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

Kingsway Financial Services Inc

kfs · NYSE Consumer Cyclical
Claim this profile
Ticker kfs
Exchange NYSE
Sector Consumer Cyclical
Industry Auto - Dealerships
Employees 201-500
← All annual reports
FY2018 Annual Report · Kingsway Financial Services Inc
Sign in to download
Loading PDF…
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, 2018 
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)

150 E. Pierce Road
Itasca, IL 
(Address of principal executive offices)

98-0475673

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

60143
(Zip Code)

1-416-848-1171

(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

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 and posted on its corporate Web site, if any, every Interactive Data 
File required to be submitted and posted pursuant to Rule 405 of Regulation S-T during the preceding 12 months (or for such shorter period that 
     No   
the registrant was required to submit and post such files).    Yes   

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

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

Large accelerated filer 

Accelerated filer 

Non-accelerated filer 
(Do not check if a 
smaller reporting 
company)

Smaller Reporting Company

Emerging Growth Company 

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

Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Exchange Act).    Yes   

     No   

 
 
 
 
 
 
As of June 30, 2018, the aggregate market value of the registrant's voting common stock held by non-affiliates of registrant was $37,291,317 
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 of the Registrant's Common Stock outstanding as of February 27, 2020 was 22,843,909.

 
KINGSWAY FINANCIAL SERVICES INC.

Caution Regarding Forward-Looking Statements

Table Of Contents

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. Selected Financial Data

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

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 Accounting Fees and Services

PART IV

Item 15. Exhibits, Financial Statement Schedules

Item 16. Form 10-K Summary

SIGNATURES

EXHIBIT INDEX

3

4

4

10

18

19

19

19

19

19

22

23

45

47

121

121

124

124

124

128

132

134

134

136

136

142

143

144

2

KINGSWAY FINANCIAL SERVICES INC.

Caution Regarding Forward-Looking Statements

This 2018 Annual Report on Form 10-K (the "2018 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 facts and circumstances affecting assumptions used in determining its provision for unpaid loss and loss adjustment 
expenses;
changes in facts and circumstances affecting assumptions used in evaluating its legal proceedings;
changes in industry trends and significant industry developments;
the impact of certain guarantees and indemnifications made by the Company;
its ability to complete and integrate current or future acquisitions successfully; and
its ability to implement its restructuring activities and execute its strategic initiatives successfully.

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 "Critical Accounting Estimates and Assumptions" in MD&A in this 2018 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 2018 Annual Report.

3

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 "Domestication").  The Company discontinued its existence as a corporation under Section 181 of the Ontario 
Business Corporations Act and, pursuant to Section 388 of the General Corporation Law of the State of Delaware (the "DGCL"), 
continued its existence under the DGCL as a corporation incorporated in the State of Delaware.  The Company's registered office 
is located at 150 E. Pierce Road, Itasca, Illinois 60143.

In connection with the Domestication, the outstanding common stock and preferred stock of the Company have been converted, 
on a one-for-one basis, into shares of common stock and preferred stock of the Company, respectively, as a corporation incorporated 
in the State of Delaware.  Prior to the Domestication, the common shares of Kingsway were listed on the Toronto Stock Exchange 
("TSX") and the New York Stock Exchange ("NYSE").  In connection with the Domestication, the Company delisted from the 
TSX.  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, asset management and real estate industries.  Kingsway conducts its business through the 
following  two reportable segments:  Extended Warranty  and Leased  Real Estate.    Extended Warranty and  Leased Real  Estate 
conduct their business and distribute their products in the United States.

Prior to the second quarter of 2018, the Company conducted its business through a third reportable segment, Insurance Underwriting.  
Insurance Underwriting included the following subsidiaries of the Company: Mendota Insurance Company, Mendakota Insurance 
Company,  Mendakota  Casualty  Company,  Kingsway  Amigo  Insurance  Company  ("Amigo")  and  Kingsway  Reinsurance 
Corporation ("Kingsway Re").  Mendota Insurance Company, Mendakota Insurance Company and Mendakota Casualty Company 
are referred to collectively herein as "Mendota."  On July 16, 2018, the Company announced that it had entered into a definitive 
agreement to sell Mendota.  On October 18, 2018, the Company announced that the sale was completed.  As a result, Mendota 
has been classified as discontinued operations and the results of their operations are reported separately for all periods presented.  
As a consequence of classifying Mendota as discontinued operations, the remaining composition of the Insurance Underwriting 
segment no longer meets the criteria of a reportable segment.  As such, all segmented information has been restated to exclude the 
Insurance Underwriting segment for all periods presented.  The operating results of Amigo and Kingsway Re, each of which are 
currently in voluntary run-off and were previously included in the Insurance Underwriting segment, are now included in Other 
income and expenses not allocated to segments, net.

Financial information about Kingsway's reportable business segments for the years ended December 31, 2018 and December 31, 
2017 is contained in the following sections of this 2018 Annual Report: (i) Note 28, "Segmented Information," to the Consolidated 
Financial Statements; and (ii) "Results of Continuing Operations" section of MD&A.

RESTATEMENT OF PREVIOUSLY ISSUED FINANCIAL STATEMENTS

The Company has restated its previously reported consolidated financial statements as of and for the year ended December 31, 
2017.  The restatements reflect corrections of errors identified in connection with the preparation of the consolidated financial 
statements for the year ended December 31, 2018, and relate primarily to i) the reclassification of certain investments acquired 
from Mendota on October 18, 2018 from assets held for sale to equity investments, limited liability investments, limited liability 
investments, at fair value and other investments in the consolidated balance sheet; and the reclassification of investment income, 
related to these investments, from loss from discontinued operations, net of taxes to net investment income in the consolidated 
statement of operations; ii) the consolidation of certain limited liability investments that had previously been accounted for under 
the equity method of accounting; and iii) the reclassification of cash and cash equivalents to restricted cash in the consolidated 
balance sheets.  The restatements are more fully discussed in Note 3, "Restatement of Previously Issued Financial Statements," to 
the Consolidated Financial Statements.  All amounts in this 2018 Annual Report affected by the restatements reflect such amounts 
as restated.

REPORTING CURRENCY

The Consolidated Financial Statements have been presented in U.S. dollars because the Company's principal investments and cash 
flows are denominated in U.S. dollars.  The Company's functional currency is the U.S. dollar since the substantial majority of its 

4

KINGSWAY FINANCIAL SERVICES INC.

operations is conducted in the United States.  Assets and liabilities of subsidiaries with non-U.S. dollar functional currencies are 
translated to U.S. dollars at period-end exchange rates, while revenue and expenses are translated at average monthly rates and 
shareholders' equity is translated at the rates in effect at dates of capital transactions.  Foreign currency translation adjustments are 
included in shareholders' equity under the caption accumulated other comprehensive loss.  Foreign currency gains and losses 
resulting from transactions that are denominated in currencies other than the entity's functional currency are reflected in non-
operating other income in the consolidated statements of operations. 

All of the dollar amounts in this 2018 Annual Report are expressed in U.S. dollars, except where otherwise indicated.  References 
to "dollars" or "$" are to U.S. dollars, and any references to "C$" are to Canadian dollars. 

GENERAL DEVELOPMENT OF BUSINESS

Sale of Mendota:

As described above, on July 16, 2018, the Company announced it had entered into a definitive agreement to sell Mendota.  On 
October 18, 2018, the Company completed the previously announced sale of Mendota.  The final aggregate purchase price of 
$28.6 million was redeployed primarily to acquire equity investments, limited liability investments, limited liability investments, 
at fair value and other investments, which were owned by Mendota at the time of the closing, and to fund $5.0 million into an 
escrow  account  to  be  used  to  satisfy  potential  indemnity  obligations  under  the  definitive  stock  purchase  agreement.    Further 
information is contained in Note 6, "Disposal, Discontinued Operations and Liquidation," to the Consolidated Financial Statements.  

Acquisition of Geminus:

On March 1, 2019, the Company completed the acquisition of Geminus Holding Company, Inc. ("Geminus"), a specialty, full-
service provider of vehicle service contracts ("VSCs") and other finance and insurance ("F&I") products to used car buyers around 
the country, for a purchase price of $8.4 million, comprised of cash paid at closing of $7.7 million and a seller note of $0.8 million.  
Geminus, headquartered in Wilkes-Barre, Pennsylvania, has been creating, marketing and administering VSCs and F&I products 
on high-mileage used cars through its subsidiaries, The Penn Warranty Corporation ("Penn") and Prime Auto Care, Inc. ("Prime"), 
since  1988.   Penn  and  Prime  distribute  these  products  via  independent  used  car  dealerships  and  franchised  car  dealerships, 
respectively.  Geminus recorded unaudited income before income tax expense of $1.4 million for the year ended December 31, 
2018.

Related to the acquisition of Geminus, the Company formed Kingsway Warranty Holdings LLC ("KWH") as its acquisition vehicle 
and contributed IWS Acquisition Corporation ("IWS") and Trinity Warranty Solutions LLC ("Trinity") to KWH.  The Company 
secured $10.0 million of acquisition financing from a third-party lender, with Geminus, IWS and Trinity listed as borrowers.  After 
accounting for the cash purchase price paid at closing and transaction-related expenses paid in cash at closing, $1.3 million of the 
$10.0 million of acquisition financing was made available to the Company to be used for general corporate purposes.

EXTENDED WARRANTY SEGMENT

Extended  Warranty  includes  the  following  subsidiaries  of  the  Company:  IWS,  Trinity  and  Professional  Warranty  Service 
Corporation  ("PWSC"), (collectively, "Extended Warranty"). 

IWS is a licensed motor vehicle service agreement company and is a provider of after-market vehicle protection services distributed 
by credit unions in 23 states and the District of Columbia to their members.

5

KINGSWAY FINANCIAL SERVICES INC.

Trinity  sells  heating,  ventilation,  air  conditioning  ("HVAC"),  standby  generator,  commercial  LED  lighting  and  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 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.

PWSC sells new 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.

Extended Warranty Products

IWS markets and administers vehicle service agreements and related products for new and used automobiles throughout the United 
States.  A vehicle service agreement is an agreement between IWS and the vehicle purchaser under which IWS agrees to replace 
or repair, for a specific term, designated vehicle parts in the event of a mechanical breakdown.  IWS serves as the administrator 
on all contracts it originates.  Vehicle service agreements supplement, or are in lieu of, manufacturers' warranties and provide a 
variety of extended coverage options.  Vehicle service agreements range from three months to seven years and/or 3,000 miles to 
100,000 miles.  The average term of a vehicle service agreement is between four and five years.  The cost of the vehicle service 
agreement is a function of the contract term, coverage limits and type of vehicle.

In addition to marketing vehicle service agreements, IWS also brokers a guaranteed asset protection product ("GAP") through its 
distribution channel.  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 earns a commission when a consumer purchases a GAP certificate but does not 
take on any insurance risk.  

Trinity sells HVAC, standby generator, commercial LED lighting and 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 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.

PWSC administers the insured warranty programs of liability coverage for new home construction companies, and the warranty 
is issued to new home buyers.  The liability 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.  

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 the statute of repose, or for an elected time-frame by the 
builder, in a specific state or per agreement with a general liability insurance carrier.  Constituents' interests are aligned to handle 
their claims relative to construction defects promptly and without attorney intervention. 

Marketing and Distribution

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 23 states and the District of Columbia.   

6

KINGSWAY FINANCIAL SERVICES INC.

Trinity  directly  markets  and  distributes  its  warranty  products  to  manufacturers,  distributors  and  installers  of  HVAC,  standby 
generator, commercial LED lighting and 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.

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.

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

Competition

IWS focuses exclusively on the automotive finance market with its core vehicle service agreement 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 are thus unable to 
deliver specialty expertise on par with IWS and do not give vehicle service agreement products the attention they require for 
healthy profitability and strong risk management.

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 refrigeration equipment 
than that of its competitors.

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; its over 20 years' 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.

Claims Management

Claims management is the process by which Extended Warranty determines the validity and amount of a claim.  We believe that 
claims management is fundamental to our operating results.  Our goal is to settle claims fairly for the benefit of our insureds and 
the insureds of our insurance company partners in a manner that is consistent with the insurance policy language and our regulatory 
and legal obligations.

IWS  effectively  and  efficiently  manages  claims  by  utilizing  in-house  expertise  and  information  systems.    IWS  employs  an 
experienced claims staff comprised of Automotive Service Excellence certified mechanics, knowledgeable in all aspects of vehicle 
repairs and potential claims.  Additionally, IWS owns its own proprietary database of historical claims data dating back over twenty 
years.  Management analyzes this database to drive real-time pricing adjustments and strategic decision-making.

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.  

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 responds 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.

7

KINGSWAY FINANCIAL SERVICES INC.

LEASED REAL ESTATE SEGMENT

Leased Real Estate includes the Company's subsidiary, CMC Industries, Inc. ("CMC").  CMC owns, 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 with a single customer, BNSF Railway 
Company.  Revenue from this single customer represents more than 10% of the Company’s consolidated revenues.  The Real 
Property is also subject to a mortgage, which is recorded as note payable in the consolidated balance sheets (the "Mortgage"). 

PRICING AND PRODUCT MANAGEMENT 

Responsibility  for  pricing  and  product  management  rests  with  the  Company's  individual  operating  subsidiaries  in  Extended 
Warranty.  Typically, teams 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 track loss performance on a monthly basis so as to alert the operating subsidiaries to the potential need to adjust 
forms or rates.

UNPAID LOSS AND LOSS ADJUSTMENT EXPENSES

The Company records a provision for its unpaid losses that have occurred as of a given evaluation date as well as for its estimated 
liability for loss adjustment expenses.  For a detailed description of the Company's process for establishing its provision for unpaid 
loss and loss adjustment expenses, see "Critical Accounting Estimates and Assumptions" section of MD&A.  For a rollforward of 
the provision for unpaid loss and loss adjustment expenses, net of amounts recoverable from reinsurers, see Note 16, "Unpaid Loss 
and Loss Adjustment Expenses," to the Consolidated Financial Statements.      

INVESTMENTS

We  manage  our  investments  to  support  our  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 
managed by a team of employees and advisors dedicated to the identification of investment opportunities that offer asymmetric 
risk/reward potential with a margin of safety supported by private market values.  The Investment Committee of the Board of 
Directors is responsible for monitoring the performance of our investments and compliance with the Company's investment policies 
and guidelines, which it reviews annually.  Investments held by our insurance subsidiary, Amigo, must comply with domiciliary 
state regulations that prescribe the type, quality and concentration of investments.

For  further  descriptions  of  the  Company's  investments,  see  our  disclosures  under  the  headings  "Investments"  and  "Critical 
Accounting Estimates and Assumptions" in MD&A and Note 8, "Investments," and Note 29, "Fair Value of Financial Instruments," 
to the Consolidated Financial Statements.

REGULATORY ENVIRONMENT

U.S. insurance companies are subject to the insurance holding company statutes in the jurisdictions in which they conduct business.  
These statutes require that each U.S insurance company in a holding company system register with the insurance department of 
its state of domicile and furnish information concerning the operations of companies in the holding company system that may 
materially affect the operations, management or financial condition of the insurers in the holding company domiciled in that state.  
These statutes also generally provide that all transactions among members of a holding company system be done at arm’s length 
and be shown to be fair and reasonable to the regulated insurer.  Transactions between insurance company subsidiaries and their 
parents and affiliates typically must be disclosed to the state regulators, and any material or extraordinary transaction requires 
prior approval of the applicable state insurance regulator.  A change of control of a domestic insurer or of any controlling person 
requires the prior approval of the state insurance regulator.  In general, any person who acquires 10% or more of the outstanding 
voting securities of the insurer or its parent company is presumed to have acquired control of the domestic insurer. 

U.S. insurance companies are required under the guaranty fund laws of most states in which they transact business to pay assessments 
up to prescribed limits to fund policyholder losses or liabilities of insolvent insurance companies.  U.S. insurance companies also 
are required to participate in various involuntary pools or assigned risk pools.  In most states, the involuntary pool participation 
is in proportion to the voluntary writings of related lines of business in such states.

U.S. insurance companies are subject to state laws and regulations that require diversification of our investment portfolios and 
that limit the amount of investments in certain categories.  Failure to comply with these laws and regulations would cause non-
conforming investments to be treated as non-admitted assets for purposes of measuring statutory surplus and, in some instances, 
would require divestiture.

8

KINGSWAY FINANCIAL SERVICES INC.

We have one U.S. insurance subsidiary, Amigo, which is organized and domiciled under the insurance statutes of Florida. To the 
best of our knowledge, we are in compliance with the regulations discussed above.

U.S. insurance companies are required to report their financial condition and results of operation in accordance with statutory 
accounting principles prescribed or permitted by state insurance regulators in conjunction with the National Association of Insurance 
Commissioners ("NAIC").  State insurance regulators also prescribe the form and content of statutory financial statements, perform 
periodic financial examinations of insurers, set minimum reserve and loss ratio requirements, establish standards for the types and 
amounts of investments and require minimum capital and surplus levels.  Such statutory capital and surplus requirements reflect 
risk-based capital ("RBC") standards promulgated by the NAIC.  These RBC standards are intended to assess the level of risk 
inherent in an insurance company's business and consider items such as asset risk, credit risk, underwriting risk and other business 
risks relevant to its operations.  In accordance with RBC formulas, an insurance company's RBC requirements are calculated and 
compared to its total adjusted capital, as defined by the NAIC, to determine whether regulatory intervention is warranted.  In 
general, insurers reporting surplus as regards policyholders below 200% of the authorized control level, as defined by the NAIC, 
at December 31 are subject to varying levels of regulatory action, including discontinuation of operations.  As of December 31, 
2018, surplus as regards policyholders reported by Amigo exceeded the 200% threshold.  Refer to Note 32, "Regulatory Capital 
Requirements and Ratios," to the Consolidated Financial Statements for further discussion. 

The state insurance department that has jurisdiction over Amigo may conduct on-site visits and examinations, especially as to 
financial condition, ability to fulfill obligations to policyholders, market conduct, claims practices and compliance with other laws 
and applicable regulations.  Typically, these examinations are conducted every three to five years.  In addition, if circumstances 
dictate, regulators are authorized to conduct special or target examinations of insurance companies to address particular concerns 
or issues.  The results of these examinations can give rise to regulatory orders requiring remedial, injunctive or other corrective 
action on the part of the company that is the subject of the examination or the assessment of fines or other penalties against that 
company.  The Florida Office of Insurance Regulation completed in 2016 a financial examination of Amigo for the three-year 
period ending December 31, 2014 and completed in the first quarter of 2018 a financial examination of Amigo for the two-year 
period ending December 31, 2016.  No financial statement adjustments were required as a result of either examination.

The  Gramm-Leach-Bliley Act  protects  consumers  from  the  unauthorized  dissemination  of  certain  personal  information.   The 
majority of states have implemented additional regulations to address privacy issues.  These laws and regulations apply to all 
financial institutions and require us to maintain appropriate procedures for managing and protecting certain personal information 
of our customers and to fully disclose our privacy practices to our customers.  We may also be exposed to future privacy laws and 
regulations, which could impose additional costs and adversely affect our results of operations or financial condition.

Vehicle service agreements are regulated in all states in the United States, and IWS is subject to these regulations.  Most states 
utilize the approach of the Uniform Service Contract Act which was adopted by the NAIC in the early 1990's.  Under that scheme, 
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 is in compliance with the regulations of each state in which 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.

The insurance carrier providing the contractual liability coverage for the insured warranty product offered by PWSC is designated 
as a surplus lines carrier in all states.  The offering of surplus lines insurance is regulated in all states.  The insurance carrier has 
designated an agent within PWSC who is a licensed property and casualty broker and a surplus lines broker in all states where 
such a license is required.  PWSC is in compliance with the regulations of each state in which it offers its insured warranty products.  
In addition, New Jersey, Maryland and the U.S. Department of Housing & Urban Development ("HUD") require PWSC to file its 
warranty plan documents and other company information for periodic review and approval to demonstrate compliance with new 
home warranty plan regulations promulgated by those jurisdictions.  HUD and New Jersey require such a filing every two years.  
Maryland requires a filing every year.  PWSC is in compliance with the filing requirements of each state and HUD.

EMPLOYEES

At December 31, 2018, we employed 123 personnel supporting our continuing operations, of which 122 were full-time employees.   

ACCESS TO REPORTS

Our 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 

9

KINGSWAY FINANCIAL SERVICES INC.

through our 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 2018 Annual 
Report and to consult any further disclosures Kingsway makes on related subjects 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, 2018, we had $90.5 million principal value of outstanding recourse subordinated debt, in the form of trust 
preferred debt instruments, with redemption dates beginning in December 2032.  And, related to our acquisition on March 1, 2019 
of The Penn Warranty Corporation ("Penn") and Prime Auto Care, Inc. ("Prime"), we have guaranteed $10.0 million of acquisition 
financing.  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, representing $90.5 million 
of principal value, and our acquisition financing of $10.0 million bear interest directly related to the London interbank offered 
interest rate for three-month U.S. dollar deposits or any equivalent replacement benchmark as defined in the underlying loan 
documents ("LIBOR"); 
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; 
•  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 may increase; 
• 
• 
our flexibility to adjust to changing market conditions and ability to withstand competitive pressures could be limited; 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 of $90.5 million principal value and our acquisition financing of $10.0 million related 
to the acquisition of Penn and Prime bear interest directly related to LIBOR.  As a result, increases in LIBOR would increase the 
cost of servicing our debt and could adversely affect our results of operations.  Each one hundred basis point increase in LIBOR 
would result in an approximately $1.0 million increase in our annual interest expense.

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

Our outstanding recourse subordinate debt of $90.5 million principal value, which has redemption dates ranging from December 
4, 2032 through January 8, 2034, and our acquisition financing of $10.0 million related to the acquisition of Penn and Prime, 
which has a maturity date of March 1, 2024, bear interest directly related to LIBOR and extend beyond 2021, by which time the 
United Kingdom’s Financial Conduct Authority, which regulates LIBOR, has announced it intends to phase out LIBOR.  It is 
unclear if at that time LIBOR will cease to exist or if new methods of calculating LIBOR will be established such that it continues 
to exist after 2021.  If LIBOR ceases to exist as defined in the indentures governing the Company’s outstanding recourse debt, 
the indentures provide fallback language for the respective agents to calculate an alternative LIBOR to be used in determining the 
Company’s  interest  expense  on  its  outstanding  recourse  debt.  At  this  time,  the  Company  cannot  yet  reasonably  estimate  the 
expected impact of a discontinuation of LIBOR.

10

KINGSWAY FINANCIAL SERVICES INC.

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 may 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.  A specific covenant under our debt indentures is our obligation to deliver audited financial 
statements for certain of our subsidiaries as of and for the year ended December 31, 2018.  Due to the delay in filing our 2018
Annual Report, we have been unable to meet these obligations, the failure of which could be declared events of default under the 
respective indentures.  As of the date of the filing of our 2018 Annual Report, none of the lenders or trustees responsible for 
administering any of our outstanding debt has declared an event of default, if required by the applicable indenture, notified us of 
an intent to accelerate any portion of the outstanding debt or charge default interest thereon, or pursued any other remedies available 
to it.  If an event of default does occur, it could trigger a default under our other debt instruments, and the holders of the defaulted 
debt instrument could declare amounts outstanding with respect to such debt to become immediately due and payable.  Upon such 
an event, our assets and cash flow may not be sufficient to fully repay borrowings under our outstanding debt instruments.  In 
addition, such a repayment under an event of default could adversely affect our liquidity and force us to sell assets to repay 
borrowings.

The  Investment  Committee  of  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. 

The Real Property is leased pursuant to a long-term triple net lease and the failure of the tenant to satisfy its obligations 
under the lease could adversely affect the condition of the Real Property or the results of the Leased Real Estate segment.

Because the Real Property is leased pursuant to a long-term triple net lease, we depend on the tenant to pay all insurance, taxes, 
utilities, common area maintenance charges, maintenance and repair expenses and to indemnify, defend and hold us harmless from 
and against various claims, litigation and liabilities arising in connection with its business, including any environmental liabilities.  
There can be no assurance that the tenant will have sufficient assets, income and access to financing to enable it to satisfy its 
payment obligations to us under the lease.  The inability or unwillingness of the tenant to meet its rent obligations to CMC or to 
satisfy its other obligations, including indemnification obligations, could materially adversely affect the business, financial position 
or results of operations of our Leased Real Estate segment.  Furthermore, the inability or unwillingness of the tenant to satisfy its 
other obligations under the lease, such as the payment of insurance, taxes and utilities, could materially and adversely affect the 
condition of the Real Property.

Our triple net lease agreement requires that the tenant maintain comprehensive liability and hazard insurance; however, there are 
certain types of losses (including losses arising from environmental conditions or of a catastrophic nature, such as earthquakes, 
hurricanes and floods) that may be uninsurable or not economically insurable.  Insurance coverage may not be sufficient to pay 
the  full  current  market  value  or  current  replacement  cost  of  a  loss.   Inflation,  changes  in  building  codes  and  ordinances, 
environmental considerations, and other factors also might make it infeasible to use insurance proceeds to replace the property 
after such property has been damaged or destroyed.  In addition, if we experience a loss that is uninsured or that exceeds policy 
coverage limits, we could lose the capital invested in the property as well as the anticipated future cash flows from the property.

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, 2018, our investments included $12.3 
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.  The low interest rate environment for fixed maturities 
that has existed for years also exposes us to reinvestment risk as these investments mature because the funds may be reinvested 
at rates lower than those of the maturing investments.

11

KINGSWAY FINANCIAL SERVICES INC.

As of December 31, 2018, our investments also included $0.9 million of equity investments, $4.8 million of limited liability 
investments, $26.0 million of limited liability investments, at fair value, $3.1 million of investments in private companies, at 
adjusted cost, $10.7 million of real estate investments, at fair value and other investments, at cost of $2.1 million.  These investments 
are less liquid than fixed maturities.  We generally make these investments with long-term time horizons in mind.  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.  

A difficult economy generally could materially adversely affect our business, results of operations or financial condition.

An adverse change in market conditions 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 affect on our results of operations or financial condition.  Certain trust accounts and 
letters of credit 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 and/or letter of credit agreements.  The value of collateral could fall below the levels 
required under these agreements putting the subsidiary or subsidiaries in breach of the agreements.

Market volatility may also make it more difficult to value certain of our investments if trading becomes less frequent.  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.  There 
can be no assurance that market conditions will not deteriorate in the near 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, 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.  In addition, as a result of recent financial events, we may face increased regulation.  Many of the other 
risk factors discussed in this Risk Factors section identify risks that result from, or are exacerbated by, financial economic downturn.  
These include risks related to our investments portfolio, the competitive environment and regulatory developments.

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 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.  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 provided certain indemnifications to the buyer of our non-standard automobile businesses, which could materially 
adversely affect our business, results of operations or financial condition.

