Quarterlytics / Consumer Cyclical / Auto - Dealerships / Kingsway Financial Services Inc

Kingsway Financial Services Inc

kfs · NYSE Consumer Cyclical
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Ticker kfs
Exchange NYSE
Sector Consumer Cyclical
Industry Auto - Dealerships
Employees 201-500
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FY2022 Annual Report · Kingsway Financial Services Inc
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UNITED STATES  
SECURITIES AND EXCHANGE COMMISSION 
WASHINGTON, D.C. 20549   
FORM 10-K 

☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 

For the fiscal year ended December 31, 2022 
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 001-15204   
Kingsway Financial Services Inc. 
(Exact name of registrant as specified in its charter)  

Delaware 
(State or other jurisdiction of 
incorporation or organization) 

10 S. Riverside Plaza, Suite 1520 
Chicago, IL  
(Address of principal executive 
offices) 

85-1792291 

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

60606 

(Zip Code) 

1-312-766-2138 
(Registrant’s telephone number, including area code)  

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

Title of Each Class 
Common Stock, no par value 

Trading Symbol 
KFS 

Name of Each Exchange on Which 
Registered 
New York Stock Exchange 

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   ☒ 

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   ☒ 

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   ☒     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   ☒     No   ☐ 

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or 
an emerging growth company. See 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 ☐  Accelerated filer ☐  Non-accelerated filer ☒ 

Smaller Reporting Company☒ 

Emerging Growth Company ☐ 

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any 
new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐ 

Indicate by check mark whether the registrant has filed a report on and attestation to its management’s assessment of the effectiveness of its internal 
control over financial reporting under Section 404(b) of the Sarbanes-Oxley Act (15 U.S.C. 7262(b)) by the registered public accounting firm that 
prepared or issued its audit report. ☐ 

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

Indicate by check mark whether any of those error corrections are restatements that required a recovery analysis of incentive-based compensation 
received by any of the registrant’s executive officers during the relevant recovery period pursuant to §240.10D-1(b). ☐ 

Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Exchange Act).    Yes   ☐     No   ☒ 

As of June 30, 2022, the aggregate market value of the registrant’s voting common stock held by non-affiliates of registrant was $48,712,518 based 
upon the closing sale price of the common stock as reported by the New York Stock Exchange. Solely for purposes of this calculation, all executive 
officers and directors of the registrant are considered affiliates. 

The number of shares, including restricted common shares, of the Registrant’s Common Stock outstanding as of March 8, 2023 was 25,045,024. 

Part III of this Form 10-K is incorporated by reference to certain sections of the Proxy Statement for the 2022 Annual Meeting of Shareholders, which 
will be filed with the Securities and Exchange Commission no later than 120 days after the end of our fiscal year ended December 31, 2022. 

DOCUMENTS INCORPORATED BY REFERENCE 

  
KINGSWAY FINANCIAL SERVICES INC. 

Table of Contents 

Caution Regarding Forward-Looking Statements 

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 

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 

Item 14. Principal Accountant Fees and Services 

PART IV 

Item 15. Exhibits and Financial Statement Schedules 

Item 16. Form 10-K Summary 

EXHIBIT INDEX 

SIGNATURES 

i 

ii 

1 

1 

8 

17 

17 

17 

17 

18 

18 

18 

19 

41 

42 

104 

104 

105 

105 

106 

106 

106 

106 

106 

106 

107 

107 

112 

112 

115 

 
 
 
KINGSWAY FINANCIAL SERVICES INC. 

Caution Regarding Forward-Looking Statements 

This 2022 Annual Report on Form 10-K (the “2022 Annual Report”), including the accompanying consolidated financial statements of 
Kingsway Financial Services Inc. (“Kingsway”) and its subsidiaries (individually and collectively referred to herein as the “Company”) 
and the notes thereto appearing in Item 8 herein (the “Consolidated Financial Statements”), Management’s Discussion and Analysis of 
Financial Condition and Results of Operations appearing in Item 7 herein (“MD&A”), and the other Exhibits and Financial Statement 
Schedules filed as a part hereof or incorporated by reference herein may contain or incorporate by reference information that includes 
or is based on forward-looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the 
Securities Exchange Act of 1934. 

Forward-looking statements relate to future events or future performance and reflect Kingsway management’s current beliefs, based on 
information  currently  available.  The  words  “anticipate,”  “expect,”  “believe,”  “may,”  “should,”  “estimate,”  “project,”  “outlook,” 
“forecast” and variations or similar words and expressions are used to identify such forward looking information, but these words are 
not the exclusive means of identifying forward-looking statements. Specifically, statements about (i) the Company’s ability to preserve 
and use its net operating losses; (ii) the Company’s expected liquidity; and (iii) the potential impact of volatile investment markets and 
other economic conditions on the Company’s investment portfolio, among others, are forward-looking, and the Company may also make 
forward-looking statements about, among other things: 

• 

• 

• 

• 

• 

• 

its results of operations and financial condition (including, among other things, net and operating income, investment income and 
performance, return on equity and expected current returns); 

changes in industry trends and significant industry developments, especially as it relates to the automotive service contract and 
business services industries; 

the impact of certain guarantees and indemnities made by the Company; 

its ability to complete and integrate current or future acquisitions successfully; 

its ability execute its strategic initiatives successfully; and 

the potential impact of the uncertainties related to actual or potential changes in international, national, regional and local economic, 
business and financial conditions on the short and long-term economic effects on the Company’s business. 

For a discussion of some of the factors that could cause actual results to differ, see Item 1A,”Risk Factors” and our disclosures under 
the heading “Significant Accounting Policies and Critical Estimates” in MD&A in this 2022 Annual Report. 

Except as expressly required by applicable securities laws, the Company disclaims any intention or obligation to update or revise any 
forward-looking statements, whether as a result of new information, future events or otherwise, that might arise subsequent to the date 
of this 2022 Annual Report. 

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KINGSWAY FINANCIAL SERVICES INC. 

Part I 

Item 1. BUSINESS 

In  this  report,  the  terms  “Kingsway,”  the  “Company,”  “we,”  “us”  or  “our”  mean  Kingsway  Financial  Services  Inc.  and  all  entities 
included in our Consolidated Financial Statements. 

Kingsway Financial Services Inc. was incorporated under the Business Corporations Act (Ontario) on September 19, 1989. Effective 
December  31,  2018,  the  Company  changed  its  jurisdiction  of  incorporation  from  the  province  of  Ontario,  Canada,  to  the  State  of 
Delaware. The Company’s registered office is located at 10 S. Riverside Plaza, Suite 1520, Chicago, Illinois 60606.  The common shares 
of Kingsway are listed on the NYSE under the trading symbol “KFS.” 

Kingsway is a holding company with operating subsidiaries located in the United States. The Company owns or controls subsidiaries 
primarily in the extended warranty and business services industries. Kingsway conducts its business through two reportable segments 
- Extended Warranty and Kingsway Search Xcelerator - that conduct their business and distribute their products and services in  the 
United States. 

Prior  to  the  fourth  quarter  of  2022,  the  Company  conducted  its  business  through  a  third  reportable  segment,  Leased  Real  Estate, 
which included the following subsidiaries of the Company: CMC Industries, Inc. (“CMC”) and VA Lafayette, LLC (“VA Lafayette”): 

•  CMC owned, through an indirect wholly owned subsidiary (the “Property Owner”), a parcel of real property consisting of 
approximately 192 acres located in the State of Texas (the “Real Property”), which is subject to a long-term triple net lease 
agreement. The Real Property is also subject to two mortgages.  On December 22, 2022, the Company announced a definitive 
agreement  for  the  sale  of  the  Real  Property,  for  gross  cash  proceeds  of  $44.5  million and  the  assumption  of  the  two 
mortgages.  On December 29, 2022, the sale was completed.  

•  VA Lafayette owns real property consisting of approximately 6.5 acres and a 29,224 square foot single-tenant medical office 
building located in the State of Louisiana (the “LA Real Property”). The LA Real Property serves as a medical and dental clinic 
for  the  Department  of  Veteran  Affairs  and  is  subject  to  a  long-term lease.  The  LA  Real  Property  is  also  subject  to  a 
mortgage (the “LA Mortgage”).  During the fourth quarter, the Company began executing a plan to sell VA Lafayette, and as 
a result, VA Lafayette is reported as held for sale at December 31, 2022.  

•  Both CMC and VA Lafayette have been classified as discontinued operations and the results of their operations are reported 
separately for all periods presented. All segmented information has been restated to exclude the Leased Real Estate segment 
for all periods presented.  

Financial information about Kingsway’s reportable business segments for the years ended December 31, 2022 and December 31, 2021 
is contained in the following sections of this 2022 Annual Report: (i) Note 22, “Segmented Information,” to the Consolidated Financial 
Statements; and (ii) “Results of Continuing Operations” section of MD&A. 

All of the dollar amounts in this 2022 Annual Report are expressed in U.S. dollars. 

GENERAL DEVELOPMENT OF BUSINESS 

Acquisition of CSuite Financial Partners, LLC 

On  November  1,  2022,  the  Company  acquired  100%  of  the  outstanding  equity  interests  of  CSuite Financial  Partners,  LLC 
(“CSuite”).   CSuite, based  in  Manhattan  Beach,  California,  is  a  national  financial  executive  services  firm  providing  financial 
management  leadership  to  companies  in  every  industry,  regardless  of  size,  throughout  the  United  States.  CSuite  is  included  in  the 
Kingsway Search Xcelerator segment. 

The  Company  acquired  CSuite  for  aggregate  cash  consideration  of  approximately  $8.5  million,  less  certain  escrowed  amounts  for 
purposes of indemnification claims and working capital adjustments. The Company will also pay additional contingent consideration, 
only to the extent earned, in an aggregate amount of up to $3.6 million, which is subject to certain conditions, including the successful 
achievement of certain financial metrics for CSuite during the three-year period commencing on the first full calendar month following 
the acquisition date.  Further information is contained in Note 4, “Acquisitions,” to the Consolidated Financial Statements. 

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KINGSWAY FINANCIAL SERVICES INC. 

The closing purchase price was paid with cash on hand; however, subsequent to the CSuite acquisition, on November 16, 2022, the 
Company  amended  its  October  1,  2021 loan  agreement with Avidbank  to  borrow  an  additional  $6.0  million in  the  form  of  a 
supplemental term loan (the “2022 Ravix Loan”). The 2022 Ravix Loan has a variable interest rate equal to the Prime Rate plus 0.75%. 
The 2022 Ravix Loan requires monthly principal and interest payments and the term loan matures on November 16, 2028. 

Acquisition of Secure Nursing Service, Inc. 

On November 18, 2022, the Company acquired substantially all of the assets and assumed certain specified liabilities of Secure Nursing 
Service, Inc.  (“SNS”).  SNS, based  in  Los Angeles,  California,  employs  highly  skilled, professional per diem  and  travel  Registered 
Nurses, Licensed Vocational Nurses, Certified Nurse Assistants and Allied Healthcare Professionals with multiple years of acute care 
hospital experience.  SNS places these healthcare professionals in both per diem assignments, and in short-term and long-term travel 
assignments in a variety of hospitals in southern California. SNS is included in the Kingsway Search Xcelerator segment. 

The  Company  acquired  SNS  for  aggregate  cash  consideration  of  $11.5  million,  less  certain  escrowed  amounts  for  purposes  of 
indemnification claims and working capital adjustments.  Further information is contained in Note 4, “Acquisitions,” to the Consolidated 
Financial Statements. 

The closing purchase price was financed with a combination of debt financing provided by Signature Bank and cash on hand. Secure 
Nursing Service LLC and Pegasus Acquirer LLC, subsidiaries of Kingsway, borrowed a total of $6.5 million, in the form of a term loan, 
and established a $1 million revolver (together, the “SNS Loan”) that was undrawn at close. The Loan has a variable interest rate equal 
to the Prime Rate plus 0.50%, with a floor of 5.00%. The SNS Loan requires monthly principal and interest payments, and the term loan 
matures on November 18, 2028. 

Disposal of Professional Warranty Service Corporation  

On July 29, 2022, Professional Warranty Services LLC (“PWS LLC”), a subsidiary of the Company entered into an Equity Purchase 
Agreement (the “PWSC Agreement”) with Professional Warranty Service Corporation (“PWSC”), an 80% majority-owned, indirect 
subsidiary of the Company, Tyler Gordy, the president of PWSC and a 20% owner of PWSC (“Gordy”) and PCF Insurance Services of 
the West, LLC (“Buyer”), pursuant to which PWS LLC and Gordy sold PWSC to Buyer.  

The purchase price paid  by Buyer  to  PWS  LLC and  Gordy  consisted of $51.2 million  in base purchase  price,  subject  to  customary 
adjustments for net working capital, and non-compensation related transaction expenses of approximately $1.7 million.   

To the extent the EBITDA of PWSC (as defined in the PWSC Agreement) for the one-year period following the sale transaction exceeds 
103% of the EBITDA at the closing of the sale transaction (the “Closing EBITDA”), PWS LLC and Gordy will also be entitled to 
receive an earnout payment in an amount equal to five times the EBITDA in excess of 103% of Closing EBITDA.  The Company does 
not have access to the information needed to reasonably estimate the potential earnout payment and accordingly any gain related to the 
earnout payment will be recorded in the period the consideration is determined to be realizable. Further information is contained in Note 
5, “Disposal and Discontinued Operations” to the Consolidated Financial Statements. 

Sale of CMC Real Property 

On December 22, 2022, TRT Leaseco, LLC (“TRT”), an indirect subsidiary of the Company, entered into a Purchase and Sale Agreement 
(the “Agreement”) with BNSF Dayton LLC (“Purchaser”), pursuant to which TRT agreed to sell to the Purchaser the Real Property. The 
Real Property was subject to two mortgages.  TRT is also the landlord under an existing railway lease over the Real Property.  An affiliate 
of the Purchaser is the current tenant under the existing railway lease. Under the terms of the Agreement, at the closing on December 29, 
2022, TRT assigned, and the Purchaser assumed, the rights and obligations of the landlord under the existing railway lease.   

The purchase price paid by the Purchaser at the closing consisted of $44.5 million in cash plus the assumption of the unpaid principal 
balance as of the closing of the two mortgages of approximately $170.7 million, netting cash proceeds of $21.4 million to Kingsway 
after taxes, fees and distribution to the minority shareholder.  Further information is contained in Note 5, “Disposal and Discontinued 
Operations” to the Consolidated Financial Statements. 

Asset Held for Sale 

During  the  fourth  quarter  of  2022,  the  Company’s  subsidiary VA  Lafayette  was  classified  as  held  for  sale.   Further  information  is 
contained in Note 5, “Disposal and Discontinued Operations” to the Consolidated Financial Statements.  VA Lafayette owns the LA 
Real Property, which is also subject to the LA Mortgage. 

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KINGSWAY FINANCIAL SERVICES INC. 

EXTENDED WARRANTY SEGMENT 

Extended Warranty includes the following subsidiaries of the Company (collectively, “Extended Warranty”): 

• 

IWS Acquisition Corporation (“IWS”) 

•  Geminus Holding Company, Inc. (“Geminus”) 

• 

• 

• 

PWI Holdings, Inc. (“PWI”) 

Professional Warranty Service Corporation (“PWSC”), up until its sale on July 29, 2022 

Trinity Warranty Solutions LLC (“Trinity”) 

IWS is a licensed motor vehicle service agreement company and is a provider of after-market vehicle protection services distributed by 
credit unions in 25 states and the District of Columbia to their members, with customers in all 50 states. 

Geminus  primarily  sells  vehicle  service  agreements  to  used  car  buyers  across  the  United  States,  through  its  subsidiaries,  The  Penn 
Warranty Corporation (“Penn”) and Prime Auto Care Inc. (“Prime”). Penn and Prime distribute these products in 39 and 40 states, 
respectively, via independent used car dealerships and franchised car dealerships. 

PWI markets, sells and administers vehicle service agreements to used car buyers in all fifty states via independent used car and franchise 
networks of approved automobile and motorcycle dealer partners. PWI’s business model is supported by an internal sales and operations 
team and  partners  with  American  Auto  Shield  (“AAS”)  in  three  states  with  a  “white  label”  agreement.  PWI  also  has  a  “white 
label” agreement with Norman & Company, Inc., that sells and administers a guaranteed asset protection product (“GAP”), under the 
Classic product name, in states in which Classic is approved. 

As discussed in Note 5, “Disposal and Discontinued Operations” to the Consolidated Financial Statements, the Company disposed of 
PWSC on July 29, 2022.  The earnings of PWSC are included in the consolidated statements of operations and the segment disclosures 
through the disposal date.  PWSC sells home warranty products and provides administration services to homebuilders and homeowners 
across the United States. PWSC distributes its products and services through an in-house sales team and through insurance brokers and 
insurance carriers throughout all states except Alaska and Louisiana. 

Trinity sells heating, ventilation, air conditioning (“HVAC”), standby generator, commercial LED lighting and commercial refrigeration 
warranty products and provides equipment breakdown and maintenance support services to companies across the United States. As a 
seller of warranty products, Trinity markets and administers product warranty contracts for certain new and used products in the HVAC, 
standby generator, commercial LED lighting and commercial refrigeration industries throughout the United States. Trinity acts as an 
agent on behalf of the third-party insurance companies that underwrite and guaranty these warranty contracts. Trinity does not guaranty 
the performance underlying the warranty contracts it sells. As a provider of equipment breakdown and maintenance support services, 
Trinity acts as a single point of contact to its clients for both certain equipment breakdowns and scheduled maintenance of equipment. 
Trinity will provide such repair and breakdown services by contracting with certain HVAC providers. 

Extended Warranty Products 

Automotive 

IWS, Geminus and PWI market and administer vehicle service agreements (“VSAs”) and related products for new and used automobiles 
throughout the United States. IWS and PWI also market and administer VSAs for motorcycles and ATV’s.  A VSA is an agreement 
between the Company and the vehicle purchaser under which the Company agrees to replace or repair, for a specific term, designated 
vehicle parts in the event of a mechanical breakdown. VSAs supplement, or are in lieu of, manufacturers’ warranties and provide a 
variety of extended coverage options. The cost of the VSA is a function of the contract term, coverage limits and type of vehicle. 

• 

IWS serves as the administrator on all contracts it originates. VSA’s range from one to seven years and/or 12,000 miles to 
125,000 miles. The average term of a VSA is between four and five years. 

•  Geminus goes to market through its subsidiaries, Penn and Prime. Penn and Prime serve as the administrator on all contracts they 
originate and its VSAs range from three months to sixty months and/or 3,000 miles to 165,000 miles. Penn offers a limited product 
line of vehicle service agreements with unlimited miles offerings that have an average term of twelve to twenty-four months. 

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KINGSWAY FINANCIAL SERVICES INC. 

• 

PWI serves as the contract administrator and originator in all states, except for Alaska, Florida and Washington. In those states, 
PWI partners with American Auto Shield (“AAS”) in a white label relationship where the VSAs are branded PWI, are originated 
and administered by AAS, with PWI generating fee income on every contract sold. Across all states, PWI has an extensive menu 
of VSAs with terms starting at three months to ninety-six months and mileage bands up to 200,000 miles. Products range from 
basic Powertrain to the Exclusionary product (“Premier”).  The average term of a VSA is twenty-two months. 

In addition to marketing vehicle service agreements, IWS, Geminus and PWI also administer and broker a GAP product through their 
distribution channels. GAP generally covers a consumer’s out-of-pocket amount, related to an automobile loan or lease, if the vehicle is 
stolen or damaged beyond repair. IWS, Geminus and PWI earn a commission when a consumer purchases a GAP certificate but do not 
take on any insurance risk. 

Home 

PWSC has two insured home warranty products: 

• 

• 

The primary product is designed for new home construction companies, and the warranty is issued to new home buyers. The 
warranty coverage is provided nationwide by a single, A+ rated insurance carrier. The warranty document is an agreement 
between the homebuilder and the purchaser of the home and includes specific tolerances related to covered defects and precise 
definitions of damages. Each damage category includes materials defect coverage for the first year, major systems coverage 
for  the  second  year,  and  workmanship  and  structural  coverage  for  years  three  through  ten.  The  warranty  enables  certain 
damages to be resolved by the homebuilder without admitting fault or negligence, and the warranty offers an efficient method 
to resolve buyer complaints and avoid costly litigation through mediation and mandatory binding arbitration. 

The second insured warranty product is designed for existing homes and covers major systems and appliances. PWSC designs 
the product specifications, but the administration is conducted by an independent third party. PWSC is not a risk-taker on this 
product; instead, it leverages an independent, reputable insurance carrier. PWSC sells this product directly to consumers and 
through various other channels, such as credit unions, brokers, and property managers. 

PWSC  also  has  an  uninsured  warranty  administration  services  program.  The  warranty  document  issued  through  this  program  is  an 
agreement  between  the  homebuilder  and  the  purchaser  of  the  home,  and  it  includes  performance  standards  established  by  the 
homebuilder  and  warrants  conditions  in  the  home  that  could  constitute  a  construction  defect  throughout  the  warranty  period.  This 
program enables construction defects to be efficiently and amicably resolved by the homebuilder through mediation and mandatory 
binding arbitration to avoid costly litigation. Claims are covered for a period of time as may be required by law, for an elected time-
frame by the builder in a specific state, or per agreement with a general liability insurance carrier. The warranty document is designed 
to ensure all parties’ interests are aligned in order to handle their claims relative to construction defects promptly and without attorney 
intervention. 

HVAC 

Trinity  sells  HVAC,  standby  generator,  commercial  LED  lighting  and  commercial refrigeration  warranty  products.  As  a  seller  of 
warranty products, Trinity markets and administers product warranty contracts for certain new and used products in the HVAC, standby 
generator, commercial LED lighting and commercial refrigeration industries throughout the United States. Trinity acts as an agent on 
behalf  of  the  third-party  insurance  companies  that  underwrite  and  guaranty  these  warranty  contracts.  Trinity  does  not  guaranty  the 
performance underlying the warranty contracts it sells. 

Trinity also provides equipment breakdown and maintenance support services to companies across the United States. As a provider of 
such services, Trinity acts as a single point of contact to its clients for both certain equipment breakdowns and scheduled maintenance 
of equipment. Trinity will provide such repair and breakdown services by contracting with certain HVAC providers. 

Marketing, Distribution and Competition 

No Extended Warranty customer or group of affiliated customers accounts for 10% or more of the Company’s consolidated revenues, 
and no loss of a customer or group of affiliated customers would have a material adverse effect on the Company. 

Automotive 

IWS markets its products primarily through credit unions. IWS enters into an exclusive agreement with each credit union whereby the 
credit union receives a stipulated access fee for each vehicle service agreement issued to its members. The credit unions are served by 
IWS employee representatives located throughout the United States in close geographical proximity to the credit unions they serve. IWS 
distributes and markets its products in 25 states and the District of Columbia. 

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IWS  focuses  exclusively  on  the  automotive  finance  market  with  its  core  VSA  and  related  product  offerings,  while  much  of  its 
competition in the credit union channel has a less targeted product approach. IWS’ typical competitor takes a generalist approach to 
market by providing credit unions with a variety of different product offerings. They might be unable to deliver specialty expertise on 
par with IWS and may not give VSA products the attention they require for healthy profitability and strong risk management. 

Geminus  goes  to  market  through  its  subsidiaries,  Penn  and  Prime,  which  market  their  products  primarily  through  independent 
automotive dealerships and franchise automotive dealerships. Penn and Prime enter into dealer wholesale agreements that allow the 
dealer to resell Penn and Prime vehicle service agreements at a retail rate that varies by state as they earn potential commission on the 
remarketing.  The  dealer  base  is  serviced  by  the  Company’s employees  located  throughout  the  United  States  in  close  geographical 
proximity to the dealers they serve. Penn and Prime distribute and market their products in 39 and 40 states, respectively. 

Penn and Prime focus exclusively on the automotive finance market with its core VSA and related product offerings, while much of its 
competition is non-employee based or agent centric. Penn and Prime’s typical competitor’s approach to market is by working through 
non-employees or agents with a variety of different product offerings. Penn and Prime solely focuses on the suite of VSAs it offers, 
which allows the proper attention required for healthy profitability and risk management. 

PWI markets, sells and administers VSAs to used car buyers in all fifty states, primarily through a network of approved automobile 
dealer partners. PWI enters into an agreement with dealer partners that permits dealers to legally sell PWI products to its customers. The 
distribution of PWI VSAs is supported by an internal sales team geographically located around the country and in close proximity to its 
dealer partners. 

PWI operates exclusively in the automotive finance market with its sole focus on VSAs. PWI does operate within a highly competitive 
environment where product pricing and product options are important. Most of its competitors have a comprehensive menu of products 
and services to offer the independent and franchise dealers. PWI’s future strategy will drive additional competitiveness by adding new 
products to its existing menu of VSAs and GAP. PWI’s competitors are a blend of national and regional competitors implementing 
employee and agent-based sales models. 

Home 

PWSC markets its insured warranty products through a sales force directly to the homebuilder and its uninsured builder backed warranty 
products through a network of construction general liability insurance carriers and domestic insurance brokers. Homebuilder prospects 
are  developed  through  membership  in  local  homebuilder  associations,  attendance  at  homebuilder  conventions,  distribution  of 
promotional  products  and  direct  mail  efforts.  For  its  uninsured  homebuilder  backed  product,  PWSC  dedicates  senior  personnel  to 
working  with  the  construction  general  liability  insurers  and  domestic  insurance  brokers  to  identify  and  assist  in  developing  new 
opportunities and devotes marketing resources to sell its product. 

For its insured warranty product, PWSC operates in an environment with several competitors. PWSC differentiates itself through its 
relationship with and backing by an A+ rated global insurance carrier; having over 20 years of experience in the field of new home 
warranty administration; its dispute resolution services; and its best in class customer service. For its uninsured builder backed product, 
PWSC operates in an environment with very few competitors. The most significant features differentiating the builder backed product 
from its competition are an express warranty for all construction defects, the only warranty that is fully integrated with the general 
liability policy in its definition and coverage of construction defects, and mutual agreement between the homebuilder and the home 
buyer that all claims be resolved through mediation or, if necessary, binding arbitration. 

HVAC 

Trinity directly markets and distributes its warranty products to manufacturers, distributors and installers of HVAC, standby generator, 
commercial LED lighting and commercial refrigeration equipment. As a provider of equipment breakdown and maintenance support, 
Trinity directly markets and distributes its product through its clients, which are primarily companies that directly own and operate 
numerous locations across the United States. 

Trinity operates in an environment with few market competitors. Trinity competes on two important facets: its belief that it provides 
superior customer service relative to its competitors and its ability, through the support of its insurance company partners, to provide 
warranty solutions to a wider range of HVAC, standby generator, commercial LED lighting and commercial refrigeration equipment 
customers than that of its competitors. 

Claims Management 

Claims management is the process by which Extended Warranty determines the validity and amount of a claim. The Company believes 
that  claims  management  is  fundamental  to  its  operating  results.  The  Company’s  goal  is  to  settle  claims  fairly  for  the  benefit  of 
policyholders in a manner that is consistent with the policy language and the Company’s regulatory and legal obligations. 

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KINGSWAY FINANCIAL SERVICES INC. 

IWS, Geminus and PWI effectively and efficiently manage claims by utilizing in-house expertise and information systems. They employ 
an experienced claims staff, in some cases comprised of Automotive Service Excellence certified mechanics, knowledgeable in all aspects 
of vehicle repairs and potential claims. Additionally, each  owns a proprietary database of historical claims information that has been 
compiled over several years. Management utilizes these databases to drive real-time pricing adjustments and strategic decision-making. 

Under PWSC’s warranty products, disputes typically arise when there is a difference between what the homeowner expects of the builder 
and  what  the  builder  believes  are  its  legitimate  warranty  service  responsibilities.  PWSC  employs  an  experienced  claims  staff  who 
respond to  all  inquiries  from  homeowners  and  from  requests  by  builders.  Any  inquiries  or  complaints  received  are  submitted  or 
communicated to the builder. PWSC will not make any determination as to the validity or resolution of any complaint; however, PWSC 
will discuss alternatives or resolutions to disputes with all parties and can mediate or negotiate a fair solution to a dispute. This process 
ensures  that  homebuilders  can  effectively  manage  new  home  construction  risk  and  reduce  the  potential  for  substantial  legal  costs 
associated with litigation. PWSC may, at times, act as a third-party administrator for claims under the insured warranty product; however, 
at no time does PWSC bear the loss of claims on warranty products. 

Trinity claims on warranty products are managed by the insurance companies with which Trinity partners. Trinity may, at times, act as 
a third-party administrator of such claims; however, at no time does Trinity bear the loss of claims on warranty products. 

KINGSWAY SEARCH XCELERATOR SEGMENT 

Kingsway Search Xcelerator includes the following subsidiaries of the Company (collectively, “Kingsway Search Xcelerator”), and 
includes the Company’s unique CEO Accelerator program.  Revenue is derived from the provision of business services. 

•  CSuite  

•  Ravix 

• 

SNS 

Business Services 

CSuite provides financial executive services, for project and interim-staffing engagements, and search services for full-time placements 
for customers throughout the United States.  

Ravix provides outsourced finance and human resources consulting services to its clients on a fractional basis for both projects with 
definitive endpoints and ongoing engagements of indeterminate length for customers in several states.  All services are delivered by 
employees who are located in the United States. Ravix offers its services across four different practices: 

   •  Operational  Accounting.  Offers  services  oriented  around  day-to-day  financial  stewardship  of  its  clients,  such  as  bookkeeping, 

accounting, financial reporting and analysis and strategic finance. 

   •  Technical  Accounting.  Provides  specialized  expertise  in  areas  of  technical  accounting,  such  as  initial  public  offerings,  SEC 

reporting and international consolidation; 

   •  Human Resources. Offers human resources, workforce management, and compliance support; and 

   •  Advisory Services. Focuses on managing clients through liquidations and assignment for the benefit of the creditors. 

SNS provides healthcare staffing services to acute healthcare facilities on a contract or per diem basis in the United States, primarily in 
California. Today, SNS is focused on providing temporary registered nurses to hospitals; however, SNS maintains contracts to provide 
allied healthcare professionals to hospitals. SNS offers its services across two different practices:  

   •  Travel  Staffing.   Offers  healthcare staffing  services  to  address  the  short-term  needs  of  hospitals  – contracts have  a guaranteed 

length, which is typically 13 weeks. 

   •  Per Diem Staffing.  Offers healthcare staffing services to meet the day-to-day needs of hospitals. 

6 

  
  
  
  
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 

Marketing, Distribution and Competition 

CSuite actively markets its services via sponsorship of industry events and conferences typically targeted at private equity and related 
service providers. 

Ravix does not actively market its services through traditional channels. Instead, Ravix focuses primarily on venture-capital-funded startups 
and receives most of its new business as a result of business networking activities, referrals from service providers and former clients. 

SNS does not actively market its services through traditional channels. Instead, SNS relies on word-of-mouth to recruit nurses to help 
meet the demands of the hospitals. 

No Kingsway Search Xcelerator customer or group of affiliated customers accounts for 10% or more of the Company’s consolidated 
revenues, and no loss of a customer or group of affiliated customers would have a material adverse effect on the Company. 

CEO Accelerator 

The Company has developed a unique program, whereby it employs dedicated Operator-in-residence (or “Searcher”) personnel whose 
sole function is to search for an appropriate business for Kingsway to acquire and then to ultimately run that business.  As an example, 
our first Searcher, who was hired in May 2020, identified Ravix as a potential acquisition, which the Company closed on in October 
2021.  

The CEO Accelerator focuses on identifying and acquiring privately-held businesses with enterprise values between $10 and $30 million 
where the owner/operator is looking to transition from day-to-day operating responsibilities.  The CEO Accelerator utilizes the proven 
framework  and  characteristics  of  the  Search  Fund  acquisition  model  and  targets  industries  and  companies  with  pre-defined 
characteristics. 

The Company believes that having a dedicated Searcher(s) – whose background includes a mix of real-world work experience and a 
graduate degree (usually a master’s of business administration) – who is ready to transition into the role of CEO gives it a competitive 
advantage over traditional private equity firms and other potential acquirers of businesses in the lower middle market.  

When a search ends with a successful acquisition, the Searcher transitions into an operational role as CEO of the acquired company and 
receives a financial incentive, in the form of various stock-based grants, in the acquired company.  The awards have both time and 
performance vesting requirements, which aligns the incentives with those of the overall Company.  

The Company currently has three full-time Searchers as of December 31, 2022.  The Company intends to maintain this level – and 
potentially expand it – as business opportunities permit. 

PRICING AND PRODUCT MANAGEMENT  

Responsibility for pricing and product management rests with the Company’s individual operating subsidiaries in Extended Warranty 
and Kingsway Search Xcelerator. In Extended Warranty, teams typically comprised of pricing actuaries, product managers and business 
development managers work together by territory to develop policy forms and language, rating structures, regulatory filings and new 
product ideas. Data solutions and claims groups within the individual operating subsidiaries track loss performance monthly to alert the 
operating subsidiaries’ management teams to the potential need to adjust forms or rates.  For Kingsway Search Xcelerator, an annual 
review of billing rates is performed and rates are adjusted to reflect prevailing marketing expectations. 

INVESTMENTS 

The Company manages its investments to support its liabilities, preserve capital, maintain adequate liquidity and maximize after-tax 
investment returns within acceptable risks: 

   •  The fixed maturities portfolios are managed by a third-party firm and are comprised predominantly of high-quality fixed maturities 

with relatively short durations. 

   •  Equity, limited liability and other investments are generally overseen by corporate.   

   •  Limited liability investments, at fair value, investments in private companies and real estate investments are generally overseen by 

corporate, who engages third-party managers for certain holdings. 

The Investment Committee of the Board of Directors is responsible for monitoring the performance of the Company’s investments and 
compliance with the Company’s investment policies and guidelines, which it reviews annually.  

7 

  
  
KINGSWAY FINANCIAL SERVICES INC. 

For further descriptions of the Company’s investments, see “Investments” and “Significant Accounting Policies and Critical Estimates” 
in MD&A and Note 7, “Investments,” and Note 23, “Fair Value of Financial Instruments,” to the Consolidated Financial Statements. 

REGULATORY ENVIRONMENT 

Insurance 

The Company has one U.S. insurance subsidiary, Kingsway Amigo Insurance Company (“Amigo”), which is organized and domiciled 
under the insurance statutes of Florida and is in voluntary run-off.  During 2022, all remaining outstanding claims were settled and 
paid.   As  such,  in  late  2022  the  Company  began  procedures  with  the  Florida  Office  of  Insurance  Regulation  in  order  to 
surrender Amigo’s Certificate of Authority (“COA”) to operate as a property and casualty insurer in the state of Florida, which was 
completed as of March 7, 2023.  As such, Amigo is no longer a regulated insurance company.  To the best of the Company’s knowledge, 
it was in compliance with all applicable regulations. 

Extended Warranty 

Vehicle service agreements are regulated in all states in the United States, and IWS, Geminus and PWI are subject to these regulations. 
Most  states  utilize  the  approach  of  the  Uniform  Service  Contract  Act  that was  adopted  by  the  National  Association  of  Insurance 
Commissioners in the early 1990’s. Under that approach, states regulate vehicle service contract companies by requiring them annually 
to  file  documentation,  together  with  a  copy  of  the  contract  of  insurance  covering  their  liability  under  the  service  contracts,  which 
complies with the particular state’s regulatory requirements. IWS, Geminus and PWI are in compliance with the regulations of each 
state where it sells vehicle service agreements. 

Certain, but not all, states regulate the sale of HVAC and equipment warranty contracts. Trinity is licensed as a service contract provider 
in those states where it is required. 

HUMAN CAPITAL MANAGEMENT 

At December 31, 2022, the Company employed 471 personnel supporting its operations, all of which were full-time employees. None 
of our employees is subject to a collective bargaining agreement and we consider our relationship with our employees to be good. 

We believe the skills and experience of our employees are an essential driver of our business and important to our future prospects. To 
attract qualified applicants and retain our employees, we offer our employees what we believe to be competitive salaries, comprehensive 
benefit packages, equity compensation awards, and discretionary bonuses based on a combination of seniority, individual performance 
and corporate performance. The principal purposes of these employee benefits are to attract, retain, reward and motivate our personnel 
and to provide long-term incentives that align the interests of employees with the interests of our stockholders. 

ACCESS TO REPORTS 

The Company’s Annual Report on Form 10-K, quarterly reports on Form 10-Q, current reports on Form 8-K and amendments to those 
reports filed or furnished pursuant to Section 13(a) or 15(d) of the Securities Exchange Act of 1934 are made available free of charge 
through its website at www.kingsway-financial.com as soon as reasonably practicable after such material is electronically filed with, or 
furnished to, the U.S. Securities and Exchange Commission (“SEC”). 

Item 1A. Risk Factors  

Most issuers, including Kingsway, are exposed to numerous risk factors that could cause actual results to differ materially from recent 
results or anticipated future results. The risks and uncertainties described below are those specific to the Company that we currently 
believe have the potential to be material, but they may not be the only ones we face. If any of the following risks, or any other risks and 
uncertainties that we have not yet identified or that we currently consider not to be material, actually occur or become material risks, 
our business, prospects, financial condition, results of operations and cash flows could be materially and adversely affected. Investors 
are advised to consider these factors along with the other information included in this 2022 Annual Report and to consult any further 
disclosures Kingsway makes in its filings with the SEC. 

FINANCIAL RISK 

We have substantial outstanding recourse debt, which could adversely affect our ability to obtain financing in the future, react 
to changes in our business and satisfy our obligations.  

As of December 31, 2022, we had $90.5 million principal value of outstanding recourse subordinated debt in the form of trust preferred 
securities,  with  redemption  dates  beginning  in  December  2032,  and  which  has  deferred  interest  accrued of  $25.5  million  as 
of December 31, 2022. 

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KINGSWAY FINANCIAL SERVICES INC. 

Pursuant to the indentures governing our outstanding trust preferred securities, we are permitted to defer interest payments for up to 20 
quarters.  During the third quarter of 2018, the Company gave notice to the trustees of its outstanding trust preferred securities of the 
Company’s intention to exercise its voluntary right to defer interest.  On March 2, 2023, we gave notice to the holders of five series of 
our trust preferred securities of our intention to exercise repurchase options no later than March 15, 2023.  We will also pay interest 
accrued during the deferral period on the remaining series of trust preferred securities not subject to repurchase.  After the repurchase is 
completed we will have $15 million of principal outstanding related to the remaining series of trust preferred securities.  The Company 
is currently prohibited from redeeming any shares of its capital stock while payment of interest on the trust preferred securities is being 
deferred.  We also gave notice of our intention to redeem all the outstanding shares of Class A Preferred Stock on March 15, 2023, 
following the repurchase and payment of accrued interest on our trust preferred securities. 

Additionally,  we  incurred  indebtedness  in  connection  with  our  acquisitions  of  PWI  Holdings,  Inc.  and  its  various  subsidiaries 
(collectively,  “PWI”) on December  1,  2020, Ravix  Financial,  Inc.  (“Ravix”)  on October  1,  2021,  CSuite  Financial  Partners,  LLC 
(“CSuite”) on November 1, 2022 and Secure Nursing Service Inc. (“SNS”) on November 18, 2022.  As of as of December 31, 2022, we 
have $34.8 million principal value of such acquisition financing outstanding. 

Because of our substantial outstanding recourse debt: 

• 

• 

• 

our ability to engage in acquisitions without raising additional equity or obtaining additional debt financing could be limited; 

our ability to obtain additional financing for working capital, capital expenditures, acquisitions, debt service requirements or general 
corporate purposes and our ability to satisfy our obligations with respect to our debt may be impaired in the future; 

a large portion of our cash flow must be dedicated to the payment of interest on our debt, thereby reducing the funds available to 
us for other purposes; 

•  we are exposed to the risk of increased interest rates because our outstanding subordinated debt and our outstanding acquisition 
financing bear interest directly related to the London interbank offered interest rate (“LIBOR”), the Secured Overnight Financing 
Rate (“SOFR”) and the Prime Rate; 

• 

it may be more difficult for us to satisfy our obligations to our creditors, resulting in possible defaults on, and acceleration of, 
such debt; 

•  we may be more vulnerable to general adverse economic and industry conditions and may have reduced flexibility to deploy capital 

or otherwise respond to changes; 

•  we may be at a competitive disadvantage compared to our competitors with proportionately less debt or with comparable debt on 

more favorable terms and, as a result, they may be better positioned to withstand economic downturns; 

• 

• 

• 

our ability to refinance debt may be limited or the associated costs to do so may increase; 

our ability to transfer funds among our various subsidiaries and/or distribute such funds to the holding company are limited; 

our flexibility to adjust to changing market conditions and ability to withstand competitive pressures could be limited; 

•  we were unable to redeem outstanding shares of our redeemable preferred stock on the required date, which could lead to increased 

financing costs and/or costs associated with any disputes that might arise involving the holders of such preferred stock; and 

•  we may be prevented from carrying out capital spending that is, among other things, necessary or important to our growth strategy 

and efforts to improve the operating results of our businesses. 

Increases in interest rates would increase the cost of servicing our outstanding recourse debt and could adversely affect our 
results of operation.  

Our outstanding recourse subordinate debt as of December 31, 2022 of $90.5 million principal value bears interest directly related to 
LIBOR (and will in the future bear interest related to SOFR) and our outstanding acquisition financing of $34.8 million related to the 
acquisitions of PWI, Ravix, CSuite and SNS bears interest directly related to either SOFR or the Prime Rate. As a result, increases in 
LIBOR, SOFR and the Prime Rate would increase the cost of servicing our debt and could adversely affect our results of operations. 
Each one hundred basis point increase in LIBOR, SOFR or the Prime Rate would result in an approximately $1.4 million increase in 
our annual interest expense. 

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KINGSWAY FINANCIAL SERVICES INC. 

The expected discontinuation of LIBOR could adversely affect the cost of servicing our outstanding debt.  

Our outstanding recourse subordinate debt, which has redemption dates ranging from December 4, 2032 through January 8, 2034, bear 
interest directly related to LIBOR and extend beyond June 2023, by which time the United Kingdom’s Financial Conduct Authority, 
which regulates LIBOR, has announced it intends to phase out U.S dollar LIBOR. 

The  transition  from  LIBOR  to  other  benchmarks  has  been  the  subject  of  private  sector  and  governmental  activity.  It  is  unclear  if 
alternative rates or benchmarks, such as SOFR, will be widely adopted, and this uncertainty may impact the liquidity of the SOFR loan 
markets. In addition, the transition from LIBOR could have a significant impact on the overall interest rate environment and on our 
borrowing costs. The indentures governing the Company’s outstanding recourse debt and the loan and security agreement governing 
our outstanding acquisition financing provide alternative means of determining the Company’s interest expense on its outstanding debt, 
but at this time, the Company cannot yet reasonably estimate the expected impact of the discontinuation of LIBOR. 

Our operations are restricted by the terms of our debt indentures, which could limit our ability to plan for or react to market 
conditions or meet our capital needs. 

Our  debt  indentures  contain  numerous  covenants  that limit  our  ability,  among  other  things,  to  make  particular  types  of  restricted 
payments and pay dividends or redeem capital stock. The covenants under our debt agreements could limit our ability to plan for or 
react to market conditions or to meet our capital needs. No assurances can be given that we will be able to maintain compliance with 
these covenants. 

If we are not able to comply with the covenants and other requirements contained in the debt indentures, an event of default under the 
relevant debt instrument could occur, which could result in the acceleration of all obligations under such debt instruments. 

The Board of Directors closely monitors the debt and capital position and, from time to time, recommends capital initiatives based upon 
the circumstances of the Company. 

We may not be able to realize our investment objectives, which could significantly reduce our earnings and liquidity. 

We depend on our investments for a substantial portion of our liquidity. As of December 31, 2022, our investments included $37.6 
million  of  fixed  maturities,  at  fair  value.  General  economic  conditions  can  adversely  affect  the  markets  for  interest  rate-sensitive 
instruments,  including  the  extent  and  timing  of  investor  participation  in  such  markets,  the  level  and  volatility  of  interest  rates  and, 
consequently, the fair value of fixed maturities. In addition, changing economic conditions can result in increased defaults by the issuers 
of investments that we own. Interest rates are highly sensitive to many factors, including monetary policies, domestic and international 
economic and political conditions and other factors beyond our control. Given the low interest rate environment that exists for fixed 
maturities, a significant increase in investment yields or an impairment of investments that we own could have a material adverse effect 
on our business, results of operations or financial condition by reducing the fair value of the investments we own, particularly if we 
were forced to liquidate investments at a loss.  

As of December 31, 2022, our investments also included $0.2 million of equity investments, $1.0 million of limited liability investments, 
$17.1 million of limited liability investments, at fair value, $0.8 million of investments in private companies, at adjusted cost and other 
investments, at cost of $0.4 million. These investments are less liquid than fixed maturities. General economic conditions, stock market 
conditions  and  many  other  factors  can  adversely  affect  the  fair  value  of  the  investments  we  own.  If  circumstances  necessitated  us 
disposing of our limited liability investments prematurely in order to generate liquidity for operating purposes, we would be exposed to 
realizing less than their carrying value. 

Our ability to achieve our investment objectives is affected by general economic conditions that are beyond our control and our own 
liquidity needs for operating purposes. We may not be able to realize our investment objectives, which could adversely affect our results 
of operations, financial condition and available cash resources. 

Our business, financial condition and results of operations could be materially and adversely affected by changes in international 
and national economic and industry conditions. 

The COVID-19 pandemic has created significant disruption and uncertainty in the global economy and has negatively impacted our 
business and results of operations and financial condition.  We continue to take steps to assess the effects, and mitigate the adverse 
consequences to our businesses, of the COVID-19 pandemic; however, though the magnitude of the impact continues to develop and 
change as new variants of COVID-19 emerge, our businesses have been and will continue to be adversely impacted by the outbreak of 
COVID-19. 

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KINGSWAY FINANCIAL SERVICES INC. 

In addition to adverse United States domestic and global macroeconomic effects, including the adverse impacts on various industries’ 
supply chains and automobile sales, which has decreased, and may continue to decrease, consumer demand for our products and services, 
reduce our ability to access capital, and otherwise adversely impact the operation of our businesses, the COVID-19 pandemic has caused, 
and will continue to cause, substantial disruption to our employees, distribution channels, investors, tenants, and customers through self-
isolation,  travel  limitations,  business  restrictions,  and  other  means,  all  of  which  has  resulted  in  declines  in  sales.  These  effects, 
individually or in the aggregate, will continue to adversely impact our businesses, financial condition, operating results and cash flows 
and such adverse impacts may be material. 

Additionally,  actual  or  potential  changes  in  international,  national,  regional  and  local  economic,  business  and  financial  conditions, 
including recession, high inflation and trade protection measures and creditworthiness of our customers, may negatively affect consumer 
preferences, perceptions, spending patterns or demographic trends, any of which could adversely affect our business, financial condition, 
results of operations and/or liquidity. 

We are subject to macro-economic fluctuations in the U.S. and worldwide economy. Concerns about consumer and investor confidence, 
volatile corporate profits and reduced capital spending, international conflicts, terrorist and military activity, civil unrest and pandemic 
illness could reduce customer orders or cause customer order cancellations. In addition, political and social turmoil may put further 
pressure on economic conditions in the United States and abroad. The global economy has been periodically impacted by the effects of 
global economic downturns (such as recently related to COVID-19). There can be no assurance that there will not be further such events 
or deterioration in the global economy. These economic conditions make it more difficult for us to accurately forecast and plan our 
future business activities. 

Russia’s invasion and military attacks on Ukraine have triggered significant sanctions from U.S. and European leaders. These events 
may escalate and have created increasingly volatile global economic conditions. Resulting changes in U.S. trade policy could trigger 
retaliatory actions by Russia, its allies and other affected countries, including China, resulting in a “trade war.” Furthermore, if the 
conflict  between  Russia  and  Ukraine  continues  for  a  long  period  of  time,  or  if  other  countries,  including  the  U.S.,  become  further 
involved in the conflict, we could face material adverse effects on our business, financial condition, results of operations and/or liquidity. 

A  difficult  economy  generally  could  materially  adversely  affect the credit,  investment and  financial  markets  which,  in turn, 
could materially adversely affect our business, results of operations or financial condition. 

An adverse change in market conditions, including changes caused by the COVID-19 pandemic, leading to instability in the global 
credit markets presents additional risks and uncertainties for our business. Depending on market conditions going forward, we could 
incur substantial realized and unrealized losses in future periods, which could have an adverse effect on our results of operations or 
financial condition. Certain trust accounts for the benefit of related companies and third-parties have been established with collateral on 
deposit under the terms and conditions of the relevant trust agreements. The value of collateral could fall below the levels required under 
these agreements putting the subsidiary or subsidiaries in breach of the agreements which could expose us to damages or otherwise 
adversely impact our business, financial condition, operating results or cash flows. 

Market volatility may also make it more difficult to value certain of our investments if trading becomes less frequent and the liquidity 
of such investment declines. Disruptions, uncertainty and volatility in the global credit markets may also adversely affect our ability to 
obtain financing for future acquisitions. If financing is available, it may only be available at an unattractive cost of capital, which would 
decrease our profitability or result in our inability to consummate such acquisitions. There can be no assurance that market conditions 
will not deteriorate in the future. 

Financial disruption or a prolonged economic downturn could materially and adversely affect our business. 

Worldwide financial markets have recently experienced periods of extraordinary disruption and volatility, which has been exacerbated 
by the COVID-19 pandemic, resulting in heightened credit risk, reduced valuation of investments and decreased economic activity. 
Moreover, many companies have experienced reduced liquidity and uncertainty as to their ability to raise capital during such periods of 
market disruption and volatility. In the event that these conditions recur or result in a prolonged economic downturn, our results of 
operations,  financial  position  and/or  liquidity  could  be  materially  and  adversely  affected.  These  market  conditions  may  affect  the 
Company’s ability to access debt and equity capital markets. 

We are party to a Settlement Agreement that may require us to make cash payments from time to time, which payments could 
materially adversely affect our business, results of operations or financial condition. 

In May 2016, Aegis Security Insurance Company (“Aegis”) filed a complaint for breach of contract and declaratory relief against the 
Company in the Eastern District of Pennsylvania alleging, among other things, that we breached a contractual obligation to indemnify 
Aegis for certain customs bond losses incurred by Aegis under the indemnity and hold harmless agreements provided by us to Aegis for 
certain customs bonds reinsured by Lincoln General Insurance Company (“Lincoln General”) during the period of time that Lincoln 

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KINGSWAY FINANCIAL SERVICES INC. 

General was a subsidiary of the Company.  Lincoln General was placed into liquidation in November 2015 and Aegis subsequently 
invoked its rights to indemnity under the indemnity and hold harmless agreements. 

Effective January 20, 2020, we entered into a Settlement Agreement with Aegis with respect to such litigation pursuant to which we 
agreed to pay Aegis a one-time settlement amount of $0.9 million and to reimburse Aegis for 60% of future losses that Aegis may 
sustain  in  connection  with  such  customs  bonds,  up  to  a  maximum  reimbursement  amount  of  $4.8  million.  From  2020  to 2022,  the 
Company made reimbursement payments to Aegis totaling $1.0 million in connection with the Settlement Agreement. The timing and 
severity of our future payments pursuant to this Settlement Agreement are not reasonably determinable. No assurances can be given, 
however, that we will not be required to perform under this Settlement Agreement in a manner that has a material adverse effect on our 
business, results of operations or financial condition. 

