantage for our agents. Using A.I. 
technology and machine learning, we identify risks that fit into an acceptable profile, enhancing the agent’s efficiency and revenue 
base while allowing us to experience what we believe is a superior spread of risk and exceptional underwriting results. For the year 
ended December 31, 2021, our combined ratio was 90.6% and has averaged 91.6% over the past five years.

Scalable, Proprietary Technology, Which Drives Efficiency and Delivers Premium Customer Service

We  provide  many  aspects  of  insurance,  including  admitted  specialty  property-casualty  products,  E&S  line  offerings, 
administration,  premium  finance  and  other  value-added  services.  We  have  a  scalable  and  flexible  technology  infrastructure, 
together with highly trained and knowledgeable IT personnel and consultants. These resources allow us to launch new insurance 
and fee for service programs and expand gross written premiums and premium equivalents volume quickly and seamlessly without 
significant  incremental  expenses.  Our  technology  also  delivers  low-cost,  highly  automated  underwriting  and  administration 
services to our partners without substantial up-front investments. This technology-enhanced platform enables us to automate core 
business  processes,  reduce  our  operating  costs,  increase  our  operating  efficiency  and  secure  high  agent  retention.  We  have 
maintained a 95% persistency rate with our insurance producing agents over the past five years. Our underwriting expertise, strong 
distribution relationships and proprietary technology empower us to remain agile and take advantage of attractive opportunities in 

10

challenging  market  conditions.  Our  systems  also  enable  us  to  provide  a  high  level  of  service  to  our  distribution  partners  and 
customers through technology.

High-Quality, Conservative Balance Sheet with Solid Capitalization and Ratings

We maintain a high quality, S&P “AA+” rated, fixed income investment portfolio. Our investment portfolio’s principal objectives 
are to preserve capital and surplus, to maintain appropriate liquidity for corporate requirements, to support our strong ratings and to 
maximize  returns.  We  have  a  track  record  of  reducing  our  reinsurance  counterparty  exposure  by  partnering  with  reinsurers  that 
have  high-grade  credit  quality,  ensuring  high-quality  recoverable  assets  and  by  effectively  using  collateral  and  partnering  with 
producer owned reinsurance companies (“PORCs”). Our financial strength ratings of “A-” (Excellent) (Stable Outlook) from A.M. 
Best and “A-” (Stable Outlook) from KBRA reflect our adherence to our core values.

Distribution and Marketing

Our products are marketed and sold by agents and distribution partners. Our commercial and personal lines insurance products are 
marketed through a network of independent insurance agents, retailers, brokers and managing general agencies. Our partners that 
market and sell service contracts, collateral protection and credit insurance include financial services companies, big-box retailers, 
furniture  stores,  automobile  dealerships,  regional  cellular  service  providers  and  mobile  device  service  providers.  Our  service 
contract  offerings  are  primarily  marketed  and  sourced  through  insurance  intermediaries  including  third-party  administrators 
(“TPAs”), insurance brokers, MGAs and agents. Our vertically integrated platform also allows us to engage and enter into direct 
relationships with distributors. In each case, we pay our partners a commission-based fee (or a dealer net equivalent in the case of 
our service contract and protection product business).

We generally target markets that are niche and specialty in nature, which we believe are underserved by competitors and have high 
barriers to entry. We focus on establishing quality client relationships and emphasizing customer service. This focus, along with 
our ability to help clients enhance revenue and reduce costs, has enabled us to develop and maintain numerous long-term client 
relationships.

A  significant  portion  of  our  marketing  partnership  commission  agreements  are  on  a  variable  or  retrospective  commission  basis, 
which allows us to adjust commissions on the basis of claims experience. Under these types of arrangements, the compensation to 
our  marketing  partners  is  based  upon  the  actual  losses  incurred  compared  to  premiums  earned.  We  believe  these  types  of 
contractual  arrangements  align  their  economic  interests  with  ours,  help  us  to  better  manage  our  risk  exposure  and  deliver  more 
consistent profit margins with respect to these types of arrangements.

Underwriting

Our underwriting team consists of 90 underwriting professionals as of December 31, 2021. Our underwriters are industry veterans 
with deep knowledge of the specialty products that they underwrite, and they have longstanding relationships with our agents and 
distribution partners.

We  give  limited  underwriting  authority  to  our  MGAs.  This  means  that  we  give  our  MGAs  quote,  bind  and  policy  issuance 
authority  within  specifically  agreed  underwriting  guidelines.  Our  underwriters  work  with  our  MGA  partners  to  develop  the 
underwriting guidelines for each program. Exceptions to the underwriting guidelines require approval from a senior underwriter. 
Our portfolio of risk predominantly consists of business that is low severity and high frequency. Our underwriting team prices the 
business to a target margin, taking into account anticipated claims and administrative services. We believe our pricing encompasses 
prudent  risk  evaluation  based  on  historical  data,  while  remaining  commercially  competitive  and  sustainable.  We  believe  our 
approach  to  risk  selection,  pricing  and  underwriting  has  contributed  to  our  superior  combined  ratio,  which  has  averaged  91.6% 
over the past five years.

Technology

Fortegra is a data driven, technology enabled insurance platform that uses technology to support the business strategy through: (i) 
the ability to effectively serve small policies in a cost efficient manner; (ii) the ability to generate business leads that fit our risk 
profile using A.I.; (iii) enhancing underwriting results, improving the experience of our distribution partners; and (iv) the ability to 
grow our business and add new product lines with minimal incremental expense.

Our integrated, proprietary technology efficiently manages the high volume of policies and claims that result from servicing large 
numbers of small policyholders and contract holders. Our technology is highly automated, scalable and allows us to operate at a 

11

low cost. We believe this is a significant barrier to entry as many of our competitors have IT systems designed for larger policies, 
and do not have the ability to service a high volume of small policies in a cost efficient manner.

Through our A.I. algorithm and machine learning assisted underwriting, we provide qualified leads for new business to our agents. 
We  gather  proprietary  customer  performance  data,  correlated  characteristics  and  macro-economic  research  to  generate  an  ideal 
customer profile across our targeted business mixes. We then work with a third-party marketing consultant to translate the ideal 
customer  profiles  into  a  proprietary  target  customer  list  that  can  be  shared  with  our  agents.  This  both  enhances  the  agent’s 
efficiency and revenue base while allowing us to experience a superior spread of risk. 

Our flexible technology platform provides value-added services that we believe creates stronger relationships with our agents. In 
addition to the A.I. based lead generation service that we provide, our technology platform is connected to our agents and provides 
them with access to claims, research and reporting portals. We believe our technology makes it easier for agents to do business 
with us. These value-added services deepen our relationships and contribute to the high persistency rate with our agents. 

Our  technology  infrastructure  is  scalable  and  affords  us  the  opportunity  to  add  new  agents,  distribution  partners  and  services 
without significant additional expense.

Claims Management

We organize our claims department by lines of business, with specialized teams aligned by the line of business in which they have 
expertise.  Each  claims  adjuster  is  trained  and  experienced  in  evaluating  the  coverage  applicable  to  the  noticed  matter  and 
effectuating an appropriate resolution. When an insured reports a claim, it is immediately directed to the proper unit for handling. 

We maintain claims disposition authority for greater than 90% of claims adjudicated within the credit and service contract lines. 
We maintain claims disposition authority for greater than 70% of claims adjudicated within the property and casualty lines. 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. Our claims adjusters work closely with our underwriting team by keeping 
them  apprised  of  loss  trends  early  in  a  program’s  development.  For  certain  lines  of  business  that  have  high  frequency  and  low 
severity, we utilize TPAs to process claims. This allows our claims professionals to focus on more complex claims, and enhances 
the  efficiency  of  our  claims  department.  Our  MGAs  do  not  have  claims  authority  and  the  TPAs  that  we  use  do  not  have 
underwriting authority.

Our claims are generally reported and settled quickly, resulting in consistent historical loss development patterns and limited tail 
risk. We have data systems that allow for the centralization of data and creation of reports, which creates a management reporting 
tool allowing for the identification of trends within a product, specific jurisdiction or across multiple jurisdictions.

Investments

We invest in asset classes that we believe will maintain liquidity and support capital preservation while producing attractive risk-
adjusted  returns.  Most  of  these  securities  are  invested  in  short-duration  fixed  income  securities  that  are  both  highly  liquid  and 
highly rated. Our fixed maturity securities totaled $767 million and include cash and cash equivalents, available for sale securities, 
at  fair  value,  exchange  traded  funds  and  investment  grade  securities  classified  in  other  investments,  had  a  weighted-average 
effective  duration  of  2.6  years,  an  average  S&P  rating  of  AA+,  and  a  book  yield  of  1.3%  as  of  December  31,  2021.  These 
securities,  representing  84%  of  our  total  investments,  are  primarily  managed  by  BlackRock  with  direction  from  internal  asset 
management professionals. We internally manage credit risk assets, equities and alternative assets, which represented 16% of total 
investments as of December 31, 2021. We conduct monthly stress tests and use predictive analytics to manage our investments, 
which we believe reduces risk to our investment performance. We also maintain an investment committee that meets monthly to 
ensure our investment objectives remain aligned with our broader strategic and financial objectives.

Risk Management and Reinsurance

Consistent with standard industry practice for most insurance companies, we use reinsurance to manage our underwriting risk and 
efficiently utilize capital. In our commercial insurance lines, our reinsurers tend to be highly rated, well-capitalized professional 
third-party reinsurers. We typically contract 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 a letter 
of  credit.  A  significant  portion  of  our  distribution  partners  of  credit  and  service  contract  insurance  products  have  captive 
reinsurance companies to assume the insurance risk on the products they deliver. These captive reinsurance companies are known 
as PORCs and in most instances each PORC assumes almost all of the underwriting risk associated with the insurance products 

12

they  deliver.  When  we  use  PORCs,  consistent  with  applicable  laws  and  insurance  regulations,  we  act  in  a  fronting  and 
administrative  capacity  on  behalf  of  each  PORC,  providing  underwriting  and  claims  management  services.  We  receive  an 
administration  fee  that  compensates  us  for  our  expenses  associated  with  underwriting  and  servicing  the  underlying  policies. 
Because reinsurance does not relieve us of our primary liability to the policyholder, we generally require cash collateral to secure 
the reinsurance receivable in the event that a PORC is unable to pay the claims it has assumed. 

Market Opportunity

Commercial Lines

We underwrite and administer both admitted and E&S business. We believe underwriting business across multiple industries and 
geographies creates a conducive environment for targeting profitable programs, supporting agents with highly specialized skillsets 
and  focusing  on  overlooked  business  lines.  Our  approach  facilitates  participation  in  niche  markets  when  the  rate  environment 
presents  actionable  opportunities.  We  believe  the  breadth  of  our  underwriting  capacity,  services  and  expertise  afford  our  agents 
with  a  platform  that  meets  the  entirety  of  their  needs.  Our  risk-sharing  model  aligns  agents’  economics  to  their  underwriting 
performance, incentivizing agents to grow while maintaining strict profit margin discipline. Through long-term relationships with 
our  agents  and  substantial  experience  in  the  markets  we  serve,  we  believe  we  operate  in  an  advantageous  position  against  new 
market  entrants,  who  we  believe  would  find  it  time-consuming  and  expensive  to  compete  against  or  replicate  our  success.  Our 
commercial  lines  gross  written  premiums  (including  E&S  lines)  grew  to  $656.6  million  in  the  year  ended  December  31,  2021, 
compared to $469.8 million in the year ended December 31, 2020, an increase of 39.7%.

Personal Lines

We  are  a  leading  provider  of  credit  insurance  and  collateral  protection  products  in  the  United  States  and  believe  we  are  well 
positioned  to  increase  our  market  share  both  organically  and  potentially  through  acquisition.  We  believe  our  capabilities  and 
reputation have allowed us to better position ourselves competitively for new business and renewals in the marketplace. We also 
believe our market position, capabilities and reputation will make us a preferred acquisition partner for smaller competitors that 
may choose to exit the market or desire a partner with more resources. Our personal lines gross written premiums grew to $781.8 
million in the year ended December 31, 2021, compared to $593.9 million in the year ended December 31, 2020, an increase of 
31.6%.

U.S. Warranty Solutions

We believe we can significantly increase our market presence in the service contract sector. We entered the service contract market 
as  a  natural  extension  of  our  insurance  products  given  that  it  possesses  similar  attributes  and  distribution  channels.  Our  service 
contract  gross  written  premium  equivalents  grew  to  $652.1  million  in  the  year  ended  December  31,  2021,  compared  to  $550.0 
million in the year ended December 31, 2020, an increase of 18.6%. We believe the demand from consumers for extended service 
contracts  on  products  such  as  automobiles,  furniture,  mobile  phones  and  electronics  will  continue  to  drive  long-term  growth 
opportunities. 

Europe Warranty Solutions

In  2018,  we  expanded  into  Europe  where  we  believe  our  existing  protection  solutions  and  service  contract  offerings  can  be 
successfully  distributed  while  maintaining  similar  levels  of  historical  underwriting  performance.  Our  European  gross  written 
premiums and equivalents grew to $103.6 million in the year ended December 31, 2021, compared to $53.2 million in the year 
ended December 31, 2020, an increase of 94.6%.

Competition

We  operate  in  several  markets,  and  believe  that  no  single  company  competes  against  us  in  all  of  our  business  lines.  We  may 
compete with other specialty carriers or program managers within a given program, but no specific insurers can be identified as 
clear  competition  across  all  of  our  business  lines.  Within  the  United  States,  we  compete  with  specialty  insurers  like  Markel 
Corporation,  RLI  Corporation  and  Clear  Blue  Insurance  Group.  We  also  compete  with  larger  insurance  companies  that  may 
selectively  underwrite  specialty  or  credit  lines  such  as  AIG  and  Allianz  SE.  Within  our  U.S.  and  European  Warranty  Solutions 
lines of business, we compete with Assurant, Securian Financial, Great American, Asurion, LLC, AmTrust Financial, SquareTrade 
Inc.,  Allianz  SE,  Helvetia  Insurance  and  AXA  SA.  These  lists  are  not  exhaustive  and  are  constantly  evolving  as  we  and  our 
competitors expand coverages.

13

In general, the insurance markets we operate in are highly competitive. The competition we face is due to 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. We primarily compete by leveraging our proprietary technological platform, 
decades of underwriting expertise, robust distribution relationships, data-driven marketing initiatives, our “agent-first” mentality, 
and best-in-class reputation.

Regulation

We are subject to federal, state, local and foreign regulation and supervision. 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.

Our  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 the regulation of market conduct, including underwriting and claims practices. 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.

Our  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 we are licensed to sell insurance policies for 
purposes of measuring statutory surplus and, in some instances, would require us 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 
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).

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. 

Our  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 an acquisition 
of control of a domestic insurer and payments of extraordinary dividends or distributions.

Our insurance and service contract 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. Our 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. 

A portion of our foreign business is conducted via our insurance company in Malta. Malta is a member country of the EU, and we 
are  active  in  fourteen  countries  in  the  EU,  plus  the  United  Kingdom.  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 minimum set of rules and standards for protecting policyholders across the EU. 

14

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 their 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 businesses 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.  After  Brexit,  United  Kingdom  regulators  established  the  Temporary  Permissions  Regime, 
which permits passporting insurers to continue operating in the United Kingdom for up to three years post-Brexit. We are active in 
and subject to regulation in the United Kingdom. Our Malta company was passporting into the United Kingdom prior to Brexit and 
registered to operate under the Temporary Permissions Regime until permanent authority is granted by United Kingdom regulators. 
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 our compliance costs and subject us to 
operational challenges in the region. 

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

We are also subject to federal and state laws and regulations related to the administration of insurance products on behalf of other 
insurers. In order for us to process and administer insurance products of other companies, we are required to maintain licenses of a 
third-party administrator in the states where those insurance companies operate. We are also subject to the related federal and state 
privacy laws and must comply with federal and state data protection and privacy laws. 

Seasonality

Our  financial  results  historically  have  been,  and  we  expect  to  continue  to  be,  affected  by  seasonal  variations.  Revenues  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,  our  revenues  have  historically  been  higher  in  the 
third and fourth quarters than in the first half of the year.

Intellectual Property

We  own  or  license  a  number  of  trademarks,  patents,  trade  names,  copyrights,  service  marks,  trade  secrets  and  other  intellectual 
property rights that relate to our services and products within the various jurisdictions we operate. Although we believe that these 
intellectual  property  rights  are,  in  the  aggregate,  important  to  our  business,  we  also  believe  that  our  business  is  not  materially 
dependent  upon  any  particular  trademark,  trade  name,  copyright,  service  mark,  license  or  other  intellectual  property  right. 
Additionally, our insurance subsidiaries have entered into confidentiality agreements with their clients that impose restrictions on 
client use of our proprietary software and other intellectual property rights.

Employees

As of December 31, 2021, Fortegra had 778 employees across 15 offices in four 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.

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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  loans  that  can  be  transferred  to  Government  National  Mortgage  Association  (“Ginnie  Mae”)  pools  or  sold  on  a 
servicing-retained  or  servicing-released  basis  to  Federal  National  Mortgage  Association  (“Fannie  Mae”),  Federal  Home  Loan 
Mortgage  Corporation  (“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

We are subject to extensive regulation by federal, state and local governmental authorities, including the CFPB, the Federal Trade 
Commission and various 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

At December 31, 2021, our Mortgage operations had 442 employees.

Tiptree Capital - Other

Tiptree Capital - Other currently includes:

•

•

•
•

Our  investment  holdings  in  the  maritime  transportation  sector,  primarily  in  dry  bulk  vessels  and  product  tankers  that 
transport commodities, such as coal, grains and clean petroleum products.
Our share holdings of Invesque, a publicly traded real estate investment company that specializes in health care and senior 
living property investment throughout North America.
Our ownership of Corvid Peak, a credit oriented, special situations asset manager.
Our held for sale mortgage originator, Luxury Mortgage.

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 

16

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 UK 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  investments  in  maritime  transportation  are  regulated  under  international  conventions,  classification  societies,  national,  state 
and local laws and regulations in force in the jurisdictions in which our vessels operate, as well as in the country or countries of 
their  registration,  that  mandate  safety  and  environmental  protection  policies.  Government  regulation  of  vessels,  particularly 
environmental regulations, have become more stringent and may require us to incur significant capital expenditures on our vessels. 
Our  international  operations  and  activities  also  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. 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.  We  operate  in  countries  known  to 
present heightened risks for corruption, and our dry bulk shipping and related operations requires us to interact with government 
officials, including port officials, harbor masters, maritime regulators, customs officials and pilots. 

Employees

At December 31, 2021, Tiptree Capital - Other’s combined operations had 231 employees.

Human Capital

The success of our businesses depend 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. 
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, 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  our  communities  by  lending  a  helping  hand  to  those  in  need.  We 
undertake  multiple  initiatives  to  support  military  families  and  local  charities  focused  on  the  health  and  welfare  of  children  and 
families.  We  also  support  clean  water  initiatives  in  Africa.    Fortegra  N.O.W.  (Network  of  Women)  is  working  to  ensure  equal 
access  to  leadership  positions  in  the  insurance  industry  regardless  of  gender  or  race.  This  is  being  accomplished  through 

17

unconscious  bias  training,  mentoring  programs,  education  reimbursement,  and  policies  that  support  work/life  balance  and  equal 
pay for equal jobs. This group is led by female executives at Fortegra. The programming and resources provided are available to all 
Fortegra employees.

At Fortegra, we have developed an education program that assists employees in developing key skills that enable them to perform 
their jobs and to advance their careers. We also have a Leadership Development Program (“LDP”) that identifies new talent and 
prepares them for success within the organization. The program hires recent college graduates who will typically rotate through 
several  departments  over  a  two-year  period,  becoming  fully  immersed  in  the  insurance  company’s  business.  Our  goal  for 
successful LDP participants is to hire them on a full time basis upon completion of the program. 

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., 299 Park Avenue, 13th Floor, New York, NY, 10171, Attn: 
Investor Relations, telephone: (212) 446-1400, email: IR@tiptreeinc.com.

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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, dry-bulk vessels and product tankers, 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, 2021, 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  legislative  or  industry  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.

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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 
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.

Failure to consummate the proposed WP Transaction could have a material adverse impact on our business, financial 
condition  and  results  of  operations,  and  if  the  proposed  WP  Transaction  is  consummated,  Warburg  Pincus  may  exert 
substantial influence on Fortegra, potentially in a manner that is not in Tiptree’s shareholders’ interests.

The consummation of the proposed WP Transaction is subject to the satisfaction or waiver of specified closing conditions, 
including filings with, and approvals from, insurance and other relevant regulatory agencies. There can be no assurance that these 
and other conditions to closing will be satisfied in a timely manner or at all.

A  failed  transaction  may  result  in  negative  publicity  and  a  negative  impression  of  us  in  the  investment  community  or 
business community generally. We have incurred, and will continue to incur, significant costs, expenses and fees for professional 
services and other transaction costs in connection with the proposed WP Transaction, for which we will have received little or no 
benefit if the proposed WP Transaction is not completed. 

If the WP Transaction is consummated, Warburg Pincus would acquire an approximate 24% ownership in Fortegra on an 
as  converted  basis  from  us  and  would  have  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 Pincus would also have pro rata representation on the Fortegra board of 
directors. As a result of their substantial ownership in Fortegra if the WP transaction in consummated, Warburg Pincus 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, including Smart AutoCare, 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 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 

20

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 

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 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.”  In  recent  years, 
interest rates have been at or near historic lows. A protracted low interest rate environment would continue to place pressure on our 
insurance  subsidiaries’  net  investment  income,  which,  in  turn,  would  have  a  material  adverse  effect  on  our  profitability.  Future 
increases in interest rates could cause the values of our insurance subsidiaries’ fixed income securities portfolios to decline, 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.

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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 
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.

Our insurance subsidiaries’ 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 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. 

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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 
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, denial-
of-service attacks, viruses, worms, other malicious software programs, the loss of stored data, programming errors, the breakdown 
or malfunctioning of computer equipment or software systems, telecommunications failure or damage caused by weather or natural 
disasters, 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. 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. Global cybersecurity threats can range from uncoordinated individual 
attempts to gain unauthorized access to our information technology (“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 and generally are not recognized until launched against a target, our businesses 
and  the  third  parties  with  whom  they  do  business  may  be  unable  to  anticipate  these  techniques  or  to  implement  adequate 
preventative measures. With the increasing frequency of cyber-related frauds 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  may  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.

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.  Our 

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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 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  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 contracts with these distributors are 
typically  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 clients 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 clients or 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. 
Factors that could affect such analyses include:

•

•
•
•
•

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;

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•

•

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 
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 

25

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 or new products and services may subject our insurance subsidiaries to additional risks.

From time to time, our insurance subsidiaries may implement new lines of business or offer new products and services 
within  existing  lines  of  business.  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 and/or new products or services, 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 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. 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 and/or 
new  product  or  service  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 
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  and  credit  risk. 
Changes in the value of the U.S. dollar relative to other currencies 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.

26

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 
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  as  a  result  of  the  COVID-19  pandemic,  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  their  quarterly  results  to  continue  to  fluctuate  in  the  future  due  to  a  number  of  factors,  including  the  general  economic 
conditions  in  the  markets  where  they  operate,  the  frequency,  occurrence  or  severity  of  catastrophic  or  other  insured  events  or 
otherwise, fluctuating interest rates, claims exceeding their loss reserves, competition in their industry, deviations from expected 
renewal rates of their existing policies and contracts, adverse investment performance and the cost of reinsurance coverage.

27

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”).  Our  commercial  &  personal  lines 
program business is exposed to these hard and soft market cycles. We seek to isolate ourselves from these trends by focusing on 
smaller risks with lower severities and utilizing reinsurance. Because this market cyclicality is due in large part to the actions of 
our  insurance  subsidiaries’  competitors  and  general  economic  factors,  the  timing  or  duration  of  changes  in  the  market  cycle  is 
unknown. We expect these cyclical patterns will cause our insurance subsidiaries’ revenues and net income to fluctuate, which may 
cause their results of operations, financial condition and cash flows to be more volatile. We believe that we are currently in the 
second year of a hardening market.

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 the policies. Existing policyholders may exaggerate or even falsify 
claims to obtain higher claims payments. These outcomes would reduce their underwriting profit to the extent these factors are not 
reflected in the rates they charge.

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 including, but not limited to the COVID-19 
pandemic,  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.

The dry bulk and product tanker shipping industry is cyclical with high volatility in charter hire rates and profitability. 
The  degree  of  charter  hire  rate  volatility  among  different  types  of  dry  bulk  vessels  and  product  tankers  has  varied  widely. 
Fluctuations in charter rates result from changes in the supply of and demand for vessel capacity and changes in the supply of and 
demand for the major commodities carried by dry bulk vessels internationally and for oil, oil products and chemicals carried by 
product tankers. Demand is a function of world economic conditions and the consequent requirement for commodities, oil and oil 
products, production and consumption patterns, as well as events, which interrupt production, trade routes, and consumption. The 
factors  affecting  the  supply  of  and  demand  for  vessels  are  outside  of  our  control  and  are  unpredictable.  We  may  not  be  able  to 
employ our vessels at charter rates as favorable to us as historical rates or operate our vessels profitably. Significant declines in dry 
bulk or product tanker charter rates could adversely affect our revenues and profitability.

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 

28

 
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.

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.

29

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:

•
•
•
•
•
•
•

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 Amended and Restated Credit Agreement dated as of August 4, 2020 
among  Fortegra  Financial  and  Lots  Intermediate  Co.,  as  Borrowers,  Fifth  Third  Bank,  National  Association,  as  Administrative 
Agent and Issuing Lender, Citizens Bank, N.A., as Syndication Agent, and First Horizon Bank, Keybank National Association and 
Synovus Bank as Co-Documentation Agents 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 European Union on December 31, 2020 (which is commonly referred to as 
“Brexit”).  Aspects  of  the  relationship  between  the  United  Kingdom  and  the  European  Union  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 European Union, among other factors. The 
Financial  Conduct  Authority  and  the  Prudential  Regulation  Authority  in  the  United  Kingdom  established  the  Temporary 
Permissions Regime, which creates a three year post-Brexit period where companies can continue to operate until their permanent 
establishment  is  authorized  in  the  United  Kingdom.  Fortegra’s  Malta  based  insurance  subsidiary  registered  for  the  Temporary 
Permissions Regime and entered into it on December 31, 2020. Because our insurance subsidiaries conduct business in both the 
United Kingdom and the European Union and because they rely on their Malta insurance subsidiary’s ability to conduct business in 
the United Kingdom, they face risks associated with the potential 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.

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

30

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 business’s 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 intellectual property, which includes 
their rights in their technology platform and their brand. Our insurance subsidiaries primarily rely on a combination of copyright, 
trade  secret  and  trademark  laws  and  confidentiality  agreements,  procedures  and  contractual  provisions  with  their  employees, 
customers, service providers, partners and other third parties to protect their proprietary or confidential information and intellectual 
property rights. However, the steps they 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. 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 

31

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  for  use  in  their  business,  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 or re-engineer all or a portion of their technology systems, 
each  of  which  could  reduce  or  eliminate  the  value  of  their  technology  systems.  Such  risk  could  be  difficult  or  impossible  to 
eliminate and could adversely affect our business’s results of operations, financial condition and cash flows.

A significant decrease of the market values of our vessels could cause us to incur an impairment loss.

We review our vessels for impairment whenever events or changes in circumstances indicate that the carrying amount of 
the vessels may not be recoverable. Such indicators include declines in the fair market value of vessels, decreases in market charter 
rates,  vessel  sale  and  purchase  considerations,  fleet  utilization,  vessels’  useful  lives,  scrap  values,  regulatory  changes  in  the  dry 
bulk and product tanker shipping industry or changes in business plans or overall market conditions that may adversely affect cash 
flows. We may be required to record an impairment charge with respect to our vessels and any such impairment charge may have a 
material adverse effect on our business, financial condition and results of operations.

Our vessels may suffer damage and we may face unexpected drydocking costs.

If  our  vessels  suffer  damage,  they  may  need  to  be  repaired  at  a  drydocking  facility.  The  costs  of  drydock  repairs  are 
unpredictable and can be substantial. The loss of earnings while a vessel is being repaired and repositioned, as well as the actual 
cost of these repairs not covered by our insurance, would decrease our earnings and available cash. While we carry insurance on 
our vessels, that insurance may not be sufficient to cover all or any of the costs or losses for damages to our vessels and we may 
have to pay drydocking costs not covered by our insurance.

The operation of dry bulk vessels and product tankers has certain unique operational risks.

With a dry bulk vessel, the cargo itself and its interaction with the vessel may create operational risks. By their nature, dry 
bulk cargoes are often heavy, dense and easily shifted, and they may react badly to water exposure. In addition, dry bulk vessels 
are often subjected to battering treatment during unloading operations with grabs, jackhammers (to pry encrusted cargoes out of the 
hold) and small bulldozers. This treatment may cause damage to the vessel. Vessels damaged due to treatment during unloading 
procedures may be more susceptible to breach while at sea. Breaches of a dry bulk vessel’s hull may lead to the flooding of the 
vessel’s holds. If a dry bulk vessel suffers flooding in its forward holds, the bulk cargo may become so dense and waterlogged that 
its pressure may buckle the vessel’s bulkheads, leading to the loss of a vessel. If we do not adequately maintain our vessels, we 
may be unable to prevent these events. 

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In  addition,  the  operation  of  product  tankers  has  unique  operational  risks  associated  with  the  transportation  of  oil  and 
chemical products. An oil or chemical spill may cause significant environmental damage, and the associated costs could exceed the 
insurance coverage available to us. Compared to other types of vessels, tankers are exposed to a higher risk of damage and loss by 
fire,  whether  ignited  by  a  terrorist  attack,  collision,  or  other  cause,  due  to  the  high  flammability  and  high  volume  of  the  oil  or 
chemicals  transported  in  tankers.  The  occurrence  of  any  of  these  events  could  have  a  material  adverse  effect  on  our  business, 
financial condition and results of operations.