On July 16, 2018, we announced we had entered into a definitive agreement to sell our non-standard automobile insurance companies 
Mendota, Mendakota and MCC (collectively "Mendota").  On October 18, 2018, we completed the previously announced sale of 
Mendota.  The final aggregate purchase price of $28.6 million was redeployed primarily to acquire equity investments, limited 
liability investments, limited liability investments, at fair value and other investments, which were owned by Mendota at the time 
of the closing, and to fund $5.0 million into an escrow account to be used to satisfy potential indemnity obligations under the 

12

KINGSWAY FINANCIAL SERVICES INC.

definitive stock purchase agreement.  As part of the transaction, we will indemnify the buyer for any loss and loss adjustment 
expenses with respect to open claims and certain specified claims in excess of Mendota’s carried unpaid loss and loss adjustment 
expenses at June 30, 2018.  The maximum obligation to the Company with respect to the open claims is $2.5 million.  There is 
no maximum obligation to the Company with respect to the specified claims. During 2019, Mendota notified us that it had entered 
into agreements to settle the specified claims.  We estimate we will incur a net loss of approximately $1.8 million related to the 
settlements of the specified claims, which we will report in our consolidated statement of operations for the year ended December 
31, 2019.  Our potential exposure under the indemnity obligation with respect to the open claims is not reasonably determinable, 
and no liability has been recorded in our Consolidated Financial Statements. No assurances can be given, however, that we will 
not be required to perform under the indemnity obligation for the open claims 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 $845.7 million as of December 31, 2018.  These U.S. NOLs can be available to reduce income taxes 
that might otherwise be incurred on future U.S. taxable income.  The utilization of these U.S. NOLs would have a positive effect 
on our cash flow.  Our operations, however, remain challenged, and 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, 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 (5%) percent or more of the value of our shares or 
are otherwise treated as five (5%) percent shareholders under Section 382 and the regulations promulgated thereunder increase 
their aggregate percentage ownership of the value of our shares by more than 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 (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 

13

KINGSWAY FINANCIAL SERVICES INC.

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 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. 

In light of financial performance and a number of material transactions executed over the years, the Company has been asked to 
respond to questions from and provide information to regulatory bodies overseeing insurance and/or securities laws in Canada 
and the United States.  The Company has cooperated in all respects with these reviews and has responded to information requests 
on a timely basis. 

Any failure to comply with applicable laws or regulations or the mandates of our insurance 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, could materially adversely affect our business, results of operations or 
financial  condition.    It  is  not  possible  to  predict  the  future  affect  of  changing  federal,  state  and  provincial  regulation  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.

Related to our recent acquisition of Penn and Prime, we acquired a reinsurance company domiciled in Turks and Caicos.  This 
reinsurance company is subject to the insurance statutes and regulatory requirements of the Turks and Caicos.  We are planning 
on the payment of dividends by the Turks and Caicos-domiciled reinsurance company in order to facilitate servicing the acquisition 
financing we incurred to acquire Penn and Prime.  The inability of the Turks and Caicos-domiciled reinsurance company to pay 
dividends could materially affect our holding company cash flow and liquidity if we were required to perform under our guarantee 
of the $10.0 million of acquisition financing incurred related to the acquisition of Penn and Prime.

Our business is subject to risks related to litigation.

In connection with our operations in the ordinary course of business, 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.

Our business is subject to risks related to regulatory actions.

The Department of Housing and Urban Development recently issued a final rule to eliminate the requirement that borrowers 
purchase 10-year protection plans in order to qualify for certain mortgages on newly constructed single-family homes when the 
home owner is utilizing an FHA loan.  It is unclear what effect this ruling may have on our sale of homebuilder warranties.  No 
assurances can be given, however, that the effect on us of this ruling will not result in 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.  We have in the past concluded that our internal controls over financial reporting related to 
income tax accounting for non-routine transactions and the adoption of ASU 2014-09 were not effective. In the 2018 Annual 
Report, we have identified the existence of material weaknesses in internal control over financial reporting related to the accounting 
for and disclosure of certain complex and nonrecurring transactions; the accounting for and disclosure of certain other items; 
monitoring the collectability of accounts receivable balances; other-than-temporary impairment on equity method investments; 
and certain account reconciliations.

14

KINGSWAY FINANCIAL SERVICES INC.

As discussed in Note 3, "Restatement of Previously Issued Financial Statements," to the Consolidated Financial Statements, we 
have restated our consolidated financial statements as of and for the year ended December 31, 2017.  Although we previously 
remediated  the  material  weakness  related  to  income  tax  accounting  for  non-routine  transactions  and  are  actively  engaged  in 
developing and implementing remediation plans as described Item 9A, Controls and Procedures, of this 2018 Annual Report, 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.

STRATEGIC RISK

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

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 and ultimately selling Mendota 
on October 18, 2018, with the objective of focusing on our Extended Warranty segment, 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 reduce our holding company expenses while at the same time retaining staff 
given the significant reduction in size and scale of our businesses.

We have divested a number of subsidiaries.  At the same time, we have been downsizing our holding company expense base in 
an attempt to compensate for the reduction in scale.  There can be no assurance that our remaining 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 few large companies, which market service agreements 
to credit unions 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 IWS that market service agreements to credit unions either 
on a regional basis or a less robust national basis.  In addition, the homebuilder warranty market in which we operate is comprised 
of several competitors.  There may also be other companies of which we are not aware that may be planning to enter the vehicle 
service agreement and homebuilder warranty industries.

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 and homebuilder warranties 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;
assumption of unknown material liabilities, including deficient provisions for unpaid loss and loss adjustment expenses;
diversion of management's attention from other business concerns;
failure to achieve financial or operating objectives; and
potential loss of customers or key employees of acquired companies.

15

KINGSWAY FINANCIAL SERVICES INC.

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

Engaging in new business start-ups 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 the formation of a new business venture and, as a result of such discussions, 
may form and capitalize a new business.

New business start-ups entail numerous potential risks, including the following:

• 
• 
• 
• 
• 

identification of appropriate management to run the new business;
understanding the strategic, competitive and marketplace dynamics of the new business and, perhaps, industry;
establishment of proper financial and operational controls;
diversion of management's attention from other business concerns; and
failure to achieve financial or operating objectives.

We may not be able to operate successfully any business, operations, personnel, services or products that we may organize as a 
new business start-up in the future.

Our company has an executive officer and former executive officers, currently contracted to us under advisory agreements, 
who also serve as directors and executive officers for 1347 Property Insurance Holdings, Inc., Atlas Financial Holdings, 
Inc., Limbach Holdings, Inc. and Itasca Capital Ltd., entities in which we have held investments, which could lead to 
conflicting interests.

As a result of our having previously spun off 1347 Property Insurance Holdings, Inc. ("PIH") and Atlas Financial Holdings, Inc. 
("Atlas"); formed 1347 Capital Corp., which later entered into a business combination with Limbach Holdings, Inc. ("Limbach"); 
and invested in Itasca Capital Ltd. ("ICL"), we have an executive officer and former executive officers, currently contracted to us 
under advisory agreements, who also serve as directors for PIH, Atlas, Limbach and ICL and who serve as executive officers for 
ICL.  Our executive officers, former executive officers currently contracted to us under advisory agreements and members of our 
Company's board of directors have fiduciary duties to our stockholders; likewise, persons who serve in similar capacities at PIH, 
Atlas, Limbach and ICL have fiduciary duties to those companies’ stockholders.  We may find, though, the potential for a conflict 
of  interest  if  our  Company  and  one  or  more  of  these  other  companies  pursue  acquisitions,  investments  and  other  business 
opportunities that may be suitable for each of us.  Our executive officers and former executive officers currently contracted to us 
under advisory agreements who find themselves in these multiple roles may, as a result, have conflicts of interest or the appearance 
of conflicts of interest with respect to matters involving or affecting more than one of the companies to which they owe fiduciary 
duties.  Furthermore, our executive officers and former executive officers currently contracted to us under advisory agreements 
who find themselves in these multiple roles own stock options, shares of common stock and other securities in some of these 
entities.  These ownership interests could create, or appear to create, potential conflicts of interest when the applicable individuals 
are faced with decisions that could have different implications for our Company and these other entities.  Our Audit Committee 
reviews potential conflicts that may arise on a case-by-case basis, keeping in mind the applicable fiduciary duties owed by the 
executive officers and directors of each entity.  From time to time, we may enter into transactions with or participate jointly in 
investments with PIH, Atlas, Limbach or ICL.  There can be no assurance that we will not create new situations where our directors 
or executive officers serve as directors or executive officers in future investment holdings of our Company.

OPERATIONAL RISK

Our provisions for unpaid loss and loss adjustment expenses may be inadequate, which would result in a reduction in our 
net income and could adversely affect our financial condition.

Our provisions for unpaid loss and loss adjustment expenses at Amigo do not represent an exact calculation of our actual liability 
but are estimates involving actuarial and statistical projections at a given point in time of what we expect to be the cost of the 
ultimate settlement and administration of reported and IBNR claims.  The process for establishing the provision for unpaid loss 
and loss adjustment expenses reflects the uncertainties and significant judgmental factors inherent in estimating future results of 
both reported and IBNR claims and, as such, the process is inherently complex and imprecise.  These estimates are based upon 
various factors, including:

• 
• 
• 
• 

actuarial projections of the cost of settlement and administration of claims reflecting facts and circumstances then known;
estimates of future trends in claims severity and frequency;
legal theories of liability;
variability in claims-handling procedures;

16

KINGSWAY FINANCIAL SERVICES INC.

• 
• 

• 

economic factors such as inflation;
judicial  and  legislative  trends,  actions  such  as  class  action  lawsuits,  and  judicial  interpretation  of  coverages  or 
policy exclusions; and
the level of insurance fraud.

Most or all of these factors are not directly quantifiable, particularly on a prospective basis, and the effects of these and unforeseen 
factors could negatively affect our ability to accurately assess the risks of the policies that we write.  In addition, there may be 
significant reporting lags between the occurrence of insured events and the time they are actually reported to us and additional 
lags between the time of reporting and final settlement of claims.

As  time  passes  and  more  information  about  the  claims  becomes  known,  the  estimates  are  appropriately  adjusted  upward  or 
downward to reflect this additional information.  Because of the elements of uncertainty encompassed in this estimation process, 
and the extended time it can take to settle many of the more substantial claims, several years of experience may be required before 
a meaningful comparison can be made between actual losses and the original provision for unpaid loss and loss adjustment expenses.

We cannot assure that we will not have unfavorable development in the future and that such unfavorable development will not 
have a material adverse effect on our business, results of operations or financial condition. 

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 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.

Our reliance on credit unions and automobile sales could adversely affect our ability to maintain business.

We market and distribute our vehicle service agreements through a network of credit unions in the United States.  As a result, we 
rely heavily on these credit unions to attract new business.  While these distribution arrangements tend to be exclusive between 
us and each credit union, we have competitors that offer similar products exclusively through credit unions.  Loss of all or a 
substantial portion of our existing credit union relationships; a significant decline in membership in our existing credit union 
relationships; or 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 homebuilders and new home sales could adversely affect our ability to maintain business.

We market and distribute our core home warranty products through homebuilders throughout the United States.  As a result, we 
rely heavily on these homebuilders to generate new business.  The builders are part of the new home construction industry, which 
is cyclical and closely correlated with large macro-economic factors, such as interest and unemployment rates, wage growth, and 
government regulation.  We bill certain builders at the end of the policy period, which could extend over more than one year.  
During economic downturns, our customers build fewer homes and also reduce operating expenses by insourcing key functions, 
such as warranty administration; in turn, our revenue has the propensity to decline during these times.  Loss of all or a substantial 
portion  of  our  existing  homebuilder relationships;  a  significant decline  in  new  home  sales;  or  collection  risk  due  to  unbilled 
accounts receivable 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.

17

KINGSWAY FINANCIAL SERVICES INC.

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;
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.

Our results of operation or financial condition could be adversely affected by the results of our voluntary run-off of our 
insurance subsidiary.

The Company currently has Amigo operating in voluntary run-off.  Our success at managing this run-off is highly dependent upon 
proper claim-handling, the outcomes of the remaining open claims and the availability of the necessary liquidity to pay claims 
when due.  As a result, we are dependent in part on our ability to retain the services of appropriately trained and supervised claim-
handling personnel.  The loss of the services of any of our key claim-handling personnel working in our run-off, or the inability 
to identify, hire and retain other highly qualified claim-handling personnel in the future, could adversely affect our results of 
operations.  We are also dependent upon the outcomes of the remaining open claims, some of which may be volatile.  During 
2019, Amigo agreed to settle three related open claims for approximately $0.8 million in excess of the provision for unpaid loss 
and loss adjustment expenses carried by Amigo for these three open claims.   This amount will be reported in our consolidated 
statement of operations for the year ended December 31, 2019.  We are also dependent on the continuing availability of the 
necessary liquidity to settle claims properly.  See the "Liquidity and Capital Resources" section of MD&A for additional detail 
regarding the voluntary run-off of Amigo.

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.

18

KINGSWAY FINANCIAL SERVICES INC.

Item 2. Properties 

Leased Properties

Extended Warranty leases facilities with an aggregate square footage of approximately 25,836 at four locations in three states.  
The latest expiration date of the existing leases is in July 2026.

The Company leases a facility for its corporate office with an aggregate square footage of approximately 6,338 at one location in 
one state. The expiration date of the existing lease is in January  2023.

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

Owned Properties
Leased Real Estate owns the Real Property, which is subject to a long-term triple net lease agreement.  The Real Property includes 
rail car tracks which provide rail car storage spaces and has 72 miles of double-ended rail track.  The Real Property also contains 
a 5,760 square foot office building with an attached observation tower comprised of 1,150 square feet.  

Investment Properties

The Company owns six investment properties subject to long-term triple net lease agreements.  These properties comprise 57,360 
square feet leased to tenants in the distribution and retail sectors.

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.

Item 4. Mine Safety Disclosures

Not applicable.

Part II

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

Market Information 

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

19

KINGSWAY FINANCIAL SERVICES INC.

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. 

2018

Quarter 4

Quarter 3

Quarter 2

Quarter 1

2017

Quarter 4

Quarter 3

Quarter 2

Quarter 1

Shareholders of Record

$

NYSE

High - US$

Low - US$

$

2.87

3.30

4.65

5.85

6.05

6.20

6.30

6.50

1.87

2.40

2.75

3.65

4.95

5.45

5.35

5.40

As of February 26, 2020, the closing sales price of our common shares as reported by the NYSE was $1.59 per share.  

As of February 27, 2020, we had 21,866,959 common shares issued and outstanding, held by approximately 3,300 shareholders 
of record.  

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 included in Part III, 
Item 12 of this 2018 Annual Report.

Recent Sales of Unregistered Securities

During the year ended December 31, 2018, we did not have any unregistered sales of our equity securities.

Issuer Purchases of Equity Securities

During the year ended December 31, 2018, we did not have any repurchases of our equity securities. 

20

KINGSWAY FINANCIAL SERVICES INC.

Performance Graph

The following stock performance graph shows a comparison of cumulative total shareholder return on the Company's common 
stock for the period beginning on December 31, 2013 and ending on December 31, 2018 with cumulative total return of the Russell 
MicroCap Index and the SNL MicroCap U.S. Financial Services Index.  Kingsway is not a constituent of either of these two 
indices.  The graph shows the change in value of an initial one hundred dollar investment over the period indicated, assuming all 
dividends have been reinvested.

Company/Index

Kingsway

Russell MicroCap

SNL Micro Cap U.S. Financial Services

Years ended December 31,

2013

2014

2015

2016

2017

2018

$

$

$

100 $

100 $

100 $

142 $

104 $

99 $

117 $

98 $

73 $

160 $

118 $

72 $

129 $

134 $

97 $

74

116

86

21

KINGSWAY FINANCIAL SERVICES INC.

Item 6. Selected Financial Data

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.

22

  
 
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  discussion  and  analysis  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 2018 Annual Report and reflects the effects of the error 
corrections and previously identified immaterial accounting adjustments discussed in Note 3, "Restatement of Previously Issued 
Financial Statements," to the Consolidated Financial Statements.

OVERVIEW

Kingsway is a Delaware holding company with operating subsidiaries located in the United States.  The Company owns or controls 
subsidiaries primarily in the extended warranty, asset management and real estate industries.  Kingsway conducts its business 
through the following two reportable segments: Extended Warranty and Leased Real Estate.  

The  Company  previously  conducted  its  business  through  a  third  reportable  segment,  Insurance  Underwriting.    Insurance 
Underwriting included the following subsidiaries of the Company: Mendota Insurance Company, Mendakota Insurance Company, 
Mendakota  Casualty  Company,  Kingsway  Amigo  Insurance  Company  ("Amigo")  and  Kingsway  Reinsurance  Corporation 
("Kingsway Re").  Mendota Insurance Company, Mendakota Insurance Company and Mendakota Casualty Company are referred 
to collectively herein as "Mendota."  On July 16, 2018, the Company announced that it had entered into a definitive agreement to 
sell Mendota.  On October 18, 2018, the Company announced that the sale was completed.  As a result, Mendota has been classified 
as discontinued operations and the results of their operations are reported separately for all periods presented.  As a consequence 
of classifying Mendota as discontinued operations, the remaining composition of the Insurance Underwriting segment no longer 
meets  the  criteria  of  a  reportable  segment.   As  such,  all  segmented  information  has  been  restated  to  exclude  the  Insurance 
Underwriting segment for all periods presented.   The operating results of Amigo and Kingsway Re, previously included in the 
Insurance Underwriting segment, are now included in Other income and expenses not allocated to segments, net.

Extended Warranty includes the following subsidiaries of the Company: IWS Acquisition Corporation ("IWS"), Trinity Warranty 
Solutions LLC ("Trinity") and Professional Warranty Service Corporation ("PWSC"). Throughout this 2018 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 23 states and the District of Columbia to their members.

Trinity  sells  heating,  ventilation,  air  conditioning  ("HVAC"),  standby  generator,  commercial  LED  lighting  and  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 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.

PWSC sells new 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.

Leased Real Estate includes the Company's subsidiary, CMC Industries, Inc. ("CMC").  CMC owns, 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 a 
mortgage, which is recorded as note payable in the consolidated balance sheets (the "Mortgage").  Throughout this 2018 Annual 
Report, the term "Leased Real Estate" is used to refer to this segment. 

NON U.S.-GAAP FINANCIAL MEASURE

Throughout  this  2018 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 loss, 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.

23

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

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 28, "Segmented Information," 
to the Consolidated Financial Statements, regarding reportable segment information. The nearest comparable U.S. GAAP measure 
to segment operating income is loss from continuing operations before income tax expense (benefit) that, in addition to segment 
operating income, includes net investment income, net realized (losses) gains, gain on change in fair value of equity investments, 
loss  on  change  in  fair  value  of  limited  liability  investments,  at  fair  value,  net  change  in  unrealized  loss  on  private  company 
investments, interest expense not allocated to segments, other income and expenses not allocated to segments, net, amortization 
of intangible assets, contingent consideration benefit, loss on change in fair value of debt, gain on disposal of subsidiary and equity 
in net (loss) income of investee.  A reconciliation of segment operating income to loss from continuing operations before income 
tax expense (benefit) for the years ended December 31, 2018 and December 31, 2017 is presented in Table 1 of the "Results of 
Continuing Operations" section of MD&A.

CRITICAL ACCOUNTING ESTIMATES AND ASSUMPTIONS

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 critical accounting estimates and assumptions 
in the accompanying consolidated financial statements include the provision for unpaid loss and loss adjustment expenses; valuation 
of fixed maturities and equity investments; impairment assessment of investments; valuation of limited liability investments, at 
fair value; valuation of real estate investments; valuation of deferred income taxes; valuation of mandatorily redeemable preferred 
stock; valuation and impairment assessment of intangible assets; goodwill recoverability; deferred acquisition costs; fair value 
assumptions for subordinated debt obligations; and revenue recognition. 

Provision for Unpaid Loss and Loss Adjustment Expenses   

Overview 

The Company records a provision for unpaid losses that have occurred as of a given evaluation date as well as for its estimated 
liability for loss adjustment expenses.  The provision for unpaid losses includes a provision, commonly referred to as case reserves, 
for losses related to reported claims as well as a provision for losses related to claims incurred but not reported (“IBNR”).  The 
provision for loss adjustment expenses represents the cost to investigate and settle claims. 

The provision for unpaid loss and loss adjustment expenses does not represent an exact calculation of the liability but instead 
represents management's best estimate at a given accounting date, utilizing actuarial and statistical procedures, of the undiscounted 
estimates of the ultimate net cost of all unpaid loss and loss adjustment expenses.  Management continually reviews its estimates 
and adjusts its provision as new information becomes available.  In establishing the provision for unpaid loss and loss adjustment 
expenses, the Company also takes into account estimated recoveries, reinsurance, salvage and subrogation. 

Any adjustments to the provision for unpaid loss and loss adjustment expenses are reflected in the consolidated statements of 
operations in the periods in which they become known, and the adjustments are accounted for as changes in estimates.  Even after 
such adjustments, ultimate liability or recovery may exceed or be less than the revised provisions.  An adjustment that increases 
the provision for unpaid loss and loss adjustment expenses is known as unfavorable development or a deficiency and will reduce 
net income while an adjustment that decreases the provision is known as favorable development or a redundancy and will increase 
net income. 

Process for Establishing the Provision for Unpaid Loss and Loss Adjustment Expenses 

The process for establishing the provision for unpaid loss and loss adjustment expenses reflects the uncertainties and significant 
judgmental factors inherent in predicting future results of both reported and IBNR claims.  As such, the process is inherently 
complex and imprecise and estimates are constantly refined.  The process of establishing the provision for unpaid loss and loss 
adjustment expenses relies on the judgment and opinions of a large number of individuals, including the opinions of the Company's 
external reserving actuaries. 

24

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

Factors  affecting  the  provision  for  unpaid  loss  and  loss  adjustment  expenses  include  the  continually  evolving  and  changing 
regulatory and legal environment; actuarial studies; professional experience and expertise of the Company's claims department 
personnel and independent adjusters retained to handle individual claims; the quality of the data used for projection purposes; 
existing claims management practices, including claim-handling and settlement practices; the effect of inflationary trends on future 
loss settlement costs; court decisions; economic conditions; and public attitudes. 

The process for establishing the provision for loss and loss adjustment expenses begins with the collection and analysis of claim 
data.  Data on individual reported claims, both current and historical, including paid amounts and individual claim adjuster estimates, 
are grouped by common characteristics and evaluated by the Company’s external reserving actuaries in their analyses to estimate 
ultimate claim liabilities.  Such data is occasionally supplemented with external data as available and when appropriate.

Our Company’s external reserving actuaries use the following generally accepted actuarial loss and loss adjustment expenses 
reserving methods in our analysis, for each coverage or segment that we analyze: 

• 

• 

• 

Paid Loss Development - we use historical loss and loss adjustment expense payments over discrete periods of time to 
estimate future loss and loss adjustment expense payments.  Paid development methods assume that the patterns of paid 
loss and loss adjustment expenses that occurred in past periods will be similar to loss and loss adjustment expense payment 
patterns that will occur in future periods. 

Incurred Loss Development - we use historical case incurred loss and loss adjustment expenses (the sum of cumulative 
loss and loss adjustment expense payments plus outstanding unpaid case losses) over discrete periods of time to estimate 
future loss and loss adjustment expenses.  Incurred development methods assume that the case loss and loss adjustment 
expenses reserving practices are consistently applied over time. 

Frequency and Severity - we use historical claim count development over discrete periods of time to estimate future claim 
counts.  We divide projected ultimate claim counts by an exposure base (earned premiums or exposures), select expected 
claim frequencies from the results, and adjust them for trends based on internal and external information.  Concurrently, 
we divide projected ultimate losses by the projected ultimate claim counts to select expected loss severities.  We use 
internal and external information to trend the severities and combine them with the trended, projected frequencies to 
develop ultimate loss projections.

The methods above all calculate an estimate of total ultimate losses.  Our provision for loss and loss adjustment expenses is 
calculated by subtracting total paid losses from our estimate of total ultimate losses.  Our estimate for IBNR is calculated by 
subtracting case reserves from our provision for loss and loss adjustment expenses.

Each estimation method has its own set of assumption variables and its own advantages and disadvantages, with no single estimation 
method being better than the others in all situations and no one set of assumptions being meaningful for all coverages or segments.  
For example, Paid Loss Development does not make use of case reserves, and can be more stable when there are changes to the 
case reserving process.  Frequency and Severity, by estimating the frequency separately from severity, can assist in understanding 
the underlying dynamics when either frequency or severity is changing substantially.

The relative strengths and weaknesses of the particular estimation methods when applied to a particular group of claims can also 
change over time; therefore, the actual choice of estimation method can change with each evaluation.  The estimation methods 
chosen are those that are believed to produce the most reliable indication at a particular evaluation date. 

We monitor the actual emergence of loss and loss adjustment expenses data and compare it to the expected emergence implied by 
our booked estimates.  Differences in these are part of our considerations for whether it is appropriate to modify our assumptions 
for developing the estimated provision for unpaid loss and loss adjustment expenses. 

We review the adequacy of the provision for unpaid loss and loss adjustment expenses quarterly.  For our year-end analysis, we 
re-estimate the ultimate losses for each coverage, by accident year.  This involves performing a complete update of the historical 
development factors used in our analysis, incorporating the experience of the most recent calendar year.  On a quarterly basis, we 
perform a more limited review, which can entail, for example, a comparison of the expected losses to be paid during the quarter 
versus actual payments, or other similar comparisons to determine the extent to which a given segment is performing as expected.  
In some cases, a re-estimation (similar to the year-end analysis) may be determined to be useful as part of a quarterly analysis, 
and we may make adjustments to ultimate losses in response to the results of this analysis.  We adjust carried unpaid loss and loss 

25

 
KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

adjustment expenses as we learn additional information, and reflect these adjustments in the accounting periods in which they are 
determined. 

A basic premise in most actuarial analyses is that past patterns demonstrated in the data will repeat themselves in the future, absent 
a material change in the associated risk factors.  Significant structural changes to the available data, product mix or organization 
can materially affect the provision for loss and loss adjustment expenses. 

Informed judgment is applied throughout the process.  This includes the application of various individual experiences and expertise 
to multiple sets of data and analyses.  In addition to actuaries, experts involved with the reserving process also include underwriting 
and claims personnel and lawyers, as well as other company management.  As a result, management may have to consider varying 
individual viewpoints when establishing the provision for unpaid loss and loss adjustment expenses. 

Our estimate of the provision for unpaid loss and loss adjustment expenses is proposed each quarter by our external reserving 
actuaries and approved by management.  We begin the process each quarter by responding to detailed information requests submitted 
by our external reserving actuaries.  Upon completion of their estimation analysis of the provision for unpaid loss and loss adjustment 
expenses, the results are discussed with management.  As part of this discussion, the analyses supporting the actuarial estimates 
of IBNR by line of business are reviewed.  The external reserving actuaries also present explanations supporting any changes to 
the underlying assumptions used to calculate the indicated estimates.  A review of the resulting variance between the indicated 
provision for unpaid loss and loss adjustment expenses and the carried provision for unpaid loss and loss adjustment expenses 
takes place.  Management engages in a discussion with the external reserving actuaries and supplies supplemental information in 
support of assumptions it believes should be challenged.  The external reserving actuaries review the supplemental information 
and return with their recommendation in regards to the provision for unpaid loss and loss adjustment expenses that should be 
booked to reflect their analytical assessment and view of estimation risk.  After discussion of these analyses and all relevant risk 
factors, we determine whether the carried provision for unpaid loss and loss adjustment expenses requires adjustment.

Our external reserving actuaries have also developed as part of their actuarial reports to the Company an estimated range around 
the carried provision at December 31, 2018 of $2.1 million for unpaid loss and loss adjustment expenses for our property and 
casualty companies.  Their reports indicate that a carried provision for unpaid loss and loss adjustment expenses anywhere between 
$1.8 million and $2.5 million for the Company at December 31, 2018 would fall within their reasonable range of estimation.  This 
range does not present a forecast of future redundancy or deficiency since actual development of future paid losses related to the 
current provision for unpaid loss and loss adjustment expenses may be affected by many variables. The provision for unpaid loss 
and loss adjustment expenses recorded at December 31, 2018 represents our best estimate of the ultimate amounts that will be 
paid.

To the extent that the ultimate paid losses are higher or lower than the provision for unpaid loss and loss adjustment expenses 
recorded by the Company at December 31, 2018, the differences would be recorded in the Company’s consolidated statements of 
operations in the accounting periods in which they are determined.  There can be assurance that such differences would not be 
material.