We have generated net operating loss carryforwards for U.S. income tax purposes, but our ability to use these net operating 
losses could be limited by our inability to generate future taxable income. 

Our U.S. businesses have generated consolidated net operating loss carryforwards (“U.S. NOLs”) for U.S. federal income tax purposes 
of  approximately $644.2 million  as  of  December  31,  2022.  These  U.S.  NOLs  can  be  available  to  reduce  income  taxes  that  might 
otherwise be incurred on future U.S. taxable income and would have a positive effect on our cash flow.  There can be no assurance that 
we will generate the taxable income in the future necessary to utilize these U.S. NOLs and realize the positive cash flow benefit. Also, 
almost all of our U.S. NOLs have expiration dates. There can be no assurance that, if and when we generate taxable income in the future 
from operations or the sale of assets or businesses, we will generate such taxable income before our U.S. NOLs expire. 

We have generated U.S. NOLs, but our ability to preserve and use these U.S. NOLs could be limited or impaired by future 
ownership changes. 

Our ability to utilize the U.S. NOLs after an “ownership change” is subject to the rules of Section 382 of the U.S. Internal Revenue 
Code of 1986, as amended (“Section 382”). An ownership change occurs if, among other things, the shareholders (or specified groups 
of shareholders) who own or have owned, directly or indirectly, five percent (5%) or more of the value of our shares or are otherwise 
treated  as  five  percent  (5%)  shareholders  under  Section  382  and  the  regulations  promulgated  thereunder  increase  their  aggregate 
percentage ownership of the value of our shares by more than fifty (50) percentage points over the lowest percentage of the value of the 
shares owned by these shareholders over a three-year rolling period. An ownership change could also be triggered by other activities, 
including the sale of our shares that are owned by our five percent (5%) shareholders. 

In the event of an ownership change, Section 382 would impose an annual limitation on the amount of taxable income we may offset 
with U.S. NOLs. This annual limitation is generally equal to the product of the value of our shares on the date of the ownership change 
multiplied by the long-term tax-exempt rate in effect on the date of the ownership change. The long-term tax-exempt rate is published 
monthly  by  the  Internal  Revenue  Service.  Any  unused  Section  382  annual  limitation  may  be  carried  over  to  later  years  until  the 
applicable expiration date for the respective U.S. NOLs. In the event an ownership change as defined under Section 382 were to occur, 
our ability to utilize our U.S. NOLs would become substantially limited. The consequence of this limitation would be the potential loss 
of a significant future cash flow benefit because we would no longer be able to substantially offset future taxable income with U.S. 
NOLs. There can be no assurance that such ownership change will not occur in the future. 

Expiration of our tax benefit preservation plan could increase the probability that we will experience an ownership change as 
defined under Section 382. 

In order to reduce the likelihood that we would experience an ownership change without the approval of our Board of Directors, our 
shareholders ratified and approved the tax benefit preservation plan agreement (the “Plan”), dated as of September 28, 2010, between 
the Company and Computershare Investor Services Inc., as rights agent, for the sole purpose of protecting the U.S. NOLs. The Plan 
expired on September 28, 2013. There can be no assurance that our Board of Directors will recommend to our shareholders that a similar 
tax benefit preservation plan be approved to replace the expired Plan; furthermore, there can be no assurance that our shareholders would 
approve any new tax benefit preservation plan were our Board of Directors to present one for shareholder approval. The expiration of 
the Plan, without a new tax benefit preservation plan, exposes us to certain changes in share ownership that we would not be able to 
prevent as we would have been able to prevent under the Plan. Such changes in share ownership could trigger an ownership change as 
defined under Section 382 resulting in restrictions on the use of NOLs in future periods, as discussed above. 

We will only be able to utilize our U.S. NOLs against the future taxable income generated by companies we acquire if we are 
able to include the acquired companies in our U.S. consolidated tax return group. 

We  have  in  the  past  acquired  companies  and  expect  to  do  so  in  the  future.  Our  ability  to  include  acquired  companies  in  our  U.S. 
consolidated tax return group is subject to the rules of Section 1504 of the U.S. Internal Revenue Code of 1986, as amended. If it were 
ever  determined  that  an  acquired  company  did  not  qualify  to  be  included  in  our  U.S.  consolidated  tax  return  group,  such  acquired 
company would be required to file a U.S. tax return separate and apart from our U.S. consolidated tax return group. In that instance, the 

12 

KINGSWAY FINANCIAL SERVICES INC. 

acquired company would be required to pay U.S. income tax on its taxable income despite the existence of our U.S. NOLs, which would 
be a use of cash at the acquired company; furthermore, were the income tax obligation of the acquired company in such instance to be 
greater than its available cash, we could be obligated to contribute cash to our subsidiary to meet its income tax obligation. There can 
be no assurance that an acquired company will generate taxable income and, if an acquired company does generate taxable income, 
there can be no assurance that the acquired company will be allowed to be included in our U.S. consolidated tax return group. 

COMPLIANCE RISK  

If we fail to comply with applicable insurance and securities laws or regulatory requirements, our business, results of operations, 
financial condition or cash flow could be adversely affected. 

As a publicly traded holding company listed on the New York Stock Exchange, we are subject to numerous laws and regulations. These 
laws and regulations delegate regulatory, supervisory and administrative powers to federal, provincial or state regulators. 

Any failure to comply with applicable laws or regulations or the mandates of applicable regulators could result in the imposition of fines 
or significant restrictions on our ability to do business, which could adversely affect our results of operations or financial condition. In 
addition, any changes in laws or regulations (or the interpretation or application thereof, including changes to applicable case law and 
legal precedent) could materially adversely affect our business, results of operations or financial condition. It is not possible to predict 
the future effect of changing federal, state and provincial law or regulation (or the interpretation or application thereof) on our operations, 
and  there  can  be  no  assurance  that  laws  and  regulations  enacted  in  the  future  will  not  be  more  restrictive  than  existing  laws  and 
regulations. 

Our business is subject to risks related to litigation. 

In connection with our operations in the ordinary course of business, at times we are named as defendants in various actions for damages 
and costs allegedly sustained by the plaintiffs. While it is not possible to estimate the loss, or range of loss, if any, that would be incurred 
in connection with any of the various proceedings at this time, it is possible an individual action would result in a loss having a material 
adverse effect on our business, results of operations or financial condition. 

Material weaknesses in our internal control over financial reporting could result in material misstatements in our consolidated 
financial statements. 

We are required to evaluate the effectiveness of the design and operation of our disclosure controls and procedures under the Securities 
Exchange Act of 1934.  As described in Item 9A, Controls and Procedures, of this 2022 Annual Report, in previous years we identified 
the existence of material weaknesses in internal control over financial reporting.  We have one material weakness that has not yet been 
fully remediated.  We are actively engaged in developing and implementing remediation plans as described in Item 9A, Controls and 
Procedures, of this 2022 Annual Report, but we can provide no assurance that additional material weaknesses in our internal control 
over financial reporting will not be identified in the future and that such material weaknesses, if identified, will not result in material 
misstatements in our consolidated financial statements. 

Failure to comply with the NYSE’s continued listing requirements and rules could result in the NYSE delisting our common 
stock, which could negatively affect our company, the price of our common stock and your ability to sell our common stock. 

On April 17, 2020, the Company received a notice from NYSE that the Company was not in compliance with NYSE listing standard 
802.01B because our average global market capitalization over a consecutive 30 trading-day period was less than $50.0 million and 
stockholders’  equity  was  less  than  $50.0  million.  In  accordance  with  the  NYSE  listing  requirements,  we  submitted  a  plan  that 
demonstrated how we expected to return to compliance with NYSE listing standard 802.01B. On July 9, 2020, the NYSE notified us 
that our plan was accepted. On January 18, 2021, NYSE notified us that we were again in compliance with NYSE listing standard 
802.01B but that we were subject to continued monitoring and review for a period of 12 months. While we remained in compliance 
during this 12-month period, we may in the future again fail to be in compliance with the NYSE listing standards and we may be subject 
to corrective action by NYSE, which may include suspension and delisting procedures. 

If we are unable to satisfy the NYSE criteria for continued listing, our common stock would be subject to delisting. A delisting of our 
common stock could negatively impact us by, among other things, reducing the liquidity and market price of our common stock; reducing 
the number of investors willing to hold or acquire our common stock, which could negatively impact our ability to raise equity financing; 
decreasing the amount of news and analyst coverage of us; and limiting our ability to issue additional securities or obtain additional 
financing in the future. In addition, delisting from the NYSE may negatively impact our reputation and, consequently, our business. 

13 

KINGSWAY FINANCIAL SERVICES INC. 

STRATEGIC RISK 

The achievement of our strategic objectives is highly dependent on effective change management. 

Over the past several years we have restructured our operating insurance subsidiaries, including exiting states and lines of business, 
placing subsidiaries into voluntary run-off, terminating managing general agent relationships, hiring a new management team, selling 
Mendota and CMC and acquiring PWI, Ravix, CSuite and SNS with the objective of focusing on our Extended Warranty and Kingsway 
Search  Xcelerator segments,  creating  a  more  effective  and  efficient  operating  structure  and  focusing  on  profitability.  These  actions 
resulted in changes to our structure and business processes. While these changes are expected to bring us benefits in the form of a more 
agile and focused business, success is dependent on management effectively realizing the intended benefits. Change management may 
result in disruptions to the operations of the business or may cause employees to act in a manner that is inconsistent with our objectives. 
Any of these events could negatively affect our performance. We may not always achieve the expected cost savings and other benefits 
of our initiatives. 

We may experience difficulty continuing to retain our holding company staff. 

There can be no assurance that our businesses will produce enough cash flow to adequately compensate and retain staff and to service 
our other holding company obligations, particularly the interest expense burden of our remaining outstanding debt. 

The highly competitive environment in which we operate could have an adverse effect on our business, results of operations or 
financial condition. 

The vehicle service agreement market in which we compete is comprised of a number of companies, including a few large companies, 
which market service agreements on a national basis and have significantly more financial, marketing and management resources than 
we do, as well as several other companies that are somewhat similar in size to our Extended Warranty companies.  There may also be 
other companies of which we are not aware that may be planning to enter the vehicle service agreement industry. 

Competitors in our market generally compete on coverages offered, claims handling, customer service, financial stability and, to a lesser 
extent, price.  Larger competitors of ours benefit from added advantages such as industry endorsements and preferred vendor status.  We 
do not believe that it is in our best interest to compete solely on price.  Instead, we focus our marketing on the total value experience, 
with an emphasis on customer service. While we historically have been able to adjust our product offering to remain competitive when 
competitors have focused on price, our business could be adversely affected by the loss of business to competitors offering vehicle 
service agreements at lower prices. 

Engaging  in  acquisitions  involves  risks,  and,  if  we  are  unable  to  effectively  manage  these  risks,  our  business  could  be 
materially harmed. 

From time to time we engage in discussions concerning acquisition opportunities and, as a result of such discussions, may enter into 
acquisition transactions. 

Acquisitions entail numerous potential risks, including the following: 

• 

• 

• 

• 

• 

difficulties in the integration of the acquired business, including implementation of proper internal controls over financial reporting; 

assumption of unknown material liabilities; 

diversion of management’s attention from other business concerns; 

failure to achieve financial or operating objectives or other anticipated benefits or synergies and/or anticipated cost savings; and 

potential loss of customers or key employees. 

We may not be able to integrate or operate successfully any business, operations, personnel, services or products that we may acquire 
in the future. 

14 

  
  
KINGSWAY FINANCIAL SERVICES INC. 

OPERATIONAL RISK 

Our Extended Warranty subsidiaries’ deferred service fees may be inadequate, which would result in a reduction in our net 
income and could adversely affect our financial condition. 

Our Extended Warranty subsidiaries’ deferred service fees do not represent an exact calculation but are estimates involving actuarial 
and statistical projections at a given point in time of what we expect to be the remaining future revenue to be recognized in relation to 
our remaining future obligations to provide policy administration and claim-handling services. The process for establishing deferred 
service fees reflects the uncertainties and significant judgmental factors inherent in estimating the length of time and the amount of work 
related to our future service obligations. If we amortize the deferred service fees too quickly, we could overstate current revenues, which 
may result in a future significant reversal of revenue and adversely affect future reported operating results. 

As time passes and more information about the remaining service obligations becomes known, the estimates are appropriately adjusted 
upward or downward to reflect this additional information. We cannot assure that we will not have unfavorable re-estimations in the 
future of our deferred service fees and that such unfavorable re-estimations will not have a material adverse effect on our business, 
results of operations or financial condition. In addition, we have in the past, and may in the future, acquire companies that record deferred 
service fees. We cannot assure that the deferred service fees of the companies that we acquire are or will be adequate. 

Extended Warranty’s reliance on credit unions and dealers, as well as our overall reliance on automobile sales could adversely 
affect our ability to maintain business. 

The Extended Warranty business markets and distributes vehicle service agreements through a network of credit unions and dealers in 
the United States. We have competitors that offer similar products exclusively through credit unions and competitors that distribute 
similar products through dealers. Loss of all or a substantial portion of our existing relationships could have a material adverse effect on 
our business, results of operations or financial condition. Moreover, our vehicle service agreement businesses rely heavily on the sale 
of new  and used vehicles  to drive product sales. Accordingly,  a significant decline  in  new  and  used  automobile  sales  could have  a 
material adverse effect on our business, results of operations or financial condition. 

Our reliance on a limited number of warranty and maintenance support clients and customers could adversely affect our ability 
to maintain business. 

We market and distribute our warranty products and equipment breakdown and maintenance support services through a limited number 
of customers and clients across the United States. Loss of all or a substantial portion of our existing customers and clients could have a 
material adverse effect on our business, results of operations or financial condition. 

We  have  reclassified  certain  assets  and  discontinued  a  portion  of  our  operations  which  could  adversely  affect  our  business 
and operations. 

As discussed in Note 5, “Disposal and Discontinued Operations” to our Consolidated Financial Statements, all operations related to 
CMC and VA Lafayette, which serves as a medical and dental clinic for the Department of Veteran Affairs, are included as discontinued 
operations.  In the future, it may be necessary to write-off charges and other costs or incur additional expenses in connection with our 
discontinued operations, which could have a material adverse effect on our business, results of operations or financial condition. 

Additionally, as of December 31, 2022, we classified VA Lafayette as an asset “held for sale”.  We can provide no assurances that we 
will successfully sell VA Lafayette, that we will do so in accordance with our expected timeline or that we will recover the carrying 
value of the assets, which could have a material adverse effect on our business, results of operations or financial condition. Additionally, 
any decisions made regarding our deployment or use of any sales proceeds we receive in any sale involves risks and uncertainties. As a 
result, our decisions with respect to such proceeds may not lead to increased long-term stockholder value. 

CSuite’s  focus  on  serving  private  equity  backed  businesses  creates  exposure  to  general  mergers  and  acquisitions 
(“M&A”) activity.  

CSuite’s  business  opportunities  outside  of  search  are  correlated  with  M&A  activities.  Clients  will  often  engage  CSuite’s  financial 
executive  services  to  prepare  a  business  for  a  transaction  or  to  assist  with  post-acquisition  implementation.  Accordingly,  a  major 
contraction of M&A activity could have a material effect on our business, results of operations or financial condition. 

Ravix’s concentration in venture-capital-funded startups creates exposure to the venture capital funding cycles. 

Ravix focuses on venture-capital-funded companies, often in Silicon Valley, as its clients and receives a significant portion of its referrals 
from service providers focused on servicing the same market. Accordingly, a major contraction of available venture capital funding into 
companies or industries that Ravix services could have a material adverse effect on our business, results of operations or financial condition. 

15 

KINGSWAY FINANCIAL SERVICES INC. 

SNS may experience increased costs that reduce its revenue and profitability if applicable government regulations change. 

The introduction of new regulatory provisions could materially raise the costs associated with hiring temporary employees such as per 
diem and travel nurses. For example, a state could impose sales taxes or increase sales tax rates on temporary healthcare staffing services. 
Furthermore,  if  government  regulations  were  implemented  that  limit the  amount  SNS  is  permitted  to  charge  for  its  services, 
SNS’ profitability could be adversely affected.  

Healthcare  is a  regulated  industry  and  modifications,  inaccurate  interpretations  or  violations of  any applicable  statutory or 
regulatory  requirements  may  result  in  material  costs  or  penalties  as  well  as  litigation  and  could  reduce  SNS’  revenue 
and profitability. 

Healthcare is subject to many complex federal, state, local and international laws and regulations related to professional licensing, the 
payment  of  employees  (e.g.,  wage  and  hour  laws,  employment  taxes,  arbitration  agreements,  and  income  tax  withholdings,  etc.) 
and general business operations (e.g., federal, state and local tax laws). Failure to comply with all applicable laws and regulations could 
result in civil and/or criminal penalties as well as litigation, injunction or other equitable remedies. SNS maintains insurance coverage 
for  employment  claims, however,  SNS’ insurance  coverage  may not be  sufficient  to fully  cover  all claims  against  SNS  or  may not 
continue to be available to SNS at a reasonable cost or without coverage exclusions. If SNS’ insurance does not cover the claim or SNS 
is  otherwise not  able  to  maintain  adequate  insurance  coverage,  SNS  may  be  exposed  to  substantial  liabilities  that  would materially 
impact its business and financial performance. 

SNS’ profitability could be adversely impacted if SNS is unable to adjust its nurse pay rates as the bill rates decline. 

SNS does not have control over the bill rate from hospitals and negotiates the pay rates with the nurses who work with the company. If 
the bill rates decline, SNS will need to renegotiate the pay rates with its nurses and successfully recruit new nurses at lower pay rates. 
SNS’ ability to recruit and retain nurses is contingent on SNS’ ability to offer attractive assignments with competitive wages and benefits 
or payments. 

SNS may be unable to recruit and retain enough quality nurses to meet the demand. 

SNS relies on its ability to attract, develop, and retain nurses who possess the skills, experience and required licenses necessary to meet 
the specified requirements of the healthcare facilities. SNS competes for nurses with other temporary healthcare staffing companies. 
SNS relies on word-of-mouth referrals, as well as social and digital media to attract qualified nurses. If SNS’ social and digital media 
strategy is not successful, SNS’ ability to attract qualified nurses could be negatively impacted. Moreover, the competition for nurses 
remains high as many areas of the United States continue to experience a shortage of qualified nurses. 

Disruptions or security failures in our information technology systems could create liability for us and/or limit our ability to 
effectively monitor, operate and control our operations and adversely affect our reputation, business, financial condition, results 
of operation and cash flows. 

Our information technology systems facilitate our ability to monitor, operate and control our operations. Changes or modifications to 
our information technology systems could cause disruption to our operations or cause challenges with respect to our compliance with 
laws, regulations or other applicable standards. For example, delays, higher than expected costs or unsuccessful implementation of new 
information  technology  systems  could  adversely  affect  our  operations.  In  addition,  any  disruption  in  or  failure  of  our  information 
technology systems to operate as expected could, depending on the magnitude of the problem, adversely affect our business, financial 
condition,  results  of  operation  and  cash  flows,  including  by  limiting  our  capacity  to  monitor,  operate  and  control  our  operations 
effectively. Failures of our information technology systems could also lead to violations of privacy laws, regulations, trade guidelines 
or practices related  to our  customers  and  employees. If our disaster recovery plans do  not work  as  anticipated, or  if  the  third-party 
vendors to which we have outsourced certain information technology or other services fail to fulfill their obligations to us, our operations 
may be adversely affected. Any of these circumstances could adversely affect our reputation, business, financial condition, results of 
operation and cash flows. 

Our success depends on our ability to price accurately the risks we underwrite.  

Our results of operation or financial condition depend on our ability to price accurately for a wide variety of risks. Adequate rates are 
necessary to generate revenues sufficient to pay expenses and to earn a profit. To price our products accurately, we must collect and 
properly  analyze  a  substantial  amount  of  data;  develop,  test  and  apply  appropriate  pricing  techniques;  closely  monitor  and  timely 
recognize changes in trends; and project both severity and frequency of losses with reasonable accuracy. Our ability to undertake these 
efforts successfully, and as a result price our products accurately, is subject to a number of risks and uncertainties, some of which are 
outside our control, including: 

• 

• 

the availability of reliable data and our ability to properly analyze available data; 

the uncertainties that inherently characterize estimates and assumptions; 

16 

KINGSWAY FINANCIAL SERVICES INC. 

• 

• 

our selection and application of appropriate pricing techniques; and 

changes in applicable legal liability standards and in the civil litigation system generally. 

Consequently, we could underprice risks, which would adversely affect our results, or we could overprice risks, which would reduce 
our sales volume and competitiveness. In either case, our results of operation could be materially and adversely affected. 

HUMAN RESOURCES RISK 

Our business depends upon key employees, and if we are unable to retain the services of these key employees or to attract and 
retain additional qualified personnel, our business could be adversely affected. 

Our success at improving our performance will be dependent in part on our ability to retain the services of our existing key employees 
and to attract and retain additional qualified personnel in the future. The loss of the services of any of our key employees, or the inability 
to identify, hire and retain other highly qualified personnel in the future, could adversely affect our results of operations. 

Item 1B. Unresolved Staff Comments 

None. 

Item 2. Properties  

Leased Properties 

Extended Warranty leases facilities with an aggregate square footage of approximately 27,758 at five locations in three states. The latest 
expiration date of the existing leases is in February 2026.   

Kingsway Search Xcelerator leases facilities with an aggregate square footage of approximately 6,085 at three locations in one state. 
The latest expiration date of the existing leases is in January 2027.  

The Company leases a facility for its corporate office with an aggregate square footage of approximately 3,219 at one location in one 
state. The expiration date of the existing lease is in February 2028. 

The properties described above are in good condition. We consider our office facilities suitable and adequate for our current levels 
of operations. 

Owned Properties 

The  LA  Real  Property  is subject  to  a  long-term lease  agreement  and  is  currently  held  for  sale. The  LA  Real  Property  consists  of 
approximately 6.5 acres and contains a 29,224 square foot single-tenant medical office building. 

Item 3. Legal Proceedings 

In connection with its operations in the ordinary course of business, the Company and its subsidiaries are named as defendants in various 
actions for damages and costs allegedly sustained by the plaintiffs. While it is not possible to estimate reasonably the loss, or range of 
loss, if any, that would be incurred in connection with any of the various proceedings at this time, it is possible an individual action 
could result in a loss having a material adverse effect on the Company’s business, results of operations or financial condition. 

See Note 25, “Commitments and Contingent Liabilities,” to the Consolidated Financial Statements, for further information regarding 
the Company’s legal proceedings. 

Item 4. Mine Safety Disclosures 

Not applicable. 

17 

  
  
  
 
 
KINGSWAY FINANCIAL SERVICES INC. 

Part II 

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

Market Information  

Our common shares are listed on the New York Stock Exchange (“NYSE”) under the trading symbol “KFS.”   

The following table sets forth, for the calendar quarters indicated, the high and low sales price for our common shares as reported on 
the NYSE. 

2022 

Quarter 4 
Quarter 3 
Quarter 2 
Quarter 1 

2021 

Quarter 4 
Quarter 3 
Quarter 2 
Quarter 1 

Shareholders of Record 

  $ 

  $ 

NYSE 

High - US$     

Low - US$   

8.08     $ 
7.81       
5.70       
5.60       

5.77     $ 
5.70       
5.24       
5.36       

5.88   
5.69   
5.15   
5.08   

5.04   
4.88   
4.46   
4.35   

As of March 7, 2023 the closing sales price of our common shares as reported by the NYSE was $10.05 per share. 

As of March 8, 2023, we had 25,045,024 common shares issued and outstanding. As of March 8, 2023, there were 9 shareholders of 
record of our common stock. The number of shareholders of record includes one single shareholder, Cede & Co., for all of the shares 
held by our shareholders in individual brokerage accounts maintained at banks, brokers and institutions. 

Dividends  

The Company has not declared a dividend since the first quarter of 2009. The declaration and payment of dividends is subject to the 
discretion  of  our  Board  of  Directors  after  taking  into  account  many  factors,  including  financial  condition,  results  of  operations, 
anticipated cash needs and other factors deemed relevant by our Board of Directors. For a discussion of our cash resources and needs, 
see the “Liquidity and Capital Resources” section of MD&A. 

Securities Authorized for Issuance under Equity Compensation Plans 

The  information  required  related  to  securities  authorized  for  issuance  under  equity  compensation  plans  is  incorporated  herein  by 
reference to the Proxy Statement for our 2022 Annual Meeting of Shareholders, which will be filed with the SEC no later than 120 days 
after the end of our fiscal year ended December 31, 2022. 

Recent Sales of Unregistered Securities 

During the year ended December 31, 2022, we did not have any unregistered sales of our equity securities. 

Issuer Purchases of Equity Securities 

During the year ended December 31, 2022, we did not have any repurchases of our equity securities. 

Item 6. Reserved. 

18 

  
  
  
  
  
  
      
        
  
    
    
    
      
        
  
    
    
    
  
KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

Item 7. MANAGEMENT’S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS 
OF OPERATIONS 

The following management’s discussion and analysis (“MD&A”) of our financial condition and results of operations should be read 
together with the Consolidated Financial Statements included in Part II, Item 8 of this 2022 Annual Report. 

OVERVIEW 

Kingsway is a holding company with operating subsidiaries located in the United States. The Company owns or controls subsidiaries 
primarily  in  the  extended  warranty  and business  services industries.  Kingsway  conducts  its  business  through  the  following 
two reportable segments: Extended Warranty and Kingsway Search Xcelerator. 

Prior to the fourth quarter of 2022, the Company conducted its business through a third reportable segment, Leased Real Estate. Leased 
Real  Estate  included  the  following  subsidiaries  of  the  Company:  CMC  Industries,  Inc.  (“CMC”)  and  VA  Lafayette,  LLC  (“VA 
Lafayette”). 

•  CMC  owned,  through  an  indirect  wholly  owned  subsidiary  (the  “Property  Owner”),  a  parcel  of  real  property  consisting  of 
approximately  192  acres  located  in  the  State  of  Texas  (the  “Real  Property”),  which  is  subject  to  a  long-term  triple  net  lease 
agreement.  The  Real  Property  is  also  subject  to  two mortgages.   On  December  22,  2022,  the  Company  announced  a  definitive 
agreement for the sale of the Real Property, for gross cash proceeds of $44.5 million and the assumption of the mortgages.  On 
December 29, 2022, the sale was completed.  

•  VA  Lafayette  owns real  property  consisting  of  approximately  6.5  acres  and  a  29,224  square  foot  single-tenant  medical  office 
building located in the State of Louisiana (the “LA Real Property”). The LA Real Property serves as a medical and dental clinic for 
the Department of Veteran Affairs and is subject to a long-term lease. The LA Real Property is also subject to a mortgage (the 
“LA Mortgage”).  During  the  fourth  quarter,  the  Company  began  executing a  plan  to sell  VA  Lafayette,  and  as  a  result,  VA 
Lafayette is reported as held for sale at December 31, 2022.   

•  Both CMC and VA Lafayette have been classified as discontinued operations and the results of their operations are reported separately 
for all periods presented.  See Note 5, “Disposal and Discontinued Operations,” to the Consolidated Financial Statements for further 
discussion.  All segmented information has been restated to exclude the Leased Real Estate segment for all periods presented.  

Extended  Warranty  includes  the  following  subsidiaries  of  the  Company:  IWS  Acquisition  Corporation  (“IWS”),  Geminus  Holding 
Company, Inc. (“Geminus”), PWI Holdings, Inc. (“PWI”), Professional Warranty Service Corporation (“PWSC”) and Trinity Warranty 
Solutions  LLC  (“Trinity”).  As  discussed  in Note  5,  “Disposal  and  Discontinued  Operations,” to  the  Consolidated  Financial 
Statements, the Company disposed of PWSC on July 29, 2022.  The earnings of PWSC are included in the consolidated statements of 
operations and the segment disclosures through the disposal date.  Throughout this 2022 Annual Report, the term “Extended Warranty” 
is used to refer to this segment. 

IWS is a licensed motor vehicle service agreement company and is a provider of after-market vehicle protection services distributed by 
credit unions in 25 states and the District of Columbia to their members, with customers in all 50 states. 

Geminus  primarily  sells  vehicle  service  agreements  to  used  car  buyers  across  the  United  States,  through  its  subsidiaries,  The  Penn 
Warranty Corporation (“Penn”) and Prime Auto Care, Inc. (“Prime”). Penn and Prime distribute these products in 39 and 40 states, 
respectively, via independent used car dealerships and franchised car dealerships. 

PWI markets, sells and administers vehicle service agreements to used car buyers in all fifty states via independent used car and franchise 
network of approved automobile and motorcycle dealer partners. PWI’s business model is supported by an internal sales and operations 
team and partners with American Auto Shield in three states with a white label agreement.  PWI also has a “white label” agreement with 
Classic to sell a guaranteed asset protection product (“GAP”) in states that Classic is approved in. 

PWSC sells home warranty products and provides administration services to homebuilders and homeowners across the United States. 
PWSC  distributes  its  products  and  services  through  an  in-house  sales  team  and  through  insurance  brokers  and  insurance  carriers 
throughout all states except Alaska and Louisiana. 

19 

  
  
KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

sells  heating,  ventilation,  air  conditioning 

lighting  and 
(“HVAC”), 
Trinity 
commercial refrigeration warranty products and provides equipment breakdown and maintenance support services to companies across 
the United States. As a seller of warranty products, Trinity markets and administers product warranty contracts for certain new and used 
products in the HVAC, standby generator, commercial LED lighting and commercial refrigeration industries throughout the United 
States. Trinity acts as an agent on behalf of the third-party insurance companies that underwrite and guaranty these warranty contracts. 
Trinity  does  not  guaranty  the  performance  underlying  the  warranty  contracts  it  sells.  As  a  provider  of  equipment  breakdown  and 
maintenance support services, Trinity acts as a single point of contact to its clients for both certain equipment breakdowns and scheduled 
maintenance of equipment. Trinity will provide such repair and breakdown services by contracting with certain HVAC providers. 

standby  generator,  commercial  LED 

Kingsway Search Xcelerator includes the Company’s subsidiaries, CSuite Financial Partners, LLC (“CSuite”), Ravix Financial, Inc. 
(“Ravix”) and Secure Nursing Service LLC (“SNS”).  Throughout this 2022 Annual Report, the term “Kingsway Search Xcelerator” is 
used to refer to this segment. 

CSuite provides financial executive services, for project and interim-staffing engagements, and search services for full-time placements 
for customers throughout the United States.  

Ravix provides outsourced financial services and human resources consulting for short or long duration engagements for customers in 
several states.   

SNS provides healthcare staffing services to acute healthcare facilities on a contract or per diem basis in the United States, primarily in 
California.  

NON U.S.-GAAP FINANCIAL MEASURE 

Throughout this 2022 Annual Report, we present our operations in the way we believe will be most meaningful, useful and transparent 
to anyone using this financial information to evaluate our performance. In addition to the U.S. GAAP presentation of net income, we 
present segment operating income as a non-U.S. GAAP financial measure, which we believe is valuable in managing our business and 
drawing comparisons to our peers. Below is a definition of our non-U.S. GAAP measure and its relationship to U.S. GAAP. 

Segment Operating Income 

Segment  operating  income represents  one  measure  of  the  pretax  profitability  of  our  segments  and  is  derived  by  subtracting  direct 
segment expenses from direct segment revenues. Revenues and expenses presented in the consolidated statements of operations are not 
subtotaled by segment;  however,  this  information  is  available  in  total  and  by  segment  in Note 22,  “Segmented  Information,” to  the 
Consolidated Financial Statements, regarding reportable segment information. The nearest comparable U.S. GAAP measure to total 
segment operating income is income (loss) from continuing operations before income tax expense (benefit) that, in addition to total 
segment operating income, includes net investment income, net realized gains, loss on change in fair value of equity investments, (loss) 
gain on change in fair value of limited liability investments, at fair value, gain on change in fair value of real estate investments, gain 
on change in fair value of derivative asset option contracts, interest expense, other revenue and expenses not allocated to segments, net, 
amortization of intangible assets, loss on change in fair value of debt, gain on disposal of subsidiary and gain on extinguishment of debt 
not allocated to segments.  A reconciliation of total segment operating income to income (loss) from continuing operations before income 
tax expense  (benefit) for  the  years  ended  December  31,  2022  and  December  31,  2021  is  presented  in  Table  1  of  the  “Results  of 
Continuing Operations” section of MD&A. 

SIGNIFICANT ACCOUNTING POLICIES AND CRITICAL ESTIMATES 

The  preparation  of  consolidated  financial  statements  in  conformity  with  U.S.  GAAP  requires  management  to  make  estimates  and 
assumptions  that  affect  the  reported  amounts  and  classification  of  assets  and  liabilities,  revenues  and  expenses,  and  the  related 
disclosures of contingent assets and liabilities in the consolidated financial statements and accompanying notes. Actual results could 
differ from these estimates. Estimates and their underlying assumptions are reviewed on an ongoing basis. Changes in estimates are 
recorded in the accounting period in which they are determined. 

The Company’s most critical accounting policies are those that are most important to the portrayal of its financial condition and results 
of operations, and that require the Company to make its most difficult and subjective judgments, often as a result of the need to make 
estimates of matters that are inherently uncertain. The Company has identified the following as its most critical accounting policies and 
judgments. Although management believes that its estimates and assumptions are reasonable, they are based upon information available 
when they are made, and therefore, actual results may differ from these estimates under different assumptions or conditions. 

20 

KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

Revenue Recognition 

Service  fee  and  commission  revenue  represents  vehicle  service  agreement  fees,  guaranteed  asset  protection  products  (“GAP”) 
commissions,  maintenance  support  service  fees,  warranty  product  commissions,  homebuilder  warranty  service  fees, homebuilder 
warranty commissions and business services consulting revenue based on terms of various agreements with credit unions, consumers, 
businesses and homebuilders. Customers either pay in full at the inception of a warranty contract, commission product sale, or when 
consulting services are billed, or on terms subject to the Company’s customary credit reviews. 

The Company’s revenue recognition policy follows guidance from ASC 606, Revenue from Contracts with Customers, which utilizes a 
five-step revenue recognition framework.  The Company identifies the contract with its customers and then identifies the performance 
obligations in the contracts. The transaction price is determined based on the amount we expect to be entitled to in exchange for providing 
the promised services to the customer. The transaction price is allocated to each distinct performance obligation on a relative standalone 
selling price basis. Revenue is recognized when performance obligations are satisfied. 

Certain of the Company’s contracts with customers include obligations to provide multiple services to a customer. Determining whether 
services are considered distinct performance obligations that should be accounted for separately from one another requires judgment. 
Revenue  from  GAP  commissions  and  homebuilder  warranty  service  fees  contain  multiple  distinct  performance  obligations  that  are 
accounted for separately. 

Judgment is required to determine the standalone selling price (“SASP”) for each distinct performance obligation. Revenue is allocated 
to each performance obligation based on the relative SASP.  SASP are not directly observable in the GAP and homebuilder warranty 
contracts for the separate performance obligations. As a result, the Company has applied the expected cost plus a margin approach to 
develop models to estimate the standalone selling price for each of its performance obligations in order to allocate the transaction price 
to the two separate performance obligations identified.  In these models, the Company makes judgments about which of its actual costs 
are associated with each of the performance obligations.  The relative percentage of expected costs plus a margin associated with these 
performance obligations is applied to the transaction price to determine the estimated SASP of the performance obligations, which the 
Company recognizes as earned as services are performed over the term of the contract period. 

In  certain  jurisdictions  the  Company  is  required  to  refund  to  a  customer  a  pro-rata  share  of  the vehicle  service  agreement  fees  if  a 
customer cancels the agreement prior to the end of the term. Depending on the jurisdiction, the Company may be entitled to deduct from 
the refund a cancellation fee and/or amounts for claims incurred prior to cancellation. While refunds vary depending on the term and 
type of product offered, historically refunds have averaged 9% to 13% of the original amount of the vehicle service agreement fee. 
Revenues recorded by the Company are net of variable consideration related to refunds and the associated refund liability is included in 
accrued expenses and other liabilities. The Company estimates refunds based on the actual historical refund rates by warranty type 
taking into consideration current observable refund trends in estimating the expected amount of future customer refunds to be paid at 
each reporting period. 

Refer to Note 2, “Summary of Significant Accounting Policies,” to the Consolidated Financial Statements for information about our 
revenue recognition accounting policies. 

Valuation of Fixed Maturities and Equity Investments 

Our equity investments, including warrants, are recorded at fair value with changes in fair value recognized in net income. Fair value 
for our equity investments are determined using quoted market values based on latest bid prices, where active markets exist, or models 
based on significant market observable inputs, where no active markets exist. 

For fixed maturities, we use observable inputs such as quoted prices for similar assets in active markets; quoted prices for identical or 
similar  assets  in  markets  that  are  inactive;  or  valuations  based  on  models  where  the  significant  inputs  are  observable  or  can  be 
corroborated by observable market data. We do not have any fixed maturities in our portfolio that require us to use unobservable inputs. 
The  Company  engages  a  third-party  vendor  who  utilizes  third-party  pricing  sources  and  primarily  employs  a  market  approach  to 
determine the fair values of our fixed maturities. The market approach includes primarily obtaining prices from independent third-party 
pricing services as well as, to a lesser extent, quotes from broker-dealers. Our third-party vendor also monitors market indicators, as 
well as industry and economic events, to ensure pricing is appropriate. All classes of our fixed maturities are valued using this technique. 
We have obtained an understanding of our third-party vendor’s valuation methodologies and inputs. Fair values obtained from our third-
party vendor are not adjusted by the Company. 

Gains and losses realized on the disposition of investments are determined on the first-in first-out basis and credited or charged to the 
consolidated statements of operations. Premium and discount on investments are amortized using the interest method and charged or 
credited to net investment income. 

21 

KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

Fixed maturities and equity investments are exposed to various risks, such as interest rate risk, credit risk and overall market volatility 
risk. Accordingly, it is reasonably possible that changes in the fair values of the Company’s investments reported at fair value will occur 
in the near term and such changes could materially affect the amounts reported in the consolidated financial statements. 

Impairment Assessment of Investments 

The establishment of an other-than-temporary impairment on an investment requires a number of judgments and estimates. 

We perform a quarterly analysis of our investments classified as available-for-sale and our limited liability investments to determine if 
any  declines  in  market  value  are  other-than-temporary.  The  analysis  for  available-for-sale  investments  includes  some  or  all  of  the 
following procedures, as applicable: 

• 

• 

• 

• 

• 

• 

• 

identifying all unrealized loss positions that have existed for at least six months; 

identifying other circumstances management believes may affect the recoverability of the unrealized loss positions; 

obtaining a valuation analysis from third-party investment managers regarding the intrinsic value of these investments based on 
their knowledge and experience together with market-based valuation techniques; 

reviewing the trading range of certain investments over the preceding calendar period; 

assessing if declines in market value are other-than-temporary for debt instruments based on the investment grade credit ratings 
from third-party rating agencies; 

assessing if declines in market value are other-than-temporary for any debt instrument with a non-investment grade credit rating 
based on the continuity of its debt service record; 

determining the necessary provision for declines in market value that are considered other-than-temporary based on the analyses 
performed; and 

• 

assessing the Company’s ability and intent to hold these investments at least until any investment impairment is recovered. 

The risks and uncertainties inherent in the assessment methodology used to determine declines in market value that are other-than-
temporary include, but may not be limited to, the following: 

• 

• 

• 

• 

the opinions of professional investment managers could be incorrect; 

the historical trading patterns of individual investments may not reflect future valuation trends; 

the credit ratings assigned by independent credit rating agencies may be incorrect due to unforeseen or unknown facts related to a 
company’s financial situation; and 

the debt service pattern of non-investment grade instruments may not reflect future debt service capabilities and may not reflect a 
company’s unknown underlying financial problems. 

We perform a quarterly analysis of our investments in private companies. The analysis includes some or all of the following procedures, 
as applicable: 

• 

• 

• 

• 

• 

• 

the opinions of external investment and portfolio managers; 

the financial condition and prospects of the investee; 

recent operating trends and forecasted performance of the investee; 

current market conditions in the geographic area or industry in which the investee operates; 

changes in credit ratings; and 

changes in the regulatory environment. 

22 

  
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

As a result of the analysis performed to determine declines in market value that are other-than-temporary, the Company recorded write 
downs  for  other-than-temporary  impairment  related  to  limited  liability  investments,  at  fair  value.  See  “Investments”  section  below 
and Note 7, “Investments,” to the Consolidated Financial Statements for further information. 

Valuation of Limited Liability Investments, at Fair Value 

Limited  liability  investments,  at  fair  value  represent  the  underlying  investments  of  the  Company’s  consolidated  entities  Net  Lease 
Investment Grade Portfolio LLC (“Net Lease”) and Argo Holdings Fund I, LLC (“Argo Holdings”). The Company accounts for these 
investments at fair value with changes in fair value reported in the consolidated statements of operations. 

Net Lease owns investments in limited liability companies that hold investment properties. The fair value of Net Lease’s investments is 
based upon the net asset values of the underlying investments companies as a practical expedient to estimate fair value. 

Argo Holdings makes investments in limited liability companies and limited partnerships that hold investments in search funds and 
private operating companies. The fair value of Argo Holdings’ limited liability investments that hold investments in search funds is 
based on the initial investment in the search funds. The fair value of Argo Holdings’ limited liability investments that hold investments 
in private operating companies is valued using a market approach. 

Refer to Note 23, “Fair Value of Financial Instruments,” to the Consolidated Financial Statements for further information. 

Valuation of Deferred Income Taxes 

The provision for income taxes is calculated based on the expected tax treatment of transactions recorded in our consolidated financial 
statements. In determining our provision for income taxes, we interpret tax legislation in a variety of jurisdictions and make assumptions 
about the expected timing of the reversal of deferred income tax assets and liabilities and the valuation of deferred income taxes. 

The ultimate realization of the deferred income tax asset balance is dependent upon the generation of future taxable income during the 
periods in which the Company’s temporary differences reverse and become deductible. A valuation allowance is established when it is 
more likely than not that all or a portion of the deferred income tax asset balance will not be realized. In determining whether a valuation 
allowance is needed, management considers all available positive and negative evidence affecting specific deferred income tax asset 
balances, including the Company’s historical and anticipated future performance, the reversal of deferred income tax liabilities, and the 
availability of tax planning strategies. 

Objective  positive  evidence  is  necessary  to  support  a  conclusion  that  a  valuation  allowance  is  not  needed  for  all  or  a  portion  of  a 
company’s deferred income tax asset balances when significant negative evidence exists. Cumulative losses are the most compelling 
form of negative evidence considered by management in this determination. To the extent a valuation allowance is established in a 
period, an expense must be recorded within the income tax provision in the consolidated statements of operations. As of December 31, 
2022, the Company maintains a valuation allowance of $130.6 million, all of which relates to its U.S. deferred income taxes. The largest 
component of the U.S. deferred income tax asset balance relates to tax loss carryforwards that have arisen as a result of losses generated 
from the Company’s U.S. operations. Uncertainty over the Company’s ability to utilize these losses over the short-term has led the 
Company to record a valuation allowance. 

Future events may result in the valuation allowance being adjusted, which could materially affect our financial position and results of 
operations. If sufficient positive evidence were to arise in the future indicating that all or a portion of the deferred income tax assets 
would meet the more likely than not standard, all or a portion of the valuation allowance would be reversed in the period that such a 
conclusion was reached, which would beneficially impact our results of operations. 

Accounting for Business Combinations and Asset Acquisitions 

The  Company  evaluates  acquisitions in  accordance  with  Accounting  Standards  Codification  805,  Business  Combinations  (“ASC 
805”), to determine if a transaction represents an acquisition of a business or an acquisition of assets.  

An acquisition of a business represents a business combination.  The acquisition method of accounting is used to account for a business 
combination by assigning the purchase price to tangible and intangible assets acquired and liabilities assumed.  Assets acquired and 
liabilities  assumed  are  recorded  at  their  fair  values  and  the  excess  of  the  purchase  price  over  the  amounts  assigned  is  recorded  as 
goodwill.  We  determine  the  fair  value  of  such  assets  and  liabilities,  often  in  consultation  with  third-party  valuation 
advisors.  Determining the fair value of assets acquired and liabilities assumed requires significant judgment and estimates, including 
the selection of valuation methodologies, estimates of future revenue, costs and cash flows, discount rates, royalty rates, and selection 
of comparable companies.  The resulting fair values and useful lives assigned to acquisition-related intangible assets impact the amount 
and timing of future amortization expense.  Acquired intangible assets with finite lives are amortized over their estimated useful lives. 

23 

KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

Adjustments to fair value assessments are recorded to goodwill over the measurement period, which is not to exceed one year but is 
considered complete once all necessary information is available to management to estimate fair value.  Acquisition costs related to a 
business combination are expensed as incurred. 

When an acquisition does not meet the definition of a business combination either because: (i) substantially all of the fair value of the 
gross assets acquired is concentrated in a single identifiable asset, or group of similar identified assets, or (ii) the acquired entity does 
not have an input and a substantive process that together significantly contribute to the ability to create outputs, the Company accounts 
for the acquisition as an asset acquisition.  In an asset acquisition, goodwill is not recognized.  Any excess of the total purchase price 
plus transaction costs over the fair value of the net assets acquired is allocated on a relative fair value basis to the identifiable net assets 
at the acquisition date.  The net assets acquired in an asset acquisition of property generally include, but are not limited to: land, building, 
building and tenant improvements, and intangible assets or liabilities associated with above-market and below-market leases and in-
place leases. 

The Company’s methodology for determining fair value of the acquired tangible and intangible assets and liabilities includes estimating 
an  “as-if  vacant” fair  value  of  the  physical  property,  which  includes  land,  building,  and  improvements.  In  addition,  the  Company 
determines the estimated fair value of identifiable intangible assets and liabilities, considering the following categories: (i) value of in-
place leases, and (ii) above and below-market value of in-place leases. The value of in-place leases is estimated based on the value 
associated with the costs avoided in originating leases compared to the acquired in-place leases as well as the value associated with lost 
rental and recovery revenue during the assumed lease-up period. The value of in-place leases is amortized on a straight-line basis over 
the remaining lease term and is included in amortization of intangible assets in the consolidated statements of operations. The fair value 
of the above-market or below-market component of an acquired lease is based upon the present value (calculated using a market discount 
rate) of the difference between the contractual rents to be paid pursuant to the lease over its remaining term and management’s estimate 
of the rents that would be paid using fair market rental rates and rent escalations at the date of acquisition over the remaining term of 
the  lease.   An  identifiable  intangible  asset  or  liability  is  recorded  if  there  is  an  above-market  or  below-market  lease  at  an  acquired 
property. The amounts recorded for above-market leases are included in intangible assets on the consolidated balance sheets, and the 
amounts  for  below-market  leases  are  included  in  accrued  expenses  and  other  liabilities  on  the  consolidated  balance  sheets.  These 
amounts  are  amortized  on  a  straight-line  basis  as  an  adjustment  to  rental  revenue  over  the  remaining  term  of  the  applicable 
leases.  Changes to these assumptions could result in a different pattern of recognition. If tenants do not remain in their lease through 
the expected term or exercise an assumed renewal option, there could be a material impact to earnings. 

Valuation and Impairment Assessment of Intangible Assets  

Intangible assets are recorded at their estimated fair values at the date of acquisition. Intangible assets with definite useful lives consist 
of database and customer relationships. Intangible assets with definite useful lives are reviewed for impairment whenever events or 
changes in circumstances indicate that the carrying amount of an asset or asset group may not be recoverable. If circumstances require 
that a definite-lived intangible asset be tested for possible impairment, we first compare the undiscounted cash flows expected to be 
generated by that definite-lived intangible asset to its carrying amount. If the carrying amount of the definite-lived intangible asset is 
not recoverable on an undiscounted cash flow basis, an impairment is recognized to the extent that the carrying amount exceeds its 
fair value. 

Indefinite-lived  intangible  assets  consist  of trade  names,  which are  assessed  for  impairment  annually  as  of  November  30,  or  more 
frequently if events or circumstances indicate that the carrying value may not be recoverable.  The Company may perform its impairment 
test for any indefinite-lived intangible asset through a qualitative assessment or elect to proceed directly to a quantitative impairment 
test, however, the Company may resume a qualitative assessment in any subsequent period if facts and circumstances permit. 

Under the qualitative approach, the impairment test consists of an assessment of whether it is more likely than not that an indefinite-lived 
intangible asset is impaired.  If the Company elects to bypass the qualitative assessment for any indefinite-lived intangible asset, or if a 
qualitative  assessment  indicates  it  is  more  likely  than  not  that  the  estimated  carrying  amount  of  such  asset  exceeds  its  fair  value,  the 
Company performs a quantitative test.  Factors that could trigger a quantitative impairment review include, but are not limited to, significant 
under performance relative to historical or projected future operating results and significant negative industry or economic trends. 

As of November 30, 2022, the Company conducted its annual qualitative assessment.  As a result, the Company determined that certain 
trade names should be further examined under a quantitative approach.  Based on the results of the quantitative approach, the estimated 
fair values of the trade names exceeded their respective carrying values; therefore, the Company did not record any impairment. 

No impairment charges were recorded against intangible assets in 2022 or 2021. Additional information regarding our intangible assets 
is included in Note 9, “Intangible Assets,” to the Consolidated Financial Statements. 

24 

KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

Goodwill Recoverability 

Goodwill is assessed for impairment annually as of November 30, or more frequently if events or circumstances indicate that the carrying 
value may not be recoverable. In evaluating the recoverability of goodwill, the Company estimates the fair value of its reporting units 
and compares it to the carrying value. If the carrying value of the reporting unit exceeds its fair value, an impairment loss is recognized 
in an amount equal to such excess. 

For Extended Warranty,  the Company  estimates  the fair value using  a valuation  technique  based on observed  market  capitalization 
multiples of earnings before interest, taxes, depreciation and amortization (“EBITDA”) for a group of publicly traded insurance services 
and insurance brokerage companies, an approach that the Company views as a technique consistent with the objective of measuring fair 
value consistent with prior years’ assessments performed. 

For  Kingsway  Search  Xcelerator,  the  Company  estimates  the  fair  value  using a  valuation  technique  based  on  observed  market 
capitalization multiples of EBITDA from its recent acquisitions of similar businesses.   

Estimating the fair value of reporting units requires the use of significant judgments that are based on a number of factors including 
actual operating results, internal forecasts, market observable pricing multiples of similar businesses and comparable transactions and 
determining the appropriate discount rate and long-term growth rate assumptions. There are inherent uncertainties related to these factors 
and management’s judgment in applying them to the analysis of goodwill impairment. It is reasonably possible that the judgments and 
estimates described above could change in future periods. 

Although the Company believes its estimates of fair value are reasonable, actual financial results could differ from those estimates due 
to  the  inherent  uncertainty  involved  in  making  such  estimates.  Changes  in  assumptions  concerning  future  financial  results  or  other 
underlying  assumptions  could  have  a  significant  impact  on  either  the  fair  value  of  the  reporting  units,  the  amount  of  the  goodwill 
impairment charge, or both. 

No impairment charges were recorded against goodwill in 2022 or 2021, as the estimated fair values of the reporting units exceeded 
their respective carrying values. Additional information regarding our goodwill is included in Note 8, “Goodwill,” to the Consolidated 
Financial Statements. 