Acts of piracy on ocean-going vessels occur and may increase in frequency.

Acts of piracy have historically affected ocean-going vessels trading in regions of the world such as the South China Sea, 
the Indian Ocean and in the Gulf of Aden off the coast of Somalia. Although the frequency of sea piracy worldwide has generally 
decreased  since  2013,  sea  piracy  incidents  continue  to  occur,  particularly  in  the  Gulf  of  Aden  off  the  coast  of  Somalia  and 
increasingly in the Sulu Sea and the Gulf of Guinea, with dry bulk vessels and tankers particularly vulnerable to such attacks. Acts 
of piracy could result in harm or danger to the crews that man our vessels.

If these piracy attacks occur in regions in which our vessels are deployed that insurers characterized as “war risk” zones or 
Joint  War  Committee  “war  and  strikes”  listed  areas,  premiums  payable  for  such  coverage  could  increase  significantly  and  such 
insurance coverage may be more difficult to obtain. In addition, crew costs, including the employment of onboard security guards, 
could  increase  in  such  circumstances.  Furthermore,  while  we  believe  the  charterer  remains  liable  for  charter  payments  when  a 
vessel is seized by pirates, the charterer may dispute this and withhold payment until the vessel is released. A charterer may also 
claim that a vessel seized by pirates was not “on-hire” for a certain number of days and is therefore entitled to cancel the charter. 
We  may  not  be  adequately  insured  to  cover  losses  from  these  incidents,  which  could  have  a  material  adverse  effect  on  us.  In 
addition,  any  detention  hijacking  as  a  result  of  an  act  of  piracy  against  our  vessels,  or  an  increase  in  cost,  or  unavailability,  of 
insurance for our vessels, could have a material adverse impact on our business, financial condition and earnings.

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. 

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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.  Due  to  the  unprecedented  events  surrounding  the  COVID-19  pandemic  along  with  the  associated  severe  market 
dislocation, there is an increased degree of uncertainty and unpredictability concerning current interest rates, future interest rates 
and potential negative interest rates. The historically low interest rate environment over the last several years has created strong 
demand  for  mortgages.  Increases  in  interest  rates  could  result  in  us  having  lower  revenue  or  profitability.  The  overwhelming 
majority of our mortgage loan originations have historically been refinancing existing homeowner’s mortgage loans. With rates at 
or near historically low levels, we have been able to continue to grow our mortgage loan originations by focusing on refinances. 
With rising interest rates, we may not be able to continue to do so 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. 
Long-term residential mortgage interest rates have been at or near record lows for an extended period, but they may increase in the 
future. 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.  With  sustained  low  interest  rates,  as  we  have  been  experiencing, 
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.

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.  If  interest  rates  increase,  our  mortgage  business’s  debt  service  obligations  on  certain  of  its 
variable-rate  indebtedness  will  increase  even  though  the  amount  borrowed  remains  the  same,  and  net  income  and  cash  flows, 
including  cash  available  for  servicing  indebtedness,  will  correspondingly  decrease.  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 U.S. Federal Reserve, which influence interest rates 
and impact the size of the loan origination market. In 2017, the U.S. Federal Reserve ended its quantitative easing program and 
started its balance sheet reduction plan. The U.S. 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  prior  to  the  COVID-19 
pandemic,  the  U.S.  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.  In  particular,  U.S.  Federal  Reserve  announced  programs  to  increase  its  purchase  of  certain  MBS  products  in 
response to the COVID-19 pandemic's effect on the U.S. economy, and the market for MBS in particular. The lasting results of this 
policy change by the U.S. Federal Reserve are unknown at this time, as is its duration, but could affect the liquidity of MBS in the 
future.

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 

34

 
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 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 
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. 

The contracts with purchasers of our whole loans contain provisions that require us to indemnify or repurchase the related 

loans under certain circumstances. While our contracts 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. 

35

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.

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 have been at historically low levels for the last several years, a period of sharply rising interest rates could 
have an adverse impact on our business by negatively impacting demand for mortgages and increasing our cost of borrowing to 
finance operations. 

In  addition,  in  July  2017,  the  Chief  Executive  of  the  United  Kingdom  Financial  Conduct  Authority,  which  regulates 

36

LIBOR,  announced  its  intent  to  stop  persuading  or  compelling  banks  to  submit  rates  for  the  calculation  of  LIBOR  to  the 
administrator  of  LIBOR  after  2021.  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  commercial 
automotive loans, corporate finance loans, and mortgage loans, as well as certain investment securities, derivative contracts, and 
trust  preferred  securities,  among  other  arrangements.  The  U.S.  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 
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 

37

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, 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.

The  global  spread  of  the  coronavirus  (COVID-19)  created  significant  market  volatility  and  uncertainty  and  economic 
disruption. In addition, the impact of COVID-19 and measures to prevent its spread caused, and may continue to cause, substantial 
disruption  to  distribution  channels,  auto  dealer  partners  and  contract  counterparties,  and  may  limit  our  access  to  capital  and 
customers through self-isolation, travel limitations, business restrictions, margin calls, and otherwise. These effects, individually or 
in the aggregate, could materially adversely impact our businesses, financial condition, operating results, liquidity and cash flows 
and such adverse impacts may be material to our results of operations and liquidity position. Any of the foregoing factors, or other 
cascading  effects  of  the  COVID-19  pandemic  that  are  not  currently  foreseeable,  could  materially  increase  our  costs,  negatively 
impact our sales and damage the Company’s results of operations and its liquidity position, possibly to a significant degree. The 
duration of any such impacts cannot be predicted at this time.

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, 
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.

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 

38

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 of 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 2020 of 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 
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 

39

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.

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.

40

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. 

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. A number of our subsidiaries are subject to numerous U.S. federal and state 
laws and non-U.S. regulations governing the protection of personally identifiable and confidential information of their customers 
and  employees.  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  new  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 (“CCPA”), which among other things, requires companies 
covered by the legislation to provide new disclosures to California consumers and afford such consumers new rights of access and 

41

deletion of personal information. Additionally, when it becomes effective on January 1, 2023, our insurance subsidiaries will be 
subject  to  the  California  Privacy  Rights  Act  (“CPRA”),  which  will  significantly  expand  consumers’  rights  under  the  CCPA. 
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 European 
Union, or 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. 

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 
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.

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, 

42

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.

Our  dry  bulk  shipping  and  product  tanker  business  and  the  operation  of  our  vessels  are  regulated  under  international 
conventions, classification societies, national, state and local laws and regulations in force in the jurisdictions in which our vessels 
operate,  as  well  as  in  the  country  or  countries  of  their  registration,  that  mandate  safety  and  environmental  protection  policies. 
Government regulation of vessels, particularly environmental regulations, have become more stringent and may require us to incur 
significant capital expenditures on our vessels.

For  example,  various  jurisdictions  have  regulated  management  of  ballast  waters  to  prevent  the  introduction  of  non-
indigenous  species  that  are  considered  invasive  which  requires  us  to  make  changes  to  the  ballast  water  management  plans  we 
currently  have  in  place  and  to  install  new  equipment  on  board  our  vessels.  Various  jurisdictions  have  also  regulated  or  are 
considering  the  further  regulation  of  greenhouse  gases  from  vessels  and  emissions  of  sulfur  and  nitrogen  oxides,  which  may 
increase the cost of new vessels and require retrofitting equipment on existing vessels. Effective January 1, 2020, the International 
Maritime Organization (“IMO”) imposed the IMO 2020 Regulations which require all ships to burn fuel with a maximum sulfur 
content  of  0.5%,  which  is  a  significant  reduction  from  the  previous  threshold  of  3.5%.  Commencing  January  1,  2020,  ships  are 
required to remove sulfur from emissions through the use of scrubbers or other emission control equipment, or purchase marine 
fuel with 0.5% sulfur content, which has led to increased demand for this type of fuel compared to the price we would have paid 
had  the  IMO  2020  Regulations  not  been  adopted.  Substantially  all  of  the  vessels  chartered  by  us  do  not  have  scrubbers,  which 
means  we  are  required  to  purchase  low  sulfur  fuel  for  our  vessels.  Our  vessels  began  operating  on  0.5%  low  sulfur  fuel  in 
compliance with the IMO 2020 Regulations. As a result of the IMO 2020 Regulations and any future regulations with which we 
must comply, we may incur substantial additional operating costs.

These requirements can also affect the resale prices or useful lives of our vessels or require reductions in cargo capacity, 
ship  modifications  or  operational  changes  or  restrictions.  Failure  to  comply  with  these  requirements  could  lead  to  decreased 
availability of, or more costly insurance coverage for environmental matters or result in the denial of access to certain jurisdictional 
waters  or  ports,  or  detention  in  certain  ports.  Under  local,  national  and  foreign  laws,  as  well  as  international  treaties  and 
conventions, we could incur material liabilities, including cleanup obligations and claims for natural resource, personal injury and 
property damages in the event that there is a release of petroleum or other hazardous materials from our vessels or otherwise in 
connection  with  our  operations.  Violations  of,  or  liabilities  under,  environmental  regulations  can  result  in  substantial  penalties, 
fines and other sanctions, including, in certain instances, seizure or detention of our vessels. In addition, we are subject to the risk 
that we, our affiliated entities, or our or their respective officers, directors, shore employees, crew on board and agents may take 
actions determined to be in violation of such environmental regulations and laws and our environmental policies. Any such actual 
or  alleged  environmental  laws  regulations  and  policies  violation,  under  negligence,  willful  misconduct  or  fault,  could  result  in 
substantial fines, civil and/or criminal penalties or curtailment of operations in certain jurisdictions, and might adversely affect our 
business,  results  of  operations  or  financial  condition.  In  addition,  actual  or  alleged  violations  could  damage  our  reputation  and 
ability  to  do  business.  Furthermore,  detecting,  investigating  and  resolving  actual  or  alleged  violations  is  expensive  and  can 
consume significant time and attention of our senior management. Events of this nature could have a material adverse effect on our 
business, financial condition and results of operations.

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.

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 (“TILA”), 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 

43

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  (“F&I”)  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.

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 

44

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.

Item 1B. Unresolved Staff Comments
None.

Item 2. Properties

Our principal executive office is located at 299 Park Avenue, 13th Floor, New York, New York 10171. 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

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

45

As of December 31, 2021, there were 59 common stockholders of record. This number does not include beneficial owners whose 
shares are held by nominees in street name. 

Item 6. Reserved.

46

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  origination,  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  shareholders’  long-term  total  return  on 
capital, as measured by growth in stock price plus dividends paid, in addition to Adjusted Net Income and Adjusted EBITDA. 

Our 2021 highlights include:

Overall:

•

•

•

Net income of $38.1 million increased from a net loss of $29.2 million in 2020, driven by growth in insurance and 
shipping operations, in addition to realized and unrealized gains on investments as compared to losses in 2020.
Adjusted  net  income  of  $63.9  million  increased  24.2%  from  $51.4  million  in  2020,  driven  by  improvement  in 
insurance and shipping operations. Adjusted return on average equity was 16.5%, as compared to 13.1% in 2020.
On October 12, 2021, Tiptree announced a $200 million strategic investment in its insurance subsidiary, Fortegra, 
by  Warburg  Pincus,  a  leading  global  growth  investor.  The  investment  will  give  Warburg  Pincus  an  approximate 
24% ownership in Fortegra on an as converted basis and is expected to close in the second quarter 2022, subject to 
regulatory approvals.

Insurance:
•

Gross written premiums and premium equivalents were $2,194.0 million for the year ended December 31, 2021, as 
compared to $1,666.9 million for the year ended December 31, 2020, up 31.6% as a result of growth in admitted 
and E&S insurance lines as well as growth in fee-based service contract offerings.
Total  revenues  increased  42.4%  to  $984.1  million,  from  $691.1  million  in  2020,  driven  by  increases  in  earned 
premiums, net, service and administrative fees, and net investment income.
The  combined  ratio  improved  to  90.6%,  as  compared  to  91.5%  in  2020,  driven  by  the  continued  scalability  of 
Fortegra’s technology and shared service platform, which improved the expense ratio, while the underwriting ratio 
remained stable.
Income before taxes of $69.9 million increased by $42.9 million as compared to $26.9 million in 2020. Return on 
average  equity  was  17.1%  in  2021  as  compared  to  8.1%  in  2020.  The  increase  in  both  metrics  was  driven  by 
revenue growth and an improved combined ratio, in addition to improved returns on investments as compared to the 
prior year.
Adjusted net income increased 53.8% to $66.8 million, as compared to $43.4 million in 2020. Adjusted return on 
average  equity  was  22.2%,  as  compared  to  15.2%  in  2020.  The  increase  in  both  metrics  was  driven  by  revenue 
growth and an improved combined ratio.

•

•

•

•

Tiptree Capital:

• Mortgage income before taxes was $28.4 million in 2021, as compared to $31.1 million in 2020, with the decrease 
driven  by  a  decline  in  gain  on  sale  margins,  partially  offset  by  higher  servicing  fees  and  positive  fair  value 
adjustments on the mortgage servicing portfolio. Return on average equity was 38.9% in 2021.

• Maritime transportation income before taxes was $11.6 million in 2021, as compared to $1.5 million in 2020, with 

the increase driven by a rise in dry-bulk charter rates.

Key Trends:

47

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 this 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,  changing  regulatory  requirements  and 
slowing business conditions can have a material adverse effect on our results of operations or financial condition.

Fortegra generally offers products which have low severity but high frequency loss experiences and are short duration. As a 
result, the business has historically generated significant fee-based revenues. In general, the types of products Fortegra offers 
tend  to  have  limited  aggregation  risk  and,  thus,  limited  exposure  to  catastrophic  and  residual  risk.  Underwriting  risk  is 
mitigated  through  a  combination  of  reinsurance  and  retrospective  commission  structures  with  agents,  distribution  partners 
and/or  third-party  reinsurers.  To  mitigate  counterparty  risk,  Fortegra  ensures  its  distribution  partners’  captive  reinsurance 
entities  are  over-collateralized  with  highly  liquid  investments,  primarily  cash  and  cash  equivalents.  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.  While  Fortegra’s  insurance  operations  have  historically 
maintained  a  relatively  stable  combined  ratio,  initiatives  to  change  the  business  mix  along  with  economic  factors  could 
generate  different  results  than  the  business  has  historically  experienced.  We  believe  there  will  continue  to  be  growth 
opportunities to expand Fortegra’s specialty insurance offerings to other niche products and markets.

Fortegra’s investment portfolio includes fixed maturity securities, loans, credit investment funds, and equity securities. Many 
investments are held at fair value. Changes in fair value for loans, credit investment funds, and equity securities are reported 
quarterly as unrealized gains or losses in revenues and can be impacted by changes in interest rates, credit risk, or market risk, 
including specific company or industry factors. 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. 

The Federal Reserve has signaled that it intends to raise interest rates in the near term. Rising 10-year treasury yields, and the 
tapering of the Federal Reserve’s purchases of mortgage backed securities, has resulted in increases to mortgage interest rates 
as well, although those rates still remain at relative historic lows.

Our businesses can also be impacted in various ways by changes in interest rates, which can result in fluctuations in the fair 
value of investments, revenues associated with floating rate investments, volume and revenues in mortgage operations and 
interest expenses associated with floating rate debt used to fund operations. Rising interest rates could impact the value of 
certain 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  can  result  in  higher  interest  income  on  investments  over  time.  In  declining  interest  rate 
environments, the opposite impacts could occur. In addition, certain investments are based on floating interest rates, which 
has resulted in lower investment income during the recent period of extended low rates. 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.

Low mortgage rates due to the Federal Reserve intervention in mortgage markets, and rising home prices in certain markets, 
has  resulted  in  a  combination  of  higher  mortgage  volumes  and  margins  beginning  in  the  second  quarter  of  2020  and 
continuing through 2021, which has been a benefit to our mortgage operations. The recent low interest rate environment also 
benefits interest cost on debt, although corporate debt remains above current LIBOR rates. There can be no assurance that 
these positive trends will continue, the reversal of which could have a materially negative impact on our results of operations, 
and which may only be partially mitigated by the benefit to LIBOR based investments.

Authorities that regulate LIBOR have announced plans to phase out LIBOR, such that LIBOR is expected to cease to exist as 
a benchmark for floating interest rates. The Federal Reserve Board and the Federal Reserve Bank of New York organized the 
Alternative  Reference  Rates  Committee,  which  identified  the  Secured  Overnight  Financing  Rate  (SOFR)  as  its  preferred 
alternative rate for USD-LIBOR. We are not able to predict when LIBOR will cease to be available or when there will be 
sufficient  liquidity  in  the  SOFR  markets  as  a  replacement  reference  rate.  Such  uncertainty  may  result  in  a  sudden  or 
prolonged  increase  or  decrease  in  reported  LIBOR  and/or  its  replacement  rate.  To  address  the  phase  out  of  LIBOR,  the 
agreements for our debt facilities include a mechanism to replace LIBOR with an alternative reference rate under specified 
circumstances, whether that replacement is SOFR or another benchmark. If future rates based upon the successor reference 

48

rate  are  higher  than  LIBOR  rates  as  currently  determined  due  to  illiquidity  or  other  factors,  our  interest  expense  could 
increase.

Common  shares  of  Invesque  represent  a  significant  asset  on  our  consolidated  balance  sheet,  both  as  part  of  insurance 
investments  and  separately  in  Tiptree  Capital.  Our  investment  in  Invesque,  which  operates  in  the  seniors  housing,  skilled 
nursing and medical office industries, is carried on our consolidated balance sheet at fair value. In April 2020, in response to 
the uncertainty in the industry, Invesque suspended its dividend to conserve liquidity. In combination with the impact of the 
COVID-19  pandemic  on  occupancy  rates,  Invesque’s  stock  declined  significantly,  which  had  a  material  impact  on  the 
carrying value of the investment and results of operations in 2020. While their stock price and the value of the investment 
increased modestly in 2021, any additional declines in the fair value of Invesque’s common stock could have a significant 
impact on our results of operations and the value of the investment.

The  maritime  transportation  industry  is  highly  competitive  and  fragmented.  Demand  for  shipping  capacity  is  a  function  of 
global economic conditions and the related demand for commodities, production and consumption patterns, and is affected by 
events which interrupt production, trade routes, and consumption. The shipping industry is cyclical with significant volatility 
in charter hire rates and profitability, which can change rapidly. General global economic conditions, along with company 
and industry specific factors, are expected to continue to impact the fair value of our vessels and associated operating results. 
While  there  is  a  current  imbalance  in  supply  and  demand  for  shipping  capacity,  which  led  to  a  cyclical  high  in  dry-bulk 
charter  rates,  a  change  in  those  factors  and/or  changes  in  global  economic  conditions  could  result  in  substantially  lower 
charter rates, which could negatively impact our results of operations and the carrying value of our vessels.

RESULTS OF OPERATIONS

The following is a summary of our consolidated financial results for the year ended December 31, 2021, 2020 and 2019. In 
addition  to  GAAP  results,  management  uses  the  Non-GAAP  measures  Adjusted  net  income,  Adjusted  return  on  average 
equity, Adjusted EBITDA 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. 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.  Adjusted 
EBITDA  is  also  used  in  determining  incentive  compensation  for  the  Company’s  executive  officers.  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, stock-based compensation, net realized and unrealized 
gains (losses), and intangibles amortization associated with purchase accounting. The Company defines Adjusted EBITDA as 
GAAP  net  income  of  the  Company  plus  corporate  interest  expense,  plus  income  taxes,  plus  depreciation  and  amortization 
expense,  less  the  effects  of  purchase  accounting,  plus  non-cash  fair  value  adjustments,  plus  significant  non-recurring 
expenses, and plus unrealized gains (losses) on available for sale securities that are reported in other comprehensive income. 
Adjusted  net  income,  Adjusted  return  on  average  equity  and  Adjusted  EBITDA  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
Adjusted EBITDA 
Book value per share

(1) 

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

Revenues

49

For the Year Ended December 31, 
2020
810,301 
(29,158) 
(0.86) 
0.16 
 (6.4) %

2021
$  1,200,514 
38,132 
$ 
1.09 
$ 
0.16 
$ 
 11.4 %

2019
772,728 
18,361 
0.50 
0.16 
 5.0 %

$ 
$ 
$ 
$ 

$ 
$ 
$ 
$ 

$ 

$ 
$ 

63,869 

 16.5 %

100,776 
11.22 

$ 

$ 
$ 

51,431 

 13.1 %
4,541 
10.90 

$ 

$ 
$ 

27,598 

 6.8 %

68,085 
11.52 

For the year ended December 31, 2021, revenues were $1,200.5 million, which increased $390.2 million, or 48.2% compared 
to  the  prior  year  period,  primarily  driven  by  growth  in  earned  premiums,  net,  and  service  and  administrative  fees  in  the 
insurance  business,  increased  revenues  from  our  dry-bulk  vessels  and  mortgage  servicing  portfolio,  and  net  realized  and 
unrealized gains on Invesque and other investments in 2021 compared to losses in 2020.

For the year ended December 31, 2020, revenues were $810.3 million, which increased $37.6 million, or 4.9% compared to 
the prior year, primarily due to a combination of growth in commercial and service contract lines in our insurance business 
and  revenues  associated  with  our  mortgage  business.  Offsetting  these  increases  were  net  realized  and  unrealized  losses  of 
$83.6 million for the year ended December 31, 2020, on Invesque and other equity securities.

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 relating 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. 

($ in thousands)

For the Year Ended December 31,
2020

2019

2021

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

$ 

$ 

8,885  $ 

(1,817)  $ 

3,736  $ 

(81,813)  $ 

12,189 

(1,200) 

(1) 

Excludes Invesque and Mortgage realized and unrealized gains and losses. The year ended December 31, 2019 includes a $7.6 million gain on sale of our CLO business.

Net Income (Loss) Attributable to common stockholders

For the year ended December 31, 2021, net income attributable to common stockholders was $38.1 million, an increase of 
$67.3 million from a net loss of $29.2 million for the year ended December 31, 2020, primarily driven by net realized and 
unrealized gains on Invesque and other investments in 2021 compared to losses in 2020, in addition to growth in Fortegra’s 
underwriting  and  fee  operations,  increased  revenues  from  our  mortgage  servicing  portfolio  and  improvement  in  dry-bulk 
shipping rates. 

For the year ended December 31, 2020, net loss attributable to common stockholders was $29.2 million, a decrease of $47.5 
million from net income of $18.4 million in 2019. The decrease for the year ended December 31, 2020 was primarily driven 
by the same factors that impacted revenues in the respective periods.

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

Adjusted net income for the year ended December 31, 2021 was $63.9 million, an increase of $12.4 million, or 24.2%, from 
the year ended December 31, 2020. For the year ended December 31, 2021, adjusted return on average equity was 16.5%, as 
compared  to  13.1%  at  December  31,  2020,  with  the  increase  in  both  metrics  driven  by  improved  performance  in  our 
insurance and shipping operations.

Adjusted net income for the year ended December 31, 2020 was $51.4 million, an increase of $23.8 million from 2019. The 
2020 Adjusted return on average equity was 13.1%, as compared to 6.8% in 2019, with the increase in both metrics driven by 
improved performance in our insurance and mortgage operations.

Adjusted EBITDA - Non-GAAP

Adjusted EBITDA for the year ended December 31, 2021 was $100.8 million, an increase of $96.2 million from 2020, driven 
by  realized  and  unrealized  gains  in  2021  compared  to  losses  in  2020  (primarily  Invesque),  in  addition  to  the  improved 
operating performance noted above.

Adjusted EBITDA for the year ended December 31, 2020 was $4.5 million, a decrease of $63.5 million from 2019, which 
was substantially driven by unrealized losses on Invesque and other equity securities.

Book Value per share - Non-GAAP

Total  stockholders’  equity  was  $400.2  million  as  of  December  31,  2021  compared  to  $373.5  million  as  of  December  31, 
2020.  In  the  year  ended  December  31,  2021,  Tiptree  returned  $8.2  million  to  stockholders  through  share  repurchases  and 
dividends paid. Book value per share for the period ended December 31, 2021 was $11.22, an increase from book value per 

50

share of $10.90 as of December 31, 2020. The key drivers of the increase over the past four quarters were income per share 
and the purchase of 0.5 million shares at a discount to book value, partially offset by other comprehensive losses, dividends 
paid of $0.16 per share, and issuance of shares related to warrants and vested subsidiary equity awards.

Total  stockholders’  equity  was  $373.5  million  as  of  December  31,  2020  compared  to  $411.4  million  as  of  December  31, 
2019. In 2020, Tiptree returned $19.3 million to shareholders through share repurchases and dividends paid. Book value per 
share for the period ended December 31, 2020 was $10.90, a decrease from book value per share of $11.52 as of December 
31, 2019. The key drivers of the reduction from the prior year were losses per share and dividends paid of $0.160 per share. 
The decrease was partially offset by the purchase of 2.4 million shares.

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, but not limited to, public company expenses. Mortgage has been 
broken out of Tiptree Capital as a reportable segment because for the years ended December 31, 2021 and 2020 it met the 
quantitative threshold for disclosure. Segments for the year ended December 31, 2019 were conformed to this presentation as 
of December 31, 2020.

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

For the Year Ended December 31, 
2020

2019

2021

$ 

984,130  $ 
111,295 
105,089 
— 

$ 

1,200,514  $ 

691,061  $ 
112,165 
7,075 
— 
810,301  $ 

635,085 
66,121 
71,522 
— 
772,728 

$ 

$ 

$ 

$ 

69,857  $ 
28,407 
17,210 
(50,132) 
65,342  $ 

26,948  $ 
31,102 
(61,242) 
(35,660) 
(38,852)  $ 

66,782  $ 
17,434 
10,763 
(31,110) 
63,869  $ 

43,423  $ 
28,578 
4,497 
(25,067) 
51,431  $ 

37,030 
2,959 
23,391 
(34,241) 
29,139 

32,806 
3,929 
14,083 
(23,220) 
27,598 

(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  business  mixes  and  fee-oriented  services.  Our  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. We are an agent-driven business model, distributing 
our 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. 

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

51

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
Results of Operations - 2021 Compared to 2020

($ 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
Return on average equity
Underwriting ratio
Expense ratio
Combined ratio

Non-GAAP Financial Measures (2):

Adjusted net income
Adjusted return on average equity

For the Year Ended December 31, 

2021

2020

Change

% Change

$ 

$ 

$ 
$ 

685,552 
260,525 
11,784 
17,896 
(2,006) 
10,379 
984,130 

253,473 
73,539 
396,683 
76,552 
17,576 
17,223 
79,227 
914,273 
69,857 

$ 

$ 

$ 
$ 

477,991 
186,973 
21,101 
9,916 
(11,944) 
7,024 
691,061 

178,248 
58,650 
280,210 
65,089 
15,487 
10,835 
55,594 
664,113 
26,948 

$ 

$ 

$ 
$ 

207,561 
73,552 
(9,317) 
7,980 
9,938 
3,355 
293,069 

75,225 
14,889 
116,473 
11,463 
2,089 
6,388 
23,633 
250,160 
42,909 

 43.4 %
 39.3 %
 (44.2) %
 80.5 %
NM %
 47.8 %
 42.4 %

 42.2 %
 25.4 %
 41.6 %
 17.6 %
 13.5 %
 59.0 %
 42.5 %
 37.7 %
 159.2 %

$  2,194,024 

$  1,666,942 

$ 

527,082 

 31.6 %

 17.1 %
 74.7 %
 15.9 %
 90.6 %

 8.1 %
 74.6 %
 16.9 %
 91.5 %

$ 

66,782 

$ 

43,423 

$ 

23,359 

 53.8 %

 22.2 %

 15.2 %

(1) 

(2) 

Net income was $48,755 and $22,821 for the years ended December 31, 2021 and 2020, respectively. 

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

Revenues

Earned Premiums, net

Earned  premiums,  net  represent  the  earned  portion  of  our  gross  written  premiums,  less  the  earned  portion  that  is  ceded  to 
third-party  reinsurers  under  our  reinsurance  agreements,  as  well  as  the  earned  portion  of  our  assumed  premiums.  Our 
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

Service and administrative fees represent the earned portion of our gross written premiums and premium equivalents, which 
is  generated  from  non-insurance  products  including  auto  and  consumer  goods  service  contracts,  motor  club  contracts  and 
other services offered as part of our 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.

Ceding Commissions and Other Revenue

52

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
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 our premium finance product offering.

Net Investment Income

We earn 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. 

Net Realized and Unrealized Gains (Losses)

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, we carry our equity securities at fair value with unrealized gains 
and losses included in this line.

Revenues – 2021 compared to 2020

For the year ended December 31, 2021, total revenues increased 42.4%, to $984.1 million, as compared to $691.1 million for 
the year ended December 31, 2020. Earned premiums, net of $685.6 million increased $207.6 million, or 43.4%, driven by 
growth  in  commercial  and  personal  lines,  including  E&S  insurance  offerings.  Service  and  administrative  fees  of  $260.5 
million increased by 39.3%, driven by growth in auto and consumer goods service contract revenues. Ceding commissions of 
$11.8  million  decreased  by  $9.3  million,  or  44.2%,  driven  by  lower  ceding  fees  as  less  business  was  ceded  in  our  U.S. 
Insurance lines. Other revenues increased by $3.4 million, or 47.8%, driven by growth in our premium finance lines. 

For the year ended December 31, 2021, net investment income of $17.9 million increased $8.0 million from 2020, driven by 
increased interest income from growth in fixed income securities and higher dividends on equity securities. Net realized and 
unrealized losses were $2.0 million, a reduction in losses of $9.9 million, driven by realized and unrealized gains on equity 
securities in 2021, as compared to losses on equity securities and other investments in 2020.

For the year ended December 31, 2021, 28.7% of our revenues were derived from fees that are not solely dependent upon the 
underwriting performance of our insurance products, resulting in more diversified and consistent earnings. For the year ended 
December 31, 2021, 81.7% of our fee-based revenues were generated in non-regulated service companies, with the remainder 
in our regulated insurance companies.