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 loss in 2018.  
Prior to 2018, changes in fair value of equity investments were recognized in other comprehensive loss.  See Note 4, "Recently 
Issued Accounting Standards," to the Consolidated Financial Statements, for further details regarding the adoption of ASU 2016-01, 
Financial Instruments-Overall (Subtopic 825-10): Recognition and Measurement of Financial Assets and Financial Liabilities 
("ASU 2016-01").  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 and equity investments 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. 

26

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

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.

Impairment Assessment of Investments 

Prior to the adoption of ASU 2016-01, equity investments were considered available-for-sale and were included in the analysis of 
other-than-temporary impairments.  Following the adoption of ASU 2016-01 beginning with the first quarter of 2018, the Company 
includes only its investments in fixed maturities and investments in private companies in its quarterly impairment analysis.

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 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 the 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 past 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.

As a result of the analysis performed by the Company to determine declines in market value that are other-than-temporary, there 
were no write downs for other-than-temporary impairment related to available-for-sale investments recorded for the years ended 
December 31, 2018 and December 31, 2017.  As a result of the analysis performed with respect to limited liability investments, 
at fair value, the Company recorded impairments of $0.1 million and $0.1 million, which are included in loss on change in fair 
value of limited liability investments, at fair value in the consolidated statements of operations, for the years ended December 31, 
2018 and December 31, 2017, respectively.

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.

As a result of the analysis performed with respect to investments in private companies, the Company recorded impairments of 
$1.0 million and $2.0 million for the years ended December 31, 2018 and December 31, 2017, respectively, which are included 
in net change in unrealized loss on private company investments in the consolidated statements of operations.

27

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

At each reporting date, and more frequently when conditions warrant, management assesses its investment in investee for potential 
impairment.  If management's assessment indicates that there is objective evidence of impairment, the investee is written down to 
its recoverable amount, which is determined as the higher of its fair value less costs to sell and its value in use.  As a result of the 
analysis performed with respect to investment in investee, the Company recorded impairments of $1.7 million and zero for the 
years ended December 31, 2018 and December 31, 2017, respectively, which are included in equity in net (loss) income of investee 
in the consolidated statements of operations. 

Valuation of Limited Liability Investments, at Fair Value

Limited liability investments, at fair value represent the Company's investment in 1347 Investors LLC ("1347 Investors") as well 
as 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.  The Company owns 26.7% of the outstanding units of 1347 
Investors.  The fair value of this investment is calculated based on a model that distributes the net equity of 1347 Investors to all 
classes of membership interests. The model uses quoted market prices and significant market observable inputs.  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 29, "Fair Value of Financial Instruments," to the Consolidated 
Financial Statements for further information.  

Valuation of 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 applies this rate to the asset under consideration.  The cap rates used during underwriting and subsequent valuation 
at year-end 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.  

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 past 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, 2018, the Company maintains a valuation allowance of $171.5 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. 

28

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

Valuation of Mandatorily Redeemable Preferred Stock

Mandatorily redeemable preferred stock is recorded at the time of issuance based upon the gross proceeds of the offering less (i) 
proceeds of the offering allocated to additional paid-in capital based upon the relative fair values of equity-classified warrants 
issued as part of the offering and the preferred stock without the warrants; (ii) proceeds of the offering allocated to additional paid-
in capital based upon the calculation of a beneficial conversion feature; and (iii) costs of the offering allocated to the preferred 
stock.  The discount to the carrying value of the preferred stock created by the allocation of proceeds to the warrants and a beneficial 
conversion feature and the allocation of offering costs to the preferred stock are accreted over time as dividend expense.  Additional 
information  regarding  our  mandatorily  redeemable  preferred  stock  is  included  in  Note  25,  "Class A  Preferred  Stock,"  to  the 
Consolidated Financial Statements.

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  vehicle  service  agreements  in-force,  database,  customer  relationships,  in-place  lease  and  non-compete  agreement.  
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 a tenant relationship and trade names.  Intangible assets with an indefinite life are 
assessed for impairment annually as of December 31, or more frequently if events or circumstances indicate that the carrying value 
may not be recoverable.  The Company has the option to perform a qualitative assessment to determine whether it is more likely 
than not that an indefinite-lived intangible asset is impaired.  If facts and circumstances indicate that it is more likely than not that 
the intangible asset is impaired, a fair value-based impairment test would be required.  Management must make estimates and 
assumptions in determining the fair value of indefinite-lived intangible assets that may affect any resulting impairment write-
down.   This  includes assumptions  regarding future cash  flows  and future  revenues from  the related intangible assets  or their 
reporting units.  Management then compares the fair value of the indefinite-lived intangible assets to their respective carrying 
amounts.  If the carrying amount of an intangible asset exceeds the fair value of that intangible asset, an impairment is recorded.  
No impairment charges were recorded against intangible assets in 2018 or 2017.  Additional information regarding our intangible 
assets is included in Note 13, "Intangible Assets," to the Consolidated Financial Statements.

Goodwill Recoverability

Goodwill is assessed for impairment annually as of December 31, or more frequently if events or circumstances indicate that the 
carrying value may not be recoverable.  The Company has the option to perform a qualitative assessment to determine whether it 
is more likely than not that the fair value of a reporting unit is less than its carrying amount.  If facts and circumstances indicate 
that it is more likely than not that the goodwill is impaired, a fair value-based impairment test would be required.  The goodwill 
impairment test is a two-step process that requires management to make judgments in determining what assumptions to use in the 
calculation. The first step of the process consists of estimating the fair value of each reporting unit based on valuation techniques, 
including a discounted cash flow model using revenue and profit forecasts, and comparing those estimated fair values with the 
carrying values of the assets and liabilities of the reporting unit, which includes the allocated goodwill.  If the estimated fair value 
is less than the carrying value, a second step is performed to compute the amount of the impairment, if any, by determining an 
implied fair value of goodwill.  The determination of the implied fair value of goodwill of a reporting unit requires management 
to allocate the estimated fair value of the reporting unit to the assets and liabilities of the reporting unit.  Any unallocated fair value 
represents the implied fair value of goodwill, which is compared to its corresponding carrying value.  For reporting units with a 
negative book value, qualitative factors are evaluated to determine whether it is necessary to perform the second step of the goodwill 
impairment test.  No impairment charges were recorded against goodwill in 2018 or 2017.  Additional information regarding our 
goodwill is included in Note 12, "Goodwill," to the Consolidated Financial Statements.

Deferred Acquisition Costs

Deferred acquisition costs represent the deferral of expenses that we incur related to successful efforts to acquire new business or 
renew  existing  business.   Acquisition  costs,  primarily  commissions  and  agency  expenses  related  to  issuing  vehicle  service 
agreements, are deferred and charged against income ratably over the terms of the related vehicle service agreements.  Management 
regularly reviews the categories of acquisition costs that are deferred and assesses the recoverability of this asset.  

29

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

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. 

Revenue Recognition

Refer to Note 2, "Summary of Significant Accounting Policies," and Note 20, "Revenue from Contracts with Customers," to the 
Consolidated Financial Statements for information about our revenue recognition accounting policies.

30

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

RESULTS OF CONTINUING OPERATIONS 

A reconciliation of total segment operating income to net loss for the years ended December 31, 2018 and December 31, 2017 is 
presented in Table 1 below:

Table 1 Segment Operating Income for the Years Ended December 31, 2018 and December 31, 2017  
For the years ended December 31 (in thousands of dollars)

Segment operating income

Extended Warranty

Leased Real Estate

Total segment operating income

Net investment income

Net realized (losses) gains

Gain on change in fair value of equity investments

Loss on change in fair value of limited liability investments, at fair value

Net change in unrealized loss on private company investments

Interest expense not allocated to segments

Other income and expenses not allocated to segments, net

Amortization of intangible assets

Contingent consideration benefit

Loss on change in fair value of debt

Gain on disposal of subsidiary

Equity in net (loss) income of investee

Loss from continuing operations before income tax expense (benefit)

Income tax expense (benefit)
(Loss) income from continuing operations

Loss on liquidation of subsidiary, net of taxes

Income (loss) from discontinued operations, net of taxes

(Loss) gain on disposal of discontinued operations, net of taxes
Net loss

2018

2017

Change

4,215

2,485

6,700

2,957
(17)
381
(7,393)
(1,629)
(7,407)
(8,963)
(2,376)
—
(1,720)
17
(2,499)
(21,949)
315
(22,264)
—

1,064
(7,136)
(28,336)

3,680

3,099

6,779

7,087

306

—
(1,832)
(758)
(6,348)
(10,503)
(1,085)
212
(8,487)
—

2,115
(12,514)
(16,688)
4,174
(494)
(16,306)
1,017
(11,609)

535
(614)
(79)
(4,130)
(323)
381
(5,561)
(871)
(1,059)
1,540
(1,291)
(212)
6,767

17
(4,614)
(9,435)
17,003
(26,438)
494

17,370
(8,153)
(16,727)

(Loss) Income from Continuing Operations, Net Loss and Diluted Loss per Share 

For the year ended December 31, 2018, we incurred a loss from continuing operations of $22.3 million ($1.13 per diluted share) 
compared to income from continuing operations of $4.2 million (loss of $0.05 per diluted share) for the year ended December 31, 
2017.  The loss from continuing operations for the year ended December 31, 2018 is primarily attributable to interest expense not 
allocated to segments, other income and expenses not allocated to segments, net, amortization of intangible assets, loss on change 
in fair value of limited liability investments, at fair value, loss on change in fair value of debt and equity in net loss of investee, 
partially offset by operating income in Extended Warranty and Leased Real Estate.  The income from continuing operations for 
the year ended December 31, 2017 is primarily attributable to operating income in Extended Warranty and Leased Real Estate, 
net investment income, gain on change in fair value of limited liability investments, at fair value, equity in net income of investee 
and income tax benefit, partially offset by interest expense not allocated to segments, other income and expenses not allocated to 
segments, net, amortization of intangible assets and loss on change in fair value of debt.

For the year ended December 31, 2018, we reported net loss of $28.3 million ($1.41 per diluted share) compared to $11.6 million
($0.79 per diluted share) for the year ended December 31, 2017.   

31

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

Extended Warranty

The Extended Warranty service fee and commission income increased 25.6% to $38.3 million for the year ended December 31, 
2018 compared with $30.5 million for the year ended December 31, 2017.  The increase in service fee and commission income is 
primarily reflective of the inclusion of PWSC for the full year of 2018 following its acquisition effective October 12, 2017.  PWSC 
service fee and commission income was $7.3 million and $2.5 million for the years ended December 31, 2018 and  December 31, 
2017, respectively.  The increase in service fee and commission income is also partially due to increases at both IWS and Trinity.  
IWS experienced increased sales of vehicle service agreements due to higher automobile sales, improved penetration at its existing 
partners and the development of new credit union relationships.  Trinity experienced increased sales to existing customers of both 
its maintenance support and warranty products, in addition to sales to new customers of its warranty products.

The Extended Warranty operating income was $4.2 million for the year ended December 31, 2018 compared with $3.7 million
for the year ended December 31, 2017.  The increase in operating income is due to the inclusion of PWSC for the full year of 
2018, as noted above, as well as increased operating income at Trinity and IWS.  The increased operating income at Trinity and 
IWS reflects improved revenues at both Trinity and IWS, partially offset by the related increases in cost of services sold at Trinity, 
claims authorized on vehicle service agreements at IWS and commissions and general and administrative expenses at both Trinity 
and IWS, for the year ended December 31, 2018 compared to the same period in 2017.

Leased Real Estate

Leased Real Estate rental income was $13.4 million for the year ended December 31, 2018 compared to $13.4 million for the year 
ended December 31, 2017.   The rental income is derived from CMC's long-term triple net lease.  The Leased Real Estate operating 
income was $2.5 million for the year ended December 31, 2018 compared to $3.1 million for the year ended December 31, 2017.  
The decrease in operating income for the year ended December 31, 2018 is due to increased legal expenses, compared to the same 
period in 2017.  Leased Real Estate recorded legal expense of $0.7 million for the year ended December 31, 2018 compared with 
zero for the year ended December 31, 2017.  Leased Real Estate operating income includes interest expense of $6.2 million and 
$6.3 million for the years ended December 31, 2018 and 2017, respectively.  See "Investments" section below for further discussion.

Net Investment Income 

Net investment income was $3.0 million in 2018 compared to $7.1 million in 2017.  The decrease in 2018 is primarily due to (i) 
the difference between the $0.2 million net investment income recorded during 2018 related to the Company’s limited liability 
investments compared to the $1.6 million net investment income recorded during 2017 related to the Company’s limited liability 
investments and (ii) the difference between the $1.2 million net investment income recorded during 2018 as a result of distributions 
received by Net Lease compared to the $4.0 million net investment income recorded during 2017 as a result of distributions received 
by Net Lease.

Net Realized (Losses) Gains 

The Company incurred net realized losses of $0.0 million in 2018 compared to net realized gains of $0.3 million in 2017.  The net 
realized losses in 2018 resulted primarily from the sale of a limited liability investment as one part of a broader set of arrangements 
with certain former officers of the Company (refer to Note 30, "Related Parties," to the Consolidated Financial Statements, for 
further discussion) offset by net realized gains recorded by Argo Holdings. The net realized gains in 2017 resulted primarily from 
the sale of a limited liability investment. 

Gain on Change in Fair Value of Equity Investments

Gain on change in fair value of equity investments was $0.4 million in 2018 compared to zero in 2017.   As further discussed in 
Note 4, "Recently Issued Accounting Standards," to the Consolidated Financial Statements, effective January 1, 2018, the Company 
adopted ASU 2016-01.  As a result, all changes in the fair value of equity investments are now recognized in net income (loss).  
The gain on change in fair value of equity investments for the year ended December 31, 2018 includes realized gains of $1.5 
million on equity investments sold during 2018 and unrealized losses of $1.1 million on equity investments held as of December 31, 
2018.  

Loss 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 $7.4 million in 2018 compared to $1.8 million in 
2017. The change from 2017 to 2018 is primarily explained by the difference between the $10.1 million fair value loss recorded 
during 2018 related to 1347 Investors compared to the $0.4 million fair value loss recorded during 2017 related to 1347 Investors.  
Limited liability investments, at fair value include the Company's investment in 26.7% of the outstanding units of 1347 Investors, 

32

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

which owns common stock in Limbach Holdings, Inc. ("Limbach"), a publicly traded company.  The Company's investment in 
1347 Investors is accounted for at fair value and reported as limited liability investments, at fair value in the consolidated balance 
sheets, with any changes in fair value to be reported in loss on change in fair value of limited liability investments, at fair value 
in the consolidated statements of operations.   As of December 31, 2018 and December 31, 2017, the carrying value of the Company's 
limited liability investment, at fair value related to 1347 Investors was $0.2 million and $10.3 million, respectively.  The fair value 
of this investment is calculated based on a model that distributes the net equity of 1347 Investors to all classes of membership 
interests.  The model uses quoted market prices and significant market observable inputs.  The most significant input to the model 
is the observed stock price of Limbach common stock, which was $13.83 on December 31, 2017 and $3.68 on December 31, 2018, 
with 75% of the decline in the Limbach common stock price occurring during the fourth quarter of 2018.  Due to the decline in 
Limbach  stock  price,  particularly  during  the  fourth  quarter  of  2018,  and  the  resulting  effect  of  the  model  on  the  Company’s 
membership interests in 1347 Investors, the Company recorded a fair value loss of $10.1 million related to its investment in 1347 
Investors for the year ended December 31, 2018 compared to a fair value loss of $0.4 million related to this investment for the 
year ended December 31, 2017.  The change between 2017 and 2018 in loss on change in fair value of limited liability investments, 
at fair value was partially offset by fair value gains of $1.5 million and $1.2 million recorded during 2018 by Argo Holdings and 
Net Lease, respectively, compared to fair value losses of $0.1 million and $1.3 million recorded during 2017 by Argo Holdings 
and Net Lease, respectively.

Net Change in Unrealized Loss on Private Company Investments

Net change in unrealized loss on private company investments was an unrealized loss of $1.6 million in 2018 compared to $0.8 
million in 2017.  The increased loss in 2018 reflects a net increase in impairments and negative fair value adjustments on private 
company investments during the year ended December 31, 2018 compared to the year ended December 31, 2017.

Interest Expense not Allocated to Segments

Interest expense not allocated to segments for 2018 was $7.4 million compared to $6.3 million in 2017.  The increase in 2018 is 
primarily attributable to generally higher London interbank offered interest rates for three-month U.S. dollar deposits ("LIBOR") 
during the year ended December 31, 2018 compared to the year ended December 31, 2017.  The Company's subordinated debt 
bears interest at the rate of LIBOR, plus spreads ranging from 3.85% to 4.20%.  The increase is also reflective of the inclusion of 
interest expense on the Company’s bank loan incurred as part of its acquisition of PWSC effective October 12, 2017. 

Other Income and Expenses not Allocated to Segments, Net

Other income and expenses not allocated to segments was a net expense of $9.0 million in 2018 compared to $10.5 million in 
2017.  The following items primarily contributed to Other income and expenses not allocated to segments, net.

Total stock-based compensation, net of forfeitures, was a benefit of $1.7 million and an expense of $1.2 million for the years ended 
December 31, 2018 and  December 31, 2017, respectively.  During the third quarter of 2018, the Company modified the terms of 
grants of restricted common stock awards to certain former officers of the Company.  Refer to Note 23, "Stock-Based Compensation," 
to the Consolidated Financial Statements, for further discussion of the restricted stock awards.  The Company also recorded $0.4 
million of payroll tax expense and $0.2 million of other expense during 2018 related to these arrangements with its former officers.

The  Company  recorded  $1.3  million  less  of  general  and  administrative  expense,  primarily  attributable  to  less  compensation, 
employee benefits and professional fees in 2018 compared to 2017.

The Company recorded a $0.7 million gain for the year ended December 31, 2017 related to the termination of a financing lease, 
as further discussed in Note 18, "Finance Lease Obligation Liability," to the Consolidated Financial Statements. 

Loss and loss adjustment expenses were an expense of $1.6 million and $0.4 million for the years ended December 31, 2018 and 
December 31, 2017, respectively, primarily as a result of unfavorable development in 2018 and 2017 due to the continuing voluntary 
run-off of Amigo.  Amigo was previously included in the Insurance Underwriting segment along with Mendota.  As a consequence 
of classifying Mendota as discontinued operations, the remaining composition of the Insurance Underwriting segment no longer 
meets  the  criteria  of  a  reportable  segment.   As  such,  all  segmented  information  has  been  restated  to  exclude  the  Insurance 
Underwriting segment for all periods presented.   The operating results of Amigo previously included in the Insurance Underwriting 
segment are now included in Other income and expenses not allocated to segments, net.

33

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

Amortization of Intangible Assets 

The Company's intangible assets with definite useful lives are amortized over their estimated useful lives.  Amortization of intangible 
assets was $2.4 million in 2018 compared to $1.1 million in 2017.  The higher amortization expense for the year ended December 31, 
2018 is related to amortization of intangible assets recorded in conjunction with the Company's acquisition of PWSC on October 
12, 2017.  During 2018, the Company finalized its fair value analysis of the assets acquired and liabilities assumed in its acquisition 
of PWSC, which resulted in the Company recording $1.4 million of amortization expense during 2018 for the period from the date 
of acquisition through December 31, 2018.  See Note 5, "Acquisition," to the Consolidated Financial Statements for further details.

Contingent Consideration Benefit 

Contingent consideration benefit was zero in 2018 compared to $0.2 million in 2017.  The benefit recorded in 2017 is attributable 
to the Company having executed an agreement with the former owner of Trinity.  The asset purchase agreement executed by the 
Company in 2013 related to the acquisition of Trinity provided for additional payments to the former owner of Trinity contingent 
upon the achievement of certain targets over future reporting periods. 

Loss on Change in Fair Value of Debt 

The loss on change in fair value of debt amounted to $1.7 million in 2018 compared to $8.5 million in 2017.  The loss for 2018
reflects an increase in the fair value of the subordinated debt resulting from changes in inputs, other than the instrument-specific 
credit risk, to the Company’s fair value model.  The loss for 2017 reflects an increase in the fair value of the subordinated debt  
resulting from changes in all of the inputs to the Company’s fair value model.  As further discussed in Note 4, "Recently Issued 
Accounting Standards," to the Consolidated Financial Statements, effective January 1, 2018, the Company adopted ASU 2016-01.  
As a result, the portion of the change in fair value of subordinated debt related to the instrument-specific credit risk is now recognized 
in other comprehensive income (loss), whereas for 2017, the total change in fair value of subordinated debt was recorded in net 
income (loss).  See "Debt" section below for further information.  

Gain on Disposal of Subsidiary 

On June 1, 2018, the Company disposed of its subsidiary, Itasca Real Estate Investors, LLC.  As a result of the disposal, the 
Company recognized a gain of $0.0 million during the year ended December 31, 2018. 

Equity in Net (Loss) Income of Investee

Equity in net loss of investee was $2.5 million in 2018 compared to equity in net income of investee of $2.1 million in 2017.  
Equity in net (loss) income of investee represents the Company's investment in Itasca Capital Ltd.  See Note 9, "Investment in 
Investee," to the Consolidated Financial Statements, for further discussion. 

Income Tax Expense (Benefit) 

Income tax expense for 2018 was $0.3 million compared to income tax benefit of $16.7 million in 2017.  The 2018 income tax 
expense is primarily related to the change in unrecognized tax benefits and state income taxes.

The 2017 income tax benefit is primarily related to a release of deferred income tax liabilities and an adjustment to the deferred 
income tax valuation allowance resulting from the Tax Cuts and Jobs Act (the "Tax Act") enacted on December 22, 2017.  The 
Tax Act made broad and complex changes to the U.S. tax code, including, but not limited to, a permanent reduction in the U.S. 
federal corporate income tax rate to 21%.

The Company is subject to the provisions of Accounting Standards Codification 740-10, Income Taxes, which requires that the 
effect on deferred tax income assets and liabilities of a change in tax rates be recognized in the period the tax rate change was 
enacted. In December of 2017, the SEC staff issued Staff Accounting Bulletin 118 ("SAB 118"), which provides that companies 
that have not completed their accounting for the effects of the Tax Act but can determine a reasonable estimate of those effects 
should include a provisional amount based on their reasonable estimate in their financial statements.

Pursuant to SAB 118, the Company recorded provisional amounts for the estimated income tax effects of the Tax Act on deferred 
income taxes.  The Company recorded a $18.1 million decrease to income tax expense in the consolidated statements of operations 
for the year ended December 31, 2017, $18.0 million of which related to a decrease in the Company’s net deferred income tax 
liability as of December 31, 2017 because of the reduction in the corporate income tax rate. 

Although the $18.1 million tax benefit represented what the Company believed was a reasonable estimate of the income tax effects 
of the Tax Act on the Company’s Consolidated Financial Statements as of December 31, 2017, it was considered provisional.  In 

34

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

the fourth quarter of 2018, the Company finalized its calculation of the income tax effects of the Tax Act on its deferred income 
taxes by recording an additional tax benefit of $0.1 million.

See Note 21, "Income Taxes," to the Consolidated Financial Statements, for additional detail of the income tax expense (benefit) 
recorded for the years ended December 31, 2018 and December 31, 2017, respectively.

35

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

INVESTMENTS

As a result of classifying Mendota as discontinued operations, the results of their operations are reported separately for all periods 
presented and their assets are presented as held for sale in the consolidated balance sheets at December 31, 2017.  All investment 
information in the section below has been restated to exclude Mendota for all periods presented.  

Portfolio Composition

All of our investments in fixed maturities are classified as available-for-sale and are reported at fair value.  All of our equity 
investments are reported at fair value.  Prior to the adoption of ASU 2016-01, equity investments were considered available-for-
sale.  All of our 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 Company's investment in 1347 Investors LLC as well as the underlying investments of the 
Company’s consolidated entities Net Lease and Argo Holdings.  Investments in private companies consist of common stock, 
preferred  stock,  notes  receivable  and  derivative  contracts  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.  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, 2018, we held cash and cash equivalents, restricted cash and investments with a carrying value of $91.5 million.  

Investments held by our insurance subsidiary, Amigo, must comply with domiciliary state regulations that prescribe the type, 
quality and concentration of investments.  Our U.S. operations typically invest in U.S. dollar-denominated instruments to mitigate 
their exposure to currency rate fluctuations. 

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

36

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

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

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

2018

% of Total

2017

% of Total

5,547

607

3,186

2,920

6.1%

0.6%

3.5%

3.2%

5,612

626

2,876

5,427

5.6%

0.6%

2.9%

5.4%

12,260

13.4%

14,541

14.5%

801

55

856

4,790

26,015

3,090

10,662

2,079

152

59,904

14,619

16,959

91,482

0.9%

—%

0.9%

5.2%

28.4%

3.4%

11.7%

2.3%

0.2%

65.5%

16.0%

18.5%

3,570

1,019

4,589

9,094

32,211

4,870

10,662

3,721

151

79,839

5,377

14,985

3.6%

1.0%

4.6%

9.1%

32.1%

4.9%

10.6%

3.7%

0.2%

79.7%

5.4%

14.9%

100.0%

100,201

100.0%

The Company performs a quarterly impairment analysis of its investments classified as available-for-sale and investments in private 
companies.  Prior to the adoption of ASU 2016-01, equity investments were considered available-for-sale and were included in 
the analysis of other-than-temporary impairments.  Following the adoption of ASU 2016-01 beginning with the first quarter of 
2018, the Company includes only its investments in fixed maturities and investments in private companies in its quarterly impairment 
analysis.    Further  information  regarding  our  detailed  analysis  and  factors  considered  in  establishing  an  other-than-temporary 
impairment on an available-for-sale investment is discussed within the "Critical Accounting Estimates and Assumptions" section 
of MD&A. 

As a result of the analysis performed by the Company to determine declines in market value that are other-than-temporary, there 
were no write downs for other-than-temporary impairment related to available-for-sale investments recorded for the years ended 
December 31, 2018 and December 31, 2017.    As a result of the analysis performed with respect to limited liability investments, 
at fair value, the Company recorded impairments of $0.1 million and $0.1 million for the years ended December 31, 2018 and 
December 31, 2017, respectively, which are included in loss on change in fair value of limited liability investments, at fair value 
in the consolidated statements of operations.  As a result of the analysis performed with respect to investments in private companies, 
the Company recorded impairments of $1.0 million and $2.0 million for the years ended December 31, 2018 and December 31, 
2017,  respectively,  which  are  included  in  net  change  in  unrealized  loss  on  private  company  investments  in  the  consolidated 
statements of operations.

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 

37

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

with recapture of principal, the Company may elect to sell a fixed maturity investment at a loss.  Prior to the adoption of ASU 
2016-01, the Company considered the ability and intent to hold an equity investment for a period of time sufficient to allow for 
anticipated recovery.  

At December 31, 2018, the gross unrealized losses for fixed maturities amounted to $0.2 million, and there were no unrealized 
losses attributable to non-investment grade fixed maturities.  At December 31, 2017, the gross unrealized losses for fixed maturities 
and equity investments amounted to $0.8 million, and there were no unrealized losses attributable to non-investment grade fixed 
maturities.  At each of December 31, 2018 and December 31, 2017, all unrealized losses on individual investments were considered 
temporary. 

38

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

UNPAID LOSS AND LOSS ADJUSTMENT EXPENSES

As a result of classifying Mendota as discontinued operations, the results of their operations are reported separately for all periods 
presented and their liabilities are presented as held for sale in the consolidated balance sheets at December 31, 2017.  All unpaid 
loss and loss adjustment expenses information in the section below has been restated to exclude Mendota for all periods presented. 

Unpaid loss and loss adjustment expenses represent the estimated liabilities for reported loss events, IBNR loss events and the 
related estimated loss adjustment expenses. 