Deferred Contract Costs 

Deferred contract costs represent the deferral of incremental costs to obtain or fulfill a contract with a customer.  Incremental costs to 
obtain a contract with a customer primarily include sales commissions.  The Company capitalizes costs incurred to fulfill a contract if 
the  costs are  identifiable,  generate  or  enhance  resources  used  to  satisfy  future  performance  obligations  and  are  expected  to  be 
recovered.   Costs  to  fulfill  a  contract include  labor  costs  for set-up  activities  directly  related  to  the  acquisition  of  vehicle  service 
agreements.  Contract costs are deferred and amortized over the expected customer relationship period consistent with the pattern in 
which  the  related  revenues  are  earned.  Amortization  of  incremental  costs to  obtain  a  contract  and  costs  to  fulfill  a  contract with  a 
customer  are  recorded  in  commissions  and general  and  administrative  expenses,  respectively, in  the consolidated  statements  of 
operations.  No impairment charges related to deferred contract costs were recorded in 2022 or 2021. 

Fair Value Assumptions for Subordinated Debt Obligations 

Our subordinated debt is measured and reported at fair value. The fair value of the subordinated debt is calculated using a model based 
on significant market observable inputs and inputs developed by a third-party. These inputs include credit spread assumptions developed 
by a third-party and market observable swap rates.  The following summarizes the impacts: 

Impact of Rate Change on Fair Value 

2022 Result 

2021 Result 

Libor: 
increase causes fair value to increase; decrease causes fair value to decrease 
Risk free rate: 
increase causes fair value to decrease; decrease causes fair value to increase 

   Increase to fair value     Increase to fair value    

   Decrease to fair value    Decrease to fair value   

The  other  primary  variable  affecting  the  fair  value  of  debt  calculation  is  the  passage  of  time,  which  will  always  have  the  effect  of 
increasing the fair value of debt. 

Therefore, changes in the underlying interest rates used would cause the fair value to be impacted, but only impacts the income statement 
(or comprehensive income/loss for the portion related to credit risk) and does not impact cash flows. 

25 

  
  
  
  
  
     
     
  
  
  
     
     
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

Fair Value Assumptions for Subsidiary Stock-Based Compensation Awards 

Three of the Company’s subsidiaries, PWSC, Ravix and SNS, have made grants of restricted stock awards or restricted unit awards 
(together  “Subsidiary  Restricted  Awards”).  The  Subsidiary  Restricted  Awards  are  measured  at  fair  value  on  the  date  of  grant  and 
recognized as compensation expense on a straight-line basis over the requisite service period during which awards are expected to vest, 
with  a  corresponding  increase  to  either  additional  paid-in  capital  for  equity-classified  awards  or  to  a  liability  for  liability-classified 
awards.  Certain of the Subsidiary Restricted Awards are classified as a liability, either because they contain a noncontingent put option 
that is exercisable less than six months after the vesting of certain shares or because the awards are expected to settle in cash. Liability-
classified awards, included in accrued expenses and other liabilities in the consolidated balance sheets, are measured and reported at fair 
value on the date of grant and are remeasured each reporting period. The Subsidiary Restricted Awards contain performance vesting 
and/or market vesting conditions.  Performance vesting conditions are reviewed quarterly to assess the probability of achievement of 
the  performance  condition.   Compensation  expense  is  adjusted  when  a  change  in  the  assessment  of  achievement  of  the  specific 
performance condition is determined to be probable. Compensation expense is recognized on a straight-line basis for awards subject to 
market  conditions  regardless  of  whether  the  market  condition  is  satisfied,  provided  that  the  requisite  service  has  been 
provided.  Forfeitures are recognized in the period that Subsidiary Restricted Awards are forfeited.  

The determination of fair value of the Subsidiary Restricted Awards is subjective and involves significant estimates and assumptions of 
whether the awards will achieve performance thresholds.  The fair value of the Subsidiary Restricted Awards is estimated using either an 
internal  valuation  model without  relevant  observable  market  inputs, the  Black-Scholes  option  pricing  model  and/or  the  Monte  Carlo 
simulation model to derive certain inputs. The significant inputs used in the internal valuation model includes a valuation multiple applied 
to trailing twelve month earnings before interest, tax, depreciation and amortization. The determination of the grant date fair value using 
the  Black-Scholes  option-pricing  model  is  affected  by  subjective  assumptions,  including  the  expected  term  of  the  awards,  expected 
volatility over the expected term of the awards, expected dividend yield, and risk-free interest rates. The determination of the grant date 
fair value using the Monte Carlo simulation model is affected by subjective assumptions, including the expected term of the awards, 
expected  volatility  over  the  expected  term  of  the  awards and  risk-free  interest  rates.  The  assumptions used  in  the  Company’s  Black-
Scholes option-pricing and Monte Carlo simulation models requires significant judgment and represents management’s best estimates. 

Derivative Financial Instruments 

Derivative  financial  instruments  include  interest  rate  swap  contract and  the  trust  preferred  debt repurchase  options.  The  Company 
measures derivative financial instruments at fair value. The fair value of derivative financial instruments is required to be revalued each 
reporting period, with corresponding changes in fair value recorded in the consolidated statements of operations. Realized gains or losses 
are recognized upon settlement of the contracts.  See Note 11, “Derivatives” and Note 23, “Fair Value of Financial Instruments” to 
the Consolidated Financial Statements, for further discussion. 

Contingent Consideration 

The consideration for certain of the Company’s acquisitions include future payments to the former owners that are contingent upon the 
achievement of certain targets over future reporting periods. Liabilities for contingent consideration are measured and reported at fair 
value at the date of acquisition with subsequent changes in fair value reported in the consolidated statements of operations as non-
operating other (expense) revenue. 

Determining the fair value of contingent consideration liabilities requires management to make assumptions and judgments. The fair 
value  of  Company’s  contingent  consideration  liabilities is  estimated  by  applying  the Monte  Carlo simulation  method to  forecast 
achievement  of  gross  profit  or  gross  revenue.  These  fair  value  measurements  are  based  on  significant  inputs  not  observable  in  the 
market.  Key inputs in the valuations include forecasted gross profit or revenue, gross profit or revenue volatility, discount rate and 
discount term. Management must use judgment in determining the appropriateness of these assumptions as of the acquisition date and 
for each subsequent period. Changes in assumptions could have a material impact on the amount of contingent consideration benefit or 
expense reported in the consolidated statements of operations and have an impact on the payout of contingent consideration liabilities. 
Contingent consideration liabilities are revalued each reporting period. Changes in the fair value of contingent consideration liabilities 
can result from changes to one or multiple inputs, including adjustments to the key inputs or changes in the assumed achievement or 
timing  of  any  targets.  Any  changes  in  fair  value  are  reported  in  the  consolidated  statements  of  operations  as  non-operating other 
(expense)  revenue.  Additional  information  regarding  our  contingent  consideration  liabilities  is  included  in Note  23,  “Fair  Value  of 
Financial Instruments,” to the Consolidated Financial Statements. 

26 

KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

RESULTS OF CONTINUING OPERATIONS  

A reconciliation of total segment operating income to net income for the years ended December 31, 2022 and December 31, 2021 is 
presented in Table 1 below: 

Table 1 Segment Operating Income for the Years Ended December 31, 2022 and December 31, 2021  
For the years ended December 31 (in thousands of dollars) 

Segment operating income (loss) 
Extended Warranty 
Kingsway Search Xcelerator 
Total segment operating income 
Net investment income 
Net realized gains 
Loss on change in fair value of equity investments 
(Loss) gain on change in fair value of limited liability investments, at fair value 
Gain on change in fair value of real estate investments 
Gain on change in fair value of derivative asset option contracts 
Interest expense 
Other revenue and expenses not allocated to segments, net 
Amortization of intangible assets 
Loss on change in fair value of debt 
Gain on disposal of subsidiary 
Gain on extinguishment of debt not allocated to segments 
Income (loss) from continuing operations before income tax expense (benefit) 
Income tax expense (benefit) 
Income (loss) from continuing operations 
(Loss) income from discontinued operations, net of taxes 
Loss on disposal of discontinued operations, net of taxes 
Net income 

2022   

2021    Change 

9,879   
3,548   
13,427   
2,305   
1,209   
(26)   
(1,754)   
1,488   
16,730   
(8,092)   
(17,206)   
(6,133)   
(4,908)   
37,917   
—   
34,957   
4,825   
30,132   
(12,805)   
(2,262)   
15,065   

12,636   
484   
13,120   
1,575   
1,809   
(242)   
2,391   
—   
—   
(6,161)   
(11,395)   
(4,837)   
(3,201)   
—   
311   
(6,630)   
(3,916)   
(2,714)   
4,574   
—   
1,860   

(2,757) 
3,064 
307 
730 
(600) 
216 
(4,145) 
1,488 
16,730 
(1,931) 
(5,811) 
(1,296) 
(1,707) 
37,917 
(311) 
41,587 
8,741 
32,846 
(17,379) 
(2,262) 
13,205 

Segment Operating Income, Income (Loss) from Continuing Operations and Net Income  

For the year ended December 31, 2022, we reported segment operating income of $13.4 million compared to $13.1 million for the 
year ended December 31, 2021.  The increase is primarily due to the following items: 

• 

• 

• 

Increased operating income from Kingsway Search Xcelerator, primarily due to including Ravix for twelve months in 2022 
(acquired October 2021), as well as the November 2022 acquisitions of CSuite and SNS, which was partially offset by  

2021 operating income in Extended Warranty segment includes a gain on extinguishment of debt of $2.2 million, related to 
Paycheck Protection Program (“PPP”) loan forgiveness, while there was zero in 2022; 

2022 operating income includes a reduction to IWS operating income of $0.9 million, due to a change in estimate of IWS’ 
deferred revenue and deferred contract costs associated with vehicle service contract fees; and 

•  The  disposal  of  PWSC  as  of  July  29,  2022,  which  had  segment  operating  income  of  $0.1  million  and  $2.6 

million for 2022 and 2021, respectively. 

For  the  year  ended  December  31,  2022,  we  reported income  from  continuing  operations  of  $30.1 million compared  to  a  loss  from 
continuing  operations  of  $2.7 million for  the  year  ended  December  31,  2021.  The  income  from  continuing  operations for 2022 is 
primarily due to:  

•  A gain on disposal of subsidiary of $37.9 million, related to the sale of PWSC; 

•  A gain  on  change  in  fair  value  of  derivative  asset  option  contracts  of $16.7 million,  related  to  the  trust  preferred  debt 

repurchase options; 

27 

  
  
  
     
     
     
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

•  A gain on change in fair value of real estate investments of $1.5 million; all of which were partially offset by 

•  An increase in interest expense related to rising interest rates; 

•  Other  revenue  and  expenses  not  allocated  to  segments,  net,  which  includes  a $4.8 million increase  in  the  fair  value 
of previously-granted awards  to PWSC  employees  that  are  accounted  for  on  a  fair  value  basis  and $1.2 million  increase 
in expense due to the increase in fair value of the Ravix contingent consideration; 

•  Loss on change in fair value of debt, which increased by $1.7 million; 

•  Loss on change in fair value of limited liability investments, at fair value which increased by $4.1 million (see below); and 

• 

Income tax expense which increased by $8.7 million.  The income tax expense in 2022 is primarily due to the state tax expense 
associated  with  the  sale  of  PWSC  on  July  29,  2022  and  the  related  increase  in  valuation  allowance  from  the  accelerated 
utilization  of  indefinite  life  interest  expense  carryforwards  as  a  result  of  such  sale.   The  income  tax  benefit  in  2021  is 
primarily due  to  the  release of valuation  allowance  as  a  result  of deferred  tax  liabilities  available  in  2021  arising from  the 
acquisitions of Ravix Financial and PWI available to offset existing deferred tax assets. 

The  loss  from  continuing  operations for  the  year  ended   December  31,  2021 is  primarily  due  to operating  income  in  Extended 
Warranty (which includes gain on extinguishment of debt of $2.2 million, related to PPP loan forgiveness) that was negatively impacted 
by recording  a  $1.9 million non-cash,  cumulative reduction  to  service  fee  and  commission revenue relating  to  the decrease  in  PWI 
acquired deferred service fees as a result of finalizing the purchase accounting, net investment income, net realized gains, gain on change 
in fair value of limited liability investments, at fair value and income tax benefit, partially offset by interest expense, other revenue and 
expenses  not  allocated  to  segments,  net,  increased  amortization  of  intangible  assets as  a  result  of  a  $1.9  million  non-
cash, cumulative adjustment related to finalizing the PWI purchase accounting and loss on change in fair value of debt. 

For  the  year  ended  December  31,  2022,  we  reported net  income  of $15.1 million  compared  to $1.9 million for  the  year  ended 
December 31,  2021.   In  addition  to  the  items  described  above  impacting  income  (loss) from  continuing  operations,  the 
net income includes: 

•  A loss from discontinued operations, net of taxes of $12.8 million and income from discontinued operations, net of taxes of 

$4.6 million for the years ended December 31, 2022 and December 31, 2021, respectively; 

•  A loss on disposal of discontinued operations, net of taxes of $2.3 million for the year ended December 31, 2022. 

The loss from discontinued operations is related to the operations of CMC and VA Lafayette and is primarily due to a final management 
fee of $16.4 million resulting from the sale of the CMC railyard. 

The loss on disposal of discontinued operations includes the gain on disposal of CMC of $0.2 million and a loss of $2.5 million related 
to a liability recorded at September 30, 2022 regarding the Company’s obligation to indemnify a former subsidiary for open claims (the 
maximum  liability  under  the  indemnity  is  $2.5  million).   See Note  5  “Disposal  and  Discontinued  Operations,” to  the  Consolidated 
Financial Statements, for further discussion. 

Extended Warranty 

The  Extended  Warranty  service  fee  and  commission  revenue  decreased  0.1%  (or  $0.9  million)  to  $74.0  million  for  the  year  ended 
December 31, 2022 compared with $74.9 million for the year ended December 31, 2021.  Service fee and commission revenue was 
impacted by the following in 2022: 

•  A $3.1 million decrease at PWSC, due to the sale of PWSC on July 29, 2022 (the financial results for PWSC are only included 

through the disposal date); 

•  A  $0.7 million  decrease  at  Geminus,  due  to  the continued  supply-chain  issues  in  the  automotive  industry,  resulting  in 
significant increases in the prices of used automobiles, making it difficult for smaller automobile dealers to obtain inventory 
and, therefore, putting downward pressure on revenue; both of which were partially offset by 

•  A $1.3 million increase at PWI. During the third quarter of 2021, PWI recorded a $1.9 million non-cash, cumulative reduction 
to service fee and commission revenue relating to the decrease in PWI acquired deferred service fees as a result of finalizing 
the purchase accounting.  This was partially offset by similar macro-economic conditions as explained above for Geminus, as 
well as a restructuring of leadership at PWI that has resulted in a higher focus salesforce production; 

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KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

•  A $1.2 million increase at Trinity, primarily driven by a $0.9 million increase in its equipment breakdown and maintenance 

support services, as Trinity continues to recover from the original impacts of the COVID-19 pandemic; and 

•  A $0.4 million increase at IWS.  During the first quarter of 2022, there was a change in estimate of IWS’ deferred revenue 
associated with vehicle service contract fees, which resulted in a reduction to IWS revenue of $1.2 million.  This reduction was 
more than offset by an increase in revenue due primarily to an increase in the number of VSAs written in 2022, as sales volume 
continues to trend up towards pre-COVID levels.  IWS sells a substantial amount of VSAs for new automobiles but, more 
importantly, its products are distributed through credit unions at the point of vehicle financing, which has been less impacted 
by the recent macro-economic conditions. 

The Extended Warranty operating income was $9.9 million for the year ended December 31, 2022 compared with $12.6 million for the 
year ended December 31, 2021.  The 2021 operating income results include a $1.9 million non-cash, cumulative reduction to service 
fee  and  commission  revenue  relating  to  the  decrease  in  PWI  acquired  deferred  service  fees  as  a  result  of  finalizing  the 
purchase accounting. 

Operating income was primarily impacted by the following: 

• 

Inclusion of PPP loan forgiveness related to Extended Warranty companies of $2.2 million for 2021, of which there was zero 
in 2022; 

•  A 1.1 million decrease at PWSC to an operating income of $0.9 million, primarily due to the sale of PWSC on July 29, 2022;  

•  A $0.5 million decrease at Geminus to $1.3 million, due to a decrease in revenue that was partially offset by a slight decrease 

in general and administrative expenses; all of which were partially offset by 

•  A  $0.5 million  increase  at  IWS  to  $4.0 million,  primarily due  to  increased  revenue.   This was  partially  offset  by a  change 
in estimate of IWS’ deferred revenue and deferred contract costs associated with vehicle service contract fees, which resulted in 
a reduction to IWS operating income of $0.9 million in 2022.  Also, during 2022, IWS had a slight increase in commission and 
claims expense, as a decrease in the number of claims was slightly more than offset by an increase in the average cost of a claim; 

•  A $0.3 million  increase  at  PWI  to  $2.1 million. The  2021  results  include a  $1.9  million  non-cash, cumulative reduction  to 
service fee and commission revenue relating to the decrease in PWI acquired deferred service fees as a result of finalizing the 
purchase accounting.  The operating income for 2022 was impacted by an increase in claims expense (decreased volume of 
claims that was more than offset by a higher average cost per claim) compared to 2021; and 

•  A $0.2 million increase at Trinity to $1.7 million, primarily due to an increase in revenue that was partially offset by an increase 

in cost of services sold and higher general and administrative expenses compared to 2021. 

Kingsway Search Xcelerator 

The Kingsway Search Xcelerator revenue increased to $19.2 million for the year ended December 31, 2022 compared with $3.5 million 
for  the  year  ended  December  31,  2021.   Kingsway  Search  Xcelerator  operating  income  was  $3.5  million for  the  year  ended 
December 31, 2022 compared with $0.5 million for the year ended December 31, 2021.  The increase in revenue and operating income 
is primarily due to the inclusion of Ravix for a full year in 2022 following its acquisition effective October 1, 2021, as well as revenue 
and operating income derived from CSuite and SNS, which were acquired on November 1, 2022 and November 18, 2022, respectively. 

Net Investment Income  

Net investment income was $2.3 million in 2022 compared to $1.6 million in 2021. The increase in 2022 relates primarily to higher 
investment  income  from the  Company’s  limited  liability  investments,  fixed  maturities  and  cash  equivalents.   The  Company  also 
benefited  from  increasing  interest  rates  and  an  increase  in  the  Company’s  unrestricted  cash  balance  (from  $10.1  million  as  of 
December 31, 2021 to $64.2 million as of December 31, 2022). 

The increases above were partially offset by a decrease in investment income from the Company’s limited liability investments, at fair 
value, which is recognized based on the Company’s share of the earnings of the limited liability entities. 

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KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

Net Realized Gains  

The Company recorded net realized gains of $1.2 million in 2022 compared to $1.8 million in 2021.  The net realized gains for 2022 and 
2021 primarily relate to: 

•  Net realized gains on sales of limited liability investments; 

•  Realized gains recognized by Argo Holdings Fund I, LLC (“Argo Holdings”); and 

•  Distributions received from one of the Company’s investments in private companies in which its carrying value previously 

had been written down to zero as a result of prior distributions. 

(Loss) Gain on Change in Fair Value of Limited Liability Investments, at Fair Value 

Loss on change in fair value of limited liability investments, at fair value was $1.8 million in 2022 compared to a gain of $2.4 million 
in 2021. The loss for the year ended December 31, 2022 represents decreases in fair value of $0.9 million related to Net Lease Investment 
Grade  Portfolio  LLC  (“Net  Lease”)  and  $0.8  million  related  to  Argo  Holdings.   The  remaining  property  in  Net  Lease  was  sold  in 
February 2023. 

The gain for the year ended December 31, 2021 includes increases in fair value of $1.6 million related to Net Lease, due to the sale of 
one of the Net Lease investment properties, and $0.8 million related to Argo Holdings. 

Gain on Change in Fair Value of Real Estate Investments 

Gain  on  change  in  fair  value  of  real  estate  investments  was $1.5 million  in 2022  compared  to  zero  in  2021.  Real  estate 
investments solely relates to investment real estate properties held by the Company’s consolidated subsidiary, Flower Portfolio 001, 
LLC (“Flower”).  The Company consolidates the financial statements of Flower on a three-month lag.  The increase in fair value is 
attributable to the sale of the Flower real estate investment properties for $12.2 million, which closed on September 29, 2022.   As a 
result of the three-month lag, the Company recorded the sale transaction in its fourth quarter 2022 financial statements. 

Gain on Change in Fair Value of Derivative Asset Option Contracts 

Gain on change in fair value of derivative asset option contracts was $16.7 million in 2022 compared to zero in 2021, due to the fact 
that the  Company  entered  into  three option  agreements  during  the  third  quarter  of  2022  to  repurchase  a  significant  portion  of  its 
subordinated debt.  The amount relates to the difference between the value of the option at date of inception and the cash consideration 
paid of (total of $11.4 million), and the subsequent change in fair value of $5.3 million through December 31, 2022. 

Refer to Note 11, “Derivatives,” to the Consolidated Financial Statements, for further information on the option agreements. 

Interest Expense  

Interest expense for 2022 was $8.1 million compared to $6.2 million in 2021. The increase in 2022 is primarily attributable to: 

• 

$2.1  million  higher  interest  expense  on  the  Company’s subordinated  debt,  which  resulted  from  generally  higher  London 
interbank  offered  interest  rates (“LIBOR”)  for  three-month  U.S.  dollar  deposits  during 2022  compared  to  2021.  The 
Company’s subordinated debt bears interest at the rate of LIBOR, plus spreads ranging from 3.85% to 4.20%;  

•  An increase of $0.3 million related to the 2021 Ravix Loan, which was effective October 1, 2021, and has an annual interest 

rate equal to the greater of the Prime Rate plus 0.5%, or 3.75% (current rate of 8.00%);  

•  An increase of $0.1 million related to the new $6.0 million 2022 Ravix Loan, which was effective November 16, 2022 and has 

an annual interest rate equal to the Prime Rate plus 0.75% (current rate of 8.25%);  

•  An increase of $0.1 million related to the new $6.5 million SNS Loan, which was effective November 18, 2022 and has an 
annual interest  rate  equal  to  the  greater  of  the  Prime Rate plus  0.5%,  or  5.00%  (current  rate  of 8.00%);  all  of  which  were 
partially offset by  

•  A decrease of $0.4 million, related to the 2020 KWH Loan, as a result of lower principal balance, as well as an increase in fair 

value of the interest rate swap related to the 2020 KWH bank loan; and  

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KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

•  A decrease of $0.1 million related to notes payable at Net Lease.  The Net Lease debt was repaid in the fourth quarter of 2020, 
however due to the three-month reporting lag for Net Lease, the Company continued to report interest expense through the 
first quarter of 2021 related to the Net Lease debt. 

See “Debt” section below for further details. 

Other Revenue and Expenses not Allocated to Segments, Net 

Other  revenue  and  expenses  not  allocated  to  segments  was  a  net  expense  of  $17.2  million  in 2022  compared  to  $11.4  million  in 
2021.  Included are revenue and expenses associated with our various other investments that are accounted for on a consolidated basis, 
our insurance company that has been in run-off since 2012, and expenses associated with our corporate holding company. 

The increase in net expense for 2022 is primarily attributable to a $4.8 million increase in the fair value of previously-granted awards 
to PWSC employees that are accounted for on a fair value basis and an increase in the fair value of the Ravix contingent consideration 
liability of $1.2 million, partially offset by lower general and administrative expense incurred by the holding company during 2022 
compared to 2021. 

Amortization of Intangible Assets 

Amortization of intangible assets was $6.1 million in 2022 compared to $4.8 million in 2021. 

The  higher  amortization  expense  for 2022  is  related  to  amortization  of  intangible  assets  recorded  in  conjunction  with  the 
Company’s acquisitions  of Ravix  effective  October  1,  2021,  CSuite  effective  November  1,  2022  and  SNS  effective  November  18, 
2022.  During 2022, the Company recorded $1.1 million, $0.3 million and $0.3 million, respectively, of amortization expense related to 
the intangible assets identified as part of the acquisitions of Ravix, CSuite and SNS. 

See Note 4, “Acquisitions,” to the Consolidated Financial Statements for further details on the Company’s acquisitions of Ravix, CSuite 
and SNS. 

Loss on Change in Fair Value of Debt  

The loss on change in fair value of debt amounted to $4.9 million in 2022 compared to $3.2 million in 2021. The loss for 2022 reflects 
an increase in the fair value of the subordinated debt resulting primarily from changes in interest rates used (not related to instrument-
specific credit risk). The following summarizes the impacts: 

Impact of Rate Change on Fair Value 

2022 Result 

2021 Result 

Libor: 

increase causes fair value to increase; decrease causes fair value to decrease    

Increase to fair value 

   Increase to fair value 

Risk free rate: 

increase causes fair value to decrease; decrease causes fair value to increase     Decrease to fair value     Decrease to fair value 

See “Debt” section below for further information. 

Gain on Disposal of Subsidiary 

On July 29, 2022, the Company sold its 80% majority-owned subsidiary, PWSC.  As a result of the sale, the Company recognized a net 
gain on disposal of $37.9 million during the third quarter of 2022.  The sale of PWSC did not represent a strategic shift that would have 
a major effect on the Company’s operations or financial results; therefore, PWSC is not presented within discontinued operations. 

See Note  5,  “Disposal  and  Discontinued  Operations,”  to  the  Consolidated  Financial  Statements,  for  further  discussion  of  the 
PWSC disposal. 

Gain on Extinguishment of Debt not Allocated to Segments 

During 2021, gain on extinguishment of debt not allocated to segments consists of a $0.3 million gain (recorded in the first quarter of 
2021)  on  forgiveness  of  the  balance  of  the  holding  company’s  loan  obtained  through  the  PPP of  the  Coronavirus  Aid,  Relief,  and 
Economic Security (“CARES”) Act.  See Note 12, “Debt,” to the Consolidated Financial Statements, for further discussion. 

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KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

Income Tax Expense (Benefit) 

Income tax expense for 2022 was $4.8 million compared to income tax benefit of $3.9 million in 2021. The 2022 and 2021 income tax 
expense (benefit) is primarily related to: 

•  An income tax expense of $1.0 million and an income tax benefit $0.4 million in 2022 and 2021, respectively, for the partial 
release  of  the  Company’s  deferred  income  tax  valuation  allowance  associated  with  business  interest  expense  with  an 
indefinite life; 

•  An income tax benefit of $0.2 million in 2022 for the partial release of the Company’s deferred tax valuation allowance related 
to the change in future income assumptions and $4.1 million in 2021 for the partial release of the Company’s deferred income 
tax valuation allowance related to its acquisitions of PWI and Ravix; 

•  An income tax expense of $0.1 million and $0.2 million in 2022 and 2021, respectively, relating to a change in indefinite life 

deferred income tax liabilities; and 

•  An income tax expense of $3.9 million and $0.4 million in 2022 and 2021, respectively, for state income taxes. 

See Note 15, “Income Taxes,” to the Consolidated Financial Statements, for additional detail of the income tax benefit recorded for the 
years ended December 31, 2022 and December 31, 2021, respectively. 

INVESTMENTS 

Portfolio Composition 

The following is an overview of how we account for our various investments: 

• 

Investments in fixed maturities are classified as available-for-sale and are reported at fair value. 

•  Equity investments are reported at fair value. 

•  Limited liability investments are accounted for under the equity method of accounting. The most recently available financial 
statements of the limited liability investments are used in applying the equity method. The difference between the end of the 
reporting period of the limited liability investments and that of the Company is no more than three months. 

•  Limited liability investments, at fair value represent the underlying investments of the Company’s consolidated entities Net 
Lease and Argo Holdings. The difference between the end of the reporting period of the limited liability investments, at fair 
value and that of the Company is no more than three months. 

• 

Investments  in  private  companies  consist  of:  convertible  preferred  stocks  and  notes  in  privately  owned  companies;  and 
investments in limited liability companies in which the Company’s interests are deemed minor. These investments do not have 
readily determinable fair values and, therefore, are reported at cost, adjusted for observable price changes and impairments. 

•  Real estate investments are reported at fair value, which consisted of Flowers. 

•  Other investments include collateral loans and are reported at their unpaid principal balance. 

• 

Short-term investments, which consist of investments with original maturities between three months and one year, are reported 
at cost, which approximates fair value. 

At December 31, 2022, we held cash and cash equivalents, restricted cash and investments with a carrying value of $134.2 million.  Our 
U.S. operations typically invest in U.S. dollar-denominated instruments to mitigate their exposure to currency rate fluctuations. 

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KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

Table  2  below  summarizes  the  carrying  value  of  investments,  including  cash  and  cash  equivalents  and  restricted  cash,  at  the 
dates indicated. 

TABLE 2 Carrying value of investments, including cash and cash equivalents and restricted cash 
As of December 31 (in thousands of dollars, except for percentages) 

Type of investment 
Fixed maturities: 

U.S. government, government agencies and authorities 
States, municipalities and political subdivisions 
Mortgage-backed 
Asset-backed 
Corporate 

Total fixed maturities 
Equity investments: 
Common stock 
Warrants 

Total equity investments 

Limited liability investments 
Limited liability investments, at fair value 
Investments in private companies 
Real estate investments 
Other investments 
Short-term investments 

Total investments 
Cash and cash equivalents 
Restricted cash 
Total 

Other-Than-Temporary Impairment 

2022      % of Total      

2021      % of Total   

15,080       
2,232       
8,412       
1,610       
10,257       
37,591       

153       
—       
153       
983       
17,059       
790       
—       
201       
157       
56,934       
64,168       
13,064       
134,166       

11.2 %     
1.7 %     
6.3 %     
1.2 %     
7.6 %     
28.0 %     

0.1 %     
— %     
0.1 %     
0.7 %     
12.7 %     
0.6 %     
— %     
0.2 %     
0.1 %     
42.4 %     
47.9 %     
9.7 %     
100.0 %     

16,223       
1,878       
7,629       
445       
9,491       
35,666       

171       
8       
179       
1,901       
18,826       
790       
10,662       
256       
157       
68,437       
10,084       
17,257       
95,778       

16.9 % 
2.0 % 
8.0 % 
0.5 % 
9.9 % 
37.2 % 

0.2 % 
0.0 % 
0.2 % 
2.0 % 
19.7 % 
0.8 % 
11.1 % 
0.3 % 
0.2 % 
71.5 % 
10.5 % 
18.0 % 
100.0 % 

The Company performs a quarterly analysis of its investments to determine if declines in market value are other-than-temporary. Further 
information regarding our detailed analysis and factors considered in establishing an other-than-temporary impairment on an investment 
is discussed within the “Significant Accounting Policies and Critical Estimates” section of MD&A. 

As  a  result  of  the  analysis  performed,  the  Company  recorded write  downs  for  other-than-temporary  impairment  related  to limited 
liability investments, at fair value of less than $0.1 million and $0.1 million for the years ended December 31, 2022 and December 31, 
2021,  respectively,  which  are  included  in  (loss)  gain  on  change  in  fair  value  of  limited  liability  investments,  at  fair  value  in  the 
consolidated statements of operations. 

There were no write-downs recorded for other-than-temporary impairments related to available-for sale investments, limited liability 
investments, investments in private companies and other investments for the years ended December 31, 2022 and December 31, 2021. 

The length of time a fixed maturity investment may be held in an unrealized loss position may vary based on the opinion of the investment 
manager  and  their  respective  analyses  related  to  valuation  and  to  the  various  credit  risks  that  may  prevent  us  from  recapturing  the 
principal investment. In the case of a fixed maturity investment where the investment manager determines that there is little or no risk 
of default prior to the maturity of a holding, we would elect to hold the investment in an unrealized loss position until the price recovers 
or  the  investment  matures.  In  situations  where  facts  emerge  that  might  increase  the  risk  associated  with  recapture  of  principal,  the 
Company may elect to sell a fixed maturity investment at a loss. 

At  December  31,  2022  and  December  31,  2021,  the  gross  unrealized  losses  for  fixed  maturities  amounted  to $2.5 million 
and $0.3 million, and there were no unrealized losses attributable to non-investment grade fixed maturities. At each of December 31, 
2022 and December 31, 2021, all unrealized losses on individual investments were considered temporary. 

DEBT 

See Note 12 , “ Debt,” to the Consolidated Financial Statements for further details to those provided below. 

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KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

Bank Loans 

In 2019, the Company formed Kingsway Warranty Holdings LLC (“KWH”), whose subsidiaries at the time included IWS, Geminus 
and Trinity.  As part of the acquisition of PWI on December 1, 2020, PWI became a wholly owned subsidiary of KWH, which borrowed 
a principal amount of $25.7 million from a bank to finance its acquisition of PWI and to fully repay the prior outstanding loan at KWH 
(the “2020 KWH Loan”). The 2020 KWH Loan had an annual interest rate equal to LIBOR, having a floor of 0.75%, plus 3.00%.  During 
the second quarter of 2022, the 2020 KWH Loan was amended to change the annual interest rate to be equal to the Secured Overnight 
Financing Rate (“SOFR”), having a floor of 0.75%, plus spreads ranging from 2.62% to 3.12%.  At December 31, 2022, the interest rate 
was 6.96%. The 2020 KWH Loan is carried in the consolidated balance sheets at its amortized cost, which reflects the pay-down of 
principal, as well as the amortization of the debt discount and issuance costs using the effective interest rate method. The 2020 KWH 
Loan matures on December 1, 2025.  

The 2020 KWH Loan contains a number of covenants, including, but not limited to, a leverage ratio, a fixed charge ratio and limits on 
annual capital expenditures, all of which are as defined in and calculated pursuant to the 2020 KWH Loan that, among other things, 
restrict KWH’s ability to incur additional indebtedness, create liens, make dividends and distributions, engage in mergers, acquisitions 
and consolidations, make certain payments and investments and dispose of certain assets. 

On  February  28,  2023,  KWH  entered  into  a  second  amendment  to  the  2020  KWH  Loan  (the  “KWH  DDTL”)  that  provides  for  an 
additional delayed draw term loan in the principal amount of up to $10 million, with a maturity date of December 1, 2025.  All or any 
portion of the KWH DDTL, subject to a $2 million minimum draw amount, may be requested at any time through February 27, 2024. 
The proceeds are evidenced by an intercompany loan and guarantee between KAI and KWH.  Proceeds from certain assets dispositions, 
as defined, may be required to be used to repay outstanding draws under the DDTL.  The principal amount shall be repaid in quarterly 
installments in an amount equal to 3.75% of the original amount of the drawn DDTL. The KWH DDTL also increases the senior cash 
flow leverage ratio maximum permissible for certain periods. 

As part of the acquisition of Ravix on October 1, 2021, Ravix became a wholly owned subsidiary of Ravix Acquisition LLC (“Ravix 
LLC”), and together they borrowed from a bank a principal amount of $6.0 million in the form of a term loan, and established a $1.0 
million revolver to finance the acquisition of Ravix (together, the “2021 Ravix Loan”).  The 2021 Ravix Loan has an annual interest 
rate equal to the greater of the Prime Rate plus 0.5%, or 3.75% (current rate of 8.00%) and is carried in the consolidated balance sheets 
at its amortized cost, which reflects the monthly pay-down of principal as well as the amortization of the debt discount and issuance 
costs using the effective interest rate method. The term loan matures on October 1, 2027.  

Subsequent to the acquisition of CSuite on November 1, 2022, CSuite became a wholly owned subsidiary of Ravix LLC.  As a result of 
the acquisition of CSuite, on November 16, 2022, the Ravix Loan was amended to (1) include CSuite as a borrower; (2) borrow an 
additional principal amount of $6.0 million in the form of a supplemental term loan (the “2022 Ravix Loan”); and (3) amend the maturity 
date and interest rate of the $1.0 million revolver (the “2022 Revolver”).  The 2022 Ravix Loan matures on November 16, 2028 and has 
an annual interest rate equal to the Prime Rate plus 0.75% (current rate of 8.25%) and is carried in the consolidated balance sheet at 
December  31,  2022 at  its  amortized  cost,  which  reflects  the  monthly  pay-down  of  principal.  The  2022  Revolver  matures  on 
November 16, 2024 and has an annual interest rate equal to the Prime Rate plus 0.50%.  

The 2021 Ravix Loan and 2022 Ravix Loan contain a number of covenants, including, but not limited to, a leverage ratio and a fixed 
charge ratio, all of which are as defined in and calculated pursuant to the 2021 Ravix Loan and 2022 Ravix Loan that, among other 
things, restrict Ravix and CSuite’s ability to incur additional indebtedness, create liens, make dividends and distributions, engage in 
mergers, acquisitions and consolidations, make certain payments and investments and dispose of certain assets. 

As part of the asset acquisition of SNS on November 18, 2022, the Company formed Secure Nursing Service LLC, who became a wholly 
owned subsidiary of Pegasus Acquirer Holdings LLC (“Pegasus LLC”), and together they borrowed from a bank a principal amount of 
$6.5 million in the form of a term loan, and established a $1.0 million revolver to finance the acquisition of SNS (together, the “SNS 
Loan”).  The SNS Loan has an annual interest rate equal to the greater of the Prime Rate plus 0.5%, or 5.00% (current rate of 8.00%) 
and is carried in the consolidated balance sheet at December 31, 2022 at its amortized cost, which reflects the monthly amortization of 
the debt discount and issuance costs using the effective interest rate method. The term loan matures on November 18, 2028 and revolver 
matures on November 18, 2023.  

The SNS Loan contains a number of covenants, including, but not limited to, a leverage ratio and a fixed charge ratio and limits on 
annual capital expenditures, all of which are as defined in and calculated pursuant to the SNS Loan that, among other things, restrict 
SNS’s  ability  to  incur  additional  indebtedness,  create  liens,  make  dividends  and  distributions,  engage  in  mergers,  acquisitions  and 
consolidations, make certain payments and investments and dispose of certain assets. 

34 

KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

Notes Payable 

On January 5, 2015, Flower Portfolio 001, LLC assumed a $9.2 million mortgage in conjunction with the purchase of investment real 
estate properties (“the Flower Note”). The Flower Note was scheduled to mature on December 10, 2031 and had a fixed interest rate of 
4.81%. On September 29, 2022, Flower sold its investment real estate properties and used a portion of the sales proceeds to repay the 
unpaid principal balance of the Flower Note.  At December 31, 2021, the Flower Note is carried in the consolidated balance sheet at its 
unpaid principal balance. 

In April 2020, certain subsidiaries of the Company received loan proceeds under the PPP, totaling $2.9 million with a stated annual 
interest rate of 1.00%. The PPP, established as part of the CARES Act and administered by the U.S. Small Business Administration (the 
“SBA”), provides for loans to qualifying businesses for amounts up to 2.5 times of the average monthly payroll costs (as defined for 
purposes of the PPP) of the qualifying business. The loans and accrued interest are forgivable as long as the borrower uses the loan 
proceeds for eligible purposes, including payroll, costs, rent and utilities, during the twenty-four week period following the borrower’s 
receipt of the loan and maintains its payroll levels and employee headcount. The amount of loan forgiveness will be reduced if the 
borrower reduces its employee headcount below its average employee headcount during a benchmark period or significantly reduces 
salaries for certain employees during the covered period. 

The Company used the entire loan amount for qualifying expenses. The U.S. Department of the Treasury has announced that it will 
conduct audits for PPP loans that exceed $2.0 million. If we were to be audited and receive an adverse outcome in such an audit, we 
could be required to return the full amount of the PPP Loan and may potentially be subject to civil and criminal fines and penalties. 

On December 21, 2020 the SBA approved the forgiveness of the full amount of one of the five PPP loans, which included principal and 
interest of $0.4 million. In January 2021 and March 2021, the SBA provided the Company with notices of forgiveness of the full amount 
of the remaining four loans. The forgiveness in the first quarter of 2021 included total principal and interest of $2.5 million.  

Subordinated Debt 

Between  December  4,  2002  and  December  16,  2003,  six  subsidiary  trusts  of  the  Company  issued  $90.5  million  of  30-year  capital 
securities to third parties in separate private transactions. In each instance, a corresponding floating rate junior subordinated deferrable 
interest debenture was then issued by Kingsway America Inc. to the trust in exchange for the proceeds from the private sale. The floating 
rate debentures bear interest at the rate of LIBOR, plus spreads ranging from 3.85% to 4.20%. The Company has the right to call each 
of these securities at par value any time after five years from their issuance until their maturity. 

During the third quarter of 2018, the Company gave notice to its Trust Preferred trustees of its intention to exercise its voluntary right 
to defer interest payments for up to 20 quarters, pursuant to the contractual terms of its outstanding Trust Preferred indentures, which 
permit interest deferral. This action does not constitute a default under the Company’s Trust Preferred indentures or any of its other debt 
indentures. At December 31, 2022 and December 31, 2021, deferred interest payable of $25.5 million and $18.7 million, respectively, 
is included in accrued expenses and other liabilities in the consolidated balance sheets. 

On August 2, 2022, the Company entered into an agreement with a holder of four of the trust preferred debt instruments (“TruPs”) that 
gives  the  Company  the  option  to  repurchase  up  to  100%  of  the  holder’s  principal  and  deferred  interest  for  a  purchase  price  equal 
to 63% of the outstanding principal and deferred interest.  Originally, the agreement called for a repurchase at 63%, which escalated to 
63.75% once the September 26, 2022 agreement (described below) was signed.  The Company has agreed that any repurchase made 
will be for no less than 50% of the TruPs held by the holder. 

Until the earlier of (i) the date that all four of the preferred debt instruments have been repurchased and (ii) the nine month anniversary 
of the agreement (“May Termination Date”), all interest on the four preferred debt instruments will continue to accrue.  However, with 
respect to TruPs that are repurchased prior to the May Termination Date, the amount of interest accrued during the term of the agreement 
will be treated as an offset and reduce the repurchase price for such TruPs.  The Company will have no obligation to pay any such 
accrued interest with respect to any of the TruPs that are repurchased prior to the May Termination Date. 

The Company paid approximately $2.0 million to the holder for this option and the Company has until the May Termination Date to 
execute the repurchases.  If the Company repurchases less than $30.0 million of principal and deferred interest, or fails to purchase any 
principal or deferred interest within one year, then the $2.0 million paid is forfeited.  If the Company repurchases an amount equal to or 
great than $30.0 million, then the $2.0 million paid would be applied to such repurchases. 

On September 20, 2022, the Company entered into an additional agreement with the same party to the August 2, 2022 agreement that 
gives the Company the option to repurchase up to 100% of the holder’s principal and deferred interest for 63.75% of the outstanding 
principal and deferred interest relating to a portion of a fifth TruPs held. The September 20, 2022 agreement is subject to the same terms 
and conditions as the August 2, 2022 and no additional consideration was paid. 

35 

KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

On September 26, 2022, the Company entered into an agreement with a holder of a portion of one of the TruPs that gives the Company 
the option to repurchase up to 100% of the holder’s principal and deferred interest for a purchase price equal to 63% of the outstanding 
principal and deferred interest.  

Until the earlier of (i) the date that all of the preferred debt instrument has been repurchased and (ii) the May Termination Date, all 
interest on the preferred debt instrument will continue to accrue.  However, with respect to TruPs that are repurchased prior to the May 
Termination Date, the amount of interest accrued during the term of the agreement will be treated as an offset and reduce the repurchase 
price  for  such  TruPs.   The  Company  will  have  no  obligation  to  pay  any  such  accrued  interest  with  respect  to  the  TruPs that  are 
repurchased prior to the May Termination Date. 

The Company paid approximately $0.3 million to the holder for this option and the Company has until the May Termination Date to execute 
the repurchase.  If the Company fails to purchase any principal or deferred interest before the May Termination Date, then the $0.3 million 
paid is forfeited.  If the Company repurchases any of the TruPs, then the $0.3 million paid would be applied to any repurchases. 

The Company continues to accrue interest on all six of the TruPs. 

In February 2023, the Company entered into amendments to the repurchase agreements described above that would give the Company 
an additional discount on the total repurchase price if the Company effected a 100% repurchase on or before March 15, 2023.  On 
March 2, 2023, the Company gave notice to the holders that it intends to exercise its options to repurchase 100% of the principal no 
later than March 15, 2023.  The total amount to be paid will be $56.5 million, which includes a credit for the $2.3 million that the 
Company previously paid at the time of entering into the repurchase agreements. As a result, the Company will have repurchased $75.5 
million of principal and $21.2 million of deferred interest (valued as of December 31, 2022). The Company intends to use currently 
available funds from working capital to fund the repurchases. 

In order to execute the repurchase, the Company will have to pay an estimated $4.7 million of deferred interest to the remaining trust 
preferred debt instrument for which the Company did not have the right to repurchase. After the repurchase is completed, the Company 
will continue to have $15 million of principal outstanding related to remaining trust preferred debt instrument. 

The agreements governing our subordinated debt contain a number of covenants that, among other things, restrict the Company’s ability 
to  incur  additional  indebtedness,  make  dividends  and  distributions,  and  make  certain  payments  in  respect  of  the  Company’s 
outstanding securities. 

The Company’s subordinated debt is measured and reported at fair value. At December 31, 2022, the carrying value of the subordinated 
debt is $67.8 million. The fair value of the subordinated debt is calculated using a model based on significant market observable inputs 
and inputs developed by a third-party. For a description of the market observable inputs and inputs developed by a third-party used in 
determining fair value of debt, see Note 23, “Fair Value of Financial Instruments,” to the Consolidated Financial Statements. 

During the year ended December 31, 2022, the market observable swap rates changed, and the Company experienced a decrease in the 
credit  spread  assumption  developed  by  the  third-party.  Changes  in  the  market  observable  swap  rates  affect  the  fair  value  model  in 
different ways. An increase in the LIBOR swap rates has the effect of increasing the fair value of the Company’s subordinated debt 
while an increase in the risk-free swap rates has the effect of decreasing the fair value. The increase in the credit spread assumption has 
the effect of decreasing the fair value of the Company’s subordinated debt while a decrease in the credit spread assumption has the effect 
of increasing the fair value. The other primary variable affecting the fair value of debt calculation is the passage of time, which will 
always have the effect of increasing the fair value of debt. The changes to the credit spread and swap rate variables during 2022, along 
with  the  passage  of  time,  contributed  to  the $6.8 million  increase  in  fair  value  of  the  Company’s  subordinated  debt  between 
December 31, 2021 and December 31, 2022. 

Of  the $6.8 million  increase  in  fair  value  of  the  Company’s  subordinated  debt  between  December  31,  2021  and  December  31, 
2022, $1.9 million  is  reported  as  an  increase  in  fair  value  of  debt  attributable  to  instrument-specific  credit  risk  in  the  Company’s 
consolidated  statements  of  comprehensive  income  (loss)  and $4.9 million  is  reported  as  loss  on  change  in  fair  value  of  debt  in  the 
Company’s consolidated statements of operations. 

Though changes in the market observable swap rates will continue to introduce some volatility each quarter to the Company’s reported 
gain or loss on change in fair value of debt, changes in the credit spread assumption developed by the third party does not introduce 
volatility to the Company’s consolidated statements of operations. The fair value of the Company’s subordinated debt will eventually 
equal  the  principal  value,  totaling  $90.5  million,  of  the  subordinated  debt  by  the  time  of  the  stated  redemption  date  of  each  trust, 
beginning with the trust maturing on December 4, 2032 and continuing through January 8, 2034, the redemption date of the last of the 
Company’s outstanding trusts. 

36 

KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

LIQUIDITY AND CAPITAL RESOURCES  

The purpose of liquidity management is to ensure there is sufficient cash to meet all financial commitments and obligations as they fall 
due.  The  liquidity  requirements  of  the  Company  and  its  subsidiaries  have  historically  been  met  primarily  by  funds  generated  from 
operations,  capital  raising,  disposal  of  subsidiaries,  investment  maturities  and  investment  income,  and  other  returns  received  on 
investments and from the sale of investments. 

A significant portion of the cash provided by our Extended Warranty companies is required to be placed into restricted trust accounts, 
as determined by the insurers who back-up our service contracts, in order to fund future expected claims.  On a periodic basis (quarterly 
or annually), we may be required to contribute more into the restricted accounts or we may be permitted to draw additional funds from 
the  restricted  accounts,  dependent  upon  actuarial  analyses  performed  by  the  insurers  regarding  sufficiency  of  funds  to  cover  future 
expected claims.  A substantial portion of the restricted trust accounts are invested in fixed maturities and other instruments that have 
durations similar to the expected future claim projections. 

Cash provided from these sources is used primarily for warranty expenses, business service expenses, debt servicing, acquisitions and 
operating expenses of the holding company.  

The Company’s Extended Warranty and Kingsway Search Xcelerator subsidiaries fund their obligations primarily through service fee 
and commission revenue.  

Cash Flows from Continuing Operations 

During 2022, the Company reported $2.6 million of net cash used in operating activities from continuing operations, primarily due to: 

•  The sale of PWSC, which generated cash flows of $1.8 million through the date of the sale in 2022, compared to $2.8 million 

for 2021; 

•  A $0.4 million reduction in cash flows from the remaining Extended Warranty companies; 

•  Outflows at the holding company related to the TruPs repurchase option ($2.3 million); all of which were partially offset by; 

•  Continued cost containment initiatives at the holding company regarding ongoing expenses; and  

• 

Increases in cash flows from the KSX companies, due to the inclusion of Ravix for the full twelve months in 2022 and the 
acquisitions of CSuite and SNS. 

During 2021, the Company reported $6.5 million of net cash provided by operating activities from continuing operations, primarily due 
to  cash  inflows  generated  by  the  Extended  Warranty  segment  (which  includes  PWI  for  12  months  in  2021)  and  cost  containment 
initiatives at the holding company. 

During  2022,  the  net  cash  provided  by  investing  activities from  continuing  operations  was $58.1  million.  This  source  of  cash  was 
primarily attributed to: 

•  Net cash proceeds received, net of cash disposed of from the sale of PWSC, of $35.2 million; 

•  Net cash proceeds received from the sale of the CMC Real Property of $26.4 million; 

•  Cash proceeds received from the sale of real estate investments of $12.2 million; 

•  The acquisitions of CSuite and SNS in 2022, which totaled $13.7 million, net of cash acquired; and 

• 

Purchases  of  fixed  maturities  in  excess  of  proceeds  from  limited  liability  investments  and  from  sales  and  maturities  of 
fixed maturities. 

During  2021, the  net  cash  used  in  investing  activities from  continuing  operations  was $9.0  million.  This  use of  cash  was  primarily 
attributed to: 

• 

Purchases of fixed maturities in excess of proceeds from sales and maturities of fixed maturities of $15.6 million; 

•  The acquisitions of Ravix and RoeCo in 2021, which totaled $12.6 million, net of cash acquired; 

37 

  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

•  Distributions received (reducing the use of cash) by Net Lease from two of its limited liability investment companies of $16.3 

million; and  

• 

Proceeds received (reducing the use of cash) from the Company’s limited liability investments. 

During 2022, the net cash used in financing activities from continuing operations was $5.6 million, primarily attributed to: 

• 

Principal repayments: on bank loans of $5.2 million, notes payable of $6.4 million, which relates to the repayment of the Flower 
Note; 

•  Distributions to noncontrolling interest holders of $6.0 million; and 

•  Net proceeds (reducing the use of cash) from bank loans of $12.7 million related to the 2022 Ravix Loan and the SNS Loan, 

and proceeds from the exercise of warrants of $0.5 million. 

During 2021, the net cash used in financing activities from continuing operations was $9.3 million, primarily attributed to: 

• 

Principal  repayments:  on  bank  loans  of  $4.9  million,  notes  payable  of  $9.5  million,  of  which  $9.0  million  relates  to  the 
repayment of Net Lease’s $9.0 million mezzanine loan and $0.5 million relating to principal paydowns on the Flower Note; 

•  Distributions to noncontrolling interest holders of $2.4 million; and 

•  Net proceeds  (reducing  the  use  of  cash)  from  bank  loans  of $6.2  million  related  to  the Ravix  Loan and  proceeds  from  the 

exercise of warrants of $1.8 million. 