The  combination  of  unearned  premiums  and  deferred  revenues  on  Fortegra’s  balance  sheet  grew  to  $1,658.8  million, 
representing an increase of $399.1 million, or 31.7%, from December 31, 2020 to December 31, 2021 as a result of growth in 
gross written premiums and premium equivalents, primarily related to admitted and E&S insurance lines as well as auto and 
consumer goods service contracts.

Expenses

Underwriting and fee expenses under insurance and service contracts include losses and loss adjustment expenses, member 
benefit claims and commissions expense. 

Net Losses and Loss Adjustment 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. Loss occurrences in our insurance products are characterized by low severity and high frequency. 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.

53

Member Benefit Claims

Member  benefit  claims  represent  the  costs  of  services  and  replacement  devices  incurred  in  auto,  consumer  goods  and 
roadside 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 Expense

Commission expenses reflect commissions we pay retail agents, program administrators and managing general underwriters, 
net  of  ceding  commissions  we  receive  on  business  ceded  under  certain  reinsurance  contracts.  In  addition,  commission 
expenses include premium-related taxes. Commission expenses related to each policy we write 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  which  are  retrospective  commissions  paid  to  agents,  distributors  and  retailers  selling  our  products,  including 
credit insurance policies, auto and consumer goods service contracts and motor club memberships. When claims increase, in 
most cases our 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 our distribution partners.

Operating and Other Expenses

Operating  and  other  expenses  represent  the  general  and  administrative  expenses  of  our  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

Interest  expense  consists  primarily  of  interest  expense  on  our  corporate  revolving  debt,  our  Notes,  our  preferred  trust 
securities due June 15, 2037 (“Preferred Trust Securities”) and asset-based debt for our premium finance business, which is 
non-recourse to Fortegra. 

Depreciation and Amortization

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.

Expenses – 2021 compared to 2020

For the year ended December 31, 2021, net losses and loss adjustment expenses were $253.5 million, member benefit claims 
were $73.5 million and commission expense was $396.7 million, as compared to $178.2 million, $58.7 million and $280.2 
million, respectively, for the year ended December 31, 2020. The increase in net losses and loss adjustment expenses of $75.2 
million, or 42.2%, was driven by growth in U.S. Insurance lines and the impact of prior year development of $2.6 million as a 
result  of  higher-than-expected  claim  severity  from  business  written  by  a  small  group  of  producers  of  our  personal  and 
commercial lines of business. The impact of the prior year development increased our ratio of net losses and loss adjustment 
expenses to earned premiums, net by 0.4%. The increase in member benefit claims of $14.9 million, or 25.4%, was driven by 
growth in auto and consumer goods service contracts. Commission expense increased by $116.5 million, or 41.6%, in line 
with growth in earned premiums, net and service and administrative fees.

For the year ended December 31, 2021, employee compensation and benefits were $76.6 million and other expenses were 
$79.2  million,  as  compared  to  $65.1  million  and  $55.6  million,  respectively,  for  the  year  ended  December  31,  2020. 
Employee  compensation  and  benefits  increased  by  $11.5  million,  or  17.6%,  driven  by  the  acquisition  of  Sky  Auto  and 
investments  in  human  capital  associated  with  our  growth  objectives  in  E&S  and  service  contract  lines.  Other  expenses 
increased  by  $23.6  million,  or  42.5%,  driven  by  increased  marketing  costs  aligned  with  revenue  growth  in  Sky  Auto,  and 
increases in premium taxes, which grew in line with earned premiums. Included in other expenses were $2.2 million and $3.4 

54

million for the years ended December 31, 2021 and 2020, respectively, related to non-recurring professional fees associated 
with preparation of the registration statement for the Fortegra initial public offering which was withdrawn in April 2021, and 
investment banking and legal expenses associated with the acquisition of Smart AutoCare and Sky Auto in January 2020.

For the year ended December 31, 2021, interest expense was $17.6 million as compared to $15.5 million for the year ended 
December  31,  2020.  The  increase  in  interest  expense  of  $2.1  million,  or  13.5%,  was  driven  by  increased  asset-based 
borrowings to support growth in our premium finance lines and higher usage of the revolving working capital facility and 
letters of credit to support net written premium growth.

For the year ended December 31, 2021, depreciation and amortization expense was $17.2 million, including $15.3 million of 
intangible  amortization  related  to  purchase  accounting  associated  with  the  acquisitions  of  Sky  Auto,  Smart  AutoCare  and 
Fortegra. For the year ended December 31, 2020, depreciation and amortization expense was $10.8 million including $9.2 
million of intangible amortization from purchase accounting related to Smart AutoCare and Fortegra.

55

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

Results of Operations - 2020 Compared to 2019

($ 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
Return on average equity
Underwriting ratio
Expense ratio
Combined ratio

Non-GAAP Financial Measures (2):

Adjusted net income
Adjusted return on average equity

For the Year Ended December 31,

2020

2019

Change

% Change

$ 

$ 

$ 
$ 

477,991 
186,973 
21,101 
9,916 
(11,944) 
7,024 
691,061 

178,248 
58,650 
280,210 
65,089 
15,487 
10,835 
55,594 
664,113 
26,948 

$ 

$ 

$ 
$ 

499,108 
106,239 
9,608 
8,667 
6,896 
4,567 
635,085 

151,009 
19,672 
303,057 
49,789 
14,766 
9,105 
50,657 
598,055 
37,030 

$ 

$ 

$ 
$ 

(21,117) 
80,734 
11,493 
1,249 
(18,840) 
2,457 
55,976 

27,239 
38,978 
(22,847) 
15,300 
721 
1,730 
4,937 
66,058 
(10,082) 

 (4.2) %
 76.0 %
 119.6 %
 14.4 %
NM %
 53.8 %
 8.8 %

 18.0 %
 198.1 %
 (7.5) %
 30.7 %
 4.9 %
 19.0 %
 9.7 %
 11.0 %
 (27.2) %

$  1,666,942 

$  1,297,042 

$ 

369,900 

 28.5 %

 8.1 %
 74.6 %
 16.9 %
 91.5 %

 10.7 %
 76.5 %
 15.9 %
 92.4 %

$ 

43,423 

$ 

32,806 

$ 

10,617 

 32.4 %

 15.2 %

 12.3 %

(1) 

(2) 

Net income was $22,821 and $27,160 for the year ended December 31, 2020 and 2019, respectively. 

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

Revenues – 2020 compared to 2019

For the year ended December 31, 2020, total revenues increased 8.8%, to $691.1 million, as compared to $635.1 million for 
the  year  ended  December  31,  2019.  Earned  premiums,  net  of  $478.0  million  decreased  $21.1  million,  or  4.2%,  driven  by 
increased ceding of credit insurance and collateral protection premiums, and increased credit insurance cancellations driven 
by  COVID-19  stimulus  payments  to  consumers.  This  was  partially  offset  by  growth  in  commercial,  service  contract  and 
niche  personal  lines  programs.  Service  and  administrative  fees  of  $187.0  million  increased  by  76.0%  driven  by  our 
acquisition  of  Smart  AutoCare  and  growth  in  service  contract  revenues.  Excluding  Smart  AutoCare,  service  and 
administrative  fees  increased  by  11.7%,  driven  by  growth  in  our  consumer  goods  and  roadside  service  contracts.  Ceding 
commissions of $21.1 million increased by $11.5 million, or 119.6%, driven by growth in commercial lines and higher fees 
associated  with  the  increase  in  ceded  premiums  in  credit  insurance  and  collateral  protection  programs.  Other  revenues 
increased by $2.5 million, or 53.8%, driven by growth in our premium finance lines.

For the year ended December 31, 2020, 31.1% of our revenues were derived from fees that are not solely dependent upon the 
underwriting performance of our insurance products, resulting in more diversified and consistent earnings. For the year ended 
December 31, 2020, 79.3% of our fee-based revenues were generated in non-regulated service companies, with the remainder 
in our regulated insurance companies.

For the year ended December 31, 2020, net investment income was $9.9 million driven by interest income on fixed income 
securities  and  dividends  on  equity  securities.  Net  realized  and  unrealized  losses  were  $11.9  million,  a  decline  of  $18.8 

56

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
million, driven by realized and unrealized losses on equity securities in 2020, as compared to gains on equity securities and 
other investments in 2019.

Expenses – 2020 compared to 2019

For the year ended December 31, 2020, net losses and loss adjustment expenses were $178.2 million, member benefit claims 
were $58.7 million and commission expense was $280.2 million, as compared to $151.0 million, $19.7 million and $303.1 
million, respectively, for the year ended December 31, 2019. The increase in net losses and loss adjustment expenses of $27.2 
million, or 18.0%, was driven by growth in our U.S. Insurance business and the impact of prior year development of $5.4 
million related to higher than expected claims frequency in certain programs associated with a small group of producers. The 
impact of the prior year development increased our ratio of net losses and loss adjustment expenses to earned premiums, net 
by  1.1%.  The  increase  in  member  benefit  claims  of  $39.0  million,  or  198.1%,  was  driven  by  the  acquisition  of  Smart 
AutoCare.  Commission  expense  declined  by  $22.8  million,  or  7.5%,  driven  by  a  decline  in  retrospective  commission 
payments, largely offsetting the increase in net losses and loss adjustment expense.

For the year ended December 31, 2020, employee compensation and benefits were $65.1 million and other expenses were 
$55.6  million,  as  compared  to  $49.8  million  and  $50.7  million,  respectively,  for  the  year  ended  December  31,  2019. 
Employee compensation and benefits increased by $15.3 million, or 30.7%, driven by the acquisition of Smart AutoCare and 
investments  in  human  capital  associated  with  our  growth  objectives  in  E&S  and  service  contract  lines.  Other  expenses 
increased by $4.9 million, or 9.7%, driven by increases in acquisition related expenses, and premium taxes, which grew in 
line with premiums. Included in other expenses were $3.4 million and $2.0 million for the years ended December 31, 2020 
and 2019, respectively, related to non-recurring professional fees associated with investment banking and legal expenses for 
our acquisitions of Smart AutoCare and Sky Auto.

For the year ended December 31, 2020, interest expense was $15.5 million as compared to $14.8 million for the year ended 
December 31, 2019. The increase in interest expense of $0.7 million, or 4.9%, was driven by higher outstanding asset-based 
debt for our premium finance business, partially offset by decreases in LIBOR over 2020.

For the year ended December 31, 2020, depreciation and amortization expense was $10.8 million, including $9.2 million of 
intangible amortization related to purchase accounting associated with the acquisitions of both Smart AutoCare and Fortegra, 
as  compared  to  $9.1  million  and  $7.5  million  of  intangible  amortization  from  purchase  accounting  related  to  Fortegra, 
respectively, for 2019.

Key Performance Metrics

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

Gross Written Premiums and Premium Equivalents

Gross written premiums and premium equivalents represent total gross written premiums from insurance policies and service 
contracts  issued,  as  well  as  premium  finance  volumes  during  a  reporting  period.  They  represent  the  volume  of  insurance 
policies  written  or  assumed  and  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 
service and administrative contract volumes to gross written premiums. 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.

The below table shows gross written premiums and premium equivalents by business mix for the following periods:

57

($ in thousands)

U.S. Insurance
U.S. Warranty Solutions
Europe Warranty Solutions
Total

$ 

$ 

For the Year Ended December 31,
Gross Written Premiums and Premium 
Equivalents
2020
1,063,743  $ 
549,983 
53,216 
1,666,942  $ 

2021
1,438,393  $ 
652,052 
103,579 
2,194,024  $ 

965,544 
297,289 
34,209 
1,297,042 

2019

Total gross written premiums and premium equivalents for the year ended December 31, 2021 were $2.2 billion as compared 
to $1.7 billion in 2020. The growth of $527.1 million, or 31.6%, is driven by a combination of factors including Fortegra’s 
growing distribution partner network, expanding admitted and E&S insurance lines, and increasing market penetration in the 
service  contract  sector  through  the  acquisitions  of  Smart  AutoCare  (January  2020)  and  Sky  Auto  (December  2020). 
Additionally,  certain  retail-oriented  distribution  partners  were  impacted  by  COVID-19  shutdowns  in  2020,  providing  for  a 
more favorable period over period comparison.

We  believe  the  continued  growth  in  commercial  E&S  and  service  contract  lines  will  result  in  increased  gross  written 
premiums and premium equivalents, and therefore growth in unearned premiums and deferred revenues on the balance sheet. 
The  growth  in  gross  written  premiums  and  premium  equivalents,  combined  with  higher  retention  in  select  products,  has 
resulted in an increase of $399.1 million, or 31.7%, in Fortegra’s unearned premiums and deferred revenue on the balance 
sheet. As of December 31, 2021, Fortegra’s unearned premiums and deferred revenues were $1,658.8 million, as compared to 
$1,259.7 million as of December 31, 2020.

Total gross written premiums and premium equivalents for the year ended December 31, 2020 were $1.7 billion as compared 
to  $1.3  billion  in  2019.  U.S.  Insurance  lines  increased  by  $98.2  million  for  the  year  ended  December  31,  2019,  or  10.2%, 
driven by growth in commercial, service contract insurance and collateral protection lines. U.S. Warranty Solutions increased 
by $252.7 million for the year ended December 31, 2020, or 85.0%, driven primarily by the acquisition of Smart AutoCare 
and growth in premium finance volumes. Europe Warranty Solutions increased by $19.0 million, or 55.6%, driven by growth 
in auto and consumer goods service contracts.

The  growth  in  gross  written  premiums  and  premium  equivalents,  combined  with  higher  risk  retention  in  select  products, 
increased  unearned  premiums  and  deferred  revenue  on  Fortegra’s  balance  sheet  by  $410.4  million,  or  48.3%.  As  of 
December  31,  2020,  Fortegra’s  unearned  premiums  and  deferred  revenues  were  $1,259.7  million,  as  compared  to  $849.3 
million as of December 31, 2019. 

Combined Ratio, Underwriting Ratio and Expense Ratio

Combined ratio is an operating measure, which equals the sum of the underwriting ratio and the expense ratio. Underwriting 
ratio is the ratio of the GAAP line items net losses and loss adjustment expenses, member benefit claims and commission 
expense to earned premiums, net, service and administrative fees and ceding commissions and other revenue. Expense ratio is 
the  ratio  of  the  GAAP  line  items  employee  compensation  and  benefits  and  other  underwriting,  general  and  administrative 
expenses to earned premiums, net, service and administrative fees and ceding commissions and other revenue.

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.

The combined ratio was 90.6% for the year ended December 31, 2021, which consisted of an underwriting ratio of 74.7% and 
an expense ratio of 15.9%, as compared to 91.5%, 74.6% and 16.9%, respectively, for the year ended December 31, 2020. 
The improvement in the combined ratio year over year is primarily driven by the continued scalability of the technology and 
shared service platform, decreasing the expense ratio, while maintaining consistent underwriting performance. Our focus on 
underwriting  expertise,  A.I.  driven  lead  generation,  and  technology-enhanced  administration  improves  productivity,  lowers 
administrative costs and results in agent relationships sustained over the long-term. 

The combined ratio was 91.5% for the year ended December 31, 2020, which consisted of an underwriting ratio of 74.6% and 
an expense ratio of 16.9%, as compared to 92.4%, 76.5% and 15.9%, respectively, for the year ended December 31, 2019. 

58

 
 
 
 
 
 
The improvement in the combined ratio and underwriting ratio from 2019 to 2020 was primarily due to the shift in business 
mix as the result of the growth in commercial and service contract lines, while the increase in the expense ratio was primarily 
driven by the impact of purchase accounting on the recognition of revenues and expenses associated with our acquisition of 
Smart AutoCare.

Return on Average Equity

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. 

Return  on  average  equity  was  17.1%  for  the  year  ended  December  31,  2021,  as  compared  to  8.1%,  for  the  year  ended 
December 31, 2020, with the increase driven by growth in underwriting and fee revenues, improvement in the combined ratio 
and realized and unrealized gains in 2021, as compared to realized and unrealized losses in 2020.

Return  on  average  equity  was  8.1%  for  the  year  ended  December  31,  2020,  as  compared  to  10.7%,  for  the  year  ended 
December 31, 2019, with the decline driven by realized and unrealized losses in 2020, as compared to realized and unrealized 
gains in 2019, partially offset by improvement in revenues associated with underwriting activities.

Non-GAAP Financial Measures

Underwriting and Fee Revenues and Underwriting and Fee Margin - Non-GAAP(1)

In order to better explain to investors the underwriting performance 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  retrospective  commission  agreements  with  our  agents  (e.g.,  commissions  paid  are  adjusted  based  on  the  actual 
underlying  losses  incurred),  which  mitigate  our  risk.  Period-over-period  comparisons  of  revenues  and  expenses  are  often 
impacted by the agents and their PORC’s choice as to their risk retention appetite, specifically earned premiums, net, service 
and administration fees, ceding commissions, and other revenue, all components of revenue, and losses and loss adjustment 
expenses, member benefit claims, and commissions paid to our agents and reinsurers. 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 total revenues excluding net investment income, net realized and unrealized gains 
(losses).  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 and unrealized 
gains (losses), 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.

The below table shows underwriting and fee revenues and underwriting and fee margin by business mix for the following 
periods:

($ in thousands)

U.S. Insurance
U.S. Warranty Solutions
Europe Warranty Solutions
Total

For the Year Ended December 31, 

Underwriting and Fee Revenues (1)
2019
2020
2021
$ 525,554 
$ 507,537 
$ 690,154 
  87,130 
  162,900 
  230,942 
6,834 
  22,652 
  47,144 
$ 619,518 
$ 693,089 
$ 968,240 

Underwriting and Fee Margin (1)
2019
2020
2021
$ 105,492 
$ 106,763 
$ 141,258 
  37,478 
  61,722 
  90,255 
2,808 
7,496 
  13,032 
$ 145,778 
$ 175,981 
$ 244,545 

(1) 

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

Underwriting and fee revenues were $968.2 million for the year ended December 31, 2021, as compared to $693.1 million, 

59

 
 
 
for  the  year  ended  December  31,  2020.  Total  underwriting  and  fee  revenues  were  up  $275.2  million,  or  39.7%,  driven  by 
growth  in  all  product  lines.  U.S.  Insurance  revenues  increased  $182.6  million,  or  36.0%,  driven  by  growth  in  E&S 
commercial, collateral protection and credit insurance lines. The increase in U.S. Warranty Solutions was $68.0 million, or 
41.8%,  driven  by  growth  in  auto,  consumer  goods,  and  premium  finance.  Europe  Warranty  Solutions  increased  by  $24.5 
million, or 108.1%, driven by growth in auto and consumer goods service contracts.

Underwriting and fee margin was $244.5 million for the year ended December 31, 2021 as compared to $176.0 million for 
the year ended December 31, 2020, representing an increase of $68.6 million, or 39.0%, driven by growth in all product lines. 
U.S.  Insurance  grew  by  $34.5  million,  or  32.3%,  as  the  underwriting  ratio  was  consistent  year-over-year  at  79.5%  while 
revenues  increased.  U.S.  Warranty  Solutions  increased  by  $28.5  million,  or  46.2%,  driven  by  the  growth  in  revenues  and 
improvement in the underwriting ratio. Europe Warranty Solutions increased by $5.5 million, or 73.9%, driven by growth in 
auto and consumer goods service contracts in those markets.

Underwriting and fee revenues were $693.1 million for the year ended December 31, 2020, as compared to $619.5 million, 
for  the  year  ended  December  31,  2019.  Total  underwriting  and  fee  revenues  were  up  $73.6  million,  or  11.9%,  driven  by 
growth in U.S. and Europe Warranty Solutions, partially offset by a decline in U.S. Insurance. The decrease in U.S. Insurance 
was $18.0 million, or 3.4%, driven by increased ceded premiums and cancellations from the impacts of stimulus related to 
COVID-19  in  our  credit  insurance  and  collateral  protection  lines.  This  was  partially  offset  by  growth  in  commercial  and 
niche personal lines. The increase in U.S. Warranty Solutions was $75.8 million, or 87.0%, driven by the acquisition of Smart 
AutoCare and growth in auto, consumer goods, and premium finance. Europe Warranty Solutions increased by $15.8 million, 
or 231.5%, driven by growth in auto and consumer goods service contracts.

Underwriting and fee margin was $176.0 million for the year ended December 31, 2020 as compared to $145.8 million for 
the year ended December 31, 2019. Total underwriting and fee margin was up $30.2 million, or 20.7%, driven by growth in 
U.S. and Europe Warranty Solutions. U.S. Insurance was flat to prior year as the growth in commercial and niche personal 
lines  offset  the  impacts  of  COVID-19  on  our  credit  insurance  and  collateral  protection  lines.  U.S.  Warranty  Solutions 
increased by $24.2 million, or 64.7%, driven by the acquisition of Smart AutoCare and growth in auto, consumer goods, and 
premium  finance  lines.  Europe  Warranty  Solutions  increased  by  $4.7  million,  or  167.0%,  driven  by  growth  in  auto  and 
consumer goods service contracts in those markets.

Adjusted Net Income and Adjusted Return on Average Equity

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. 

Management uses both measures to assess the on-going performance of our operations. See “—Non-GAAP Reconciliations” 
for a reconciliation of adjusted net income and adjusted return on average equity to income before taxes and adjusted return 
on average equity.

For the year ended December 31, 2021, adjusted net income and adjusted return on average equity were $66.8 million and 
22.2%,  respectively,  as  compared  to  $43.4  million  and  15.2%,  respectively,  for  the  year  ended  December  31,  2020.  The 
improvement in metrics was driven by the growth in revenues and improvement in the combined ratio.

For the year ended December 31, 2020, adjusted net income and adjusted return on average equity were $43.4 million and 
15.2%,  respectively,  as  compared  to  $32.8  million  and  12.3%,  respectively,  for  the  year  ended  December  31,  2019.  The 
improvement in both of these metrics was driven by the growth in commercial, service contracts and niche personal lines. See 
“—Non-GAAP Reconciliations” for a reconciliation of adjusted net income and adjusted return on average equity to income 
before taxes and adjusted return on average equity.

Net Investment Income and Net Realized and Unrealized Gains (Losses) on Investments

60

Our 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. Our investment strategy is designed to 
achieve  attractive  risk-adjusted  returns  across  select  asset  classes,  sectors  and  geographies  while  maintaining  adequate 
liquidity  to  meet  our  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 Available for Sale (“AFS”) securities impact AOCI.

Our net investment income includes interest and dividends, net of investment expenses, on our invested assets. We report net 
realized and unrealized gains and losses on our investments separately from our net investment income.

For the year ended December 31, 2021, net investment income was $17.9 million compared to $9.9 million in 2020 with the 
increase driven by growth in investments, resulting in incremental interest income on fixed income securities and dividends 
on equity securities. Net realized and unrealized losses were $2.0 million, a decline of $9.9 million, driven by a reduction in 
realized and unrealized losses on equity securities from 2020 to 2021.

For the year ended December 31, 2020, net investment income was $9.9 million driven by growth in investments, resulting in 
incremental interest income on fixed income securities and dividends on equity securities. Net realized and unrealized losses 
were  $11.9  million,  a  decline  of  $18.8  million,  driven  by  realized  and  unrealized  losses  on  equity  securities  in  2020 
(primarily Invesque), as compared to gains on equity securities and other investments in 2019.

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,  2021,  Tiptree  Capital  -  Other  includes  our  Invesque  shares,  maritime  transportation  operations,  and  the 
mortgage operations of Luxury, which is classified as held for sale on the balance sheet. 

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. The Company is also an approved issuer and servicer 
for  Ginnie  Mae.  The  Company  originates  residential  mortgage  loans  through  its  retail  distribution  channel  (directly  to 
consumers) in 39 states and the District of Columbia as of December 31, 2021.

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

61

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
Adjusted return on average equity

For the Year Ended December 31, 

2021

2020

2019

$ 

$ 

$ 

$ 
$ 

92,307 
18,988 
111,295 

56,819 
1,168 
885 
24,016 
82,888 
28,407 

$ 

$ 

$ 

$ 
$ 

96,590 
15,575 
112,165 

58,226 
1,188 
956 
20,693 
81,063 
31,102 

$ 

$ 

$ 

$ 
$ 

53,815 
12,306 
66,121 

42,411 
1,790 
809 
18,152 
63,162 
2,959 

$  1,608,311 

$  1,658,126 

$  1,142,642 

 5.6 %
 38.9 %

 6.3 %
 50.9 %

 4.7 %
 7.1 %

$ 

17,434 

$ 

28,578 

$ 

 28.8 %

 60.5 %

3,929 
 12.0 %

(1) 

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

Revenues

Net Realized and Unrealized Gains (Losses)

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

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.

Revenues – 2021 compared to 2020 and 2020 compared to 2019

For  the  year  ended  December  31,  2021,  $1,608.3  million  of  loans  were  funded,  compared  to  $1,658.1  million  for  2020,  a 
decrease of $49.8 million, or 3.0%. Origination volumes in 2021 and 2020 were primarily attributed to the lower interest rate 
environment and home price appreciation in the United States. Gain on sale margins decreased to 5.6% for the year ended 
December 31, 2021, down approximately 70 basis points from 6.3% for the year ended December 31, 2020. Net realized and 
unrealized gains for the year ended December 31, 2021 were $92.3 million, compared to $96.6 million for 2020, a decrease 
of $4.3 million or 4.4%. The primary driver of decreased gain on sale revenues were the decline in volumes and gain on sale 
margins,  partially  offset  by  positive  fair  value  adjustments  in  mortgage  servicing  rights  of  $5.8  million  as  interest  rates 
increased from the year ended December 31, 2020. Other revenue for the year ended December 31, 2021 was $19.0 million, 
compared to $15.6 million for 2020, an increase of $3.4 million, or 21.9%, driven primarily by higher servicing fees from an 
increase in loans serviced. As of December 31, 2021, the mortgage servicing asset recorded in other assets on the balance 

62

 
 
 
 
 
 
 
 
 
 
 
 
sheet was $29.8 million, an increase from $14.8 million as of December 31, 2020.

For the year ended December 31, 2020, $1,658.1 million of loans were funded, compared to $1,142.6 million for 2019, an 
increase  of  $515.5  million,  or  45.1%.  The  increase  in  origination  volumes  is  primarily  attributed  to  the  lower  interest  rate 
environment  and  rising  home  prices  in  2020  compared  to  2019.  Gain  on  sale  margins  also  increased  to  6.3%  for  the  year 
ended December 31, 2020, up 165 basis points from 4.7% for the year ended December 31, 2019. Net realized and unrealized 
gains (losses) for the year ended December 31, 2020 were $96.6 million, compared to $53.8 million for 2019, an increase of 
$42.8 million or 79.5%. The primary drivers of increased gains on sale were increases in origination volumes and gains on 
sale margins, partially offset by negative fair value adjustments in our mortgage servicing rights of $4.0 million as interest 
rates declined. Other revenue for the year ended December 31, 2020 was $15.6 million, compared to $12.3 million for 2019, 
an increase of $3.3 million or 26.8%, driven by increased loan origination volumes and servicing fees. As of December 31, 
2020,  the  mortgage  servicing  asset  recorded  in  other  assets  on  the  balance  sheet  was  $14.8  million,  an  increase  from  $8.8 
million as of December 31, 2019.

Expenses

Employee Compensation and Benefits

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

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 and Amortization

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

Other Expenses

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.

Expenses – 2021 compared to 2020 and 2020 compared to 2019

For the year ended December 31, 2021, employee compensation and benefits was $56.8 million, compared to $58.2 million 
in 2020, a decrease of $1.4 million or 2.4%. This decrease was driven primarily by reduced commissions on lower origination 
volumes. For the year ended December 31, 2021 and 2020, interest expense and depreciation and amortization expense were 
both flat, at $1.2 million and $0.9 million, respectively. For the year ended December 31, 2021, other expenses were $24.0 
million,  compared  to  $20.7  million  in  2020  with  the  $3.3  million  increase  driven  by  increased  loan  origination  expenses, 
including marketing costs.

For the year ended December 31, 2020, employee compensation and benefits was $58.2 million, compared to $42.4 million 
in  2019,  an  increase  of  $15.8  million  or  37.3%.  This  increase  was  driven  primarily  by  increased  commissions  on  higher 
origination  volumes,  in  addition  to  increased  incentive  compensation.  For  the  year  ended  December  31,  2020,  interest 
expense was $1.2 million, compared to $1.8 million in 2019, a decrease of $0.6 million, or 33.3%. This is due to the reduced 
interest rate environment decreasing our cost of funds, partially offset by higher loan volumes. For the year ended December 
31, 2020, depreciation and amortization expense was $1.0 million, compared to $0.8 million for 2019, up $0.2 million, due to 
purchases  of  fixed  assets.  For  the  year  ended  December  31,  2020,  other  expenses  were  $20.7  million,  compared  to  $18.2 
million in 2019, driven by increased loan origination expenses, including marketing costs, and rent. 

Income (loss) before taxes

63

Income  before  taxes  for  the  year  ended  December  31,  2021  was  $28.4  million,  compared  to  income  before  taxes  of  $31.1 
million  in  2020.  The  primary  driver  of  the  decrease  was  a  decline  in  margins  partially  offset  by  higher  servicing  fees 
attributable to the larger servicing portfolio, in addition to positive fair value adjustments on the mortgage servicing rights 
asset, as compared to 2020.

Income  before  taxes  for  the  year  ended  December  31,  2020  was  $31.1  million,  compared  to  $3.0  million  in  2019.  The 
primary  driver  of  the  increase  was  the  increase  in  revenue  noted  above,  partially  offset  by  higher  compensation  and  other 
costs associated with the improved financial performance. 

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
Other (1)
Total

For the Year Ended December 31, 

2021

Total revenue
2020

2019

Income (loss) before taxes
2020

2019

2021

$ 

$ 

3,091  $ 
35,562 
66,436 
105,089  $ 

(65,123)  $ 
22,697 
49,501 
7,075  $ 

9,140 
16,591 
45,791 
71,522 

$ 

$ 

3,091  $ 
11,635 
2,484 
17,210  $ 

(65,123)  $ 
1,493 
2,388 
(61,242)  $ 

9,140 
1,610 
12,641 
23,391 

(1) 

Includes our held for sale mortgage originator (Luxury), asset management, and certain intercompany elimination transactions.