Tables 3 and 4 present distributions, by line of business, of the provision for unpaid loss and loss adjustment expenses gross and 
net of external reinsurance, respectively.  

TABLE 3    Provision for unpaid loss and loss adjustment expenses - gross
As of December 31 (in thousands of dollars)

Line of Business

Non-standard automobile

Commercial automobile

Other
Total

2018

686

794

593
2,073

TABLE 4    Provision for unpaid loss and loss adjustment expenses - net of reinsurance recoverable
As of December 31 (in thousands of dollars)

Line of Business

Non-standard automobile

Commercial automobile

Other

Total

Non-Standard Automobile

2018

686

794

593

2,073

2017

572

580

177
1,329

2017

508

572

177

1,257

At December 31, 2018 and December 31, 2017, the gross provisions for unpaid loss and loss adjustment expenses for our non-
standard automobile business were $0.7 million and $0.6 million, respectively.  The increase is due to an increase in unpaid loss 
and loss adjustment expenses at Amigo.

Commercial Automobile

At December 31, 2018 and December 31, 2017, the gross provisions for unpaid loss and loss adjustment expenses for our commercial 
automobile business were $0.8 million and $0.6 million, respectively.  This increase is due to an increase in unpaid loss and loss 
adjustment expenses at Amigo. 

Other

At December 31, 2018 and December 31, 2017, the gross provisions for unpaid loss and loss adjustment expenses for our other 
business were $0.6 million and $0.2 million, respectively.  The increase is due to an increase in unpaid loss adjustment expenses 
at Amigo.

Information with respect to development of our provision for prior years' loss and loss adjustment expenses is presented in Table 
5.  

39

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

TABLE 5 Increase in prior years' provision for loss and loss adjustment expenses
For the years ended December 31 (in thousands of dollars)

Unfavorable change in provision for loss and loss adjustment expenses for
prior accident years

2018

1,631

2017

401

The net movements in prior years' provisions for loss and loss adjustment expenses, net of reinsurance, was an increase of $1.6 
million  and  $0.4  million,  respectively,  for  the  years  ended  December 31,  2018  and  December  31,  2017.    The  unfavorable 
development in 2018 and 2017 was related to an increase in loss and loss adjustment expenses due to the continuing voluntary 
run-off of Amigo.  Original estimates are increased or decreased as additional information becomes known regarding individual 
claims. 

DEBT

Bank Loan

On October 12, 2017, the Company borrowed a principal amount of $5.0 million from a bank to partially finance its acquisition 
of PWSC.  The bank loan matures on October 12, 2022 and has a fixed interest rate of 5.0%.  The bank loan is carried in the 
consolidated balance sheets at its unpaid principal balance. 

Notes Payable

As part of its acquisition of CMC in July 2016, the Company assumed the Mortgage and recorded the Mortgage at its estimated 
fair value of $191.7 million, which included the unpaid principal amount of $180.0 million as of the date of acquisition plus a 
premium of $11.7 million.  The Mortgage matures on May 15, 2034 and has a fixed interest rate of 4.07%.  The Mortgage 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 premium using the effective interest rate method. 

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 matures on December 10, 2031 and has a fixed interest rate of 4.81%.  
The Flower Note is carried in the consolidated balance sheets at its unpaid principal balance. 

On October 15, 2015, Net Lease assumed a $9.0 million mezzanine debt in conjunction with the purchase of investment real estate 
properties ("the Net Lease Note").  The Net Lease Note matures on November 1, 2020 and has a fixed interest rate of 10.25%.  
The Net Lease Note is carried in the consolidated balance sheets at its unpaid principal balance. 

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, 2018, deferred interest payable of $2.5 million is included in accrued expenses and 
other liabilities in the consolidated balance sheets. 

The  Company's  subordinated  debt  is  measured  and  reported  at  fair  value.   At  December 31,  2018,  the  carrying  value  of  the 
subordinated debt is $50.0 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 29, "Fair Value of Financial Instruments," to the Consolidated 
Financial Statements.  

During the year ended December 31, 2018, the market observable swap rates changed, and the Company experienced an increase 
in the credit spread assumption developed by the third-party.  Changes in the market observable swap rates affect the fair value 

40

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

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 2018, along with the passage of time, contributed to the $2.1 million decrease in fair value of the 
Company’s subordinated debt between December 31, 2017 and December 31, 2018. 

As  further  discussed  in  Note  4,  "Recently  Issued Accounting  Standards,"  to  the  Consolidated  Financial  Statements,  effective 
January 1, 2018, the Company adopted ASU 2016-01.  As a result, the portion of the change in fair value of subordinated debt 
related to the instrument-specific credit risk is now recognized in other comprehensive income (loss), whereas for 2017, the total 
change in fair value of subordinated debt was recorded in net income (loss).  Of the $2.1 million decrease in fair value of the 
Company’s subordinated debt between December 31, 2017 and December 31, 2018, $3.8 million is reported as decrease in fair 
value of debt attributable to instrument-specific credit risk in the Company's consolidated statements of comprehensive loss and 
$1.7 million is reported as loss on change in fair value of debt in the Company’s consolidated statements of operations. 

Also as a result of the adoption of ASU 2016-01, a cumulative $40.5 million change in fair value of subordinated debt attributable 
to instrument-specific credit risk was reclassified from accumulated deficit to accumulated other comprehensive income (loss) as 
of January 1, 2018.  As long as the Company repays its subordinated debt at maturity, it can be expected that this $40.5 million
reclassification will reverse without being reported 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 will no longer 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 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.

For a description of each of the Company's six subsidiary trusts, see Note 17, "Debt," to the Consolidated Financial Statements.  

Pursuant to indentures governing the Company’s outstanding bank loan, subordinated debt and a bank loan associated with the 
Company’s acquisition on March 1, 2019, described more fully in Note 34, "Subsequent Event," to the Consolidated Financial 
Statements, the Company is obligated to deliver audited financial statements for certain of its subsidiaries as of and for the year 
ended December 31, 2018.  Due to the delay in filing its 2018 Annual Report, the Company has been unable to meet these obligations, 
the failure of which could be declared events of default under the respective indentures.  As of the date of the filing of its 2018
Annual Report, none of the lenders or trustees responsible for administering any of our outstanding debt has declared an event of 
default, if required by the applicable indenture, notified us of an intent to accelerate any portion of the outstanding debt or charge 
default interest thereon, or pursued any other remedies available to it.  Were any of these lenders or trustees to declare an event of 
default, the Company would have a period of time to cure the default.  Now that the Company has filed its 2018 Annual Report, 
the  Company  expects  to  be  in  a  position  to  deliver  to  the  trustees  the  requisite  audited  financial  statements  for  certain  of  its 
subsidiaries as of and for the year ended December 31, 2018.

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 been met primarily by funds generated from 
operations, capital raising, disposal of discontinued operations, investment maturities and income and other returns received on 
investments or from the sale of investments.  Cash provided from these sources is used primarily for making investments and for 
loss and loss adjustment expense payments, debt servicing and other operating expenses. The timing and amount of payments for 
loss and loss adjustment expenses may differ materially from our provisions for unpaid loss and loss adjustment expenses, which 
may create increased liquidity requirements. 

41

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

Cash Flows from Continuing Operations

During 2018, the Company reported on the consolidated statements of cash flows $2.8 million of net cash used in operating 
activities from continuing operations.  The reconciliation between the Company's reported net loss of $28.3 million and the $2.8 
million of net cash used in operating activities from continuing operations can be explained primarily by the $7.1 million loss on 
disposal of discontinued operations, the $7.4 million loss on change in fair value of limited liability investments, at fair value, $6.7 
million of depreciation and amortization expense, the increase in deferred service fees of $6.0 million and the $2.5 million of 
equity in net loss of investee, partially offset by the $2.3 million increase in other receivables.

During 2018, the net cash provided by investing activities from continuing operations as reported on the consolidated statements 
of cash flows was $18.1 million.  This source of cash was driven primarily by net proceeds from the sale of discontinued operations, 
in  addition  to  proceeds  from  sales  and  maturities  of  fixed  maturities,  equity  investments,  limited  liability  investments,  other 
investments and investee in excess of purchases of fixed maturities, equity investments and limited liability investments, at fair 
value.

During 2018, the net cash used in financing activities from continuing operations as reported on the consolidated statements of 
cash flows was $4.1 million.  This use of cash is primarily attributed to principal repayments of $3.4 million on notes payable and 
$1.0 million on the bank loan.

In summary, as reported on the consolidated statements of cash flows, the Company's net increase in cash and cash equivalents  
and restricted cash from continuing operations during 2018 was $11.2 million.  The absence of cash flows from discontinued 
operations, whether positive or negative, is not expected to adversely affect the Company’s future liquidity and capital resources 
given that the discontinued operations are comprised of insurance subsidiaries formerly reported as part of the Company’s Insurance 
Underwriting segment.  Receipt of dividends from the Company's insurance subsidiaries has not generally been considered a 
source of liquidity for the holding company.  The insurance subsidiaries have required regulatory approval for the return of capital 
and, in certain circumstances, prior to the payment of dividends.  At December 31, 2018, Amigo was restricted from making any 
dividend payments to the holding company without regulatory approval pursuant to domiciliary state insurance regulations.

The Company's Extended Warranty subsidiaries fund their obligations primarily through service fee and commission income.  The 
Company's Leased Real Estate subsidiary funds its obligations through rental income.  The Company's insurance subsidiaries fund 
their obligations primarily through investment income and maturities in the investments portfolios.  

The liquidity of the holding company is managed separately from its subsidiaries.  Actions available to the holding company to 
raise liquidity in order to meet its obligations include the sale of passive investments; sale of subsidiaries; issuance of debt or 
equity securities; distributions from the Company’s Extended Warranty subsidiaries, as further described below; and giving notice 
to its Trust Preferred trustees of its intention to exercise its voluntary right to defer interest payments for up to 20 quarters on the 
six subsidiary trusts of the Company’s subordinated debt, which right the Company exercised during the third quarter of 2018.

Subsequent to December 31, 2018, the Company announced it had closed on the acquisition of Geminus Holding Company, Inc. 
("Geminus"), a specialty, full-service provider of vehicle service contracts and other finance and insurance products offered through 
its subsidiaries, The Penn Warranty Corporation ("Penn") and Prime Auto Care, Inc. ("Prime").  Geminus, Penn and Prime will 
be included in Extended Warranty.  Related to the Geminus acquisition, the Company secured $10.0 million of acquisition financing 
(the "Financing").  IWS, Trinity, Geminus, Penn and Prime are borrowers under the Financing.  Pursuant to satisfying the covenants 
under the Financing, IWS, Trinity, Geminus, Penn and Prime are permitted to make distributions to the holding company in an 
aggregate amount not to exceed $1.5 million in any 12-month period.  Separately, pursuant to covenants under the bank loan 
secured to partially finance the acquisition of PWSC on October 12, 2017, PWSC is not permitted to make distributions to the 
holding company without the consent of the lender.

Dividends from the Leased Real Estate segment are not generally considered a source of liquidity for the holding company.   Because 
of the Lease Amendment, CMC may be in a position to distribute to the Company some of the cash received from the additional 
rental income.  Any material cash flow to the Company, however, to help the Company meet its holding company obligations 
remains likely to occur only upon the occurrence of one of the three events described in the next paragraph that would trigger 
payment of service fees. There can be no assurance as to the timing of the occurrence, or the resulting outcome, from one of these 
events.    

Pursuant to the terms of the management services agreement entered into at the closing of the acquisition of CMC, an affiliate of 
the seller (the "Service Provider") will provide certain services to CMC and its subsidiaries in exchange for service fees.  Such 
services (collectively, the "Services") will include (i) causing an affiliate of the Service Provider to guaranty certain obligations 
of the Property Owner (pursuant to an Indemnity and Guaranty Agreement between such affiliate and the holder of the Mortgage 

42

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

(the "Mortgagor")), (ii) providing certain individuals to serve as members of the board of directors and/or certain executive officers 
of CMC and/or its subsidiaries and (iii) providing asset management services with respect to the Real Property.  In exchange for 
the Services, the Property Owner will pay certain fees to the Service Provider.  The payment of such service fees may be triggered 
by (i) a sale of the Real Property, (ii) a restructuring of the lease to which the Real Property is subject or (iii) a refinancing or 
restructuring of the Mortgage.  The amount of the service fees will range from 40%-80% of the net proceeds generated by the 
event triggering the payment of the service fees (depending on the nature and timing of the triggering event).  The Lease Amendment 
has not triggered the payment of service fees to the Service Provider.

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 $1.9 million and $0.6 million at December 31, 2018 and December 31, 2017, respectively.  These 
amounts are reflected in the cash and cash equivalents of $14.6 million and $5.4 million reported at December 31, 2018 and 
December 31, 2017, respectively, on the Company’s consolidated balance sheets.  The cash and cash equivalents and restricted 
cash other than the holding company’s liquidity represent restricted and unrestricted cash held by Amigo, Kingsway Re and the 
Company's Extended Warranty and Leased Real Estate subsidiaries and are not considered to be available to meet holding company 
obligations, which primarily consist of holding company operating expenses; transaction-related expenses; investments; and any 
other extraordinary demands on the holding company. 

The holding company’s liquidity of $1.9 million at December 31, 2018 represented approximately four months of regularly recurring 
operating expenses before any transaction-related expenses, any new holding company investments or any other extraordinary 
demands on the holding company.  As of the filing date of the Company’s 2018 Annual Report, the holding company’s liquidity 
of $1.5 million represented approximately three months of regularly recurring operating expenses before any transaction-related 
expenses, any new holding company investments or any other extraordinary demands on the holding company.  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.  As a result of this action, the projected cash obligations of the holding company over the next 12 months have 
been reduced by approximately $6.4 million, calculated by holding constant the most recent coupon for each of the six subsidiary 
trusts of the Company’s subordinated debt.

The holding company’s liquidity of $1.9 million at December 31, 2018 and $1.5 million as of the filing date of the Company’s 
2018 Annual Report represents only actual cash on hand and does not include cash that would be made available to the holding 
company  from  the  sale  of  investments  owned  by  the  holding  company  or  the  distribution  of  cash  by  the  Extended Warranty 
subsidiaries as described above.  While these sources do not represent cash of the holding company as of the filing date of the 
Company’s 2018 Annual Report, they do represent future sources of liquidity that make it probable that the holding company will 
be able to meet its obligations as they become due over the next 12 months.

While the Company believes it has sources of liquidity available to allow it to continue to meet its holding company obligations, 
there can be no assurance that such sources of liquidity will be available when needed.

Regulatory Capital

In  the  United  States,  a  risk-based  capital  ("RBC")  formula  is  used  by  the  National Association  of  Insurance  Commissioners 
("NAIC") to identify property and casualty insurance companies that may not be adequately capitalized.  In general, insurers 
reporting surplus as regards policyholders below 200% of the authorized control level, as defined by the NAIC, at December 31 
are subject to varying levels of regulatory action, including discontinuation of operations.  As of December 31, 2018, surplus as 
regards policyholders reported by Amigo exceeded the 200% threshold.

During the fourth quarter of 2012, the Company began taking steps to place all of Amigo into voluntary run-off.  As of December 
31, 2012, Amigo’s  RBC was 157%.  In April 2013, Kingsway  filed a comprehensive run-off  plan with the Florida Office of 
Insurance Regulation, which outlines plans for Amigo's run-off.  Amigo remains in compliance with that plan.  As of December 31, 
2018, Amigo's RBC was 1,905%.  

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,  2018,  the  capital  maintained  by  Kingsway  Re  was  in  excess  of  the  regulatory  capital 
requirements in Barbados.

43

KINGSWAY FINANCIAL SERVICES INC.
Management's Discussion and Analysis

CONTRACTUAL OBLIGATIONS

Table 6 summarizes cash disbursements related to the Company's contractual obligations projected by period, including debt 
maturities, interest payments on outstanding debt, the provision for unpaid loss and loss adjustment expenses and future minimum 
payments under operating leases.  Interest payments in Table 6 related to the subordinated debt assume LIBOR remains constant 
throughout the projection period.

Our provision for unpaid loss and loss adjustment expenses does not have contractual payment dates.  In Table 6 below, we have 
included a projection of when we expect our unpaid loss and loss adjustment expenses to be paid, based on historical payment 
patterns.  The exact timing of the payment of unpaid loss and loss adjustment expenses cannot be predicted with certainty.  We 
maintain a substantial amount in short-term investments to provide adequate cash flows for the projected payments in Table 6.  
The unpaid loss and loss adjustment expenses in Table 6 have not been reduced by amounts recoverable from reinsurers.

TABLE 6 Cash payments related to contractual obligations projected by period 
As of December 31, 2018 (in thousands of dollars)

Bank loan

Notes payable

Subordinated debt

Interest payments on outstanding debt

Unpaid loss and loss adjustment expenses

Future minimum lease payments

2019

1,000

3,768

—

8,449

1,272

976

2020

1,000

13,164

—

8,158

372

380

2021

1,000

4,582

—

7,080

285

390

2022

917

5,023

—

2023 Thereafter

—

—

Total

3,917

5,489

157,897

189,923

—

90,500

90,500

6,831

46,473

110,851

187,842

96

398

38

421

10

883

2,073

3,448

Total

15,465

23,074

13,337

13,265

52,421

360,141

477,703

Table 6 above does not reflect amounts that may be paid for the redemption of the 222,876 shares of Class A preferred stock 
("Preferred  Shares")  outstanding  at  December 31,  2018.    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 April 1, 2021 (the "Redemption Date").  
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 Redemption 
Date.  The total redemption amount of the Preferred Shares as of the Redemption Date if the Preferred Shares are not converted 
is expected to be $8.2 million.  The timing and amount of cash, if any, to be paid by the Redemption Date will be based upon the 
extent, if at all, that the Company exercises its right to redeem any Preferred Shares prior to the Redemption Date or the holders 
of the Preferred Shares exercise their option to convert any of the Preferred Shares to common shares.

Refer to Note 25, "Redeemable Class A Preferred Stock," to the Consolidated Financial Statements for further information regarding 
the Preferred Shares.

OFF-BALANCE SHEET ARRANGEMENTS

The Company has off-balance sheet arrangements related to guarantees, which are further described in Note 31, "Commitments 
and Contingent Liabilities," to the Consolidated Financial Statements. 

44

KINGSWAY FINANCIAL SERVICES INC.

Item 7A. Quantitative and Qualitative Disclosures About Market Risk 

Market Risk

Market risk is the risk that we will incur losses due to adverse changes in interest or currency exchange rates and equity prices.  
We have exposure to market risk through our investment activities and our financing activities.

Given our U.S. operations typically invest in U.S. dollar denominated fixed maturity instruments, our primary market risk exposures 
in the investments portfolio are to changes in interest rates.  Periodic changes in interest rate levels generally affect our financial 
results to the extent that the investments are recorded at market value and reinvestment yields are different than the original yields 
on maturing instruments.  During periods of rising interest rates, the market values of the existing fixed maturities will generally 
decrease.  The reverse is true during periods of declining interest rates.

We manage our exposure to risks associated with interest rate fluctuations through active review of our investment portfolio by 
our management and Board of Directors, consultation with third-party financial advisors and by managing the maturity profile of 
our fixed maturity portfolio.  Our goal is to maximize the total after-tax return on all of our investments.  An important strategy 
we employ to achieve this goal is to try to hold enough in cash and short-term investments in order to avoid liquidating longer-
term investments to pay claims authorized on vehicle service agreements and loss and loss adjustment expenses.

Table  7  below  summarizes  the  fair  value  by  contractual  maturities  of  the  fixed  maturities  portfolio,  excluding  cash  and  cash 
equivalents, at December 31, 2018 and December 31, 2017.

TABLE 7 Fair value of fixed maturities by contractual maturity date
As of December 31 (in thousands of dollars, except for percentages)

Due in less than one year

Due in one through five years

Due after five through ten years

Due after ten years

Total

2018

5,445

5,233

210

1,372

12,260

% of Total

44.4%

42.7%

1.7%

11.2%

100.0%

2017

3,605

9,310

345

1,281

14,541

% of Total

24.8%

64.0%

2.4%

8.8%

100.0%

At December 31, 2018, 87.1% of fixed maturities, including treasury bills, government bonds and corporate bonds, had contractual 
maturities of five years or less.  Actual maturities may differ from contractual maturities because certain issuers have the right to 
call or prepay obligations with or without call or prepayment penalties.  The Company holds cash and high-grade short-term assets 
that, along with fixed maturities, management believes are sufficient in amount for the payment of unpaid loss and loss adjustment 
expenses and other obligations on a timely basis.  In the event additional cash is required to meet obligations to our policyholders 
and customers, we believe that the high-quality investments in the portfolios provide us with sufficient liquidity.

Based upon the results of interest rate sensitivity analysis, Table 8 below shows the interest rate risk of our investments in fixed 
maturities, measured in terms of fair value (which is equal to the carrying value for all our fixed maturity securities), at December 31, 
2018 and December 31, 2017.

TABLE 8 Sensitivity analysis on fixed maturities 
As of December 31 (in thousands of dollars)

As of  December 31, 2018

Estimated fair value

Estimated increase (decrease) in fair value

As of  December 31, 2017

Estimated fair value

Estimated increase (decrease) in fair value

100 Basis Point
Decrease in
Interest Rates

No Change

100 Basis Point
Increase in
Interest Rates

$

$

$

$

12,436

176

14,840

299

$

$

$

$

12,260

$

— $

12,084
(176)

14,541

$

— $

14,242
(299)

45

KINGSWAY FINANCIAL SERVICES INC.

We use both fixed and variable rate debt as sources of financing.  Because our subordinated debt is LIBOR-based, our primary 
market risk related to financing activities is to changes in LIBOR.  As of December 31, 2018, each one hundred basis point increase 
in LIBOR would result in an approximately $0.9 million increase in our annual interest expense.

Equity Risk

Equity risk is the risk we will incur economic losses due to adverse changes in equity prices.  Our exposure to changes in equity 
prices  results  from  our  holdings  of  common  stock.    We  principally  manage  equity  price  risk  through  industry  and  issuer 
diversification and asset allocation techniques and by continuously evaluating market conditions.

Credit Risk

Credit risk is defined as the risk of financial loss due to failure of the other party to a financial instrument to discharge an obligation.  
Credit risk arises from our positions in short-term investments, corporate debt instruments and government bonds.

The Investment Committee of the Board of Directors is responsible for the oversight of key investment policies and limits.  These 
policies and limits are subject to annual review and approval by the Investment Committee.  The Investment Committee is also 
responsible for ensuring these policies are implemented and procedures are in place to manage and control credit risk.

Table  9  below  summarizes  the  composition  of  the  fair  values  of  fixed  maturities,  excluding  cash  and  cash  equivalents,  at 
December 31, 2018 and December 31, 2017 by rating as assigned by Standard and Poor's ("S&P") or Moody's Investors Service 
("Moody's").    Fixed  maturities  consist  of  predominantly  high-quality  instruments  in  corporate  and  government  bonds  with 
approximately 99.0% of those investments rated 'A' or better at December 31, 2018.  'Not Rated' in Table 9 below at December 
31, 2017 represents $3.0 million of 8% preferred stock of 1347 Property Insurance Holdings, Inc., redeemable on February 24, 
2020.  During the first quarter of 2018, the preferred stock was redeemed at its par value of $3.0 million. 

TABLE 9 Credit ratings of fixed maturities 
As of December 31 (ratings as a percentage of total fixed maturities)

Rating (S&P/Moody's)

AAA/Aaa

AA/Aa

A/A

Percentage rated A/A2 or better

BBB/Baa

BB/Ba

Not rated

Total

2018

72.0%

16.1

10.9

99.0%

1.0

—

—

2017

59.6%

8.8

10.9

79.3%

—

—

20.7

100.0%

100.0%

46

KINGSWAY FINANCIAL SERVICES INC.

Item 8.   Financial Statements and Supplementary Data.

Index to the Consolidated Financial Statements of

Kingsway Financial Services Inc.

Reports of Independent Registered Public Accounting Firms
Consolidated Balance Sheets at December 31, 2018 and 2017
Consolidated Statements of Operations for the Years Ended December 31, 2018 and 2017
Consolidated Statements of Comprehensive Loss for the Years Ended December 31, 2018 and 2017
Consolidated Statements of Shareholders' Equity for the Years Ended December 31, 2018 and 2017
Consolidated Statements of Cash Flows for the Years Ended December 31, 2018 and 2017
Notes to the Consolidated Financial Statements

Note 1-Business
Note 2-Summary of Significant Accounting Policies
Note 3-Restatement of Previously Issued Financial Statements
Note 4-Recently Issued Accounting Standards
Note 5-Acquisition
Note 6-Disposal, Discontinued Operations and Liquidation
Note 7-Variable Interest Entities
Note 8-Investments
Note 9-Investment in Investee
Note 10-Reinsurance
Note 11-Deferred Acquisition Costs
Note 12-Goodwill
Note 13-Intangible Assets
Note 14-Property and Equipment
Note 15-Vehicle Service Agreement Liability
Note 16-Unpaid Loss and Loss Adjustment Expenses
Note 17-Debt
Note 18-Finance Lease Obligation Liability
Note 19-Leases
Note 20-Revenue from Contracts with Customers
Note 21-Income Taxes
Note 22-Loss from Continuing Operations per Share
Note 23-Stock-Based Compensation
Note 24-Employee Benefit Plan
Note 25-Redeemable Class A Preferred Stock
Note 26-Shareholders' Equity
Note 27-Accumulated Other Comprehensive Income (Loss)
Note 28-Segmented Information
Note 29-Fair Value of Financial Instruments
Note 30-Related Parties
Note 31-Commitments and Contingent Liabilities
Note 32-Regulatory Capital Requirements and Ratios
Note 33-Statutory Information and Policies
Note 34-Subsequent Event

47

48
50
51
52
53
54
56
56
56
62
70
71
72
74
77
82
83
83
83
84
85
85
86
91
93
93
94
96
99
99
102
103
103
104
106
108
114
119
120
120
121

KINGSWAY FINANCIAL SERVICES INC.

Report of Independent Registered Public Accounting Firm

To the Shareholders and the Board of Directors of Kingsway Financial Services Inc.

Opinion on the Financial Statements
We have audited the accompanying consolidated balance sheet of Kingsway Financial Services Inc. and its subsidiaries (the 
Company) as of December 31, 2018, the related consolidated statements of operations, comprehensive loss, shareholders’ 
equity and cash flows for the year then ended, and the related notes to the consolidated financial statements and schedules 
(collectively, the financial statements). In our opinion, the financial statements present fairly, in all material respects, the 
financial position of the Company as of December 31, 2018, and the results of its operations and its cash flows for the year 
then ended, in conformity with accounting principles generally accepted in the United States of America.

Basis for Opinion
These financial statements are the responsibility of the Company’s management. Our responsibility is to express an opinion 
on the Company’s financial statements based on our audit. 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  U.S.  federal  securities  laws  and  the  applicable  rules  and  regulations  of  the  Securities  and  Exchange 
Commission and the PCAOB.

We conducted our audit in accordance with the standards of the PCAOB. Those standards require that we plan and perform 
the audit to obtain reasonable assurance about whether 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 audit 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 audit 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 audit 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 audit provides a reasonable basis for our opinion.

/s/ RSM US LLP

We have served as the Company's auditor since 2019.

Chicago, Illinois
February 27, 2020

48

KINGSWAY FINANCIAL SERVICES INC.