Holding Company Liquidity 

The liquidity of the holding company is managed separately from its subsidiaries. The obligations of the holding company primarily 
consist of holding company operating expenses; transaction-related expenses; investments; and any other extraordinary demands on the 
holding company. 

Pursuant to satisfying the covenants under the 2020 KWH Loan, distributions to the holding company in an aggregate amount not to 
exceed $1.5 million in any 12-month period are permitted.  Also, beginning in 2022, the holding company is permitted to receive a 
portion of the excess cash flow (as defined in the 2020 KWH Loan document) generated by the KWH Subs in the previous year.  In 
2022, the Company was entitled to 50% of the excess cash flow with the other 50% used to pay down the 2020 KWH Loan.  During 
2022, the Company received $1.7 million and in March 2022 paid down the KWH 2020 Loan by $1.7 million.  

The amount of excess cash flow the Company is entitled to retain is dependent upon the leverage ratio (as defined in the 2020 KWH 
Loan document): 

If leverage ratio is 
Greater than 1.75:1.00 
Less than 1.75:1.00 but greater than 
0.75:1.00 
Less than 0.75:1.0 

Percent of excess cash flow 
retained by the Company 
50% 

75% 

100% 

The Company anticipates that in 2023 it will be entitled to receive 75% of the 2022 excess cash flow. 

On October 1, 2021, the Company closed on the acquisition of Ravix. Related to the Ravix acquisition, the Company secured the 2021 
Ravix Loan with Ravix and Ravix LLC as borrowers under the 2021 Ravix Loan.  On November 1, 2022, the Company closed on the 
acquisition  of  CSuite.  Related  to  the  CSuite acquisition,  the  Company  secured  the  2022  Ravix Loan  with  CSuite,  Ravix  and  Ravix 
LLC as borrowers under the 2022 Ravix Loan. Pursuant to the covenants under the 2021 Ravix Loan and the 2022 Ravix Loan, Ravix 
and CSuite are permitted to make distributions to the holding company so long as doing such would not cause non-compliance with the 
various covenants outlined within the 2021 Ravix Loan and 2022 Ravix Loan. 

On November 18, 2022, the Company closed on the acquisition of SNS. Related to the SNS acquisition, the Company secured the SNS 
Loan with SNS and Pegasus LLC as borrowers under the SNS Loan. Pursuant to the covenants under the SNS Loan, SNS is not permitted 
to make distributions to the holding company without the consent of the lender. 

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KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

On  October  18,  2018,  the  Company  completed  the  previously  announced  sale  of its  non-standard  automobile  insurance  companies 
Mendota Insurance Company, Mendakota Insurance Company and Mendakota Casualty Company (collectively “Mendota”).  As part 
of the transaction, the Company will indemnify the buyer for any loss and loss adjustment expenses with respect to open claims in excess 
of Mendota’s carried unpaid loss and loss adjustment expenses at June 30, 2018 related to the open claims. The maximum obligation to 
the Company with respect to the open claims is $2.5 million. Per the purchase agreement, a security interest on the Company’s equity 
interest in its consolidated subsidiary, Net Lease, as well as any distributions to the Company from Net Lease, was to be collateral for 
the Company’s payment of obligations with respect to the open claims. 

During the third quarter of 2021, the purchasers of Mendota and the Company agreed to release the Company’s equity interest in Net 
Lease as collateral and allow Net Lease to make distributions to the Company.  In exchange, the Company agreed to deposit $2.0 million 
into an escrow account and advance $0.5 million to the purchaser of Mendota to satisfy the Company’s payment obligation with respect 
to the open claims. 

During  the  third  quarter  of  2022,  the  buyer  provided  to  the  Company  an  analysis  of  the  claims  development  that  indicated  that 
the Company’s potential exposure with respect to the open claims was at the maximum obligation amount.  Previous communications 
from the buyer noted no such development.  As a result of the newly provided information, the Company recorded a liability of $2.5 
million during the third quarter of 2022, which is included in accrued expenses and other liabilities in the consolidated balance sheet at 
December  31,  2022  and loss  on  disposal  of  discontinued  operations  in  the consolidated  statement  of  operations  for  the  year  ended 
December 31, 2022.  There were no payments made by the Company related to the open claims during the years ended December 31, 
2022 and December 31, 2021.  During the first quarter of 2023, the $2.0 million that had been previously deposited into an escrow 
account was released and remitted to the buyer to satisfy the Company’s payment with respect to the open claims.   

The holding company’s liquidity, defined as the amount of cash in the bank accounts of Kingsway Financial Services Inc. and Kingsway 
America Inc., was $48.9 million and $2.2 million at December 31, 2022 and December 31, 2021, respectively, which excludes future 
actions available to the holding company that could be taken to generate liquidity.  The holding company cash amounts are reflected in 
the cash and cash equivalents of $64.2 million and $10.1 million reported at December 31, 2022 and December 31, 2021, respectively, 
on the Company’s consolidated balance sheets.  The significant increase is primarily due to the sale of PWSC and the sale of the CMC 
railyard in 2022. 

In addition to its collections from subsidiaries and holding company expenditures, the Company anticipates the following cash inflows 
and outflows over the next twelve months: 

•  Inflows: 

  •  Distributions from Net Lease of $8.3 million, from the sale of the last commercial real estate property in February 2023 

•  $3.7 million from the exercise of 0.7 million warrants from January 1 through February 28, 2023 

•  $1.5 million distribution from Amigo, given that as of early March 2023 it was no longer a regulated insurance company 

 •  Outflows: 

•  $56.5  million  to  repurchase  the  trust  preferred  debt  instruments  (aka  subordinate  debt)  for  which  it  has  the  option  to 
repurchase, which outflow is expected no later than March 15, 2023 (see Note 11, “Derivatives,” and Note 26, “Subsequent 
Events,” to the Consolidated Financial Statements) 

•  $4.7 million of deferred interest to the remaining trust preferred debt instrument for which the Company did not have the right 
to repurchase (see Note 26, “Subsequent Events,” to the Consolidated Financial Statements); the Company would have the 
ability to defer interest payments for up to 20 quarters on the remaining trust preferred debt instrument, if it so elected 

•  $6.1 million required to redeem the Class A Preferred Shares; however, based on discussions with the holders of the Class A 
Preferred Shares, the Company anticipates that 100% of the Class A Preferred Shares would be converted and, in that case, 
there  would  be  no  cash  outlay  by  the  Company  (see  Note  19,  “Redeemable  Class  A  Preferred  Stock,” and  Note  26, 
“Subsequent Events,” to the Consolidated Financial Statements)  

The  Company  notes  there  are  outstanding  warrants  that  expire  in  September  2023  (see  Note  20,  “Shareholders’  Equity,” to  the 
Consolidated Financial Statements) and, if all outstanding warrants were exercised, the Company would receive an additional $18.7 

39 

  
  
  
  
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Management’s Discussion and Analysis 

million.  The Company also notes that it has an additional $10 million available from the second amendment to the 2020 KWH Loan 
(see Note 12, “Debt,” and Note 26, “Subsequent Events,” to the Consolidated Financial Statements), that is available to be drawn. 

Based  on  the  Company’s  current  business  plan  and  revenue  prospects,  existing  cash,  cash  equivalents,  investment  balances  and 
anticipated cash flows from operations are expected to be sufficient to meet the Company’s working capital and operating expenditure 
requirements, including the cash that may be required to redeem the Preferred Shares, repurchase its trust preferred securities and pay 
deferred interest on its trust preferred securities, for the next twelve months. However, the Company’s assessment could also be affected 
by various risks and uncertainties, including, but not limited to, the developing macro-economic environment. 

Regulatory Capital 

Kingsway Reinsurance Corporation (“Kingsway Re”), our reinsurance subsidiary domiciled in Barbados, is required by the regulator in 
Barbados  to  maintain  minimum  statutory  capital  of  $125,000.  Kingsway  Re  is  currently  operating  with  statutory  capital  near  the 
regulatory minimum, requiring us to periodically contribute capital to fund operating expenses. Kingsway Re incurs operating expenses 
of approximately $0.1 million per year. As of December 31, 2022, the capital maintained by Kingsway Re was in excess of the regulatory 
capital requirements in Barbados. 

CONTRACTUAL OBLIGATIONS 

Table 3 summarizes cash disbursements related to the Company’s contractual obligations projected by period, including debt maturities, 
interest payments on outstanding debt and future minimum payments under operating leases. Interest payments on outstanding debt in 
Table 3 related to the subordinated debt, the 2020 KWH Loan, the 2021 Ravix Loan, the 2022 Ravix Loan and the SNS Loan assume 
the  variable  rates remain constant  throughout  the  projection  period.  Also,  interest  payments  on  outstanding  debt  reflect  the  interest 
deferral described in the “Subordinated Debt” section above. 

TABLE 3 Cash payments related to contractual obligations projected by period  
As of December 31, 2022 (in thousands of dollars) 

Bank loans 
Subordinated debt 
Interest payments on outstanding debt 
Future minimum lease payments 
Total 

2023     
5,413       
—       
36,451       
472       
42,336       

2024     
6,580       
—       
10,461       
356       
17,397       

2025     
12,723       
—       
9,859       
191       
22,773       

2026     
3,750       
—       
9,162       
124       
13,036       

2027      Thereafter     
3,775       
—       
8,832       
59       

Total   
34,808   
2,567       
90,500       
90,500   
41,189        115,954   
1,263   
12,666        134,317        242,525   

61       

Table 3 above does not assume that the Company has repurchased any of its TruPs subordinated debt on or before March 15, 2023, as 
discussed in the “Debt” section above, given the table presents information as of December 31, 2022.  Refer to Note 11, “Derivatives,” 
to the Consolidated Financial Statements for further information regarding the trust preferred debt repurchase option agreements.   

While the Company gave notice on March 1, 2023 of its intent to redeem the Preferred Shares on March 15, 2023, Table 3 above does 
not reflect the $6.1 million that may be paid for the redemption.  See “Holding Company Liquidity” above for further discussion.  Refer 
to  Note  19,  “Redeemable  Class  A  Preferred  Stock,”  to  the  Consolidated  Financial  Statements  for further  information  regarding the 
Preferred Shares. 

40 

  
  
  
    
    
    
    
    
  
KINGSWAY FINANCIAL SERVICES INC. 

Item 7A. Quantitative and Qualitative Disclosures About Market Risk  

We are a smaller reporting company as defined in Rule 12b-2 of the Exchange Act; therefore, pursuant to Regulation S-K, we are not 
required to make disclosures under this Item. 

41 

 
 
KINGSWAY FINANCIAL SERVICES INC. 

Item 8. Financial Statements and Supplementary Data. 

Index to the Consolidated Financial Statements of 

Kingsway Financial Services Inc. 

Report of Independent Registered Public Accounting Firm (PCAOB ID 166) 
Consolidated Balance Sheets at December 31, 2022 and 2021 
Consolidated Statements of Operations for the Years Ended December 31, 2022 and 2021 
Consolidated Statements of Comprehensive Income (Loss) for the Years Ended December 31, 2022 and 2021 
Consolidated Statements of Shareholders’ Equity for the Years Ended December 31, 2022 and 2021 
Consolidated Statements of Cash Flows for the Years Ended December 31, 2022 and 2021 
Notes to the Consolidated Financial Statements 
Note 1 -Business 
Note 2-Summary of Significant Accounting Policies 
Note 3-Recently Issued Accounting Standards 
Note 4-Acquisitions 
Note 5-Disposal and Discontinued Operations 
Note 6-Variable Interest Entities 
Note 7-Investments 
Note 8-Goodwill 
Note 9-Intangible Assets 
Note 10-Property and Equipment 
Note 11-Derivatives 
Note 12-Debt 
Note 13-Leases 
Note 14-Revenue from Contracts with Customers 
Note 15-Income Taxes 
Note 16-Earnings (Loss) Per Share 
Note 17-Stock-Based Compensation 
Note 18-Employee Benefit Plan 
Note 19-Redeemable Class A Preferred Stock 
Note 20-Shareholders’ Equity 
Note 21-Accumulated Other Comprehensive Income 
Note 22-Segmented Information 
Note 23-Fair Value of Financial Instruments 
Note 24-Related Parties 
Note 25-Commitments and Contingent Liabilities 
Note 26-Subsequent Events 

43 
46 
47 
48 
49 
50 
52 
52 
52 
60 
60 
65 
68 
70 
73 
74 
75 
76 
77 
80 
81 
82 
85 
86 
89 
89 
90 
90 
91 
93 
101 
101 
 102 

42 

  
  
 
 
KINGSWAY FINANCIAL SERVICES INC. 

Report of Independent Registered Public Accounting Firm 

To the Stockholders and Board of Directors of Kingsway Financial Services, Inc. 

Opinion on the Financial Statements 

We have audited the accompanying balance sheets of Kingsway Financial Services, Inc. (the “Company”) as of December 31, 2022 and 
December 31, 2021, the related statements of operations, comprehensive income (loss), stockholders’ equity, and cash flows for each 
of the years in the two-year period ended December 31, 2022, and the related notes and schedule (collectively referred to as the “financial 
statements”). In our opinion, the financial statements referred to above present fairly, in all material respects, the financial position of 
the Company as of December 31, 2022 and December 31, 2021, and the results of its operations and its cash flows for each of the years 
in the two-year period ended December 31, 2022, in conformity with accounting principles generally accepted in the United States of 
America. 

Basis for Opinion 

The Company’s management is responsible for these financial statements. 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 Public Company Accounting Oversight 
Board (United States) (“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. 
The Company is not required to have, nor were we engaged to perform, an audit of its internal control over financial reporting. As part 
of our audits, we are required to obtain an understanding of internal control over financial reporting but not for the purpose of expressing 
an opinion on the effectiveness of the Company’s internal control over financial reporting. Accordingly, we express no such opinion. 

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 Matters 

The critical audit matters communicated below are matters arising from the current period audit of the financial statements that were 
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 matters below, providing a separate opinion on the critical audit matters or on the accounts or disclosures to which it relates. 

Revenue Recognition – Refer to Note 2 and Note 14 to the financial statements  

Critical Audit Matter Description 

The Company’s revenue from contracts with customers (ASC 606) relates to extended warranty service fee and commission income, 
which is comprised of multiple revenue streams including: vehicle service agreement fees, guaranteed asset protection commissions, 
maintenance  support  service  fees,  warranty  product  commissions,  homebuilder  warranty  service  fees,  and  homebuilder  warranty 
commissions.   Many  of  the  Company’s  contracts  include  revenue  which  is  generated  from  contracts  with  multiple  performance 
obligations.  Accordingly, the application of revenue recognition policies requires the Company to exercise significant judgement in the 
following areas: 

•  Determination of whether individual services are promises which are considered distinct performance obligations. 

•  Assessing whether the Company is a principal or an agent in providing services to the ultimate customer in the contract. 

•  Assessing variable consideration attributable to each contract and the related estimates of variable consideration, which 
are significant in vehicle service contracts, based on refund rights provided to the customer under vehicle service contracts 
and related business practices. 

43 

  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 

•  Assessing the transaction price including the impact of various dealer and partner incentive and rebate programs which 

are considered contract acquisition costs. 

•  Determining stand-alone selling prices for each distinct service and allocation to each individual performance obligation 

on a relative selling price basis. 

•  Determining the timing of when revenue is recognized for separate performance obligations and whether the performance 

is deemed to occur over time or at a point in time. 

• 

For  performance  obligations  satisfied  over  time,  the  selection  of  an  appropriate  methodology  which  best  depicts  the 
transfer of services to the customer under the contract. 

For these reasons, we identified revenue recognition as a critical audit matter. 

How the Critical Audit Matter was Addressed in the Audit 

The primary procedures we performed to address this critical audit matter included the following, among other procedures: 

•  We obtained an understanding of the processes and internal controls related to each significant revenue generating activity 

within scope of ASC 606. 

•  We  evaluated  the  Company’s  application  of  the  portfolio  approach  to  individual  groups  of  contracts  to  ensure  the 

application was in compliance with ASC 606. 

•  We  tested  the  determination  of  individual  performance  obligations  identified  by  management  to  ensure  distinct 
performance  obligations  identified  were  consistent  with  the  underlying  contracts.  We  also  tested  whether  all  distinct 
performance obligations within each contract were complete and reflected all material promises which are capable of 
being distinct. 

•  We evaluated and tested the key judgements applied by management, including: 

o 

o 

o 

o 

o 

Assessing whether the Company is deemed to be the principal or an agent in delivering services to the customer.  We 
evaluated the key factors to determine whether the Company is responsible for fulfillment of each significant service 
provided to the customer. 

Estimating  variable  consideration,  primarily  related  to  refund  liabilities  on  vehicle  service  contracts,  based  on 
historical patterns and future expectations of customer refund requests. We tested the estimated amount of expected 
refunds including management’s assessment of refund rates on each significant type of warranty contract to assess 
the overall reasonableness of the refund liabilities. 

Determining whether certain incentive payments to dealers and partners were considered customer acquisition costs 
and should be included in the determination of the overall transaction price by examining the underlying program 
agreements and related business practices followed by the Company. 

Estimating  stand-alone  selling  prices  when  multiple  performance  obligations  exist  within  a  contract,  based  on 
management’s internal estimates of cost plus an appropriate margin to support expected selling prices.  We tested 
the related costs expected to be incurred in satisfying the delivery of services at contract commencement and those 
expected to be incurred over the life of the contract which are primarily associated with contract administration 
services.  We  also  tested  the  relative  selling  price  allocation  of  the  contract  price  to  each  separate 
performance obligation. 

Application  of  over  time  recognition  patterns,  including  management’s  estimates  related  to  claims  emergence 
patterns  for  each  separate  group  of  contracts  which  possess  similar  characteristics  that  faithfully  represent  the 
transfer of  services  to  the  customer. We  tested  contracts at  the  warranty  company  subsidiaries  to determine  the 
accuracy and consistency of claim emergence patterns. 

44 

  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 

Trust Preferred Debt Repurchase Options – Refer to Note 2 and Note 11 to the financial statements 

Critical Audit Matter Description 

The Company entered into agreements with multiple holders of trust preferred debt instruments that gives the Company the option to 
repurchase 100% of the holder’s principal and deferred interest at agreed upon prices.  These agreements constitute derivative financial 
instruments are carried at fair value and are required to be revalued each reporting period, with corresponding changes in fair value 
recorded in the consolidated statements of operations. 

The fair value of the Trust Preferred Repurchase Options contracts are estimated using the binomial lattice model.  Key inputs in the 
valuation include credit spread assumptions, interest rate volatility, debt coupon interest rate and time to maturity which in their entirety 
fall under level 3 in the fair value hierarchy.  Significant judgment is required, as the transaction(s) are based upon a hypothetical market 
and the initial deposit consideration paid by the Company does not reflect fair value as the deposit consideration was not based on the 
most advantageous market from a market participant assumption basis. 

For these reasons, we identified the derivative option contracts as a critical audit matter. 

How the Critical Audit Matter Was Addressed in the Audit 

The primary procedures we performed to address this critical audit matter included the following, among other procedures: 

•  We evaluated the Company’s application of the accounting for derivatives to ensure the application was in compliance 

with ASC 815. 

•  We confirmed the terms of the trust preferred debt repurchase options directly with debt holders. 

•  We evaluated the business purpose of the transactions for reasonableness. 

•  We reviewed and tested the methodologies and key assumptions in the valuation analysis provided by management using 

our internal valuation specialists.  In performing these procedures, we considered the following: 

o  Completeness and accuracy of underlying data provided by management 

o 

The nature and basis for valuation adjustments and calculations used by management’s valuation specialists 

o  Reasonableness of the valuation methods and assumptions used by management’s valuation specialists in the analysis 

o 

o 

The sensitivity of significant inputs to the valuation model and their impact on management’s conclusions. 

The probabilities of certain outcomes as selected by management 

•  We tested key inputs to the valuation model, including checking calculations of significant inputs to the valuation model. 

•  We  considered  the  sensitivity  of  key  assumptions  and  performed  sensitivity  analysis  around  the  key  assumptions  in 

evaluating their reasonableness. 

/s/ Plante & Moran PLLC 
We have served as the Company’s auditor since 2020. 
Denver, CO 
March 8, 2023 

45 

  
  
  
  
  
  
  
  
  
  
  
  
  
 
 
KINGSWAY FINANCIAL SERVICES INC. 

Consolidated Balance Sheets  
(in thousands, except share data) 

December 31, 2022  December 31, 2021   

Assets 
Investments: 

Fixed maturities, at fair value (amortized cost of $40,127 and $35,889, respectively) 
Equity investments, at fair value (cost of $187 and $1,147, respectively) 
Limited liability investments 
Limited liability investments, at fair value 
Investments in private companies, at adjusted cost 
Real estate investments, at fair value (cost of $0 and $10,225, respectively) 
Other investments, at cost which approximates fair value 
Short-term investments, at cost which approximates fair value 

  $ 

Total investments 
Cash and cash equivalents 
Restricted cash 
Accrued investment income 
Service fee receivable, net of allowance for doubtful accounts of $147 and $241, respectively 
Other receivables, net of allowance for doubtful accounts of $8 and $5, respectively 
Deferred contract costs 
Property and equipment, net of accumulated depreciation of $1,041 and $2,235, respectively 
Right-of-use asset 
Goodwill 
Intangible assets, net of accumulated amortization of $22,228 and $19,990, respectively 
Other assets 
Assets held for sale 
Assets of discontinued operations 
Total Assets 
Liabilities and Shareholders’ Equity 
Liabilities: 
Accrued expenses and other liabilities 
Income taxes payable 
Deferred service fees 
Bank loans 
Notes payable 
Subordinated debt, at fair value 
Lease liability 
Net deferred income tax liabilities 
Liabilities held for sale 
Liabilities of discontinued operations 
Total Liabilities 
Redeemable Class A preferred stock, no par value; 1,000,000 authorized; 149,733 and 169,733 
issued and outstanding at December 31, 2022 and December 31, 2021, respectively; redemption 
amount of $6,013 and $6,497 at December 31, 2022 and December 31, 2021, respectively 
Shareholders’ Equity: 
Common stock, no par value; 50,000,000 authorized; 23,437,530 and 23,130,064 issued at 
December 31, 2022 and December 31, 2021, respectively; and 23,190,080 and 22,882,614 
outstanding at December 31, 2022 and December 31, 2021, respectively 
Additional paid-in capital 
Treasury stock, at cost; 247,450 and 247,450 outstanding at December 31, 2022 and December 31, 
2021, respectively 
Accumulated deficit 
Accumulated other comprehensive income 
Shareholders’ equity attributable to common shareholders 
Noncontrolling interests in consolidated subsidiaries 
Total Shareholders’ Equity 
Total Liabilities, Class A preferred stock and Shareholders’ Equity 

  $ 

  $ 

  $ 

See accompanying notes to Consolidated Financial Statements. 

46 

37,591      $ 
153        
983        
17,059        
790        
—        
201        
157        
56,934        
64,168        
13,064        
1,195        
10,304        
3,720        
13,257        
773        
911        
45,498        
33,099        
23,249        
19,478        
—        
285,650      $ 

55,801      $ 
945        
82,713        
34,281        
—        
67,811        
1,217        
4,176        
16,585        
—        
263,529        

35,666   
179   
1,901   
18,826   
790   
10,662   
256   
157   
68,437   
10,084   
17,257   
1,013   
6,656   
4,032   
10,930   
1,101   
2,248   
49,264   
30,833   
4,394   
19,913   
249,472   
475,634   

44,974   
294   
89,217   
26,717   
6,411   
60,973   
2,479   
28,553   
17,035   
184,227   
460,880   

6,013        

6,497   

—        
359,985        

(492 )      
(370,427 )      
26,605        
15,671        
437        
16,108        
285,650      $ 

—   
359,138   

(492 ) 
(395,149 ) 
30,779   
(5,724 ) 
13,981   
8,257   
475,634   

  
      
         
  
      
         
  
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
      
         
  
      
         
  
    
    
    
    
    
    
    
    
    
    
    
      
         
  
    
    
    
    
    
    
    
    
KINGSWAY FINANCIAL SERVICES INC. 

Consolidated Statements of Operations 
(in thousands, except per share data) 

Revenues: 

Service fee and commission revenue 

Total revenues 
Operating expenses: 

Claims authorized on vehicle service agreements 
Commissions 
Cost of services sold 
General and administrative expenses 
Disposal of subsidiary transaction expenses 

Total operating expenses 
Operating loss 
Other revenues (expenses), net: 
Net investment income 
Net realized gains 
Loss on change in fair value of equity investments 
(Loss) gain on change in fair value of limited liability investments, at fair value 
Gain on change in fair value of real estate investments 
Gain on change in fair value of derivative asset option contracts 
Non-operating other (expense) revenue 
Interest expense 
Amortization of intangible assets 
Loss on change in fair value of debt 
Gain on disposal of subsidiary 
Gain on extinguishment of debt 
Total other revenue (expenses), net 
Income (loss) from continuing operations before income tax expense (benefit) 
Income tax expense (benefit) 
Income (loss) from continuing operations 

(Loss) income from discontinued operations, net of taxes 
Loss on disposal of discontinued operations, net of taxes 

Net income 

Less: Net (loss) income from continuing operations attributable to noncontrolling interests in 
consolidated subsidiaries 
Less: Net (loss) income from discontinued operations attributable to noncontrolling interests 
in consolidated subsidiaries 
Less: Dividends on preferred stock 

Net income (loss) attributable to common shareholders 

Net income (loss) from continuing operations attributable to common shareholders 
Net (loss) income from discontinued operations attributable to common shareholders 
Net income (loss) attributable to common shareholders 

Basic earnings (loss) per share attributable to common shareholders: 

Continuing operations 
Discontinued operations 
Basic earnings (loss) per share - net income (loss) attributable to common shareholders 

Diluted earnings (loss) per share attributable to common shareholders: 

Continuing operations 
Discontinued operations 
Diluted earnings (loss) per share - net income (loss) attributable to common shareholders 

Weighted average shares outstanding (in ‘000s): 

Basic: 
Diluted: 

  $ 

  $ 

  $ 

  $ 

  $ 
  $ 
  $ 

  $ 
  $ 
  $ 

See accompanying notes to Consolidated Financial Statements. 

47 

Years ended December 31,   
2021   
2022     

93,280     $ 
93,280       

20,895       
8,358       
18,673       
43,519       
5,408       
96,853       
(3,573 )     

2,305       
1,209       
(26 )     
(1,754 )     
1,488       
16,730       
(206 )     
(8,092 )     
(6,133 )     
(4,908 )     
37,917       
—       
38,530       
34,957       
4,825       
30,132       
(12,805 )     
(2,262 )     
15,065       

78,401   
78,401   

19,536   
7,042   
7,052   
45,245   
—   
78,875   
(474 ) 

1,575   
1,809   
(242 ) 
2,391   
—   
—   
16   
(6,161 ) 
(4,837 ) 
(3,201 ) 
—   
2,494   
(6,156 ) 
(6,630 ) 
(3,916 ) 
(2,714 ) 
4,574   
—   
1,860   

(1,471 )     

1,660   

(8,186 )     
306       
24,416     $ 

31,297     $ 
(6,881 )     
24,416     $ 

1.36     $ 
(0.30 )   $ 
1.06     $ 

1.25     $ 
(0.27 )   $ 
0.98     $ 

542   
494   
(836 ) 

(4,868 ) 
4,032   
(836 ) 

(0.22 ) 
0.18   
(0.04 ) 

(0.22 ) 
0.18   
(0.04 ) 

22,961       
25,304       

22,537   
22,537   

  
  
  
  
      
        
  
    
      
        
  
    
    
    
    
    
    
    
      
        
  
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
      
        
  
      
        
  
      
        
  
    
    
 
KINGSWAY FINANCIAL SERVICES INC. 

Consolidated Statements of Comprehensive Income (Loss) 
(in thousands)  

Net income 
Other comprehensive loss, net of taxes(1): 
Unrealized (losses) gains on available-for-sale investments: 

Unrealized losses arising during the period 
Reclassification adjustment for amounts included in net income 
Change in fair value of debt attributable to instrument-specific credit risk 

Other comprehensive loss 
Comprehensive income (loss) 

Less: comprehensive (loss) income attributable to noncontrolling interests in consolidated 
subsidiaries 

Comprehensive income (loss) attributable to common shareholders 
(1) Net of income tax expense (benefit) of $0 and $0 in 2022 and 2021, respectively 

Years ended December 31,   
2021   

2022     

  $ 

15,065     $ 

1,860   

(2,330 )     
22       
(1,930 )     
(4,238 )     
10,827     $ 

(9,721 )     
20,548     $ 

(478 ) 
27   
(6,844 ) 
(7,295 ) 
(5,435 ) 

2,187   
(7,622 ) 

  $ 

  $ 

See accompanying notes to Consolidated Financial Statements. 

48 

  
  
  
  
  
  
      
        
  
      
        
  
      
        
  
    
    
    
    
    
  
 
 
Balance, December 31, 2020 
Vesting of restricted stock awards, 
net of share settlements for tax 
withholdings 
Conversion of redeemable Class A 
preferred stock to common stock 
Exercise of Series B warrants 
Net (loss) income 
Preferred stock dividends 
Distributions to noncontrolling 
interest holders 
Other comprehensive loss 
Stock-based compensation 
Balance, December 31, 2021 
Vesting of restricted stock awards, 
net of share settlements for tax 
withholdings 
Conversion of redeemable Class A 
preferred stock to common stock 
Exercise of Series B warrants 
Net income (loss) 
Preferred stock dividends 
Distributions to noncontrolling 
interest holders 
Deconsolidation of noncontrolling 
interest 
Other comprehensive loss 
Redemption of equity awards related 
to disposal of subsidiary 
Stock-based compensation 
Balance, December 31, 2022 

KINGSWAY FINANCIAL SERVICES INC. 

Consolidated Statements of Shareholders’ Equity  
(in thousands, except share data) 

    Additional       
     Paid-in 
     Capital 

   Common Stock 
    Amount       
   Shares 
    22,211,069     $  —     $  355,242     $ 

     Accumulated      
Other 

    Shareholders’       
Equity 
    Attributable to     

    Noncontrolling       
Interests in 

Total 

    Treasury     Accumulated     Comprehensive      Common 
     Stock       Deficit 

    Income (Loss)      Shareholders       Subsidiaries      

     Consolidated      Shareholders’   

Equity 

(492 )   $ 

(394,807 )   $ 

38,059       

(1,998 )   $ 

14,157     $ 

12,159   

239,402        —       

—       

—       

—       

82,143        —       
350,000        —       
—        —       
—        —       

500       
1,750       
—       
(494 )     

—       
—       
—       
—       

—       
—       
(342 )     
—       

—       

—       
—       
—       
—       

—       
—       
2,140       
    22,882,614     $  —     $  359,138     $ 

—        —       
—        —       
—        —       

—       
—       
—       
(492 )   $ 

—       
—       
—       
(395,149 )   $ 

—       
(7,280 )     
—       
30,779       

—       

—       

—   

500       
1,750       
(342 )     
(494 )     

—       
(7,280 )     
2,140       
(5,724 )   $ 

—       
—       
2,202       
—       

(2,363 )     
(15 )     
—       
13,981     $ 

500   
1,750   
1,860   
(494 ) 

(2,363 ) 
(7,295 ) 
2,140   
8,257   

73,437        —       

—       

—       

—       

125,000        —       
109,029        —       
—        —       
—        —       

788       
545       
—       
(306 )     

—       
—       
—       
—       

—       
—       
24,722       
—       

—        —       

—       

—       

—        —       
—        —       

—       
—       

—       
—       

—       

—       
—       

—       

—       
—       
—       
—       

—       

—       

—       

—   

788       
545       
24,722       
(306 )     

—       
—       
(9,657 )     
—       

788   
545   
15,065   
(306 ) 

—       

(6,016 )     

(6,016 ) 

—       
(4,174 )     

—       
(4,174 )     

2,193       
(64 )     

2,193   
(4,238 ) 

(1,056 ) 
876   
16,108   

(1,056 )     
876       
    23,190,080     $  —     $  359,985     $ 

—        —       
—        —       

—       
—       
(492 )   $ 

—       
—       
(370,427 )   $ 

—       
—       
26,605     $ 

(1,056 )     
876       
15,671     $ 

—       
—       
437     $ 

See accompanying notes to Consolidated Financial Statements. 

49 

  
  
    
  
      
  
      
  
      
  
      
  
      
  
  
      
  
  
  
    
  
      
  
      
  
      
  
      
  
  
  
  
    
  
      
  
  
      
  
    
    
  
  
    
  
      
  
  
  
  
  
      
  
      
  
      
  
      
  
      
  
      
  
  
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
    
  
 
 
KINGSWAY FINANCIAL SERVICES INC. 

Consolidated Statements of Cash Flows  
(in thousands)  

Years ended December 31,   
2021   

2022      

Cash provided by (used in): 
Operating activities: 
Net income 
Adjustments to reconcile net income to net cash provided by (used in) operating activities: 
Loss (income) from discontinued operations, net of taxes 
Loss on disposal of discontinued operations, net of taxes 
Equity in net income of limited liability investments 
Depreciation and amortization expense 
Stock-based compensation expense, net of forfeitures 
Net realized gains 
Loss on change in fair value of equity investments 
Loss (gain) on change in fair value of limited liability investments, at fair value 
Gain on change in fair value of real estate investments 
Loss on change in fair value of debt 
(Gain) loss on change in fair value of derivatives 
Loss on change in fair value of contingent consideration 
Deferred income taxes, adjusted for Ravix liabilities assumed 
Amortization of fixed maturities premiums and discounts 
Gain on disposal of subsidiary 
Gain on extinguishment of debt 
Changes in operating assets and liabilities: 

Service fee receivable, net, adjusted for CSuite, SNS and Ravix assets acquired 
Other receivables, net, adjusted for CSuite and Ravix assets acquired 
Deferred contract costs 
Other assets, adjusted for CSuite, SNS and Ravix assets acquired 
Deferred service fees 
Other, net, adjusted for CSuite, SNS and Ravix assets acquired and liabilities assumed 

Cash (used in) provided by operating activities - continuing operations 
Cash used in operating activities - discontinued operations 
Net cash used in operating activities 
Investing activities: 
Proceeds from sales and maturities of fixed maturities 
Proceeds from sales of equity investments 
Purchases of fixed maturities 
Net proceeds from limited liability investments 
Net proceeds from limited liability investments, at fair value 
Net proceeds from investments in private companies 
Proceeds from sale of real estate investments 
Net proceeds from other investments 
Net proceeds from disposal of subsidiary, net of cash disposed of $1,391 
Acquisition of businesses, net of cash acquired 
Acquisition of assets, net of cash acquired 
Net disposals (purchases) of property and equipment 
Cash provided by (used in) investing activities - continuing operations 
Cash provided by investing activities - discontinued operations 
Net cash provided by (used in) investing activities 
Financing activities: 
Proceeds from exercise of warrants 
Distributions to noncontrolling interest holders 
Payment of contingent consideration from acquisition 
Taxes paid related to net share settlements of restricted stock awards 
Principal proceeds from bank loans, net of debt issuance costs of $167 in 2022 and $160 in 2021 
Principal payments on bank loans 
Principal payments on notes payable 
Cash used in financing activities - continuing operations 
Cash (used in) provided by financing activities - discontinued operations 
Net cash used in financing activities 
Net increase (decrease) in cash and cash equivalents and restricted cash from continuing operations 
Cash and cash equivalents and restricted cash at beginning of period 
Less: cash and cash equivalents and restricted cash of discontinued operations 
Cash and cash equivalents and restricted cash of continuing operations at beginning of period 
Cash and cash equivalents and restricted cash of continuing operations at end of period 

50 

   $ 

15,065       $ 

12,805         
2,262         
(293 )      
6,449         
4,052         
(1,209 )      
26         
1,754         
(1,488 )      
4,908         
(17,070 )      
1,510         
1,406         
236         
(37,917 )      
—         

(136 )      
(7 )      
(2,327 )      
(2,067 )      
(6,504 )      
15,916         
(2,629 )      
(11,945 )      
(14,574 )      

9,714         
—         
(14,211 )      
1,577         
621         
258         
12,150         
55         
35,158         
(13,689 )      
—         
26,461         
58,094         
42,846         
100,940         

545         
(6,016 )      
(750 )      
(396 )      
12,682         
(5,228 )      
(6,411 )      
(5,574 )      
(32,358 )      
(37,932 )      
49,891         
29,899         
2,558         
27,341         
77,232       $ 

   $ 

1,860   

(4,574 ) 
—   
(27 ) 
5,067   
3,598   
(1,809 ) 
242   
(2,391 ) 
—   
3,201   
14   
263   
2,203   
230   
—   
(2,494 ) 

(791 ) 
75   
(2,095 ) 
(387 ) 
(2,354 ) 
6,647   
6,478   
(12,386 ) 
(5,908 ) 

6,251   
23   
(21,868 ) 
2,664   
17,006   
391   

38   
—   
(10,003 ) 
(2,635 ) 
(830 ) 
(8,963 ) 
365   
(8,598 ) 

1,750   
(2,363 ) 
—   
(499 ) 
6,240   
(4,914 ) 
(9,474 ) 
(9,260 ) 
8,720   
(540 ) 
(11,745 ) 
44,945   
5,859   
39,086   
27,341   

  
  
  
  
        
           
  
        
           
  
        
           
  
     
     
     
     
     
     
     
     
     
     
     
     
     
     
     
     
        
           
  
     
     
     
     
     
     
     
     
     
        
           
  
     
     
     
     
     
     
     
    
     
     
     
     
     
     
     
     
        
           
  
     
     
     
     
     
     
     
     
     
     
     
     
     
     
 
 
 
KINGSWAY FINANCIAL SERVICES INC. 

Supplemental disclosures of cash flows information: 
Cash paid by continuing operations during the year for: 

Interest 
Income taxes 

Non-cash investing and financing activities from continuing operations: 

Contingent consideration for acquisition of business 
Conversion of redeemable Class A preferred stock to common stock 
Accrued dividends on Class A preferred stock issued 

Years ended December 31,   
2021   

2022      

   $ 
   $ 

   $ 
   $ 
   $ 

1,427       $ 
501       $ 

—       $ 
788       $ 
306       $ 

821   
243   

2,195   
500   
340   

See accompanying notes to Consolidated Financial Statements. 

51 

  
  
  
  
        
           
  
        
           
  
        
           
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

NOTE 1 BUSINESS  

Kingsway Financial Services Inc. (the “Company” or “Kingsway”) was incorporated under the Business Corporations Act (Ontario) on 
September 19, 1989. Effective December 31, 2018, the Company changed its jurisdiction of incorporation from the province of Ontario, 
Canada, to the State of Delaware. Kingsway is a holding company with operating subsidiaries located in the United States. The Company 
owns or controls subsidiaries primarily in the extended warranty and business services industries. 

NOTE 2 SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES 

(a) 

Principles of consolidation: 

The  accompanying  information  in  the 2022  Annual  Report  has  been  prepared  in  accordance  with  accounting  principles  generally 
accepted in the United States of America (“U.S. GAAP”). 

The  accompanying  consolidated  financial  statements  include  the  accounts  of  Kingsway  and  its  majority  owned  and  controlled 
subsidiaries. All significant intercompany accounts and transactions have been eliminated in consolidation. 

In  addition,  the  Company  evaluates  its  relationships or  investments  for consolidation pursuant  to  authoritative  accounting  guidance 
related to the consolidation of a variable interest entity (“VIE”) under the Variable Interest Model prescribed by the Financial Accounting 
Standards Board (“FASB”). 

The Company’s investments include certain investments, primarily in limited liability companies and limited partnerships in which the 
Company holds a variable interest. The Company evaluates these investments for the characteristics of a VIE. The Variable Interest Model 
identifies  the  characteristics  of  a  VIE  to  include  investments  (1)  lacking  sufficient  equity  to  finance  activities  without  additional 
subordinated support or (2) in which the holders of equity at risk in the investments lack characteristics of a controlling financial interest, 
such as the power to direct activities that most significantly impact the legal entity’s economic performance; the obligation to absorb the 
legal entity’s expected losses; or the right to receive the expected residual returns of the legal entity. The equity investors as a group are 
considered to lack the power to direct activities that most significantly impact the legal entity’s economic performance when (1) the voting 
rights of some investors are not proportional to their obligations to absorb the expected losses of the legal entity or their rights to receive 
the expected residual returns of the legal entity and (2) substantially all of the activities of the legal entity are conducted on behalf of an 
investor with disproportionately few voting rights. When evaluating whether an investment lacks characteristics of a controlling financial 
interest, the Company considers limited liability companies and limited partnerships to lack the power of a controlling financial interest 
if neither of the following exists: (1) a simple majority or lower threshold of partners or members with equity at risk are able to exercise 
substantive kick-out rights through voting interest over the general partner(s) or managing member(s) or (2) limited partners with equity 
at risk are able to exercise substantive participating rights over the general partner(s) or managing member(s). 

If the characteristics of a VIE are met, the Company evaluates whether it meets the primary beneficiary criteria. The primary beneficiary 
is considered to be the entity holding a variable interest that has the power to direct activities that most significantly impact the economic 
performance of the VIE; the obligation to absorb losses of the VIE; or the right to receive benefits from the VIE that could potentially 
be significant to the VIE. In instances where the Company is considered to be the primary beneficiary, the Company consolidates the 
VIE. When the Company is not considered to be the primary beneficiary of the VIE, the VIE is not consolidated and the Company uses 
the equity method to account for the investment. Under this method, the carrying value is generally the Company’s share of the net asset 
value of the unconsolidated entity, and changes in the Company’s share of the net asset value are recorded in net investment income. 

Certain  prior  year  amounts  have  been  reclassified  to  conform  to  current  year  presentation.  Such  reclassifications  had  no  impact  on 
previously reported net income or total shareholders’ equity. 

Subsidiaries  

The Company’s consolidated financial statements include the assets, liabilities, shareholders’ equity, revenues, expenses and cash flows 
of the holding company and its subsidiaries and have been prepared in accordance with U.S. GAAP. A subsidiary is an entity controlled, 
directly or indirectly, through ownership of more than 50% of the outstanding voting rights, or where the Company has the power to 
govern the financial and operating policies so as to obtain benefits from its activities. Assessment of control is based on the substance 
of the relationship between the Company and the entity and includes consideration of both existing voting rights and, if applicable, 
potential voting rights that are currently exercisable and convertible. The operating results of subsidiaries that have been disposed are 
included up to the date control ceased, and any difference between the fair value of the consideration received and the carrying value of 
a  subsidiary  that  has  been  disposed  is  recognized  in  the  consolidated  statements  of  operations.  All  intercompany  balances  and 
transactions are eliminated in full. 

52 

  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

The consolidated financial statements are prepared as of December 31, 2022 based on individual company financial statements at the 
same date, or in the case of certain limited liability companies that are consolidated, on a three-month lag basis. Accounting policies of 
subsidiaries have been aligned where necessary to ensure consistency with those of Kingsway. 

The Company’s subsidiaries Argo Holdings Fund I, LLC (“Argo Holdings”), Flower Portfolio 001, LLC (“Flower”) and Net Lease 
Investment Grade Portfolio LLC (“Net Lease”) meet the definition of an investment company and follow the accounting and reporting 
guidance in Financial Accounting Standards Codification Topic 946, Financial Services-Investment Companies. 

Noncontrolling interests  

The Company has noncontrolling interests attributable to certain of its subsidiaries. A noncontrolling interest arises where the Company 
owns less than 100% of the voting rights and economic interests in a subsidiary. A noncontrolling interest is initially recognized at the 
proportionate  share  of  the  identifiable  net  assets  of  the  subsidiary  at  the  acquisition  date  and  is  subsequently  adjusted  for  the 
noncontrolling interest’s share of the acquiree’s net income (loss) and changes in capital. The effects of transactions with noncontrolling 
interests are recorded in shareholders’ equity where there is no change of control. 

(b) 

Use of estimates: 

The  preparation  of  consolidated  financial  statements  in  accordance  with  U.S.  GAAP  requires  management  to  make  estimates  and 
assumptions  that  affect  the  reported  amounts  and  classification  of  assets  and  liabilities,  revenues  and  expenses,  and  the  related 
disclosures of contingent assets and liabilities in the consolidated financial statements and accompanying notes. Actual results could 
differ from these estimates. Estimates and their underlying assumptions are reviewed on an ongoing basis. Changes in estimates are 
recorded in the accounting period in which they are determined. 

The critical accounting estimates and assumptions in the accompanying consolidated financial statements include, but are not limited 
to,  revenue  recognition; valuation  of  fixed  maturities  and  equity  investments;  impairment  assessment  of  investments;  valuation  of 
limited  liability  investments,  at  fair  value;  valuation  of  deferred  income  taxes;  accounting  for  business  combinations  and  asset 
acquisitions;  valuation  and  impairment  assessment  of  intangible  assets;  goodwill  recoverability;  deferred  contract  costs;  fair  value 
assumptions  for  subordinated  debt  obligations;  fair  value  assumptions  for  subsidiary  stock-based  compensation  awards;  fair  value 
assumptions for derivative instruments and contingent consideration. 

(c) 

Business combinations and asset acquisitions: 

The  Company  evaluates  acquisitions in  accordance  with  Accounting  Standards  Codification  (“ASC”)  805,  Business  Combinations 
(“ASC  805”), to  determine  if  a  transaction  represents an  acquisition  of  a  business or  an  acquisition of  assets. The  results  of 
acquired subsidiaries are included in the consolidated statements of operations from the date of acquisition. 

An acquisition of a business represents a business combination.  The acquisition method of accounting is used to account for a business 
combination. The cost of an acquired business is measured as the fair value of the assets received, equity instruments issued and liabilities 
incurred or assumed at the date of exchange. Identifiable assets acquired and liabilities and contingent liabilities assumed in a business 
combination are measured initially at their fair values at the acquisition date, irrespective of the extent of any noncontrolling interest. 
The excess of the  cost of  an acquired business over  the fair  value of  the  Company’s  share  of  the  identifiable net  assets  acquired  is 
recorded as goodwill. If the cost of acquired business is less than the fair value of the net assets of the subsidiary acquired, the difference 
is recognized in the consolidated statements of operations. Noncontrolling interests in the net assets of consolidated entities are reported 
separately in shareholders’ equity and initially measured at fair value.  Acquisition costs related to a business combination are expensed 
as incurred. 

When an acquisition does not meet the definition of a business combination either because: (i) substantially all of the fair value of the 
gross assets acquired is concentrated in a single identifiable asset, or group of similar identified assets, or (ii) the acquired entity does 
not have an input and a substantive process that together significantly contribute to the ability to create outputs, the Company accounts 
for the acquisition as an asset acquisition.  In an asset acquisition, goodwill is not recognized.  Any excess of the total purchase price 
plus transaction costs over the fair value of the net assets acquired is allocated on a relative fair value basis to the identifiable net assets 
at the acquisition date. 

53 

  
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

(d) 

Investments: 

Investments in fixed maturities are classified as available-for-sale and reported at fair value. Unrealized gains and losses are included in 
accumulated other comprehensive income, net of tax, until sold or until an other-than-temporary impairment is recognized, at which 
point cumulative unrealized gains or losses are reclassified to the consolidated statements of operations. 

Equity investments include common stocks and warrants and are reported at fair value. Changes in fair value of equity investments are 
recognized in net income. 

Limited  liability  investments  include  investments  in  limited  liability  companies  and  limited  partnerships  in  which  the  Company’s 
interests are not deemed minor and, therefore, are accounted for under the equity method of accounting. The most recently available 
financial statements are used in applying the equity method. The difference between the end of the reporting period of the limited liability 
entities and that of the Company is no more than three months. Income or loss from limited liability investments is recognized based on 
the Company’s share of the earnings of the limited liability entities and is included in net investment income. 

Limited liability investments, at fair value are accounted for at fair value with changes in fair value included in gain on change in fair 
value  of  limited  liability  investments,  at  fair  value.  The  difference  between  the  end  of  the  reporting  period  of  the  limited  liability 
investments, at fair value and that of the Company is no more than three months. 

Investments in private companies consist of convertible preferred stocks and notes in privately owned companies and investments in 
limited liability companies in which the Company’s interests are deemed minor. These investments do not have readily determinable 
fair values and, therefore, are reported at cost, adjusted for observable price changes and impairments. Changes in carrying value are 
included in net change in unrealized loss on private company investments. 

Real estate investments are reported at fair value, which is zero as of December 31, 2022 due to the sale of Flower’s investment real 
estate properties for $12.2 million on September 29, 2022.   Note 7, “Investments,” for further details. 

Other investments include collateral loans and are reported at their unpaid principal balance, which approximates fair value. 

Short-term investments, which consist of investments with original maturities between three months and one year, are reported at cost, 
which approximates fair value. 

Realized gains and losses on sales, determined on a first-in first-out basis, are included in net realized gains. 

Dividends and interest income are included in net investment income. Investment income is recorded as it accrues. 

The Company accounts for all financial instruments using trade date accounting. 

The Company conducts a quarterly review to identify and evaluate investments that show objective indications of possible impairment. 
Impairment is charged to the consolidated statements of operations if the fair value of an instrument falls below its cost/amortized cost 
and the decline is considered other-than-temporary. Factors considered in determining whether a loss is other-than-temporary include 
the length of time and extent to which fair value has been below cost; the financial condition and near-term prospects of the issuer; and 
the Company’s ability and intent to hold investments for a period of time sufficient to allow for any anticipated recovery. 

(e) 

Cash and cash equivalents: 

Cash and cash equivalents include cash and investments with original maturities of no more than three months when purchased that are 
readily convertible into cash. 

(f) 

Restricted cash: 

Restricted cash represents certain cash and cash equivalent balances restricted as to withdrawal or use. The Company’s restricted cash 
is  comprised  primarily  of  cash  held  for  the  payment  of  vehicle  service  agreement  claims  under  the  terms  of  certain  contractual 
agreements, funds held in escrow, statutory deposits and amounts pledged to third-parties as deposits or to collateralize liabilities. 

54 

  
  
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

(g) 

Service fee receivable: 

Service fee receivable includes balances due and uncollected from customers. Service fee receivable is reported net of an estimated 
allowance for doubtful accounts. The allowance for doubtful accounts is determined based on periodic evaluations of aged receivables, 
historical business data, management’s experience and current economic conditions. 

(h) 

Deferred contract costs:  

Deferred contract costs represent the deferral of incremental costs to obtain or fulfill a contract with a customer.  Incremental costs to 
obtain a contract with a customer primarily include sales commissions.  The Company capitalizes costs incurred to fulfill a contract if 
the  costs are  identifiable,  generate  or  enhance  resources  used  to  satisfy  future  performance  obligations  and  are  expected  to  be 
recovered.   Costs  to  fulfill  a  contract include  labor  costs  for set-up  activities  directly  related  to  the  acquisition  of  vehicle  service 
agreements.  Contract costs are deferred and amortized over the expected customer relationship period consistent with the pattern in 
which  the  related  revenues  are  earned.  Amortization  of  incremental  costs to  obtain  a  contract  and  costs  to  fulfill  a  contract with  a 
customer  are  recorded  in  commissions  and general  and  administrative  expenses,  respectively, in  the  consolidated  statements  of 
operations. Changes in estimates, if any, are recorded in the accounting period in which they are determined. 