Revenues

Tiptree  Capital  -  Other  earns  revenues  from  the  following  sources:  net  interest  income;  revenues  on  our  held  for  sale 
mortgage originator; realized and unrealized gains and losses on the Company’s investment holdings (primarily Invesque); 
and charter revenue from vessels within the Company’s maritime transportation operations. 

Revenues for the year ended December 31, 2021 were $105.1 million compared to $7.1 million for 2020. The primary driver 
of  the  change  in  revenues  for  the  year  ended  December  31,  2021  was  unrealized  gains  on  Invesque  in  2021  compared  to 
unrealized losses in 2020, partially offset by the suspension of its monthly dividend payment in April 2020, increased dry-
bulk charter rates earned by the maritime transportation business, and growth in mortgage gain on sale revenues in the held 
for sale mortgage originator.

Revenues for the year ended December 31, 2020 were $7.1 million, compared to $71.5 million for 2019. The primary driver 
of revenues for the year ended December 31, 2020 were unrealized losses of $67.7 million on Invesque and the suspension of 
its monthly dividend payment, offset by a full year of tanker operations in our maritime transportation business and growth in 
mortgage gain on sale revenues in our held for sale mortgage originator.

Income (loss) before taxes

The income before taxes from Tiptree Capital - Other for the year ended December 31, 2021 was $17.2 million, compared to 
a loss before taxes of $61.2 million in 2020. The primary driver of the increase was unrealized gains in 2021 compared to 
losses  in  2020  on  our  investment  in  Invesque,  in  addition  to  increased  income  before  taxes  in  our  maritime  transportation 
business due to a rise in dry-bulk charter rates.

The loss before taxes from Tiptree Capital - Other for the year ended December 31, 2020 was $61.2 million, compared to 
income  of  $23.4  million  in  2019.  The  primary  drivers  of  the  decrease  were  unrealized  losses  and  discontinued  dividend 
income on our investment in Invesque. Non-recurrence of the gain on sale of the management contracts and related assets for 
the CLOs managed in our asset management business in 2019 also drove the 2020 decline in income before taxes.

64

 
 
 
 
 
 
 
 
 
 
 
 
Adjusted net income - Non-GAAP(1)

($ in thousands)

Senior living (Invesque)
Maritime transportation
Other
Total 

Year Ended December 31,
2020

2019

2021

$ 

$ 

—  $ 

10,713 
50 
10,763  $ 

2,001  $ 
2,291 
205 
4,497  $ 

8,004 
1,695 
4,384 
14,083 

(1) 

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

Adjusted net income increased to $10.8 million for the year ended December 31, 2021 compared to $4.5 million in 2020. The 
increase was driven by improvement in maritime transportation operations from higher dry-bulk charter rates, partially offset 
by the impact of the discontinuation of the Invesque dividend in April 2020.

Adjusted net income decreased to $4.5 million for the year ended December 31, 2020 compared to $14.1 million in 2019. The 
key driver of the decrease was the dividend income on our investment in Invesque was discontinued in April 2020. See “— 
Non-GAAP Reconciliations” for a reconciliation to GAAP net income.

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

For the Year Ended December 31, 
2020

2019

2021

$ 

$ 

7,406  $ 
20,654 
10,032 
805 
11,235 
50,132  $ 

7,718  $ 
7,477 
10,016 
807 
9,642 
35,660  $ 

6,542 
9,323 
6,292 
652 
11,432 
34,241 

Corporate expenses include expenses of the holding company for interest expense, employee compensation and benefits, 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,  was  $28.1  million  for  the  year  ended 
December 31, 2021, compared to $15.2 million for 2020, driven by an increase in performance related employee incentive 
compensation.  Of  the  incentive  compensation  expense,  $8.6  million  was  related  to  stock-based  compensation  expense  in 
2021 primarily driven by the increase in Tiptree’s stock price, compared to $3.2 million in 2020. Interest expense for the year 
ended  December  31,  2021  and  2020  was  $10.0  million.  As  of  December  31,  2021,  the  outstanding  borrowing  was  $114.1 
million, compared to $120.3 million at December 31, 2020. Other expenses of $11.2 million increased by $1.6 million from 
the year ended December 31, 2020, primarily driven by $2.2 million of non-recurring professional and legal fees associated 
with  preparation  of  the  registration  statement  for  the  potential  Fortegra  initial  public  offering  in  2021  (which  registration 
statement  has  been  withdrawn),  compared  to  $0.8  million  of  non-recurring  debt  extinguishment  fees  associated  with  the 
refinancing of the corporate credit facility and acquisition-related legal fees in the prior year.

Employee  compensation  and  benefits,  including  incentive  compensation  expense,  was  $15.2  million  for  the  year  ended 
December  31,  2020  compared  to  $15.9  million  for  2019,  driven  primarily  by  a  reduction  in  employee  incentive 
compensation.  Interest  expense  for  the  year  ended  December  31,  2020  was  $10.0  million,  up  from  $6.3  million  in  2019, 
driven by a higher average outstanding balance during 2020 associated with our acquisition of Smart AutoCare in January 
2020. As of December 31, 2020, the outstanding borrowing was $120.3 million, compared to $68.2 million at December 31, 
2019.

Provision for Income Taxes

65

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
The  total  income  tax  expense  of  $21.3  million  for  the  year  ended  December  31,  2021,  and  the  total  income  tax  benefit  of 
$13.6  million  for  the  year  ended  December  31,  2020  and  total  income  tax  expense  of  $9.0  million  for  the  year  ended 
December 31, 2019 are reflected as components of net income (loss). 

For the year ended December 31, 2021, the Company’s effective tax rate was equal to 32.6%. The effective rate for the year 
ended December 31, 2021 was higher than the U.S. statutory income tax rate of 21.0% primarily from the impact of state 
taxes  and  non-deductible  compensation,  partially  offset  by  the  effect  of  stock  based  compensation.  For  the  year  ended 
December 31, 2020, the Company’s effective tax rate was equal to 35.1%. The effective rate for the year ended December 31, 
2020  was  higher  than  the  U.S.  federal  statutory  income  tax  rate  of  21.0%,  primarily  from  the  impact  of  expected  refunds 
arising from the CARES Act. For the year ended December 31, 2019, the Company’s effective tax rate was equal to 31.0%. 
The effective rate for the year ended December 31, 2019 was higher than the U.S. federal statutory income tax rate of 21.0%, 
primarily from the impact of the non-recurring return-to-provision, as well as ongoing state and foreign taxes. 

On March 27, 2020, the CARES Act was enacted, implementing numerous changes to tax law including temporary changes 
regarding the prior and future utilization of net operating losses. During the year ended December 31, 2020, the Company 
recorded a $7.3 million tax benefit related to the ability to carry back net operating losses to prior periods under the CARES 
Act, resulting in a decrease of our deferred tax asset of $16.8 million and increase to our current receivable of $24.1 million.

Balance Sheet Information

Tiptree’s  total  assets  were  $3,599.1  million  as  of  December  31,  2021,  compared  to  $2,995.8  million  as  of  December  31, 
2020. The $603.4 million increase in assets is primarily attributable to the growth in the Insurance segment. 

Total  stockholders’  equity  was  $400.2  million  as  of  December  31,  2021,  compared  to  $373.5  million  as  of  December  31, 
2020, primarily driven by net income for year ended December 31, 2021, partially offset by dividends. As of December 31, 
2021, there were 34,124,153 shares of common stock outstanding as compared to 32,682,462 as of December 31, 2020.

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

($ in thousands)
Total assets

Corporate debt
Asset based debt

Tiptree Inc. stockholders’ equity
Non-controlling interests - Other
Total stockholders’ equity

As of December 31, 2021

Tiptree Capital

Insurance

Mortgage

Other

Corporate

3,002,152  $ 

201,134  $ 

384,564  $ 

11,297  $ 

162,160  $ 
42,310 

292,865  $ 
11,066 
303,931  $ 

—  $ 

—  $ 

72,518 

13,600 

59,237  $ 
1,169 
60,406  $ 

117,984  $ 
3,930 
121,914  $ 

114,063  $ 
— 

(87,132)  $ 
1,062 
(86,070)  $ 

$ 

$ 

$ 

$ 

Total
3,599,147 

276,223 
128,428 

382,954 
17,227 
400,181 

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, adjusted return on average equity and Adjusted EBITDA as measures of operating performance and as part of our 
resource and capital allocation process, to assess comparative returns on invested capital. Adjusted EBITDA is also used in 
determining  incentive  compensation  for  the  Company’s  executive  officers.  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, Adjusted EBITDA, 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. 

66

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

The  following  tables  present  revenue  and  expenses  by  business  mix.  We  generally  manage  exposure  to  underwriting  risks 
written by using both reinsurance (e.g., quota share and excess of loss) and retrospective commission agreements with our 
partners (e.g., commissions paid are adjusted based on the actual underlying losses incurred), which mitigates Fortegra’s risk. 
Period-over-period comparisons of revenues and expenses are often impacted by the PORCs and distribution partners’ choice 
as  to  whether  to  retain  risk,  specifically  service  and  administration  fees  and  ceding  commissions,  both  components  of 
revenue, and policy and contract benefits and commissions paid to our partners and reinsurers. Generally, when losses are 
incurred, the risk which is retained by our partners and reinsurers is reflected in a reduction in commissions paid. In order to 
better explain to investors the underwriting performance 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.

Underwriting and Fee Revenues — Non-GAAP

We define underwriting and fee revenues as total revenues from the Insurance segment excluding net investment income and 
net realized and unrealized gains (losses). Underwriting and fee revenues represents revenues generated by underwriting and 
fee-based  operations  and  allows  us  to  evaluate  the  Company’s  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)

Underwriting and fee revenues

Underwriting and Fee Margin — Non-GAAP

For the Year Ended December 31,
2020

2019

2021

$ 

$ 

984,130  $ 
(17,896) 
2,006 
968,240  $ 

691,061  $ 
(9,916) 
11,944 
693,089  $ 

635,085 
(8,667) 
(6,896) 
619,522 

We  define  underwriting  and  fee  margin  as  income  before  taxes  from  the  Insurance  segment,  excluding  net  investment 
income, net realized and unrealized gains (losses), 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  lines.  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  the  Company’s  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 
business  mix.  Underwriting  and  fee  margin  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.

($ in thousands)

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

Underwriting and fee margin

Adjusted Net Income — Non-GAAP

For the Year Ended December 31, 
2020

2019

2021

$ 

$ 

69,857  $ 
(17,896)   
2,006 
17,223 
17,576 
76,552 
79,227 
244,545  $ 

26,948  $ 
(9,916) 
11,944 
10,835 
15,487 
65,089 
55,594 
175,981  $ 

37,030 
(8,667) 
(6,896) 
9,105 
14,766 
49,789 
50,657 
145,784 

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.  We  use  adjusted  net  income  as  an  internal  operating  performance  measure  in  the 

67

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
management  of  business  as  part  of  our  capital  allocation  process.  We  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 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.

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,  and 
Smart  AutoCare  and  Sky  Auto  in  2020.  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. 
We use adjusted return on average equity as an internal performance measure in the management of our operations because 
we believe it gives our management and other users of our financial information useful insight into our results of operations 
and our underlying business performance. 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.

For the Year Ended December 31, 2021

Tiptree Capital

($ in thousands)
Income (loss) before taxes
Less: Income tax (benefit) expense
Less: Net realized and unrealized gains (losses)
Plus: Intangibles amortization (1)
Plus: Stock-based compensation expense
Plus: Non-recurring expenses
Plus: Non-cash fair value adjustments
Less: Tax on adjustments
Adjusted net income

Adjusted net income
Average stockholders’ equity

Adjusted return on average equity

($ in thousands)
Income (loss) before taxes
Less: Income tax (benefit) expense
Less: Net realized and unrealized gains (losses)
Plus: Intangibles amortization (1)
Plus: Stock-based compensation expense
Plus: Non-recurring expenses
Plus: Non-cash fair value adjustments
Less: Tax on adjustments
Adjusted net income

Adjusted net income
Average stockholders’ equity

$ 

$ 

$ 

$ 

$ 

$ 

Other

Corporate

Total

Insurance
69,857 
(18,438) 
(3,732) 
15,329 
2,006 
2,158 
— 
(398) 
66,782 

66,782 
300,820 

$ 

$ 

$ 

Mortgage
28,407 
(4,882) 
(5,798) 
— 
331 
— 
— 
(624) 
17,434 

17,434 
60,433 

$ 

$ 

$ 

17,210 
(1,992) 
(3,091) 
— 
213 
938 
(3,170) 
655 
10,763 

10,763 
113,717 

$ 

$ 

$ 

 22.2 %

 28.8 %

 9.5 %

(50,132)  $ 
4,021 
— 
— 
8,581 
2,171 
— 
4,249 
(31,110)  $ 

65,342 
(21,291) 
(12,621) 
15,329 
11,131 
5,267 
(3,170) 
3,882 
63,869 

(31,110)  $ 
(88,111) 
NM%

63,869 
386,859 

 16.5 %

For the Year Ended December 31, 2020

Tiptree Capital

$ 

$ 

$ 

Mortgage
31,102 
(7,066) 
4,018 
— 
2,482 
— 
— 
(1,958) 
28,578 

28,578 
47,202 

$ 

$ 

$ 

Other
(61,242) 
13,624 
67,668 
— 
174 
624 
(2,141) 
(14,210) 
4,497 

4,497 
138,606 

$ 

$ 

$ 

Corporate
(35,660) 
10,794 
— 
— 
3,172 
758 
— 
(4,131) 
(25,067) 

(25,067) 
(79,092) 

Insurance
26,948 
(3,725) 
13,804 
9,213 
2,287 
3,418 
— 
(8,522) 
43,423 

43,423 
285,760 

$ 

$ 

$ 

Total
(38,852) 
13,627 
85,490 
9,213 
8,115 
4,800 
(2,141) 
(28,821) 
51,431 

51,431 
392,476 

Adjusted return on average equity

 15.2 %

 60.5 %

 3.2 %

NM%

 13.1 %

68

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
For the Year Ended December 31, 2019

Tiptree Capital

Other

Corporate

Total

($ in thousands)
Income (loss) before taxes
Less: Income tax (benefit) expense
Less: Net realized and unrealized gains (losses)
Plus: Intangibles amortization (1)
Plus: Stock-based compensation expense
Plus: Non-recurring expenses
Plus: Non-cash fair value adjustments
Less: Tax on adjustments
Adjusted net income

Adjusted net income
Average stockholders’ equity

$ 

$ 

$ 

Insurance
37,030 
(8,455) 
(6,896) 
7,510 
2,891 
1,975 
— 
(1,249) 
32,806 

32,806 
266,397 

$ 

$ 

$ 

Mortgage
2,959 
(640) 
2,056 
— 
170 
— 
— 
(616) 
3,929 

3,929 
32,785 

$ 

$ 

$ 

23,391 
(4,457) 
(6,148) 
— 
— 
202 
(153) 
1,248 
14,083 

14,083 
161,133 

$ 

$ 

$ 

Adjusted return on average equity

 12.3 %

 12.0 %

 8.7 %

(34,241)  $ 
4,535 
— 
— 
3,299 
2,079 
— 
1,108 
(23,220)  $ 

29,139 
(9,017) 
(10,988) 
7,510 
6,360 
4,256 
(153) 
491 
27,598 

(23,220)  $ 
(54,978) 
NM%

27,598 
405,337 

 6.8 %

The footnotes below correspond to the tables above, under “—Adjusted Net Income - Non-GAAP and “—Adjusted Return on Average Equity - Non-GAAP”.
(1) Specifically associated with acquisition purchase accounting. See Note (3) Acquisitions.

Adjusted EBITDA - Non-GAAP

The Company defines Adjusted EBITDA as GAAP net income of the Company plus corporate interest expense, plus income 
taxes,  plus  depreciation  and  amortization  expense,  less  the  effects  of  purchase  accounting,  plus  non-cash  fair  value 
adjustments,  plus  significant  non-recurring  expenses,  and  plus  unrealized  gains  (losses)  on  available  for  sale  securities 
reported in other comprehensive income. Adjusted EBITDA is used to determine incentive compensation for the Company’s 
executive officers. Adjusted EBITDA is not a measurement of financial performance or liquidity under GAAP and should not 
be considered as an alternative or substitute for GAAP net income.

($ in thousands)

Net income (loss) attributable to common stockholders

Add: net (loss) income attributable to non-controlling interests 
Corporate debt related interest expense(1)
Consolidated provision (benefit) for income taxes
Depreciation and amortization
Non-cash fair value adjustments(2)
Non-recurring expenses(3)
Unrealized gains (losses) on AFS securities

Adjusted EBITDA

For the Year Ended December 31,

2021

2020

2019

$ 

$ 

38,132  $ 
5,919 
24,426 
21,291 
24,437 
(7,945) 
5,267 
(10,751) 
100,776  $ 

(29,158)  $ 
3,933 
23,322 
(13,627) 
17,268 
(7,122) 
4,800 
5,125 
4,541  $ 

18,361 
1,761 
19,754 
9,017 
13,083 
(3,156) 
4,257 
5,008 
68,085 

(1)

(2)

(3)

Corporate debt interest expense includes interest expense from secured corporate credit agreements, junior subordinated notes and preferred trust securities. Interest 
expense associated with asset-specific debt is not added-back for Adjusted EBITDA.
For maritime transportation operations, depreciation and amortization is deducted as a reduction in the value of the vessel.

Acquisition, start-up and disposition costs, including debt extinguishment, legal, taxes, banker fees and other costs. 

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.

 ($ 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

As of December 31, 
2020

2019

2021

400,181  $ 
17,227 
382,954  $ 

373,538  $ 
17,394 
356,144  $ 

34,124 

32,682 

411,415 
13,353 
398,062 

34,563 

11.22  $ 

10.90  $ 

11.52 

$ 

$ 

$ 

69

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
LIQUIDITY AND CAPITAL RESOURCES

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 interest payments on the 
Fortress credit facility, compensation, professional fees, office rent and insurance costs. In February 2020, we refinanced our 
existing facility with Fortress, extending the maturity to February 2025 and increasing the principal amount to $125 million, 
generating approximately $53 million of cash after repaying the existing facility and expenses. A portion of those funds were 
invested in Fortegra to fund growth, with the remainder used to provide additional liquidity. As a condition to the closing of 
the WP Transaction, we will assign the Fortress credit facility to Fortegra who will use proceeds from the WP Transaction to 
payoff  all  of  the  unpaid  principal  balance  of  the  Fortress  credit  facility.  In  addition,  on  or  prior  to  the  closing  of  the  WP 
Transaction, Fortegra will have certain of its subsidiaries repay $30.0 million principal balance of aggregate intercompany 
promissory notes to Tiptree Holdings LLC, plus accrued interest.

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 
Pincus  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,  2021,  cash  and  cash  equivalents,  excluding  restricted  cash,  were  $175.7  million,  compared  to  $136.9 
million  at  December  31,  2020,  an  increase  of  $38.8  million  primarily  as  a  result  of  additional  gross  written  premium  and 
premium equivalents at Fortegra.

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 and Adjusted EBITDA, 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, 

Interest Expense for the 
year ended December 31, 

2021

2020

2019

2021

2020

2019

$ 

$ 

162,160  $ 
114,063 
276,223  $ 

160,000  $ 
120,313 
280,313  $ 

185,000 
68,210 
253,210 

$ 

$ 

14,232  $ 
10,193 
24,425  $ 

13,305  $ 
10,017 
23,322  $ 

13,390 
6,292 
19,682 

As of December 31, 2021, the credit facility with Fortress carries a rate of LIBOR (with a minimum LIBOR rate of 1.0%), 
plus a margin of 6.75% per annum. The agreement requires quarterly principal payments of approximately $1.56 million. See 
Note (11) Debt, net in the notes to consolidated financial statements for details.

On  August  4,  2020,  Fortegra  entered  into  an  Amended  and  Restated  Credit  Agreement  by  and  among  Fortegra  and  its 
wholly-owned  subsidiary,  LOTS  Intermediate  Co.,  as  borrowers,  the  lenders  from  time  to  time  party  thereto,  certain  of 

70

 
 
 
 
 
 
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 $17.5 million for swing loans, and 
matures on August 4, 2023.

Consolidated Comparison of Cash Flows

($ in thousands)
Total cash provided by (used in):
Net cash (used in) provided by:

Operating activities
Investing activities
Financing activities

Net increase (decrease) in cash, cash equivalents and restricted cash

Operating Activities

For the Year Ended December 31,
2020

2019

2021

$ 

$ 

204,316  $ 
(273,759) 
73,735 

140,169  $ 
(123,491) 
31,749 

4,292  $ 

48,427  $ 

23,742 
(8,327) 
36,928 

52,343 

Cash  provided  by  operating  activities  was  $204.3  million  for  the  year  ended  December  31,  2021.  In  2021,  the  primary 
sources of cash from operating activities included consolidated net income (excluding unrealized gains and losses), proceeds 
from mortgage loans outpacing originations and growth in insurance company unearned premiums and net deferred revenues, 
partially offset by increases in deferred acquisition costs and reinsurance receivables.

Cash  provided  by  operating  activities  was  $140.2  million  for  the  year  ended  December  31,  2020.  In  2020,  the  primary 
sources of cash from operating activities included proceeds from mortgage loans outpacing originations, offset by increases 
in notes and accounts receivable and decreases in unearned premiums from our insurance operations.

Cash provided by operating activities was $23.7 million for the year ended December 31, 2019. In 2019, the primary sources 
of  cash  from  operating  activities  included  consolidated  net  income  (excluding  unrealized  gains  and  losses),  increases  in 
unearned  premiums,  reinsurance  payables,  and  deferred  revenues,  offset  by  increases  in  notes  and  accounts  receivable  and 
reinsurance receivables related to growth in our insurance operations.

Investing Activities 

Cash used in investing activities was $273.8 million for the year ended December 31, 2021. In 2021, the primary use of cash 
from investing activities was the purchase of investments outpacing proceeds from the sales of investments in our insurance 
investment portfolio, and the issuance of notes receivable outpacing proceeds.

Cash used in investing activities was $123.5 million for the year ended year ended December 31, 2020. In 2020, the primary 
use of cash from investing activities was the purchase of investments outpacing proceeds from the sales of investments in our 
insurance  investment  portfolio  and  the  issuance  of  notes  receivables  outpacing  proceeds.  This  was  partially  offset  by 
proceeds received in connection with the acquisition of Smart AutoCare.

Cash used in investing activities was $8.3 million for the year ended December 31, 2019. In 2019, the primary use of cash 
from investing activities was the issuance of notes receivables outpacing proceeds. This was offset by proceeds associated 
with a contingent earn-out from our sale of Care, proceeds from the sale of our Telos business, and sales and maturities of 
investments in excess of purchases in our insurance investment portfolio.

Financing Activities

Cash  provided  by  financing  activities  was  $73.7  million  for  the  year  ended  December  31,  2021.  In  2021,  proceeds  from 
borrowings  exceeded  principal  repayments  on  mortgage  warehouse  facilities  and  asset-based  debt  supporting  our  premium 
finance operations in the insurance business, partially offset by net redemptions of non-controlling interest of $3.5 million, 
the  repurchase  of  the  Company’s  common  stock  and  other  changes  in  additional  paid-in  capital  of  $8.1  million  and  the 
payment of $5.3 million in dividends.

Cash provided by financing activities was $31.7 million for the year ended December 31, 2020. In 2020, our new borrowings 
exceeded our principal paydowns, primarily from increased borrowings on our secured term credit agreement and our secured 
corporate revolving credit agreement in our insurance operations, partially offset by decreased borrowings on our mortgage 

71

 
 
 
 
 
 
warehouse  facilities.  Net  cash  provided  by  increased  borrowings  was  offset  by  the  repurchase  of  $13.9  million  of  the 
Company’s common stock and the payment of $5.6 million in dividends.

Cash provided by financing activities was $36.9 million for the year ended December 31, 2019. In 2019, our new borrowings 
exceeded  our  principal  repayments  primarily  from  increased  borrowings  on  our  mortgage  warehouse  facilities  due  to 
increased volume in our mortgage business, increased borrowing on our secured corporate credit agreement in our insurance 
business to support growth, and a vessel backed term loan, offset by the repayment of asset based borrowings in our credit 
loan fund, held within our insurance investment portfolio. Net cash provided by increased borrowings was partially offset by 
the repurchase of $9.1 million of the Company’s common stock and the payment of $5.5 million in dividends. 

CRITICAL ACCOUNTING POLICIES AND ESTIMATES

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,  2021  and  2020,  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  are  established  in  accordance  with  GAAP  using  generally  accepted  actuarial 
methods.  Credit  life  and  accidental  death  and  destruction  (AD&D)  unpaid  claims  reserves  include  claims  in  the  course  of 
settlement  and  incurred  but  not  reported  (IBNR)  claims.  Credit  disability  unpaid  claims  reserves  also  include  continuing 
claim reserves for open disability claims. For all other Fortegra product lines, unpaid claims reserves are bulk reserves and 
are entirely IBNR. 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, target loss ratios, in-force amounts, unearned 
premium reserves, industry recognized morbidity tables or a combination of these factors. 

In arriving at the unpaid claims reserves, the Company conducts an actuarial analysis on a basis gross of reinsurance. The 
same estimates used as a basis in calculating the gross unpaid claims reserves are then used as the basis for calculating the net 
unpaid claims 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 years ended December 31, 2021, 2020, and 2019, the Company experienced an increase in prior year development 
of $2.6 million, $5.4 million, and $5.2 million, respectively. In 2021, the $2.6 million increase in prior year development is 

72

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.  In  2020,  the  $5.4  million  increase  was  due  to  higher  than  expected  claim  frequency  from 
business  written  by  a  small  group  of  producers  of  our  personal  and  commercial  lines  of  business,  of  which  $2.2  million 
related to our non-standard auto business. The underlying cause of the 2020 prior year development was the result of a subset 
of  risk  where  the  loss  ratio  pegs  used  in  our  year  end  actuarial  determination  was  low  given  the  ultimate  frequency  that 
emerged.  In  2019,  the  entire  $5.2  million  increase  related  to  our  non-standard  auto  business.  The  underlying  cause  of  this 
development  was  higher  than  expected  claim  frequency.  The  non-standard  programs  which  contributed  to  the  prior  year 
development in both 2020 and 2019, one active program which was new in 2018 and two programs in run-off, experienced 
loss  emergence  in  excess  of  levels  contemplated  when  originally  pricing  the  products.  The  Company  responded  to  this 
emergence by filing for increased rates for the one underperforming active program and non-renewing all business for the 
two programs in run-off.

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. 
Earned premiums, net in 2021 were $685.6 million and net losses and loss adjustment expenses were $253.5 million, which 
resulted to a loss ratio of 37.0%. Without the $2.6 million prior year development, the calendar year loss ratio would have 
been  approximately  0.4%  lower.  For  comparison,  the  2020  and  2019  loss  ratios  were  37.2%  and  30.3%,  respectively.  In 
general, the Company's loss ratio results have been predictable and consistent over time. In 2021, the $2.6 million prior year 
development represented only 3.7% of pretax income of our insurance business of $69.9 million, and 3.1% of the opening net 
liability  for  losses  and  loss  adjustment  expense  of  $83.9  million  in  the  same  year.  Actuarial  estimates  are  subject  to 
estimation variability, and while management uses its best judgment in establishing the estimate of required unpaid claims, 
different  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 2021 would be as follows:

73

Accident Year 2021 Sensitivity Test
Change in Loss & Frequency & Severity on Ultimate 
($ in thousands)
Scenario
5% higher
3% higher
1% higher
Base scenario
1% lower
3% lower
5% lower

Ultimate Cost

Change

$ 

$ 

$ 

$ 

$ 

$ 

$ 

263  $ 

258  $ 

253  $ 

250  $ 

248  $ 

243  $ 

238  $ 

12,515 

7,509 

2,503 

— 

(2,503) 

(7,509) 

(12,515) 

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.

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, 
2021, 2020 and 2019.

Amortization  of  deferred  acquisition  costs  was  $375.1  million,  $265.8  million  and  $287.8  million  for  the  years  ended 
December 31, 2021, 2020 and 2019, respectively.

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,  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 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  $258.6  million,  $163.6  million  and  $89.0  million  for  the  years  ended  December  31,  2021,  2020  and 
2019,  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 

74

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, motor 
club,  and  auto  and  consumer  goods  service  contracts.  Related  administrative  fee  revenue  is  recognized  consistent  with  the 
earnings  recognition  pattern  of  the  underlying  insurance  policies,  debt  cancellation  contracts,  vehicle  service  contracts  and 
motor club memberships being administered, using Rule of 78's, modified Rule of 78's, pro rata, or other actuarial 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.

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 
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.

75

 
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 
LIBOR rates and the spread over LIBOR 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, 2021, the Company had 
$125 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.  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,  2021,  we  had  $114.1  million  of  general  purpose  floating  rate  debt  with  a  weighted  average  rate 
of 7.75%. A 100 basis point change in interest rates would increase interest expense by $0.2 million and decrease interest 
expense  by  an  insignificant  amount  (including  the  effect  of  applicable  minimum  interest  rates)  on  an  annualized  basis.  As 
of December 31, 2020, we had $120.3 million of general purpose floating rate debt with a weighted average rate of 7.2%.

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, 2021, we had $658.8 million invested in interest bearing instruments, which represents 72% 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 $20.0 million. As of December 31, 2020, we had $510.0 million invested in interest bearing 
instruments,  which  represented  63%  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 $14.2 million.