Report of Independent Registered Public Accounting Firm

Board of Directors and Shareholders
Kingsway Financial Services Inc.
Itasca, Illinois

Opinion on the Consolidated Financial Statements 

We  have  audited  the  accompanying  consolidated  balance  sheet  of  Kingsway  Financial  Services  Inc.  and  subsidiaries  (the 
“Company”) as of December 31, 2017 and the related consolidated statements of operations, comprehensive loss, shareholders’ 
equity, and cash flows for the year then ended, and the related notes and schedules (collectively referred to as the “consolidated 
financial statements”). In our opinion, the consolidated financial statements present fairly, in all material respects, the financial 
position of the Company at December 31, 2017 and the results of its operations and its cash flows for the year then ended, in 
conformity with accounting principles generally accepted in the United States of America.

Restatement

As discussed in Note 3 to the consolidated financial statements, the 2017 financial statements have been restated to correct 
misstatements.

Basis for Opinion

These consolidated financial statements are the responsibility of the Company’s management. Our responsibility is to express an 
opinion on the Company’s consolidated financial statements based on our audit. 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 audit in accordance with the standards of the PCAOB. Those standards require that we plan and perform the 
audit to obtain reasonable assurance about whether the consolidated financial statements are free of material misstatement, whether 
due to error or fraud.

Our audit included performing procedures to assess the risks of material misstatement of the consolidated 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  consolidated  financial  statements.  Our  audit  also  included 
evaluating  the  accounting  principles  used  and  significant  estimates  made  by  management,  as  well  as  evaluating  the  overall 
presentation of the consolidated financial statements. We believe that our audit provides a reasonable basis for our opinion.

/s/ BDO USA, LLP

We served as the Company's auditor from 2010 to 2018.

Grand Rapids, Michigan

March 16, 2018, except for Notes 3, 6 and 28, as to which the date is February 27, 2020

BDO USA, LLP, a Delaware limited liability partnership, is the U.S. member of BDO International Limited, a UK company limited by guarantee, and forms part of the international BDO network of independent 
member firms.

BDO is the brand name for the BDO network and for each of the BDO Member Firms.

49

KINGSWAY FINANCIAL SERVICES INC.

Consolidated Balance Sheets 
(in thousands, except share data)

December 31, 2018

December 31, 2017

(restated)

Assets

Investments:

Fixed maturities, at fair value (amortized cost of $12,432 and $14,707, respectively)

$

12,260

$

856

4,790

26,015

3,090

10,662

2,079

152

59,904

14,619

16,959

951

420

3,434

9,523

6,904

103,142

74,659

83,266

4,459

—

378,240

$

14,786

$

2,400

47,130

2,073

3,917

199,316

50,023

28,537

—

348,182

$

$

Equity investments, at fair value (cost of $2,274 and $4,868, 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 $10,225 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

Investment in investee

Accrued investment income

Service fee receivable, net of allowance for doubtful accounts of $191 and $318, respectively

Other receivables, net of allowance for doubtful accounts of $184 and zero, respectively

Deferred acquisition costs, net

Property and equipment, net of accumulated depreciation of $15,958 and $11,683, respectively

Goodwill

Intangible assets, net of accumulated amortization of $10,594 and $8,218, respectively

Other assets

Assets held for sale

Total Assets
Liabilities and Shareholders' Equity

Liabilities:

Accrued expenses and other liabilities

Income taxes payable

Deferred service fees

Unpaid loss and loss adjustment expenses

Bank loan

Notes payable

Subordinated debt, at fair value

Net deferred income tax liabilities

Liabilities held for sale

Total Liabilities

Redeemable Class A preferred stock, no par value; 1,000,000 and unlimited number authorized at
December 31, 2018 and December 31, 2017, respectively; 222,876 and 222,876 issued and outstanding
at December 31, 2018 and December 31, 2017, respectively; redemption amount of $7,278 and $7,182
at December 31, 2018 and December 31, 2017, respectively

Shareholders' Equity:

Common stock, no par value; 50,000,000 and unlimited number authorized at December 31, 2018 and
December 31, 2017, respectively; 21,787,728 and 21,708,190 issued and outstanding at December 31,
2018 and December 31, 2017, respectively

Additional paid-in capital

Accumulated deficit

Accumulated other comprehensive income (loss)

Shareholders' equity attributable to common shareholders

Noncontrolling interests in consolidated subsidiaries

Total Shareholders' Equity

Total Liabilities, Class A preferred stock and Shareholders' Equity

$

378,240

$

See accompanying notes to Consolidated Financial Statements.

50

5,800

5,180

—

353,890

(382,196)

40,768

12,462

11,796

24,258

14,541

4,589

9,094

32,211

4,870

10,662

3,721

151

79,839

5,377

14,985

5,230

507

4,431

7,247

6,325

108,008

80,843

79,446

4,302

110,145

506,685

10,359

2,644

41,113

1,329

4,917

203,648

52,105

28,763

105,900

450,778

—

356,171

(310,953)

(3,852)

41,366

9,361

50,727

506,685

KINGSWAY FINANCIAL SERVICES INC.

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

2018

Years ended December 31,
2017
(restated)

Revenues:

Service fee and commission income
Rental income
Other income

Total revenues
Operating expenses:

Claims authorized on vehicle service agreements
Loss and loss adjustment expenses
Commissions
Cost of services sold
General and administrative expenses
Leased real estate segment interest expense

Total operating expenses
Operating loss
Other revenues (expenses), net:
Net investment income
Net realized (losses) gains
Gain on change in fair value of equity investments
Loss on change in fair value of limited liability investments, at fair value
Net change in unrealized loss on private company investments
Non-operating other income
Interest expense not allocated to segments
Amortization of intangible assets
Contingent consideration benefit
Loss on change in fair value of debt
Gain on disposal of subsidiary
Equity in net (loss) income of investee

Total other revenues (expenses), net
Loss from continuing operations before income tax expense (benefit)
Income tax expense (benefit)
(Loss) income from continuing operations
Loss on liquidation of subsidiary, net of taxes
Income (loss) from discontinued operations, net of taxes
(Loss) gain on disposal of discontinued operations, net of taxes
Net loss

Less: net income attributable to noncontrolling interests in consolidated subsidiaries
Less: dividends on preferred stock, net of tax
Net loss attributable to common shareholders

Loss per share - continuing operations:

Basic:
Diluted:
Loss per share - discontinued operations:

Basic:
Diluted:
Loss per share – net loss attributable to common shareholders:

Basic:
Diluted:
Weighted average shares outstanding (in ‘000s):

Basic:
Diluted:

$

$

$
$

$
$

$
$

See accompanying notes to Consolidated Financial Statements.

51

$

$

$
$

$
$

$
$

38,286
13,376
416
52,078

5,711
1,631
3,756
7,370
29,732
6,171
54,371
(2,293)

2,957
(17)
381
(7,393)
(1,629)
30
(7,407)
(2,376)
—
(1,720)
17
(2,499)
(19,656)
(21,949)
315
(22,264)
—
1,064
(7,136)
(28,336)

1,765
620
(30,721)

(1.13)
(1.13)

(0.28)
(0.28)

(1.41)
(1.41)

21,728
21,728

30,530
13,384
684
44,598

5,327
404
3,086
6,535
27,311
6,264
48,927
(4,329)

7,087
306
—
(1,832)
(758)
605
(6,348)
(1,085)
212
(8,487)
—
2,115
(8,185)
(12,514)
(16,688)
4,174
(494)
(16,306)
1,017
(11,609)

4,085
1,248
(16,942)

(0.05)
(0.05)

(0.73)
(0.73)

(0.79)
(0.79)

21,547
21,547

KINGSWAY FINANCIAL SERVICES INC.

Consolidated Statements of Comprehensive Loss
(in thousands) 

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

Unrealized gains (losses) arising during the period

Reclassification adjustment for amounts included in net loss

Unrealized gains removed due to disposal of discontinued operations

Change in fair value of debt attributable to instrument-specific credit risk

Equity in other comprehensive loss of limited liability investment

Recognition of currency translation loss on liquidation of subsidiary

Other comprehensive income (loss)

Comprehensive loss

Less: comprehensive income attributable to noncontrolling interests in consolidated
subsidiaries

Comprehensive loss attributable to common shareholders

 (1) Net of income tax expense (benefit) of $0 and $0 in 2018 and 2017, respectively

Years ended December 31,

2018

$

(28,336)

$

12

(18)

371

3,804

(45)

—

4,124

$

$

(24,212)

$

1,764

(25,976)

$

2017

(restated)

(11,609)

(5,213)

1,076

—

—

—

494

(3,643)

(15,252)

4,085

(19,337)

See accompanying notes to Consolidated Financial Statements.

52

KINGSWAY FINANCIAL SERVICES INC.

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

Additional
Paid-in
Capital

Accumulated
Deficit

Accumulated
Other
Comprehensive
Income (Loss)

Shareholders'
Equity
Attributable to
Common
Shareholders

Noncontrolling
Interests in
Consolidated
Subsidiaries

Total
Shareholders'
Equity

Common Stock

Shares

Amount

21,458,190

$

— $

353,882

$

(297,668) $

(208) $

56,006

$

829

$

56,835

—

21,458,190

—

250,000

—

—

—

—

—

—

—

—

—

—

—

—

—

—

1,398

2,409

—

3,807

4,107

7,914

355,280

(295,259)

(208)

59,813

4,936

64,749

(47)

1,000

—

—

(1,248)

—

1,186

—

—

(15,694)

—

—

—

—

(47)

—

(47)

1,000

(15,694)

—

4,085

1,000

(11,609)

—

339

339

(1,248)

(3,644)

(3,644)

—

1,186

—

1

—

(1,248)

(3,643)

1,186

21,708,190

$

— $

356,171

$

(310,953) $

(3,852) $

41,366

$

9,361

$

50,727

—

—

—

—

—

—

(647)

—

(647)

(40,495)

40,495

—

(7)

—

(654)

—

21,708,190

$

— $

356,171

$

(352,095) $

36,643

$

40,719

$

9,354

$

50,073

79,538

—

—

—

—

—

—

—

—

—

—

—

—

—

—

(620)

—

(1,661)

—

(30,101)

—

—

—

—

—

(30,101)

—

1,765

—

(28,336)

—

678

678

(620)

4,125

4,125

—

(1,661)

—

(1)

—

(620)

4,124

(1,661)

21,787,728

$

— $

353,890

$

(382,196) $

40,768

$

12,462

$

11,796

$

24,258

See accompanying notes to Consolidated Financial Statements.

53

—

—

—

—

—

—

—

—

—

Balance, January
1, 2017, as
reported

Correction of
prior period errors

Balance, January
1, 2017 as
restated

Common stock
issuance expenses

Conversion of
Class A preferred
stock to common
stock

Net (loss) income

Contributions
from
noncontrolling
interest holders

Preferred stock
dividends, net of
tax

Other
comprehensive
(loss) income

Stock-based
compensation

Balance,
December 31,
2017

Cumulative effect
of adoption of
ASU 2014-09

Cumulative effect
of adoption of
ASU 2016-01

Balance at
January 1, 2018,
as adjusted

Vesting of
restricted stock
awards, net of
share settlements
for tax
withholdings

Net (loss) income

Contributions
from
noncontrolling
interest holders
Preferred stock
dividends, net of
tax

Other
comprehensive
income (loss)

Stock-based
compensation, net
of forfeitures

Balance,
December 31,
2018

KINGSWAY FINANCIAL SERVICES INC.

 Consolidated Statements of Cash Flows 
(in thousands) 

2018

Years ended December 31,
2017
(restated)

Cash provided by (used in):
Operating activities:
Net loss
Adjustments to reconcile net loss income to net cash used in operating activities:
(Income) loss from discontinued operations, net of taxes
Loss (gain) on disposal of discontinued operations, net of taxes
Equity in net loss (income) of investee
Dividend received from investee
Equity in net income of limited liability investments
Depreciation and amortization expense
Contingent consideration benefit
Stock-based compensation (benefit) expense, net of forfeitures
Net realized losses (gains)
Gain on change in fair value of equity investments
Loss on change in fair value of limited liability investments, at fair value
Net change in unrealized loss on private company investments
Loss on change in fair value of debt
Deferred income taxes
Amortization of fixed maturities premiums and discounts
Amortization of note payable premium
Gain on disposal of subsidiary
Loss on liquidation of subsidiary
Changes in operating assets and liabilities:

Service fee receivable, net
Other receivables, net
Deferred acquisition costs, net
Unpaid loss and loss adjustment expenses
Deferred service fees
Other, net

Cash used in 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
Purchases of equity investments
Net proceeds from (acquisitions of) limited liability investments
Purchases of limited liability investments, at fair value
Purchases of investments in private companies
Net proceeds from other investments
Net (purchases of) proceeds from short-term investments
Proceeds from sale of investee
Proceeds from disposal of subsidiary
Net proceeds from sale of discontinued operations
Acquisition of business, net of cash acquired
Net disposals of property and equipment and intangible assets
Cash provided by (used in) investing activities - continuing operations

Cash provided by investing activities - discontinued operations
Net cash provided by investing activities
Financing activities:
Proceeds from issuance of common stock, net
Contributions from noncontrolling interest holders
Taxes paid related to net share settlements of restricted stock awards
Principal (payments on) proceeds from bank loan
Principal payments on note payable
Cash (used in) provided by financing activities - continuing operations
Cash provided by financing activities - discontinued operations
Net cash (used in) provided by financing activities
Net increase (decrease) in cash and cash equivalents and restricted cash from continuing

54

$

(28,336)

$

(1,064)
7,136
2,499
780
(241)
6,711
—
(1,661)
17
(381)
7,393
1,629
1,720
(226)
57
(939)
(17)
—

997
(2,276)
(579)
744
6,017
(2,745)
(2,765)
(7,378)
(10,143)—

7,019
5,094
(4,790)
(1,211)
3,470
(1,580)
—
1,642
(1)
1,001
565
6,343
—
519
18,071

1,977
20,048

—
678
(376)
(1,000)
(3,392)
(4,090)
—
(4,090)
11,216

(11,609)

16,306
(1,017)
(2,115)
—
(1,551)
5,390
(212)
1,186
(306)
—
1,832
758
8,487
(17,316)
95
(960)
—
494

(1,689)
(3,099)
(498)
(873)
1,830
(5,133)
(10,000)
(4,404)
(14,404)

1,756
3,754
(192)
(338)
(7,789)
(664)
(171)
2,272
250
—
—
1,017
(7,929)
4,743
(3,291)

23,392
20,101

(47)
339
—
4,917
(3,037)
2,172
—
2,172
(11,119)

KINGSWAY FINANCIAL SERVICES INC.

Cash and cash equivalents and restricted cash at beginning of period
Less: cash and cash equivalents and restricted cash of discontinued operations at beginning of
period
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

Supplemental disclosures of cash flows information:

Cash paid during the year for:

Interest

Income taxes

Non-cash investing and financing activities:

Conversion of Class A preferred stock to common stock

Accrued dividends on Class A preferred stock issued

43,874
23,512
20,362
31,578

$

36,005
4,524
31,481
20,362

Years ended December 31,

2018

2017

11,369

381

$

$

— $

620

$

12,134

37

1,000

1,248

$

$

$

$

$

See accompanying notes to Consolidated Financial Statements.

55

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, asset management and real estate industries.

NOTE 2 SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES

(a) 

Principles of consolidation:

The accompanying information in the 2018 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 variable interest entities under the Variable Interest Model prescribed by the Financial Accounting Standards 
Board ("FASB").  A variable interest entity ("VIE") is consolidated when the Company has the power to direct activities that most 
significantly impact the economic performance of the variable interest entity and has the obligation to absorb losses or the right 
to receive benefits from the variable interest entity that could potentially be significant to the variable interest entity. When a 
variable interest entity is not consolidated, the Company uses either the equity method or the cost method to account for the 
investment. Under the equity 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 loss 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 on the basis of 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.

The consolidated financial statements are prepared as of December 31, 2018 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  consolidated 
financial statements include the following subsidiaries, all of which are owned directly or indirectly: 1347 Advisors LLC; 1347 
Capital LLC; 1347 Venture Opportunity LLC; Appco Finance Corporation; American Country Underwriting Agency Inc.; Argo 
Holdings Fund I, LLC ("Argo Holdings"); Argo Management Group, LLC ("Argo Management"); ARM Holdings, Inc.; CMC 
Industries, Inc. ("CMC"); DPM SPV, LLC ("DPM"); Flower Portfolio 001, LLC ("Flower"); Itasca Capital Corp.; Itasca Investors 
LLC; IWS Acquisition Corporation ("IWS"); KAI Management Services Inc.; Kingsway America II Inc.; Kingsway America Inc. 
("KAI");  Kingsway  America Agency  Inc.;  Kingsway  Amigo  Insurance  Company  ("Amigo");  Kingsway  General  Insurance 
Company; Kingsway LGIC Holdings, LLC; Kingsway Reinsurance Corporation ("Kingsway Re"); Kingsway Warranty Holdings 
LLC; Mattoni Insurance Brokerage, Inc.; Net Lease Investment Grade Portfolio LLC ("Net Lease"); Professional Warranty Service 
Corporation ("PWSC"); Professional Warranty Services LLC; and Trinity Warranty Solutions LLC ("Trinity").

Argo Holdings, Flower and 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. 

56

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Noncontrolling interests 

The Company has noncontrolling interests attributable to Argo Holdings, CMC, DPM, IWS and Net Lease.  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 (losses) 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 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 critical accounting estimates and assumptions 
in the accompanying consolidated financial statements include the provision for unpaid loss and loss adjustment expenses; valuation 
of fixed maturities and equity investments; impairment assessment of investments; valuation of limited liability investments, at 
fair value; valuation of real estate investments; valuation of deferred income taxes; valuation of mandatorily redeemable preferred 
stock; valuation and impairment assessment of intangible assets; goodwill recoverability; deferred acquisition costs; fair value 
assumptions for subordinated debt obligations; and revenue recognition. 

(c) 

Foreign currency translation:

The consolidated financial statements have been presented in U.S. dollars because the Company's principal investments and cash 
flows are denominated in U.S. dollars.  The Company's functional currency is the U.S. dollar since the substantial majority of its 
operations is conducted in the United States.  Assets and liabilities of subsidiaries with non-U.S. dollar functional currencies are 
translated to U.S. dollars at period-end exchange rates, while revenue and expenses are translated at average monthly rates and 
shareholders' equity is translated at the rates in effect at dates of capital transactions.  The net unrealized gains or losses which 
result from the translation of non-U.S. subsidiaries financial statements are recognized in accumulated other comprehensive income 
(loss).  Such currency translation gains or losses are recognized in the consolidated statements of operations upon the sale of a 
foreign subsidiary.  Transactions settled in foreign currencies are translated to functional currencies at the exchange rate prevailing 
at the transaction dates.  The unrealized foreign currency translation gains and losses arising from available-for-sale financial assets 
are recognized in other comprehensive income (loss) until realized, at which date they are reclassified to the consolidated statements 
of operations.  Unrealized foreign currency translation gains and losses on certain interest bearing debt obligations carried at fair 
value are included in the consolidated statements of operations.

Foreign currency translation adjustments are included in shareholders' equity under the caption accumulated other comprehensive 
income (loss).  Foreign currency gains and losses resulting from transactions denominated in currencies other than the entity's 
functional currency are reflected in non-operating other income in the consolidated statements of operations. 

(d) 

Business combinations:

The acquisition method of accounting is used to account for acquisitions of subsidiaries or other businesses. The results of acquired 
subsidiaries or other businesses are included in the consolidated statements of operations from the date of acquisition.  The cost 
of an acquisition 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 acquisition over the fair value of the Company's share of the identifiable net assets acquired is recorded 
as goodwill.  If the cost of acquisition 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.

(e) 

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 (loss), net of tax, until sold or until an other-than-temporary impairment is 
recognized, at which point cumulative unrealized gains or losses are transferred to the consolidated statements of operations.

57

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Equity investments include common stocks and warrants and are reported at fair value.  Effective January 1, 2018, changes in fair 
value of equity investments are recognized in net income (loss).  Prior to 2018, changes in fair value of equity investments were 
recognized in other comprehensive income (loss). 

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.  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 represent the Company's investment in 1347 Investors LLC ("1347 Investors") as well 
as the underlying investments of Net Lease and Argo Holdings.  The Company accounts for these investments at fair value with 
changes in fair value reported in the consolidated statements of operations.  Income from limited liability investments, at fair value 
is included in loss on change in fair value of limited liability investments, at fair value.

Investments in private companies consist of common stock, preferred stock, notes receivable and derivative contracts 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.

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.

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

(f) 

Cash and cash equivalents and restricted cash:

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

(g) 

Investment in investee:

Investment in investee is comprised of an investment in an entity where the Company has the ability to exercise significant influence 
but not control.  Significant influence is presumed to exist when the Company owns, directly or indirectly, between 20% and 50% 
of the outstanding voting rights of the investee.  Assessment of significant influence is based on the substance of the relationship 
between the Company and the investee and includes consideration of both existing voting rights and, if applicable, potential voting 
rights that are currently exercisable and convertible.

At December 31, 2018 and December 31, 2017, investment in investee includes the Company's investment in the common stock 
of Itasca Capital Ltd. ("ICL").  This investment is reported as investment in investee in the consolidated balance sheets and accounted 
for under the equity method of accounting, with the Company's share of income (loss) and other comprehensive income (loss) of 
the  investee  reported  in  the  corresponding  lines  in  the  consolidated  statements  of  operations  and  consolidated  statements  of 
comprehensive income (loss), respectively.  Under the equity method of accounting, an investment in investee is initially recognized 
at cost and adjusted thereafter for the post-acquisition change in the Company's share of net assets of the investee.  Distributions 
received are classified using the cumulative earnings approach.  

58

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

At each reporting date, and more frequently when conditions warrant, management assesses its investment in investee for potential 
impairment.  If management's assessment indicates that there is objective evidence of impairment, the investee is written down to 
its recoverable amount, which is determined as the higher of its fair value less costs to sell and its value in use.  Write-downs to 
reflect  other-than-temporary  impairments  in  value  are  included  in  equity  in  net  (loss)  income  of  investee  in  the  consolidated 
statements of operations.

The most recently available financial statements of the investee are used in applying the equity method.  The difference between 
the end of the reporting period of the investee and that of the Company is no more than three months.  Adjustments are made for 
the effects of significant transactions or events that occur between the date of the investee's financial statements and the date of 
the Company's consolidated financial statements.

(h) 

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.

(i) 

Reinsurance: 

Reinsurance losses and loss adjustment expenses are accounted for on a basis consistent with those used in accounting for the 
original policies issued and the terms of the reinsurance contracts.  Losses ceded to other companies have been reported as a 
reduction of incurred loss and loss adjustment expenses.  Commissions paid to the Company by reinsurers on business ceded have 
been accounted for as a reduction of the related policy acquisition costs.  Reinsurance recoverable is recorded for that portion of 
paid and unpaid losses and loss adjustment expenses that are ceded to other companies. 

(j) 

Deferred acquisition costs, net: 

The Company defers commissions and agency expenses that are directly related to successful efforts to acquire new or existing 
vehicle service agreements to the extent they are considered recoverable.  Costs deferred on vehicle service agreements are amortized 
as the related revenues are earned.  Changes in estimates, if any, are recorded in the accounting period in which they are determined.  
Anticipated investment income is included in determining the realizable value of the deferred acquisition costs. 

(k) 

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 forty years for buildings; 
five to fifty years for site improvements; four to six years for leasehold improvements; three to ten years for furniture and equipment; 
and three to five years for computer hardware. 

(l) 

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 December 31, 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. 

The Company has the option to assess goodwill for impairment by first performing a qualitative assessment to determine whether 
it is more likely than not that the fair value of a reporting unit is less than its carrying amount.  If facts and circumstances indicate 
that it is more likely than not that the goodwill is impaired, a fair value-based impairment test would be required.  The goodwill 
impairment test is a two-step process that requires management to make judgments in determining what assumptions to use in the 
calculation.  In the first step, the fair value of the reporting unit is compared to its book value including goodwill.  If the fair value 
of the reporting unit is in excess of its book value, the related goodwill is not impaired and no further analysis is necessary.  If the 
fair value of the reporting unit is less than its book value, there is an indication of potential impairment and a second step is 
performed.  When required, the second step of testing involves calculating the implied fair value of goodwill for the reporting unit.  
The implied fair value of goodwill is determined in the same manner as goodwill recognized in a business combination, which is 
the excess of the fair value of the reporting unit determined in step one over the fair value of its net assets and identifiable intangible 

59

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

assets as if the reporting unit had been acquired.  If the carrying value of the reporting unit's goodwill exceeds the implied fair 
value of that goodwill, an impairment loss is recognized in an amount equal to that excess.  For reporting units with a negative 
book value, qualitative factors are evaluated to determine whether it is necessary to perform the second step of the goodwill 
impairment test.  

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 December 
31, 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. 

(m) 

Unpaid loss and loss adjustment expenses: 

Unpaid loss and loss adjustment expenses represent the estimated liabilities for reported loss events, incurred but not yet reported 
loss events and the related estimated loss adjustment expenses, including investigation.  Unpaid loss and loss adjustment expenses 
are determined using case-basis evaluations and statistical analyses, including industry loss data, and represent estimates of the 
ultimate cost of all claims incurred through the balance sheet date.  Although considerable variability is inherent in such estimates, 
management believes that the liability for unpaid loss and loss adjustment expenses is adequate.  The estimates are continually 
reviewed and adjusted as necessary, and such adjustments are included in current operations and accounted for as changes in 
estimates.

(n) 

Debt:

The Company's bank loan is reported at its unpaid principal balance.

The Company has notes payable at Flower, Net Lease and CMC.  The Flower and Net Lease notes payable balances are reported 
at their unpaid principal balance.  The CMC note payable is reported at amortized cost.  The CMC note payable includes a premium 
that is being amortized through the maturity date of the note payable using the effective interest rate method. 

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.  Effective January 1, 2018, the portion of the 
change in fair value of subordinated debt related to the instrument-specific credit risk is recognized in other comprehensive income 
(loss), whereas for 2017, the total change in fair value of subordinated debt was recorded in net income (loss).

(o) 

Contingent consideration:

The consideration for certain of the Company's acquisitions included future payments to the former owners that were 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 contingent 
consideration expense (benefit).  

(p) 

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 

60

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

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).

(q) 

Leases:

Rental  income  from  operating  leases  is  recognized  on  a  straight-line  basis,  based  on  contractual  lease  terms  with  fixed  and 
determinable increases over the non-cancellable term of the related lease when collectability is reasonably assured.  Rental income 
recognized in excess of amounts contractually due and collected pursuant to the underlying lease is recorded in other receivables 
in the consolidated balance sheets.  Rental expense for operating leases is recognized on a straight-line basis over the lease term, 
net of any applicable lease incentive amortization.  Below market lease liabilities recorded in connection with the acquisition 
method of accounting are amortized on a straight-line basis over the remaining term of the lease, as determined at the acquisition 
date, and are included in accrued expenses and other liabilities in the consolidated balance sheets.  Amortization of below market 
lease liabilities is included in rental income in the consolidated statements of operations. 

(r) 

Revenue recognition:

Service fee and commission income and deferred service fees

Service fee and commission income represents vehicle service agreement fees, guaranteed asset protection products ("GAP") 
commissions,  maintenance  support  service  fees,  warranty  product  commissions,  homebuilder  warranty  service  fees  and 
homebuilder  warranty  commissions  based  on  terms  of  various  agreements  with  credit  unions,  consumers,  businesses  and 
homebuilders.  

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.  On a quarterly basis, 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 when the deferred 
service fees balance is less than expected future claims costs.  

GAP commissions include commissions from the sale of GAP products.  The Company acts as an agent on behalf of the third-
party insurance company that underwrites and guaranties these GAP contracts.  The Company does not assume any insurance risk 
from the sale of GAP contracts.  IWS receives a single commission fee as its transaction price at the time it sells a GAP contract 
to  a  customer.    Each  GAP  contract  contains  two  separate  performance  obligations  -  sale  of  a  GAP  contract  and  GAP  claims 
administration.  The first performance obligation is related to the sale of a GAP contract and is satisfied upon closing the sale.  The 
second performance obligation is related to the administration of claims during the GAP contract period, generally four years.