(i) 

Property and equipment: 

Property and equipment are reported in the consolidated financial statements at cost. Depreciation of property and equipment has been 
provided  using  the  straight-line  method  over  the  estimated  useful  lives  of  such  assets.  Repairs  and  maintenance  are  recognized  in 
operations during the period incurred. Land is not depreciated. The Company estimates useful life to be three to ten years for leasehold 
improvements; three to seven years for furniture and equipment; and three to five years for computer hardware. 

(j) 

Goodwill and intangible assets: 

When the Company acquires a subsidiary or other business where it exerts significant influence, the fair value of the net tangible and 
intangible assets acquired is determined and compared to the amount paid for the subsidiary or business acquired. Any excess of the 
amount paid over the fair value of those net assets is considered to be goodwill. 

Goodwill is tested for impairment annually as of November 30, or more frequently if events or circumstances indicate that the carrying 
value may not be recoverable, to ensure that its fair value is greater than or equal to the carrying value. Any excess of carrying value 
over fair value is charged to the consolidated statements of operations in the period in which the impairment is determined. 

When the Company acquires a subsidiary or other business where it exerts significant influence or acquires certain assets, intangible assets 
may be acquired, which are recorded at their fair value at the time of the acquisition. An intangible asset with a definite useful life is 
amortized in the consolidated statements of operations over its estimated useful life. The Company writes down the value of an intangible 
asset with a definite useful life when the undiscounted cash flows are not expected to allow for full recovery of the carrying value. 

Intangible assets with indefinite useful lives are not subject to amortization and are tested for impairment annually as of November 30, 
or more frequently if events or circumstances indicate that the carrying value may not be recoverable, to ensure that fair values are 
greater  than  or  equal  to  carrying  values.  Any  excess  of  carrying  value  over  fair  value  is  charged  to  the  consolidated  statements  of 
operations in the period in which the impairment is determined. 

(k) 

Derivative financial instruments: 

Derivative financial instruments include an interest rate swap contact and the trust preferred debt repurchase options.   The Company 
measures derivative financial instruments at fair value. The fair value of derivative financial instruments is required to be revalued each 
reporting period, with corresponding changes in fair value recorded in the consolidated statements of operations. Realized gains or losses 
are recognized upon settlement of the contracts.  Refer to Note 11, “Derivatives,” for further information.  

The Company entered into a pay fixed, receive variable interest rate swap contract to reduce its exposure to changes in interest rates.  The 
interest rate swap contract is included in other assets and accrued expenses and other liabilities in the consolidated balance sheets at 
December 31, 2022 and December 31, 2021, respectively. The Company has not elected hedge accounting for the interest rate swap, 
therefore changes in fair value are recorded in current period earnings and are included in interest expense in the consolidated statements 
of operations. 

55 

  
  
  
  
  
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

During the third quarter of 2022, the Company entered into three trust preferred debt repurchase option agreements. The trust preferred 
debt repurchase options are included in other assets in the consolidated balance sheet at December 31, 2022 with changes in fair value 
included in gain on change in fair value of derivative asset option contracts in the consolidated statement of operations.    

(l) 

Debt: 

Bank loans and notes payable are reported in the consolidated balance sheets at par value adjusted for unamortized discount or premium 
and unamortized issuance costs. Discounts, premiums, and costs directly related to the issuance of debt are capitalized and amortized 
through the maturity date of the debt using the effective interest rate method and are recorded in interest expense in the consolidated 
statements of operations. Gains and losses on the extinguishment of debt are recorded in gain on extinguishment of debt. 

The Company’s subordinated debt is measured and reported at fair value. The fair value of the subordinated debt is calculated using a 
model  based  on  significant  market  observable  inputs  and  inputs  developed  by  a  third-party.  These  inputs  include  credit  spread 
assumptions developed by a third-party and market observable swap rates. The portion of the change in fair value of subordinated debt 
related to the instrument-specific credit risk is recognized in other comprehensive loss. 

(m) 

Contingent consideration: 

The consideration for certain of the Company’s acquisitions include future payments to former owners that are contingent upon the 
achievement of certain targets over future reporting periods. Liabilities for contingent consideration are measured and reported at fair 
value at the date of acquisition and are included in accrued expenses and other liabilities in the consolidated balance sheets. Changes in 
the fair value of  contingent consideration  liabilities  can result  from  changes  to one or  multiple  inputs,  including  adjustments  to  the 
discount rates or changes in the assumed achievement or timing of any targets. These fair value measurements are based on significant 
inputs not observable in the market. Changes in assumptions could have an impact on the payout of contingent consideration liabilities. 
Changes in fair value are reported in the consolidated statements of operations as non-operating other (expense) revenue. 

(n) 

Income taxes: 

The Company follows the asset and liability method of accounting for income taxes, whereby deferred income tax assets and liabilities 
are recognized for (i) the differences between the financial statement carrying amount of existing assets and liabilities and their respective 
tax bases  and (ii)  loss  and  tax  credit  carryforwards. Deferred  income  tax  assets  and  liabilities  are measured  using  enacted  tax  rates 
expected to apply to taxable income in the years in which those temporary differences are expected to be recovered or settled. The effect 
on deferred tax assets and liabilities of a change in tax rates is recognized in income in the period that includes the date of enactment. 
Future tax benefits are recognized to the extent that realization of such benefits is more likely than not and a valuation allowance is 
established  for  any  portion  of  a  deferred  tax  asset  that  management  believes  will  not  be  realized.  Current  federal  income  taxes  are 
charged or credited to operations based upon amounts estimated to be payable or recoverable as a result of taxable operations for the 
current year. The Company accounts for uncertain tax positions in accordance with the income tax accounting guidance. The Company 
recognizes interest and penalties, if any, related to unrecognized tax benefits in income tax expense (benefit). 

(o) 

Leases: 

The Company records a right of use asset and lease liability for all leases in which the estimated term exceeds twelve months. The 
Company treats contracts as a lease when the contract: (1) conveys the right to use a physically distinct property or equipment asset for 
a period of time in exchange for consideration, (2) the Company directs the use of the asset and (3) the Company obtains substantially 
all the economic benefits of the asset. Right-of-use assets and lease liabilities are measured and recognized based on the present value 
of the future minimum lease payments over the lease term at the commencement date. As the Company’s leases are office leases, the 
Company is unable to determine an implicit rate; therefore, the Company uses its incremental borrowing rate based on the information 
available at the lease commencement date in determining the present value of future payments for those leases. The Company includes 
options to extend or terminate the lease in the measurement of the right-of-use asset and lease liability when it is reasonably certain that 
such options will be exercised. Lease expense for minimum lease payments is recognized on a straight-line basis over the lease term. 

The Company determines lease classification at the commencement date. Leases not classified as sales-type (lessor) or financing leases 
(lessor and lessee) are classified as operating leases. The primary accounting criteria the Company uses that results in operating lease 
classification are: (a) the lease does not transfer ownership of the underlying asset to the lessee by the end of the lease term, (b) the lease 
does not grant the lessee a purchase option that the lessee is reasonably certain to exercise, (c) using a seventy-five percent or more 
threshold in addition to other qualitative factors, the lease term is not for a major part of the remaining economic life of the underlying 

56 

  
  
  
  
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

asset, (d) using a ninety percent or more threshold in addition to other qualitative factors, the present value of the sum of the lease payments 
and residual value guarantee from the lessee, if any, does not equal or substantially exceed the fair value of the underlying asset. 

As an accounting policy, the Company has elected not to apply the recognition requirements in ASC 842 to short-term leases (generally 
those with terms of twelve months or less). Instead, the Company recognizes the lease payments as expense on a straight-line basis over 
the lease term and any variable lease payments in the period in which the obligation for those payments is incurred. 

Rental  expense  for  operating  leases  is  recognized  on  a  straight-line  basis  over  the  lease  term,  net  of  any  applicable  lease  incentive 
amortization.  

(p) 

Revenue recognition: 

Service fee and commission revenue and deferred service fees 

Service  fee  and  commission  revenue  represents  vehicle  service  agreement  fees,  guaranteed  asset  protection  products  (“GAP”) 
commissions,  maintenance  support  service  fees,  warranty  product  commissions,  homebuilder  warranty  service  fees, homebuilder 
warranty commissions and business services consulting revenue based on terms of various agreements with credit unions, consumers, 
businesses and homebuilders. Customers either pay in full at the inception of a warranty contract, commission product sale, or when 
consulting services are billed, or on terms subject to the Company’s customary credit reviews. 

Vehicle service agreement fees include the fees collected to cover the costs of future automobile mechanical breakdown claims and the 
associated administration of those claims. Vehicle service agreement fees are earned over the duration of the vehicle service agreement 
contracts as the single performance obligation is satisfied. Vehicle service agreement fees are initially recorded as deferred service fees 
with revenues recognized over the term of the contract based on the proportion of expected claims to total overall claims to be incurred 
over the life of the contract.  The Company believes this reasonably represents the transfer of services to the vehicle service contract 
holder over the warranty term. The Company compares the remaining deferred service fees balance to the estimated amount of expected 
future claims under the vehicle service agreement contracts and records an additional accrual if the deferred service fees balance is less 
than expected future claims costs. 

In  certain  jurisdictions  the  Company  is  required  to  refund  to  a  customer  a  pro-rata  share  of  the vehicle  service  agreement  fees  if  a 
customer cancels the agreement prior to the end of the term. Depending on the jurisdiction, the Company may be entitled to deduct from 
the refund a cancellation fee and/or amounts for claims incurred prior to cancellation. While refunds vary depending on the term and 
type of product offered, historically refunds have averaged 9% to 13% of the original amount of the vehicle service agreement fee. 
Revenues recorded by the Company are net of variable consideration related to refunds and the associated refund liability is included in 
accrued expenses and other liabilities. The Company estimates refunds based on the actual historical refund rates by warranty type 
taking into consideration current observable refund trends in estimating the expected amount of future customer refunds to be paid at 
each reporting period. 

Maintenance  support  service  fees  include  the  service  fees  collected  to  administer  equipment  breakdown  and  maintenance  support 
services and are earned as services are rendered. 

Warranty  product  commissions  include  the  commissions  from  the  sale  of  warranty  contracts  for  certain  new  and  used  heating, 
ventilation,  air  conditioning  (“HVAC”),  standby  generator,  commercial  LED  lighting  and  commercial  refrigeration  equipment.  The 
Company acts as an agent on behalf of the third-party insurance companies that underwrite and guaranty these warranty contracts. The 
Company does not guaranty the performance underlying the warranty contracts it sells. Warranty product commissions are earned at the 
time of the warranty product sales. 

Homebuilder  warranty  service  fees  include  fees  collected  from  the  sale  of  warranties  issued  by  new  homebuilders.  The  Company 
receives a single warranty service fee as its transaction price at the time it enters into a written contract with each of its builder customers. 
Each contract contains two separate performance obligations - warranty administrative services and other warranty services. Warranty 
administrative services include enrolling each home sold by the builder into the program and the warranty administrative system and 
delivering  the  warranty  product.  Other  warranty  services  include  answering  builder  or  homeowner  questions  regarding  the  home 
warranty and dispute resolution services. 

Standalone selling prices are not directly observable in the contract for each of the separate home warranty performance obligations. As 
a result, the Company has applied the expected cost plus a margin approach to develop models to estimate the standalone selling price 
for each of its performance obligations in order to allocate the transaction price to the two separate performance obligations identified. 

57 

  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

For the model related to the warranty administrative services performance obligation, the Company makes judgments about which of 
its actual costs are associated with enrolling each home sold by the builder into the program and the warranty administrative system and 
delivering  the  warranty  product.  For  the  model  related  to  the  other  warranty  services  performance  obligation,  the  Company  makes 
judgments about which of its actual costs are associated with activities, such as answering builder or homeowner questions regarding 
the home warranty and dispute resolution services, which are performed over the life of the warranty coverage period. The relative 
percentage of expected costs plus a margin associated with the warranty administrative services performance obligation is applied to the 
transaction price to determine the estimated standalone selling price of the warranty administrative services performance obligation, 
which the Company recognizes as earned at the time the home is enrolled and the warranty product is delivered. The relative percentage 
of expected costs plus a margin associated with the other warranty services performance obligation is applied to the transaction price to 
determine the estimated standalone selling price of the other warranty services performance obligation, which the Company recognizes 
as earned as services are performed over the warranty coverage period. 

For the other warranty services performance obligation, the Company applies an input method of measurement, based on the expected 
costs plus a margin of providing services, to determine the transfer of its services over the warranty coverage period. The Company uses 
historical data regarding the number of calls it receives and activities performed, in addition to the number of homes enrolled, to estimate 
the number of complaints and dispute resolution requests to be received by year until coverage expires, which allows the Company to 
develop a revenue recognition pattern that it believes provides a faithful depiction of the transfer of services over time for the other 
warranty services performance obligation. 

Homebuilder warranty commissions include commissions from the sale of warranty contracts for those builders who have requested and 
receive insurance backing of their warranty obligations. The Company acts as an agent on behalf of the third-party insurance company 
that underwrites and guaranties these warranty contracts. Homebuilder warranty commissions are earned on the certification date, which 
is typically the date of the closing of the sale of the home to the buyer. The Company also earns fees to manage remediation or repair 
services related to claims on insurance-backed warranty obligations, which are earned when the claims are closed. 

Kingsway  Search  Xcelerator  consulting 
finance  and  human 
resources consulting services, as well as healthcare professional staffing services. The Company invoices for services revenue based on 
contracted rates.  Revenue is earned as services are provided. 

revenue from  providing outsourced 

includes 

revenue 

the 

Contingent consideration receivable 

The terms of the sale of one of the Company’s subsidiaries includes potential receipt by the Company of future earnout payments. The 
gain related to the earnout payments is recorded when the consideration is determined to be realizable and is reported in the consolidated 
statements of operations as gain on disposal of subsidiary. The assumptions and methodologies used are continually reviewed and any 
adjustments are reflected in the consolidated statements of operations in the period in which the adjustments are made.  See Note 5, 
“Disposal and Discontinued Operations,” for further discussion. 

(q) 

Stock-based compensation: 

The  Company  uses  the  fair-value  method  of  accounting  for  stock-based  compensation  awards  granted  to  employees.  Expense  is 
recognized on a straight-line basis over the requisite service period during which awards are expected to vest, with a corresponding 
increase to either additional paid-in capital for equity-classified awards or to a liability for liability-classified awards. Liability-classified 
awards, included in accrued expenses and other liabilities in the consolidated balance sheets, are measured and reported at fair value on 
the date of  grant  and  are remeasured  each  reporting period.   Compensation  expense  related  to  the  change in  fair value for  liability-
classified awards is reported in the consolidated statements of operations as general and administrative expenses. For awards with a 
graded vesting  schedule,  expense  is  recognized on  a  straight-line basis over  the requisite  service  period  for  each  separately  vesting 
portion of the award. For awards subject to a performance condition, expense is recognized when the performance condition has been 
satisfied or is probable of being satisfied. For awards subject to a market condition, compensation expense is recognized on a straight-
line basis regardless of whether the market condition is satisfied, provided that the requisite service has been provided.  Forfeitures are 
recognized in the period that the award is forfeited. 

(r) 

Fair value of financial instruments: 

The fair values of the Company’s investments in fixed maturities and equity investments, limited liability investments, at fair value, real 
estate  investments,  subordinated  debt,  stock-based  compensation  liabilities, derivative  financial  instruments and  contingent 
consideration are estimated using a fair value hierarchy to categorize the inputs it uses in valuation techniques. Fair values for other 
investments approximate their unpaid principal balance. The carrying amounts reported in the consolidated balance sheets approximate 

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KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

fair values for cash and cash equivalents, restricted cash, short-term investments and certain other assets and other liabilities because of 
their short-term nature. 

(s) 

Holding company liquidity: 

The Company’s Extended Warranty and Kingsway Search Xcelerator subsidiaries fund their obligations primarily through service fee 
and commission revenue.  

The liquidity of the holding company is managed separately from its subsidiaries. The obligations of the holding company primarily 
consist of holding company operating expenses; transaction-related expenses; investments; certain debt and associated interest; and any 
other extraordinary demands on the holding company. 

The holding company’s liquidity, defined as the amount of cash in the bank accounts of Kingsway Financial Services Inc. and Kingsway 
America Inc. (“KAI”), was $48.9 million and $2.2 million at December 31, 2022 and December 31, 2021, respectively. The holding 
company cash amounts are reflected in the cash and cash equivalents of $64.2 million and $10.1 million reported at December 31, 2022 
and December 31, 2021, respectively, on the Company’s consolidated balance sheets.  

In addition to its collections from subsidiaries and holding company expenditures, the Company anticipates the following cash inflows 
and outflows over the next twelve months: 

•  Inflows: 

•  Distributions from Net Lease of $8.3 million, from the sale of the last commercial real estate property in February 2023 

•  $3.7 million from the exercise of 0.7 million warrants from January 1 through February 28, 2023 

•  $1.5 million distribution from Amigo, given that as of early March 2023 it was no longer a regulated insurance company 

•  Outflows: 

•  $56.5  million  to  repurchase  the  trust  preferred  debt  instruments  (aka  subordinate  debt)  for  which  it  has  the  option  to 
repurchase,  which  outflow  is  expected  no  later  than  March  15,  2023  (see  Note  11,  “Derivatives,” and  Note  26, 
“Subsequent Events ”) 

•  $4.7 million of deferred interest to the remaining trust preferred debt instrument for which the Company did not have the 
right to repurchase (see Note 26, “Subsequent Events”); the Company would have the ability to defer interest payments for 
up to 20 quarters on the remaining trust preferred debt instrument, if it so elected 

•  $6.1 million required to redeem the Class A Preferred  Shares; however, based on discussions with the holders of the Class 
A Preferred Shares, the Company anticipates that 100% of the Class A Preferred Shares would be converted and, in that case, 
there  would  be  no  cash  outlay  by  the  Company  (see  Note  19,  “Redeemable  Class  A  Preferred  Stock,”  and  Note  26, 
“Subsequent Events”) 

The Company notes there are outstanding warrants that expire in September 2023 (see Note 20, “Shareholders’ Equity”) and, if all 
outstanding warrants were exercised, the Company would receive an additional $18.7 million.  The Company also notes that it has an 
additional $10 million available from the second amendment to the 2020 KWH Loan (see Note 12, “Debt,” and Note 26, “Subsequent 
Events”), that is available to be drawn. 

Based  on  the  Company’s  current  business  plan  and  revenue  prospects,  existing  cash,  cash  equivalents,  investment  balances  and 
anticipated cash flows from operations are expected to be sufficient to meet the Company’s working capital and operating expenditure 
requirements, including the cash that may be required to redeem the Preferred Shares, repurchase its trust preferred securities and to pay 
the deferred interest on its trust preferred securities, for the next twelve months. However, the Company’s assessment could also be 
affected by various risks and uncertainties, including, but not limited to, the developing macro-economic environment. 

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KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

NOTE 3 RECENTLY ISSUED ACCOUNTING STANDARDS 

(a) 

Adoption of New Accounting Standards: 

Effective January 1, 2022, the Company adopted Accounting Standards Update (“ASU”) 2021-04, Earnings Per Share (Topic 260), 
Debt—Modifications and Extinguishments (Subtopic 470-50), Compensation—Stock Compensation (Topic 718), and Derivatives and 
Hedging—Contracts  in  Entity’s  Own  Equity  (Subtopic  815-40):  Issuer’s  Accounting  for  Certain  Modifications  or  Exchanges  of 
Freestanding Equity-Classified Written Call Options (a consensus of the FASB Emerging Issues Task Force) (“ASU 2021-04”). ASU 
2021-04 clarifies and reduces diversity in an issuer’s accounting for modifications or exchanges of freestanding equity-classified written 
call options (for example, warrants) that remain equity classified after modification or exchange. ASU 2021-04 provides guidance that 
will clarify whether an issuer should account for a modification or an exchange of a freestanding equity-classified written call option 
that remains equity classified after modification or exchange as (1) an adjustment to equity and, if so, the related earnings per share 
(EPS) effects, if any, or (2) an expense and, if so, the manner and pattern of recognition. The adoption of ASU 2021-04 did not have an 
effect on the Company’s consolidated financial statements. 

In March 2020, the FASB issued ASU No. 2020-04 Reference Rate Reform (Topic 848): Facilitation of the Effects of Reference Rate 
Reform  on  Financial  Reporting that  provides  optional  expedients  for  a  limited  period  of  time  for  accounting  for  contracts,  hedging 
relationships, and other transactions affected by the London Interbank Offered Rate (“LIBOR”) or other reference rates expected to be 
discontinued. These optional expedients can be applied from March 2020 through December 31, 2022.  In December 2022, the FASB 
issued ASU No. 2022-06 Reference Rate Reform (Topic 848): Deferral of the Sunset Date of Topic 848 which deferred the sunset date of 
Topic 848 from December 31, 2022 to December 31, 2024.  Debt arrangements that were entered into during the year ended December 
31, 2022, including the new term loans expiring in November 2028 and the new revolving credit facilities expiring in November 2024, 
no longer use LIBOR as a reference rate. LIBOR continues to be the reference rate for our trust preferred subordinated debt with maturity 
dates ranging from December 2032 through January 2034.  The phase out of LIBOR reference rates for our subordinated debt will occur 
beginning  in  June 2023.  The  Company’s adoption  of  this new  standard occurred during  the  year  ended  December 31,  2022,  prior  to 
the phase-out of the LIBOR reference rate. There was no material impact to the Company’s consolidated financial statements, nor do we 
expect the adoption of this standard to have a material impact on the consolidated financial statements during the LIBOR transition period. 

(b) 

Accounting Standards Not Yet Adopted: 

In June 2016, the  FASB issued ASU  2016-13, Financial Instruments-Credit  Losses (Topic 326):  Measurement of Credit  Losses on 
Financial Instruments (“ASU 2016-13”). ASU 2016-13 replaces the current incurred loss model used to measure impairment losses 
with an expected loss model for trade, reinsurance, and other receivables as well as financial instruments measured at amortized cost. 
ASU 2016-13 will require a financial asset measured at amortized cost, including reinsurance balances recoverable, to be presented at 
the net amount expected to be collected by means of an allowance for credit losses that runs through net income (loss). Credit losses 
relating to available-for-sale debt securities will also be recorded through an allowance for credit losses. However, the amendments 
would limit the amount of the allowance to the amount by which fair value is below amortized cost. The measurement of credit losses 
on available-for-sale investments is similar under current GAAP, but the update requires the use of the allowance account through which 
amounts can be reversed, rather than through irreversible write-downs. On November 15, 2019, the FASB issued ASU 2019-10, which 
(1) provides a framework to stagger effective dates for future major accounting standards and (2) amends the effective dates for certain 
major new accounting standards to give implementation relief to certain types of entities. Specifically, per ASU 2019-10 the Company 
would adopt ASU 2016-13 beginning January 1, 2023, as the Company is a smaller reporting company.  The Company’s service fee 
receivable and other receivables are within the scope of ASU 2016-13, however the Company does not anticipate the impact of adopting 
this standard will be material to its consolidated financial statements. 

NOTE 4 ACQUISITIONS  

(a) 

Business Combinations 

During the years ended December 31, 2022 and December 31, 2021, the Company incurred acquisition expenses related to business 
combinations of  $1.1  million  and $0.4  million,  respectively,  which  are  included  in  general  and  administrative  expenses  in  the 
consolidated statements of operations. 

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KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

CSuite Financial Partners, LLC 

On  November 1,  2022,  the  Company  acquired  100%  of  the  outstanding  equity  interests  of  CSuite Financial  Partners,  LLC 
(“CSuite”).   CSuite, based  in  Manhattan  Beach,  California,  is  a  national  financial  executive  services  firm  providing  financial 
management leadership to companies in every industry, regardless of size, throughout the United States.  As further discussed in Note 
22, “Segmented Information,” CSuite is included in the Kingsway Search Xcelerator segment.  This acquisition was the Company’s 
second acquisition under its novel CEO Accelerator program and further expands the Company’s portfolio of businesses with recurring 
revenue and low capital intensity. 

The  Company  acquired  CSuite  for  aggregate  cash  consideration  of  approximately  $8.5  million,  less  certain  escrowed  amounts  for 
purposes of indemnification claims and working capital adjustments.  The Company will also pay additional contingent consideration, 
only to the extent earned, in an aggregate amount of up to $3.6 million, which is subject to certain conditions, including the successful 
achievement of certain financial metrics for CSuite during the three-year period commencing on the first full calendar month following 
the acquisition date.   

This acquisition was accounted for as a business combination using the acquisition method of accounting.  The purchase price was 
provisionally allocated to the assets acquired and liabilities assumed based on their estimated fair values at the date of acquisition and 
are subject to adjustment during a measurement period subsequent to the acquisition date, not to exceed one-year as permitted under 
U.S. GAAP.  The Company expects to complete its purchase price allocation in early 2023.  These estimates, allocations and calculations 
are subject to change as we obtain further information; therefore, the final fair values of the assets acquired and liabilities assumed could 
change from the estimates included in these consolidated financial statements. 

Refer  to  Note  9,  “Intangible  Assets,”  for  further  disclosure  of  the  intangible  assets  related  to  this  acquisition.   The  goodwill 
of $4.1 million represents the premium paid over the fair value of the net tangible and intangible assets acquired, which the Company 
paid  to grow  its  portfolio  of companies  and  acquire  an  assembled workforce. The goodwill  is  not deductible  for  tax  purposes.  The 
estimated  fair  value  of  the contingent  consideration obligation  at  the  acquisition  date  of  zero was  determined  using  a  Monte  Carlo 
simulation based on forecasted future results.  

The following table summarizes the preliminary estimated allocation of the CSuite assets acquired and liabilities assumed at the date 
of acquisition: 

(in thousands) 

Cash and cash equivalents 
Service fee receivable 
Other receivables 
Goodwill 
Intangible asset not subject to amortization - trade name 
Intangible asset subject to amortization - customer relationships 
Other assets 
Total assets 

Accrued expenses and other liabilities 
Total liabilities 

Purchase price 

 November 1, 2022  
569   
  $ 
311   
21   
4,109   
1,500   
2,500   
53   
9,063   

  $ 

  $ 
  $ 

  $ 

539   
539   

8,524   

The consolidated statements of operations include the earnings of CSuite from the date of acquisition. From the date of acquisition 
through December 31, 2022, CSuite earned revenue of $1.3 million and had a net loss of less than $0.1 million. 

Secure Nursing Service, Inc. 

On November 18, 2022, the Company acquired substantially all of the assets and assumed certain specified liabilities of Secure Nursing 
Service, Inc. (“SNS”) for aggregate cash consideration of $11.5 million, less certain escrowed amounts for purposes of indemnification 
claims and working capital adjustments.  SNS, based in Los Angeles, California, employs highly skilled and professional per diem and 
travel Registered Nurses, Licensed Vocational Nurses, Certified Nurse Assistants and Allied Healthcare Professionals with multiple years 
of acute care hospital experience.  SNS places these healthcare professionals in both per diem assignments, and in short-term and long-

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KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

term travel assignments in a variety of hospitals in southern California. As further discussed in Note 22, “Segmented Information,” SNS 
is  included  in  the  Kingsway  Search  Xcelerator  segment.  This  acquisition  was  the  Company’s  third acquisition  under  its  novel  CEO 
Accelerator program and further expands the Company’s portfolio of businesses with recurring revenue and low capital intensity. 

This acquisition was accounted for as a business combination using the acquisition method of accounting.  The purchase price was 
provisionally allocated to the assets acquired and liabilities assumed based on their estimated fair values at the date of acquisition and 
are subject to adjustment during a measurement period subsequent to the acquisition date, not to exceed one-year as permitted under 
U.S. GAAP.  The Company expects to complete its purchase price allocation in early 2023.  These estimates, allocations and calculations 
are subject to change as we obtain further information; therefore, the final fair values of the assets acquired and liabilities assumed could 
change from the estimates included in these consolidated financial statements. 

Refer to Note 9, “Intangible Assets,” for further disclosure of the intangible assets related to this acquisition.  The goodwill of $1.6 
million represents the premium paid over the fair value of the net tangible and intangible assets acquired, which the Company paid to 
grow its portfolio of companies and acquire an assembled workforce. The goodwill is not deductible for tax purposes.   

The  following  table  summarizes  the  preliminary  estimated  allocation of  the  SNS  assets  acquired  and  liabilities  assumed at  the date 
of acquisition: 

(in thousands) 

Service fee receivable 
Goodwill 
Intangible asset not subject to amortization - trade name 
Intangible asset subject to amortization - customer relationships 
Other assets 
Total assets 

Accrued expenses and other liabilities 
Total liabilities 

Purchase price 

  $ 

November 18, 2022   
3,200   
1,600   
3,100   
3,600   
6   
11,506   

  $ 

  $ 
  $ 

  $ 

6   
6   

11,500   

The  consolidated  statements  of  operations  include  the  earnings  of  SNS  from  the  date  of  acquisition.  From  the  date  of  acquisition 
through December 31, 2022, SNS earned revenue of $2.4 million and had a net loss of $0.1 million. 

Ravix Financial, Inc. 

On October 1, 2021, the Company acquired 100% of the outstanding equity interests of Ravix Financial, Inc. (“Ravix”).  Ravix, based 
in  San  Jose,  California,  provides  outsourced  financial  services  and  human  resources  consulting  for  short  or  long  duration 
the  Kingsway  Search 
in  Note  22,  “Segmented  Information,”  Ravix is 
engagements.  As  further  discussed 
Xcelerator segment, which was created as a result of the Ravix acquisition.  This acquisition was the Company’s first acquisition under 
its novel CEO Accelerator program and further expands the Company’s portfolio of businesses with recurring revenue and low capital 
intensity. 

included 

in 

The  Company  acquired  Ravix  for  aggregate  cash  consideration  of  approximately  $10.9  million,  less  certain  escrowed  amounts  for 
purposes  of  indemnification  claims.   The  final  purchase  price  was subject  to  a  working  capital  true-up  of  $0.1  million  that  was 
settled during the first quarter of 2022. The Company will also pay additional contingent consideration, only to the extent earned, in an 
aggregate amount of up to $4.5 million, which is subject to certain conditions, including the successful achievement of gross profit for 
Ravix during the three-year period commencing on the first full calendar month following the acquisition date. During 2022, Ravix 
made a cash earn-out payment of $0.8 million.   

This acquisition was accounted for as a business combination using the acquisition method of accounting.  The purchase price was 
provisionally allocated to the assets acquired and liabilities assumed based on their estimated fair values at the date of acquisition and 
were subject to adjustment during a measurement period subsequent to the acquisition date, not to exceed one-year as permitted under 
U.S. GAAP.  During the first quarter of 2022, the Company finalized its fair value analysis of the assets acquired and liabilities assumed 
with the assistance of a third-party.  No measurement period adjustments were recorded as a result of finalizing the fair value analysis. 

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KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

Refer to Note 9, “Intangible Assets,” for further disclosure of the intangible assets related to this acquisition.  The goodwill of $7.9 
million represents the premium paid over the fair value of the net tangible and intangible assets acquired, which the Company paid to 
grow its portfolio of companies and acquire an assembled workforce. The goodwill is not deductible for tax purposes.  The estimated 
fair  value  of  the contingent  consideration obligation  at  the  acquisition  date  of $2.2  million was  determined  using  a  Monte  Carlo 
simulation based on forecasted future results. See Note 23, “Fair Value of Financial Instruments,” for further discussion related to the 
contingent consideration. 

The following table summarizes the purchase price of Ravix: 

(in thousands) 
Purchase price: 
Cash paid at closing 
Working capital adjustment 
Contingent consideration 
Total purchase price 

   October 1, 2021   
10,930   
  $ 
83   
2,195   
13,208   

  $ 

The following table summarizes the estimated allocation of the Ravix assets acquired and liabilities assumed at the date of acquisition: 

(in thousands) 

Cash and cash equivalents 
Restricted cash 
Service fee receivable 
Other receivables 
Right-of-use asset 
Goodwill 
Intangible asset subject to amortization - customer relationships 
Intangible asset not subject to amortization - trade name 
Other assets 
Total assets 

Accrued expenses and other liabilities 
Income taxes payable 
Lease liability 
Net deferred income tax liabilities 
Total liabilities 

Purchase price 

   October 1, 2021   
225   
  $ 
752   
1,031   
17   
116   
7,905   
4,000   
2,500   
133   
16,679   

  $ 

  $ 

  $ 

  $ 

1,546   
13   
116   
1,796   
3,471   

13,208   

The  consolidated  statements  of  operations  include  the  earnings  of  Ravix  from  the  date  of  acquisition.  From  the  date  of  acquisition 
through December 31, 2021, Ravix earned revenue of $3.5 million and had a net loss of $0.2 million. 

PWI Holdings, Inc. 

On December 1, 2020, the Company acquired 100% of the outstanding shares of PWI Holdings, Inc. This acquisition was accounted for 
as a business combination using the acquisition method of accounting.  The purchase price was provisionally allocated to the assets 
acquired and liabilities assumed based upon their estimated fair values at the date of acquisition and were subject to adjustment during 
a measurement period subsequent to the acquisition date, not to exceed one-year as permitted under U.S. GAAP.   During the third 
quarter  of  2021,  the  Company finalized its  fair  value  analysis  of  the  assets  acquired  and  liabilities  assumed  with  the  assistance  of 
a third-party.  

The Company records measurement period adjustments in the period in which the adjustments occur.  During the third quarter of 2021, 
the  Company  recorded  a  cumulative  net measurement  period  adjustment of $18.8  million  compared  to  the  amount  recorded  at 
December 31,  2020. The  measurement  period  adjustments reflected  changes  in  the  estimated  fair  values  of  certain  assets  and 
liabilities, and the working capital true-up. 

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KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

The measurement period adjustments resulted in an increase in amortization expense of $1.9 million related to the customer relationships 
intangible asset and a decrease to service fee and commission revenue of $1.9 million, both of which were recorded during the third 
quarter of 2021. 

Unaudited Pro Forma Summary 

The following unaudited pro forma summary presents the Company’s consolidated financial statements for the year ended December 31, 
2022 and December 31, 2021 as if CSuite, SNS and Ravix had been acquired on January 1 of the year prior to the acquisitions. The pro 
forma summary is presented for illustrative purposes only and does not purport to represent the results of our operations that would have 
actually occurred had the acquisitions occurred as of the beginning of the period presented or project our results of operations as of any 
future date or for any future period, as applicable. The pro forma results primarily include purchase accounting adjustments related to 
the acquisitions of CSuite, SNS and Ravix, interest expense and the amortization of debt issuance costs and discount associated with the 
related financing obtained in connection with the CSuite, SNS and Ravix acquisitions (see Note 12, “Debt”), tax related adjustments 
and acquisition-related expenses.  

(in thousands, except per share data) 

Revenues 
Income (loss) from continuing operations attributable to common shareholders 
Basic earnings (loss) per share - continuing operations 
Diluted earnings (loss) per share - continuing operations 

Years ended December 31, 
2021 
$ 113,342 
$ (4,439) 
$ (0.20) 
$ (0.20) 

2022   
$ 121,789   
$ 35,009   
$ 1.52   
$ 1.40   

(b) 

Asset Acquisition 

 VA Lafayette, LLC (formerly RoeCo Lafayette, LLC) 

On  December  30,  2021,  the  Company  acquired  100%  of  the  outstanding  membership  interests  of  RoeCo  Lafayette, 
LLC (“RoeCo”) from a current holder of the Company’s Preferred Shares, for cash consideration of approximately $2.4 million.  Refer 
to Note 24, “Related Parties,” for further disclosure.  In 2022, RoeCo changed its name to VA Lafayette, LLC (“VA Lafayette”).  VA 
Lafayette owns real property consisting of approximately 6.5 acres and a 29,224 square foot single-tenant medical office building located 
in the State of Louisiana (the “LA Real Property”). The LA Real Property serves as a medical and dental clinic for the Department of 
Veteran Affairs and is subject to a long-term lease.  The LA Real Property is also subject to a mortgage in the principal amount of 
$13.5 million (the “LA Mortgage”) at the date of acquisition plus a premium of $3.5 million. 

The acquisition was accounted for as an asset acquisition as substantially all the fair value of the gross assets acquired is concentrated 
in a single asset comprised of land, building and improvements.  The total purchase price, including the transaction costs, was allocated 
to the individual net assets acquired based on their relative fair values.  In connection with the acquisition, the Company recorded an 
above-market lease intangible asset of $0.8 million and in-place and other lease intangible assets of $2.1 million.  

The following table summarizes the allocation of the purchase price to the net assets of VA Lafayette at the date of acquisition:  

(in thousands) 
Purchase price: 
Cash 
Acquisition costs 
Liabilities assumed 
Total purchase price 

Fair value of net assets acquired: 
Cash and cash equivalents 
Other receivables 
Property and equipment, net 
Intangible asset subject to amortization - Above-market lease 
Intangible asset subject to amortization - In-place and other lease assets 
Accrued expenses and other liabilities 
Net deferred income tax liabilities 
Total fair value of net assets acquired 

64 

December 30, 2021   
2,386   
   $ 
249   
16,983   
19,618   

   $ 

December 30, 2021   
365   
   $ 
133   
16,466   
835   
2,114   
(50 ) 
(245 ) 
19,618   

   $ 

  
  
  
  
  
  
  
  
  
  
  
  
    
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

Since VA Lafayette was acquired on December 30, 2021, the consolidated statement of operations for the year ended December 31, 
2021 did not include any revenue or earnings of VA Lafayette, as such items are immaterial.   

During  the  fourth  quarter  of  2022,  the  Company  began executing a  plan  to sell  VA  Lafayette,  and  as  a  result,  VA  Lafayette 
is reported as held for sale.  Further information is contained in Note 5, “Disposal and Discontinued Operations” to the consolidated 
financial statements. 

NOTE 5 DISPOSAL AND DISCONTINUED OPERATIONS 

(a)  Disposal 

Professional Warranty Service Corporation  

On July 29, 2022, Professional Warranty Services LLC (“PWS LLC”), a subsidiary of the Company entered into an Equity Purchase 
Agreement (the “Agreement”) with Professional Warranty Service Corporation (“PWSC”), an 80% majority-owned, indirect subsidiary 
of the Company, Tyler Gordy, the president of PWSC and a 20% owner of PWSC (“Gordy”) and PCF Insurance Services of the West, 
LLC (“Buyer”), pursuant to which PWS LLC and Gordy sold PWSC to Buyer.  

The purchase price paid  by Buyer  to  PWS  LLC and  Gordy  consisted of $51.2 million  in base purchase  price,  subject  to  customary 
adjustments for net working capital, and non-compensation related transaction expenses of approximately $1.7 million.  As a result of 
the  sale,  the  Company  incurred compensation  expenses  of  $5.4  million,  primarily related  to previously-granted awards  to PWSC 
employees  that  are  accounted  for  on  a  fair  value  basis, which  are  included  in  disposal  of  subsidiary  transaction  expenses  in  the 
consolidated statement of operations for the year ended December 31, 2022. 

To the extent the EBITDA of PWSC (as defined in the Agreement) for the one-year period following the sale transaction exceeds 103% 
of the EBITDA at the closing of the sale transaction (the “Closing EBITDA”), PWS LLC and Gordy will also be entitled to receive an 
earnout payment in an amount equal to five times the EBITDA in excess of 103% of Closing EBITDA.  The Company does not have 
access to the information needed to reasonably estimate the potential earnout payment and accordingly any gain related to the earnout 
payment will be recorded in the period the consideration is determined to be realizable. 

As a result of the sale, the Company recognized a net gain on disposal of $37.9 million, net of direct selling costs of $1.7 million, during 
the  year  ended December  31,  2022.   The  sale  of  PWSC did  not  represent  a strategic  shift that  would have  a  major  effect  on  the 
Company’s operations or financial results; therefore, PWSC is not presented as a discontinued operation.  The earnings of PWSC, which 
is included in the Extended Warranty segment, are included in the consolidated statements of operations through the July 29, 2022 disposal 
date.  The assets, liabilities and equity (including the non-controlling interest) of PWSC were deconsolidated effective July 29, 2022. 

The sale of PWSC represents the disposal of a significant subsidiary of the Company, that had contributions to Extended Warranty 
service fee and commission revenue of $4.9 million and $8.0 million for the years ended December 31, 2022 and December 31, 2021, 
respectively.   Additionally,  PWSC  had  a  pre-tax  loss of $5.5  million  for  the year ended  December  31,  2022 and  pre-tax  income  of 
$0.6 million for the for the year ended December 31, 2021.  For the years ended December 31, 2022 and December 31, 2021, pre-tax 
loss of $4.4 million and pre-tax income of $0.5 million was attributable to the controlling interest, respectively.  At the July 29, 2022 
disposal date, PWSC had service fee receivables totaling $0.7 million, intangible assets, net of $2.3 million, deferred service fees of 
$7.6 million and a non-controlling interest of ($2.2) million. 

As a result of the sale, the Company incurred additional compensation expenses of $5.4 million that are included in disposal of subsidiary 
transaction expenses in the consolidated statement of operations for the for the year ended December 31, 2022. 

(b)  Discontinued Operations 

Leased Real Estate Segment 

The Company’s subsidiaries, VA Lafayette and CMC Industries Inc. (“CMC”), which includes CMC’s subsidiaries Texas Rail Terminal 
LLC and TRT Leaseco, LLC (“TRT”), comprised the Company’s entire Leased Real Estate segment.  Each of CMC, through indirect 
wholly owned subsidiary, TRT, and VA Lafayette own a single asset, which is real estate property.  As further described below, on 
December 29, 2022, TRT sold its assets and at December 31, 2022, VA Lafayette was classified as held for sale.  

65 

  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

In  accordance  with  ASU No.  2014-08, Reporting  of  Discontinued  Operations  and  Disclosures  of  Disposals  of  Components  of  an 
Entity, a disposal is categorized as a discontinued operation if the disposal group is a component of an entity or group of components 
that meets the held for sale criteria, is disposed of by sale, or is disposed of other than by sale, and represents a strategic shift that has or 
will have a major effect on an entity’s operations and financial results. 

Leased Real Estate is a component of Kingsway since its operations and cash flows can be clearly distinguished, both operationally and 
for financial reporting purposes, from the rest of the reporting entity.  A component of an entity may consist of multiple disposal groups 
and  does  not  need  to  be  disposed  of  in  a  single  transaction.   The  disposal  of  the  Leased  Real  Estate segment  represents  a strategic 
shift that will have a major effect on the Company’s operations and financial results, as the disposal of the Leased Real Estate assets is 
in excess of 20% of the entity’s total assets.  As a result, the assets, liabilities, operating results and cash flows related to Leased Real 
Estate have been classified as discontinued operations in the consolidated financial statements for all periods presented. 

Sale of CMC Real Property 

CMC owned, through its indirect wholly owned subsidiary, TRT, a parcel of real property consisting of approximately 192 acres located 
in the State of Texas (the “Real Property”), which is subject to a long-term triple net lease agreement. The Real Property is also subject 
to two mortgages (the “Mortgages”). 

On  December  22,  2022,  TRT  entered  into  a  Purchase  and  Sale  Agreement  (the  “CMC  Agreement”)  with  BNSF  Dayton  LLC 
(“Purchaser”), pursuant to which TRT agreed to sell to the Purchaser the Real Property.  TRT was also the landlord and an affiliate of 
the Purchaser was the current tenant under the long-term triple net lease over the Real Property.  Under the terms of the CMC Agreement, 
at the closing on December 29, 2022, TRT assigned, and the Purchaser assumed, the rights and obligations of the landlord under the 
existing long-term triple net lease.   

The purchase price paid by the Purchaser at the closing consisted of $44.5 million in cash plus the assumption of the unpaid principal 
balance as of the closing of the Mortgages of approximately $170.7 million, netting cash proceeds of $21.4 million to Kingsway after 
taxes, fees and distribution to the minority shareholder.  The Company recognized a gain on disposal of CMC of $0.2 million which is 
included  in  loss  on  disposal  of  discontinued  operations,  net  of  taxes  in  the  consolidated  statement  of  operations  for  the  year 
ended December 31, 2022. 

As  discussed  above,  CMC  and  TRT  are  part  of  the  Leased  Real  Estate  disposal  group.    The  sale  of  the  Leased  Real  Estate’s 
assets represents a strategic shift that will have a major effect on the Company’s operations and financial results.  As a result, CMC and 
its subsidiaries, have been classified as a discontinued operation and the results of their operations are reported separately for all periods 
presented.  The  assets  and  liabilities  of  CMC  are  presented  as  discontinued  operations  in  the  consolidated  balance  sheet at 
December 31, 2021. 

VA Lafayette 

During the fourth quarter of 2022, the Company began executing a plan to sell its subsidiary, VA Lafayette.  VA Lafayette owns the LA 
Real Property, that is subject to a long-term lease and the LA Mortgage.   

As discussed above, VA Lafayette is part of the Leased Real Estate disposal group.   In conjunction with the sale of the CMC Real 
Property, the sale of the Leased Real Estate’s assets represents a strategic shift that will have a major effect on the Company’s operations 
and financial  results.  As  a result,  VA  Lafayette  has been classified  as  a discontinued  operation  and  the  results of  its operations  are 
reported separately for all periods presented. The assets and liabilities of VA Lafayette are presented as held for sale in the consolidated 
balance sheets at December 31, 2022 and December 31, 2021. 

Summary  financial  information  for  Leased  Real  Estate  included  in  (loss)  income  from  discontinued  operations,  net  of  taxes  in  the 
statements of operations for the years ended December 31, 2022 and December 31, 2021 is presented below: 

(in thousands) 

(Loss) income from discontinued operations, net of taxes: 
Revenues: 

Rental revenue 

Total revenues 

Years ended December 31,   
2021   

2022   

$ 

14,567   $ 
14,567     

13,365   
13,365   

66 

  
  
    
      
  
    
      
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

(in thousands) 

Expenses: 

Cost of services sold 
General and administrative expenses 
Leased real estate segment interest expense 
Non-operating other (expense) revenue 
Amortization of intangible assets 

Total expenses 
(Loss) income from discontinued operations before income tax benefit 
Income tax benefit 
(Loss) income from discontinued operations, net of taxes 

$ 

Years ended December 31,   
2021   

2022   

204     
20,778     
6,387     
154     
206     
27,729     
(13,162 )   
(357 )   
(12,805 ) $ 

—   
3,488   
6,164   
2,804   
63   
12,519   
846   
(3,728 ) 
4,574   

For the years ended December 31, 2022 and December 31, 2021, pre-tax loss from discontinued operations of $10.7 million and pre-tax 
income from discontinued operations of $0.7 million was attributable to the controlling interest, respectively.  

The assets and liabilities of Leased Real Estate are presented as held for sale and as discontinued operations in the consolidated balance 
sheets at December 31, 2022 and December 31, 2021. 

The carrying amounts of the major classes of assets and liabilities of Leased Real Estate presented as held for sale at December 31, 2022 
and December 31, 2021 are as follows: 

(in thousands) 
Assets 
Cash and cash equivalents 
Other receivables, net 
Property and equipment, net 
Intangible assets, net 
Assets held for sale 
Liabilities 
Accrued expenses and other liabilities 
Notes payable 
Liabilities held for sale 

December 31, 
2022 

December 31, 
2021 

  $ 

  $ 

  $ 

  $ 

570     $ 
—       
16,160       
2,748       
19,478     $ 

473     $ 
16,112       
16,585     $ 

365   
133   
16,466   
2,949   
19,913   

52   
16,983   
17,035   

The  carrying  amounts  of  the  major  classes  of  assets  and  liabilities  of  Leased  Real  Estate  presented  as  discontinued  operations at 
December 31, 2021 are as follows: 

(in thousands) 
Assets  
Cash and cash equivalents 
Other receivables, net 
Property and equipment, net 
Goodwill 
Intangible assets, net 
Other assets 
Assets of discontinued operations 
Liabilities 
Accrued expenses and other liabilities 
Notes payable 
Liabilities of discontinued operations 

67 

December 31, 
2021 

  $ 

  $ 

  $ 

  $ 

2,193   
9,733   
91,019   
60,983   
74,448   
11,096   
249,472   

2,596   
181,631   
184,227   

  
    
      
  
  
  
  
  
  
  
  
  
  
  
  
    
  
      
        
  
    
    
    
      
        
  
    
  
  
  
  
      
  
    
    
    
    
    
      
  
    
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

Mendota Insurance Company, Mendakota Insurance Company and Mendakota Casualty Company 

As  part  of  the  October  18,  2018  transaction  to  sell  Mendota  Insurance  Company,  Mendakota  Insurance  Company  and  Mendakota 
Casualty Company (collectively “Mendota”), the Company will indemnify the buyer for any loss and loss adjustment expenses with 
respect to open claims in excess of Mendota’s carried unpaid loss and loss adjustment expenses at June 30, 2018 related to the open 
claims. The maximum obligation to the Company with respect to the open claims is $2.5 million. Per the purchase agreement, a security 
interest on the Company’s equity interest in its consolidated subsidiary, Net Lease, as well as any distributions to the Company from 
Net Lease, was to be collateral for the Company’s payment of obligations with respect to the open claims. 

During the third quarter of 2021, the purchasers of Mendota and the Company agreed to release the Company’s equity interest in Net 
Lease as collateral and allow Net Lease to make distributions to the Company.  In exchange, the Company agreed to deposit $2.0 million 
into an escrow account and advance $0.5 million to the purchaser of Mendota to satisfy the Company’s payment obligation with respect 
to the open claims. 

During  the  third  quarter  of  2022, the  buyer  provided  to  the  Company  an  analysis  of  the  claims  development  that  indicated that 
the Company’s potential exposure with respect to the open claims was at the maximum obligation amount.  Previous communications 
from the buyer noted no such development and the buyer was not obligated to provide development information to the Company until 
the first quarter of 2023.  As a result of the newly provided information, the Company recorded a liability of $2.5 million, which is 
included  in  accrued  expenses  and  other  liabilities  in  the consolidated  balance  sheet  at December  31,  2022  and loss  on  disposal  of 
discontinued operations, net of taxes in the consolidated statement of operations for the year ended December 31, 2022.  There were no 
payments made by the Company related to the open claims during the years ended December 31, 2022 and December 31, 2021.  During 
the first quarter of 2023, the $2.0 million that had been previously deposited into an escrow account was released and remitted to the 
buyer to satisfy the Company’s payment with respect to the open claims.   

Loss on disposal of discontinued operations, net of taxes, related to Leased Real Estate and Mendota, in the statements of operations for 
the years ended December 31, 2022 and December 31, 2021 is comprised on the following: 

(in thousands) 

Loss on disposal of discontinued operations before income tax benefit 
Income tax benefit 
Loss on disposal of discontinued operations, net of taxes 

Years ended December 31,   
2021   
—   
—   
—   

2022     
(26,751 )     
(24,489 )     
(2,262 )   $ 

  $ 

NOTE 6 VARIABLE INTEREST ENTITIES 

(a)  

Consolidated VIEs 

Argo Holdings Fund I, LLC 

The  Company  holds a  43.4%  investment  in  Argo  Holdings  at  December  31,  2022  and  December  31,  2021.  Argo  Holdings  makes 
investments, primarily in established lower middle market companies based in North America, through investments in search funds. 
The managing member of Argo Holdings is Argo Management Group, LLC (“Argo Management”), a wholly owned subsidiary of the 
Company. Argo Holdings is considered to be a VIE as the members holding equity at risk lack characteristics of a controlling financial 
interest. The Company holds a variable interest in Argo Holdings due to its right to absorb significant economics in Argo Holdings and 
through its controlling interest in Argo Management, through which the Company holds the power to direct the significant activities of 
Argo Holdings. As such, the Company was the primary beneficiary of Argo Holdings and consolidated Argo Holdings at December 31, 
2022 and December 31, 2021. 