76

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
Trade Claims
Other

Total

As of December 31,

2021

2020

$ 

$ 

58,660  $ 
144,877 
17,447 
2,696 
2,590 

44,350 
94,941 
36,192 
1,355 
3,992 

7,099 

7,795 

38,965 
21,057 
19,737 
216 
313,344  $ 

105,777 
17,703 
— 
802 
312,907 

(1) 

(2) 

(3) 

The Company also holds investments in U.S. Treasury securities and obligations of U.S. government authorities and agencies of $351.2 million and 
$196.3 million as of December 31, 2021 and 2020, respectively. These investments do not represent a credit risk and are excluded.
The  Company  also  holds  investments  in  mortgage  loans  held  for  sale  of  $98.5  million  and  $82.9  million  as  of  December  31,  2021  and  2020, 
respectively. These investments do not represent a credit risk and are excluded.
The Company also holds other investments of $88.7 million and $95.4 million as of December 31, 2021 and 2020, respectively, primarily comprised of 
vessels. 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, 2021 and 2020, 72% 
and 62%, 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 $6.3 million and $5.9 million to the fair value 
of the portfolio as of December 31, 2021 and 2020, 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, 2021
Tiptree 
Capital - 
Other

Insurance

Total

As of December 31, 2020
Tiptree 
Capital - 
Other

Insurance

Invesque
Fixed income exchange traded fund  
Other equity securities

$ 

Total equity securities

$ 

6,015  $ 

53,154 
50,515 
109,684  $ 

28,799  $ 
— 
— 
28,799  $ 

34,814  $ 
53,154 
50,515 
138,483  $ 

5,370  $ 

63,875 
28,885 
98,130  $ 

25,708  $ 
— 
— 
25,708  $ 

Total

31,078 
63,875 
28,885 
123,838 

A  10%  increase  or  decrease  in  the  fair  value  of  such  investments  would  result  in  $13.8  million  and  $12.3  million  of 
unrealized gains and losses as of December 31, 2021 and 2020, respectively. 

As of December 31, 2021 and 2020, we owned 17.0 million shares of common stock, respectively, or approximately 31%, 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 the fair market value of 

77

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
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, 2021 and 2020, 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”.

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, 2021 and 2020, the total fair value of derivative assets subject to counterparty risk, including the effect of any 
legal  right  of  offset,  totaled  $8.2  million  and  $11.5  million,  respectively.  We  generally  manage  our  counterparty  risk  to 
derivative counterparties by entering into contracts with counterparties of high credit quality.

Total reinsurance receivables were $880.8 million and $728.0 million as of December 31, 2021 and 2020, respectively. Of 
those  amounts,  $533.6  million  and  $442.2  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, 2021, the non-affiliated 
reinsurers from whom our insurance business has the largest reinsurance receivable balances represented $126.1 million, or 
14.3%  of  the  total,  and  included:  Allianz  Global  Corporate  &  Specialty  SE  (A.M.  Best  Rating:  A+  rated),  Canada  Life 
International Reinsurance (Bermuda) Corporation (A.M. Best Rating: A+ rated), and Canada Life Assurance Company (A.M. 
Best Rating: A+ rated). The related receivables of these reinsurers are collateralized by assets on hand, assets held in trust 
accounts  and  letters  of  credit.  As  of  December  31,  2021,  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.

We were also exposed to counterparty risk of approximately $157.9 million and $131.8 million as of December 31, 2021 and 
2020,  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 $89.8 million and $62.1 million as of December 31, 2021 and 2020, 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.

78

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, 2021 and 2020
Consolidated Statements of Operations for the years ended December 31, 2021, 2020 and 2019
Consolidated Statements of Comprehensive Income (Loss) for the years ended December 31, 2021, 2020 and 2019
Consolidated Statements of Changes in Stockholders’ Equity for the years ended December 31, 2021, 2020 and 2019
Consolidated Statements of Cash Flows for the years ended December 31, 2021, 2020 and 2019
Notes to Consolidated Financial Statements

Page
F- 2
F- 1
F- 2
F- 3
F- 4
F- 5
F- 6

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, 2021 and 2020, 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,  2021,  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, 2021 and 2020, and the results of its operations and its cash flows for each of the three years in the period 
ended December 31, 2021, 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,  2021,  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 March 11, 2022, 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  reserves  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

Our audit procedures related to 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 reserves 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.

◦ With assistance from our actuarial specialists, we performed retrospective procedures comparing actual 
loss  development  with  expected  loss  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
March 11, 2022

We have served as the Company's auditor since 2017.

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,  2021,  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, 2021, 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, 2021, of the Company 
and our report dated March 11, 2022 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. 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
March 11, 2022

TIPTREE INC. AND SUBSIDIARIES
Consolidated Balance Sheets
(in thousands, except share data)

As of December 31,
2020
2021

$ 

$ 

577,448  $ 
105,583 
138,483 
168,656 
990,170 
175,718 
19,368 
454,369 
880,836 
379,373 
179,103 
122,758 
146,844 
250,608 
3,599,147  $ 

$ 

393,349  $ 

1,123,952 
331,703 
534,863 
265,569 
306,536 
242,994 
3,198,966  $ 

377,133 
90,732 
123,838 
219,701 
811,404 
136,920 
58,355 
370,452 
728,009 
229,430 
179,236 
138,215 
162,034 
181,705 
2,995,760 

366,246 
860,690 
233,438 
399,211 
224,660 
362,865 
175,112 
2,622,222 

—  $ 

— 

34 
317,459 
(2,685) 
68,146 
382,954 
17,227 
400,181 
3,599,147  $ 

33 
315,014 
5,674 
35,423 
356,144 
17,394 
373,538 
2,995,760 

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 receivables
Deferred acquisition costs
Goodwill
Intangible assets, net
Other assets
Assets held for sale

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
Liabilities held for sale
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, 34,124,153 and 32,682,462 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
Total stockholders’ equity

Total liabilities and stockholders’ equity

See accompanying notes to consolidated financial statements. 

F-1

$ 

$ 

$ 

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Consolidated Statements of Operations
(in thousands, except share data)

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

For the Year Ended December 31, 

2021

2020

2019

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  $ 

477,991  $ 
186,973 
21,101 
9,916 
62,410 
51,910 
810,301 

236,898 
280,210 
172,737 
32,582 
17,578 
109,148 
849,153 
(38,852) 
(13,627) 
(25,225) 
3,933 
(29,158)  $ 

499,108 
106,239 
9,608 
14,017 
83,868 
59,888 
772,728 

170,681 
303,057 
129,479 
27,059 
13,569 
99,744 
743,589 
29,139 
9,017 
20,122 
1,761 
18,361 

1.13  $ 
1.09  $ 

(0.86)  $ 
(0.86)  $ 

0.52 
0.50 

$ 

$ 

$ 
$ 

33,223,792 
33,688,256 

33,859,775 
33,859,775 

34,578,292 
34,578,292 

Dividends declared per common share

$ 

0.16  $ 

0.16  $ 

0.16 

See accompanying notes to consolidated financial statements. 

F-2

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Consolidated Statements of Comprehensive Income (Loss)
(in thousands)

For the Year Ended December 31, 
2020

2019

2021

Net income (loss)

$ 

44,051  $ 

(25,225)  $ 

20,122 

Other comprehensive income (loss), net of tax:
Unrealized gains (losses) on available for sale securities:

Unrealized holding gains (losses) arising during the period
Related (provision) benefit for income taxes
Reclassification of (gains) losses included in net income (loss)
Related (provision) benefit for income taxes
Unrealized gains (losses) on available for sale securities, net of tax

Other comprehensive income (loss), net of tax
Comprehensive income (loss)

(10,112) 
2,223 
(638) 
139 
(8,388) 

(8,388) 
35,663 

5,653 
(1,289) 
(528) 
113 
3,949 

3,949 
(21,276) 

Less: comprehensive income (loss) attributable to non-controlling interests
Comprehensive income (loss) attributable to common stockholders

$ 
$ 

5,890 
29,773  $ 

3,948 
(25,224)  $ 

6,320 
(1,409) 
(1,312) 
280 
3,879 

3,879 
24,001 

1,785 
22,216 

See accompanying notes to consolidated financial statements.

F-3

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Consolidated Statements of Changes in Stockholders’ Equity
(in thousands, except shares)

Common stock

Number of 
shares

Par 
value 

Additional 
paid-in 
capital

Accumulated 
other 
comprehensive 
income (loss)

Retained 
earnings

Total
Tiptree Inc. 
stockholders’ 
equity

Non-
controlling 
interests

Total 
stockholders' 
equity

 35,870,348  $  36  $  331,892  $ 

— 

  — 

— 

(2,058)  $ 
(99) 

— 
164,935 
 (1,472,730) 
— 
— 

  — 
  — 
(1) 
  — 
  — 

— 
— 
— 
— 

  — 
  — 
  — 
  — 

3,145 
187 
(9,084) 
— 
— 

— 
— 
— 
— 

 34,562,553  $  35  $  326,140  $ 

— 

  — 

— 

57,231  $  387,101  $ 

99 

— 
— 
— 
— 
— 

— 

3,145 
187 
(9,085) 
— 
— 

12,158  $  399,259 
— 

— 

2,917 
(2,483) 
— 
61 
(3,585) 

6,062 
(2,296) 
(9,085) 
61 
(3,585) 

— 
— 
— 
— 
— 

— 
— 
3,855 
— 
1,698  $ 
42 

— 
(5,502) 
— 
18,361 
70,189  $  398,062  $ 

— 
(5,502) 
3,855 
18,361 

(42) 

— 

2,500 
2,500 
(5,502) 
— 
3,879 
24 
1,761 
20,122 
13,353  $  411,415 
— 

— 

— 
504,195 
 (2,384,286) 

  — 
  — 
(2) 

3,441 
100 
(13,887) 

— 
— 
— 

— 
— 
— 

— 
— 
— 
— 
— 

  — 
  — 
  — 
  — 
  — 

(645) 
(135) 
— 
— 
— 

 32,682,462  $  33  $  315,014  $ 

— 
— 
— 
3,934 
— 
5,674  $ 

— 
— 
(5,566) 
— 
(29,158) 
35,423  $  356,144  $ 

3,441 
100 
(13,889) 
— 
(645) 
(135) 
(5,566) 
3,934 
(29,158) 

4,130 
(2,223) 
— 

7,571 
(2,123) 
(13,889) 
— 
(2,034) 
(560) 
(5,566) 
3,949 
(25,225) 
17,394  $  373,538 

(1,389) 
(425) 
— 
15 
3,933 

— 
596,601 

  — 
  — 

  1,166,307 
(528,662) 
207,445 
— 
— 
— 

2 
(1) 
  — 
  — 
  — 
  — 

— 
— 
— 
— 

  — 
  — 
  — 
  — 

2,331 
3,563 

105 
(2,881) 
— 
(770) 
— 
— 

97 
— 
— 
— 

 34,124,153  $  34  $  317,459  $ 

— 
— 

— 
— 
— 
— 
— 
— 

— 
— 

— 
— 
— 
— 
— 
— 

2,331 
3,563 

107 
(2,882) 
— 
(770) 
— 
— 

1,725 
(4,816) 

(1,565) 
— 
— 
(309) 
100 
(1,095) 

4,056 
(1,253) 

(1,458) 
(2,882) 
— 
(1,079) 
100 
(1,095) 

— 
— 
(8,359) 
— 
(2,685)  $ 

— 
(5,409) 
— 
38,132 
68,146  $  382,954  $ 

97 
(5,409) 
(8,359) 
38,132 

— 
(97) 
(5,409) 
— 
(8,388) 
(29) 
5,919 
44,051 
17,227  $  400,181 

Balance at December 31, 2018
Adoption of accounting standard (1)
Amortization of share-based incentive 
compensation
Vesting of share-based incentive compensation(2)
Shares purchased under stock purchase plan
Non-controlling interest contributions
Non-controlling interest distributions
Net change in non-controlling
interest
Dividends declared
Other comprehensive income (loss), net of tax
Net income (loss)
Balance at December 31, 2019
Adoption of accounting standard (3)
Amortization of share-based incentive 
compensation
Vesting of share-based incentive compensation(2)
Shares purchased under stock purchase plan
Non-controlling interest contributions
Non-controlling interest distributions
Net change in non-controlling interest
Dividends declared
Other comprehensive income (loss), net of tax
Net income (loss)
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 (4)
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
interest
Dividends declared
Other comprehensive income (loss), net of tax
Net income (loss)
Balance at December 31, 2021

(1)      Amounts reclassified due to adoption of ASU 2018-02. See Note (2) Summary of Significant Accounting Policies.
(2)      Includes subsidiary RSU exchanges. See Note (19) Stock Based Compensation.
(3)    Amounts reclassified due to adoption of ASU 2016-13. See Note (2) Summary of Significant Accounting Policies.
(4)    Exchange included $1,458 in cash.

See accompanying notes to consolidated financial statements.

F-4

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Consolidated Statements of Cash Flows
(in thousands)

For the Year Ended December 31, 
2020

2021

2019

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 sale of businesses
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
Other

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 receivables
(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
Proceeds from the sale of real estate and other assets
Purchases of property, plant and equipment
Proceeds from the sale of businesses
Proceeds from notes receivable
Issuance of notes receivable
Business and asset acquisitions, net of cash, restricted cash and deposits (1)
Net cash provided by (used in) investing activities

Financing Activities:

Dividends paid
Net non-controlling interest (redemptions) contributions
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

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 assets held for sale

Cash, cash equivalents and restricted cash – end of period

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
Equity securities acquired as part of a dividend reinvestment plan
Acquired real estate properties through, or in lieu of, foreclosure of the related loan
Shares issued in exchange for vested subsidiary awards
Acquisition of non-controlling interest

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

$ 

38,132  $ 
5,919 
44,051 

(29,158)  $ 
3,933 
(25,225) 

(151,350) 
1,928 
11,130 
2,947 
24,437 
8,924 
17,730 
1,607 
291 

(3,884,533) 
3,925,984 
(54,378) 
(152,827) 
(149,943) 
(7,065) 
263,262 
98,265 
135,652 
40,909 
27,295 
204,316 

(1,430,879) 
1,172,044 
8,604 
(2,764) 
125 
56,055 
(77,077) 
133 
(273,759) 

(62,410) 
4,428 
8,117 
2,229 
17,578 
7,374 
10,733 
1,015 
(333) 

(3,064,003) 
3,152,104 
(48,527) 
(116,839) 
(62,937) 
(22,417) 
105,697 
33,968 
122,042 
53,716 
23,859 
140,169 

(1,494,688) 
1,400,229 
2,981 
(6,694) 
500 
41,582 
(62,088) 
(5,313) 
(123,491) 

18,361 
1,761 
20,122 

(83,868) 
(7,598) 
6,363 
1,161 
13,569 
7,568 
6,815 
714 
1,381 

(2,048,228) 
2,043,097 
(33,085) 
(119,482) 
3,570 
269 
155,549 
12,773 
16,397 
26,272 
383 
23,742 

(389,206) 
394,331 
11,857 
(8,519) 
18,329 
36,690 
(67,176) 
(4,633) 
(8,327) 

(5,409) 
(3,532) 
(114) 
4,084,299 
(3,993,364) 
(8,145) 
73,735 
4,292 
195,275 
4,879 
204,446 
9,360 
195,086  $ 

(5,566) 
(2,134) 
(4,571) 
3,379,688 
(3,321,779) 
(13,889) 
31,749 
48,427 
144,590 
7,137 
200,154 
4,879 
195,275  $ 

(5,502) 
(3,524) 
(586) 
2,237,329 
(2,181,704) 
(9,085) 
36,928 
52,343 
96,524 
2,860 
151,727 
7,137 
144,590 

36,885  $ 
2,079  $ 

29,538  $ 
1,066  $ 

26,224 
3,301 

4,281  $ 
—  $ 
—  $ 
107  $ 
—  $ 

9,989  $ 
953  $ 
—  $ 
—  $ 
—  $ 

2021

As of December 31,
2020

175,718  $ 
19,368 

195,086  $ 

136,920  $ 
58,355 

195,275  $ 

33,558 
— 
2,596 
— 
2,500 

2019

133,117 
11,473 
144,590 

$ 

$ 
$ 

$ 
$ 
$ 
$ 
$ 

$ 

$ 

(1) 

Changes in balance sheet balances due to acquisitions have been netted down in the respective line items. See Note (3) Acquisitions for additional information.

See accompanying notes to consolidated financial statements.

F-5

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(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.

(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;
Vessel valuations, residual value of vessels and the useful lives of vessels; 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.

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 

F-6

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

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, Assets and Liabilities Held for Sale and Discontinued Operations

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, assets and liabilities held for sale and discontinued operations are described 
in more detail in (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 
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 

F-7

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

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

From  time  to  time,  derivative  instruments  are  used  in  the  overall  strategy  to  manage  exposure  to  market  risks  primarily 
related to fluctuations in interest rates. 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. 

Derivative Instruments Designated as Cash Flow Hedging Instruments

The Company uses cash flow hedges from time to time to reduce the exposure to variability of cash flows from floating rate 
borrowings. If a derivative instrument meets certain cash flow hedge accounting criteria, it is recorded on the consolidated 
balance sheet at its fair value, as either an asset or a liability, with offsetting changes in fair value recognized in AOCI. The 
effective portion of the changes in fair value of derivatives are reported in AOCI and amounts previously recorded in AOCI 
are  recognized  in  earnings  in  the  period  in  which  the  hedged  transaction  affects  earnings.  Any  ineffective  portions  of  the 
change in fair value of the derivative are recognized in current earnings.

Stock Based Compensation

The Company accounts for share‑based compensation issued to employees, directors, and affiliates of the Company using the 
current fair value based methodology.

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  subsidiary  restricted  stock  units  (RSUs)  exchangeable  into  common  stock  of  the  Company  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-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.

F-8

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

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. Two of our subsidiaries file federal and state tax returns 
on  a  stand-alone  basis,  one  of  which  is  held  for  sale.  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  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, 2020 and 2019. 

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. 

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 

F-9

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

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

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.

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. 

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. 

F-10

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

The Company’s estimate of future revenue is based upon time charter equivalent (TCE) rates using current market rates. The 
Company uses average historical rates for periods beyond those for which rates are available. Estimated cash flows are net of 
brokerage and address commissions, vessel operating expenses, and estimated costs of drydocking and include an inflation 
factor, as appropriate. The projected undiscounted future cash flows are comprised of the net of these inflows and outflows, 
plus an estimated salvage value.

As  of  December  31,  2021,  the  appraised  values  and  undiscounted  future  cash  flows  were  both  higher  than  the  carrying 
amount of each of the vessels in the Company’s fleet and, as such, no loss on impairment was recognized.

Cash and Cash Equivalents

The  Company  considers  all  highly  liquid  investments  of  sufficient  credit  quality  purchased  with  an  initial  maturity  of 
three months or less to be cash equivalents. Cash and cash equivalents consist of U.S. denominated cash on hand, cash held in 
banks and investments in money market funds. 

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

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 Receivables

F-11

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

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  $375,052,  $265,781  and  $287,834  for  the 
years ended December 31, 2021, 2020 and 2019, 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, 
2021, 2020 and 2019.

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.

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

F-12

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

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 the Rule of 78's, pro rata, or other actuarial methods 
as  appropriate  for  the  type  of  business.  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, 2021 and 2020, 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 
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, 2021 
and 2020, our appointed independent third-party actuaries found the Company’s reserves to be adequate.

F-13

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

Deferred Revenue

Deferred revenues represent the portion of income that will be earned in the future attributable to motor club memberships, 
mobile device protection plans, and other non-insurance service contracts that are earned over the respective contract periods 
using the Rule of 78's, modified Rule of 78's, pro rata, 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,  2021  and  2020,  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,  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  Fees.  Service  fee  revenue  is  recognized  as  the  services  are  performed.  These  services  include  fulfillment, 
software  development,  and  claims  handling  for  our  customers.  Collateral  tracking  fee  income  is  recognized  when  the 
service is performed and billed. 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  probable.  During  the  years  ended  December  31,  2021,  2020  and  2019,  respectively,  the  Company  did  not 
incur a loss with respect to a specific significant service fee contract.

Administrative Fees. 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, motor club, and service contract products. 
Related  administrative  fee  revenue  is  recognized  consistent  with  the  earnings  recognition  pattern  of  the  underlying 
insurance policies, debt cancellation contracts, auto and consumer goods service contracts, and motor club memberships 
being administered, using Rule of 78's, modified Rule of 78's, pro rata, or other actuarial 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.

Ceding Commissions

Ceding commissions earned under reinsurance agreements are based on contractual formulas that take into account, in part, 
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 

F-14

 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

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.

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  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.

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. 

Recent Accounting Standards

Recently Adopted Accounting Pronouncements

F-15

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

Standard
2019-12 Income Taxes 
(Topic 740): 
Simplifying the 
Accounting for Income 
Taxes

2016-13 Financial 
Instruments -Credit 
Losses (Topic 326): 
Measurement of Credit 
Losses on Financial 
Instruments

2018-13 Fair Value 
Measurement (Topic 
820): Disclosure 
Framework—Changes 
to the Disclosure 
Requirements for Fair 
Value Measurement

Description

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.
Topic 326 amended guidance on reporting credit losses for 
assets held on an amortized cost basis and AFS debt 
securities. For assets held on an amortized cost basis, 
Topic 326 eliminates the probable initial recognition 
threshold in previous GAAP and instead requires an entity 
to reflect its current estimate of all expected credit losses. 
The allowance for credit losses is a valuation account that 
is deducted from the amortized cost basis of the financial 
assets to present the net amount expected to be collected. 
For AFS debt securities, credit losses should be measured 
in a manner similar to previous GAAP; however, Topic 
326 will require that credit losses be presented as an 
allowance rather than as a write-down. Changes in the 
allowance account are recorded in the period of change as 
a credit loss expense or reversal of credit loss expense. 
The measurement of credit losses is not impacted, except 
that credit losses recognized are limited to the amount by 
which fair value is below amortized cost.

The amendments in this update require additions, 
modifications and elimination to the fair value 
measurement disclosure. The objective of these disclosure 
requirements is to provide users of financial statements 
with information about assets and liabilities measured at 
fair value: 
(a) The valuation techniques and inputs that a reporting 
entity uses to arrive at its measures of fair value, including 
judgments and assumptions that the entity makes,
(b) The uncertainty in the fair value measurements as of 
the reporting date, and 
(c) How changes in fair value measurements affect an 
entity’s performance and cash flows.

Adoption Date
January 1, 2021

Impact on Financial Statements

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 does
not currently impact the Company’s financial
statements.

January 1, 2020

The adoption of this guidance resulted in an 
immaterial reclassification from AOCI to 
retained earnings in the Company’s 
consolidated financial statements.

January 1, 2020

The retrospective adoption of this standard 
resulted in additional disclosures related to 
inputs of Level 3 investments. This adoption 
resulted in an immaterial impact to the 
Company’s consolidated financial statements. 
See Note (12) Fair Value of Financial 
Instruments.

2018-02 Income 
Statement—Reporting 
Comprehensive Income 
(Topic 220): 
Reclassification of 
Certain Tax Effects from 
Accumulated Other 
Comprehensive Income

The amendments in this update allow a reclassification 
from AOCI to retained earnings for stranded tax effects 
resulting from the Tax Cuts and Jobs Act of 2017. The 
amendments in this update affect any entity that is 
required to apply the provisions of Topic 220 and has 
items of other comprehensive income for which the related 
tax effects are presented in other comprehensive income as 
required by GAAP. 

January 1, 2019

The adoption of this guidance resulted in an 
immaterial reclassification from AOCI to 
retained earnings in the Company’s 
consolidated financial statements.

2016-02 Leases (Topic 
842)

This new standard introduced a new lessee model that 
brings substantially all leases onto the balance sheet. In 
addition, while the new guidance retains most of the 
principles of the previous existing lessor model in GAAP, 
it aligns many of those principles with ASC 606, Revenue 
From Contracts With Customers.

January 1, 2019

The adoption of this guidance (practical 
expedient) resulted in the Company recognizing 
a right of use asset of $32,052 as part of other 
assets and a lease liability of $33,558 as part of 
other liabilities and accrued expenses in the 
consolidated balance sheets, as well as de-
recognizing the liability for deferred rent that 
was required under the previous guidance for its 
operating lease agreements at January 1, 2019. 

F-16

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

Recently Issued Accounting Pronouncements, Not Yet Adopted

Standard

2020-04 Reference 
Rate Reform (Topic 
848): Facilitation of 
the Effects of 
Reference Rate 
Reform on Financial 
Reporting

Description

Adoption Date

The amendments in this update 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. 

The standard is effective for all 
entities as of March 12, 2020, 
through December 31, 2022. The 
Company is evaluating their 
option to adopt the guidance when 
it is applicable.

Impact on Financial Statements
The Company is currently evaluating 
the effect on its consolidated financial 
statements.

 (3) Acquisitions

Acquisition of Smart AutoCare

On January 3, 2020, a subsidiary of the Company acquired (the Acquisition) all of the equity interests of Accelerated Service 
Enterprise  LLC.,  SAC  Holdings  Inc.,  Dealer  Motor  Services,  Inc.,  Independent  Dealer  Group,  Inc.,  Ownershield,  Inc., 
Freedom Insurance Company, Ltd. (Freedom), SAC Admin, Inc., SAC Insurance Company, Inc., Smart AutoCare, Inc. and 
Smart  AutoCare  Administration  Solutions,  Inc.  (together  Smart  AutoCare),  pursuant  to  the  Equity  Interest  Purchase 
Agreement  (as  amended,  the  Purchase  Agreement)  between  Fortegra  Warranty  Holdings,  LLC.  (Buyer)  and  Peter  Masi 
(Seller), dated as of December 16, 2019. Concurrent with the Acquisition, Freedom terminated reinsurance agreements with 
affiliates of Seller (the Commutation Transaction). 

Tiptree  paid  Seller  $111,804,  net  of  working  capital  true-ups,  in  cash  at  closing,  $8,250  of  which  was  held  in  an  escrow 
account  to  satisfy  indemnity  claims  and  was  released  on  August  3,  2021.  Simultaneously,  pursuant  to  the  Commutation 
Transaction, affiliates of Seller paid Freedom $102,000 in cash. The Purchase Agreement also provides for an earn out of up 
to  $50,000  in  cash  based  on  Smart  AutoCare  achieving  specified  performance  metrics  measured  on  the  4-year  and  6-year 
anniversary  of  closing  (Reserve  Based  Earn-Out  Amount)  and  an  additional  earn  out  of  up  to  $30,000  payable  in  cash  or 
Tiptree common stock based on Smart AutoCare achieving other certain specified performance metrics measured on the 4-
year  anniversary  of  closing  (Profits  Based  Earn-Out  Amount).  In  addition,  the  purchase  price  will  be  subject  to  a  true-up 
following the 6-year anniversary of the closing (Underwriting Profitability True-Up) based on the adequacy of certain legacy 
reserves, offset by certain earnings on new business. Fortegra Warranty may hold back all or a portion of any Reserve Based 
Earn-Out Amounts until final determination of the legacy reserves used to calculate the Underwriting Profitability True-Up if 
in Tiptree’s reasonable opinion such amount may be needed to offset a deficiency in such legacy reserves. In addition, if the 
deficiency  in  the  legacy  reserves  used  to  calculate  the  Underwriting  Profitability  True-Up  is  greater  than  the  aggregate 
amount  owing  to  Seller  for  the  Reserve-Based  Earn-Out  Amount  and  Profits-Based  Earn-Out  Amount,  Seller  shall  pay 
Tiptree an amount equal to the lesser of such difference and $10,000.

Smart AutoCare’s results are included in the Company’s Insurance segment. The financial results of Smart AutoCare have 
been included in the Company’s results as of the acquisition date.

The fair value of assets acquired and liabilities assumed represent the allocation as our evaluation of facts and circumstances 
available  as  of  the  acquisition  date.  The  allocation  of  the  purchase  price  to  the  intangible  assets  is  based  on  fair  value 
estimates  and  have  been  reviewed  by  management.  The  allocation  of  the  purchase  price  has  been  finalized  and  all 
measurement period adjustments have been recorded.

Management’s allocation of the purchase price to the net assets acquired resulted in the recording of finite-lived intangible 
assets valued at $93,700, with an estimated amortization period of 5 to 13.5 years and will be tax deductible over a 15 year 
period.  The  residual  amount  of  the  purchase  price  after  the  allocation  to  net  assets  acquired  and  identifiable  intangibles  of 
$60,346 has been allocated to goodwill. This goodwill is included in the Insurance segment. It is expected that $21,127 of this 
goodwill will be tax deductible over a 15 year period.

F-17

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

The following table presents the determination of the acquisition date fair value amounts for the identifiable assets acquired, 
liabilities assumed, and goodwill recorded in connection with the Acquisition, in accordance with the acquisition method of 
accounting:

Assets:
Investments:

Available for sale securities, at fair value

Total investments
Cash and cash equivalents 
Restricted cash
Notes and accounts receivable, net
Reinsurance receivables
Intangible assets, net
Other assets

Total assets

Liabilities:

Policy liabilities and unpaid claims
Deferred revenue
Reinsurance payable
Other liabilities and accrued expenses

Total liabilities

Net assets acquired

Goodwill

Acquisition costs

As of
January 3,
2020

$ 

$ 

$ 

$ 

$ 

110 
110 
120,934 
764 
6,214 
71,337 
93,700 
34,053 
327,112 

55,151 
182,568 
27,075 
10,860 
275,654 
51,458 
60,346 
111,804 

3,539 

Supplemental pro forma results of operations have not been presented for the Acquisition as they are not material in relation 
to the Company’s reported results.

The following table shows the values recorded by the Company, as of the acquisition date, for finite-lived intangible assets 
and the range of their estimated amortization period:

Intangible Assets
Customer relationships
Software licensing
Trade names

Total acquired finite-lived intangible assets

Acquisition of Sky Auto

Weighted 
Average 
Amortization 
Period
(in Years)
7.2
5.0
13.5
7.7

Value as of 
acquisition 
date

$ 

$ 

86,000 
600 
7,100 
93,700 

On December 31, 2020, a subsidiary in our insurance business acquired all of the equity interests in Sky Auto for total net 
cash  consideration  of  approximately  $25,200.  Sky  Auto  markets  vehicle  service  contracts  to  consumers  within  the  United 
States.