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 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.  PWSC 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.  Warranty administrative services are earned at the time the home is enrolled and the 
warranty product is delivered.  Other warranty services include answering builder or homeowner questions regarding the home 
warranty and dispute resolution services.  Other warranty services are earned as services are performed over the warranty coverage 
period.

61

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

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, and a profit-sharing bonus on eligible warranties, which is determined based on expected ultimate loss ratio 
targets and is earned at the time the profit-sharing bonus is received.

Contingent revenue

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 discontinued operations, net of taxes.

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.

(s) 

Cost of services sold:

Cost of services sold is comprised of direct costs incurred to generate maintenance support fee revenue.  Cost of services sold 
includes payments to third-party contractors who service equipment breakdowns and perform maintenance support and is incurred 
when the services are performed.

(t) 

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 additional paid-in capital.  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.  Forfeitures are recognized 
in the period that the award is forfeited.  When stock options are exercised, the amount of proceeds together with the amount 
recorded in additional paid-in capital is recorded in shareholders' equity.  

(u) 

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 and subordinated debt are estimated using a fair value hierarchy to categorize the inputs it uses in valuation 
techniques.  The fair value of the Company's investment in investee is based on quoted market prices.  Fair values for other 
investments  approximate  their  unpaid  principal  balance.    The  carrying  amounts  reported  in  the  consolidated  balance  sheets 
approximate 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. 

NOTE 3 RESTATEMENT OF PREVIOUSLY ISSUED FINANCIAL STATEMENTS

On June 13, 2019, the Audit Committee of the Board of Directors of the Company concluded, after review and discussion with 
management, that the Company's audited consolidated financial statements for the year ended December 31, 2017 should no longer 
be relied upon.  On February 26, 2020, the Audit Committee of the Board of Directors of the Company concluded, after further 
review and discussion with management following the completion of the Company’s audit for the year ended December 31, 2018, 
that the Company's consolidated financial statements for the year ended December 31, 2017 should be further restated as a result 
of additional error corrections identified subsequent to June 13, 2019.

The Company has restated its previously reported consolidated financial statements as of and for the year ended December 31, 
2017.  The restatements reflect corrections of errors identified in connection with the preparation of the consolidated financial 
statements for the year ended December 31, 2018, and relate primarily to i) the reclassification of certain investments acquired 
from Mendota on October 18, 2018 from assets held for sale to equity investments, limited liability investments, limited liability 
investments, at fair value and other investments in the consolidated balance sheet; and the reclassification of investment income, 
related to these investments, from loss from discontinued operations, net of taxes to net investment income in the consolidated 
statement of operations ("Error 1"); ii) the consolidation of certain limited liability investments that had previously been accounted 
for under the equity method of accounting ("Error 2"); and iii) the reclassification from cash and cash equivalents to restricted 
cash in the consolidated balance sheets ("Error 3").  For the year ended December 31, 2017, correcting these errors increased the 

62

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Company’s net loss by $0.3 million.  The cumulative effect of correcting these errors increased previously reported shareholders' 
equity by $4.2 million as a result of recording noncontrolling interests in consolidated subsidiaries.      

Along with restating our financial statements as of and for the year ended December 31, 2017 to correct the errors discussed above, 
the Company has recorded certain immaterial accounting adjustments related to the periods covered by this 2018 Annual Report.  
For the year ended December 31, 2017, recording these certain immaterial accounting adjustments increased the Company’s net 
loss by $0.2 million.  The cumulative effect of recording these certain immaterial accounting adjustments increased previously 
reported shareholders' equity by $2.7 million.  Refer to the notes under the tables below for descriptions of these immaterial 
accounting adjustments.  

In addition to these items, certain other amounts have been reclassified in the consolidated balance sheet to conform to current 
year presentation.  Such reclassifications had no impact on previously reported total shareholders' equity.  

63

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

The following table presents the effects of the error corrections, immaterial accounting adjustments and reclassifications on the 
Company’s consolidated balance sheet at December 31, 2017:

(in thousands)

Assets:

Investments:

As Previously
 Reported in 
Exhibit 99.2 to 
the Form 8-K 
filed 
November 7, 
2018

Correction
of Error 1

Correction
of Error 2

Correction
of Error 3

Immaterial
Accounting
Adjustments and
Reclassifications

Fixed maturities, at fair value
Equity investments, at fair value
Limited liability investments
Limited liability investments, at fair value

$

$

14,541
4,476
4,922
5,771

— $
113
6,113
4,545

— $
—
(1,091)
21,895

— $
—
—
—

Investments in private companies, at
adjusted cost

Real estate investments, at fair value
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
Investment in investee
Accrued investment income
Service fee receivable
Other receivables
Deferred acquisition costs, net
Property and equipment
Goodwill
Intangible assets
Other assets
Assets held for sale
Total Assets

Liabilities and Shareholders' Equity

Liabilities:

Accrued expenses and other liabilities

Income taxes payable

Deferred service fees

Unpaid loss and loss adjustment expenses
Bank loan
Notes payable
Subordinated debt, at fair value
Net deferred income tax liabilities
Liabilities held for sale
Total Liabilities

Redeemable Class A preferred stock

Shareholders' Equity:
Common stock

Additional paid-in capital

Accumulated deficit

Accumulated other comprehensive loss
Shareholders' equity attributable to common
shareholders

—

—

—

—

4,020

10,662

2,321

1,400

151

32,182

20,774
—
5,230
331
4,286
6,536
6,325
108,008
80,112
80,062
4,302
136,452
484,600

—

12,171

—
—
—
—
—
—
—
—
—
—
—
(12,171)

$

— $

—

—

35,486

310
—
—
176
—
(48)
—
—
—
—
—
(14,136)
21,788

$

—

—

—

—

—

(14,985)
14,985
—
—
—
—
—
—
—
—
—
—
— $

10,924

$

— $

432

$

— $

$

$

—

—

—
—
17,179
—
—
—
17,611

—

—

—

(51)

—

(51)

2,644

42,257

1,329
4,917
186,469
52,105
28,745
105,900
435,290

5,461

—

356,021

(313,487)

(3,852)

38,682

—

—

—
—
—
—
—
—
—

—

—

—

—

—

—

64

—

—

—
—
—
—
—
—
—

—

—

—

—

—

—

December 31, 2017

As
Restated

$

14,541
4,589
9,094
32,211

4,870

10,662

3,721

151

79,839

5,377
14,985
5,230
507
4,431
7,247
6,325
108,008
80,843
79,446
4,302
110,145
$ 506,685

(a)

(a)

(b)

(c)

(b)

(d)

(d)

(b), (c),
(e), (f)

$

10,359

—
—
(850)
—

850

—

—

—

—

(722)
—
—
—
145
759
—
—
731
(616)
—
—
297

(997)

—

(1,144) (b), (g)

—
—
—
—
18
—
(2,123)

(d)

2,644

41,113

1,329
4,917
203,648
52,105
28,763
105,900
450,778

(281)

(e)

5,180

—

150

2,585

—

2,735

—

(e)

356,171

(c), (d),
(e), (f),
(g)

(310,953)

(3,852)

41,366

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Noncontrolling interests in consolidated
subsidiaries
Total Shareholders' Equity

Total Liabilities, Class A preferred stock and
Shareholders' Equity

5,167

43,849

—

—

4,228

4,177

—

—

$

484,600

$

— $

21,788

$

— $

(34) (c), (g)

2,701

297

9,361

50,727

$ 506,685

65

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

The following table presents the effects of the error corrections, immaterial accounting adjustments and reclassifications on the 
Company’s consolidated statement of operations for the year ended December 31, 2017: 

(in thousands)

December 31, 2017

As 
Previously
 Reported in 
Exhibit 99.2 
to the Form 
8-K filed 
November 7, 
2018

Correction
of Error 1

Correction
of Error 2

Correction
of Error 3

Immaterial
Accounting
Adjustments and
Reclassifications

As
Restated

Revenues:

Service fee and commission income

$

30,807

$

— $

— $

— $

(277)

(c), (g)

$ 30,530

Rental income
Other income

Total revenues
Operating expenses:

Claims authorized on vehicle service agreements
Loss and loss adjustment expenses
Commissions
Cost of services sold
General and administrative expenses
Leased real estate segment interest expense

Total operating expenses
Operating loss
Other revenues (expenses), net:
Net investment income
Net realized gains
Gain on change in fair value of limited liability
investments, at fair value

Net change in unrealized loss on private
company investments

Non-operating other income
Interest expense not allocated to segments
Amortization of intangible assets
Contingent consideration benefit
Loss on change in fair value of debt

Equity in net income of investee

Total other revenues (expenses), net

(Loss) income from continuing operations before
income tax (benefit) expense

Income tax (benefit) expense

Income (loss) from continuing operations

Loss on liquidation of subsidiary, net of taxes
Loss from discontinued operations, net of taxes

Gain on disposal of discontinued operations, net of
taxes

Net loss

Less: net income (loss) attributable to
noncontrolling interests in consolidated
subsidiaries
Less: dividends on preferred stock, net of tax

Net (loss) income attributable to common
shareholders

(Loss) earnings per share - continuing operations:

Basic:
Diluted:

Loss per share - discontinued operations:

Basic:
Diluted:

Loss per share – net loss attributable to common
shareholders:

Basic:
Diluted:

13,384
684
44,875

5,327
404
3,086
6,535
27,038
6,264
48,654
(3,779)

968
306

—

—

697
(4,977)
(1,152)
212
(8,487)

2,115

—
—
—

—
—
—
—
—
—
—
—

—
—
—

—
—
—
—
305
—
305
(305)

1,249
—

4,529
—

(45)

(1,446)

—

—
—
—
—
—

—

(10,318)

1,204

(14,097)

(16,694)

2,597

(494)
(14,252)

1,017

(11,132)

4,337

350

1,204

—

1,204

—
(1,204)

—

—

—

—

(758)

(69)
(1,371)
—
—
—

—

885

580

—

580

—
(850)

—

(270)

(219)

—

—
—
—

—
—
—
—
—
—
—
—

—
—

—

—

—
—
—
—
—

—

—

—

—

—

—
—

—

—

—

—

—
—
(277)

—
—
—
—
(32)
—
(32)
(245)

341
—

(e)

(a)

13,384
684
44,598

5,327
404
3,086
6,535
27,311
6,264
48,927
(4,329)

7,087
306

(341)

(a)

(1,832)

(f)

(d)

—

(23)
—
67
—
—

—

44

(201)

6

(d)

(207)

—
—

—

(207)

(758)

605
(6,348)
(1,085)
212
(8,487)

2,115

(8,185)

(12,514)

(16,688)

4,174

(494)
(16,306)

1,017

(11,609)

(33)

(c), (g)

898

(e)

4,085

1,248

$

$
$

$
$

$
$

(15,819) $

— $

(51)

— $

(1,072)

$ (16,942)

(0.10) $
(0.10) $

0.06
0.06

$
$

0.04
0.04

$
$

(0.64) $
(0.64) $

(0.09) $
(0.09) $

(0.04) $
(0.04) $

(0.73) $
(0.73) $

(0.01) $
(0.01) $

— $
— $

— $
— $

— $
— $

— $
— $

(0.05)
(0.05)

—
—

(0.05)
(0.05)

$
$

$
$

$
$

(0.05)
(0.05)

(0.77)
(0.77)

(0.79)
(0.79)

66

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Weighted average shares outstanding (in ‘000s):

Basic:
Diluted:

21,547
21,547

—
—

—
—

—
—

—
—

21,547
21,547

67

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

The following table presents the effects of the error corrections, immaterial accounting adjustments and reclassifications on the 
Company’s consolidated statement of cash flows for the year ended December 31, 2017:

(in thousands)

Year ended December 31, 2017

As 
Previously
 Reported in 
Exhibit 99.2 
to the Form 
8-K filed 
November 7, 
2018

Correction
of Error 1

Correction
of Error 2

Correction
of Error 3

Immaterial
Accounting
Adjustments and
Reclassifications

As
Restated

Cash provided by (used in):
Operating activities:

Net loss

$

(11,132) $

— $

(270) $

— $

(207)

(c), (d), (g),
(f), (g)

$ (11,609)

Adjustments to reconcile net loss income to net
cash (used in) provided by operating activities:

Loss from discontinued operations, net of taxes
Gain on disposal of discontinued operations, net of
taxes
Equity in net income of investee
Equity in net income of limited liability
investments
Loss on change in fair value of limited liability
investment

Depreciation and amortization expense
Contingent consideration benefit
Stock-based compensation expense, net of
forfeitures
Net realized gains
Loss on change in fair value of limited liability
investments, at fair value

Net change in unrealized loss on private company
investments

Loss on change in fair value of debt
Deferred income taxes
Amortization of fixed maturities premiums and
discounts
Amortization of note payable premium
Loss on liquidation of subsidiary
Changes in operating assets and liabilities:

Service fee receivable, net
Other receivables, net
Deferred acquisition costs, net
Unpaid loss and loss adjustment expenses

Deferred service fees

Other, net

Cash (used in) provided by operating activities -
continuing operations

Cash (used in) provided by operating activities -
discontinued operations

Net cash (used in) provided by operating activities
Investing activities:
Proceeds from sales and maturities of fixed
maturities

Proceeds from sales of equity investments
Purchases of fixed maturities
Purchases of equity investments
Net acquisitions of limited liability investments
Purchases of limited liability investments, at fair
value
Purchases of investments in private companies
Net proceeds from other investments
Net proceeds from short-term investments
Net proceeds from sale of discontinued operations
Acquisition of business, net of cash acquired
Net disposals of property and equipment and

—

850

—

—

383

—

—
—

—

—

1,446

758

—
—

—

—
—
—
—
20
—
—

—

(3,434)

(247)

—

(247)

—

—
—
—
1,121

(664)

(171)
—
—
—
—
—

14,252

1,204

(1,017)

(2,115)

—

—

(685)

(1,249)

632

5,457
(212)

1,186

(306)

—

—

8,487
(17,322)

95

(960)
494

(1,544)
(3,187)
(498)
(873)

1,754

(2,331)

(9,825)

45

—
—

—

—

—

—

—
—

—

—
—

—
—
—
—

—

—

—

(9,152)

(18,977)

4,748

4,748

1,756

3,754
(192)
(338)
(8,910)

—

—
2,272
250
1,017
(7,929)
4,743

—

—
—
—
—

—

—
—
—
—
—
—

68

—

—

—

—

—

—

—
—

—

—

—

—

—
—

—

—
—
—
—
—
—
—

—

—

—

—

—

—

—
—
—
—

—

—
—
—
—
—
—

—

—

—

—

(677)

(67)
—

—

—

(a)

(d)

386

(a)

—

—
6

—

—
—

(145)
68
—
—

(d)

(c)
(b)

76

(b), (g)

632

(b), (c), (e),
(f), (a)

72

—

72

—

—
—
—
—

—

—
—
—
—
—
—

16,306

(1,017)

(2,115)

(1,551)

—

5,390
(212)

1,186

(306)

1,832

758

8,487
(17,316)

95

(960)
494

(1,689)
(3,099)
(498)
(873)

1,830

(5,133)

(10,000)

(4,404)

(14,404)

1,756

3,754
(192)
(338)
(7,789)

(664)

(171)
2,272
250
1,017
(7,929)
4,743

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Cash (used in) provided by investing activities -
continuing operations

Cash provided by (used in) investing activities -
discontinued operations
Net cash provided by (used in) investing activities
Financing activities:
Proceeds from issuance of common stock, net
Contributions from noncontrolling interest holders
Principal proceeds from bank loan
Principal payments on note payable
Cash provided by (used in) financing activities -
continuing operations

Cash provided by financing activities -
discontinued operations

Net cash provided by (used in) financing activities
Net (decrease) increase in cash and cash
equivalents and restricted stock from continuing
operations
Cash and cash equivalents and restricted stock at
beginning of period

Less: cash and cash equivalents and restricted stock
of discontinued operations at beginning of period

Cash and cash equivalents and restricted stock of
continuing operations at beginning of period

Cash and cash equivalents and restricted stock of
continuing operations at end of period

(3,577)

—

28,140

24,563

(47)
—
4,917
(2,645)

2,225

—

2,225

(11,177)

36,475

4,524

31,951

(4,748)

(4,748)

—
—
—
—

—

—

—

—

—

—

—

286

—

286

—
339
—
(392)

(53)

—

(53)

(14)

325

—

325

—

—

—

—
—
—
—

—

—

—

—

—

—

—

—

—

—

—
—
—
—

—

—

—

72

(3,291)

23,392

20,101

(47)
339
4,917
(3,037)

2,172

—

2,172

(11,119)

(795)

(b)

36,005

—

4,524

(795)

(b)

31,481

$

20,774

$

— $

311

$

— $

(723)

$ 20,362

(a)  Reclassifications to conform to current presentation.  Such reclassifications have no impact on previously reported net 

loss or total shareholders' equity. 

(b)  Reclassifications as a result of misclassifications of amounts in a previous filing.  Such reclassifications have no impact 

on previously reported net loss or total shareholders' equity. 

(c)  Adjustments  to  Extended  Warranty  segment  service  fee  receivable  and  accrued  expenses  and  other  liabilities,  with 

offsetting adjustments to accrued expenses and other liabilities and service fee and commission income.

(d)  Adjustment to increase goodwill, with offsetting decreases to intangible assets, amortization of intangible assets and 
accumulated deficit, related to the Company's acquisition of Argo Management in 2016.  Also includes the related tax 
impact of these adjustments, resulting in an increase to net deferred income tax liabilities, with offsetting decreases to 
income tax benefit and accumulated deficit.

(e)  Adjustment to decrease redeemable Class A preferred stock, with an offsetting increase to additional paid-in capital and 
an offsetting decrease to general and administrative expenses related to the Company’s issuance of Class A preferred 
stock and Class C Warrants on February 3, 2014.  Also includes the related reclassifications of accrued dividends on 
equity-classified warrants from accrued expenses and other liabilities to redeemable Class A preferred stock and dividend 
expense from accumulated deficit to additional paid-in-capital.

(f)  Adjustments to accrued expenses and other liabilities, with offsetting adjustments to non-operating other income and 

accumulated deficit, related to escheat liability.  

(g)  Adjustment to decrease Extended Warranty deferred service fees, with an offsetting increase to service fee and commission 

income.

69

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

NOTE 4 RECENTLY ISSUED ACCOUNTING STANDARDS

(a) 

Adoption of New Accounting Standards:

Effective January 1, 2018, the Company adopted Accounting Standards Update ("ASU") 2014-09, Revenue from Contracts with 
Customers ("ASU 2014-09"), and the related amendments, utilizing the modified retrospective approach, which created a new 
comprehensive revenue recognition standard that serves as the single source of revenue guidance for all contracts with customers 
to transfer goods or services or contracts for the transfer of nonfinancial assets, unless those contracts are within the scope of other 
standards.  The core principle of ASU 2014-09 is that an entity recognizes revenue to depict the transfer of promised goods or 
services to customers in an amount that reflects the consideration to which the entity expects to be entitled in exchange for those 
goods or services.  Insurance contracts, lease contracts and investments are not within the scope of ASU 2014-09.  ASU 2014-09 
is applicable to the Company's service fee and commission income.  Service fee and commission income represents vehicle service 
agreement  fees,  GAP  commissions,  maintenance  support  service  fees,  warranty  product  commissions,  homebuilder  warranty 
service  fees  and  homebuilder  warranty  commissions  based  on  terms  of  various  agreements  with  credit  unions,  consumers, 
businesses and homebuilders.  With the exception of GAP commissions and homebuilder warranty service fees, the adoption of 
ASU 2014-09 did not change the way the Company recognized revenue for the year ended December 31, 2018.  The new guidance 
affects IWS' GAP commissions and PWSC's homebuilder warranty service fees, which will be recognized more slowly as compared 
to the historic revenue recognition pattern prior to the Company’s adoption of ASU 2014-09.  As a result of the adoption of ASU 
2014-09, the Company also recorded a cumulative effect adjustment to increase accumulated deficit by $0.6 million and increase 
deferred service fees by $0.6 million.  Prior periods have not been restated to conform to the current presentation.  Refer to Note 
20, "Revenue from Contracts with Customers," for further details.

Effective January 1, 2018, the Company adopted ASU 2016-01, Financial Instruments-Overall (Subtopic 825-10): Recognition 
and Measurement of Financial Assets and Financial Liabilities ("ASU 2016-01").  The amendments in ASU 2016-01 address 
certain aspects of recognition, measurement, presentation, and disclosure of financial instruments.  Most significantly, ASU 2016-01 
requires  (1)  equity  investments  (except  those  accounted  for  under  the  equity  method  of  accounting  or  those  that  result  in 
consolidation of an investee) to be measured at fair value with changes in fair value recognized in net income (loss); however, an 
entity may choose to measure equity investments that do not have readily determinable fair values at cost, adjusted for observable 
price changes and impairments; and (2) an entity to present separately in other comprehensive income (loss) the portion of the 
total change in the fair value of a liability resulting from a change in the instrument-specific credit risk when the entity has elected 
to measure the liability at fair value in accordance with the fair value option for financial instruments.  The Company has elected
to measure its investments in private companies at cost, adjusted for observable price changes and impairments.  Previously, the 
Company  recorded  its  equity  investments  at  fair  value  with  net  unrealized  gains  or  losses  reported  in  accumulated  other 
comprehensive income (loss) and its subordinated debt at fair value with the total change in fair value reported in net income 
(loss).  As a result of the adoption of ASU 2016-01, at January 1, 2018 cumulative net unrealized losses on equity investments of 
$0.0 million were reclassified from accumulated other comprehensive income (loss) into accumulated deficit and a cumulative 
$40.5  million  change  in  fair  value  of  subordinated  debt  attributable  to  instrument-specific  credit  risk  was  reclassified  from 
accumulated deficit to accumulated other comprehensive income (loss).  Prior periods have not been restated to conform to the 
current presentation.

Effective January 1, 2018, the Company adopted ASU 2016-15, Classification of Certain Cash Receipts and Cash Payments ("ASU 
2016-15"). The objective of ASU 2016-15 is to reduce diversity in the classification of cash receipts and payments for specific 
cash flow issues, including debt prepayment or debt extinguishment costs, contingent consideration payments made after a business 
combination and proceeds from the settlement of insurance claims.  The adoption of the standard did not affect the Company's 
consolidated statements of cash flows.

Effective January 1, 2018, the Company adopted ASU 2016-18, Statement of Cash Flows (Topic 230) Restricted Cash ("ASU 
2016-18").  The objective of ASU 2016-18 is to explain the change during the period in the total cash, cash equivalents and amounts 
generally described as restricted cash or restricted cash equivalents.  Amounts generally described as restricted cash and cash 
equivalents should be included with the cash and cash equivalents when reconciling the beginning of period and end of period 
total amounts shown on the statement of cash flows.  As a result of the adoption of the standard, the change in restricted cash is 
included in the consolidated statements of cash flows.

Effective July 1, 2018, the Company adopted ASU 2018-07, Compensation-Stock Compensation (Topic 718): Improvements to 
Nonemployee Share-Based Payment Accounting ("ASU 2018-07").  ASU 2018-07 was issued to simplify the accounting for share-
based transactions by expanding the scope of Topic 718 from only being applicable to share-based payments to employees to also 
include share-based payment transactions for acquiring goods and services from nonemployees.  During the third quarter of 2018, 

70

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

the Company granted restricted common stock awards to a nonemployee.  Refer to Note 23, "Stock-Based Compensation," for 
further details.

(b) 

Accounting Standards Not Yet Adopted:

In February 2016, the FASB issued ASU 2016-02, Leases ("ASU 2016-02").  ASU 2016-02 was issued to improve the financial 
reporting of leasing transactions.  Under current guidance for lessees, leases are only included on the balance sheet if certain 
criteria, classifying the agreement as a capital lease, are met.  This update will require the recognition of a right-of-use asset and 
a corresponding lease liability, discounted to the present value, for all leases that extend beyond 12 months.  For operating leases, 
the asset and liability will be amortized over the lease term on a straight-line basis, with all cash flows included within operating 
activities in the statement of cash flows.  The accounting treatment for lessors will remain relatively unchanged.  ASU 2016-02 
is effective for annual and interim reporting periods beginning after December 15, 2018.  The Company will adopt ASU 2016-02 
effective January 1, 2019 using the modified retrospective transition method and will not restate comparative periods.  The Company 
plans to elect the package of practical expedients permitted under the transition guidance within ASU 2016-02, which will allow 
the Company to carry forward prior conclusions about lease identification, classification and initial direct costs for leases entered 
into prior to adoption of ASU 2016-02.  The adoption of ASU 2016-02 will have no impact on the Company's shareholders' equity 
as of January 1, 2019, but the Company estimates it will record a right-of-use asset of approximately $2.7 million; a corresponding 
lease liability of approximately $2.9 million; and a reversal of December 31, 2018 accrued rent expense of $0.2 million.  

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 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.  ASU 2016-13 is 
effective for annual periods beginning after December 15, 2019, and interim periods within those annual periods with early adoption 
permitted for fiscal years beginning after December 31, 2018 and interim periods within such year.  The Company is currently 
evaluating ASU 2016-13 to determine the potential impact that adopting this standard will have on its consolidated financial 
statements. 

In January 2017, the FASB issued ASU 2017-04, Intangibles - Goodwill and Other (Topic 350): Simplifying the Test for Goodwill 
Impairment ("ASU 2017-04").  ASU 2017-04 was issued to simplify the subsequent measurement of goodwill.  This update changes 
the impairment test by requiring an entity to compare the fair value of a reporting unit with its carrying amount as opposed to 
comparing the carrying amount of goodwill with its implied fair value.  ASU 2017-04 is effective for annual and interim reporting 
periods beginning after December 15, 2019.  Early adoption is permitted.  The Company does not believe the adoption of ASU 
2017-04 will have a material effect on its consolidated financial statements.

NOTE 5 ACQUISITION

On October 12, 2017, the Company acquired 100% of the outstanding shares of PWSC for cash consideration of $10.0 million.  
As further discussed in Note 28, "Segmented Information," PWSC is included in the Extended Warranty segment.   PWSC is based 
in Virginia and is a leading provider of new home warranty products and administration services to the largest tier of domestic 
residential construction firms in the United States.  This acquisition allows the Company to grow its portfolio of warranty companies 
and expand into the home warranty business.

This acquisition was accounted for as a business combination using the acquisition method of accounting.  The purchase price 
was allocated to the assets acquired and liabilities assumed based upon their estimated fair values at the date of acquisition.  During 
the third quarter of 2018, the Company completed its fair value analysis of the assets acquired and liabilities assumed.  Goodwill 
of $2.9 million was recognized, which represented a $6.2 million decrease from the amount recorded at December 31, 2017, and 
$6.2  million  of  separately  identifiable  intangible  assets  were  recognized  resulting  from  the  valuations  of  acquired  customer 
relationships, non-compete agreement and trade name.  Refer to Note 13, "Intangible Assets," for further disclosure of the intangible 
assets related to this acquisition.  The goodwill 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 warranty companies and acquire an assembled workforce.  The 
goodwill is not deductible for tax purposes.  During the years ended December 31, 2018 and December 31, 2017, the Company 

71

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

incurred acquisition-related expenses of $0.0 million and $0.2 million, respectively, which are included in general and administrative 
expenses in the consolidated statement of operations.