Net Lease Investment Grade Portfolio, LLC 

The Company holds a 71.0% investment in Net Lease at December 31, 2022 and December 31, 2021. Net Lease holds one commercial 
property under a triple net lease. The current property is encumbered by a mortgage loan.  Net Lease is considered to be a VIE as the 
members holding equity at risk lack characteristics of a controlling financial interest.  The Company holds a variable interest in Net 
Lease due to its right to absorb significant economics in Net Lease and to control the management decisions of Net Lease, which allows 
the Company to hold the power to direct the significant activities of Net Lease.  As such, the Company is the primary beneficiary of Net 
Lease and consolidated Net Lease at December 31, 2022 and December 31, 2021. 

68 

  
  
  
  
    
    
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

The  following  table  summarizes  the  assets  and  liabilities  related  to  VIEs  consolidated  by  the  Company  at  December  31,  2022  and 
December 31, 2021:      

(in thousands) 

Assets 
Limited liability investments, at fair value 
Cash and cash equivalents 
Accrued investment income 
Total Assets 
Liabilities 
Accrued expenses and other liabilities 
Total Liabilities 

2022     

December 31,   
2021   

  $ 

  $ 

17,059     $ 
573       
829       
18,461       

333       
333     $ 

18,826   
944   
716   
20,486   

250   
250   

No  arrangements  exist  requiring  the  Company  to  provide  additional  funding  to  the  consolidated  VIEs  in  excess  of  the  Company’s 
unfunded  commitments  to  its  consolidated  VIEs.  At  December  31,  2022  and  December  31,  2021,  the  Company  had  no  unfunded 
commitments.  There  are  no  restrictions  on  assets  consolidated  by  these  VIEs.  There  are  no  structured  settlements  of  liabilities 
consolidated by these VIEs. Creditors have no recourse to the general credit of the Company as the primary beneficiary of these VIEs. 

(b)  

Non-Consolidated VIEs 

The  Company’s  investments  include  certain  non-consolidated  investments,  primarily  in  limited  liability  companies  and  limited 
partnerships in which the Company holds variable interests, that are considered VIEs due to the legal entities holding insufficient equity; 
the holders of equity at risk in the legal entities lacking controlling financial interests; and/or the holders of equity at risk having non-
proportional voting rights. 

The  Company’s  risk  of  loss  associated  with  its  non-consolidated  VIEs  is  limited  and  depends  on  the  investment.  Limited  liability 
investments  accounted  for  under  the  equity  method  are  limited  to  the  Company’s  initial  investments.  At  December  31,  2022  and 
December 31, 2021, the Company had no unfunded commitments to its non-consolidated VIEs. 

The  following  table  summarizes  the  carrying  value  and  maximum  loss  exposure  of  the  Company’s  non-consolidated  VIEs  at 
December 31, 2022 and December 31, 2021: 

(in thousands) 

2022 

Carrying 
Value 

Maximum 
Loss 
Exposure 

December 31,   

2021 

Maximum 
Loss 
Exposure 

Carrying 
Value 

Investments in non-consolidated VIEs 

  $ 

940     $ 

940     $ 

1,514     $ 

1,514   

The following table summarizes the Company’s non-consolidated VIEs by category at December 31, 2022 and December 31, 2021: 

(in thousands) 

Investments in non-consolidated VIEs: 

Real estate related 
Non-real estate related 

Total investments in non-consolidated VIEs 

2022 

December 31,   

2021 

Carrying 
Value 

Percent of 
total 

Carrying 
Value 

Percent of 
total 

  $ 

  $ 

—       
940       
940       

— %   $ 
100.0 %     
100.0 %   $ 

628       
886       
1,514       

41.5 % 
58.5 % 
100.0 % 

69 

                                                  
  
  
  
      
        
  
    
    
    
      
        
  
    
  
  
  
  
  
  
  
    
  
  
  
    
    
    
  
  
  
  
  
  
     
  
  
  
    
     
    
  
      
        
         
        
  
    
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

The following table presents aggregated summarized financial information of the Company’s non-consolidated VIEs at December 31, 
2022 and December 31, 2021. For certain of the non-consolidated VIEs, the financial information is presented on a lag basis, consistent 
with how the changes in the Company’s share of the net asset values of these equity method investees are recorded in net investment 
income. The difference between the end of the reporting period of an equity method investee and that of the Company is typically no 
more than three months. 

(in thousands) 

Assets 
Liabilities 
Equity 

(in thousands) 

Net income 

NOTE 7 INVESTMENTS 

2022     
241,050     $ 
330,470     $ 
(89,420 )   $ 

December 31,   
2021   
283,432   
299,340   
(15,908 ) 

2022     
16,330     $ 

December 31,   
2021   
18,647   

  $ 
  $ 
  $ 

  $ 

The  amortized  cost,  gross  unrealized  gains  and  losses,  and  estimated  fair  value  of  the  Company’s  available-for-sale  investments  at 
December 31, 2022 and December 31, 2021 are summarized in the tables shown below: 

(in thousands) 

Fixed maturities: 

U.S. government, government agencies and authorities 
States, municipalities and political subdivisions 
Mortgage-backed 
Asset-backed 
Corporate 

Total fixed maturities 

(in thousands) 

Gross 

   Amortized     
Cost     

Unrealized     
Gains     

Gross 

December 31, 2022   
Estimated 
Fair   
Value   

Unrealized     
Losses     

  $ 

  $ 

15,797     $ 
2,390       
9,058       
1,682       
11,200       
40,127     $ 

—     $ 
—       
1       
—       
1       
2     $ 

717     $ 
158       
647       
72       
944       
2,538     $ 

15,080   
2,232   
8,412   
1,610   
10,257   
37,591   

Gross 

   Amortized     
Cost     

Unrealized     
Gains     

Gross 

December 31, 2021   
Estimated 
Fair   
Value   

Unrealized     
Losses     

Fixed maturities: 

U.S. government, government agencies and authorities 
States, municipalities and political subdivisions 
Mortgage-backed 
Asset-backed 
Corporate 

Total fixed maturities 

  $ 

  $ 

16,276     $ 
1,880       
7,679       
449       
9,605       
35,889     $ 

31     $ 
3       
18       
—       
15       
67     $ 

84     $ 
5       
68       
4       
129       
290     $ 

16,223   
1,878   
7,629   
445   
9,491   
35,666   

70 

  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
      
        
        
        
  
    
    
    
    
  
  
  
  
  
      
        
        
        
  
    
    
    
    
  
 
 
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

The table below summarizes the Company’s fixed maturities at December 31, 2022 by contractual maturity periods. Actual results may 
differ  as  issuers  may  have  the  right  to  call  or  prepay  obligations,  with  or  without  penalties,  prior  to  the  contractual  maturity  of 
these obligations. 

(in thousands) 

Due in one year or less 
Due after one year through five years 
Due after five years through ten years 
Due after ten years 
Total 

   Amortized Cost     
  $ 

December 31, 2022   
       Estimated Fair   
Value   
7,034   
24,628   
1,982   
3,947   
37,591   

7,163     $ 
26,317       
2,239       
4,408       
40,127     $ 

  $ 

The following tables highlight the aggregate unrealized loss position, by security type, of available-for-sale investments in unrealized 
loss positions as of December 31, 2022 and December 31, 2021. The tables segregate the holdings based on the period of time the 
investments have been continuously held in unrealized loss positions. 

(in thousands) 

December 31, 2022   

Less than 12 Months 

     Greater than 12 Months 

Total 

   Estimated 
   Fair Value      

     Unrealized       Estimated 

     Unrealized       Estimated 

Loss 

     Fair Value      

Loss 

     Fair Value      

     Unrealized    
Loss 

Fixed maturities: 

U.S. government, government 
agencies and authorities 
States, municipalities and political 
subdivisions 
Mortgage-backed 
Asset-backed 
Corporate 

Total fixed maturities 

  $ 

(in thousands) 

  $ 

4,543     $ 

126     $ 

10,537     $ 

591     $ 

15,080     $ 

717   

1,040       
2,248       
1,251       
3,244       
12,326     $ 

73       
93       
39       
155       
486     $ 

937       
5,756       
299       
6,760       
24,289     $ 

85       
554       
33       
789       
2,052     $ 

1,977       
8,004       
1,550       
10,004       
36,615     $ 

158   
647   
72   
944   
2,538   

Less than 12 Months 

     Greater than 12 Months 

Total 

December 31, 2021   

   Estimated 
   Fair Value      

     Unrealized       Estimated 

     Unrealized       Estimated 

Loss 

     Fair Value      

Loss 

     Fair Value      

     Unrealized    
Loss 

Fixed maturities: 

U.S. government, government 
agencies and authorities 
States, municipalities and political 
subdivisions 
Mortgage-backed 
Asset-backed 
Corporate 

Total fixed maturities 

  $ 

  $ 

12,077     $ 

84     $ 

—     $ 

—     $ 

12,077     $ 

846       
5,388       
445       
7,542       
26,298     $ 

5       
68       
4       
129       
290     $ 

—       
—       
—       
—       
—     $ 

—       
—       
—       
—       
—     $ 

846       
5,388       
445       
7,542       
26,298     $ 

84   

5   
68   
4   
129   
290   

There are approximately 208 and 138 individual available-for-sale investments that were in unrealized loss positions as of December 31, 
2022 and December 31, 2021, respectively.  

The  establishment  of  an  other-than-temporary  impairment  on  an investment  requires  a  number  of  judgments  and  estimates.  The 
Company performs a quarterly analysis of the individual investments to determine if declines in market value are other-than-temporary. 
Refer  to  “Significant  Accounting  Policies  and  Critical  Estimates”  section  of  Management’s  Discussion  &  Analysis  for  further 
information regarding the Company’s detailed analysis and factors considered in establishing an other-than-temporary impairment on 
an investment. 

71 

  
  
  
    
  
    
    
    
  
  
    
        
        
        
      
  
  
    
  
  
  
  
      
        
        
        
        
        
  
    
    
    
    
  
    
        
        
        
      
  
  
    
  
  
  
  
      
        
        
        
        
        
  
    
    
    
    
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

As a result of the analysis performed by the Company to determine declines in market value that are other-than-temporary, the Company 
did  not  record  any  write-downs  for  other-than-temporary  impairment  related  to available-for  sale  investments,  limited  liability 
investments, investments in private companies and other investments for the years ended December 31, 2022 and December 31, 2021.   

The Company has reviewed currently available information regarding investments with estimated fair values less than their carrying 
amounts and believes these unrealized losses are not other-than-temporary and are primarily due to temporary market and sector-related 
factors rather than to issuer-specific factors. The Company does not intend to sell those investments, and it is not likely it will be required 
to sell those investments before recovery of its amortized cost. 

The Company does not have any exposure to subprime mortgage-backed investments. 

As  of  December  31,  2022  and  December  31,  2021,  the  carrying  value  of  limited  liability  investments  totaled  $1.0 million  and 
$1.9 million, respectively. At December 31, 2022, the Company has no unfunded commitments related to limited liability investments.   

Limited liability investments, at fair value represents the underlying investments of the Company’s consolidated entities Net Lease and 
Argo Holdings.  As of December 31, 2022 and December 31, 2021, the carrying value of the Company’s limited liability investments, 
at  fair  value  was $17.1  million and $18.8 million,  respectively.  The  Company  recorded  impairments  related  to  limited  liability 
investments, at fair value of less than $0.1 million and $0.1 million for the years ended December 31, 2022 and December 31, 2021, 
respectively, which are included in (loss) gain on change in fair value of limited liability investments, at fair value in the consolidated 
statements of operations. At December 31, 2022, the Company has no unfunded commitments related to limited liability investments, 
at fair value. 

The Company consolidates the financial statements of Net Lease on a three-month lag. Net Lease owns investments in limited liability 
companies that hold investment properties. 

•  During 2021, one of Net Lease’s limited liability companies sold their investment property for $14.3 million.  A portion of the 
proceeds from the sale were distributed to Net Lease.  As a result of the distribution, Net Lease recorded a gain of $0.8 million 
related to its investment in the limited liability company, with an offsetting change in unrealized gain of $0.8 million, which 
collectively  are  included  in  net  investment  income  in  the  consolidated  statement  of  operations  for  the year  ended 
December 31, 2021.  

•  During the fourth quarter of 2020, one of Net Lease’s limited liability companies sold their investment property.  As a result 
of the three-month lag, the Company recorded this transaction in its first quarter 2021 financial statements.  A portion of the 
proceeds from the sale were distributed to Net Lease who used them primarily to repay their $9.0 million mezzanine loan. As 
a result of the distribution, Net Lease recorded a gain of $1.2 million related to its investment in the limited liability company, 
with an offsetting change in unrealized gain of $1.2 million, which collectively are included in net investment income in the 
consolidated statement of operations for the for the year ended December 31, 2021.  

•  Net Lease sold its final property in February 2023.  

As of December 31, 2022 and December 31, 2021, the carrying value of the Company’s investments in private companies totaled $0.8 
million. For the years ended December 31, 2022 and December 31, 2021, the Company did not record any adjustments to the fair value 
of its investments in private companies for observable price changes. 

The Company performs a quarterly impairment analysis of its investments in private companies. As a result of the analysis performed, 
the Company did not record any impairments related to investments in private companies for the years ended December 31, 2022 and 
December 31, 2021. 

Real  estate  investments represent investment  real  estate  properties  held  by  the  Company’s  consolidated  subsidiary,  Flower.   As  of 
December 31, 2022 and December 31, 2021, the carrying value of the Company’s real estate investments was zero and $10.7 million, 
respectively.  The Company consolidates the financial statements of Flower on a three-month lag.  On September 29, 2022, Flower sold 
their investment real estate properties for $12.2 million.  A portion of the proceeds from the sale were used to repay the Flower note 
payable with an unpaid principal balance of $5.9 million at the transaction date.  Flower recorded a gain of $1.5 million related to the 
sale, which is included in gain on change in fair value of real estate investments in the consolidated statement of operations for the year 
ended December 31, 2022.   

72 

  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

Net investment income for the years ended December 31, 2022 and December 31, 2021, respectively, is comprised as follows: 

(in thousands) 

Investment income 

Interest from fixed maturities 
Dividends 
Income from limited liability investments 
Income from limited liability investments, at fair value 
Income from real estate investments 
Other 

Gross investment income 
Investment expenses 
Net investment income 

Years ended December 31,   
2021   

2022     

  $ 

  $ 

556     $ 
159       
293       
4       
795       
612       
2,419       
(114 )     
2,305     $ 

242   
125   
27   
106   
800   
364   
1,664   
(89 ) 
1,575   

Gross realized gains and losses on available-for-sale investments, limited liability investments, limited liability investments, at fair value 
and investments in private companies for the years ended December 31, 2022 and December 31, 2021 is comprised as follows: 

(in thousands) 

Gross realized gains 
Gross realized losses 
Net realized gains 

Years ended December 31,   
2021   
1,917   
(108 ) 
1,809   

2022     
1,648     $ 
(439 )     
1,209     $ 

  $ 

  $ 

(Loss) gain on change in fair value of equity investments for the years ended December 31, 2022 and December 31, 2021 is comprised 
as follows: 

(in thousands) 

Net gain recognized on equity investments sold during the period 
Change in unrealized losses on equity investments held at end of the period 
Loss on change in fair value of equity investments 

  $ 

  $ 

2022     

Years ended December 31,   
2021   
13   
(255 ) 
(242 ) 

—     $ 
(26 )     
(26 )   $ 

NOTE 8 GOODWILL 

The following table summarizes goodwill activity for the years ended December 31, 2022 and December 31, 2021: 

(in thousands) 
Balance, December 31, 2020 
Acquisition 
Measurement period adjustment 
Balance, December 31, 2021 
Acquisitions 
Goodwill disposed of related to PWSC 
Balance, December 31, 2022 

Extended 
Warranty 

Kingsway 
Search 

Xcelerator       Corporate      

Total 

  $ 

  $ 

59,415     $ 
—       
(18,788 )     
40,627       
—       
(9,474 )     
31,153     $ 

—     $ 
7,905       
—       
7,905       
5,708       
—       
13,613     $ 

732     $ 
—       
—       
732       
—       
—       
732     $ 

60,147   
7,905   
(18,788 ) 
49,264   
5,708   
(9,474 ) 
45,498   

As further discussed in Note 4, “Acquisitions,” during 2022, the Company recorded goodwill of $4.1 million related to the acquisition 
of CSuite on November 1, 2021 and $1.6 million related to the acquisition of SNS on November 18, 2022.  The goodwill related to 
these acquisitions  is  provisional  and  subject  to  adjustment  during  the  measurement  period.   The  Company  expects  to  complete  its 
purchase  price  allocations  in  early  2023.  The  estimates,  allocations  and  calculations  recorded  at  December  31,  2022  are  subject  to 

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KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

change as we obtain further information; therefore, the final fair values of the assets acquired and liabilities assumed may not agree with 
the estimates included in these consolidated financial statements.  

As further discussed in Note 4, “Acquisitions,” during 2021, the Company recorded goodwill of $7.9 million related to the acquisition 
of Ravix on October 1, 2021.   

In 2020, the Company recorded goodwill of $39.0 million related to the acquisition of PWI on December 1, 2020 which was provisional 
and subject to adjustment during the measurement period.  As further discussed in Note 4, “Acquisitions,” during the third quarter of 
2021, the  Company recorded  a  cumulative  net measurement  period  adjustment,  related to  the  acquisition  of  PWI,  that  decreased 
goodwill by $18.8 million.   

Goodwill is assessed for impairment annually as of November 30, or more frequently if events or circumstances indicate that the carrying 
value may not be recoverable. Although the Company believes its estimates of fair value are reasonable, actual financial results could 
differ from those estimates due to the inherent uncertainty involved in making such estimates. Changes in assumptions concerning future 
financial  results  or other  underlying  assumptions  could have  a significant  impact on  either  the  fair  value  of  the  reporting units,  the 
amount of the goodwill impairment charge, or both.  Based on the assessment performed, no goodwill impairments were recognized 
in 2022 and 2021. 

NOTE 9 INTANGIBLE ASSETS 

Intangible assets at December 31, 2022 and December 31, 2021 are comprised as follows: 

(in thousands) 

Intangible assets subject to amortization 

Database 
Vehicle service agreements in-force 
Customer relationships 

Intangible assets not subject to amortization 

Trade names 

Total 

(in thousands) 

Intangible assets subject to amortization 

Database 
Vehicle service agreements in-force 
Customer relationships 
Non-compete 

Intangible assets not subject to amortization 

Trade names 

Total 

   Gross Carrying       Accumulated 
     Amortization 

Value 

December 31, 2022   
     Net Carrying 

Value 

  $ 

  $ 

4,918     $ 
3,680       
32,442       

14,287       
55,327     $ 

4,918     $ 
3,680       
13,630       

—       
22,228     $ 

—   
—   
18,812   

14,287   
33,099   

   Gross Carrying       Accumulated 
     Amortization 

Value 

December 31, 2021   
     Net Carrying 

Value 

  $ 

  $ 

4,918     $ 
3,680       
31,645       
266       

10,314       
50,823     $ 

4,488     $ 
3,680       
11,598       
224       

—       
19,990     $ 

430   
—   
20,047   
42   
—   
10,314   
30,833   

As  discussed  in Note  5,  “Disposal  and  Discontinued  Operations,”  the  Company  disposed  of PWSC  on  July  29,  2022.   PWSC  had 
intangible assets with a gross carrying value of $6.2 million and a net carrying value of $2.3 million at the disposal date. 

As further discussed in Note 4, “Acquisitions,” during the fourth quarter of 2022, the Company recorded $4.0 million of separately 
identifiable  intangible  assets,  related  to  acquired  customer  relationships  and  trade  name,  as  part  of  the  acquisition  of  CSuite on 
November 1, 2022. The customer relationships intangible asset of $2.5 million is being amortized over seven years based on the pattern 
intangible 
in  which 
asset of $1.5 million is deemed 
this 
life and 
acquisition are provisional and subject to adjustment during the measurement period. The Company expects to complete its purchase 
price allocation in early 2023. The estimates, allocations and calculations recorded at December 31, 2022 are subject to change as we 

the  economic  benefits  of 
to  have 

the 
indefinite  useful 

intangible  asset  are  expected 

intangible  assets  related 

to  be  consumed.  The 

is not  amortized. The 

trade  name 

to 

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KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

obtain further information; therefore, the final fair values of the assets acquired and liabilities assumed may not agree with the estimates 
included in these consolidated financial statements. 

As further discussed in Note 4, “Acquisitions,” during the fourth quarter of 2022, the Company recorded $6.7 million of separately 
identifiable  intangible  assets,  related  to  acquired  customer  relationships  and  trade  name,  as  part  of  the  acquisition  of  SNS  on 
November 18, 2022. The customer relationships intangible asset of $3.6 million is being amortized over nine years based on the pattern 
intangible 
in  which 
asset of $3.1 million is deemed 
this 
life and 
acquisition are provisional and subject to adjustment during the measurement period. The Company expects to complete its purchase 
price allocation in early 2023. The estimates, allocations and calculations recorded at December 31, 2022 are subject to change as we 
obtain further information; therefore, the final fair values of the assets acquired and liabilities assumed may not agree with the estimates 
included in these consolidated financial statements. 

the  economic  benefits  of 
to  have 

the 
indefinite  useful 

intangible  asset  are  expected 

intangible  assets  related 

to  be  consumed.  The 

is not  amortized. The 

trade  name 

to 

As further discussed in Note 4, “Acquisitions,” during the fourth quarter of 2021, the Company recorded $6.5 million of separately 
identifiable  intangible  assets,  related  to  acquired  customer  relationships  and  trade  name,  as  part  of  the  acquisition  of  Ravix  on 
October 1, 2021. The customer relationships intangible asset of $4.0 million is being amortized over seven years based on the pattern in 
which  the  economic  benefits  of  the  intangible  asset  are  expected  to  be  consumed.  The  trade  name  intangible  asset of  $2.5 
million is deemed to have indefinite useful life and is not amortized.  

The  Company’s  other  intangible  assets  with  definite  useful  lives  are  amortized  either  based  on  the  patterns  in  which  the  economic 
benefits of the intangible assets are expected to be consumed or using the straight-line method over their estimated useful lives, which 
range from 7 to 15 years. Amortization of intangible assets was $6.1 million and $4.8 million for the years ended December 31, 2022 
and December 31, 2021, respectively. The estimated aggregate future amortization expense of all intangible assets is $5.6 million for 
2023, $4.3 million for 2024, $3.1 million for 2025, $2.2 million for 2026, $1.6 million for 2027 and $2.0 million thereafter. 

The trade names intangible assets have indefinite useful lives and are not amortized. All intangible assets with indefinite useful lives are 
reviewed annually by the Company for impairment. No impairment charges were taken on intangible assets in 2022 or 2021. 

NOTE 10 PROPERTY AND EQUIPMENT 

Property and equipment at December 31, 2022 and December 31, 2021 are comprised as follows: 

(in thousands) 

Leasehold improvements 
Furniture and equipment 
Computer hardware 
Total 

(in thousands) 

Leasehold improvements 
Furniture and equipment 
Computer hardware 
Total 

  $ 

  $ 

  $ 

  $ 

Total Property and Equipment 

December 31, 2022   

Cost 

     Accumulated 
     Depreciation 

     Carrying Value    
279   
56   
438   
773   

206     $ 
319       
516       
1,041     $ 

Total Property and Equipment 

December 31, 2021   

Cost 

     Accumulated 
     Depreciation 

     Carrying Value    
123   
120   
858   
1,101   

163     $ 
442       
1,630       
2,235     $ 

485     $ 
375       
954       
1,814     $ 

286     $ 
562       
2,488       
3,336     $ 

For the  years  ended  December  31,  2022  and  December  31,  2021,  depreciation  expense  on  property  and  equipment  of $0.3 million 
and $0.2 million, respectively, is included in general and administrative expenses in the consolidated statements of operations. 

75 

  
  
    
      
  
  
  
  
    
  
      
  
  
  
  
    
    
  
    
      
  
  
  
  
    
  
      
  
  
  
  
    
    
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

NOTE 11 DERIVATIVES 

(a) 

Interest rate swap: 

On April 1, 2021, the Company entered into an interest rate swap agreement with CIBC Bank USA to convert the variable London 
interbank offered interest rate for three-month U.S. dollar deposits (“LIBOR”) interest rate on a portion of its 2020 KWH Loan (as 
defined below in Note 12, “Debt”) to a fixed interest rate of 1.18%.  On September 15, 2022, the interest rate swap agreement was 
amended to convert from a variable Secured Overnight Financing Rate (“SOFR”) to a fixed interest rate of 1.103%.  The interest rate 
swap had an initial notional amount of $11.9 million and matures on February 29, 2024. 

The purpose of this interest rate swap, which is not designated as a cash flow hedge, is to reduce the Company’s exposure to variability 
in cash flows from interest payments attributable to fluctuations in the variable interest rate associated with the 2020 KWH Loan.  The 
Company has not elected hedge accounting for the interest rate swap.  The interest rate swap is recorded in the consolidated balance 
sheets at fair value with changes in fair value recorded in the consolidated statement of operations. 

The notional amount of the interest rate swap contract is $8.6 million at December 31, 2022.  At December 31, 2022 and December 31, 
2021, the fair value of the interest rate swap contract was an asset of $0.3 million and a liability of less than $0.1 million, respectively, 
which is included in other receivables and accrued expenses and other liabilities, respectively, in the consolidated balance sheets.  During 
the years ended December 31, 2022 and December 31, 2021, the Company recognized a gain of $0.3 million and a loss of less than $0.1 
million, respectively, related to the change in fair value of the interest rate swap, which is included in interest expense in the consolidated 
statements of operations and within cash flows (used in) provided by operating activities from continuing operations in the consolidated 
statements of cash flows.  Net cash receipts of $0.1 million were made to the Company during the year ended December 31, 2022 and 
net cash payments of less than $0.1 million were made by the Company during the year ended December 31, 2021, to settle a portion of 
the liabilities related to the interest rate swap agreement.  These cash receipts and payments are reflected as cash inflows or outflows in 
the consolidated statements of cash flows within net cash (used in) provided by operating activities from continuing operations. 

(b) 

Trust preferred debt repurchase options: 

On August 2, 2022, the Company entered into an agreement with a holder of four of the trust preferred debt instruments (“TruPs”) that 
gives the Company the option to repurchase up to 100% of the holder’s principal and deferred interest for a purchase price equal to 
63.75% of the outstanding principal and deferred interest (“August Option”). Originally, the agreement called for a repurchase at 63%, 
which escalated to 63.75% once the September 26, 2022 agreement (described below) was signed.  The Company has agreed that any 
repurchase made will be for no less than 50% of the TruPs held by the holder.   

Until the earlier of (i) the date that all four of the preferred debt instruments have been repurchased and (ii) the nine month anniversary 
of the agreement (“May Termination Date”), all interest on the four preferred debt instruments will continue to accrue.  However, with 
respect to TruPs that are repurchased prior to the May Termination Date, the amount of interest accrued during the term of the agreement 
will be treated as an offset and reduce the repurchase price for such TruPs.  The Company will have no obligation to pay any such 
accrued interest with respect to any of the TruPs that are repurchased prior to the May Termination Date. 

The Company paid approximately $2.0 million to the holder for this option and the Company has until the May Termination Date to 
execute the repurchases.  If the Company repurchases less than $30.0 million of principal and deferred interest, or fails to purchase any 
principal or deferred interest within one year, then the $2.0 million paid is forfeited.  If the Company repurchases an amount equal to or 
greater than $30.0 million, then the $2.0 million paid would be applied to such repurchases. 

On September 20, 2022, the Company entered into an additional agreement with the same party to the August 2, 2022 agreement that 
gives the Company the option to repurchase up to 100% of the holder’s principal and deferred interest for 63.75% of the outstanding 
principal and deferred interest relating to a portion of a fifth TruPs held (“September 20 Option”). The September 20, 2022 agreement 
is subject to the same terms and conditions as the August 2, 2022 and no additional consideration was paid. 

On September 26, 2022, the Company entered into an agreement with a holder of a portion of one of the TruPs that gives the Company 
the option to repurchase up to 100% of the holder’s principal and deferred interest for a purchase price equal to 63% of the outstanding 
principal and deferred interest (“September 26 Option”).  

Until the earlier of (i) the date that all of the preferred debt instrument has been repurchased and (ii) the May Termination Date, all 
interest on the preferred debt instrument will continue to accrue.  However, with respect to TruPs that are repurchased prior to the May 
Termination Date, the amount of interest accrued during the term of the agreement will be treated as an offset and reduce the repurchase 
price  for  such  TruPs.   The  Company  will  have  no  obligation  to  pay  any  such  accrued  interest  with  respect  to  the  TruPs that  are 
repurchased prior to the May Termination Date. 

76 

  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

The Company paid approximately $0.3 million to the holder for this option and the Company has until the May Termination Date to 
execute the repurchase.  If the Company fails to purchase any principal or deferred interest by the May Termination Date, then the $0.3 
million paid is forfeited.  If the Company repurchases any of the TruPs, then the $0.3 million paid would be applied to any repurchases. 

The August Option, September 20 Option and September 26 Options (collectively “the TruPs Options”) are derivative contracts. The 
Company’s accounting policies do not apply hedge accounting treatment to derivative instruments.  The TruPs options are recorded in 
the consolidated balance sheets at fair value with changes in fair value recorded in the consolidated statements of operations. 

The notional amount of the TruPs Options contracts is $59.7 million at December 31, 2022.  At December 31, 2022, the fair value of the 
TruPs Options contracts was an asset of $19.0 million, which is included in other assets in the consolidated balance sheet. See Note 23, 
“Fair Value of Financial Instruments,” for further discussion. During the year ended December 31, 2022, the Company recognized an 
initial gain of $11.4 million, equal to the difference between the fair value of the TruPs Options contracts at the date of inception and the 
cash consideration paid, and a subsequent gain on change in fair value of $5.3 million, both of which are included in gain on change in 
fair value of derivative asset option contracts in the consolidated statement of operations and as an adjustment to calculate cash flows used 
in operating activities from continuing operations in the consolidated statement of cash flows.  No cash payments were made to repurchase 
any of the TruPs during the year ended December 31, 2022 with respect to the TruPs Options contracts. 

NOTE 12 DEBT 

Debt consists of the following instruments at December 31, 2022 and December 31, 2021: 

(in thousands) 

Bank loans: 

2021 Ravix Loan 
2022 Ravix Loan 
SNS Loan 
2020 KWH Loan 
Total bank loans 

Notes payable: 
Flower Note 
Total notes payable 

Subordinated debt 
Total 

December 31, 2022 
Carrying 
Value 

     Fair Value       Principal 

December 31, 2021 
Carrying 
Value 

     Fair Value    

   Principal 

  $ 

5,300     $ 
5,950       
6,850       
16,708       
34,808       

5,300     $ 
5,754       
6,755       
16,472       
34,281       

5,460     $ 
6,245       
6,921       
16,819       
35,445       

6,000     $ 
—       
—       
21,186       
27,186       

—       
—       
90,500       
125,308     $ 

—       
—       
67,811       
102,092     $ 

—       
—       
67,811       
103,256     $ 

6,411       
6,411       
90,500       
124,097     $ 

  $ 

5,847     $ 
—       
—       
20,870       
26,717       

6,411       
6,411       
60,973       
94,101     $ 

5,936   
—   
—   
20,815   
26,751   

7,101   
7,101   
60,973   
94,825   

Subordinated debt mentioned above consists of the following trust preferred debt instruments: 

Issuer 
Kingsway CT Statutory 
Trust I 
Kingsway CT Statutory 
Trust II 
Kingsway CT Statutory 
Trust III 
Kingsway DE Statutory 
Trust III 
Kingsway DE Statutory 
Trust IV 
Kingsway DE Statutory 
Trust VI 

Principal 
   (in thousands)   

Issue date 

  $ 

  $ 

  $ 

  $ 

  $ 

  $ 

15,000   

12/4/2002 

17,500   

5/15/2003 

20,000    10/29/2003 

15,000   

5/22/2003 

10,000   

9/30/2003 

13,000    12/16/2003 

Interest 
annual interest rate equal to LIBOR, plus 4.00% 
payable quarterly 
annual interest rate equal to LIBOR, plus 4.10% 
payable quarterly 
annual interest rate equal to LIBOR, plus 3.95% 
payable quarterly 
annual interest rate equal to LIBOR, plus 4.20% 
payable quarterly 
annual interest rate equal to LIBOR, plus 3.85% 
payable quarterly 
annual interest rate equal to LIBOR, plus 4.00% 
payable quarterly 

Redemption date 

12/4/2032 

5/15/2033 

10/29/2033 

5/22/2033 

9/30/2033 

1/8/2034 

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KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

(a) 

Bank loans: 

Ravix 

As part of the acquisition of Ravix on October 1, 2021, Ravix became a wholly owned subsidiary of Ravix Acquisition LLC (“Ravix 
LLC”), and together they borrowed from a bank a principal amount of $6.0 million in the form of a term loan, and established a $1.0 
million revolver to finance the acquisition of Ravix (together, the “2021 Ravix Loan”).  The 2021 Ravix Loan requires monthly payments 
of principal and interest.  The 2021 Ravix Loan has an annual interest rate equal to the greater of the Prime Rate plus 0.5%, or 3.75%.  At 
December 31, 2022, the interest rate was 8.00%. The term loan matures on October 1, 2027 and the revolver was scheduled to mature on 
October  1,  2023  (see  discussion  below  related  to  the  2022  Ravix  Loan).  Subsequent  to  October  1,  2021,  Ravix borrowed  and  made 
payments under the revolver.  The carrying values at December 31, 2022 and December 31, 2021 for the 2021 Ravix Loan includes $5.1 
million  and $5.7 million,  respectively,  related  to  the  term  loan  and  zero  and  $0.1 million  related  to  the  revolver.  The  Company  also 
recorded as a discount to the carrying value of the 2021 Ravix Loan issuance costs of $0.2 million specifically related to the 2021 Ravix 
Loan.  The 2021 Ravix Loan is carried in the consolidated balance sheet at December 31, 2022 at its unpaid principal balance.  

Subsequent to the acquisition of CSuite on November 1, 2022, CSuite became a wholly owned subsidiary of Ravix LLC.  As a result of 
the acquisition of CSuite, on November 16, 2022, the 2021 Ravix Loan was amended to (1) include CSuite as a borrower; (2) borrow 
an additional principal amount of $6.0 million in the form of a supplemental term loan (the “2022 Ravix Loan”); and (3) amend the 
maturity date and interest rate of the $1.0 million revolver (the “2022 Revolver”).  The 2022 Ravix Loan requires monthly payments of 
principal and interest.  The 2022 Ravix Loan matures on November 16, 2028 and has an annual interest rate equal to the Prime Rate plus 
0.75%.  At December 31, 2022, the interest rate was 8.25%.  The 2022 Revolver matures on November 16, 2024 and has an annual 
interest rate equal to the Prime Rate plus 0.50%. At December 31, 2022, the balance of the 2022 Revolver was zero.  

The Company also recorded as a discount to the carrying value of the 2022 Ravix Loan issuance costs of $0.1 million specifically related 
to the 2022 Ravix Loan.  The 2022 Ravix Loan is carried in the consolidated balance sheet at December 31, 2022 at its amortized cost, 
which reflects the monthly pay-down of principal as well as the amortization of the debt discount and issuance costs using the effective 
interest rate method. 

The 2022  Ravix  Loan  and  the  2021 Ravix  Loan  were  not  deemed  to  be  substantially  different; therefore,  the  2022  Ravix  Loan  is 
accounted for as a modification of the 2021 Ravix Loan and a new effective interest rate was determined based on the carrying amount 
of the 2021 Ravix Loan.  The issuance costs related to the 2022 Ravix Loan, along with the existing unamortized issuance costs from 
the 2021 Ravix Loan, are being amortized over the remaining term of the 2022 Ravix Loan using the effective interest rate.   

The fair values of the 2021 Ravix Loan and the 2022 Ravix Loan disclosed in the table above is derived from quoted market prices of 
B and BB minus rated industrial bonds with similar maturities and is categorized within Level 2 of the fair value hierarchy. The 2021 
Ravix Loan and the 2022 Ravix Loan are secured by certain of the equity interests and assets of Ravix and CSuite. 

The 2021 Ravix Loan and the 2022 Ravix Loan contains a number of covenants, including, but not limited to, a leverage ratio and a 
fixed charge ratio, all of which are as defined in and calculated pursuant to the 2021 Ravix Loan and 2022 Ravix Loan that, among other 
things, restrict Ravix and CSuite’s ability to incur additional indebtedness, create liens, make dividends and distributions, engage in 
mergers, acquisitions and consolidations, make certain payments and investments and dispose of certain assets. 

SNS 

As part of the asset acquisition of SNS on November 18, 2022, the Company formed Secure Nursing Service LLC, who became a wholly 
owned subsidiary of Pegasus Acquirer Holdings LLC (“Pegasus LLC”), and together they borrowed from a bank a principal amount of 
$6.5 million in the form of a term loan, and established a $1.0 million revolver to finance the acquisition of SNS (together, the “SNS 
Loan”).  The SNS Loan has an annual interest rate equal to the greater of the Prime Rate plus 0.5%, or 5.00%.  At December 31, 2022, 
the  interest rate  was 8.00%.  Monthly principal  payments on  the  term  loan begin on November 15, 2023.  The revolver  matures  on 
November 18, 2023 and the term loan matures on November 18, 2028.  Subsequent to November 18, 2022, SNS borrowed under the 
revolver.   The  carrying  value at  December  31,  2022 for  the  SNS  Loan  includes $6.4 million  related  to  the  term  loan 
and $0.4 million related to the revolver. 

The Company also recorded as a discount to the carrying value of the SNS Loan issuance costs of $0.1 million specifically related to 
the SNS Loan.  The SNS Loan is carried in the consolidated balance sheet at its amortized cost, which reflects the amortization of the 
debt discount and issuance costs using the effective interest rate method.  The fair value of the SNS Loan disclosed in the table above is 
derived from quoted market prices of B and BB minus rated industrial bonds with similar maturities and is categorized within Level 2 
of the fair value hierarchy. The SNS Loan is secured by certain of the equity interests and assets of SNS. 

78 

  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

The SNS Loan contains a number of covenants, including, but not limited to, a leverage ratio and a fixed charge ratio and limits on 
annual capital expenditures, all of which are as defined in and calculated pursuant to the SNS Loan that, among other things, restrict 
SNS’s  ability  to  incur  additional  indebtedness,  create  liens,  make  dividends  and  distributions,  engage  in  mergers,  acquisitions  and 
consolidations, make certain payments and investments and dispose of certain assets. 

KWH 

In 2019, the Company formed Kingsway Warranty Holdings LLC (“KWH”), whose original subsidiaries included IWS Acquisition 
Corporation (“IWS”), Geminus Holdings Company, Inc. (“Geminus”) and Trinity Warranty Solutions LLC (“Trinity”). As part of the 
acquisition of PWI on December 1, 2020, PWI became a wholly owned subsidiary of KWH, which borrowed a principal amount of 
$25.7 million from a bank, consisting of a $24.7 million term loan and a $1.0 million revolving credit facility (the “2020 KWH Loan”). 
The proceeds from the 2020 KWH Loan were used to partially fund the acquisition of PWI and to fully repay the prior outstanding loan 
at KWH, which occurred on December 1, 2020. 

The 2020 KWH Loan had an annual interest rate equal to LIBOR having a floor of 0.75%, plus 2.75%.  During the second quarter of 
2022,  the  2020  KWH  Loan  was  amended  to  change  the  annual  interest  rate  to  be  equal  to  the  Secured  Overnight  Financing  Rate 
(“SOFR”), having a floor of 0.75%, plus spreads ranging from 2.62% to 3.12%.  At December 31, 2022, the interest rate was 6.96%. 
The  2020  KWH  Loan  matures  on  December  1,  2025.   The  carrying  values  at  December  31,  2022 and December  31, 
loan  and $0.5 million  and $0.5 million, 
2021 include $16.0 million  and $20.4 million, 
respectively, related to the revolver. 

respectively, 

related 

term 

the 

to 

The Company also recorded as a discount to the carrying value of the 2020 KWH Loan issuance costs of $0.4 million specifically related 
to the 2020 KWH Loan. The 2020 KWH Loan is carried in the consolidated balance sheets at its amortized cost, which reflects the 
quarterly pay-down of principal  as  well  as the  amortization of the  debt discount  and  issuance  costs using  the  effective  interest  rate 
method.   The fair value of the 2020 KWH Loan disclosed in the table above is derived from quoted market prices of B and BB minus 
rated industrial bonds with similar maturities and is categorized within Level 2 of the fair value hierarchy. The 2020 KWH Loan is 
secured by certain of the equity interests and assets of KWH and its subsidiaries. 

The 2020 KWH Loan contains a number of covenants, including, but not limited to, a leverage ratio, a fixed charge ratio and limits on 
annual capital expenditures, all of which are as defined in and calculated pursuant to the 2020 KWH Loan that, among other things, 
restrict KWH’s ability to incur additional indebtedness, create liens, make dividends and distributions, engage in mergers, acquisitions 
and consolidations, make certain payments and investments and dispose of certain assets. 

(b) 

Notes payable: 

Flower 

On January 5, 2015, Flower assumed a $9.2 million mortgage in conjunction with the purchase of investment real estate properties, 
which  is  recorded  as  note  payable  in  the  consolidated  balance  sheet  at  December  31,  2021  (“the  Flower  Note”).  The  Flower  Note 
required monthly payments of principal and interest and was secured by certain investments of Flower. The Flower Note was scheduled 
to mature on December 10, 2031 and had a fixed interest rate of 4.81%. On September 29, 2022, Flower sold its investment real estate 
properties and used a portion of the sales proceeds to repay the unpaid principal balance of the Flower Note.  The carrying value of the 
Flower Note of $6.4 million at December 31, 2021 represents its unpaid principal balance. The fair value of the Flower Note disclosed 
in the table above is derived from quoted market prices of A and BBB rated industrial bonds with similar maturities and is categorized 
within Level 2 of the fair value hierarchy. 

Paycheck Protection Program 

In April 2020, certain subsidiaries of the Company received loan proceeds under the Paycheck Protection Program (“PPP”), totaling 
$2.9 million with a stated annual interest rate of 1.00%. The PPP, established as part of the Coronavirus Aid, Relief, and Economic 
Security Act and administered by the U.S. Small Business Administration (the “SBA”), provides for loans to qualifying businesses for 
amounts up to 2.5 times of the average monthly payroll costs (as defined for purposes of the PPP) of the qualifying business. The loans 
and accrued interest are forgivable as long as the borrower uses the loan proceeds for eligible purposes, including payroll, costs, rent 
and  utilities,  during  the  twenty-four  week  period  following  the  borrower’s  receipt  of  the  loan  and  maintains  its  payroll  levels  and 
employee headcount. The amount of loan forgiveness will be reduced if the borrower reduces its employee headcount below its average 
employee headcount during a benchmark period or significantly reduces salaries for certain employees during the covered period. 

79 

  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

The Company used the entire loan amount for qualifying expenses. The U.S. Department of the Treasury has announced that it will 
conduct audits for PPP loans that exceed $2.0 million. If the Company were to be audited and receive an adverse outcome in such an 
audit, it could be required to return the full amount of the PPP Loan and may potentially be subject to civil and criminal fines and penalties. 

On December 21, 2020 the SBA approved the forgiveness of the full amount of one of the five PPP loans. The forgiveness included 
principal and interest of $0.4 million.  In January 2021 and March 2021, the SBA provided the Company with notices of forgiveness of 
the  full  amount  of  the  remaining  four  loans.  The  forgiveness  in  the  first  quarter  of  2021  included  total  principal  and  interest  of 
$2.5 million.  The loan forgiveness is included in gain on extinguishment of debt in the consolidated statement of operations for the 
years ended December 31, 2021.  

(c) 

Subordinated debt: 

Between  December  4,  2002  and  December  16,  2003,  six  subsidiary  trusts  of  the  Company  issued  $90.5  million  of  30-year  capital 
securities to third-parties in separate private transactions. In each instance, a corresponding floating rate junior subordinated deferrable 
interest debenture was then issued by KAI to the trust in exchange for the proceeds from the private sale. The floating rate debentures 
bear interest at the rate of LIBOR, plus spreads ranging from 3.85% to 4.20%. The Company has the right to call each of these securities 
at par value any time after five years from their issuance until their maturity. 

The subordinated debt is carried in the consolidated balance sheets at fair value. See Note 23, “Fair Value of Financial Instruments,” for 
further discussion of the subordinated debt. The portion of the change in fair value of subordinated debt related to the instrument-specific 
credit risk is recognized in other comprehensive loss. Of the $6.8 million increase in fair value of the Company’s subordinated debt 
between December 31, 2021 and December 31, 2022, $1.9 million is reported as increase in fair value of debt attributable to instrument-
specific credit risk in the Company’s consolidated statements of comprehensive income (loss) and $4.9 million is reported as loss on 
change in fair value of debt in the Company’s consolidated statements of operations. Of the $10.0 million increase in fair value of the 
Company’s subordinated debt between December 31, 2020 and December 31, 2021, $6.8 million is reported as increase in fair value of 
debt  attributable  to  instrument-specific  credit  risk  in  the  Company’s  consolidated  statements  of  comprehensive  income  (loss) 
and $3.2 million is reported as loss on change in fair value of debt in the Company’s consolidated statements of operations. 

During the third quarter of 2018, the Company gave notice to its Trust Preferred trustees of its intention to exercise its voluntary right 
to defer interest payments for up to 20 quarters, pursuant to the contractual terms of its outstanding Trust Preferred indentures, which 
permit interest deferral. This action does not constitute a default under the Company’s Trust Preferred indentures or any of its other debt 
indentures. At December 31, 2022 and December 31, 2021, deferred interest payable of $25.5 million and $18.7 million, respectively, 
is included in accrued expenses and other liabilities in the consolidated balance sheets. 

The agreements governing the subordinated debt contain a number of covenants that, among other things, restrict the Company’s ability 
to  incur  additional  indebtedness,  make  dividends  and  distributions,  and  make  certain  payments  in  respect  of  the  Company’s 
outstanding securities. 

NOTE 13 LEASES 

The Company has operating leases for office space that include fixed base rent payments, as well as variable rent payments to reimburse 
the landlord for operating expenses and taxes. The Company’s variable lease payments do not depend on a published index or rate, and 
therefore, are expensed as incurred. The Company includes only fixed payments for lease components in the measurement of the right-
of-use asset and lease liability. There are no residual value guarantees. 

Operating lease costs and variable lease costs included in general and administrative expenses for the year ended December 31, 2022 
were $0.8 million and $0.2 million, respectively.  Operating lease costs and variable lease costs included in general and administrative 
expenses for the year ended December 31, 2021 were $1.0 million and $0.1 million, respectively. 

80 

  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

The annual maturities of lease liabilities as of December 31, 2022 were as follows: 

(in thousands) 
2023 
2024 
2025 
2026 
2027 
2028 and thereafter 
Total undiscounted lease payments 
Imputed interest 
Total lease liabilities 

Lease 
Commitments    
438   
405   
231   
167   
107   
17   
1,365   
148   
1,217   

  $ 

  $ 

Lease  liabilities  are included  in  accrued  expenses  and  other  liabilities  in  the  consolidated  balance  sheets.   The  weighted-average 
remaining lease term for operating leases was 3.57 years as of December 31, 2022. The weighted average discount rate of operating 
leases was 5.84% as of December 31, 2022. Cash paid for amounts included in the measurement of lease liabilities was $0.8 million 
and $1.0 million for the years ended December 31, 2022 and December 31, 2021, respectively. 

Supplemental non-cash information related to leases for the year ended December 31, 2022 includes right-of-use assets of $0.3 million 
acquired in exchange for $0.5 million of lease obligations. 

NOTE 14 REVENUE FROM CONTRACTS WITH CUSTOMERS 

Revenue  from  contracts  with  customers  relates  to  the  Extended  Warranty  and  Kingsway  Search  Xcelerator segments  and 
includes: vehicle  service  agreement  fees,  GAP  commissions,  maintenance  support  service  fees,  warranty  product  commissions, 
homebuilder warranty service fees, homebuilder warranty commissions and business services consulting revenue.  Revenue is based on 
terms of various agreements with credit unions, consumers, businesses and homebuilders. Customers either pay in full at the inception 
of a warranty contract, commission product sale, or when consulting services are billed, or on terms subject to the Company’s customary 
credit reviews. 

The following table disaggregates revenues from contracts with customers by revenue type: 

(in thousands) 

Vehicle service agreement fees and GAP commissions 
Maintenance support service fees 
Warranty product commissions 
Homebuilder warranty service fees 
Homebuilder warranty commissions 
Business services consulting fees 
Service fee and commission revenue 

IWS, Geminus and PWI 
Trinity 
Trinity 
PWSC (a) 
PWSC (a) 
Ravix, CSuite and SNS 

  $ 

  $ 

   (a) Through the July 29, 2022 disposal 

Years ended December 31,   
2021   

2022     

58,775     $ 
5,815       
4,564       
4,348       
540       
19,238       
93,280     $ 

57,756   
4,871   
4,317   
7,099   
876   
3,482   
78,401   

During the first quarter of 2022, IWS recorded a net charge of $0.9 million relating to a change in estimate in accounting for deferred 
revenue and deferred contract costs associated with vehicle service agreement fees, resulting in an increase to deferred service fees of 
$1.1 million and an increase in deferred contract costs of $0.2 million. 

Receivables  from  contracts  with  customers  are  reported  as  service  fee  receivable,  net  in  the  consolidated  balance  sheets  and  at 
December 31,  2022  and  December  31,  2021 were  $10.3  million  and $6.7  million, respectively. The  increase  in  receivables  from 
contracts with customers is primarily due to receivables related to CSuite and SNS, which were acquired on November 1, 2022 and 
November  18,  2022,  respectively,  and  the timing  difference  between  the  Company’s  satisfaction  of  performance  obligations  and 
customer payments; partially offset by a decrease due to the disposal of PWSC on July 29, 2022.   

81 

  
  
    
    
    
    
    
    
    
  
  
  
  
  
  
  
  
  
  
      
        
  
    
    
    
    
    
    
 
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

The Company records deferred service fees resulting from contracts with customers when payment is received in advance of satisfying 
the performance obligations.  Changes in deferred service fees for the years ended December 31, 2022 and December 31, 2021 were 
as follows: 

(in thousands) 
Balance, December 31, 2020 
Deferral of revenue 
Recognition of deferred service fees 
Balance, December 31, 2021 
Deferral of revenue 
Recognition of deferred service fees 
Deferred service fees disposed of related to PWSC 
Balance, December 31, 2022 

Years ended 
December 31,    
87,945   
60,415   
(59,143 ) 
89,217   
61,058   
(59,966 ) 
(7,596 ) 
82,713   

  $ 

  $ 

The decrease in deferred service fees during the year ended December 31, 2022 is primarily due to the disposal of PWSC on July 29, 
2022,  partially  offset  by additions  to  deferred  service  fees  in  excess  of  deferred  service  fees  recognized  during  the year ended 
December 31, 2022 as cash sales have begun to increase.  The increase in deferred service fees during the year ended December 31, 
2021 is primarily due to additions to deferred service fees in excess of deferred service fees recognized during the year ended December 
31, 2021, that was partially offset by the adjustment recorded in the third quarter of 2021 of $3.6 million to reduce PWI’s acquisition 
date deferred revenue to fair value.   