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 $19,867 and $5,340. 
The  tax  basis  in  goodwill  and  intangible  assets  is  equal  to  the  GAAP  values  provided  above.  The  acquired  goodwill  and 
intangibles will be amortized over a period of 15 years for tax purposes. See Note (9) Goodwill and Intangible Assets, net.

F-18

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

On  July  1,  2019,  a  subsidiary  in  our  insurance  business  acquired  a  majority  interest  in  Ingenasys,  Ltd.,  the  parent  holding 
company  of  Defend  Insurance  Group  (Defend),  for  total  net  cash  consideration  of  approximately  $4,600.  Defend  is  an 
automotive finance and insurance provider and insurance administrator operating in the Czech Republic, Poland, Hungary, 
Slovakia, and the UK. Identifiable assets acquired were primarily made up of goodwill and intangible assets. See Note (9) 
Goodwill and Intangible Assets, net.

(4) Dispositions and Assets and Liabilities Held for Sale

Dispositions

On April 26, 2019, the Company completed the sale of the management contracts and related assets for the CLOs managed 
by  Telos  Asset  Management,  LLC  (Telos).  The  pre-tax  gain  on  sale  for  the  year  ended  December  31,  2019  was  $7,598, 
which is included in other revenue. See (16) Other Revenue and Other Expenses. The sale did not meet the requirements to 
be classified as a discontinued operation.

The  sale  agreement  also  contains  a  provision  which  provides  for  contingent  consideration  if  the  Telos  business  achieves 
specific  performance  metrics.  This  contingent  consideration  represents  a  gain  contingency,  and  the  Company  will  not 
recognize any additional gain unless such consideration is realized.

Assets and Liabilities Held for Sale

The Company has entered into a definitive agreement to sell Luxury, and it is classified as held for sale at December 31, 2021 
and  December  31,  2020.  The  agreement  did  not  meet  the  requirements  to  be  classified  as  a  discontinued  operation.  The 
following  table  presents  detail  of  Luxury’s  assets  and  liabilities  held  for  sale  in  the  consolidated  balance  sheets  for  the 
following periods:

Assets:
Investments:

Loans, at fair value
Other investments

Total investments
Cash, cash equivalents and restricted cash
Notes and accounts receivable, net
Other assets

Assets held for sale

Liabilities:
Debt, net
Other liabilities and accrued expenses (1)

Liabilities held for sale

As of

December 31,
2021

December 31, 
2020

$ 

$ 

$ 

$ 

236,810  $ 
2,071 
238,881 
9,360 
157 
2,210 
250,608  $ 

164,802 
4,345 
169,147 
4,879 
1,760 
5,919 
181,705 

227,973  $ 
15,021 
242,994  $ 

162,072 
13,040 
175,112 

(1) 

Includes deferred tax liabilities of $659 and $939 as of December 31, 2021 and December 31, 2020, respectively.

During  the  year  ended  December  31,  2021  and  December  31,  2020,  the  Company  recorded  an  impairment  of  $1,928  and 
$4,428,  respectively,  related  to  assets  and  liabilities  held  for  sale.  See  Note  (16)  Other  Revenue  and  Other  Expenses.  No 
impairment related to assets and liabilities held for sale was recorded for the year ended December 31, 2019.

Luxury  has  a  total  borrowing  capacity  at  December  31,  2021  of  $299,500.  As  of  December  31,  2021  and  2020,  a  total  of 
$227,973 and $162,072, respectively, was outstanding under such financing agreements.

F-19

 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

(5) 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,  The  Fortegra  Group,  LLC  and  its  subsidiaries  (Fortegra),  is  a  leading  provider  of 
specialty  insurance,  service  contract  products  and  related  service  solutions.  Based  on  the  ASC  280  quantitative  analysis 
performed  as  of  December  31,  2021,  our  reportable  segments  are  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 
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 includes Fortegra Financial Corporation and Fortegra Warranty. 
Fortegra is a leading provider of specialty insurance products and related services. Fortegra designs, markets and underwrites 
specialty  commercial  and  personal  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 origination 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 maritime shipping operations, asset management, other investments (including our Invesque shares), and 
our held-for-sale mortgage operations (Luxury Mortgage).

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: 

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, 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
1,200,514 
(1,085,040) 
(50,132) 
65,342 
21,291 
44,051 
5,919 
38,132 

F-20

 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

For the Year Ended December 31, 2020
Tiptree Capital

Insurance

Mortgage

Other

Total

Total revenues
Total expenses
Corporate expenses
Income (loss) before taxes

$ 

$ 

691,061  $ 
(664,113) 
— 
26,948  $ 

112,165  $ 
(81,063) 
— 
31,102  $ 

7,075  $ 

(68,317) 
— 
(61,242)  $ 

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

$ 

$ 

810,301 
(813,493) 
(35,660) 
(38,852) 
(13,627) 
(25,225) 
3,933 
(29,158) 

For the Year Ended December 31, 2019

Tiptree Capital

Insurance

Mortgage

Other

Total

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

$ 

$ 

635,085  $ 
(598,055) 
— 
37,030  $ 

66,121  $ 
(63,162)   

— 
2,959  $ 

71,522  $ 
(48,131) 
— 
23,391  $ 

$ 

$ 

772,728 
(709,348) 
(34,241) 
29,139 
9,017 
20,122 
1,761 
18,361 

The Company conducts its operations primarily in the U.S. with 7.2%, 5.2%, and 2.9% of total revenues generated overseas 
for the years ended December 31, 2021, 2020 and 2019 respectively.

The following table presents the reportable segments and Tiptree Capital - Other assets for the following periods:

As of December 31, 2021

Tiptree Capital

As of December 31, 2020

Tiptree Capital

Insurance Mortgage

Other

Corporate

Total

Insurance Mortgage

Other

Corporate

Total

Total assets

$ 3,002,152  $  201,134  $  384,564  $  11,297  $ 3,599,147  $ 2,452,798  $  217,138  $  302,068  $  23,756  $ 2,995,760 

F-21

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(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, 2021
Tiptree Capital

Insurance

Mortgage

Other

Total

577,448  $ 
7,099 
109,684 
79,975 
774,206  $ 

—  $ 

98,484 
— 
7,981 
106,465  $ 

—  $ 
— 
28,799 
80,700 
109,499  $ 

577,448 
105,583 
138,483 
168,656 
990,170 

As of December 31, 2020
Tiptree Capital

Insurance

Mortgage

Other

Total

377,133  $ 
7,795 
98,130 
125,833 
608,891  $ 

—  $ 

82,937 
— 
9,439 
92,376  $ 

—  $ 
— 
25,708 
84,429 
110,137  $ 

377,133 
90,732 
123,838 
219,701 
811,404 

$ 

$ 

$ 

$ 

All  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, 2021 and December 31, 2020 are held by subsidiaries in the insurance segment. The following 
tables present the Company's investments in AFS securities:

Allowance for 
Credit 
Losses(1)

As of December 31, 2021
Gross
unrealized 
gains

Gross
unrealized 
losses

Amortized 
cost

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

$ 

$ 

352,288  $ 
57,923 
145,997 
19,511 
2,696 
2,649 
581,064  $ 

—  $ 
— 
(241) 
— 
— 
(4) 
(245)  $ 

2,087  $ 
1,050 
517 
82 
— 
3 
3,739  $ 

(3,197)  $ 
(313) 
(1,396) 
(2,146) 
— 
(58) 
(7,110)  $ 

351,178 
58,660 
144,877 
17,447 
2,696 
2,590 
577,448 

Allowance for 
Credit 
Losses(1)

As of December 31, 2020
Gross
unrealized 
gains

Gross
unrealized 
losses

Amortized 
cost

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

$ 

$ 

191,116  $ 
42,583 
92,761 
37,975 
1,355 
3,961 
369,751  $ 

—  $ 
— 
— 
— 
— 
— 
—  $ 

5,245  $ 
1,768 
2,181 
316 
— 
31 
9,541  $ 

(58)  $ 
(1) 
(1) 
(2,099) 
— 
— 
(2,159)  $ 

196,303 
44,350 
94,941 
36,192 
1,355 
3,992 
377,133 

(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.

F-22

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

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, 2021

December 31, 2020

Amortized 
Cost

Fair Value

Amortized 
Cost

Fair Value

$ 

$ 

41,033  $ 
269,487 
52,561 
198,472 
19,511 
581,064  $ 

41,150  $ 
268,537 
52,000 
198,314 
17,447 
577,448  $ 

30,306  $ 
149,378 
26,621 
125,471 
37,975 
369,751  $ 

30,602 
153,406 
27,479 
129,454 
36,192 
377,133 

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, 2021

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

$  216,378  $ 
17,190 
99,434 
7,454 
1,339 
2,278 
$  344,073  $ 

(2,827) 
(275) 
(1,159) 
(84) 
— 
(58) 
(4,403) 

324  $ 
64 
326 
38 
2 
8 
762  $ 

11,920  $ 
1,152 
9,722 
2,316 
— 
— 
25,110  $ 

(370) 
(38) 
(237) 
(2,062) 
— 
— 
(2,707) 

47 
5 
45 
5 
— 
— 
102 

As of December 31, 2020

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

Total

$ 

$ 

15,323  $ 
379 
901 
— 
16,603  $ 

(58) 
(1) 
(1) 
— 
(60) 

41  $ 
5 
3 
— 
49  $ 

2  $ 
— 
— 
18,927 
18,929  $ 

— 
— 
— 
(2,099) 
(2,099) 

2 
— 
— 
9 
11 

(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, 2021 until full recovery of their amortized cost basis.

F-23

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(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, 2021:

Obligations 
of state and 
political 
subdivisions
$ 

Corporate 
securities

Asset 
backed 
securities

Obligations 
of foreign 
governments

Total

—  $ 

—  $ 

—  $ 

—  $ 

Balance at December 31, 2019
Increase in the allowance for the initial adoption of ASU 
2016-13
Reduction  in  credit  losses  due  to  AFS  securities  sold 
during the year
Gains from recoveries of amounts previously written off 
Balance at December 31, 2020

Balance at December 31, 2020
(Increase) in allowance for credit losses
Reduction  in  credit  losses  due  to  AFS  securities  sold 
during the year
Gains from recoveries of amounts previously written off
Balance at December 31, 2021

(1) 

— 
1 

—  $ 

—  $ 
— 

— 
— 
—  $ 

(50) 

3 
47 
—  $ 

—  $ 

(296) 

3 
52 
(241)  $ 

(2) 

— 
2 

—  $ 

—  $ 
— 

— 
— 
—  $ 

— 

— 
— 
—  $ 

—  $ 
(6) 

1 
1 
(4)  $ 

$ 

$ 

$ 

— 

(53) 

3 
50 
— 

— 
(302) 

4 
53 
(245) 

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:

Net gains from recoveries (credit losses) on AFS securities

For the Year Ended December 31, 

2021

2020

$ 

(245)  $ 

53 

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

As of December 31,
2020
2021

$ 

$ 

42,471  $ 

7,189 

49,660  $ 

44,349 
9,447 
53,796 

The following table presents additional information on the Company’s AFS securities:

For the Year Ended December 31,
2020

2019

2021

Purchases of AFS securities

Proceeds from maturities, calls and prepayments of AFS securities

Gross proceeds from sales of AFS securities

$ 

$ 

$ 

368,913  $ 

158,357  $ 

253,415 

68,923  $ 

84,923  $ 

36,459 

86,981  $ 

35,603  $ 

170,495 

F-24

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

The following table presents the gross realized gains and gross realized losses from sales and redemptions of AFS securities: 

For the Year Ended December 31, 
2020

2019

2021

Gross realized gains
Gross realized (losses)

Total net realized gains (losses) from investment sales and redemptions

$ 

$ 

661  $ 
(23) 
638 

594  $ 
(66)   
528 

1,558 
(246) 
1,312 

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, 2021

As of December 31, 2020

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

$  7,099  $  10,156  $ 

(3,057)  $ 

—  $  7,795  $  12,281  $ 

(4,486)  $ 

— 

Insurance:

Corporate loans (1)

Mortgage:

Mortgage loans held for sale (2)
Total loans, at fair value

  98,484 
$ 105,583  $  105,420  $ 

95,264 

3,220 

95,542 

  82,937 

78,590 

163  $  95,542  $  90,732  $  90,871  $ 

81,630 
4,347 
(139)  $  81,630 

(1) 

(2) 

The cost basis of Corporate loans was approximately $9,094 and $11,282 at December 31, 2021 and December 31, 2020, respectively. 
As of December 31, 2021 and December 31, 2020, there was one mortgage loan held for sale and two mortgage loans held for sale that were 90 days or more past due, 
respectively, with a fair value of $136 and $534, respectively.

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 17.0 million shares of Invesque as of December 31, 2021 and December 31, 
2020, 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 operations and other Tiptree investing activity as of the 
following periods:

As of December 31, 2021
Tiptree Capital - Other

Total

Fair Value

Fair Value

Cost
111,491  $ 
— 
— 
111,491  $ 

28,799  $ 
— 
— 
28,799  $ 

As of December 31, 2020
Tiptree Capital - Other

Cost
111,491  $ 
— 
— 
111,491  $ 

25,708  $ 
— 
— 
25,708  $ 

Cost
134,830  $ 
52,176 
49,664 

236,670  $ 

Total

Cost
134,830  $ 
62,438 
38,069 
235,337  $ 

34,814 
53,154 
50,515 
138,483 

31,078 
63,875 
28,885 
123,838 

Fair Value

Fair Value

Invesque
Fixed income exchange traded fund
Other equity securities

Total equity securities

Invesque
Fixed income exchange traded fund
Other equity securities

Total equity securities

Insurance

Cost

Fair Value

23,339  $ 
52,176 
49,664 
125,179  $ 

6,015  $ 

53,154 
50,515 
109,684  $ 

Insurance

Cost

Fair Value

23,339  $ 
62,438 
38,069 
123,846  $ 

5,370  $ 

63,875 
28,885 
98,130  $ 

$ 

$ 

$ 

$ 

F-25

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(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)
Vessels, net (2)
Debentures
Trade claims
Other

Total other investments

Corporate bonds, at fair value (1)
Vessels, net (2)
Debentures
Other

Total other investments

As of December 31, 2021
Tiptree Capital

Insurance

Mortgage

Other

Total

38,965  $ 
— 
21,057 
19,737 
216 
79,975  $ 

—  $ 
— 
— 
— 
7,981 
7,981  $ 

—  $ 

79,368 
— 
— 
1,332 
80,700  $ 

38,965 
79,368 
21,057 
19,737 
9,529 
168,656 

As of December 31, 2020
Tiptree Capital

Insurance

Mortgage

Other

Total

105,777  $ 
— 
17,703 
2,353 
125,833  $ 

—  $ 
— 
— 
9,439 
9,439  $ 

—  $ 

83,028 
— 
1,401 
84,429  $ 

105,777 
83,028 
17,703 
13,193 
219,701 

$ 

$ 

$ 

$ 

(1) 

(2)  

The cost basis of corporate bonds was $36,436 and $97,284 as of December 31, 2021 and December 31, 2020, respectively.
Net of accumulated depreciation of $13,059 and $8,372 as of December 31, 2021 and December 31, 2020, 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, 
2020

2019

2021

Interest:

AFS securities
Loans, at fair value
Other investments

Dividends from equity securities
Other

Subtotal

Less: investment expenses

Net investment income

Other Investment Income - Tiptree Capital

$ 

$ 

7,153  $ 
802 
5,792 
7,355 
— 
21,102 
3,206 
17,896  $ 

7,685  $ 
801 
4,245 
1,482 
8 
14,221 
4,305 
9,916  $ 

8,404 
3,284 
1,218 
2,813 
— 
15,719 
1,702 
14,017 

Other  investment  income  represents  other  revenue  from  other  Tiptree  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:

F-26

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

For the Year Ended December 31, 
2020

2019

2021

Interest:

Loans, at fair value (1)
Other

Dividends from equity securities
Loan fee income
Vessel related revenue

Other investment income

$ 

$ 

7,184  $ 
— 
— 
21,834 
35,562 
64,580  $ 

5,617  $ 
— 
2,533 
17,900 
22,697 
48,747  $ 

6,206 
269 
10,132 
12,631 
16,747 
45,985 

(1) 

Primarily relates to Loans, at fair value classified as Held for Sale. See Note (4) Dispositions and Assets and Liabilities Held for Sale.

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, 
2020

2019

2021

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)
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)

$ 

638  $ 
(245) 
(389) 
(10,434) 
3,917 
1,346 

528  $ 
53 
(945) 
(24,586) 
7,299 
2,511 

91,538 
2,165 

61,312 
1,632 
151,480 

1,330 
12,445 
(814) 
(9,800) 

111,725 
(10,314) 

40,466 
(4,713) 
122,024 

(1,461) 
(22,793) 
17,290 
10,162 

(1,127) 
(268) 

1,270 
(6,093) 

815 
3,090 
(5,801) 
(130) 
151,350  $ 

2,185 
(67,656) 
7,482 
(59,614) 
62,410  $ 

$ 

1,312 
— 
2,100 
947 
279 
39 

52,617 
— 

23,403 
(260) 
80,437 

(3,899) 
7,621 
(807) 
(697) 

840 
357 

983 
(992) 
25 
3,431 
83,868 

(1) 

Relates to Loans, at fair value classified as Held for Sale. See Note (4) Dispositions and Assets and Liabilities Held for Sale.

F-27

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(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 - premium financing program
Trust receivables
Other receivables

Total notes and accounts receivable, net

As of December 31,
2020
2021

$ 

$ 

137,082  $ 
157,853 
89,788 
41,889 
27,757 
454,369  $ 

95,269 
131,760 
62,075 
54,393 
26,955 
370,452 

The following table presents the total valuation allowance and bad debt expense for the following periods:

Valuation allowance
As of December 31,
2020
2021

Bad Debt Expense
For the Year Ended December 31,
2019
2020
2021

Notes receivable, net - premium financing program (1)

Accounts and premiums receivable, net

$ 

$ 

123  $ 

120  $ 

101  $ 

169  $ 

274  $ 

223  $ 

33  $ 

28  $ 

175 

36 

(1) 

As of December 31, 2021 and December 31, 2020, there were $1,311 and $215 in balances classified as 90 days plus past due, respectively.

(8) Reinsurance Receivables

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, 2021
Life insurance in force
For the Year ended December 31, 2021
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, 2020
Life insurance in force
For the Year Ended December 31, 2020
Premiums written:
Life insurance
Accident and health insurance
Property and liability insurance
Total premiums written

Direct amount

Ceded to other 
companies

Assumed from 
other 
companies

Net amount

Percentage of 
amount - 
assumed to net

$ 

5,921,446  $ 

3,068,761  $ 

—  $ 

2,852,685 

$ 

$ 

$ 

$ 

91,865  $ 
146,256 
1,141,979 
1,380,100  $ 

46,920  $ 
100,717 
558,471 
706,108  $ 

808  $ 

5,790 
214,150 
220,748  $ 

45,753 
51,329 
797,658 
894,740 

74,151  $ 
126,501 
902,439 
1,103,091  $ 

39,881  $ 
85,457 
504,785 
630,123  $ 

1,194  $ 
7,219 
204,171 
212,584  $ 

35,464 
48,263 
601,825 
685,552 

$ 

5,153,151  $ 

2,985,196  $ 

—  $ 

2,167,955 

$ 

$ 

69,704  $ 
117,235 
825,845 
1,012,784  $ 

39,761  $ 
78,233 
509,818 
627,812  $ 

1,550  $ 
12,696 
144,332 
158,578  $ 

31,493 
51,698 
460,359 
543,550 

 1.8 %
 11.3 %
 26.8 %
 24.7 %

 3.4 %
 15.0 %
 33.9 %
 31.0 %

 4.9 %
 24.6 %
 31.4 %
 29.2 %

F-28

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

Premiums earned:
Life insurance
Accident and health insurance
Property and liability insurance
Total premiums earned

As of December 31, 2019
Life insurance in force
For the Year Ended December 31, 2019
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

$ 

$ 

68,637  $ 
118,183 
691,310 
878,130  $ 

37,194  $ 
78,365 
405,469 
521,028  $ 

1,437  $ 
11,599 
107,853 
120,889  $ 

32,880 
51,417 
393,694 
477,991 

$ 

5,176,056  $ 

2,884,009  $ 

—  $ 

2,292,047 

$ 

$ 

75,060  $ 
133,514 
709,515 
918,089 

40,555  $ 
87,447 
350,093 
478,095 

1,692  $ 
3,201 
92,246 
97,139 

36,197 
49,268 
451,668 
537,133 

68,282 
123,182 
597,852 
789,316  $ 

35,929 
82,660 
242,180 
360,769  $ 

1,607 
3,165 
65,789 
70,561  $ 

33,960 
43,687 
421,461 
499,108 

 4.4 %
 22.6 %
 27.4 %
 25.3 %

 4.7 %
 6.5 %
 20.4 %
 18.1 %

 4.7 %
 7.2 %
 15.6 %
 14.1 %

The following table presents the components of policy and contract benefits, including the effect of reinsurance on losses and 
loss adjustment expenses (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

Direct 
amount

Ceded to 
other 
companies

Assumed 
from other 
companies

Net amount

Percentage of 
amount - 
assumed to net

$ 

59,526  $ 
21,509 
354,308 
435,343 

34,030  $ 
18,091 
239,678 
291,799 

869  $ 

2,225 
106,835 
109,929 

Member benefit claims (1)
Total policy and contract benefits

$ 

26,365 
5,643 
221,465 
253,473 
73,539 
327,012 

 3.3 %
 39.4 %
 48.2 %
 43.4 %

F-29

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

For the Year Ended December 31, 2020
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, 2019
Losses and LAE Incurred

Life insurance                   
Accident and health insurance    
Property and liability insurance 
Total losses and LAE incurred 

Direct 
amount

Ceded to 
other 
companies

Assumed 
from other 
companies

Net amount

Percentage of 
amount - 
assumed to net

$ 

46,268  $ 
18,354 
282,906 
347,528 

27,292  $ 
15,715 
182,115 
225,122 

645  $ 

7,032 
48,165 
55,842 

Member benefit claims (1)
Total policy and contract benefits

$ 

$ 

38,306  $ 
18,832 
225,200 
282,338 

22,607  $ 
15,022 
147,290 
184,919 

443  $ 
362 
52,785 
53,590 

Member benefit claims (1)
Total policy and contract benefits

$ 

19,621 
9,671 
148,956 
178,248 
58,650 
236,898 

16,142 
4,172 
130,695 
151,009 
19,672 
170,681 

 3.3 %
 72.7 %
 32.3 %
 31.3 %

 2.7 %
 8.7 %
 40.4 %
 35.5 %

(1)  Member benefit claims are not covered by reinsurance.

The following table presents the components of the reinsurance receivables:

Prepaid reinsurance premiums:

Life insurance (1)
Accident and health insurance (1)
Property and liability insurance

Total

Ceded claim reserves:
Life insurance
Accident and health insurance
Property and liability insurance

Total ceded claim reserves recoverable

Other reinsurance settlements recoverable
Reinsurance receivables

(1)

Including policyholder account balances ceded.

As of December 31,
2020
2021

$ 

$ 

73,478  $ 
81,521 
479,091 
634,090 

3,928 
12,239 
148,962 
165,129 
81,617 
880,836  $ 

70,066 
66,261 
423,868 
560,195 

4,133 
11,118 
98,092 
113,343 
54,471 
728,009 

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, 
2021

$ 

126,089 

As of December 31, 2021, the non-affiliated reinsurers from whom our insurance business has the largest receivable balances 
were:  Allianz  Global  Corporate  &  Specialty  SE  (A.  M.  Best  Rating:  A+  rated),  Canada  Life  International  Reinsurance 
(Bermuda) Corporation (A. M. Best Rating: A+ rated), and Canada Life Assurance Company (A. M. Best Rating: A+ rated). 
The  related  receivables  of  these  reinsurers  are  collateralized  by  assets  on  hand,  assets  held  in  trust  accounts  and  letters  of 
credit.  As of December 31, 2021, 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.

F-30

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

(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:

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

As of December 31, 2021
Other

Total

Insurance

As of December 31, 2020
Other

Total

Insurance

$ 

143,300  $ 
(45,997)   
14,750 
(5,633)   
9,300 
(8,790)   
36,500 
(36,320)   
640 
(203)   

107,547 

—  $ 
— 
800 
(520)   
640 
(594)   
— 
— 
— 
— 
326 

143,300  $ 
(45,997) 
15,550 
(6,153) 
9,940 
(9,384) 
36,500 
(36,320) 
640 
(203) 
107,873 

143,300  $ 
(32,263) 
14,750 
(4,382) 
9,300 
(8,650) 
36,500 
(36,238) 
640 
— 
122,957 

—  $ 
— 
800 
(440) 
640 
(503) 
— 
— 
— 
— 
497 

13,761 
— 
13,761 

— 
1,124 
1,124 

13,761 
1,124 
14,885 

13,761 
— 
13,761 

— 
1,000 
1,000 

143,300 
(32,263) 
15,550 
(4,822) 
9,940 
(9,153) 
36,500 
(36,238) 
640 
— 
123,454 

13,761 
1,000 
14,761 

Total intangible assets, net

$ 

121,308  $ 

1,450  $ 

122,758  $ 

136,718  $ 

1,497  $ 

138,215 

Goodwill 

Total goodwill and intangible assets, net

$ 

177,395 
298,703  $ 

1,708 
3,158  $ 

179,103 
301,861  $ 

177,528 
314,246  $ 

1,708 
3,205  $ 

179,236 
317,451 

(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, 2019

Goodwill acquired (1)
Purchase accounting adjustments (2)

Balance at December 31, 2020

Purchase accounting adjustment (2)

Balance at December 31, 2021

Accumulated impairments

Insurance

Tiptree Capital
Other

Total

97,439 
84,476 
(4,387) 
177,528  $ 
(133) 
177,395  $ 

1,708 
— 
— 
1,708  $ 
— 
1,708  $ 

99,147 
84,476 
(4,387) 
179,236 
(133) 
179,103 

—  $ 

699  $ 

699 

$ 

$ 

$ 

(1)    Relates to acquisitions in in our insurance business as of December 31, 2020. See Note (3) Acquisitions.
(2)   Relates to adjustments during the measurement period as permitted under ASC 805 for the final valuation of acquisitions in our insurance business as of January 3, 2020 and 

December 31, 2020.

The  Company  conducts  annual  impairment  tests  of  its  goodwill  as  of  October  1.  For  the  years  ended  December  31,  2021, 
2020 and 2019, no impairments were recorded on the Company’s goodwill.

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:

F-31

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

Balance at December 31, 2019
Intangible assets acquired (1)
Purchase accounting adjustment (2)
Less: amortization expense
Balance at December 31, 2020

Intangibles acquired
Less: amortization expense 
Balance at December 31, 2021

Insurance

Other

Total

$ 

$ 

$ 

47,305  $ 
99,040 
(300) 
(9,327) 
136,718  $ 
— 
(15,410) 
121,308  $ 

669  $ 

1,000 
— 
(172) 
1,497  $ 
124 
(171) 
1,450  $ 

47,974 
100,040 
(300) 
(9,499) 
138,215 
124 
(15,581) 
122,758 

(1)    Relates to acquisitions in in our insurance business as of December 31, 2020. See Note (3) Acquisitions.
(2)   Relates to adjustments during the measurement period as permitted under ASC 805 for the final valuation of acquisitions in our insurance business as of July 1, 2019.

The following table presents the amortization expense on finite-lived intangible assets for the following periods:

Amortization expense on intangible assets

$ 

15,581  $ 

9,499  $ 

7,897 

For the years ended December 31, 2021, 2020 and 2019, 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:

For the Year Ended December 31,

2021

2020

2019

2022
2023
2024
2025
2026
2027 and thereafter

Total

As of December 31, 2021
Other

Insurance

Total

$ 

$ 

15,848  $ 
15,031 
13,344 
11,229 
9,003 
43,092 
107,547  $ 

126  $ 
80 
80 
40 
— 
— 
326  $ 

15,974 
15,111 
13,424 
11,269 
9,003 
43,092 
107,873 

(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 classified by underlying credit risk and interest rate risk. In addition, the Company is also subject to 
additional counterparty risk should its counterparties fail to meet the contract terms. The derivative financial instruments are 
reported in other investments. Derivative liabilities are reported within other liabilities and accrued expenses.

Derivatives, at fair value

Interest Rate Lock Commitments

The Company enters into interest rate lock commitments (IRLCs) with customers in connection with its mortgage banking 
activities  to  fund  residential  mortgage  loans  with  certain  terms  at  specified  times  in  the  future.  IRLCs  that  relate  to  the 
origination of mortgage loans that will be classified as held-for-sale are considered derivative instruments under applicable 
accounting  guidance.  As  such,  these  IRLCs  are  recorded  at  fair  value  with  changes  in  fair  value  typically  resulting  in 
recognition of a gain when the Company enters into IRLCs. In estimating the fair value of an IRLC, the Company assigns a 
probability that the loan commitment will be exercised and the loan will be funded (“pull through”). The fair value of the 
commitments is derived from the fair value of related mortgage loans, net of estimated costs to complete. Outstanding IRLCs 
expose the Company to the risk that the price of the loans underlying the commitments might decline from inception of the 
rate lock to funding of the loan. To manage this risk, the Company utilizes forward delivery contracts and to be announced 
(TBA) mortgage backed securities to economically hedge the risk of potential changes in the value of the loans that would 

F-32

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

result from the commitments. 

Forward Delivery Contracts and TBA Mortgage Backed Securities

The Company enters into forward delivery contracts with loan aggregators and other investors as one of the tools to manage 
the  interest  rate  risk  associated  with  IRLCs  and  loans  held  for  sale.  In  addition,  the  Company  enters  into  TBA  mortgage 
backed securities which facilitate hedging and funding by allowing the Company to prearrange prices for mortgages that are 
in the process of originating. The Company utilizes these hedging instruments for Agency (Fannie Mae and Freddie Mac) and 
FHA/VA (Ginnie Mae) eligible IRLCs.