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

(in thousands)

Cash and cash equivalents

Other receivables
Service fee receivable
Deferred tax asset
Property and equipment
Goodwill

Intangible assets - subject to amortization

Intangible asset - not subject to amortization

Other assets

Total assets

Deferred service fees

Accrued expenses and other liabilities

Total liabilities

Purchase price

October 12, 2017

2,071

50
1,422
118
238
2,867

5,569

627

206

13,168

800

2,368

3,168

10,000

$

$

$

$

$

NOTE 6 DISPOSAL, DISCONTINUED OPERATIONS AND LIQUIDATION

(a)  

Disposal

On June 1, 2018, the Company disposed of its subsidiary, Itasca Real Estate Investors, LLC ("Itasca Real Estate").  As a result of 
the disposal, the Company recognized a gain of $0.0 million during the year ended December 31, 2018.  The earnings of Itasca 
Real Estate are included in the consolidated statements of operations through the June 1, 2018 disposal date.  

(b)  

Discontinued Operations

Mendota Insurance Company, Mendakota Insurance Company and Mendakota Casualty Company:

On July 16, 2018, the Company announced it had entered into a definitive agreement to sell its non-standard automobile insurance 
companies  Mendota  Insurance  Company,  Mendakota  Insurance  Company  and  Mendakota  Casualty  Company  (collectively 
"Mendota").  On October 18, 2018, the Company completed the previously announced sale of Mendota.  The final aggregate 
purchase price of $28.6 million was redeployed primarily to acquire equity investments, limited liability investments, limited 
liability investment, at fair value and other investments, which were owned by Mendota at the time of the closing, and to fund 
$5.0 million into an escrow account to be used to satisfy potential indemnity obligations under the definitive stock purchase 
agreement.  As part of the transaction, the Company will indemnify the buyer for any loss and loss adjustment expenses with 
respect to open claims and certain specified claims in excess of Mendota's carried unpaid loss and loss adjustment expenses at 
June 30, 2018.  The maximum obligation to the Company with respect to the open claims is $2.5 million.  There is no maximum 
obligation to the Company with respect to the specified claims. During the first quarter of 2019, Mendota settled one of the two 
specified claims for no loss to the Company.  During the fourth quarter of 2019, Mendota notified the Company that it had entered 
into an agreement to settle the remaining specified claim.  The Company estimates it will incur a net loss of approximately $1.8 
million related to the settlement of the remaining specified claim, which the Company will report in its consolidated statement of 
operations for the year ended December 31, 2019.

72

   
KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

As a result of this announcement, Mendota, which was previously disclosed as part of the Insurance Underwriting segment, has 
been classified as a discontinued operation and the results of their operations are reported separately for all periods presented.  The 
Company recognized a loss on disposal of Mendota of $8.5 million for the year ended December 31, 2018.  The assets and liabilities 
of Mendota are presented as held for sale in the consolidated balance sheets at December 31, 2017.  

Assigned Risk Solutions Ltd.:

On April 1, 2015, the Company closed on the sale of its subsidiary, Assigned Risk Solutions Ltd. ("ARS").  The terms of the sale 
provided for receipt by the Company of future earnout payments equal to 1.25% of ARS' written premium and fee income during 
the earnout periods.  The earnout payments were payable in three annual installments beginning in April 2016 through April 2018.  
During 2018, the Company received cash consideration, before expenses, of $1.7 million for the third annual installment earnout 
payment.  During 2017, the Company received cash consideration, before expenses, of $1.3 million for the second annual installment 
earnout payment.  Net of expenses, the Company recorded an additional gain on disposal of ARS of $1.3 million and $1.0 million
for the years ended December 31, 2018 and December 31, 2017, respectively.  As a result of the sale, ARS, previously disclosed 
as part of the Extended Warranty segment, has been classified as a discontinued operation. 

Summary financial information for Mendota and ARS included in (loss) income from discontinued operations, net of taxes in the 
statements  of  operations  for  the  years  ended  December 31,  2018  and  December  31,  2017  is  presented  below:

(in thousands)

Income (loss) from discontinued operations, net of taxes:

Revenues:

Net premiums earned

Net investment income (loss)

Net realized (losses) gains

Other-than temporary impairment loss

Gain on change in fair value of equity investments

Other income

Total revenues

Expenses:

Loss and loss adjustment expenses

Commissions and premium taxes

General and administrative expenses

Impairment of intangible assets

Total expenses

Income (loss) from discontinued operations before income tax benefit

Income tax benefit

Income (loss) from discontinued operations, net of taxes

(Loss) gain on disposal of discontinued operations before income tax expense

Income tax expense

(Loss) gain on disposal of discontinued operations, net of taxes

Years ended December 31,

2018

2017

$

71,182

$

130,443

733

(5)

—

28

7,486

79,424

58,706

7,172

12,482

—

78,360

1,064

—

1,064

(7,136)

—

(7,136)

(353)

3,465

(316)

—

9,938

143,177

120,387

20,682

19,231

250

160,550

(17,373)

(1,067)

(16,306)

1,017

—

1,017

Total loss from discontinued operations, net of taxes

$

(6,072) $

(15,289)

73

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

The assets and liabilities of Mendota are presented as held for sale in the consolidated balance sheets at December 31, 2017.  The 
carrying amounts of the major classes of assets and liabilities of Mendota at December 31, 2017 are as follows:

(in thousands)
Assets
Investments:

Fixed maturities, at fair value
Equity investments, at fair value

Total investments
Cash and cash equivalents
Accrued investment income
Premiums receivable, net
Other receivables
Deferred acquisition costs, net
Property and equipment, net
Intangible assets, net
Other assets
Assets held for sale
Liabilities
Unpaid loss and loss adjustment expenses
Unearned premiums
Net deferred income tax liabilities
Accrued expenses and other liabilities
Liabilities held for sale

(c)  

Liquidation

December 31, 2017

$

$

$

$

38,673
4,405
43,078
23,512
195
27,855
603
6,720
222
7,553
407
110,145

62,323
36,686
1,586
5,305
105,900

During 2017, the Company's subsidiary, Kingsway ROC GP ("ROC GP"), was liquidated.  As a result of the liquidation of this 
subsidiary, the Company realized a net after-tax loss of $0.5 million for the year ended December 31, 2017.  This loss represents 
the foreign exchange loss previously recorded in accumulated other comprehensive loss and now recognized in the statements of 
operations as a result of the liquidation of ROC GP.  Summarized financial information for liquidation of subsidiary is shown 
below:

(in thousands)

Liquidation:
Loss on liquidation before income taxes
Income tax benefit
Loss on liquidation of subsidiary, net of taxes

NOTE 7 VARIABLE INTEREST ENTITIES

Years ended December 31,
2017

2018

$

$

— $
— $
— $

(494)
—
(494)

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 

74

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

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.

(a)  Consolidated VIEs

Argo Holdings Fund I, LLC:

The Company held a 43.4% investment in Argo Holdings at December 31, 2018 and December 31, 2017.  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, 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, 
2018 and December 31, 2017.

Net Lease Investment Grade Portfolio, LLC:

The Company held a 71.0% and 71.8% investment in Net Lease at December 31, 2018 and December 31, 2017, respectively.  Net 
Lease holds three commercial properties under triple net leases. The properties are encumbered by mortgage loans.  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, 2018 and December 31, 2017.

DPM SPV, LLC:

The Company held a 66.7% investment in DPM at December 31, 2018 and December 31, 2017.  DPM holds an investment in 
Swerve Pay LLC, which is a software development firm for medical imaging software.  DPM 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 
DPM due to its right to absorb significant economics in DPM and to control the management decisions of DPM, which allows the 
Company to hold the power to direct the significant activities of the VIE.  As such, the Company is the primary beneficiary of 
DPM and consolidated DPM at December 31, 2018 and December 31, 2017.

Insurance Income Strategies Ltd.

Insurance Income Strategies Ltd. ("IIS") is a Bermuda corporation organized to offer collateralized reinsurance in the property 
catastrophe market through its wholly owned operating subsidiary IIS Re Ltd.  The Company held 100% of the outstanding common 
stock of IIS at December 31, 2018 and December 31, 2017.  IIS was considered to be a VIE at December 31, 2017 as IIS did not 
hold sufficient equity to finance its activities without additional subordinated support.  At December 31, 2017, the Company was 
deemed to have the power to direct the activities of IIS through its voting rights and had the right to absorb significant economics 
in IIS; therefore, the Company was the primary beneficiary of IIS and consolidated IIS at December 31, 2017.  The results of 
consolidation of IIS at December 31, 2017 were immaterial and are reflected as zero in the following table at December 31, 2017.

Effective August 10, 2018, IIS issued preferred stock to a third-party investor in the amount of $15.0 million.  In conjunction with 
this transaction, documents were executed prohibiting IIS to enter into any material contract, issue equity or debt securities, incur 
any other material obligation or enter into, amend or waive any material term of any agreement between the Company and IIS 
without the prior written consent of the third-party investor.  As a result, while IIS raised sufficient equity to finance its activities, 
the holders of equity at risk of IIS no longer had proportionate voting rights, resulting in IIS continuing to be considered a VIE, 

75

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

including at December 31, 2018.  Due to the contractual agreements executed in conjunction with the third-party investment, the 
Company no longer holds power over IIS as of August 10, 2018.  As such, the Company is no longer considered the primary 
beneficiary as of August 10, 2018 and deconsolidated IIS.

The following table summarizes the assets and liabilities related to VIEs consolidated by the Company at December 31, 2018 and 
December 31, 2017: 

(in thousands)

Assets
Limited liability investments, at fair value
Investments in private companies, at adjusted cost
Cash and cash equivalents
Accrued investment income
Other receivable
Total Assets
Liabilities
Accrued expenses and other liabilities
Notes payable
Total Liabilities

2018

25,809
750
351
217
48
27,175

252
9,000
9,252

$

$

December 31,
2017

21,895
750
220
107
—
22,972

97
9,000
9,097

$

$

No arrangements exist requiring the Company to provide additional funding to the consolidated VIEs in excess of the Company’s 
unfunded  commitments.   At  December 31,  2018  and  December 31,  2017,  the  Company  had  $0.6  million  and  $1.2  million, 
respectively, of unfunded commitments to Argo Holdings.  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, 2018 and 
December 31, 2017, the Company had zero and $0.1 million, respectively, of 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, 2018 and December 31, 2017:

(in thousands)

Investments in non-consolidated VIEs

2018

December 31,

2017

Carrying
Value

$

4,664

Maximum
Loss Exposure
4,664
$

Carrying
Value

$

15,363

Maximum
Loss Exposure
15,363
$

76

 
 
 
 
 
KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

The following table summarizes the Company’s non-consolidated VIEs by category at December 31, 2018 and December 31, 
2017:

(in thousands)

2018

December 31,

2017

Carrying
Value

Percent of
total

Carrying
Value

Percent of
total

Investments in non-consolidated VIEs:

Real estate related
Non-real estate related

Total investments in non-consolidated VIEs

$

1,710
2,954
4,664

36.7%
63.3%
100.0% $

1,726
13,637
15,363

11.2%
88.8%
100.0%

The  following  table  presents  aggregated  summarized  financial  information  of  the  Company’s  non-consolidated  VIEs  at 
December 31, 2018 and December 31, 2017.  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 (loss) income

NOTE 8 INVESTMENTS

2018
363,516
296,521
66,995

2018
(29,619)

December 31,
2017
332,181
238,819
93,362

December 31,
2017
(4,294)

$

$

$

$

As further discussed in Note 4, "Recently Issued Accounting Standards," effective January 1, 2018, the Company adopted ASU 
2016-01.  As a result of the adoption, equity investments are no longer classified as available-for-sale.  Prior periods have not 
been restated to conform to the current presentation.  

The amortized cost, gross unrealized gains and losses, and estimated fair value of the Company's available-for-sale investments 
at December 31, 2018 and December 31, 2017 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

Corporate

Total fixed maturities

Amortized
Cost

Gross
Unrealized
Gains

Gross
Unrealized
Losses

Estimated 
Fair Value

December 31, 2018

$

1

—

—

—

1

48

14

70

41

173

$

5,547

607

3,186

2,920

12,260

$

5,594

$

621

3,256

2,961

12,432

77

 
 
 
 
KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Amortized
Cost

Gross
Unrealized
Gains

Gross
Unrealized
Losses

Estimated 
Fair Value

December 31, 2017

(in thousands)

Fixed maturities:

U.S. government, government agencies and
authorities

$

5,671

$

States, municipalities and political subdivisions

Mortgage-backed

Corporate

Total fixed maturities

Equity investments:

Common stock

Warrants - publicly traded

Warrants - not publicly traded

Total equity investments

639

2,933

5,464

14,707

3,883

25

960

4,868

Total fixed maturities and equity investments

$

19,575

$

—

—

—

—

—

—

146

173

319

319

$

$

59

13

57

37

166

313

—

285

598

764

$

5,612

626

2,876

5,427

14,541

3,570

171

848

4,589

$

19,130

Net unrealized gains and losses in the tables above are reported as other comprehensive income (loss) with the exception of net 
unrealized  losses  of  $0.1  million,  at  December 31,  2017,  related  to  warrants  -  not  publicly  traded,  which  are  reported  in  the 
consolidated statements of operations.

The table below summarizes the Company's fixed maturities at December 31, 2018 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
5,462
5,342
217
1,411
12,432

$

$

$

December 31, 2018
Estimated Fair
Value
5,445
5,233
210
1,372
12,260

$

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, 2018 and December 31, 2017.  The tables segregate the holdings based on the period 
of time the investments have been continuously held in unrealized loss positions.

78

 
 
 
 
KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

(in thousands)

December 31, 2018

Less than 12 Months

Greater than 12 Months

Total

Estimated
Fair Value

Unrealized
Loss

Estimated
Fair Value

Unrealized
Loss

Estimated
Fair Value

Unrealized
Loss

Fixed maturities:

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

Total fixed maturities

$

1,497

$

1

$

2,609

$

47

$

4,106

$

—
800
595

2,892

—
1
1

3

606
2,134
2,151

7,500

14
69
40

606
2,934
2,746

170

10,392

173

(in thousands)

December 31, 2017

Less than 12 Months

Greater than 12 Months

Total

Estimated
Fair Value

Unrealized
Loss

Estimated
Fair Value

Unrealized
Loss

Estimated
Fair Value

Unrealized
Loss

$

1,545

$

9

$

5,612

$

Fixed maturities:

U.S. government, government
agencies and authorities

States, municipalities and political
subdivisions

Mortgage-backed

Corporate

Total fixed maturities

Equity investments:

Common stock

Warrants

Total equity investments

Total

$

4,067

$

626

2,876

2,427

9,996

3,570

675

4,245

$

14,241

$

50

13

57

37

—

—

—

157

1,545

313

285

598

755

—

—

—

$

1,545

$

—

—

—

9

—

—

—

9

626

2,876

2,427

11,541

3,570

675

4,245

$

15,786

$

48

14
70
41

59

13

57

37

166

313

285

598

764

There  are  approximately  64  and  68  individual  available-for-sale  investments  that  were  in  unrealized  loss  positions  as  of 
December 31, 2018 and December 31, 2017, respectively. 

The  establishment  of  an  other-than-temporary  impairment  on  an  available-for-sale  investment  or  limited  liability  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.  The analysis includes some or all of the following procedures as 
deemed appropriate by the Company:

• 
• 
• 

• 
• 

• 

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; 

79

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

• 

• 

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 the 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 past 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.

As a result of the analysis performed by the Company to determine declines in market value that are other-than-temporary, there 
were no write-downs for other-than-temporary impairment related to available-for-sale investments recorded for the years ended 
December 31, 2018 and December 31, 2017.  

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.

Limited liability investments include investments in limited liability companies and limited partnerships.  The Company's interests 
in these investments 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.  As of December 31, 2018 and 
December 31, 2017, the carrying value of limited liability investments totaled $4.8 million and $9.1 million, respectively.  At 
December 31, 2018, the Company has no unfunded commitments related to limited liability investments. 

Limited  liability  investments,  at  fair  value  represent  the  Company's  investment  in  1347  Investors  as  well  as  the  underlying 
investments  of  Net  Lease  and Argo  Holdings.   As  of  December 31,  2018  and  December 31,  2017,  the  carrying  value  of  the 
Company's limited liability investments, at fair value was $26.0 million and $32.2 million, respectively.  The Company recorded 
impairments related to limited liability investments, at fair value of $0.1 million and $0.1 million for the years ended December 31, 
2018 and December 31, 2017, respectively, which are included in loss on change in fair value of limited liability investments, at 
fair value in the consolidated statements of operations. At December 31, 2018, the Company has unfunded commitments totaling 
$0.6 million to fund limited liability investments, at fair value. 

Investments in private companies consist of common stock, preferred stock, notes receivable and derivative contracts in privately 
owned  companies  and  investments  in  limited  liability  companies  in  which  the  Company’s  interests  are  deemed  minor.   The 
Company's investments in private companies do not have readily determinable fair values.  As further discussed in Note 4, "Recently 
Issued Accounting Standards," effective January 1, 2018, the Company adopted ASU 2016-01.  As a result of the adoption, the 
Company has elected to record investments in private companies at cost, adjusted for observable price changes and impairments.  
For the year ended December 31, 2018, the Company recorded adjustments of $0.6 million to decrease the fair value of certain 
investments in private companies for observable price changes, which are included in net change in unrealized loss on private 
company investments in the consolidated statements of operations. 

The Company performs a quarterly impairment analysis of its investments in private companies.  The analysis includes some or 
all of the following procedures as deemed appropriate by the Company:

• 
• 
• 
• 
• 
• 

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.

80

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

As a result of the analysis performed, the Company recorded impairments related to investments in private companies of $1.0 
million and $2.0 million for the years ended December 31, 2018 and December 31, 2017, respectively, which are included in net 
change in unrealized loss on private company investments in the consolidated statements of operations.

As of December 31, 2018 and December 31, 2017, the carrying value of the Company's investments in private companies totaled 
$3.1 million and $4.9 million, respectively. 

Real estate investments are reported at fair value.  As of December 31, 2018 and December 31, 2017, the carrying value of the 
Company's real estate investments totaled $10.7 million and $10.7 million, respectively. 

Other  investments  include  collateral  loans  and  are  reported  at  their  unpaid  principal  balance.   As  of  December 31,  2018  and 
December 31, 2017, the carrying value of other investments totaled $2.1 million and $3.7 million, respectively.

The Company had previously entered into two separate performance share grant agreements with 1347 Property Insurance Holdings, 
Inc. ("PIH"), whereby the Company will be entitled to receive up to an aggregate of 475,000 shares of PIH common stock upon 
achievement of certain milestones for PIH’s stock price.  Pursuant to the performance share grant agreements, if at any time the 
last sales price of PIH’s common stock equals or exceeds: (i) $10.00 per share (as adjusted for stock splits, stock dividends, 
reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 
100,000  shares  of  PIH  common  stock;  (ii)  $12.00  per  share  (as  adjusted  for  stock  splits,  stock  dividends,  reorganizations, 
recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares 
of PIH common stock (in addition to the 100,000 shares of common stock earned pursuant to clause (i) herein); (iii) $15.00 per 
share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within 
any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 225,000 shares of 
common stock earned pursuant to clauses (i) and (ii) herein); and (iv) $18.00 per share (as adjusted for stock splits, stock dividends, 
reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 
125,000 shares of PIH common stock (in addition to the 350,000 shares of common stock earned pursuant to clauses (i), (ii) and 
(iii) herein).  To the extent shares of PIH common stock are granted to the Company under either of the performance share grant 
agreements, they will be recorded at the time the shares are granted and will have a valuation equal to the last sales price of PIH 
common stock on the day prior to such grant.

On January 2, 2018, the Company entered into an agreement with PIH to cancel the $10.00 per share performance shares grant 
agreement in exchange for cash consideration of $0.3 million.  On July 24, 2018, the Company entered into an agreement with 
PIH to cancel the $12.00 per share, $15.00 per share and $18.00 per share performance share grant agreement in exchange for 
cash consideration of $1.0 million.  For the year ended December 31, 2018, the Company recorded gains, included in gain on 
change in fair value of equity investments in the consolidated statements of operations, of $1.3 million related to these transactions.  
No shares were received by the Company under either of the performance share grant agreements as of December 31, 2018.

Net investment income for the years ended December 31, 2018 and December 31, 2017, 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
Loss on change in fair value of warrants - not publicly traded
Income from real estate investments
Other

Gross investment income
Investment expenses
Net investment income

2018

Years ended December 31,
2017
(restated)

236
359
241
1,174
—
800
230
3,040
(83)
2,957

$

$

190
501
1,551
3,973
(292)
800
386
7,109
(22)
7,087

$

$

81

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Gross realized gains and losses on available-for-sale investments, limited liability investments and limited liability investments, 
at fair value for the years ended December 31, 2018 and December 31, 2017 is comprised as follows:

(in thousands)

Gross realized gains
Gross realized losses
Net realized (losses) gains

$

$

2018

Years ended December 31,
2017
(restated)
309
(3)
306

398
(415)
(17)

$

$

Gain on change in fair value of equity investments for the years ended December 31, 2018 and December 31, 2017 is comprised 
as follows:

(in thousands)

Net gains recognized on equity investments sold during the period
Change in unrealized losses on equity investments held at end of the period
Gain on change in fair value of equity investments

$

$

Years ended December 31,

2018
1,464
(1,083)
381

$

$

2017
—
—
—

NOTE 9 INVESTMENT IN INVESTEE

Investment in investee includes the Company's investment in the common stock of ICL.  The carrying value of the Company’s 
investment in investee  is accounted for under the equity method, calculated using ICL’s reported financial statements on a three-
month lag.  The carrying value, estimated fair value and approximate equity percentage for the Company's investment in investee 
at December 31, 2018 and December 31, 2017 were as follows:

(in thousands, except for percentages)

December 31, 2018

December 31, 2017

Equity
Percentage

Estimated Fair
Value

Carrying
Value

Equity
Percentage

Estimated Fair
Value

Carrying
Value

ICL

22.9% $

951

$

951

31.2% $

3,816

$

5,230

The carrying value of the Company's investment in investee at December 31, 2017 in the table above is calculated using ICL’s 
financial statements reported as of and for the period ended September 30, 2017. The estimated fair value of the Company's 
investment in investee at December 31, 2017 in the table above is calculated based on the published closing price of ICL common 
stock at September 30, 2017 to be consistent with the three-month lag in calculating its carrying value under the equity method.  

The carrying value of the Company's investment in investee at December 31, 2018, using ICL’s financial statements reported as 
of and for the period ended September 30, 2018, was calculated to be $2.7 million.  The Company performed an analysis to 
determine whether its $2.7 million carrying value calculated under the equity method is recoverable.  As part of its analysis, the 
Company considered that the estimated fair value of the Company's investment in investee at December 31, 2018, as presented in 
the table above and as calculated based on the published closing price of ICL common stock at December 31, 2018, was $1.0 
million.  The Company concluded that the $2.7 million carrying value of its investment in investee, as calculated under the equity 
method, had an other than temporary impairment as of December 31, 2018.  As a result, the Company wrote down the carrying 
value of its investment in investee as of December 31, 2018, as presented in the table above, by $1.7 million such that its carrying 
value equals the $1.0 million estimated fair value of the Company's investment in investee as calculated based on the published 
closing price of ICL common stock at December 31, 2018.

82

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Prior to the third quarter of 2018, the Company owned 6,799,449 shares of ICL common stock.  On July 30, 2018, the Company 
executed an agreement to sell 1,813,889 shares of ICL common stock, having a carrying value of $1.3 million, for $1.0 million.  
As a result, the Company recorded a loss of $0.3 million on the sale and reduced its ownership percentage in ICL to 22.9%.  Also 
during the year ended December 31, 2018, the Company received a dividend of $0.8 million from ICL. 

The Company reported equity in net loss of investee of $2.5 million for the year ended December 31, 2018, which includes the 
$1.7 million other than temporary impairment, the $0.3 million loss on sale and $0.5 million of equity in net loss of investee.   The 
Company reported equity in net income of investee of $2.1 million for the year ended December 31, 2017. 

NOTE 10 REINSURANCE

Ceded loss and loss adjustments expenses, unpaid loss and loss adjustment expenses and commissions as of and for the years 
ended December 31, 2018 and December 31, 2017 are summarized as follows:

(in thousands)

Ceded loss and loss adjustment expenses
Ceded unpaid loss and loss adjustment expenses
Ceding commissions

NOTE 11 DEFERRED ACQUISITION COSTS

$

Years ended December 31,
2017
(226)
72
226

2018
105
—
(105)

$

Policy acquisition costs consist primarily of commissions and agency expenses incurred related to successful efforts to acquire 
vehicle service agreements.  Acquisition costs deferred on vehicle service agreements are amortized over the period in which the 
related revenues are earned.

The components of deferred acquisition costs and the related amortization expense as of and for the years ended December 31, 
2018 and December 31, 2017 are comprised as follows:

(in thousands)

Balance at January 1, net

Additions

Amortization

Balance at December 31, net

NOTE 12 GOODWILL

Years ended December 31,

2018

6,325

3,825
(3,246)
6,904

$

$

2017

5,827

3,484
(2,986)
6,325

$

$

Goodwill was $74.7 million and $80.8 million at December 31, 2018 and December 31, 2017, respectively, and is attributable to 
the Extended Warranty and Leased Real Estate reportable segments.  As further discussed in Note 5, "Acquisition," during the 
third quarter of 2018, the Company completed its fair value analysis of the assets acquired and liabilities assumed related to the 
acquisition of PWSC on October 12, 2017.  As a result, the Company recorded a decrease to goodwill of $6.2 million related to 
the acquisition of PWSC from the amount recorded at December 31, 2017. 

Goodwill is assessed for impairment annually as of December 31, or more frequently if events or circumstances indicate that the 
carrying value may not be recoverable.  The Company tested goodwill for recoverability at December 31, 2018 and December 31, 
2017.  Based on the assessment performed, no goodwill impairments were recognized in 2018 and 2017.  

83

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

NOTE 13 INTANGIBLE ASSETS

Intangible assets are comprised as follows:

(in thousands)

December 31, 2018

Intangible assets subject to amortization

Database
Vehicle service agreements in-force
Customer relationships
In-place lease
Non-compete

Intangible assets not subject to amortization

Tenant relationship
Trade names

Total

(in thousands) (restated)

Intangible assets subject to amortization

Database
Vehicle service agreements in-force
Customer relationships
In-place lease

Intangible assets not subject to amortization

Tenant relationship
Trade name

Total

Gross Carrying
Value

Accumulated
Amortization

Net Carrying
Value

$

$

$

$

4,918
3,680
8,914
1,125
266

73,667
1,290
93,860

Gross Carrying
Value

4,918
3,680
3,611
1,125

73,667
663
87,664

$

$

$

$

3,013
3,671
3,691
155
64

—
—
10,594

$

$

1,905
9
5,223
970
202

73,667
1,290
83,266

December 31, 2017

Accumulated
Amortization

Net Carrying
Value

2,521
3,640
1,965
92

—
—
8,218

$

$

2,397
40
1,646
1,033

73,667
663
79,446

As further discussed in Note 5, "Acquisition," during the third quarter of 2018, the Company recorded $6.2 million of separately 
identifiable intangible assets, related to acquired customer relationships, non-compete agreement and trade name, as part of the 
acquisition of PWSC.  The customer relationships intangible asset of $5.3 million is being amortized over fifteen years based on 
the pattern in which the economic benefits of the intangible asset are expected to be consumed.  The non-compete agreement 
intangible asset of $0.3 million is being amortized on a straight-line basis over five years.  The trade name intangible asset of $0.6 
million is deemed to have an 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 seven to eighteen years.  Amortization of intangible assets was $2.4 million and $1.1 million for the years ended 
December 31, 2018 and December 31, 2017, respectively.  The estimated aggregate future amortization expense of all intangible 
assets is $1.8 million for 2019, $1.5 million for 2020, $1.4 million for 2021, $1.1 million for 2022 and $0.5 million for 2023.  