The Company expects to recognize within one year as service fee and commission revenue approximately 52.7% of the deferred service 
fees as of December 31, 2022. Approximately $43.2 million and $44.2 million of service fee and commission revenue recognized during 
the  years  ended  December  31,  2022  and  December  31,  2021  was  included  in  deferred  service  fees  as  of  December  31,  2021  and 
December 31, 2020, respectively. 

Deferred contract costs 

Deferred contract costs represent the deferral of incremental costs to obtain or fulfill a contract with a customer.  The deferred contract 
costs  balances  and  related  amortization  expense  for  the years  ended December  31,  2022  and  December  31,  2021  are  comprised 
as follows: 

(in thousands) 

Years ended December 31, 2022     

Years ended December 31, 2021   

Costs to 
Obtain a 
Contract 

Costs to 
Fulfill a 
Contract 

Costs to 
Obtain a 
Contract 

Costs to 
Fulfill a 
Contract 

Total 

Balance at January 1, net 
Additions 
Amortization 
Balance at December 31, net 

  $ 

  $ 

10,850     $ 
9,273       
(6,949 )     
13,174     $ 

80     $ 
21       
(18 )     
83     $ 

10,930     $ 
9,294       
(6,967 )     
13,257     $ 

8,759     $ 
8,674       
(6,583 )     
10,850     $ 

76     $ 
27       
(23 )     
80     $ 

Total 

8,835   
8,701   
(6,606 ) 
10,930   

No impairment charges related to deferred contract costs were recorded in 2022 or 2021.  

NOTE 15 INCOME TAXES 

The Company and all of its eligible U.S. subsidiaries file a U.S. consolidated federal income tax return (“KFSI Tax Group”). The method 
of allocating federal income taxes among the companies in the KFSI Tax Group is subject to written agreement, approved by each 
company’s Board of Directors. The allocation is made primarily on a separate return basis, with current credit for any net operating 
losses or other items utilized in the consolidated federal income tax return. The Company’s non-U.S. subsidiaries file separate foreign 
income tax returns.    

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KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

Income tax expense (benefit) consists of the following: 

(in thousands) 

Current income tax expense 
Deferred income tax expense (benefit) 
Income tax expense (benefit) 

Years ended December 31,   
2021   

2022     

  $ 

  $ 

3,419     $ 
1,406       
4,825     $ 

395   
(4,311 ) 
(3,916 ) 

Income tax expense (benefit) varies from the amount that would result by applying the applicable U.S. corporate income tax rate of 21% 
to income (loss) from continuing operations before income tax expense (benefit). The following table summarizes the differences: 

(in thousands) 

Income tax expense (benefit) at U.S. statutory income tax rate 
Valuation allowance 
Indefinite life intangibles 
Non-deductible compensation 
Investment income 
State income tax 
Disposition of subsidiary 
Non-taxable income 
Other 
Income tax expense (benefit) for continuing operations 

Years ended December 31,   
2021   
(1,393 ) 
(3,103 ) 
215   
649   
(253 ) 
338   
—   
(524 ) 
155   
(3,916 ) 

2022     
7,341     $ 
(10,100 )     
106       
867       
(62 )     
3,052       
3,268       
—       
353       
4,825     $ 

  $ 

  $ 

The tax effects of temporary differences that give rise to significant portions of the deferred income tax assets and liabilities are presented 
as follows: 

(in thousands) 

Deferred income tax assets: 
Losses carried forward 
Unpaid loss and loss adjustment expenses and unearned premiums 
Intangible assets 
Debt issuance costs 
Investments 
Deferred rent 
Deferred revenue 
Compensation 
Other 
Valuation allowance 
Deferred income tax assets 
Deferred income tax liabilities: 
Indefinite life intangibles 
Depreciation and amortization 
Fair value of debt 
Land 
Intangible assets 
Deferred revenue 
Investments 
Deferred acquisition costs 
Other 

Deferred income tax liabilities 
Net deferred income tax liabilities 

83 

2022     

December 31,   
2021   

  $ 

  $ 

  $ 

  $ 
  $ 

137,155     $ 
3,902       
1,380       
474       
2,065       
64       
147       
306       
155       
(130,596 )     
15,052     $ 

(3,815 )   $ 
(756 )     
(7,598 )     
(47 )     
(2,606 )     
(1,188 )     
—       
(2,784 )     
(434 )     
(19,228 )   $ 
(4,176 )   $ 

181,096   
3,864   
1,050   
789   
1,198   
586   
1,603   
520   
131   
(169,678 ) 
21,159   

(19,179 ) 
(14,485 ) 
(4,048 ) 
(4,482 ) 
(3,698 ) 
(1,443 ) 
(35 ) 
(2,295 ) 
(47 ) 
(49,712 ) 
(28,553 ) 

  
  
  
  
      
        
  
    
  
  
  
  
    
    
    
    
    
    
    
    
  
  
  
  
      
        
  
    
    
    
    
    
    
    
    
    
      
        
  
    
    
    
    
    
    
    
    
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

The  Company  maintains  a  valuation  allowance  for  its  gross  deferred  income  tax  assets  of  $130.6  million  (U.S.  operations  - 
$130.6 million; Other - less than $0.1 million) and $169.7 million (U.S. operations - $169.7 million; Other - less than $0.1 million) at 
December 31, 2022 and December 31, 2021, respectively. The Company’s businesses have generated substantial operating losses in 
prior years. These losses can be available to reduce income taxes that might otherwise be incurred on future taxable income; however, 
it is uncertain whether the Company will generate the taxable income necessary to utilize these losses or other reversing temporary 
differences. This uncertainty has caused management to place a full valuation allowance on its December 31, 2022 and December 31, 
2021 net deferred income tax assets, excluding the deferred income tax asset and liability amounts set forth in the paragraph below. 

In 2022, the Company (i) increased by $2.1 million its valuation allowance associated with business interest expense carryforwards with 
an indefinite life; and (ii) increased by $0.1 million its valuation allowance relating to a change in indefinite life deferred income tax 
liabilities. 

In  2021,  the  Company  (i)  released  into  income  $2.0  million  of  its  valuation  allowance  associated  with  business  interest  expense 
carryforwards with an indefinite life and (ii) released into income $3.3 million and $0.8 million of its valuation allowance, as a result of 
its acquisitions of PWI and Ravix, respectively, due to net deferred income tax liabilities that are expected to reverse during the period 
in which the Company will have deferred income tax assets available. 

The Company carries net deferred income tax liabilities of $4.2 million and $28.6 million at December 31, 2022 and December 31, 
2021, respectively, that consists of: 

•  Zero and $8.2 million of deferred income tax liabilities that are scheduled to reverse in periods after the expiration of the KFSI 

Tax Group’s consolidated U.S. net operating loss carryforwards; 

• 

$3.8 million and $23.8 million of deferred income tax liabilities related to land and indefinite life intangible assets; 

•  Zero  and  $3.3  million  of  deferred  income  tax  assets  associated  with  business  interest  expense  carryforwards  with  an 

indefinite life; 

•  Zero and $0.5 million of deferred state income tax assets; and 

• 

$0.4 million and $0.4 of deferred state income tax liabilities. 

The Tax Cuts and Jobs Act (the “Tax Act”) modified the U.S. net operating loss deduction, effective with respect to losses arising in tax 
years beginning after December 31, 2017. The Tax Act, however, did not limit the utilization, in 2018 and later tax years, of U.S. net 
operating losses generated in 2017 and prior tax years. 

Amounts,  originating  dates  and  expiration  dates  of  the  KFSI  Tax  Group’s  consolidated  U.S.  net  operating  loss  carryforwards, 
totaling $644.2 million, are as follows: 

Year of net operating loss 

Expiration date 

2009 
2010 
2011 
2012 
2013 
2014 
2016 
2017 

$ 

2029 
2030 
2031 
2032 
2033 
2034 
2036 
2037 

Net operating loss   
(in thousands)   

406,477   
92,058   
39,865   
30,884   
30,779   
7,245   
16,006   
20,848   

In addition, not reflected in the table above, are net operating loss carryforwards of (i) $8.9 million relating to losses generated in separate 
U.S. tax return years, which losses will expire over various years through 2037 and (ii) $0.1 million relating to non-U.S. operations, 
which losses will expire over various years through 2042. 

84 

  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
    
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

A reconciliation of the beginning and ending unrecognized tax benefits related to discontinued operations, exclusive of interest and 
penalties, is as follows: 

(in thousands) 

Unrecognized tax benefits - beginning of year 

Gross additions 
Gross reductions 
Impact due to expiration of statute of limitations 

Unrecognized tax benefits - end of year 

2022     

65     $ 
—       
(65 )     
—       
—     $ 

December 31,   
2021   
1,381   
—   
—   
(1,316 ) 
65   

  $ 

  $ 

The  amount  of  unrecognized  tax  benefits  that,  if  recognized  as  of  December  31,  2022  and  December  31,  2021  would  affect  the 
Company’s effective tax rate on discontinued operations, was a benefit of $0.1 million and $2.8 million, respectively. 

During the year ended December 31, 2022, the Company recorded an income tax benefit of $0.2 million for the release of a liability for 
unrecognized tax benefits (including interest and penalties) that had been included in income taxes payable in the consolidated balance 
sheets.   The  Company  carried  a  liability  for  unrecognized  tax  benefits  of  zero  and  $0.1  million  as  of  December  31,  2022  and 
December 31, 2021, respectively, that is included in income taxes payable in the consolidated balance sheets. The Company classifies 
interest  and  penalty  accruals,  if  any,  related  to  unrecognized  tax  benefits  as  income  tax  expense  (benefit).  During  the  years  ended 
December  31,  2022  and  December  31,  2021,  the  Company  recognized  a  benefit  of  $0.1  million  and $1.5  million,  respectively, for 
interest  and  penalties,  which  are  included  in  (loss)  income  from  discontinued  operations,  net  of  taxes.  At  December  31,  2022  and 
December 31, 2021, the Company carried an accrual for the payment of interest and penalties of zero and $0.1 million, respectively, 
that is included in income taxes payable in the consolidated balance sheets. 

The federal income tax returns of the Company’s U.S. operations for the years through 2018 are closed for Internal Revenue Service 
(“IRS”) examination. The Company’s federal income tax returns are not currently under examination by the IRS for any open tax years. 
The federal income tax returns of the Company’s Canadian operations for the years through 2017 are closed for Canada Revenue Agency 
(“CRA”) examination. The Company’s Canadian federal income tax returns are not currently under examination by the CRA for any 
open tax years. 

NOTE 16 EARNINGS (LOSS) PER SHARE 

The following table sets forth the reconciliation of numerators and denominators for the basic and diluted earnings (loss) per share 
computation for the years ended December 31, 2022 and December 31, 2021: 

(in thousands, except per share data) 

Numerator: 

Income (loss) from continuing operations 
Plus (less): net loss (income) from continuing operations attributable to noncontrolling 
interests 
Less: dividends on preferred stock, net of tax 

Numerator used in calculating basic earnings (loss) per share from continuing operations 

attributable to common shareholders 
Adjustment to add-back dividends on preferred stock 
Adjustment for proportionate interest in Ravix and SNS’s earnings attributable to 
common stock 

  $ 

Numerator used in calculating diluted earnings (loss) per share from continuing operations 
attributable to common shareholders 

  $ 

Loss (income) from discontinued operations 
Plus (less): net loss (income) from discontinued operations attributable to 
noncontrolling interests 

Numerator used in calculating diluted earnings (loss) per share - net income (loss) attributable 
to common shareholders 

  $ 

85 

Years ended December 31,   
2021   

2022     

  $ 

30,132     $ 

(2,714 ) 

1,471       
(306 )     

31,297     $ 
306       

(1,660 ) 
(494 ) 

(4,868 ) 
—   

76       

—   

31,679     $ 
(15,067 )     

8,186       

24,798     $ 

(4,868 ) 
4,574   

(542 ) 

(836 ) 

  
  
  
  
    
    
    
  
  
  
  
  
  
       
         
  
    
    
    
    
    
    
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

(in thousands, except per share data) 

Denominator: 

Weighted average basic shares 

Weighted average common shares outstanding 

Weighted average diluted shares 

Weighted average common shares outstanding 

Effect of potentially dilutive securities (a) 
Unvested restricted stock awards 
Warrants 
Convertible preferred stock 
Total weighted average diluted shares 

Basic earnings (loss) attributable to common shareholders: 

Continuing operations 
Discontinued operations 
Basic earnings (loss) per share - net income (loss) attributable to common shareholders 

Diluted earnings (loss) attributable to common shareholders: 

Continuing operations 
Discontinued operations 
Diluted earnings (loss) per share - net income (loss) attributable to common shareholders 

  $ 
  $ 
  $ 

  $ 
  $ 
  $ 

Years ended December 31,   
2021   

2022     

  $  

22,961     $  

22,537   

22,961       

22,537   

596       
811       
936       
25,304       

1.36     $ 
(0.30 )   $ 
1.06     $ 

1.25     $ 
(0.27 )   $ 
0.98     $ 

—   
—   
—   
22,537   

(0.22 ) 
0.18   
(0.04 ) 

(0.22 ) 
0.18   
(0.04 ) 

(a)  Potentially dilutive securities consist of unvested restricted stock awards, warrants and convertible preferred stock. Because the Company is 
reporting  a  loss  from  continuing  operations  attributable  to  common  shareholders  for  the  year ended  December  31,  2021, all  potentially 
dilutive securities outstanding were excluded from the calculation of diluted loss from continuing operations per share since their inclusion 
would have been anti-dilutive. 

Basic earnings (loss) per share excludes dilution and is computed by dividing income (loss) attributable to common shareholders by the 
weighted-average number of common shares outstanding for the period.  Diluted earnings (loss) per share is calculated using weighted-
average diluted shares. Weighted-average diluted shares is calculated by adding the effect of potentially dilutive securities to weighted-
average common shares outstanding.  Potentially dilutive securities are excluded from the diluted earnings (loss) per share computation 
in loss periods and when the applicable exercise price is greater than the market price on the period end date as their effect would be 
anti-dilutive. 

The following weighted-average potentially dilutive securities are not included in the diluted earnings (loss) per share calculations above 
because they would have had an antidilutive effect on the earnings (loss) per share: 

Unvested restricted stock awards 
Warrants 
Convertible preferred stock 
Total 

Years ended December 31,   
2021   
1,252,754   
4,573,765   
1,060,831   
6,887,350   

2022     
550,528       
—       
—       
550,528       

NOTE 17 STOCK-BASED COMPENSATION 

On  September  21,  2020,  the  Company’s  shareholders  approved  the  2020  Equity  Incentive  Plan  (the  “2020  Plan”).  The  2020  Plan 
replaced the Company’s previous 2013 Equity Incentive Plan (the “2013 Plan”) with respect to the granting of future equity awards. 
The 2020 Plan permits the grant of Nonqualified Stock Options, Incentive Stock Options, Stock Appreciation Rights, Restricted Shares, 
Restricted Stock Units, Performance Share Awards, Dividend Equivalent Rights, Other Stock-Based Awards and Cash-Based Awards 
(collectively “Awards”). Under the 2020 Plan, an aggregate of 1.6 million common shares will be available for all Awards, subject to 
adjustment in the event of certain corporate transactions.  

86 

  
  
  
       
         
  
       
         
  
       
         
  
    
       
         
  
    
    
    
    
       
         
  
       
         
  
  
  
  
  
  
  
  
  
    
    
    
    
  
 
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

(a)  

Restricted Stock Awards of the Company 

Under the 2013 Plan, the Company granted 500,000 restricted common stock awards to an officer on September 5, 2018 (the “2018 
Restricted  Stock  Award”).  The  2018  Restricted  Stock  Award  shall  become  fully  vested  and  the  restriction  period  shall  lapse  as  of 
March 28, 2024 subject to the officer’s continued employment through the vesting date. The 2018 Restricted Stock Award is amortized 
on a straight-line basis over the requisite service period. The grant-date fair value of the 2018 Restricted Stock Award was determined 
using the closing price of Kingsway common stock on the date of grant. Total unamortized compensation expense related to unvested 
2018 Restricted Stock Award at December 31, 2022 was $0.5 million. 

Under the 2020 Plan, the Company has granted restricted common stock awards to certain officers of the Company during 2022 and 
2021 (the “2020 Plan Restricted Stock Awards”). The 2020 Plan Restricted Stock Awards vest according to a graded vesting schedule 
and  shall  become  fully  vested  subject  to  the  officers’  continued  employment  through  the  applicable  vesting  dates.  The  2020 
Plan Restricted Stock Awards are amortized on a straight-line basis over the requisite service periods. The grant-date fair values of the 
2020 Plan Restricted Stock Awards were determined using the closing price of Kingsway common stock on the dates of grant. During 
the year ended December 31, 2022, 130,918 shares of the 2020 Plan Restricted Stock Awards became fully vested.  Total unamortized 
compensation expense related to unvested 2020 Plan Restricted Stock Awards at December 31, 2022 was $2.9 million. 

The following table summarizes the activity related to unvested 2020 Plan Restricted Stock Awards and 2018 Restricted Stock Award 
(collectively “Restricted Stock Awards”) during the year ended December 31, 2022: 

Unvested at December 31, 2021 

Granted 
Vested 
Cancelled for Tax Withholding 

Unvested at December 31, 2022 

Number of 
Restricted 
   Stock Awards      

Weighted-
Average 
Grant Date Fair 
Value 
(per Share) 

1,252,754     $ 
25,111       
(73,437 )     
(57,481 )     
1,146,947     $ 

5.09   
7.25   
4.67   
4.67   
5.19   

The unvested balance at December 31, 2022 in the table above is comprised of 646,947 shares of the 2020 Plan Restricted Stock Awards 
and 500,000 shares of the 2018 Restricted Stock Award. 

Stock-based  compensation  expense  related  to  the Restricted  Stock  Awards was  $1.0  million  and  $2.1  million  for  the  years  ended 
December 31, 2022 and December 31, 2021, respectively. 

(b)  

Restricted Stock Awards of PWSC 

PWSC granted 1,000 restricted Class B common stock awards (“2018 PWSC RSA”) to an officer of PWSC pursuant to an agreement 
dated  September  7,  2018.  The  2018  PWSC  RSA  contained both  a  service  and  a  performance  condition  that  affected vesting.  On 
December 18, 2020, the 2018 PWSC RSA was amended to modify the vesting terms related to the service and performance condition 
(“Modified PWSC RSA”). 

PWSC granted 250 restricted Class B common stock awards to an officer of PWSC pursuant to an agreement dated December 18, 2020 
(“2020 PWSC RSA”). The 2020 PWSC RSA contained both a service and a performance condition that affected vesting. 

As discussed in Note 5, “Disposal and Discontinued Operations,” the Company sold PWSC on July 29, 2022; therefore there are no 
outstanding Modified PWSC RSA and 2020 PWSC RSA reported in the consolidated balance sheet at December 31, 2022. 

The  service  condition  for  the  Modified  PWSC  RSA  and  the  2020  PWSC  RSA  vested  according  to a  graded vesting  schedule.  The 
performance condition was based on the internal rate of return of PWSC. The grant-date fair value of the Modified PWSC RSA and the 
2020 PWSC RSA were estimated using an internal valuation model. See Note 23, “Fair Value of Financial Instruments,” for further 
discussion related to the valuation of the Modified PWSC RSA and the 2020 PWSC RSA. 

The Modified PWSC RSA and the 2020 PWSC RSA included a noncontingent put option that was exercisable between February 20, 
2022 and February 20, 2023. Since the put option is exercisable less than six months after the vesting of certain shares, the compensation 
expense related to these shares was classified as a liability and included in accrued expenses and other liabilities in the consolidated 
balance sheet at December 31, 2021.  

87 

  
  
  
    
  
    
  
  
  
    
  
  
  
    
    
    
    
    
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

On February 20, 2022, both the service condition and performance condition of the Modified PWSC RSA became fully vested.  During 
the year ended December 31, 2022, 437.50 shares of the Modified RSA became fully vested.  At December 31, 2022 and December 31, 
2021, there were zero and 437.50 unvested shares, respectively, of the Modified PWSC RSA with a weighted-average grant date fair 
value of $1,672 per share.  Total unamortized compensation expense related to the Modified PWSC RSA at December 31, 2022 was zero. 

On February 20, 2022, both the service condition and performance condition of the 2020 PWSC RSA became fully vested.  During the 
year ended December 31, 2022, 109.38 shares of the 2020 PWSC RSA became fully vested.  At December 31, 2022 and December 31, 
2021, there were zero and 109.38 unvested shares, respectively, of the 2020 PWSC RSA with a weighted-average grant date fair value 
of $1,672 per share.  Total unamortized compensation expense related to the 2020 PWSC RSA at December 31, 2022 was zero. 

Stock-based compensation expense related to the Restricted Stock Awards of PWSC was $2.8 million and $1.2 million for the years 
ended December 31, 2022 and December 31, 2021, respectively. 

(c)  

Restricted Common Unit Awards of Ravix 

Ravix LLC granted 199,000 restricted Class B common unit awards to an officer of Ravix pursuant to an agreement dated October 1, 
2021 (“2021 Ravix RUA”). The 2021 Ravix RUA vests based on service and the achievement of criteria based on the internal rate of 
return (“IRR”) of Ravix.  

The  grant-date  fair  value  of  the 2021 Ravix  RUA  was  estimated  using  the  Black-Scholes  option  pricing  model,  using  the  following 
assumptions: expected term of four years, expected volatility of 75%, expected dividend yield of zero, and risk-free interest rate of 0.93%.  

On  October  1,  2021,  83,333  shares,  representing  one half  of  the  service  condition  for  the 2021  Ravix  RUA, became  fully  vested. 
The remainder of the service condition vests according to a graded vesting schedule and shall become fully vested subject to the officer’s 
continued employment through the applicable vesting dates.  

On November 1, 2022, the Company modified the inputs related to the IRR portion of the 2021 Ravix RUA to be based on the combined 
internal rate of return of Ravix and CSuite.  The modified portion of the awards was probable of vesting both immediately before and 
after the modification.  As a result, the fair value of the award that is subject to the IRR was measured at the modification date and 
compared to the fair value of the modified portion of the award immediately prior to the modification, with the difference resulting in 
incremental  compensation  expense  of  less  than $0.1  million.  The  incremental  fair  value  was  estimated  using  the  Monte  Carlo 
simulation model, using the following assumptions at the modification date: expected term of 2.92 years, expected volatility of 72% and 
risk-free interest rate of 4.44%; and the following assumptions prior to the modification: expected term of 2.92 years, expected volatility 
of 58% and risk-free interest rate of 4.44%.  

During the year ended December 31, 2022, 24,306 shares of the 2021 Ravix RUA became fully vested.  At December 31, 2022, there 
were 91,361 unvested shares of the 2021 Ravix RUA with a weighted-average grant date fair value of $3.08 per share. Total unamortized 
compensation expense related to unvested 2021 Ravix RUA at December 31, 2022 was $0.3 million. 

Stock-based compensation expense related to the 2021 Ravix RUA was $0.1 million and $0.3 million for the years ended December 31, 
2022 and December 31, 2021, respectively. 

(d)  

Restricted Common Unit Awards of SNS 

Pegasus  LLC granted  75,000 restricted  Class  B  common  unit  awards to  an  officer  of  SNS  pursuant  to  an  agreement  dated 
November 18, 2022 (“SNS RUA”). The SNS RUA vests based on service and the achievement of criteria based on the IRR of SNS. 

The  grant-date  fair  value  of  the SNS  RUA  was  estimated  using  the  Monte  Carlo simulation model,  using  the  following 
assumptions: expected term of four years, expected volatility of 85% and risk-free interest rate of 4.09%. 

On  November  18,  2022,  25,000  shares,  representing  one half  of  the  service  condition  for  the SNS  RUA, became  fully  vested. 
The remainder of the service condition vests according to a graded vesting schedule and shall become fully vested subject to the officer’s 
continued employment through the applicable vesting dates.  

At December 31, 2022, there were 50,000 unvested shares of the SNS RUA with a weighted-average grant date fair value of $5.95 per 
share. Total unamortized compensation expense related to unvested SNS RUA at December 31, 2022 was $0.3 million. 

Stock-based compensation expense related to the SNS RUA was $0.2 million for the year ended December 31, 2022. 

88 

  
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

(e)  

Employee Share Purchase Plan 

The Company has an employee share purchase plan (“ESPP Plan”) whereby qualifying employees can choose each year to have up to 
5% of their annual base earnings withheld to purchase the Company’s common shares. After one year of employment, the Company 
matches 100% of the employee contribution amount, and the contributions vest immediately. All contributions are used by the plan 
administrator to purchase common shares in the open market. The Company’s contribution is expensed as paid and for the years ended 
December 31, 2022 and December 31, 2021 totaled $0.2 million and $0.2 million, respectively. 

NOTE 18 EMPLOYEE BENEFIT PLAN 

The Company maintains a defined contribution plan in the United States for all of its qualified employees. Qualifying employees can 
choose to voluntarily contribute up to 60% of their annual earnings subject to an overall limitation of $20,500 and $19,500 in 2022 and 
2021,  respectively.  The  Company  matches  an  amount  equal  to  50%  of  each  participant’s  contribution,  limited  to  the  lesser  of 
contributions up to 5% of a participant’s earnings or $7,250. 

The contributions for the plan vest based on years of service with 100% vesting after five years of service. The Company’s contribution 
is  expensed  as  paid  and  for  the  years  ended  December  31,  2022  and  December  31,  2021  totaled  $0.5  million  and $0.4 million, 
respectively. All Company obligations to the plans were fully funded as of December 31, 2022. 

NOTE 19 REDEEMABLE CLASS A PREFERRED STOCK 

On  May  13,  2013,  the  Company’s  shareholders  approved  an  amendment  to  the  Company’s  Articles  of  Incorporation  to  create  an 
unlimited number of zero par value class A preferred shares. The Company’s Board of Directors have the ability to fix the designation, 
rights, privileges, restrictions and conditions attaching to the shares of each series of preferred shares. The preferred shares have priority 
over the common shares. 

There were 149,733 and 169,733 shares of Preferred Shares outstanding at December 31, 2022 and December 31, 2021, respectively. 
Each Preferred Share is convertible into 6.25 common shares at a conversion price of $4.00 per common share any time at the option of 
the  holder  prior  to  the  redemption  date.  During 2022 and  2021, 20,000 and  13,143 Preferred  Shares,  respectively, were  converted 
into 125,000  and 82,143  common  shares,  respectively,  at  the  conversion  price  of  $4.00  per  common  share,  or $0.5 million 
and $0.3 million, respectively, at the option of the holders. As of December 31, 2022, the maximum number of common shares issuable 
upon conversion of the Preferred Shares is 935,831 common shares. 

The Preferred Shares are not entitled to vote. The holders of the Preferred Shares are entitled to receive fixed, cumulative, preferential 
cash dividends at a rate of $1.25 per Preferred Share per year. The cash dividend rate shall be revised to $1.875 per Preferred Share per 
year if the dividend accumulates for a period greater than 30 consecutive months from the date of the most recent dividend payment. 
On and after February 3, 2016, the Company may redeem all or any part of the then outstanding Preferred Shares for the price of $28.75 
per Preferred Share, plus accrued but unpaid dividends thereon, whether or not declared, up to and including the date specified for 
redemption.  The  Company  will  redeem  any  Preferred  Shares  not  previously  converted  into  common  shares,  and  which  remain 
outstanding on the redemption date, for the price of $25.00 per Preferred Share, plus accrued but unpaid dividends, whether or not 
declared, up to and including the date specified for redemption. 

As  discussed  in  “Note  2(s),  “Summary  of  Significant  Accounting  Policies -  Holding  company  liquidity,”  the outstanding  Preferred 
Shares were required to be redeemed by the Company on April 1, 2021 (“Redemption Date”). However, the Company has exercised its 
right to defer payment of interest on its outstanding subordinated debt (“trust preferred securities”) and, therefore is prohibited from 
redeeming any shares of its capital stock while payment of interest on the trust preferred securities is being deferred.  As such, the 
Preferred Shares were not redeemed on the Redemption Date and instead remain outstanding with a redemption value of $6.0 million 
as  of December  31,  2022.  None  of  the  terms  of  the  Preferred  Shares  have  changed  after  the  Redemption  Date.   The  Preferred 
Shares continue to be convertible into common shares at the discretion of the holder, and will accrue dividends until such time that either 
(i) the shares are converted at the discretion of the holder or (ii) the interest on the trust preferred securities is no longer deferred and the 
Company redeems the outstanding Preferred Shares at that time.   

The Company accrues dividends through additional paid-in-capital at the stated coupon.  At December 31, 2022 and December 31, 2021, 
accrued  dividends  of $2.3 million  and $2.3 million  were  included  in  Class  A  preferred  stock  in  the  consolidated  balance  sheets.  The 
redemption amount of the Preferred Shares was $6.0 million and $6.5 million at December 31, 2022 and December 31, 2021, respectively. 

89 

  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

In  accordance  with  FASB  ASC  Topic  480-10-S99-3A,  SEC  Staff  Announcement:  Classification  and  Measurement  of  Redeemable 
Securities, redemption features not solely within the control of the issuer are required to be presented outside of permanent equity on 
the consolidated balance sheets. As described above, the holder has the option to convert the Preferred Shares at any time; however, if 
not converted, they are required to be redeemed when the Company has sufficient legally available funds and is not otherwise prohibited 
from doing so.  As such, the Preferred Shares are presented in temporary or mezzanine equity on the consolidated balance sheets. 

NOTE 20 SHAREHOLDERS’ EQUITY 

The Company is authorized to issue 50,000,000 shares of zero par value common stock. There were 23,190,080 and 22,882,614 shares 
of common stock outstanding at December 31, 2022 and December 31, 2021, respectively. 

There were no dividends declared during the years ended December 31, 2022 and December 31, 2021. 

As  described  in  Note  19,  “Redeemable  Class  A  Preferred  Stock”, during 2022 and 2021,  20,000 and  13,143 Preferred  Shares, 
respectively,  were  converted  into 125,000 and 82,143 common  shares,  respectively.   As  a  result, $0.8 million and $0.5 million  was 
reclassified from redeemable Class A preferred stock to additional paid-in capital on the consolidated balance sheets at December 31, 
2022 and December 31, 2021, respectively. 

There were 247,450 shares of treasury stock outstanding at December 31, 2022 and December 31, 2021.  The Company records treasury 
stock at cost. 

At December 31, 2022, the Company has 4,464,736 warrants outstanding that expire on September 15, 2023. The warrants are recorded 
in shareholders’ equity and entitle each subscriber to purchase one common share of Kingsway at an exercise price of $5.00 for each 
warrant.  During  2022 and 2021,  warrants  to  purchase 109,029 and  350,000 shares  of  common  stock,  respectively, were  exercised, 
resulting in cash proceeds of $0.5 million and $1.8 million, respectively. 

In early January 2023, a holder exercised 611,547 of warrants, resulting in cash proceeds to the Company of $3.1 million.  The Company 
has seen an increase in warrant exercises in 2023, compared to prior periods.  

NOTE 21 ACCUMULATED OTHER COMPREHENSIVE INCOME  

The table below details the change in the balance of each component of accumulated other comprehensive income, net of tax, for the 
years ended December 31, 2022 and December 31, 2021 as it relates to shareholders’ equity attributable to common shareholders on the 
consolidated balance sheets. 

(in thousands) 

Balance, December 31, 2020 

Other comprehensive loss arising during the period 
Amounts reclassified from accumulated other 
comprehensive income 

Net current-period other comprehensive loss 

     Change in        
Fair Value 
of 
Debt 
     Attributable     
to 
     Instrument-      

   Unrealized        
   Gains 
   (Losses) on       Foreign 
   Available-       Currency 

Total 
     Accumulated    
Other 
    Comprehensive   
   Investments     Adjustments      Credit Risk       Income (Loss)   
38,059   
  $ 

     Translation       Specific 

41,129     $ 

(3,286 )   $ 

for-Sale 

216     $ 

(463 )     

—       

(6,844 )     

(7,307 ) 

27       
(436 )     

—       
—       

—       
(6,844 )     

27   
(7,280 ) 

90 

  
  
  
      
        
        
         
  
  
    
  
      
  
  
  
  
    
  
      
  
    
      
  
  
  
  
    
      
  
  
  
      
  
  
  
    
  
  
  
  
  
  
      
        
        
         
  
    
    
    
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

(in thousands) 

Balance, December 31, 2021 

     Change in        
Fair Value 
of 
Debt 
     Attributable     
to 
     Instrument-      

   Unrealized        
   Gains 
   (Losses) on       Foreign 
   Available-       Currency 

Total 
     Accumulated    
Other 
    Comprehensive   
   Investments     Adjustments      Credit Risk       Income (Loss)   
30,779   
  $ 

     Translation       Specific 

34,285     $ 

(3,286 )   $ 

(220 )   $ 

for-Sale 

Other comprehensive loss arising during the period 
Amounts reclassified from accumulated other 
comprehensive income 

Net current-period other comprehensive loss 
Balance, December 31, 2022 

(2,266 )     

—       

(1,930 )     

(4,196 ) 

22       
(2,244 )     
(2,464 )   $ 

—       
—       
(3,286 )   $ 

—       
(1,930 )     
32,355     $ 

22   
(4,174 ) 
26,605   

  $ 

It should be noted that the consolidated statements of comprehensive income (loss) present the components of other comprehensive loss, 
net  of  tax,  only  for  the  years  ended  December  31,  2022  and  December  31,  2021  and  inclusive  of  the  components  attributable  to 
noncontrolling interests in consolidated subsidiaries. 

Components of accumulated other comprehensive income were reclassified to the following lines of the consolidated statements of 
operations for the years ended December 31, 2022 and December 31, 2021: 

(in thousands) 

Reclassification of accumulated other comprehensive income from unrealized gains (losses) 
on available-for-sale investments to: 

Net realized gains 
Other-than-temporary impairment loss 
Income (loss) from continuing operations before income tax expense (benefit) 
Income tax expense (benefit) 

Income (loss) from continuing operations 
(Loss) income from discontinued operations, net of taxes 
Net income 

Years ended December 31,   
2021   

2022     

  $ 

  $ 

(22 )   $ 
—       
(22 )     
—       
(22 )     
—       
(22 )   $ 

(27 ) 
—   
(27 ) 
—   
(27 ) 
—   
(27 ) 

NOTE 22 SEGMENTED INFORMATION 

The  Company  reports  segment  information  based  on  the  “management” approach.  The management  approach designates  the  internal 
reporting  used  by  management  for  making  decisions  and  assessing  performance  as  a  source  of  the  Company’s  reportable  operating 
segments.  The  Company  conducts  its  business  through  the  following  two reportable  segments:  Extended  Warranty  and  Kingsway 
Search Xcelerator. 

Prior to the fourth quarter of 2022, the Company conducted its business through a third reportable segment, Leased Real Estate. Leased 
Real Estate included the following subsidiaries of the Company: CMC and VA Lafayette.  As further discussed in Note 5, “Disposal 
and Discontinued Operations,” both CMC and VA Lafayette have been classified as discontinued operations and the results of their 
operations are reported separately for all periods presented.  As such, the Leased Real Estate segment no longer exists and all segmented 
information has been restated to exclude the Leased Real Estate segment for all periods presented.  

Extended Warranty Segment 

Extended Warranty includes the following subsidiaries of the Company: IWS, Geminus, PWI, PWSC and Trinity (collectively, “Extended 
Warranty”).  As discussed in Note 5, “Disposal and Discontinued Operations,” the Company disposed of PWSC on July 29, 2022.  The 
earnings of PWSC are included in the consolidated statements of operations and the segment disclosures through the disposal date.    

91 

      
        
        
         
  
  
    
  
      
  
  
  
  
    
  
      
  
    
      
  
  
  
  
    
      
  
  
  
      
  
  
  
    
  
  
  
  
  
  
      
        
        
         
  
    
    
    
  
  
  
  
  
      
        
  
    
    
    
    
    
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

IWS is a licensed motor vehicle service agreement company and is a provider of after-market vehicle protection services distributed 
by credit unions in 25 states and the District of Columbia to their members, with customers in all 50 states. 

Geminus primarily sells vehicle service agreements to used car buyers across the United States, through its subsidiaries, Penn and Prime. 
Penn  and  Prime  distribute  these  products  in  39  and  40  states,  respectively,  via  independent  used  car  dealerships  and  franchised 
car dealerships. 

PWI markets, sells and administers vehicle service agreements to used car buyers in all fifty states via independent used car and franchise 
network of approved automobile and motorcycle dealer partners. PWI’s business model is supported by an internal sales and operations 
team and partners with American Auto Shield in three states with a “white label” agreement.  PWI also has a “white label” agreement 
with a third-party that sells and administers a GAP product in certain states. 

PWSC sells home warranty products and provides administration services to homebuilders and homeowners across the United States. 
PWSC  distributes  its  products  and  services  through  an  in  house  sales  team  and  through  insurance  brokers  and  insurance  carriers 
throughout all states except Alaska and Louisiana. 

Trinity  sells  HVAC,  standby  generator,  commercial  LED  lighting  and  commercial  refrigeration  warranty  products  and  provides 
equipment breakdown and maintenance support services to companies across the United States. As a seller of warranty products, Trinity 
markets and administers product warranty contracts for certain new and used products in the HVAC, standby generator, commercial 
LED lighting and commercial refrigeration industries throughout the United States. Trinity acts as an agent on behalf of the third-party 
insurance companies that underwrite and guaranty these warranty contracts. Trinity does not guaranty the performance underlying the 
warranty contracts it sells. As a provider of equipment breakdown and maintenance support services, Trinity acts as a single point of 
contact to its clients for both certain equipment breakdowns and scheduled maintenance of equipment. Trinity will provide such repair 
and breakdown services by contracting with certain HVAC providers. 

Kingsway Search Xcelerator Segment 

Kingsway Search Xcelerator includes the Company’s subsidiaries CSuite, Ravix and SNS.   

CSuite provides financial executive services, for project and interim-staffing engagements, and search services for full-time placements 
for customers throughout the United States.  

Ravix provides outsourced financial services and human resources consulting for short or long duration engagements for customers in 
several states.   

SNS provides healthcare staffing services to acute healthcare facilities on a contract or per diem basis in the United States, primarily 
in California.  

Revenues and Operating Income by Reportable Segment 

Results for the Company’s reportable segments are based on the Company’s internal financial reporting systems and are consistent with 
those  followed  in  the  preparation  of  the  consolidated  financial  statements.  The  following  tables  provide  financial  data  used  by 
management. Segment assets are not allocated for management use and, therefore, are not included in the segment disclosures below. 

Revenues by reportable segment reconciled to consolidated revenues for the years ended December 31, 2022 and December 31, 2021 were: 

(in thousands) 

Revenues: 

Years ended December 31,   
2021   

2022     

Service fee and commission revenue - Extended Warranty 
Service fee and commission revenue - Kingsway Search Xcelerator 

Total revenues 

  $ 

  $ 

74,042     $ 
19,238       
93,280     $ 

74,919   
3,482   
78,401   

92 

  
  
  
  
      
        
  
    
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

The operating income by reportable segment in the following table is before income taxes and includes revenues and direct segment 
costs. Total segment operating income reconciled to the consolidated income (loss) from continuing operations for the years ended 
December 31, 2022 and December 31, 2021 were: 

(in thousands) 

Segment operating income 
Extended Warranty (a) 
Kingsway Search Xcelerator 
Total segment operating income 
Net investment income 
Net realized gains 
Loss on change in fair value of equity investments 
(Loss) gain on change in fair value of limited liability investments, at fair value 
Gain on change in fair value of real estate investments 
Gain on change in fair value of derivative asset option contracts 
Interest expense 
Other revenue and expenses not allocated to segments, net 
Amortization of intangible assets 
Loss on change in fair value of debt 
Gain on disposal of subsidiary 
Gain on extinguishment of debt not allocated to segments 
Income (loss) from continuing operations before income tax expense (benefit) 
Income tax expense (benefit) 
Income (loss) from continuing operations 

Years ended December 31,   
2021   

2022     

  $ 

  $ 

9,879     $ 
3,548       
13,427       
2,305       
1,209       
(26 )     
(1,754 )     
1,488       
16,730       
(8,092 )     
(17,206 )     
(6,133 )     
(4,908 )     
37,917       
—       
34,957       
4,825       
30,132     $ 

12,636   
484   
13,120   
1,575   
1,809   
(242 ) 
2,391   
—   
—   
(6,161 ) 
(11,395 ) 
(4,837 ) 
(3,201 ) 
—   
311   
(6,630 ) 
(3,916 ) 
(2,714 ) 

(a)  For the year ended December 31, 2021, Extended Warranty segment operating income includes gain on extinguishment of debt 
of $2.2 million, related to PPP loan forgiveness directly associated with the respective warranty businesses.  Extended Warranty 
segment operating income before the gain of extinguishment of debt totaled $10.5 million for the year ended December 31, 2021, 
respectively. See Note 12, “Debt” for further discussion. 

NOTE 23 FAIR VALUE OF FINANCIAL INSTRUMENTS 

Fair value is the price that would be received upon sale of an asset or paid to transfer a liability in an orderly transaction between market 
participants at the measurement date. Fair value is best evidenced by quoted bid or ask price, as appropriate, in an active market. Where 
bid or ask prices are not available, such as in an illiquid or  inactive market, the closing price of the most recent transaction of that 
instrument subject to appropriate adjustments as required is used. Where quoted market prices are not available, the quoted prices of 
similar financial instruments or valuation models with observable market-based inputs are used to estimate the fair value. These valuation 
models  may  use  multiple  observable  market  inputs,  including  observable  interest  rates,  foreign  exchange  rates,  index  levels,  credit 
spreads, equity prices, counterparty credit quality, corresponding market volatility levels and option volatilities. Minimal management 
judgment is required for fair values calculated using quoted market prices or observable market inputs for models. Greater subjectivity 
is required when making valuation adjustments for financial instruments in inactive markets or when using models where observable 
parameters do not exist. Also, the calculation of estimated fair value is based on market conditions at a specific point in time and may 
not be reflective of future fair values. For the Company’s financial instruments carried at cost or amortized cost, the book value is not 
adjusted to reflect increases or decreases in fair value due to market fluctuations, including those due to interest rate changes, as it is the 
Company’s intention to hold them until there is a recovery of fair value, which may be to maturity. 

The Company employs a fair value hierarchy to categorize the inputs it uses in valuation techniques to measure the fair value. The 
following fair value hierarchy is used in selecting inputs, with the highest priority given to Level 1: 

•  Level 1 – Quoted prices for identical instruments in active markets. 

•  Level 2 – Quoted prices for similar instruments in active markets; quoted prices for identical or similar instruments in markets 

that are not active; and model-derived valuations in which all significant inputs are observable in active markets. 

•  Level 3 – Valuations derived from valuation techniques in which one or more significant inputs are not observable. 

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KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

The  Company  classifies  its  investments  in  fixed  maturities  as  available-for-sale  and  reports  these  investments  at  fair  value.  The 
Company’s  equity  investments,  limited  liability  investments,  at  fair  value,  real  estate  investments,  subordinated  debt, stock-based 
compensation  liabilities,  derivative  contracts  (interest  rate  swap  and  trust  preferred  debt  repurchase  options)  and  contingent 
consideration are measured and reported at fair value. 

Fixed maturities - Fair values of fixed maturities for which no active market exists are derived from quoted market prices of similar 
instruments or other third-party evidence. All classes of the Company’s fixed maturities, primarily consisting of investments in US. 
Treasury bills and government bonds; obligations of states, municipalities and political subdivisions; mortgage-backed securities; and 
corporate securities, are classified as Level 2. Level 2 is applied to valuations based upon quoted prices for similar assets in active 
markets; quoted prices for identical or similar assets in markets that are inactive; or valuations based on models where the significant 
inputs are observable or can be corroborated by observable market data. 

The  Company  engages  a  third-party  vendor  who  utilizes  third-party  pricing  sources  and  primarily  employs  a  market  approach  to 
determine the fair values of our fixed maturities. The market approach includes primarily obtaining prices from independent third-party 
pricing services as well as, to a lesser extent, quotes from broker-dealers. Our third-party vendor also monitors market indicators, as 
well as industry and economic events, to ensure pricing is appropriate. All classes of our fixed maturities are valued using this technique. 
The Company has obtained an understanding of our third-party vendor’s valuation methodologies and inputs. Fair values obtained from 
our third-party vendor are not adjusted by the Company. 

The following is a description of the significant inputs, by asset class, used by the third-party pricing services to determine the fair values 
of our fixed maturities included in Level 2: 

•  U.S. government, government agencies and authorities are generally priced using the market approach. Inputs generally consist 

of trades of identical or similar securities, quoted prices in inactive markets and maturity. 

• 

States, municipalities and political subdivisions are generally priced using the market approach. Inputs generally consist of 
trades of identical or similar securities, quoted prices in inactive markets, new issuances and credit spreads. 

•  Mortgage-backed securities are generally priced using the market approach. Inputs generally consist of trades of identical or 
similar securities, quoted prices in inactive markets, expected prepayments, expected credit default rates, delinquencies and 
issue specific information including, but not limited to, collateral type, seniority and vintage. 

•  Corporate securities are generally priced using the market approach using pricing vendors. Inputs generally consist of trades 
of identical or similar securities, quoted prices in inactive markets, issuer rating, benchmark yields, maturity and credit spreads. 

Equity investments - Fair values of equity investments, including warrants, reflect quoted market values based on latest bid prices, where 
active markets exist, or models based on significant market observable inputs, where no active markets exist. 

Limited liability investments, at fair value - Limited liability investments, at fair value include the underlying investments of Net Lease 
and Argo Holdings. Net Lease owns investments in limited liability companies that hold investment properties. Argo Holdings makes 
investments in limited liability companies and limited partnerships that hold investments in search funds and private operating companies. 

•  The fair value of Net Lease’s investments in limited liability companies is based upon the net asset values of the underlying 
investments in companies as a practical expedient to estimate fair value. The Company applies the net asset value practical 
expedient  to  Net  Lease’s  limited  liability  investments  on  an  investment-by-investment  basis  unless  it  is  probable  that  the 
Company will sell a portion of an investment at an amount different from the net asset value of the investment. Investments 
that  are  measured  at  fair value using  the net  asset  value practical  expedient  are not  required  to  be classified using  the fair 
value hierarchy. 

•  The fair value of Argo Holdings’ limited liability investments that hold investments in search funds is based on the initial 
investment in the search funds. The fair value of Argo Holdings’ limited liability investments that hold investments in private 
operating companies is valued using a market approach including valuation multiples applied to corresponding performance 
metrics, such as earnings before interest, tax, depreciation and amortization; revenue; or net earnings. The selected valuation 
multiples were estimated using multiples provided by the investees and review of those multiples in light of investor updates, 
performance reports, financial statements and other relevant information. These investments are categorized in Level 3 of the 
fair value hierarchy. 

94 

  
  
  
  
  
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

Real estate investments - The fair value of real estate investments involves a combination of the market and income valuation techniques. 
Under this approach, a market-based capitalization rate is derived from comparable transactions, adjusted for any unique characteristics 
of each asset, and applied to the asset under consideration. The cap rates used during underwriting and subsequent valuation incorporate 
the  consideration  of  risks  of  vacancy  and  collection  loss,  administrative  costs  of  owning  net  leased  assets  and  possible  capital 
expenditures that could be determined a landlord expense. These investments are categorized in Level 3 of the fair value hierarchy. 

Subordinated debt - The fair value of the subordinated debt is calculated using a model based on significant market observable inputs 
and inputs developed by a third-party. These inputs include credit spread assumptions developed by a third-party and market observable 
swap rates. The subordinated debt is categorized in Level 2 of the fair value hierarchy. 

Stock-based compensation liabilities - Certain of the restricted stock awards granted by PWSC were classified as a liability prior to the 
sale of PWSC on July 29, 2022. Liability-classified awards are measured and reported at fair value and are included in accrued expenses 
and other liabilities in the consolidated balance sheets. The fair value of the liability-classified awards granted by PWSC were estimated 
using an internal valuation model without relevant observable market inputs. The significant inputs used in the model include a valuation 
multiple  applied  to  trailing  twelve  month  earnings  before  interest,  tax,  depreciation  and  amortization.  Liability-classified  PWSC 
restricted stock awards were categorized in Level 3 of the fair value hierarchy. 

Derivative  contract  interest  rate  swap -  As  described  in Note  11,  “Derivatives,” the  Company  entered  into  an  interest  rate  swap 
agreement effective April 1, 2021 to convert the variable interest rate on a portion of the 2020 KWH Loan to a fixed interest rate.  The 
interest rate swap contract is measured and reported at fair value and is included in other receivables and accrued expenses and other 
liabilities in the consolidated balance sheets at December 31, 2022 and December 31, 2021, respectively. The fair value of the interest 
rate swap contract is estimated using inputs which the Company obtains from the counterparty and is determined using a discounted 
cash flow analysis on the expected cash flows of the derivative.  The discounted cash flow valuation technique reflects the contractual 
term of the derivative contract, including the period to maturity, and uses observable market based inputs, including quoted mid-market 
prices or third-party consensus pricing, interest rate curves and implied volatilities.  The interest rate swap contract is categorized in 
Level 2 of the fair value hierarchy. 

Derivative  contracts  -  trust  preferred  debt  repurchase  options - As  described  in Note  11,  “Derivatives,” the  Company  entered  into 
three TruPs Options contracts during the third quarter of 2022.  The TruPs Options contracts are measured and reported at fair value and 
are included  in  other  assets  in  the  consolidated  balance  sheet at  December  31,  2022.  The  fair  value  of  the  TruPs  Options 
contracts are estimated  using  the  binomial  lattice model.   Key  inputs  in  the  valuation  include  credit  spread  assumptions, interest 
rate volatility,  debt  coupon  interest  rate and  time  to  maturity.   The  TruPs  Options  contracts  are  categorized  in  Level  3 of  the  fair 
value hierarchy.  

Contingent  consideration -  The  consideration  for  the  Company’s  acquisitions  of  Ravix  and  CSuite  includes future  payments  to  the 
former  owners  that  are contingent  upon  the  achievement  of  certain  targets  over  future  reporting  periods.  Liabilities  for  contingent 
consideration are measured and reported  at  fair value  and are  included  in  accrued  expenses  and  other  liabilities  in  the  consolidated 
balance  sheets.  Contingent  consideration  liabilities  are  revalued  each  reporting  period.  Changes  in  the  fair  value  of  contingent 
consideration liabilities can result from changes to one or multiple inputs, including adjustments to the discount rates or changes in the 
assumed achievement or timing of any targets. Any changes in fair value are reported in the consolidated statements of operations as 
non-operating other (expense) revenue. The contingent consideration liabilities are categorized in Level 3 of the fair value hierarchy. 

•  The  fair  value  of Ravix’s contingent  consideration  liability is  estimated  by  applying  the Monte  Carlo simulation  method to 
forecast achievement of gross profit which may result in up to $4.5 million in total payments to the former owners of Ravix 
through October 2024.  Key inputs in the valuation include forecasted gross profit, gross profit volatility, discount rate and 
discount term. 

•  The fair value of CSuite’s contingent consideration liability is estimated by applying the Monte Carlo simulation method to 
forecast  achievement  of  gross  revenue which may  result  in  up  to  $3.6  million  in  total  payments  to  the  former  owners  of 
CSuite through  November  2025.   Key  inputs  in  the  valuation  include  forecasted  gross  revenue,  gross  revenue  volatility, 
discount rate and discount term. 