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, 2021

As of December 31, 2020

Notional
values

Asset 
derivatives

Liability
derivatives

Notional
values

Asset 
derivatives

Liability
derivatives

Interest rate lock commitments
Forward delivery contracts
TBA mortgage backed securities
Other

Total

$ 

$ 

268,878  $ 

56,593 
316,000 
9,232 
650,703  $ 

7,514  $ 
204 
262 
216 
8,196  $ 

—  $ 
59 
425 
1,657 
2,141  $ 

219,929  $ 
35,979 
291,000 
3,058 
549,966  $ 

9,207  $ 
— 
232 
2,090 
11,529  $ 

— 
22 
1,508 
560 
2,090 

F-33

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(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)
Secured term credit agreements (LIBOR + 6.75%)(2)
Preferred trust securities (LIBOR + 4.10%)
8.50% Junior subordinated notes 
Total corporate debt

Asset based debt (3)

Asset based revolving financing (LIBOR + 2.75%)
Residential mortgage warehouse borrowings (LIBOR + 1.88% to 3.00%) (2)(3)
Vessel backed term loan (LIBOR + 4.75%)
Total asset based debt

Total debt, face value
Unamortized discount, net
Unamortized deferred financing costs

Total debt, net

Corporate debt

Secured revolving credit agreements (1)
Secured term credit agreements (LIBOR + 6.75%)(2)
Preferred trust securities (LIBOR + 4.10%)
8.50% Junior subordinated notes 
Total corporate debt

Asset based debt (3)

Asset based revolving financing (LIBOR + 2.75%)
Residential mortgage warehouse borrowings (LIBOR + 1.88% to 3.00%) (2)(3)
Vessel backed term loan (LIBOR + 4.75%)
Total asset based debt

Total debt, face value
Unamortized discount, net
Unamortized deferred financing costs

Total debt, net

As of December 31, 2021

Insurance
$ 

2,160  $ 
— 
35,000 
125,000 
162,160 

Other

Corporate

Total

—  $ 
— 
— 
— 
— 

—  $ 

114,063 
— 
— 
114,063 

2,160 
114,063 
35,000 
125,000 
276,223 

42,310 
— 
— 
42,310 
204,470 
— 
(8,474) 
$  195,996  $ 

42,310 
— 
72,518 
72,518 
13,600 
13,600 
128,428 
86,118 
404,651 
86,118 
(1,458) 
— 
(1,069) 
(9,844) 
85,049  $  112,304  $  393,349 

— 
— 
— 
— 
114,063 
(1,458) 
(301) 

As of December 31, 2020

Insurance
$ 

—  $ 
— 
35,000 
125,000 
160,000 

Other

Corporate

Total

—  $ 
— 
— 
— 
— 

—  $ 

120,313 
— 
— 
120,313 

— 
120,313 
35,000 
125,000 
280,313 

27,510 
— 
— 
27,510 
187,510 
— 
(9,537) 
$  177,973  $ 

— 
55,994 
15,800 
71,794 
71,794 
— 
(5) 

27,510 
— 
55,994 
— 
15,800 
— 
99,304 
— 
379,617 
120,313 
(2,035) 
(2,035) 
(11,336) 
(1,794) 
71,789  $  116,484  $  366,246 

(1) 

(2) 

(3) 

The secured revolving credit agreements provide a two rate structure at the Company’s discretion; Prime +1.25% for swing loans and LIBOR + 2.25%.
Includes LIBOR floor of 1.00%.
The  weighted  average  coupon  rate  for  residential  mortgage  warehouse  borrowings  was  2.76%  and  2.75%  at  December  31,  2021  and  December  31,  2020,  respectively. 
Includes LIBOR floor ranging from 0.50% to 1.00%

The following table presents the amount of interest expense the Company incurred on its debt for the following periods:

Total Interest expense - corporate debt
Total Interest expense - asset based debt

Interest expense on debt

For the Year Ended December 31,

2021

2020

2019

24,425  $ 
13,018 
37,443  $ 

23,322  $ 
9,260 
32,582  $ 

19,682 
7,377 
27,059 

$ 

F-34

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(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: 

2022
2023
2024
2025
2026
2027 and thereafter

Total

As of
December 31, 
2021

$ 

$ 

80,968 
52,920 
15,450 
95,313 
— 
160,000 
404,651 

The following narrative is a summary of certain terms of our debt agreements for the year ended December 31, 2021:

Corporate Debt

Secured Revolving Credit Agreements

As  of  December  31,  2021  and  December  31,  2020,  a  total  of  $2,160  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, 2021 is $200,000.

On August 4, 2020, Fortegra entered into an Amended and Restated Credit Agreement by and among Fortegra Financial 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 $17,500 for swing loans and matures on August 4, 2023. The 
Fortegra  Credit  Agreement  replaced  the  $30,000  revolving  line  of  credit  with  the  Fifth  Third  Bank  (the  “Working  Capital 
Facility”).

Secured Term Credit Agreement

On February 21, 2020, the Operating Company borrowed $125,000 under a new credit agreement (Credit Agreement) with 
Fortress Credit Corp. (Fortress). The proceeds were used to repay the Company’s prior credit agreement with Fortress, with a 
balance  of  $68,210  as  of  December  31,  2019,  and  for  working  capital  and  general  corporate  purposes.  Pursuant  to  an 
Amendment, Assumption and Consent Agreement, dated July 17, 2020 by and among Tiptree, certain of its subsidiaries and 
Fortress, Tiptree Holdings LLC (Tiptree Holdings) became the borrower under the Credit Agreement, dated as of February 
21, 2020, by and among Tiptree, certain of its subsidiaries and Fortress. The Credit Agreement will mature on February 21, 
2025,  with  principal  amounts  of  the  loans  to  be  repaid  in  consecutive  quarterly  installments.  Loans  under  the  Credit 
Agreement bear interest at a variable rate per annum equal to LIBOR (with a minimum LIBOR rate of 1.00%), plus a margin 
of 6.75% per annum. The obligations under the Credit Agreement are secured by liens on substantially all of the assets of 
Tiptree  Holdings  and  guaranteed  by  the  Company  and  Tiptree  Holdings’  direct  wholly  owned  first  tier  subsidiaries 
(Guarantors). 

The Credit Agreement contains various customary affirmative and negative covenants of the Company, Tiptree Holdings and 
the  other  Guarantors  (subject  to  customary  exceptions),  including,  but  not  limited  to,  limitations  on  indebtedness,  liens, 
investments and acquisitions, negative pledges, junior payments, conduct of business, transactions with affiliates, dispositions 
of  assets,  prepayment  of  certain  indebtedness  and  limits  on  guarantees  by  subsidiaries  of  Tiptree  Holdings’  and  the 
Guarantors’  indebtedness.  The  Credit  Agreement  also  contains  a  financial  covenant  which  limits  corporate  leverage  as 
defined by its Corporate Leverage Ratio (as defined in the Credit Agreement). 

The  Credit  Agreement  also  contains  customary  mandatory  repayment  provisions  (subject  to  customary  exceptions)  and 
requires that net cash proceeds from the sale by Tiptree and certain of its subsidiaries of capital stock of Invesque be applied 
to prepay loans until the outstanding principal amount of loans is $62,500, with remaining proceeds subject to reinvestment 
rights. Prepayments, whether mandatory or voluntary, reduce future scheduled amortization payments in the order they come 

F-35

 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

due.  The  Credit  Agreement  also  requires  the  payment  of  a  prepayment  fee  upon  a  repricing  transaction  or  equity  issuance 
consummated after the closing date, or the sale of Fortegra, or any of its material subsidiaries. As of December 31, 2021, a 
total of $114,063 was outstanding under this agreement. The maximum borrowing capacity on this agreement is $114,063.

Junior Subordinated Notes

A  subsidiary  in  our  insurance  business  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,  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  subsidiary’s  current  and  future  senior  indebtedness.  The  notes  are  not  obligations  of  or 
guaranteed by any subsidiaries of the subsidiary, 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

A  subsidiary  in  our  insurance  business  has  $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.

Asset Based Debt

Asset Backed Revolving Financing

On  October  16,  2020,  subsidiaries  in  our  insurance  business  entered  into  a  three  year  $75,000  secured  credit  agreement, 
which replaced the individual agreements in its premium finance and 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 our premium finance business and up 
to $55,000 for our service contract finance business, and is secured by substantially all of the assets of the borrowers. The 
obligations  under  the  agreement  are  non-recourse  to  Fortegra  and  its  subsidiaries  (other  than  borrowers  and  their 
subsidiaries). As of December 31, 2021, a total of $42,310 was outstanding under the borrowing.

Residential Mortgage Warehouse Borrowings

In March 2021, the $60,000 warehouse line of credit was renewed and the maturity date was extended from April 2021 to 
April 2022. In July 2021, the $50,000 warehouse line of credit was renewed and the maturity date was extended from August 
2021 to August 2022. 

In April 2020, a subsidiary in our mortgage business renewed the $60,000 warehouse line of credit, extending the maturity 
date  to  April  2021  and  establishing  a  LIBOR  floor  of  1.0%.  Additionally,  during  March  2020,  another  warehouse  line 
maturing  in  August  2020  temporarily  raised  the  maximum  borrowing  capacity  to  $65,000,  returning  to  a  maximum 
borrowing  capacity  of  $50,000  in  May  2020  and  establishing  a  LIBOR  floor  of  0.50%.  In  August  2020,  the  $50,000 
warehouse  line  of  credit  was  extended  to  August  2021,  and  established  a  LIBOR  floor  of  0.50%  to  1.00%.  As  of 
December  31,  2021  and  December  31,  2020,  a  total  of  $72,518  and  $55,994,  respectively,  was  outstanding  under  such 
financing agreements.

F-36

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

Vessel Backed Term Loan

On November 28, 2019, subsidiaries in our shipping business entered into a $18,000 term loan facility. Amounts borrowed 
under the facility are not allowed to be reborrowed. The borrowing has a maturity date of November 28, 2024 and a rate of 
LIBOR plus 4.75%, with quarterly principal payments of $550. This facility is secured by liens on 2.00 of our vessels as well 
as  the  assets  of  the  borrowing  entities  and  their  parent  guarantor.  This  credit  agreement  contains  customary  financial 
covenants that require, among other items, minimum liquidity, positive working capital, minimum required security coverage 
ratio of 150%, and the existence of a maintenance reserve account funded on a quarterly basis prior to anticipated scheduled 
drydocking costs. As of December 31, 2021, a total of $13,600 was outstanding under the borrowing.

As of December 31, 2021, the Company is in compliance with the representations and covenants for its outstanding debt or 
has obtained waivers for any events of non-compliance.

(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 
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. 

F-37

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

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  obtained  from  an  independent 
pricing service using unobservable inputs 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 which include 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  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 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. 

Corporate Bonds

Corporate bonds are generally classified under Level 2 in the fair value hierarchy 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.

F-38

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

Trade Claims

Trade claims represent unsecured claims of bankrupt companies and are generally classified under Level 3 in the fair value 
hierarchy.  The  fair  value  is  determined  using  valuation  methodologies  that  consider  a  range  of  factors,  including  but  not 
limited to the price at which the investment was acquired, the nature of the investment, local market conditions, current and 
projected operating performance, and financing transactions subsequent to the acquisition of the investment. The inputs are 
intended to reflect the assumptions a market participant would use in pricing the asset or liability.

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. 

The following tables present the Company’s fair value hierarchies for financial assets and liabilities, measured on a recurring 
basis: 

F-39

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(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
Trade claims
CLOs
Total other investments, at fair value

Mortgage servicing rights (1)

Total

Liabilities: (2)
Securities sold, not yet purchased
Derivative liabilities
Contingent consideration payable

Total

(1) 

(2) 

Included in other assets.
Included in other liabilities and accrued expenses.

As of December 31, 2021

Quoted prices 
in active 
markets 
Level 1

 Other 
significant
 observable 
inputs 
 Level 2 

 Significant 
unobservable 
inputs
Level 3

Fair value

$ 

$ 

$ 

$ 

—  $ 
— 
— 
2,696 
— 
— 
2,696 

351,178  $ 
58,660 
2,590 
— 
16,832 
144,877 
574,137 

—  $ 
— 
— 
— 
615 
— 
615 

— 
— 
— 

5,002 
98,484 
103,486 

34,814 
53,154 
49,309 
137,277 

— 
113 
— 
— 
113 

— 

— 
— 
— 
— 

38,965 
569 
— 
— 
39,534 

— 

2,097 
— 
2,097 

— 
— 
1,206 
1,206 

— 
7,514 
19,737 
441 
27,692 

29,833 

351,178 
58,660 
2,590 
2,696 
17,447 
144,877 
577,448 

7,099 
98,484 
105,583 

34,814 
53,154 
50,515 
138,483 

38,965 
8,196 
19,737 
441 
67,339 

29,833 

140,086  $ 

717,157  $ 

61,443  $ 

918,686 

242  $ 
— 
— 
242  $ 

—  $ 

2,141 
— 
2,141  $ 

—  $ 
— 
200 
200  $ 

242 
2,141 
200 
2,583 

F-40

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(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
CLOs
Total other investments, at fair value

Mortgage servicing rights (1)

Total

Liabilities: (2)
Securities sold, not yet purchased
Derivative liabilities 
Contingent consideration payable

Total

(1)        Included in other assets.
(2)        Included in other liabilities and accrued expenses.

Quoted
prices in
active
markets 
Level 1

As of December 31, 2020
 Other 
significant
 observable 
inputs 
 Level 2 

 Significant 
unobservable 
inputs
Level 3

Fair value

$ 

$ 

$ 

$ 

—  $ 
— 
— 
1,355 
— 
— 
1,355 

196,303  $ 
44,350 
3,992 
— 
35,334 
94,941 
374,920 

—  $ 
— 
— 
— 
858 
— 
858 

— 
— 
— 

— 
82,937 
82,937 

31,078 
63,875 
28,850 
123,803 

— 
2,090 
— 
2,090 

— 

— 
— 
— 
— 

105,777 
232 
— 
106,009 

— 

7,795 
— 
7,795 

— 
— 
35 
35 

— 
9,207 
802 
10,009 

14,758 

196,303 
44,350 
3,992 
1,355 
36,192 
94,941 
377,133 

7,795 
82,937 
90,732 

31,078 
63,875 
28,885 
123,838 

105,777 
11,529 
802 
118,108 

14,758 

127,248  $ 

563,866  $ 

33,455  $ 

724,569 

16,479  $ 
— 
— 
16,479  $ 

30,158  $ 
2,090 
— 
32,248  $ 

—  $ 
— 
200 
200  $ 

46,637 
2,090 
200 
48,927 

F-41

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(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
Conversions to mortgage loans held for sale

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

2021

2020

$ 

33,455  $ 

32,470 

14,206 
(243) 
109,330 
24,956 
(9,238) 
(111,023) 

61,443  $ 

2,253 
(329) 
120,267 
3,862 
(6,672) 
(118,396) 
33,455 

(2,421)  $ 
(243)  $ 

(7,978) 
(329) 

$ 

$ 
$ 

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. 

Assets

IRLCs

As of December 31,
2020
2021

Fair Value

$ 

7,514  $ 

9,207 

Mortgage servicing 
rights

29,833 

14,758 

Valuation 
technique
Internal 
model

External 
model

Unobservable 
input(s) (1)
Pull through 
rate
Discount rate
Cost to service
Prepayment 
speed 

As of December 31,

2021

2020

Range

WA

Range

WA

55% to

95% 66% 50% to

95% 68%

10% to
$65
to

12%
$80

9%
$71

10% to
$75
to

13% 11%
$82
$90

5% to

100% 15%

8% to

60% 22%

Trade claims

19,737 

— 

Internal 
model

Plan projected 
recovery rate

15% to

18% 17%

N/A

N/A

Total

$ 

57,084  $ 

23,965 

Liabilities

Contingent 
consideration 
payable - Smart 
AutoCare

Total

$ 

$ 

200  $ 

200 

200  $ 

200 

 Cash 
Flow 
Model
Actuarial 
Analysis

Forecast Cash 
EBITDA

Assumed 
Claim 
Liabilities 

(1) 

Unobservable inputs were weighted by the relative fair value of the instruments.

$20,000 to $30,000 N/A $20,000 to $30,000 N/A

$55,000

$55,000

F-42

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

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, 2021

As of December 31, 2020

Level within
fair value
hierarchy

Fair value

Carrying 
value

Level within
fair value
hierarchy

Fair value

Carrying 
value

2
2

3

$ 

$ 

$ 
$ 

21,057  $ 
89,788 

110,845  $ 

21,057 
89,788 
110,845 

419,599  $ 
419,599  $ 

403,193 
403,193 

2
2

3

$ 

$ 

$ 
$ 

17,703  $ 
62,075 
79,778  $ 

17,703 
62,075 
79,778 

392,951  $ 
392,951  $ 

377,582 
377,582 

Assets:

Debentures (1)
Notes receivable, net

Total assets

Liabilities:
Debt, net

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 LIBOR based 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-43

 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(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, 

2021

2020

$ 

$ 

233,438  $ 
(5,419) 
(30,664) 
197,355 
(113,163) 
(247) 
83,945 

250,300 
2,606 
252,906 

174,334 
8,105 
182,439 

154,412 
165,129 
576 
320,117 
801 
10,785 
331,703  $ 

144,384 
(11,589) 
(85) 
132,710 
(88,599) 
(230) 
43,881 

172,007 
5,443 
177,450 

127,721 
9,665 
137,386 

83,945 
113,163 
247 
197,355 
5,419 
30,664 
233,438 

The following schedule reconciles the total 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, 

2021

2020

2019

$ 

$ 

252,906  $ 
(284) 
851 
253,473  $ 

177,450  $ 
27 
771 
178,248  $ 

150,094 
184 
731 
151,009 

During  the  year  ended  December  31,  2021,  the  Company  experienced  an  increase  in  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 
personal and commercial lines of business.

During  the  year  ended  December  31,  2020,  the  Company  experienced  an  increase  in  prior  year  development  of  $5,443, 
primarily  as  a  result  of  higher  than  expected  claim  frequency  from  business  written  by  a  small  group  of  producers  of  our 
personal and commercial lines of business. The underlying cause of this development was the result of a subset of risk where 
the loss ratio pegs used in our year end actuarial determination was low given the ultimate frequency that emerged.

During  the  year  ended  December  31,  2019,  the  Company  experienced  an  increase  in  prior  year  development  of  $5,169, 
primarily  in  our  non-standard  auto  business.  The  underlying  cause  of  this  development  was  higher  than  expected  claim 
frequency.

F-44

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

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 prior year development in 2021, 2020, and 2019 of $2,606, $5,443 and $5,169, respectively, 
represented  3.7%,  20.2%  and  13.9%  of  pretax  income  of  our  insurance  business  of  $69,857,  $26,948  and  $37,030  in  each 
year, and 3.1%, 12.4% and 18.7% of the opening net liability for losses and loss adjustment expenses of $83,945, $43,881 
and $27,615, as of January 1 of each year.

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.

Incurred and Paid Development

The  following  table  presents  information  about  incurred  and  paid  loss  development  and  average  claim  duration  as  of 
December 31, 2021, 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. In 2020 and 2021, timing effects related to the COVID 19 pandemic 
impacted claim activity and, consequently, the duration of paid claims relative to incurred losses. We believe these impacts 
are  temporary  and  do  not  reflect  a  long  term  fundamental  change  in  duration  or  the  relationship  between  paid  claims  and 
incurred losses.

Incurred Losses and Allocated Loss Adjustment Expenses, Net of Reinsurance

As of December 31, 2021

Accident 
Year

2016
(Unaudited)

2017
(Unaudited)

2018
(Unaudited)

2019
(Unaudited)

2020
(Unaudited)

2021

For the Years Ended December 31,

Total of IBNR 
Liabilities Plus 
Expected 
Development of 
Reported 
Claims

Cumulative 
Number of 
Reported 
Claims

2016

2017

2018

2019

2020
2021

$ 

84,178  $ 

87,290  $ 

87,993  $ 

88,615  $ 

89,629  $ 

89,981  $ 

103,306   

104,898   

105,601   

105,787   

106,446  $ 

129,352   

133,225   

133,158   

134,392  $ 

144,925   

149,166   

151,772  $ 

172,007   

Total $ 

169,706  $ 
250,300 
902,597 

39 

— 

17,195 

8,852 

30,661 
59,994 

257 

326 

399 

403 

330 
473

Cumulative Paid Losses and Allocated Loss Adjustment Expenses, Net of Reinsurance

Accident 
Year

2016
(Unaudited)

2017
(Unaudited)

2018
(Unaudited)

2019
(Unaudited)

2020
(Unaudited)

2021

2016

2017

2018

2019

2020
2021

62,989  $ 

84,185  $ 

86,531  $ 

88,482  $ 

88,976  $ 

89,474 

84,493   

102,620   

105,075   

105,852   

106,402 

105,740   

112,619   

114,490   

115,407 

122,348   

128,787   

132,747 

127,721   

Total $ 

129,832 
174,334 
748,196 
11 

All outstanding liabilities before 2016, net of reinsurance

Liabilities for loss and loss adjustment expenses, net of reinsurance

$ 

154,412 

F-45

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

Duration

The following table presents supplementary information about average historical claims duration as of December 31, 2021 
for short duration contracts:

Average Annual Percentage Payout of Incurred Claims by Age, Net of Reinsurance (Unaudited)

Years

Short duration

1

75.6%

2

10.3%

3

2.2%

4

1.2%

5

0.5%

6

0.6%

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

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, 2021

$ 

$ 

154,412 
576 
154,988 

165,129 
165,129 

320,117 
801 
10,785 
331,703 

(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 (Topic 944) that are not within the scope of Revenue for Contracts with Customers (Topic 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, 

2021

2020

2019

$ 

$ 

163,583  $ 
41,634 
35,562 
— 
17,784 
258,563  $ 

98,574  $ 
36,159 
22,697 
— 
6,127 
163,557  $ 

27,597 
36,076 
16,747 
1,267 
7,317 
89,004 

Service and Administrative Fees:

Service contract revenue
Motor club revenue
Vessel related revenue
Management fee income
Other

Revenue from contracts with customers

Service and Administrative Fees

F-46

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

Service fee revenue is recognized as the services are performed. These services include fulfillment, software development, 
and  claims  handling  for  our  customers.  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 probable. 

Administrative fee revenue includes the administration of premium associated with our producers and PORCs. In addition, 
we  also  earn  fee  revenue  from  debt  cancellation,  motor  club,  and  auto  and  consumer  goods  service  contracts.  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 Rule of 78's, modified Rule of 78's, pro 
rata,  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.

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 at December 31, 2021.

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.

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  the  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. 

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

Total

January 1, 2021

December 31, 2021

Beginning balance

Additions

Amortization

Ending balance

$ 

$ 

$ 

$ 

48,734  $ 
13,081 
61,815  $ 

94,717  $ 
38,831 
133,548  $ 

33,231  $ 
32,488 
65,719  $ 

348,391  $ 
16,969 
365,360  $ 

285,591  $ 
49,535 
335,126  $ 

163,583  $ 
41,634 
205,217  $ 

110,220 
19,424 
129,644 

470,399 
24,870 
495,269 

For the periods presented, no write-offs for unrecoverable deferred acquisition costs and deferred revenue were recognized.

F-47

 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

 (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:

Loans eligible for repurchase
Mortgage servicing rights
Right of use asset - Operating leases (1)
Income tax receivable
Furniture, fixtures and equipment, net
Prepaid expenses
Other

Total other assets

As of December 31,
2020
2021

$ 

$ 

36,732  $ 
29,833 
23,870 
19,824 
14,878 
10,722 
10,985 
146,844  $ 

70,593 
14,758 
27,291 
19,513 
15,798 
8,159 
5,922 
162,034 

(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:

Depreciation expense related to furniture, fixtures and equipment

$ 

3,621  $ 

3,257  $ 

2,753 

For the Year Ended December 31, 

2021

2020

2019

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 liability  (1)
Due to brokers
Commissions payable
Securities sold, not yet purchased
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,
2020
2021

$ 

$ 

149,816  $ 
36,732 
40,049 
29,396 
10,763 
20,412 
242 
19,126 
306,536  $ 

106,142 
70,593 
24,183 
32,914 
45,047 
18,678 
46,637 
18,671 
362,865 

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,
2020

2019

2021

Other investment income (1)
Gain (loss) on sale of businesses (2)
Management fee income
Other (3)

Total other revenue

(1)

See Note (6) Investments for the components of Other investment income.

$ 

$ 

64,580  $ 
(1,928)   
— 
10,755 
73,407  $ 

48,747  $ 
(4,428)   
— 
7,591 
51,910  $ 

45,985 
7,598 
1,267 
5,038 
59,888 

F-48

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

(2) 
(3) 

Relates to the impairment of Luxury. See Note (4) Dispositions and Assets and Liabilities Held for Sale.
Includes $10,384, $7,025, and $4,566 for the years ended December 31, 2021, 2020 and 2019, 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,
2020

2019

2021

General and administrative
Professional fees
Premium taxes
Mortgage origination expenses
Rent and related
Operating expenses from vessels
Loss on extinguishment of debt
Other

Total other expenses

(17) Stockholders’ Equity

Stock Repurchases

$ 

$ 

36,654  $ 
27,285 
20,196 
17,451 
17,009 
13,797 
— 
9,652 
142,044  $ 

22,295  $ 
20,711 
15,824 
14,603 
14,074 
13,210 
353 
8,078 
109,148  $ 

18,563 
20,820 
15,205 
12,200 
12,642 
9,781 
1,241 
9,292 
99,744 

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. The following table 
presents the Company’s stock repurchase activity and remaining authorization. 

Share repurchase plan

Remaining repurchase authorization

Warrants

For the Year Ended
December 31, 2021

Number of 
shares 
purchased

Weighted 
average price 
per share

528,662  $ 

5.45 

$ 

13,669 

In April 2021, warrants were exercised for 207,445 shares of Tiptree common stock. As of December 31, 2021, there were 
warrants for 2,021,506 shares of Tiptree common stock outstanding at an exercise price of $6.97.

Dividends

The Company declared cash dividends per share for the following periods presented below:

For the Year Ended December 31,
2020

2019

2021

First quarter 
Second quarter 
Third quarter
Fourth quarter(1)

Total cash dividends declared

(1)

See Note (24) Subsequent Events for when the dividend was declared. 

$ 

$ 

0.04  $ 
0.04 
0.04 
0.04 
0.16  $ 

0.04  $ 
0.04 
0.04 
0.04 
0.16  $ 

0.04 
0.04 
0.04 
0.04 
0.16 

Statutory Reporting and Insurance Company Subsidiaries Dividend Restrictions

The Company’s U.S. insurance subsidiaries prepare financial statements in accordance with Statutory Accounting Principles 

F-49

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

(SAP)  prescribed  or  permitted  by  the  insurance  departments  of  their  states  of  domicile.  Prescribed  SAP  includes  the 
Accounting Practices and Procedures Manual of the National Association of Insurance Commissioners (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, 2021 and December 31, 2020.

Combined statutory capital and surplus of the Company's insurance company subsidiaries

Required minimum statutory capital and surplus

As of December 31,
2020
2021

286,015  $ 

202,710 

75,750  $ 

64,950 

$ 

$ 

Under  the  National  Association  of  Insurance  Commissioners  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, 2021.

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,
2019
2020

2021

$ 

33,999  $ 

19,647  $ 

8,444 

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.  There  were  no  dividends  paid  to  the  Company  by  its  U.S.  domiciled 
insurance company subsidiaries for the years ended December 31, 2021 and 2020.

The  following  table  presents  the  combined  amount  available  for  ordinary  dividends  of  the  Company's  U.S.  domiciled 
insurance company subsidiaries for the following periods:

As of December 31,
2020
2021

Amount available for ordinary dividends of the Company's insurance company subsidiaries

$ 

18,519  $ 

13,418 

At December 31, 2021, the maximum amount of dividends that our U.S. domiciled regulated insurance company subsidiaries 
could pay under applicable laws and regulations without regulatory approval was approximately $18,519. 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.

(18) Accumulated Other Comprehensive Income (Loss)

The following table presents the activity of AFS securities in accumulated other comprehensive income (loss) (AOCI), net of 
tax, for the following periods:

F-50

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

Amount 
attributable to non-
controlling 
interests

Total AOCI to 
Tiptree Inc.

Total AOCI

Balance at December 31, 2018

Other comprehensive income (losses) before reclassifications
Amounts reclassified from AOCI
OCI
Adoption of accounting standard (1)

Balance at December 31, 2019

Other comprehensive income (losses) before reclassifications
Amounts reclassified from AOCI
OCI
Adoption of accounting standard (1)

Balance at December 31, 2020

Other comprehensive income (losses) before reclassifications
Amounts reclassified from AOCI

OCI

Balance at December 31, 2021

$ 

$ 

$ 

$ 

(2,069)  $ 
4,911 
(1,032) 
3,879 
(99) 
1,711  $ 
4,364 
(415) 
3,949 
42 
5,702  $ 
(7,889) 
(499) 
(8,388) 
(2,686)  $ 

11  $ 
(24) 
— 
(24) 
— 
(13)  $ 
(15) 

(15) 
— 
(28)  $ 
29 
— 
29 
1  $ 

(2,058) 
4,887 
(1,032) 
3,855 
(99) 
1,698 
4,349 
(415) 
3,934 
42 
5,674 
(7,860) 
(499) 
(8,359) 
(2,685) 

(1) 

Amounts reclassified to retained earnings due to adoption of ASU 2016-13. See Note (2) Summary of Significant Accounting Policies.

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,
2020

2021

2019

$ 

$ 

638  $ 

528  $ 

1,312 

(139) 
499  $ 

(113) 
415  $ 

(280) 
1,032 

Affected line item in consolidated 
statements of operations
Net realized and unrealized gains (losses)

Provision for income tax

Components of AOCI
Unrealized gains (losses) on available 
for sale securities
Related tax (expense) benefit

Net of tax

(19) Stock Based Compensation

Equity Plans

2017 Omnibus Incentive Plan
The Company adopted the Tiptree 2017 Omnibus Incentive Plan (2017 Equity Plan) on June 6, 2017, which permits the grant 
of  restricted  stock  units  (RSUs),  stock,  and  stock  options  up  to  a  maximum  of  6,100,000  shares  of  common  stock.  The 
general purpose of the 2017 Equity Plan is to attract, motivate and retain selected employees and directors for the Company 
and its subsidiaries, to provide them with incentives and rewards for performance and to better align their interests with the 
interests of the Company’s stockholders. Unless otherwise extended, the 2017 Equity Plan terminates automatically on June 
6,  2027.  The  table  below  summarizes  changes  to  the  issuances  under  the  Company’s  2017  Equity  Plan  for  the  periods 
indicated,  excluding  awards  granted  under  the  Company’s  subsidiary  incentive  plans  that  are  exchangeable  for  Tiptree 
common stock:

F-51

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

2017 Equity Plan
Available for issuance as of December 31, 2018

RSU and option awards granted
Forfeited 
Exchanged for vested subsidiary awards

Available for issuance as of December 31, 2019

RSU, stock and option awards granted

Available for issuance as of December 31, 2020

RSU, stock and option awards granted
PRSU awards vested
Exchanged for vested subsidiary awards

Available for issuance as of December 31, 2021

Number of 
shares (1)

5,474,214 
(702,264) 
8,318 
(14,405) 
4,765,863 
(977,446) 
3,788,417 
(61,713) 
(215,583) 
(1,166,307) 
2,344,814 

(1)

Excludes awards granted under the Company’s subsidiary incentive plans that are exchangeable for Tiptree common stock.

Restricted Stock Units and Stock Awards

Tiptree Corporate Incentive Plans

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  with  respect  to  one-third  of  Tiptree  shares  granted  on  each  of  the  first,  second  and 
third year anniversaries of the date of the grant, and expensed using the straight-line method over the requisite service period.

Stock Awards - Directors’ Compensation

The Company values the stock awards at their issuance-date fair value as measured by Tiptree’s common stock price. Upon 
issuance, the awards are deemed to be granted and immediately vested. 

The following table presents changes to the issuances of RSUs and stock awards under the 2017 Equity Plan for the periods 
indicated:

Unvested units as of December 31, 2018

Granted
Vested
Forfeited 

Unvested units as of December 31, 2019

Granted
Vested

Unvested units as of December 31, 2020

Granted
Vested

Unvested units as of December 31, 2021

Number of 
shares 
issuable

Weighted 
average grant 
date fair value
6.27 
6.25 
6.44 
6.10 
6.23 
7.04 
6.54 
6.52 
7.81 
6.62 
6.59 

676,630  $ 
476,449 
(186,152) 
(8,318) 
958,609  $ 
552,169 
(557,633) 
953,145  $ 
61,713 
(415,846) 
599,012  $ 

The following tables present the detail of the granted and vested RSUs and stock awards for the periods indicated:

Granted
Directors
Employees (1)

Total Granted

For the Year Ended December 31,
2020

2019

2021

Vested

For the Year Ended December 31,
2019
2020
2021

61,713 
— 
61,713 

82,912 
469,257 
552,169 

48,076  Directors
428,373  Employees
476,449 

Total Vested

Taxes
Exchanged

Net Vested

F-52

61,713 
354,133 
415,846 
(34,828) 
— 
381,018 

82,912 
474,721 
557,633 
(53,438)   

— 
504,195 

48,076 
138,076 
186,152 
(35,622) 
14,405 
164,935 

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

(1)

Includes  256,619  and  307,148  shares  that  vest  ratably  over  three  years  and  212,638  and  112,907  shares  that  cliff  vest  in  February  2023  and  2022  for  the  years  ended 
December 31, 2020 and 2019, respectively.

Tiptree Senior Management Incentive Plan

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. 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, 2021, 3,266,667 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  will  be  adjusted  down  for 
cumulative dividends paid by the Company since grant (e.g., the next share price target is $19.92 as adjusted for cumulative 
dividends paid to date). 

Tiptree Share Price Target
$20
$30
$45
$60

Number of PRSUs that Vest
466,667
700,000
933,333
1,166,667

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. As of December 31, 
2021, the Company does not have sufficient shares available in the 2017 Equity Plan to settle the PRSUs awarded; as such, 
the PRSUs are classified as liability awards and will be remeasured at each reporting date until the date of settlement, and 
expensed using the straight-line method over the requisite service period.

The fair value of the PRSUs are estimated on the date of grant and at each subsequent reporting date 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 is 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  is  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 remeasure the fair value of the PRSUs as of December 31, 2021, which 
were granted in 2021 and classified as liability awards.

Valuation Input 

For the Year Ended December 31, 2021

Historical volatility
Risk-free rate
Dividend yield
Cost of equity
Expected term (years)

Subsidiary Incentive Plans

Assumption
37.69%
1.48%
1.18%
10.45%
7

Average
35.51%
1.41%
1.32%
10.07%
9

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.  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). Following the service period, such vested awards may be exchanged 

F-53

TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

at fair market value, at the option of the holder, for Tiptree common stock under the 2017 Equity Plan. The service period for 
certain grants has been achieved and those vested subsidiary awards are currently eligible for exchange. The Company has 
the option, but not the obligation to settle the exchange right in cash. 

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, 2018

Granted
Vested
Performance assumption adjustment
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, 2021

Grant date 
fair value of 
equity shares 
issuable

$ 

$ 

$ 

$ 

8,710 
— 
(4,991) 
560 
4,279 
1,108 
(4,237) 
3,155 
4,305 
1,278 
(3,472) 
123 
2,234 

The net vested balance of subsidiary awards eligible for exchange as of December 31, 2021 translates to 1,423,604 shares of 
Tiptree common stock.

Stock Option Awards

Tiptree Corporate Incentive Plans

Option awards have been 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. The 
market requirement is the Company's 20-day volume weighted average per share trading price plus actual cash dividends paid 
following issuance of the option that exceeds the book value on the option grant date. If the service condition is met, the full 
amount of the compensation expense will be recognized over the appropriate vesting period whether the market requirement 
is met or not. The options granted after 2017 include a retirement provision and are amortized over the lesser of the service 
condition or expected retirement date. There were no options granted during the year ended December 31, 2021. Book value 
targets for grants in 2020, 2019, 2018, 2017 and 2016 are $11.52, $10.79, $9.97, $10.14 and $8.96, respectively. 

During the year ended December 31, 2021, book value targets for all outstanding options were achieved. 

The  fair  value  option  grants  are  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  stock  prices  of  the  Company,  which  assumes  that  the 
market requirement is achieved. Historical volatility was computed based on historical daily returns of the Company’s stock 
between  the  grant  date  and  July  1,  2013,  the  date  of  the  business  combination  through  which  Tiptree  became  a  public 
company. The valuation is 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 grant date. The current quarterly dividend rates in effect as of the 
date of the grant are used to calculate a spot dividend yield as of the date of grant for use in the model. 

F-54

 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

There were no stock option awards granted in 2021. The following table presents the assumptions used to estimate the fair 
values of the stock options granted in 2020.

Valuation Input (1)

For the Year Ended December 31, 2020

Historical volatility
Risk-free rate
Dividend yield
Expected term (years)
(1)      Not applicable for the year ended December 31, 2021 as there were no new grants during the period.

Assumption
27.60%
1.51%
2.20%

Average
N/A
N/A
N/A
7.0

The following table presents the Company's stock option activity for the current period: 

Balance, December 31, 2020

Balance, December 31, 2021

Weighted 
average 
exercise price 
(in dollars per 
stock option)

Options 
outstanding

1,715,619  $ 

6.49  $ 

Weighted 
average grant 
date value (in 
dollars per 
stock option)
2.29 

Options 
exercisable

— 

1,715,619  $ 

6.49  $ 

2.29 

712,542 

Weighted  average  remaining  contractual  term  at  December  31, 
2021 (in years)

6.1

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,
2020

2019

2021

Employee compensation and benefits (1)
Director compensation
Income tax benefit

Net stock based compensation expense

$ 

$ 

10,665  $ 
465 
(2,338) 
8,792  $ 

7,571  $ 
546 
(1,705) 
6,412  $ 

6,062 
301 
(1,374) 
4,989 

(1)  Includes $6,609 related to liability awards recorded in other liabilities as of December 31, 2021.

Additional information on total non-vested stock based compensation is as follows:

As of December 31, 2021

Stock options
$ 

231  $ 
1.03

Restricted 
stock awards 
and RSUs

Performance 
Restricted 
Stock Units

2,143  $ 

0.64

18,491 
1.14

Unrecognized compensation cost related to non-vested awards
Weighted - average recognition period (in years)

F-55

 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

(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, 
2020

2019

2021

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

$ 

$ 

1,393  $ 
1,330 
838 
3,561 

(26,273)  $ 
1,692 
221 
(24,360) 

13,819 
4,435 
(524) 
17,730 
21,291  $ 

10,415 
697 
(379) 
10,733 
(13,627)  $ 

991 
386 
825 
2,202 

6,502 
335 
(22) 
6,815 
9,017 

On March 27, 2020, the Coronavirus Aid, Relief, and Economic Security Act (“CARES Act”) was enacted, implementing 
numerous changes to tax law including temporary changes regarding the prior and future utilization of net operating losses. 
During the year ended December 31, 2020, the Company recorded a $7,293 tax benefit related to the ability to carryback net 
operating losses to prior periods under the CARES Act, resulting in a decrease of our deferred tax asset of $16,795 and an 
increase to our current receivable of $24,088. The Company continues to assess the potential tax impacts of this legislation on 
its financial position and results of operations.

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 CARES Act refund claims
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, 

2021
65,342 

$ 

2020
(38,852) 

$ 

2019
29,139 

$ 

 21.0 %

 21.0 %

 21.0 %

13,721 
4,550 
4,518 
— 
(541) 
(1,642) 
154 
531 
21,291 

(8,159) 
1,929 
769 
(7,293) 
(938) 
(676) 
330 
411 
(13,627) 

$ 

$ 

6,119 
549 
105 
— 
440 
(398) 
1,524 
678 
9,017 

$ 

Effective tax rate

 32.6 %

 35.1 %

 31.0 %

For the year ended December 31, 2021, the Company’s effective tax rate on income 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 state taxes and non-deductible compensation, partially offset by the effect of stock based compensation.

For the year ended December 31, 2020, the Company’s effective tax rate on income from was equal to 35.1%. The effective 
tax rate for the year ended December 31, 2020 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.

F-56

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

For the year ended December 31, 2019, the Company’s effective tax rate on losses from was equal to 31.0%. The effective 
tax rate for the year ended December 31, 2019 is higher than the U.S. statutory income tax rate of 21.0% primarily due to the 
return-to-provision, as well as ongoing state and foreign taxes.

The table below presents the components of the Company’s net deferred tax assets and liabilities as of the respective balance 
sheet dates:

Deferred tax assets:

Net operating loss carryforwards
Unrealized losses
Accrued expenses
Unearned premiums
Deferred revenue
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
Intangibles

Total deferred tax liabilities

Net deferred tax liability  (1)

As of December 31,
2020
2021

$ 

$ 

39,047  $ 
23,419 
4,434 
39,221 
8,706 
10,475 
125,302 
(8,563) 
116,739 

2,467 
17,012 
7,819 
84,079 
34,700 
11,370 
157,447 
40,708  $ 

26,404 
25,527 
3,560 
25,626 
7,042 
7,091 
95,250 
(6,871) 
88,379 

2,697 
17,968 
4,057 
47,061 
30,977 
10,741 
113,501 
25,122 

(1)   Includes $659 and $939 classified as held for sale as of December 31, 2021 and December 31, 2020, respectively. See Note (4) Dispositions and Assets and Liabilities Held for Sale.

As of January 2016, Tiptree has established a U.S. federal consolidated income tax group and as such files on a consolidated 
basis,  with  certain  exceptions  such  as  a  Fortegra  life  insurance  company  and  Luxury.  Tiptree  consolidated,  and  certain 
subsidiaries  on  a  separate  basis,  file  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-57

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

As of December 31, 2021, the Company had total U.S. Federal net operating loss carryforwards (NOLs) of $117,098. 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, 
2021

$ 

$ 

— 
— 
359 
— 
— 
— 
— 
— 
— 
491 
39,862 
907 
— 
— 
— 
42,869 
32,610 
117,098 

In addition to the U.S. Federal NOL, Tiptree and its subsidiaries have NOLs in various state jurisdictions totaling $14,399 as 
of December 31, 2021. Valuation allowances of $8,563 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, 2021, the consolidated valuation allowance for Tiptree was $8,563. In 2021, the Company recorded a net 
increase in its valuation allowances equal to $1,692, compared to a net increase in its valuation allowance of $1,910 in 2020.

As  of  December  31,  2021  and  2020,  the  Company  had  no  material  unrecognized  tax  benefits  or  accrued  interest  and 
penalties. Federal tax years 2017 and onward are open for examination as of December 31, 2021.

F-58

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

(21) Commitments and Contingencies

Operating Leases

All leases are office space leases and are classified as operating leases that expire through 2031. 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, 
2021:

Right of use asset - Operating leases

Operating lease liability

Weighted-average remaining lease term (years)

Weighted-average discount rate (1)

As of
December 31,
2021
23,870 

$ 

$ 

29,396 

6.8

 7.5 %

(1) 

Discount rate was determined by applying available market rates to lease obligations based upon their term.

As of December 31, 2021, the approximate aggregate minimum future lease payments required for our lease liability over the 
remaining lease periods are as follows:

2022
2023
2024
2025
2026
2027 and thereafter

Total minimum payments
Less: liabilities held for sale
Less: present value adjustment

Total 

As of

December 31,
2021

$ 

$ 

8,266 
7,495 
6,513 
5,785 
5,350 
13,468 
46,877 
829 
16,652 
29,396 

The following table presents rent expense for the Company’s office leases recorded on the consolidated statements of 
operations for the following periods:

Rent expense for office leases (1)
(1)  

Includes lease expense of $609 and $509 for the year ended December 31, 2021 and 2020, respectively, for assets held for sale.

For the Year Ended December 31,

2021

2020

2019

$ 

8,924  $ 

7,374  $ 

8,612 

Litigation

The Company is a defendant in Mullins v. Southern Financial Life Insurance Co., which was filed in February 2006, in the 
Pike County Circuit Court, in the Commonwealth of Kentucky. A class was certified in June 2010. At issue is whether the 
coverage  period  of  certain  credit  disability  and  life  insurance  policies  issued  in  Kentucky  were  limited  by  the  term  of  the 
associated  loan.  The  action  alleges  violations  of  the  Kentucky  Consumer  Protection  Act  and  certain  insurance  statutes, 
common law fraud and breach of contract and the covenant of good faith and fair dealing. Plaintiffs seek compensatory and 
punitive damages, attorneys’ fees and interest. 

In July 2021, the court entered an Order granting Plaintiffs’ Motion for Partial Summary Judgment as to certain disability 
policies,  ruling  that  if  a  class  member  became  disabled  during  the  coverage  period,  benefits  could  extend  beyond  the 
coverage  period  until  the  associated  loan  was  paid  off.  The  Company  intends  to  challenge  the  court’s  ruling.  In  February 

F-59

 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

2022,  a  hearing  was  held  on  competing  motions  for  partial  summary  judgment  on  the  principal  claims.  A  hearing  for 
Plaintiffs’ Motion for Sanctions for Spoliation of Evidence is scheduled for June 9, 2022. The court has not yet ruled on the 
pending motions. No additional hearings are scheduled and a trial date has not been set.   

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:

For the Year Ended December 31, 
2019
2020
2021

$ 

44,051  $ 

(25,225)  $ 

20,122 

Net income (loss) attributable to non-controlling interests
Net income allocated to participating securities
Net income (loss) attributable to Tiptree Inc. common shares - basic

5,919 
703 
37,429 

3,933 
— 
(29,158) 

1,761 
472 
17,889 

Effect of Dilutive Securities:
Securities of subsidiaries
Adjustments to income relating to exchangeable interests, net of tax
Net income (loss) attributable to Tiptree Inc. common shares - diluted

(780)   
9 
36,658  $ 

— 
— 
(29,158)  $ 

(723) 
— 
17,166 

$ 

Weighted average number of shares of common stock outstanding - basic

  33,223,792 

  33,859,775 

  34,578,292 

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

464,464 
  33,688,256 

— 
  33,859,775 

— 
  34,578,292 

Basic net income (loss) attributable to common shares
Diluted net income (loss) attributable to common shares

$ 
$ 

1.13  $ 
1.09  $ 

(0.86)  $ 
(0.86)  $ 

0.52 
0.50 

(23) Related Party Transactions

Corvid  Peak  is  a  related  party  of  the  Company  because  Corvid  Peak  is  deemed  to  be  controlled  by  Michael  Barnes,  the 
Company’s Executive Chairman. The Company is invested in a fund managed by Corvid Peak (the “Corvid Peak Fund”) 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 Fund and IAA, the Company incurred $1,988, $2,792 and $1,006 of 
management and incentive fees for the years ended December 31, 2021, 2020 and 2019, respectively. Beginning January 1, 

F-60

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC. AND SUBSIDIARIES
Notes to Consolidated Financial Statements
December 31, 2021
(in thousands, except share data)

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.  As  of  January  1,  2022,  Tiptree’s  percentage  interest  was  21.95%  (including 
interests acquired from former Corvid Peak equity holders). For the year ended December 31, 2021, the Company recognized 
a $81 loss of allocated profit/loss interest that has been recorded in other revenue in the consolidated statements of operations.

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, 2021, 2020 and 2019 were 
not material.

Pursuant to a Partner Emeritus Agreement, Tiptree agreed to provide Mr. Inayatullah, a greater than 5% stockholder of the 
Company, office space and 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, 2021 and 2020 were not material.

(24) Subsequent Events

On  March  8,  2022,  the  Company’s  board  of  directors  declared  a  quarterly  cash  dividend  of  $0.04  per  share  to  holders  of 
common stock with a record date of March 21, 2022, and a payment date of March 28, 2022.

F-61

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, 2021. 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, 2021.

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, 2021 was effective using the COSO Framework.

The effectiveness of the Company’s internal control over financial reporting as of December 31, 2021 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, 2021, 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, 2021.

(c)  Changes in Internal Control over Financial Reporting

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 three months ended December 31, 2021 that have materially affected, or 
are reasonably likely to materially affect, our internal control over financial reporting.

Item 9B. Other Information

None.

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 2022 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 2022 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 2022 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 2022 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 2022 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 2022 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 2022 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 2022 Annual Meeting of Stockholders. 

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, 2021 and 2020
Consolidated Statements of Operations for the years ended December 31, 2021, 2020 and 2019
Consolidated Statements of Comprehensive Income (Loss) for the years ended December 31, 2021, 
2020 and 2019
Consolidated  Statements  of  Changes  in  Stockholders’  Equity  for  the  years  ended  December  31, 
2021, 2020 and 2019
Consolidated Statements of Cash Flows for the years ended December 31, 2021, 2020 and 2019

Notes to Consolidated Financial Statements 

(a)(2) Financial Statement Schedules

Page
F- 1
F- 2

F- 3

F- 4
F- 5

F- 6

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.”

The financial statements of Invesque Inc. required by Rule 3-09 of Regulation S-X will be provided as Exhibit 99.1 to this 
report. 

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

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).

Fourth Amended and Restated Bylaws of the Registrant (previously filed as Exhibit 3.2 to the Registrant’s 
Current Report on Form 8-K (File No. 001-33549), filed on January 4, 2017 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.

Form of Warrant to Purchase Common Stock (Expiring June 30, 2022) (previously filed as Exhibit 10.3 to the 
Registrant’s Current Report on Form 8-K (File No. 001-33549), filed on April 10, 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).

3.1

3.2

3.3

4.1

4.2

4.3

10.1

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).**

 
 
Exhibit 
No.

Description

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 Restricted Stock Unit Agreement under the Registrant’s 2017 Omnibus Incentive Plan (annual vesting) 
(previously filed as Exhibit 10.4 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 Restricted Stock Unit Agreement under the Registrant’s 2017 Omnibus Incentive Plan (cliff vesting) 
(previously filed as Exhibit 10.5 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 (for 2020 
and beyond) (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) .**

Form of Restricted Stock Unit Agreement under the Registrant’s 2017 Omnibus Incentive Plan (for 2020 and 
beyond) (annual vesting) (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 (for 2020 and 
beyond) (cliff vesting) (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 Performance Restricted Stock Unit Agreement (previously filed as Exhibit 10.1 to the Registrant’s 
Current Report on Form 8-K (File No. 001-33549), filed on August 4, 2021 and herein incorporated by 
reference).**

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).

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).

Credit Agreement, dated as of February 21, 2020, between Tiptree Inc., Tiptree Operating Company, LLC, 
Fortress Credit Corp. as Administrative Agent, Collateral Agent and Lead Arranger, and the lenders party 
thereto. (previously filed as Exhibit 10.1 to Form 8-K (File No. 001-33549), filed February 21, 2020 and herein 
incorporated by reference).

Amended and Restated Credit Agreement, dated as of August 4, 2020 by and among Fortegra Financial 
Corporation (“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 (previously filed as Exhibit 10.1 to Form 8-K (File No. 
001-33549), filed August 5, 2020 and herein incorporated by reference).

Credit Agreement, dated as of October 16, 2020 by and among South Bay Financial 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 Form 8-K (File No. 001-33549), filed October 21, 
2020 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 to Partner Emeritus Agreement, effective January 1, 2022, by and between Tiptree Inc. and Arif 
Inayatullah (previously filed as Exhibit 10.1 to the Registrant’s Current Report on Form 8-K (File No. 
001-33549), filed on January 3, 2022 and herein incorporated by reference).

Securities Purchase Agreement between and among Tiptree Inc., The Fortegra Group, Inc. and WP Falcon 
Aggregator, L.P. dated October 11, 2021 (previously filed as Exhibit 10.1 to the Registrant’s Current Report on 
Form 8-K (File No. 001-33549) filed on October 12, 2021 and herein incorporated by reference).

10.2

10.3

10.4

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

Exhibit 
No.

10.18

10.19

10.20

10.21

10.22

10.23

10.24

10.25

21.1

23.1

23.2

31.1

31.2

31.3

32.1

32.2

32.3
99.1
99.2

Description
Form of Warrant 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 October 12, 2021 and herein incorporated by reference).

Form of Investor 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 October 12, 2021 and herein 
incorporated by reference).

Form of Tiptree Additional Warrants to Purchase Common Stock (previously filed as Exhibit 10.4 to the 
Registrant’s Current Report on Form 8-K (File No. 001-33549) filed on October 12, 2021 and herein 
incorporated by reference).

Form of Certificate of Designation of Series A Preferred Stock (previously filed as Exhibit 10.5 to the 
Registrant’s Current Report on Form 8-K (File No. 001-33549) filed on October 12, 2021 and herein 
incorporated by reference).

Form of Stockholders Agreement between and among Tiptree Holdings LLC, The Fortegra Group Inc. and WP 
Falcon Aggregator, L.P. (previously filed as Exhibit 10.6 to Form 8-K (File No. 001-33549) filed on the 
Registrant’s Current Report on October 12, 2021 and herein incorporated by reference).

Form of 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 10.7 to the 
Registrant’s Current Report on Form 8-K (File No. 001-33549) filed on October 12, 2021 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).

Executive Employment Agreement by and among Tiptree Inc. and Randy Maultsby, dated as of July 14, 2021 
(previously filed as Exhibit 10.1 to the Registrant’s Current Report on Form 8-K (File No. 001-33549), filed on 
July 14, 2021 and herein incorporated by reference).**

Subsidiaries of the Registrant (filed herewith).

Consent of Independent Registered Public Accounting Firm (filed herewith).

Consent of KPMG LLP, Independent Auditors of Invesque Inc. (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).
Consolidated Financial Statements of Invesque Inc. as at December 31, 2021 and 2020 (filed herewith).
Consolidated Financial Statements of Invesque Inc. as at December 31, 2020 and 2019 (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*

Exhibit 
No.

Description

101.DEF XBRL Taxonomy Extension Definition Linkbase Document*

104

Cover page from Tiptree Inc.’s Annual Report on Form 10-K for the fiscal year ended December 31, 2021, 
formatted in iXBRL (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,  2021  and  December  31, 
2020, (ii) the Consolidated Statements of Operations (audited) for the years ended December 31, 2021, 2020 and 2019, (iii) 
the Consolidated Statements of Comprehensive Income (Loss) (audited) for the years ended December 31, 2021, 2020 and 
2019, (iv) the Consolidated Statements of Changes in Stockholders’ Equity (audited) for the years ended December 31, 2021, 
2020 and 2019, (v) the Consolidated Statements of Cash Flows (audited) for the years ended December 31, 2021, 2020 and 
2019 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. 

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:  March 11, 2022

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/ Sandra Bell
Sandra Bell

/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                               

March 11, 2022

(Principal Executive Officer)

Chief Financial Officer         

(Principal Financial Officer and
Principal Accounting Officer)

March 11, 2022

  Executive Chairman and Director

March 11, 2022

President and Director

March 11, 2022

Director

Director

Director

Director

March 11, 2022

March 11, 2022

March 11, 2022

March 11, 2022

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
Schedule II — Condensed Financial Information of Registrant

TIPTREE INC.
PARENT COMPANY ONLY CONDENSED STATEMENTS OF INCOME

(All amounts in thousands)

Revenues

Interest income
Other revenue
Total revenues

Expenses

Employee compensation and benefits
Interest expense
Professional fees
Rent and facilities
General and administrative
Depreciation and amortization
Loss on extinguishment of debt
Other expenses

Total expenses

For the Year Ended December 31,
2020

2019

2021

$ 

259  $ 
67 
326 

223  $ 
232 
455 

28,060 
— 
6,656 
1,993 
1,254 
805 
— 
1,305 
40,073 

15,195 
4,681 
4,476 
2,094 
1,259 
807 
353 
1,513 
30,378 

— 
— 
— 

— 
— 
— 
— 
— 
— 
— 
3 
3 

Equity in earnings (losses) of subsidiaries, net of tax (1)

73,164 

(24,855) 

18,364 

Income (loss) before taxes

Less: provision (benefit) for income taxes

Net income (loss) attributable to Tiptree Inc. common stockholders

$ 

(1)      Eliminated in consolidation.

33,417 
(4,715) 
38,132  $ 

(54,778) 
(25,620) 
(29,158)  $ 

18,361 
— 
18,361 

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC.
PARENT COMPANY ONLY CONDENSED BALANCE SHEETS

(All amounts in thousands, except share data)

Assets

Investment in subsidiaries (1)
Cash and cash equivalents
Notes and accounts receivable, net
Intercompany receivables, net (1)
Income taxes receivable
Deferred tax assets
Other assets
Total assets

Liabilities and Stockholders’ Equity
Liabilities

Deferred tax liabilities
Operating lease liability
Intercompany payables, net (1)
Accrued expenses
Other liabilities
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, 34,124,153 and 32,682,462 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.

As of December 31,
2020
2021

370,632  $ 
2,456 
2,897 
— 
15,968 
20,830 
14,100 
426,883  $ 

—  $ 

11,319 
7,136 
18,731 
6,743 
43,929  $ 

337,951 
712 
2,622 
— 
15,590 
44,161 
15,332 
416,368 

23,889 
12,241 
9,861 
7,490 
6,743 
60,224 

—  $ 

— 

34 
317,459 
(2,685) 
68,146 
382,954 
426,883  $ 

33 
315,014 
5,674 
35,423 
356,144 
416,368 

$ 

$ 

$ 

$ 

$ 

$ 

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
TIPTREE INC.
PARENT COMPANY ONLY CONDENSED 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)
Depreciation expense
Deferred provision (benefit) for income taxes
Non-cash lease expense
Non-cash compensation expense
Amortization of deferred financing costs
Changes in operating assets and liabilities

Net changes in other operating assets and liabilities

Net cash provided by (used in) operating activities

Investing Activities:

Proceeds from the sale of businesses
Proceeds from notes receivable
Issuance of notes receivable
Asset acquisitions due to merger with Operating Co.

Net cash flows provided by (used in) provided by investing activities

Financing Activities:
Distributions from subsidiaries (1)
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,
2020

2019

2021

$ 

38,132  $ 

(29,158)  $ 

18,361 

(73,164) 
805 
(528) 
1,843 
8,580 
— 

5,412 
(18,920) 

125 
169 
(432) 
— 
(138) 

24,855 
807 
(15,815) 
1,660 
3,110 
172 

1,264 
(13,105) 

— 
— 
— 
488 
488 

30,996 
(5,409) 
(2,882) 
(1,458) 
(445) 
20,802 
1,744 
712 
2,456  $ 

35,092 
(5,565) 
(13,889) 
(2,034) 
(362) 
13,242 
625 
87 
712  $ 

(18,364) 
— 
— 
— 
— 
— 

(583) 
(586) 

— 
— 
— 
— 
— 

14,587 
(5,502) 
(9,085) 
— 
— 
— 
(586) 
673 
87 

61  $ 

(166)  $ 

2,168 

$ 

$ 

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, a secured corporate credit 
agreement of a subsidiary of Tiptree restricts that subsidiary’s ability to pay or make any dividend or 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  condensed  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, 2021. 

For the period ending December 31, 2019, the Company was a holding company without any operations of its own. On July 17, 
2020, Operating Company merged into Tiptree, with Tiptree as the surviving entity (the Reorganization). In connection with the 
Reorganization,  Operating  Company  contributed  substantially  all  of  its  assets  to  Caroline  Holdings  LLC,  a  wholly  owned 
subsidiary  of  Operating  Company,  which  was  renamed  Tiptree  Holdings  LLC.  Prior  to  the  Reorganization,  the  Company  was 

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
  
allocated itemized expenses of $2,000 related to operating as a public company from Operating Company for the six months ended 
June 30, 2020.

These condensed 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  normally  included  in  financial  statements  prepared  in  accordance  with  GAAP  have  been  condensed  or  omitted.  The 
accompanying  condensed  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  $30,996,  $35,092  and  $14,587  for  the  years  ended  December  31,  2021,  2020  and  2019, 
respectively.

BR88822Q-0422-AR