95 

  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

Assets and Liabilities Measured at Fair Value on a Recurring Basis 

The balances of the Company’s financial assets and liabilities measured at fair value on a recurring basis by level within the fair value 
hierarchy as of December 31, 2022 and December 31, 2021 are as follows. Certain investments in limited liability companies that are 
measured at fair value using the net asset value practical expedient are not required to be classified using the fair value hierarchy, but 
are presented in the following tables to permit reconciliation of the fair value hierarchy to the amounts presented in the consolidated 
balance sheets: 

(in thousands) 

Fair Value Measurements at the End of the Reporting Period Using 

December 31, 2022   

     Quoted 
     Prices in 
     Active 
     Markets for      
Identical 
     Assets 

Total 

(Level 1) 

     Significant        
Other 

     Significant        

     Observable      Unobservable      Measured at   
Inputs 
(Level 3) 

     Net Asset 
     Value 

Inputs 
(Level 2) 

Recurring fair value measurements 

Assets: 
Fixed maturities: 

U.S. government, government agencies and 
authorities 
States, municipalities and political subdivisions 
Mortgage-backed 
Asset-backed 
Corporate 
Total fixed maturities 

  $ 

Equity investments: 
Common stock 
Total equity investments 

Limited liability investments, at fair value 
Derivative contract - interest rate swap 
Derivative contract - trust preferred debt 
repurchase options 
Total assets 

Liabilities: 
Subordinated debt 
Contingent consideration 
Total liabilities 

  $ 

  $ 

  $ 

15,080     $ 
2,232       
8,412       
1,610       
10,257       
37,591       

153       
153       
17,059       
326       

—     $ 
—       
—       
—       
—       
—       

153       
153       
—       
—       

15,080     $ 
2,232       
8,412       
1,610       
10,257       
37,591       

—     $ 
—       
—       
—       
—       
—       

—   
—   
—   
—   
—   
—   

—       
—       
—       
326       

—       
—       
3,196       
—       

—   
—   
13,863   
—   

19,034       
74,163     $ 

—       
153     $ 

—       
37,917     $ 

19,034       
22,230     $ 

—   
13,863   

67,811     $ 
3,218       
71,029     $ 

—     $ 
—       
—     $ 

67,811     $ 
—       
67,811     $ 

—     $ 
3,218       
3,218     $ 

—   
—   
—   

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KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

(in thousands) 

Fair Value Measurements at the End of the Reporting Period Using 

December 31, 2021   

     Quoted 
     Prices in 
     Active 
     Markets for      
Identical 
     Assets 

Total 

(Level 1) 

     Significant        
Other 

     Significant        

     Observable      Unobservable      Measured 

Inputs 
(Level 2) 

Inputs 
(Level 3) 

at Net 
     Asset Value   

Recurring fair value measurements 

Assets: 
Fixed maturities: 

U.S. government, government agencies 
and authorities 
States, municipalities and political subdivisions 
Mortgage-backed 

  $ 

Asset-backed 
Corporate 
Total fixed maturities 

Equity investments: 
Common stock 
Warrants 
Total equity investments 

Limited liability investments, at fair value 
Real estate investments 
Total assets 

Liabilities: 
Subordinated debt 
Contingent consideration 
Stock-based compensation liabilities 
Derivative contract - interest rate swap 
Total liabilities 

  $ 

  $ 

  $ 

16,223     $ 
1,878       
7,629       
445       
9,491       
35,666       

171       
8       
179       
18,826       
10,662       
65,333     $ 

60,973     $ 
2,458       
1,402       
14       
64,847     $ 

—     $ 
—       
—       
—       
—       
—       

171       
—       
171       
—       
—       
171     $ 

16,223     $ 
1,878       
7,629       
445       
9,491       
35,666       

—       
8       
8       
—       
—       
35,674     $ 

—     $ 
—       
—       
—       
—       
—       

—   
—   
—   
—   
—   
—   

—       
—       
—       
4,022       
10,662       
14,684     $ 

—   
—   
—   
14,804   
—   
14,804   

—     $ 
—       
—       
—       
—     $ 

60,973     $ 
—       
—       
14       
60,987     $ 

—     $ 
2,458       
1,402       
—       
3,860     $ 

—   
—   
—   
—   
—   

97 

    
        
      
  
  
  
  
      
        
        
        
        
  
  
    
  
      
  
      
  
      
    
  
    
  
      
  
      
  
      
    
  
    
  
  
      
    
  
    
  
    
  
    
  
    
  
  
    
  
    
    
    
  
  
  
    
    
    
      
        
        
        
        
  
  
      
        
        
        
        
  
      
        
        
        
        
  
      
        
        
        
        
  
    
    
    
    
    
      
        
        
        
        
  
    
    
    
    
    
  
      
        
        
        
        
  
      
        
        
        
        
  
    
    
    
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

The  following  table  provides  a  reconciliation  of  the  fair  value  of  recurring  Level  3  fair  value  measurements  for  the  years  ended 
December 31, 2022 and December 31, 2021: 

(in thousands) 

Assets: 
Limited liability investments, at fair value: 

Beginning balance 

  $ 

Distributions received 
Realized gains included in net income 
Change in fair value of limited liability investments, at fair value included in net income      
  $ 

Ending balance 
Unrealized (gains) losses on limited liability investments, at fair value held at end 
of period: 

Included in net income 
Included in other comprehensive loss 

Real estate investments: 
Beginning balance 

Realized gains on sale of real estate investments included in net income 

Sale of real estate investments 

Ending balance 
Unrealized gains recognized on real estate investments held at end of period: 

Included in net income 
Included in other comprehensive loss 

Derivative - trust preferred debt repurchase options: 

Beginning balance 

Purchase of options 
Initial valuation of options included in net income 
Change in fair value of derivative assets included in net income 

Ending balance 
Unrealized gains recognized on derivative assets held at end of period: 

Included in net income 
Included in other comprehensive loss 

Ending balance - assets 

Liabilities: 
Contingent consideration: 

Beginning balance 

Issuance of contingent consideration in connection with acquisition 
Settlements of contingent consideration liabilities 
Change in fair value of contingent consideration included in net income 

Ending balance 
Unrealized gains recognized on contingent consideration liabilities held at end of period: 

Included in net income 
Included in other comprehensive loss 

Stock-based compensation liabilities: 
Beginning balance 

Issuance of stock-based compensation awards 
Change in fair value of stock-based compensation liabilities included in net income 
Stock-based compensation liabilities disposed of related to PWSC 

  $ 
  $ 

  $ 

  $ 

  $ 

  $ 

  $ 

  $ 

  $ 

  $ 

  $ 

  $ 
  $ 

  $ 

Ending balance 
  $ 
Unrealized gains recognized on stock-based compensation liabilities held at end of period:        
  $ 
  $ 
  $ 

Included in net income 
Included in other comprehensive loss 

Ending balance - liabilities 

98 

Years ended December 31,   
2021   

2022     

4,022     $ 
(621 )     
607       
(812 )     
3,196     $ 

(812 )   $ 
—     $ 

10,662     $ 
1,488       
(12,150 )     
—     $ 

—     $ 
—       

—     $ 
2,304       
11,412       
5,318       
19,034     $ 

16,730     $ 
—       
22,230     $ 

2,458     $ 
—       
(750 )     
1,510       
3,218     $ 

1,510     $ 
—     $ 

1,402     $ 
—       
2,780       
(4,182 )     
—     $ 

2,780     $ 
—     $ 
3,218     $ 

3,263   
(658 ) 
631   
786   
4,022   

786   
—   

10,662   
—   
—   
10,662   

—   
—   

—   
—   
—   
—   
—   

—   
—   
14,684   

—   
2,195   
—   
263   
2,458   

263   
—   

443   
—   
959   
—   
1,402   

959   
—   
3,860   

  
  
  
      
        
  
      
        
  
    
    
      
        
  
      
        
  
    
    
      
        
  
    
      
        
  
    
    
    
      
        
  
    
      
        
  
      
        
  
    
    
    
      
        
  
      
        
  
    
    
    
        
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for the 
Company’s investments that are categorized as Level 3 at December 31, 2022: 

Categories 

   Fair Value   

Valuation Techniques 

Limited liability investments, at fair value  $ 
Derivative - trust preferred debt 
repurchase options 

  $ 

3,196    Market approach 

19,034    Binomial lattice option approach 

Contingent consideration 

  $ 

3,218    Option-based income approach 

Unobservable 
Inputs 
Valuation multiples    

   Input Value(s)    
1.0x - 9.0x   

Credit spread 
Interest rate volatility   
Debt coupon 
interest rate 
Time to maturity 
(in years) 
Discount rate 
Risk-free rate 
Expected volatility    

8.95 % 
2.3 % 

8.72%-8.87%   

10.4 - 10.59   

8.25 % 
4.44 % 
13.0 % 

The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for the 
Company’s investments that are categorized as Level 3 at December 31, 2021: 

Categories 

   Fair Value   

Valuation Techniques 

Limited liability investments, at fair value  $ 
  $ 
Real estate investments 
  $ 
Contingent consideration 

4,022    Market approach 

10,662    Market and income approach 

2,458    Option-based income approach 

Stock-based compensation liabilities 

  $ 

1,402    Market approach 

Investments Measured Using the Net Asset Value per Share Practical Expedient 

Unobservable 
Inputs 
Valuation multiples    
Cap rates 
Discount rate 
Risk-free rate 
Expected volatility    
Valuation multiple    

   Input Value(s)    
1.0x - 8.0x   

7.5 % 
4.0 % 
0.49 % 
15.0 % 
6.0x   

The following table summarizes investments for which fair value is measured using the net asset value per share practical expedient at 
December 31, 2022: 

Limited liability investments, at fair value 

Category 

thousands)      Unfunded Commitments     Redemption Frequency     
n/a       

13,863       

n/a       

  $ 

The following table summarizes investments for which fair value is measured using the net asset value per share practical expedient at 
December 31, 2021: 

Limited liability investments, at fair value 

Category 

thousands)      Unfunded Commitments     Redemption Frequency     
n/a       

14,804       

n/a       

   $ 

    Redemption   
Notice 
Period 

n/a   

    Redemption   
Notice 
Period 

n/a   

   Fair Value        
(in 

   Fair Value        
(in 

99 

  
    
  
    
       
  
    
       
  
  
    
       
  
    
  
    
       
  
  
    
       
  
  
    
    
  
    
       
  
  
    
       
  
  
  
  
      
  
  
  
  
  
  
  
      
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

Assets and Liabilities Measured at Fair Value on a Nonrecurring Basis 

Certain assets and liabilities are measured at fair value on a nonrecurring basis, including assets that are adjusted for observable price 
changes or written down to fair value as a result of an impairment. For the years ended December 31, 2022 and December 31, 2021, the 
Company did not record any adjustments to the fair value of its investments in private companies for observable price changes. The 
Company  did  not  record any  impairments  related  to  investments  in  private  companies  for  the  years  ended  December  31,  2022  and 
December 31, 2021. To determine the fair value of investments in these private companies, the Company considered rounds of financing 
and third-party transactions, discounted cash flow analyses and market-based information, including comparable transactions, trading 
multiples  and  changes  in  market  outlook,  among  other  factors.  The  Company  has  classified  the  fair  value  measurements  of  these 
investments in private companies as Level 3 because they involve significant unobservable inputs. 

As further discussed in Note 4, “Acquisitions,” the Company acquired Ravix on October 1, 2021 and allocated the purchase price to the 
assets acquired and liabilities assumed. The fair values of intangible assets associated with the acquisition of Ravix were determined to 
be Level 3 under the fair value hierarchy. 

The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for 
these Level 3 measurements: 

Categories 
Customer relationships 

   Fair Value 
  $ 

Valuation Techniques 
4,000    Multi-period excess earnings 

Trade name 

  $ 

2,500    Relief from royalty 

Unobservable Inputs     Input Value(s)    

Growth rate 
Attrition rate 
Discount rate 
Royalty rate 
Discount rate 

3.0 % 
15.0 % 
21.0 % 
3.0 % 
21.0 % 

As further discussed in Note 4, “Acquisitions,” the Company acquired CSuite on November 1, 2022 and provisionally allocated the 
purchase  price to  the  assets  acquired  and  liabilities  assumed.  The  fair  values  of  intangible  assets  associated  with  the  acquisition  of 
CSuite were determined to be Level 3 under the fair value hierarchy. 

The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for 
these Level 3 measurements: 

Categories 
Customer relationships 

   Fair Value 
  $ 

Valuation Techniques 
2,500    Multi-period excess earnings 

Trade name 

  $ 

1,500    Relief from royalty 

Unobservable Inputs 

   Input Value(s)    

Growth rate 
Attrition rate 
Discount rate 
Royalty rate 
Discount rate 

3.0 % 
25.0 % 
16.5 % 
2.5 % 
15.5 % 

As  further  discussed  in Note  4,  “Acquisitions,” the  Company  acquired  SNS  on  November  18,  2022 and  provisionally allocated  the 
purchase price to the assets acquired and liabilities assumed. The fair values of intangible assets associated with the acquisition of SNS 
were determined to be Level 3 under the fair value hierarchy. 

The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for 
these Level 3 measurements: 

Categories 
Customer relationships 

   Fair Value 
  $ 

Valuation Techniques 
3,600    Multi-period excess earnings 

Trade name 

  $ 

3,100    Relief from royalty 

Unobservable Inputs 

   Input Value(s)    

Growth rate 
Attrition rate 
Discount rate 
Royalty rate 
Discount rate 

3.0 % 
10.0 % 
21.0 % 
3.0 % 
21.0 % 

100 

  
  
    
  
      
  
  
    
  
      
  
  
    
    
  
      
  
  
    
  
  
  
    
  
      
  
  
    
  
      
  
  
    
    
  
      
  
  
    
  
  
  
    
  
      
  
  
    
  
      
  
  
    
    
  
      
  
  
    
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

NOTE 24 RELATED PARTIES 

Related party transactions, including services provided to or received by the Company’s subsidiaries, are measured in part by the amount 
of  consideration  paid  or  received  as  established  and  agreed  by the  parties.  Except  where  disclosed  elsewhere  in  these  consolidated 
financial statements, the following is a summary of related party relationships and transactions. 

(a) 

Argo Management Group, LLC 

The Company acquired Argo Management in April 2016. Argo Management’s primary business is to act as Managing Member of Argo 
Holdings. At December 31, 2022 and December 31, 2021, each of the Company, John T. Fitzgerald (“Fitzgerald”), the Company’s Chief 
Executive Officer and President, and certain of Fitzgerald’s immediate family members owns equity interests in Argo Holdings, all of 
which interests were acquired prior to the Company’s acquisition of Argo Management. Subject to certain limitations, Argo Holdings’ 
governing documents require all individuals and entities owning an equity interest in Argo Holdings to fund upon request his/her/its pro 
rata  share  of  any  funding  requirements  of  Argo  Holdings  up  to  an  aggregate  maximum  amount  equal  to  his/her/its  total  capital 
commitment (each request for funds being referred to as a “Capital Call”). Argo Holdings made no Capital Calls during the years ended 
December 31, 2022 and December 31, 2021. 

(b) 

VA Lafayette 

On December 30 2021, the Company closed on an agreement to acquire 100% of the membership interests in VA Lafayette from a 
current holder of the Company’s Preferred Shares (refer to Note 4, “Acquisitions”, for further detail).  The Company determined the 
acquisition was an arms-length transaction based upon the purchase price paid compared to the pricing of similar third-party transactions. 

NOTE 25 COMMITMENTS AND CONTINGENT LIABILITIES 

(a) 

Legal proceedings: 

In May 2016, Aegis Security Insurance Company (“Aegis”) filed a complaint for breach of contract and declaratory relief against the 
Company in the Eastern District of Pennsylvania alleging, among other things, that the Company breached a contractual obligation to 
indemnify Aegis for certain customs bond losses incurred by Aegis under the indemnity and hold harmless agreements provided by the 
Company to Aegis for certain customs bonds reinsured by Lincoln General Insurance Company (“Lincoln General”) during the period 
of time that Lincoln General was a subsidiary of the Company.  Lincoln General was placed into liquidation in November 2015 and 
Aegis subsequently invoked its rights to indemnity under the indemnity and hold harmless agreements. Effective January 20, 2020, 
Aegis and the Company entered into a Settlement Agreement with respect to such litigation pursuant to which the Company agreed to 
pay Aegis a one-time settlement amount of $0.9 million, which the Company reported in its consolidated statement of operations during 
the first quarter of 2020, and to reimburse Aegis for 60% of future losses that Aegis may sustain in connection with such customs bonds, 
up to a maximum reimbursement amount of $4.8 million. During 2020, the Company made reimbursement payments to Aegis of $0.5 
million in connection with the Settlement Agreement.  During 2022 and 2021, the Company made reimbursement payments to Aegis 
of $0.4  million  and  $0.1 million,  respectively, in  connection  with  the  Settlement  Agreement,  which  is  included in  general  and 
administrative expenses in its consolidated statements of operations for the years ended December 31, 2022 and December 31, 2021, 
respectively.  The Company’s potential exposure under these agreements was not reasonably determinable at December 31, 2022, and 
no liability has been recorded in the in the consolidated financial statements at December 31, 2022. 

(b) 

Guarantees: 

Mendota 

As part of the October 18, 2018 transaction to sell Mendota, the Company will indemnify the buyer for any loss and loss adjustment 
expenses with respect to open claims in excess of Mendota’s carried unpaid loss and loss adjustment expenses at June 30, 2018 related 
to the open claims. The maximum obligation to the Company with respect to the open claims is $2.5 million. Per the purchase agreement, 
a security interest on the Company’s equity interest in its consolidated subsidiary, Net Lease, as well as any distributions to the Company 
from Net Lease, was to be collateral for the Company’s payment of obligations with respect to the open claims. 

During the third quarter of 2021, the purchasers of Mendota and the Company agreed to release the Company’s equity interest in Net 
Lease as collateral and allow Net Lease to make distributions to the Company.  In exchange, the Company agreed to deposit $2.0 million 
into an escrow account and advance $0.5 million to the purchaser of Mendota to satisfy the Company’s payment obligation with respect 
to the open claims. 

101 

  
  
  
  
  
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

During  the  third  quarter  of  2022,  the  buyer  provided  to  the  Company  an  analysis  of  the  claims  development  that  indicated  that 
the Company’s potential exposure with respect to the open claims was at the maximum obligation amount.  Previous communications 
from the buyer noted no such development and the buyer was not obligated to provide development information to the Company until 
the first quarter of 2023.  As a result of the newly provided information, the Company recorded a liability of $2.5 million during the 
third quarter of 2022, which is included in accrued expenses and other liabilities in the consolidated balance sheet at December 31, 2022 
and loss on disposal of discontinued operations in the consolidated statement of operations for the year ended December 31, 2022.  There 
were no payments made by the Company related to the open claims during the years ended December 31, 2022 and December 31, 
2021.  During the first quarter of 2023, the $2.0 million that had been previously deposited into an escrow account was released and 
remitted to the buyer to satisfy the Company’s payment with respect to the open claims.   

VA Lafayette 

The LA Mortgage is nonrecourse indebtedness with respect to the assets of VA Lafayette, and the LA Mortgage is not, nor will it be, 
guaranteed  by  Kingsway  or  its  affiliates  unless  VA  Lafayette  acts  in  bad-faith  or  commits  intentional  acts  with  respect  to  the  LA 
Mortgage.  The LA Mortgage is secured in part by a guaranty of recourse liabilities, whereby KAI, as guarantor, would become liable 
for the recourse liabilities if VA Lafayette, as borrower, violates certain terms of the loan agreement.  Under the guarantee, the lender 
can recover losses from the guarantor for certain bad-faith or other intentional acts of the borrower, such as rents retained by the borrower 
in violation of the loan documents, fraud or intentional misrepresentation, changes to the lease without the lender’s consent, willful 
misconduct, criminal acts and environmental losses sustained by lender.  In addition, the guarantee provides that the LA Mortgage will 
be the full personal recourse obligation of the guarantor, for certain actions, such as prohibited transfers of the collateral or bankruptcy 
of the borrower.  

(c) 

Collateral pledged and restricted cash: 

Short-term investments with an estimated fair value of $0.2 million at December 31, 2022 and December 31, 2021, were on deposit with 
state regulatory authorities. 

The Company also has restricted cash of $13.1 million and $17.3 million at December 31, 2022 and December 31, 2021, respectively. 
Included in restricted cash are: 

• 

• 

• 

$7.6 million and $12.6 million at December 31, 2022 and December 31, 2021, respectively, held as deposits by IWS, Geminus, 
PWI, PWSC (December 31, 2021 only), Ravix and CSuite; 

$1.9 million at December 31, 2022 and December 31, 2021, on deposit with state regulatory authorities; and 

$3.5 million and $2.8 million at December 31, 2022 and December 31, 2021, respectively, pledged to third-parties as deposits 
or to collateralize liabilities. Collateral pledging transactions are conducted under terms that are common and customary to 
standard collateral pledging and are subject to the Company’s standard risk management controls. 

NOTE 26 SUBSEQUENT EVENTS 

Exercise of TruPs Repurchase Options and Payment of Deferred Interest 

In February 2023, the Company entered into amendments to the repurchase agreements described in Note 11, “Derivatives,”, that would 
give the Company an additional discount on the total repurchase price if the Company effected a 100% repurchase on or before March 
15, 2023.  On March 2, 2023, the Company gave notice to the holders that it intends to exercise its options to repurchase 100% of the 
principal no later than March 15, 2023.  The total amount to be paid will be $56.5 million, which includes a credit for the $2.3 million 
that the Company previously paid at the time of entering into the repurchase agreements. As a result, the Company will have repurchased 
$75.5 million of principal and $21.2 million of deferred interest (valued as of December 31, 2022). The Company intends to use currently 
available funds from working capital to fund the repurchases. 

In order to execute the repurchase, the Company will have to pay an estimated $4.7 million of deferred interest to the remaining trust 
preferred debt instrument for which the Company did not have the right to repurchase. After the repurchase is completed, the Company 
will continue to have $15 million of principal outstanding related to remaining trust preferred debt instrument. 

102 

  
  
  
  
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 
Notes to Consolidated Financial Statements 

Notice of Redemption of Class A Preferred Stock 

On March 1, 2023, the Company notified holders of its Preferred Shares of its intention to redeem all the outstanding Class A Preferred 
Stock on March 15, 2023 (the “Anticipated Redemption Date”).  The Company anticipates redeeming all Class A Preferred Stock that 
remain outstanding on, and is not converted by, the Anticipated Redemption Date for the price of $25.00 per Preferred Share, plus 
accrued and unpaid dividends thereon, whether or not declared, up to and including the Anticipated Redemption Date. 

In the event 100% of the Preferred Shares are redeemed by the Company on the Anticipated Redemption Date, the Company estimates 
that the aggregate amount required to redeem will be approximately $6.1 million, which would be paid using cash on hand.  However, 
based on discussions with the holders of the Preferred Shares, the Company anticipates that 100% of the Preferred Shares would be 
converted and, in that case, there would be no cash outlay by the Company. 

Second Amendment to 2020 KWH Loan 

On  February  28,  2023,  KWH  entered  into  a  second  amendment  to  the  2020  KWH  Loan  (the  “KWH  DDTL”)  that  provides  for  an 
additional delayed draw term loan in the principal amount of up to $10 million, with a maturity date of December 1, 2025. All or any 
portion  of  the  KWH  DDTL,  subject  to  a  $2  million  minimum  draw  amount,  may  be  requested  at  any  time  through  February  27, 
2024.  The proceeds are evidenced by an intercompany loan and guarantee between KAI and KWH.  The principal amount shall be 
repaid in quarterly installments in an amount equal to 3.75% of the original amount of the drawn DDTL.  Proceeds from certain assets 
dispositions, as defined, may be required to be used to repay outstanding draws under the DDTL.  The KWH DDTL also increases the 
senior cash flow leverage ratio maximum permissible for certain periods. 

103 

 
KINGSWAY FINANCIAL SERVICES INC. 

Item 9. Changes in and Disagreements with Accountants on Accounting and Financial Disclosure 

None 

Item 9A. Controls and Procedures 

Evaluation of Disclosure Controls and Procedures 

The  Company’s  management,  with  the  participation  of  our  Chief  Executive  Officer  and  Chief  Financial  Officer,  has  conducted  an 
evaluation of the effectiveness of the Company’s disclosure controls and procedures (as defined in Rule 13a-15(e) and 15d-15(e) under 
the Securities Exchange Act of 1934, as amended (the “Exchange Act”) as of December 31, 2022. 

The Company’s disclosure controls and procedures are designed to ensure that information required to be disclosed in the reports the 
Company files under the Exchange Act is recorded, processed, summarized and reported within the time periods specified in the SEC’s 
rules and forms and that such information is accumulated and communicated to the Company’s management, including the Company’s 
Chief Executive Officer and Chief Financial Officer, to allow for timely decisions regarding required disclosures. In designing and 
evaluating our disclosure controls and procedures, the Company’s management recognizes that disclosure controls and procedures, no 
matter  how  well  conceived  and  operated,  can  provide  only  reasonable,  not  absolute,  assurance  that  the  objectives  of  the  disclosure 
controls and procedures are met.  Our disclosure controls and procedures have been designed to meet reasonable assurance standards.   In 
addition,  the  design  of  disclosure  controls  and  procedures  must  reflect  the  fact  that  there  are  resource  constraints  that  require  the 
Company’s management to apply its judgment in evaluating the benefits of possible controls and procedures relative to their costs. The 
design of any disclosure controls and procedures also is based in part upon certain assumptions about the likelihood of future events, 
and there can be no assurance that any design will succeed in achieving its stated goals under all potential future conditions. 

Based on this evaluation, the Company’s Chief Executive Officer and Chief Financial Officer have concluded that, as of December 31, 
2022, the Company’s disclosure controls and procedures are not effective as a result of one unremediated material weakness in the 
Company’s internal control over financial reporting that was discovered during the course of the 2018 external audit of the accounts, 
relating to the accounting for and disclosure of certain complex and nonrecurring transactions as it specifically pertains to the adoption 
and application of ASU 2014-09, Revenue from Contracts with Customers (“ASU 2014-09”).  Not all material weaknesses necessarily 
present the same risks from period to period as a result of differing events and transactions which have occurred or may occur in current 
and future periods.   

Management’s Report on Internal Control over Financial Reporting 

The Company’s management is responsible for establishing and maintaining adequate internal control over financial reporting as defined 
in Rules 13a-15(f) and 15d-15(f) under the Exchange Act. The Company’s management evaluated the effectiveness of its internal control 
over  financial  reporting  based  on  the  framework  in  Internal  Control-Integrated  Framework  issued  by  the  Committee  of  Sponsoring 
Organizations of the Treadway Commission (2013 framework). Based on that evaluation, the Company’s management has concluded 
that,  as  of  December  31,  2022,  our  internal  controls  over  financial  reporting  are  not  effective  because  of  the  existence  of  one 
unremediated material weakness in internal control over financial reporting, that was discovered during the course of the 2018 external 
audit of the accounts, relating to the accounting for and disclosure of certain complex and nonrecurring transactions as it specifically 
pertains to the adoption and application of ASU 2014-09. 

Material Weaknesses in Internal Control over Financial Reporting 

A material weakness is defined as a deficiency or combination of deficiencies in internal control over financial reporting such that there 
is a reasonable possibility that a material misstatement of annual or interim consolidated financial statements will not be prevented or 
detected on a timely basis. 

With  respect  to  the  inadequate  design  accounting  for  and  operation  of  internal  disclosure  of  certain  complex  and  nonrecurring 
transactions, the execution of the controls over the application of accounting literature did not operate effectively with respect to the 
adoption and application of ASU 2014-09.  This matter was discovered during the course of the 2018 external audit of the accounts and 
was reviewed with the Company’s Audit Committee. 

As  a  result  of  this  material  weakness,  the  Company’s  management  directed  a  comprehensive  review  of  its  consolidated  financial 
statements  to assess  the possibility  of  further  material  misstatements  that  may  remain  unidentified. As  a  result  of such  review,  and 
notwithstanding the material weakness described above, the Company’s management, including the Company’s Chief Executive Officer 
and Chief Financial Officer, believes that the audited consolidated financial statements contained in this 2022 Annual Report on Form 
10-K fairly present, in all material respects, our financial condition, results of operations and cash flows for the fiscal years presented in 
conformity with U.S. GAAP. 

104 

KINGSWAY FINANCIAL SERVICES INC. 

Remediation Process 

In 2022, the Company directed its internal audit department to conduct a thorough review of the material revenue processes.  The review 
is in its final stages, which has preliminarily indicated no material issues.  The Company expects to use the final results of this review 
in early 2023 to implement a remediation plan for this final material weakness. 

The actions that the Company is taking are subject to ongoing senior management review as well as Audit Committee oversight. The 
Company is committed to maintaining a strong internal control environment and believes that these remediation efforts will represent 
significant improvements in its controls. 

Changes in Internal Control over Financial Reporting 

On  November  1,  2022,  the  Company  acquired  100%  of  the  outstanding  equity  interests of  CSuite and  on  November  18,  2022,  the 
Company acquired substantially all of the assets and assumed certain specified liabilities of SNS.  Since the dates of these acquisitions, 
the Company has been analyzing and evaluating procedures and controls to determine their effectiveness and to make them consistent 
with our disclosure  controls and  procedures.  As permitted by  the SEC,  CSuite  and  SNS have been excluded  from  the  scope of our 
quarterly discussion of material changes in internal control over financial reporting below. 

There have been no changes in the Company’s internal control over financial reporting during the period beginning October 1, 2022, 
and  ending  December  31,  2022,  that  have  materially  affected,  or are  reasonably  likely  to  materially  affect,  the  Company’s  internal 
control over financial reporting, except with respect to CSuite and SNS. 

Item 9B. Other Information 

None 

Item 9C. Disclosure Regarding Foreign Jurisdictions that Prevent Inspections 

Not Applicable 

105 

 
 
KINGSWAY FINANCIAL SERVICES INC. 

PART III.  

Item 10. Directors, Executive Officers, and Corporate Governance 

The  information  required  by  this  Item  is  incorporated  herein  by  reference  to  the  Proxy  Statement  for  our 2022  Annual  Meeting  of 
Shareholders, which will be filed with the SEC no later than 120 days after the end of our fiscal year ended December 31, 2022. 

We have adopted a Code of Business Conduct and Ethics that is applicable to all employees, including our chief executive officer, chief 
financial officer and other senior financial personnel, as well as our directors. A copy of the Code of Business Conduct and Ethics is 
posted in the “Corporate Governance” section of our website at www.kingsway-financial.com. Any future amendments to the Code of 
Business Conduct and Ethics and any grant of waiver from a provision of the code requiring disclosure under applicable SEC rules will 
be disclosed in the “Corporate Governance” section of our website. 

Item 11. Executive Compensation 

The  information  required  by  this  Item  is  incorporated  herein  by  reference  to  the  Proxy  Statement  for  our 2022  Annual  Meeting  of 
Shareholders, which will be filed with the SEC no later than 120 days after the end of our fiscal year ended December 31, 2022. 

Item 12. Security Ownership of Certain Beneficial Owners and Management and Related Stockholder Matters 

The  information  required  by  this  Item  is  incorporated  herein  by  reference  to  the  Proxy  Statement  for  our 2022  Annual  Meeting  of 
Shareholders, which will be filed with the SEC no later than 120 days after the end of our fiscal year ended December 31, 2022. 

Item 13. Certain Relationships and Related Transactions, and Director Independence 

The  information  required  by  this  Item  is  incorporated  herein  by  reference  to  the  Proxy  Statement  for  our 2022  Annual  Meeting  of 
Shareholders, which will be filed with the SEC no later than 120 days after the end of our fiscal year ended December 31, 2022. 

Item 14. Principal Accounting Fees and Services  

The  information  required  by  this  Item  is  incorporated  herein  by  reference  to  the  Proxy  Statement  for  our 2022  Annual  Meeting  of 
Shareholders, which will be filed with the SEC no later than 120 days after the end of our fiscal year ended December 31, 2022. 

106 

 
 
KINGSWAY FINANCIAL SERVICES INC. 

Part IV 

Item 15. Exhibits, Financial Statement Schedules 

(a) Documents filed as part of this Report  

(1) Financial Statements. We have filed the following documents, which are included in Part II, Item 8 of this 2022 Annual 
Report on Form 10-K.   

Report of Independent Registered Public Accounting Firm 

Consolidated Balance Sheets 

Consolidated Statements of Operations 

Consolidated Statements of Comprehensive Loss 

Consolidated Statements of Shareholders’ Equity 

Consolidated Statements of Cash Flow 

Notes to Consolidated Financial Statements 

(2) Financial Statement Schedules. The following financial statement schedules are filed as a part hereof along with the related 
reports of the Independent Registered Public Accounting Firm included in Part II, Item 8. Schedules not listed here have been 
omitted because they are not applicable or the required information is included in the Consolidated Financial Statements. 

Schedule I         Condensed Financial Information of the Registrant (Parent Company) 

(3) Exhibits. The exhibits listed in the accompanying “Index to Exhibits” that follow the signature pages of this report are filed 
or incorporated by reference as part of this Form 10-K. 

(b) Exhibits. Included in Item 15(a)(3) above 

(c) Financial Statement Schedules. Included in Item 15(a)(2) above 

107 

 
 
KINGSWAY FINANCIAL SERVICES INC. 

SCHEDULE I. Condensed Financial Information of the Registrant (Parent Company) 

Parent Company Balance Sheets  

(in thousands) 

Assets 
Investments in subsidiaries 
Cash and cash equivalents 
Other assets 
Total Assets 
Liabilities and Shareholders’ Equity 
Liabilities: 
Accrued expenses and other liabilities 
Total Liabilities 
Redeemable Class A preferred stock 
Shareholders’ Equity: 
Common stock 
Additional paid-in capital 
Treasury stock, at cost 
Accumulated deficit 
Accumulated other comprehensive income 
Shareholders’ equity attributable to common shareholders 
Total Liabilities, Class A preferred stock and Shareholders’ Equity 

See accompanying report of independent registered accounting firm. 

December 31, 

2022     

December 31, 
2021   

  $ 

  $ 

  $ 

  $ 

23,545     $ 
32       
1,313       
24,890     $ 

3,206     $ 
3,206       
6,013       

—       
359,985       
(492 )     
(370,427 )     
26,605       
15,671       
24,890     $ 

1,944   
56   
447   
2,447   

1,674   
1,674   
6,497   

—   
359,138   
(492 ) 
(395,149 ) 
30,779   
(5,724 ) 
2,447   

108 

  
  
  
      
        
  
      
        
  
    
    
      
        
  
      
        
  
    
    
      
        
  
    
    
    
    
    
    
  
 
 
KINGSWAY FINANCIAL SERVICES INC. 

SCHEDULE I. Condensed Financial Information of the Registrant (Parent Company) 

Parent Company Statements of Operations 

(in thousands) 

Other revenue (expenses), net: 

General and administrative expenses 
Non-operating other expense 

Total other expenses, net 
Loss from continuing operations before income tax benefit and equity in income 
of subsidiaries 
Income tax benefit 
Equity in income of subsidiaries 
Net income 

See accompanying report of independent registered accounting firm. 

Years ended December 31,   
2021   

2022     

  $ 

  $ 

(2,081 )   $ 
(8 )     
(2,089 )     

(2,089 )     
(314 )     
16,840       
15,065     $ 

(3,287 ) 
(2 ) 
(3,289 ) 

(3,289 ) 
(340 ) 
4,809   
1,860   

109 

  
  
  
  
      
        
  
    
    
    
    
    
  
 
 
KINGSWAY FINANCIAL SERVICES INC. 

SCHEDULE I. Condensed Financial Information of the Registrant (Parent Company) 

Parent Company Statements of Comprehensive Loss  

Years ended December 31,   
2021   

2022     

  $ 

15,065     $ 

1,860   

—       
—       
—       
(4,238 )     
(4,238 )     
10,827     $ 

—   
—   
—   
(7,295 ) 
(7,295 ) 
(5,435 ) 

(in thousands) 

Net income 
Other comprehensive loss, net of taxes(1): 
Unrealized losses on available-for-sale investments: 

Unrealized losses arising during the period 
Reclassification adjustment for amounts included in net loss 

Other comprehensive loss - parent only 
Equity in other comprehensive loss of subsidiaries 
Other comprehensive loss 
Comprehensive income (loss) 
(1) Net of income tax expense (benefit) of $0 and $0 in 2022 and 2021, respectively 

  $ 

See accompanying report of independent registered accounting firm. 

110 

  
  
  
  
  
      
        
  
      
        
  
      
        
  
    
    
    
    
    
 
 
KINGSWAY FINANCIAL SERVICES INC. 

SCHEDULE I. Condensed Financial Information of the Registrant (Parent Company) 

Parent Company Statements of Cash Flows  

(in thousands) 

Cash provided by (used in): 
Operating activities: 
Net income 
Adjustments to reconcile net income to net cash used in operating activities: 

Equity in net income of subsidiaries 
Stock-based compensation expense, net of forfeitures 
Other, net 

Net cash used in operating activities 
Investing activities: 
Net cash from investing activities 
Financing activities: 
Proceeds from exercise of warrants 
Capital contribution to subsidiary 
Net cash provided by financing activities 
Net decrease in cash and cash equivalents 
Cash and cash equivalents at beginning of period 
Cash and cash equivalents at end of period 

See accompanying report of independent registered accounting firm. 

Years ended December 31,   
2021   

2022     

  $ 

15,065     $ 

1,860   

(16,840 )     
589       
667       
(519 )     

(4,809 ) 
1,620   
(551 ) 
(1,880 ) 

—       

—   

545       
(50 )     
495       
(24 )     
56       
32     $ 

1,750   
—   
1,750   
(130 ) 
186   
56   

  $ 

111 

  
  
  
  
      
        
  
      
        
  
      
        
  
    
    
    
    
      
        
  
    
      
        
  
    
    
    
    
    
  
 
 
KINGSWAY FINANCIAL SERVICES INC. 

Item 16.          Form 10-K Summary 

None. 

Exhibit  Description 

EXHIBIT INDEX 

2.1 

2.2 

2.3 

3.1 

3.2 

4.1 

4.2 

4.3 

4.4 

4.5 

4.6 

4.7 

4.8 

4.9 

Stock  Purchase  Agreement  By  and  Among  Premier  Holdings,  LLC,  Advantage  Auto  MGA,  LLC,  Mendota  Insurance 
Company, Kingsway America Inc. and Kingsway Financial Services Inc., Dated as of July 16, 2018 (included as Exhibit 
2.1 to the Form 8-K, filed July 20, 2018, and incorporated herein by reference). 

Stock Purchase Agreement, dated as of October 12, 2020, by and among Kingsway Warranty Holdings LLC,Kingsway 
America  Inc.,  PWI  Holdings,  Inc.,  and  ADESA  Dealer  Services,  LLC (included  as  Exhibit  2.1  to  Form  8-K,  filed 
October 13, 2020, and incorporated herein by reference). 

Stock Purchase Agreement, dated July 29, 2022, by and among Professional Warranty Service Corporation, a Virginia 
corporation  (the  “Company”)  Tyler  Gordy,  an  individual  (“Gordy”);  Professional  Warranty  Services  LLC,  a  Delaware 
limited liability company (“Parent” and together with Gordy, each a “Seller” and collectively “Sellers”); and PCF Insurance 
Services of the West, LLC, a Delaware limited liability company (“Buyer”) (included as Exhibit 2.1 to the Form 10-Q, 
filed August 4, 2022, and incorporated herein by reference). 

Certificate of Incorporation of Kingsway Financial Services Inc. (included as Exhibit 3.1 to the Form 8-K, filed December 
31, 2018, and incorporated herein by reference). 

By-laws  of Kingsway  Financial  Services Inc. (included  as  Exhibit  3.2  to  the Form  8-K,  filed December  31, 2018,  and 
incorporated herein by reference). 

Indenture  dated  December  4,  2002  between  Kingsway  America  Inc.  and  State  Street  Bank  and  Trust  Company  of 
Connecticut, National Association (included as Exhibit 4.3 to the Form 10-K, filed March 30, 2012, and incorporated herein 
by reference). 

Indenture dated May 15, 2003 between Kingsway America Inc. and U.S. Bank National Association (included as Exhibit 
4.4 to the Form 10-K, filed March 30, 2012, and incorporated herein by reference). 

Indenture  dated  October  29,  2003  between  Kingsway  America  Inc.  and  U.S.  Bank  National  Association (included  as 
Exhibit 4.5 to the Form 10-K, filed March 30, 2012, and incorporated herein by reference). 

Indenture dated May 22, 2003 between Kingsway America Inc., Kingsway Financial Services Inc., and Wilmington Trust 
Company (included as Exhibit 4.6 to the Form 10-K, filed March 30, 2012, and incorporated herein by reference). 

Junior  Subordinated  Indenture  dated  September  30,  2003  between  Kingsway  America  Inc.  and  J.P  Morgan  Chase 
Bank (included as Exhibit 4.7 to the Form 10-K, filed March 30, 2012, and incorporated herein by reference). 

Indenture dated December 16, 2003 between Kingsway America Inc., Kingsway Financial Services Inc., and Wilmington 
Trust Company (included as Exhibit 4.8 to the Form 10-K, filed March 30, 2012, and incorporated herein by reference). 

Amended and Restated Common Stock Series B Warrant Agreement, dated July 8, 2014 (included as Exhibit 4.1 to the 
Form 8-K, filed July 10, 2014, and incorporated herein by reference). 

Form of Stock Certificate (included as Exhibit 4.1 to the Form 8-K, filed December 31, 2018, and incorporated herein by 
reference). 

Second Amended and Restated Kingsway Financial Services Inc. Common Stock Series B Warrant Agreement  (included 
as Exhibit 4.7 to the Form 10-Q, filed August 5, 2021, and incorporated herein by reference). 

10.1 

Kingsway Financial Services Inc. 2013 Equity Incentive Plan (included as Schedule B to the Definitive Proxy Statement 
on Schedule 14A filed with the SEC on April 11, 2013, and incorporated herein by reference). * 

112 

  
 
 
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
 
 
  
  
 
  
KINGSWAY FINANCIAL SERVICES INC. 

Exhibit  Description 

10.2 

10.3 

10.4 

10.5 

10.6 

10.7 

10.8 

10.9 

Form of Subscription Agreement (included as Exhibit 10.1 to the Form 8-K, filed December 27, 2013, and incorporated 
herein by reference). 

Registration  Rights  Agreement,  dated  February  3,  2014,  by  and  among  the  Company  and  the  other  parties  signatory 
thereto (included as Exhibit 10.2 to the Form 8-K, filed February 4, 2014, and incorporated herein by reference). 

Kingsway  America  Inc.  Employee  Share  Purchase  Plan (included  as  Schedule  B  to  the  Definitive  Proxy  Statement  on 
Schedule 14A filed with the SEC on April 30, 2014 and incorporated herein by reference). * 

Registration Rights Agreement, dated as of November 16, 2016 by and among the Company, GrizzlyRock Institutional 
Value Partners, LP and W.H.I. Growth Fund Q.P., L.P. (included as Exhibit 10.4 to Form 8-K, filed November 16, 2016, 
and incorporated herein by reference). 

Registration  Rights  Agreement,  dated  as  of  November  16,  2016  by  and  between  the  Company  and  Yorkmont  Capital 
Partners, LP. (included as Exhibit 10.5 to Form 8-K, filed November 16, 2016, and incorporated herein by reference). 

Right of First Offer Agreement, dated as of November 16, 2016 by and between the Company and GrizzlyRock Institutional 
Value Partners, LP. (included as Exhibit 10.6 to Form 8-K, filed November 16, 2016, and incorporated herein by reference). 

Right of First Offer Agreement, dated as of November 16, 2016 by and between the Company and W.H.I. Growth Fund 
Q.P., L.P. (included as Exhibit 10.7 to Form 8-K, filed November 16, 2016, and incorporated herein by reference). 

Amendment No. 1 to the Kingsway Financial Services Inc. 2013 Equity Incentive Plan (included as Exhibit 10.1 to Form 
10-Q, filed August 8, 2018, and incorporated herein by reference). 

10.10  Offer Letter, dated September 5, 2018, between the Company and John T. Fitzgerald (included as Exhibit 10.2 to Form 8-

K, filed September 10, 2018, and incorporated herein by reference). 

10.11 

Severance Agreement, dated September 5, 2018, between the Company and John T. Fitzgerald (included as Exhibit 10.3 
to Form 8-K, filed September 10, 2018, and incorporated herein by reference). 

10.12  Restricted Stock Agreement, dated September 5, 2018, between the Company and John T. Fitzgerald (included as Exhibit 

10.4 to Form 8-K, filed September 10, 2018, and incorporated herein by reference). 

10.13  Form of Indemnification Agreement for Directors and Officers (included as Exhibit 10.5 to Form 8-K, filed September 10, 

2018, and incorporated herein by reference). 

10.14  Employment  Offer  Letter,  dated  as  of  October  23,  2019,  by  and  between  Kent  A.  Hansen  and  Kingsway  America 

Inc.(included as Exhibit 10.2 to Form 8-K, filed February 28, 2020, and incorporated herein by reference). 

10.15  Kingsway Financial Services Inc. 2020 Equity Incentive Plan (included as Schedule A to the Definitive Proxy Statement on 

Schedule 14A filed with the SEC on August 20, 2020, and incorporated herein by reference). * 

10.16  Loan and Security Agreement, dated as of December 1, 2020, among Kingsway Warranty Holdings LLC, Trinity Warranty 
Solutions LLC, Geminus Holding Company, Inc., IWS Acquisition Corporation and PWI Holdings, Inc., as Borrowers, the 
other Loan Parties party thereto, and CIBC Bank USA, as Lender and as Issuing Lender (included as Exhibit 10.1 to Form 
8-K, filed December 2, 2020, and incorporated herein by reference). 

10.17  Letter Agreement, effective as of December 31, 2020, by and among Kingsway Warranty Holdings LLC, Trinity Warranty 
Solutions LLC, Geminus Holding Company, Inc., IWS Acquisition Corporation, and PWI Holdings, Inc., as Borrowers, the 
other Loan Parties party thereto, and CIBC Bank USA, as Lender. 

10.18  Form of Restricted Stock Agreement. * 

113 

 
 
  
  
  
  
  
  
  
  
 
 
  
  
  
  
  
  
  
  
 
 
  
  
  
  
  
  
  
  
  
  
  
  
KINGSWAY FINANCIAL SERVICES INC. 

Exhibit  Description 

10.19  Employment Separation Agreement and Release, by and between Kingsway America, Inc. and Paul R. Hogan, dated as of 
March 31, 2021 (included as Exhibit 10.1 to Form 8-K, filed April 2, 2021, and incorporated herein by reference). 

10.20  Stock  Purchase  Agreement  by  and  among,  Ravix  Acquisition,  LLC,  The  Shareholders  of  Ravix  Financial,  Inc.,  Ravix 
Financial, Inc., Kingsway America, Inc. (solely with respect to Section 9.21), and Dan Saccani, as the Seller Representative, 
dated October 1, 2021 (included as Exhibit 10.1 to Form 8-K, filed October 4, 2021, and incorporated herein by reference). 

10.21  Membership Interest Purchase Agreement by and among CSuite Acquisition, LLC, Arthur J. Cohen and Beth Garden, as 
Trustees of the Cohen Garden Trust dated July 13, 2015, Realized Potential, LLC, and Arthur J. Cohen, as the Sellers’ 
Representative,  dated  November  1,  2022  (included  as  Exhibit  10.1  to  the  Form  8-K,  filed  November  2,  2022,  and 
incorporated herein by reference). 

10.22  Asset purchase agreement by and among Pegasus acquirer LLC, as buyer, Secure Nursing Service, Inc., as seller and Rafael 
Gofman, Ella Gofman And Zhanna Weiss, as the shareholders (included as Exhibit 10.1 to the Form 8-K, filed November 
21, 2022, and incorporated herein by reference). 

10.23  Purchase and Sale Agreement dated December 22, 2022, by and between TRT Leaseco, LLC, as Seller, and BNSF Dayton 
LLC,  as  Purchaser  (included  as  Exhibit  10.1  to  the  Form  8-K,  filed  December  23,  2022,  and  incorporated  herein  by 
reference). 

10.24  Second Amendment to Loan and Security Agreement, dated as of February 28, 2023, among Kingsway Warranty Holdings 
LLC, Trinity Warranty Solutions LLC, Geminus Holding Company, Inc., IWS Acquisition Corporation and PWI Holdings, 
Inc., as Borrowers, the other Loan Parties party thereto, and CIBC Bank USA, as Lender and as Issuing Lender. 

14 

21 

23 

Kingsway Financial Services Inc. Code of Business Conduct & Ethics Inc. Code of Business Conduct & Ethics (included 
as Exhibit 14 to form 10-K, Filed March 16, 2018, and incorporated herein by reference. 

Subsidiaries of Kingsway Financial Services Inc. 

Consent of Plante & Moran, PLLC 

31.1  Certification of Chief Executive Officer pursuant to Rule 13a-14(a) of the Exchange Act 

31.2  Certification of Chief Financial Officer pursuant to Rule 13a-14(a) of the Exchange Act 

32.1  Certification of Chief Executive Officer pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the 

Sarbanes-Oxley Act of 2002 

32.2  Certification  of  Chief  Financial  Officer  pursuant  to  18  U.S.C.  Section  1350,  as  adopted  pursuant  to  Section  906  of  the 

Sarbanes-Oxley Act of 2002 

101.INS  Inline XBRL Instance Document 

101.SCH  Inline XBRL Taxonomy Extension Schema 

101.CAL  Inline XBRL Taxonomy Extension Calculation Linkbase 

101.DEF  Inline XBRL Taxonomy Extension Definition Linkbase 

101.LAB  Inline XBRL Taxonomy Extension Label Linkbase 

101.PRE  Inline XBRL Taxonomy Extension Presentation Linkbase 

104 

Cover Page Interactive Data File (embedded within the Inline XBRL Document and include in Exhibit 101) 

* Management contract or compensatory plan or arrangement. 

114 

  
  
  
  
 
 
  
  
  
  
  
  
  
  
 
 
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
  
 
KINGSWAY FINANCIAL SERVICES INC. 

SIGNATURES 

Pursuant to the requirements of Section 13 or 15(d) of the Securities Exchange Act of 1934, the registrant has duly caused this report to 
be signed on its behalf by the undersigned, thereunto duly authorized. 

Date:  March 8, 2023 

KINGSWAY FINANCIAL SERVICES INC. 

/s/ John T. Fitzgerald 

By: 
Name:  John T. Fitzgerald 
Title:  Chief Executive Officer, President and Director 

(Principal Executive Officer) 

Pursuant to the requirements of the Securities Exchange Act of 1934, this report has been signed below by the following persons on 
behalf of the registrant and in the capacities and on the dates indicated. 

/s/ John T. Fitzgerald 
John T. Fitzgerald 

/s/ Kent A. Hansen 
Kent A. Hansen 

/s/ Terence Kavanagh 
Terence Kavanagh 

/s/ Charles Frischer 
Charles Frischer 

/s/ Gregory Hannon 
Gregory Hannon 

/s/ Doug Levine 
Doug Levine 

/s/ Corissa Porcelli 
Corissa Porcelli 

/s/ Joseph Stilwell 
Joseph Stilwell 

Chief Executive Officer, President and Director 

March 8, 2023 

Chief Financial Officer and Executive Vice President 
(principal financial officer and principal accounting officer) 

March 8, 2023 

Chairman of the Board and Director 

March 8, 2023 

March 8, 2023 

March 8, 2023 

March 8, 2023 

March 8, 2023 

March 8, 2023 

Director 

Director 

Director 

Director 

Director 

115