The tenant relationship and 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 2018 or 2017. 

84

 
 
KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

NOTE 14 PROPERTY AND EQUIPMENT

Property and equipment are comprised as follows:

(in thousands)

Land
Site improvements
Buildings
Leasehold improvements
Furniture and equipment
Computer hardware
Total

(in thousands)

Land
Site improvements
Buildings
Leasehold improvements
Furniture and equipment
Computer hardware

Total

$

$

$

Cost

21,120
91,308
580
104
993
4,995
119,100

Cost

21,371
91,308
968
190
1,072
4,782

$

119,691

Accumulated
Depreciation
—
$
10,161
36
102
901
4,758
15,958

$

Accumulated
Depreciation
—
$
6,028
53
117
973
4,512

$

11,683

December 31, 2018

Carrying
Value

$

$

21,120
81,147
544
2
92
237
103,142

December 31, 2017

Carrying
Value

$

21,371
85,280
915
73
99
270

$

108,008

For the years ended December 31, 2018 and December 31, 2017, depreciation expense on property and equipment of $4.3 million
and $4.3 million, respectively, is included in general and administrative expenses in the consolidated statements of operations.

NOTE 15 VEHICLE SERVICE AGREEMENT LIABILITY

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 initially recorded as deferred service fees.  
On a quarterly basis, 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 when the deferred service fees balance 
is less than expected future claims costs.  

A reconciliation of the changes in the vehicle service agreement liability, including deferred service fees related to vehicle service 
agreements, as of December 31, 2018 and December 31, 2017, were as follows:

(in thousands)

Balance at January 1, net

Gross service fees for vehicle service agreements sold

Recognition of service fees on vehicle service agreements

Liability for claims authorized on vehicle service agreements

Payments of claims authorized on vehicle service agreements

Re-estimation of deferred service fees

Balance at December 31, net

$

$

2018

40,794

$

22,556
(18,939)
5,711
(5,735)
(653)
43,734

$

2017

38,713

18,921
(16,654)
5,327
(5,377)
(136)
40,794

85

 
 
KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

The vehicle service agreement liability is presented as components of deferred services fees and accrued expenses and other 
liabilities in the consolidated balance sheets as follows:

(in thousands)

Deferred service fees

Accrued expenses and other liabilities

Balance at December 31, net

2018

43,495

239

43,734

$

$

December 31,

2017

40,531

263

40,794

$

$

NOTE 16 UNPAID LOSS AND LOSS ADJUSTMENT EXPENSES

The establishment of the provision for unpaid loss and loss adjustment expenses is based on known facts and interpretation of 
circumstances and is, therefore, a complex and dynamic process influenced by a large variety of factors.  These factors include 
the Company's experience with similar cases and historical trends involving loss payment patterns, pending levels of unpaid loss 
and loss adjustment expenses, product mix or concentration, loss severity and loss frequency patterns.

Other factors include the continually evolving and changing regulatory and legal environment; actuarial studies; professional 
experience and expertise of the Company's claims departments' personnel and independent adjusters retained to handle individual 
claims; the quality of the data used for projection purposes; existing claims management practices including claims-handling and 
settlement practices; the effect of inflationary trends on future loss settlement costs; court decisions; economic conditions; and 
public attitudes. 

Consequently, the process of determining the provision for unpaid loss and loss adjustment expenses necessarily involves risks 
that the actual loss and loss adjustment expenses incurred by the Company will deviate, perhaps materially, from the estimates 
recorded.

The Company's evaluation of the adequacy of unpaid loss and loss adjustment expenses includes a re-estimation of the liability 
for unpaid loss and loss adjustment expenses relating to each preceding financial year compared to the liability that was previously 
established. 

The results of this comparison and the changes in the provision for unpaid loss and loss adjustment expenses, net of amounts 
recoverable from reinsurers, as of December 31, 2018 and December 31, 2017, were as follows:

(in thousands)

December 31,

Balance at beginning of period, gross

Less reinsurance recoverable related to unpaid loss and loss adjustment
expenses

Balance at beginning of period, net

Incurred related to:

      Current year

      Prior years

Paid related to:

      Current year
      Prior years
Balance at end of period, net

Plus reinsurance recoverable related to unpaid loss and loss adjustment
expenses
Balance at end of period, gross

86

$

$

$

2018

1,329

72

1,257

—

1,631

—
(815)
2,073

—
2,073

$

2017

2,202

354

1,848

3

401

—
(995)
1,257

72
1,329

 
 
KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

The Company reported unfavorable development on unpaid loss and loss adjustment expenses of $1.6 million and $0.4 million
in 2018 and 2017, respectively.  The unfavorable development in 2018 and 2017 was related to an increase in loss adjustment 
expenses due to the continuing voluntary run-off of Amigo. During the second quarter of 2019, the Company agreed to settle three 
related open Amigo claims for an amount in excess of the provision for unpaid loss and loss adjustment expenses carried by the 
Company for these three open claims.   The Company estimates it will incur a net loss of approximately $0.8 million related to 
the settlement of these claims, which the Company will report in its consolidated statement of operations for the year ended 
December 31, 2019.  Original estimates are increased or decreased as additional information becomes known regarding individual 
claims.

The following tables contain information about incurred and paid loss and loss adjustment expenses development as of and for 
the year December 31, 2018, net of reinsurance, as well as cumulative claim frequency and the total of IBNR liabilities, including 
expected development on reported unpaid loss and loss adjustment expenses included within the net incurred losses and allocated 
loss adjustment expenses amounts.  The information about incurred and paid loss and loss adjustment expenses development for 
the years ended December 31, 2009 through 2017, and the average annual percentage payout of incurred claims by age as of 
December 31, 2018, is presented as supplementary information.

Non-standard automobile insurance - Private passenger auto liability
(in thousands)

Incurred Loss and Allocated Loss Adjustment Expenses, Net of Reinsurance

For the Years Ended  December 31,

Accident
Year

2009
Unaudited

2010
Unaudited

2011
Unaudited

2012
Unaudited

2013
Unaudited

2014
Unaudited

2015
Unaudited

2016
Unaudited

2017
Unaudited

2018

2009

2010

2011

2012

2013

2014

2015

2016

2017

2018

Total

35,209

37,387

38,486

40,219

40,436

40,308

40,211

40,177

40,091

40,085

47,253

51,951

55,120

54,591

54,021

53,993

53,810

53,693

53,689

29,034

29,458

28,744

28,094

27,865

27,613

27,597

27,851

13,736

13,536

13,273

12,926

12,815

12,720

13,037

6,456

6,434

5,474

4,488

4,617

4,654

—

—

—

—

—

—

—

—

—

—

—

—

—

—

—

139,316

As of  December 31,
2018

Total of
IBNR Plus
Expected
Development
on Reported
Losses

Cumulative
Number of
Reported
Claims

4

2

15

9

228

29

—

—

—

—

—

—

—

—

—

—

—

—

—

—

87

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Non-standard automobile insurance - Private passenger auto liability

(in thousands)

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

For the Years Ended  December 31,

Accident
Year

2009 
Unaudited

2010 
Unaudited

2011 
Unaudited

2012 
Unaudited

2013 
Unaudited

2014 
Unaudited

2015 
Unaudited

2016 
Unaudited

2017 
Unaudited

2018

18,742

32,436

25,659

36,390

46,356

18,456

38,796

50,591

25,296

7,060

2009

2010

2011

2012

2013

2014

2015

2016

2017

2018

39,600

51,944

26,599

11,724

3,575

40,072

52,889

27,023

12,284

4,277

—

40,089

53,451

27,378

12,530

4,437

—

—

40,087

53,484

27,431

12,618

4,496

—

—

—

40,085

53,518

27,479

12,635

4,562

—

—

—

—

40,085

53,570

27,677

12,738

4,571

—

—

—

—

—

Total

138,641

 Liabilities for non-standard automobile-private passenger auto liability unpaid loss and allocated loss adjustment expenses prior to 2009, net of
reinsurance

 Total liabilities for non-standard automobile-private passenger auto liability unpaid loss and allocated loss adjustment expenses, net of
reinsurance

Non-standard automobile insurance - Auto physical damage
(in thousands)

Incurred Loss and Allocated Loss Adjustment Expenses, Net of Reinsurance

5

680

For the Years Ended  December 31,

Accident
Year

2009 
Unaudited

2010 
Unaudited

2011 
Unaudited

2012 
Unaudited

2013 
Unaudited

2014 
Unaudited

2015 
Unaudited

2016 
Unaudited

2017 
Unaudited

2018

9,829

7,343

7,977

6,857

6,192

4,366

6,451

5,499

3,247

1,755

2009

2010

2011

2012

2013

2014

2015

2016

2017

2018

Total

6,458

5,487

3,241

1,920

1,085

6,476

5,518

3,263

1,990

996

—

6,482

5,532

3,262

2,015

1,001

—

—

6,480

5,535

3,260

2,007

999

—

—

—

6,482

5,538

3,269

2,018

1,003

—

—

—

—

6,482

5,538

3,261

1,908

988

—

—

—

—

—

18,177

88

As of  December 31,
2018

Total of
IBNR Plus
Expected
Development
on Reported
Losses

Cumulative
Number of
Reported
Claims

—

—

—

—

—

—

—

—

—

—

—

—

—

—

—

—

—

—

—

—

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Non-standard automobile insurance - Auto physical damage

(in thousands)

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

For the Years Ended  December 31,

Accident
Year

2009 
Unaudited

2010 
Unaudited

2011 
Unaudited

2012 
Unaudited

2013 
Unaudited

2014 
Unaudited

2015 
Unaudited

2016 
Unaudited

2017 
Unaudited

2009

2010

2011

2012

2013

2014

2015

2016

2017

2018

6,221

6,463

5,155

6,505

5,583

2,971

6,499

5,548

3,268

1,783

6,489

5,526

3,270

1,951

1,050

6,487

5,537

3,270

2,006

1,015

—

6,480

5,537

3,266

2,016

1,001

—

—

6,481

5,537

3,267

2,017

1,002

—

—

—

6,482

5,538

3,269

2,018

1,002

—

—

—

—

2018

6,482

5,538

3,261

1,908

988

—

—

—

—

—

 Liabilities for non-standard automobile-auto physical damage unpaid loss and allocated loss adjustment expenses prior to 2009, net of
reinsurance

 Total liabilities for non-standard automobile-auto physical damage unpaid loss and allocated loss adjustment expenses, net of reinsurance

—

—

Total

18,177

Commercial automobile
(in thousands)

Incurred Loss and Allocated Loss Adjustment Expenses, Net of Reinsurance

For the Years Ended  December 31,

Accident
Year

2009 
Unaudited

2010 
Unaudited

2011 
Unaudited

2012 
Unaudited

2013 
Unaudited

2014 
Unaudited

2015 
Unaudited

2016 
Unaudited

2017 
Unaudited

2018

10,450

6,739

8,205

7,016

8,745

8,521

7,743

9,711

9,784

9,503

2009

2010

2011

2012

2013

2014

2015

2016

2017

2018

Total

7,738

9,351

8,990

7,759

597

7,662

9,214

8,752

7,548

477

—

7,625

9,215

8,791

7,349

489

—

—

7,612

9,197

8,812

7,562

350

—

—

—

7,591

9,185

8,816

7,766

364

—

—

—

—

7,585

9,181

8,901

8,078

316

—

—

—

—

—

34,061

89

As of  December 31,
2018

Total of
IBNR Plus
Expected
Development
on Reported
Losses

Cumulative
Number of
Reported
Claims

2

26

2

163

58

26

—

—

—

—

—

—

—

—

—

—

—

—

—

—

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Commercial automobile

(in thousands)

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

For the Years Ended  December 31,

Accident
Year

2009 
Unaudited

2010 
Unaudited

2011 
Unaudited

2012 
Unaudited

2013 
Unaudited

2014 
Unaudited

2015 
Unaudited

2016 
Unaudited

2017 
Unaudited

2009

2010

2011

2012

2013

2014

2015

2016

2017

2018

3,297

5,753

4,177

6,604

7,716

5,005

7,418

8,658

7,926

5,034

7,562

8,922

8,326

6,607

299

7,606

9,069

8,533

7,028

352

—

7,595

9,149

8,638

7,150

358

—

—

7,585

9,142

8,747

7,457

358

—

—

—

7,585

9,132

8,765

7,681

358

—

—

—

—

2018

7,585

9,136

8,767

7,943

284

—

—

—

—

—

 Liabilities for commercial automobile unpaid loss and allocated loss adjustment expenses prior to 2009, net of reinsurance

 Total liabilities for commercial automobile unpaid loss and allocated loss adjustment expenses, net of reinsurance

Total

33,715

410

756

The following table reconciles the unpaid loss and allocated loss adjustment expenses, net of reinsurance presented in the tables 
above to the unpaid loss and loss adjustment expenses reported in the consolidated balance sheets at December 31, 2018 and 
December 31, 2017:

(in thousands)

December 31, 2018

December 31, 2017

Liabilities for loss and allocated loss adjustment expenses, net of reinsurance

   Non-standard automobile - private passenger auto liability

   Non-standard automobile - auto physical damage

Commercial automobile

   Other short-duration insurance lines

Liabilities for unpaid loss and allocated loss adjustment expenses, net of reinsurance

Reinsurance recoverable on unpaid loss and loss adjustment expenses

   Non-standard automobile - private passenger auto liability

   Commercial automobile

Total reinsurance recoverable on unpaid loss and loss adjustment expenses

Unallocated loss adjustment expenses

680

—

756

592

2,028

—

—

—

45

479

2

521

176

1,178

64

8

72

79

Total gross liability for unpaid loss and loss adjustment expenses

2,073

1,329

90

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

The following is supplementary information about average historical incurred loss duration as of December 31, 2018.

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

Year 1 Year 2 Year 3 Year 4 Year 5 Year 6 Year 7 Year 8 Year 9 Year 10

Non-standard automobile -
private passenger auto liability

59.6% 22.1% 10.7% 5.2% 2.0% 0.4% —% —% —% —%

Commercial automobile

70.3% 9.7% 8.9% 7.4% 3.0% 0.7% —% —% —% —%

NOTE 17 DEBT

Debt consists of the following instruments:

(in thousands)

December 31, 2018

December 31, 2017

$

Bank loan
Notes payable:
Mortgage
Flower Note
Net Lease Note
Total notes
payable

Subordinated debt
Total

$

Principal Carrying Value
3,917

3,917

$

Fair Value
3,829

$

$

Principal Carrying Value
4,917

4,917

$

Fair Value
4,864

$

173,155
7,768
9,000

189,923
90,500
284,340

$

182,548
7,768
9,000

199,316
50,023
253,256

$

174,265
8,565
9,409

192,239
50,023
246,091

$

176,136
8,179
9,000

193,315
90,500
288,732

$

186,469
8,179
9,000

203,648
52,105
260,670

$

168,477
8,825
9,870

187,172
52,105
244,141

Subordinated debt mentioned above consists of the following trust preferred debt instruments:

Issuer

Principal 
(in thousands)

Issue date

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

$

$

$

$

$

$

(a)          Bank loan:

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

On October 12, 2017, the Company borrowed a principal amount of $5.0 million from a bank at a fixed interest rate of 5.0%.  The 
bank loan matures on October 12, 2022.  The carrying value of the bank loan at December 31, 2018 of $3.9 million represents its 
unpaid principal balance.  The fair value of the bank loan disclosed in the table above is derived from quoted market prices of B 
and B minus rated industrial bonds with similar maturities. 

(b)          Notes payable:

As part of the acquisition of CMC in July 2016, the Company assumed a mortgage, which is recorded as note payable in the 
consolidated balance sheets ("the Mortgage").  The Mortgage is nonrecourse indebtedness with respect to CMC and its subsidiaries, 
and the Mortgage is not, nor will it be, guaranteed by Kingsway or its affiliates.  The Mortgage, which is recorded as note payable 
in the consolidated balance sheets, was recorded at its estimated fair value of $191.7 million, which included the unpaid principal 
amount of $180.0 million as of the date of acquisition plus a premium of $11.7 million.  The Mortgage matures on May 15, 2034 

91

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

and has a fixed interest rate of 4.07%.  The Mortgage 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 premium using the effective interest rate method.  
The fair value of the Mortgage disclosed in the table above is derived from quoted market prices of A-rated industrial bonds with 
similar maturities.

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 sheets ("the Flower Note").  The Flower Note requires monthly 
payments of principal and interest and is secured by certain investments of Flower.  The Flower Note matures on December 10, 
2031 and has a fixed interest rate of 4.81%.  The carrying value of the Flower Note at December 31, 2018 of $7.8 million 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 B rated industrial bonds with similar maturities.

On October 15, 2015, Net Lease assumed a $9.0 million mezzanine debt in conjunction with the purchase of investment real estate 
properties, which is recorded as note payable in the consolidated balance sheets ("the Net Lease Note").  The Net Lease Note 
requires monthly payments of interest and is secured by certain investments of Net Lease.  The Net Lease Note matures on November 
1, 2020 and has a fixed interest rate of 10.25%.  The carrying value of the Net Lease Note at December 31, 2018 of $9.0 million
represents its unpaid principal balance.  The fair value of the Net Lease Note disclosed in the table above is derived from quoted 
market prices of B and B minus rated industrial bonds with similar maturities.

(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 the London interbank offered interest rate for three-month U.S. dollar deposits  ("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 29, "Fair Value of Financial Instruments," 
for further discussion of the subordinated debt.  As further discussed in Note 4, "Recently Issued Accounting Standards," effective 
January 1, 2018, the Company adopted ASU 2016-01.  As a result, the portion of the change in fair value of subordinated debt 
related to the instrument-specific credit risk is now recognized in other comprehensive income (loss), whereas for 2017, the total 
change in fair value of subordinated debt was recorded in net income (loss).  Of the $2.1 million decrease in fair value of the 
Company’s subordinated debt between December 31, 2017 and December 31, 2018, $3.8 million is reported as decrease in fair 
value of debt attributable to instrument-specific credit risk in the Company's consolidated statements of comprehensive loss and 
$1.7 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, 2018, deferred interest payable of $2.5 million is included in accrued expenses and 
other liabilities in the consolidated balance sheets. 

Pursuant to indentures governing the Company’s outstanding bank loan, subordinated debt and a bank loan associated with the 
Company’s acquisition on March 1, 2019, described more fully in Note 34, "Subsequent Event," the Company is obligated to 
deliver audited financial statements for certain of its subsidiaries as of and for the year ended December 31, 2018.  Due to the 
delay in filing its 2018 Annual Report, the Company has been unable to meet these obligations, the failure of which could be 
declared events of default under the respective indentures.  As of the date of the filing of its 2018 Annual Report, none of the 
lenders or trustees responsible for administering any of our outstanding debt has declared an event of default, if required by the 
applicable indenture, notified us of an intent to accelerate any portion of the outstanding debt or charge default interest thereon, 
or pursued any other remedies available to it.  Were any of these lenders or trustees to declare an event of default, the Company 
would have a period of time to cure the default.  Now that the Company has filed its 2018 Annual Report, the Company expects 
to be in a position to deliver to the trustees the requisite audited financial statements for certain of its subsidiaries as of and for the 
year ended December 31, 2018.

92

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

NOTE 18 FINANCE LEASE OBLIGATION LIABILITY

On October 2, 2014, the Company completed a sale and leaseback transaction involving building and land located in Miami, 
Florida, which was  previously  recorded as asset  held for  sale.  The transaction did not  qualify for  sales  recognition and  was 
accounted for as a financing due to the Company's continuing involvement with the property as a result of nonrecourse financing 
provided to the buyer in the form of prepaid rent.  A finance lease obligation liability equal to the selling price of the property was 
established at the date of the transaction.  During the lease term, the Company recorded interest expense on the finance lease 
obligation at its incremental borrowing rate and increased the finance lease obligation liability by the same amount.

During the second quarter of 2017, the Company was informed of the landlord's intent to terminate the lease agreement effective 
October 10, 2017.  The Company had the option to vacate the property and effectively terminate the lease earlier than October 10, 
2017.  As a result of terminating the lease, the Company no longer had continuing involvement with the property and recognized 
the sale of the property as well as the related gain of $0.7 million during the year ended December 31, 2017.  The gain, which is 
included in non-operating other income in the consolidated statements of operations, results primarily from removing the carrying 
values of the land, building and finance lease obligation liability from the consolidated balance sheets and from the return of part 
of the original prepaid rent.  

NOTE 19 LEASES

The  Company  owns  a  parcel  of  real  property  consisting  of  approximately  192  acres  located  in  the  State  of Texas  (the  "Real 
Property") that is subject to a long-term triple net lease agreement with an unrelated third-party.  The lease provides for future rent 
escalations and renewal options.  The initial lease term ends in May 2034.  The lessee bears the cost of maintenance and property 
taxes.  Rental income from operating leases is recognized on a straight-line basis, based on contractual lease terms with fixed and 
determinable increases over the non-cancellable term of the related lease when collectability is reasonably assured.  Rental income 
includes amortization of below market lease liabilities of $0.1 million and $0.1 million for the years ended December 31, 2018
and December 31, 2017.  The estimated aggregate future amortization of below market lease liabilities is $0.1 million for 2019, 
$0.1 million for 2020, $0.1 million for 2021, $0.1 million for 2022 and $0.1 million for 2023.

Assets, which are included in property and equipment, net on the consolidated balance sheets, leased to a third-party under an 
operating lease where the Company is the lessor, are as follows: 

(in thousands)

Land
Site improvements
Buildings
Gross property and equipment leased
Accumulation depreciation
Net property and equipment leased

As of  December 31,

2018

$

$

21,120
91,308
580
113,008
(10,197)
102,811

The Company also leases certain office space under non-cancelable leases, with initial terms ranging from five to eight years, 
along with options that permit renewals for additional periods.  The Company also leases certain equipment under non-cancelable 
operating leases, with initial terms of five years.  Minimum rent is expensed on a straight-line basis over the term of the lease.

Future minimum annual lease payments and lease receipts under operating leases for the next five years and thereafter are:

(in thousands)
2019
2020
2021
2022
2023
Thereafter

$

Lease Commitments
943
$
405
404
401
401
817

Lease Receipts

11,572
11,832
12,099
12,371
12,649
149,896

93

 
KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

NOTE 20 REVENUE FROM CONTRACTS WITH CUSTOMERS

Revenue from contracts with customers relates to Extended Warranty segment service fee and commission income.  Service fee 
and commission income represents vehicle service agreement fees, GAP commissions, maintenance support service fees, warranty 
product  commissions,  homebuilder  warranty  service  fees  and  homebuilder  warranty  commissions  based  on  terms  of  various 
agreements with credit unions, consumers, businesses and homebuilders.

The following table disaggregates revenues from contracts with customers by revenue type:

(in thousands)

Vehicle service agreement fees - IWS
GAP commissions - IWS
Maintenance support service fees - Trinity
Warranty product commissions - Trinity
Homebuilder warranty service fees - PWSC
Homebuilder warranty commissions - PWSC
Service fee and commission income

Years ended December 31,
2017
2018

17,796
748
9,911
2,526
6,332
973
38,286

$

$

16,791
679
8,763
1,810
2,133
354
30,530

$

$

IWS' 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 contract fees are earned over the duration of 
the vehicle service agreement contracts as the single performance obligation is satisfied.

IWS' GAP commissions include fees collected from the sale of GAP contracts.  IWS acts as an agent on behalf of the third-party 
insurance company that underwrites and guaranties these GAP contracts.  IWS does not assume any insurance risk from the sale 
of GAP contracts.  IWS receives a single commission fee as its transaction price at the time it sells a GAP contract to a customer.  
Each GAP contract contains two separate performance obligations - sale of a GAP contract and GAP claims administration.  The 
first performance obligation is related to the sale of a GAP contract and is satisfied upon closing the sale.  The second performance 
obligation is related to the administration of claims during the GAP contract period, generally four years.

Standalone selling prices are not directly observable in the GAP contract for each of the separate performance obligations.  As a 
result, IWS 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.

For the model related to the sale of a GAP contract performance obligation, IWS makes judgments about which of its actual costs 
are associated with selling activities.  For the model related to the GAP claims administration performance obligation, IWS makes 
judgments about which of its actual costs are associated with claim-handling activities, which are performed over the life of the 
GAP contract period.  The relative percentage of expected costs plus a margin associated with the sale of a GAP contract performance 
obligation is applied to the transaction price to determine the estimated standalone selling price of the sale of a GAP contract 
performance obligation, which IWS recognizes as earned at the time of the GAP contract sale.  The relative percentage of expected 
costs plus a margin associated with the GAP claims administration performance obligation is applied to the transaction price to 
determine the estimated standalone selling price of the GAP claims administration performance obligation, which IWS recognizes 
as earned as services are performed over the GAP contract period.

For the GAP claims administration performance obligation, IWS 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 GAP contract period.  IWS uses historical 
data regarding the number of claims it receives and activities performed, in addition to the number of GAP contracts sold, to 
estimate the number of claims to be received by year until coverage expires, which allows IWS to develop a revenue recognition 
pattern  that  it  believes  provides  a  faithful  depiction  of  the  transfer  of  services  over  time  for  the  GAP  claims  administration 
performance obligation.

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

94

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Trinity’s 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 refrigeration equipment.    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.  Warranty product commissions are earned at the 
time of the warranty product sales. 

PWSC’s homebuilder warranty service fees include fees collected from the sale of warranties issued by new homebuilders.  PWSC 
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 performance obligations.  As a result, 
PWSC 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.  

For the model related to the warranty administrative services performance obligation, PWSC 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, PWSC 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 PWSC 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 
PWSC recognizes as earned as services are performed over the warranty coverage period.  

For the other warranty services performance obligation, PWSC 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.  PWSC 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 
PWSC 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.

PWSC’s 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.  PWSC 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, and a profit-sharing bonus on eligible warranties, which is determined based on expected ultimate loss ratio 
targets and is earned at the time the profit-sharing bonus is received.

Receivables from contracts with customers are reported as service fee receivable, net in the consolidated balance sheets and at 
December 31, 2018 and December 31, 2017 were $3.4 million and $4.4 million, respectively.

The Company records deferred service fees resulting from contracts with customers when payment is received in advance of 
satisfying the performance obligations.  The Company expects to recognize within one year as service fee and commission income 
approximately 34.3% of the deferred service fees as of December 31, 2018.  Approximately $16.0 million of service fee and 
commission income recognized during the year ended December 31, 2018 was included in deferred service fees as of December 
31, 2017.

95

 
KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

NOTE 21 INCOME TAXES

The Company and its non-U.S. subsidiaries file separate foreign income tax returns.  Kingsway America Agency Inc. files a separate 
U.S. federal income tax return.  Kingsway America II Inc. and its eligible U.S. subsidiaries file a U.S. consolidated federal income 
tax return ("KAI Tax Group").  The method of allocating federal income taxes among the companies in the KAI 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 U.S. consolidated federal income tax 
return.  The Company's U.S. subsidiaries not included in the KAI Tax Group file separate U.S. federal income tax returns.  As a 
result of its domestication to the U.S. on December 31, 2018, the Company will no longer file foreign income tax returns in 2019 
and later years.  Starting in 2019, the Company and all of its eligible U.S. subsidiaries will file a U.S. consolidated federal income 
tax return.   

The Tax Cuts and Jobs Act (the "Tax Act") was enacted on December 22, 2017.  The Tax Act made broad and complex changes 
to the U.S. tax code, including, but not limited to, (1) a permanent reduction in the U.S. federal corporate income tax rate to 21%
and (2) eliminating the corporate alternative minimum tax ("AMT") and changing how existing AMT credits can be realized.

The Company is subject to the provisions of the ASC 740-10, Income Taxes, which requires that the effect on deferred income tax 
assets and liabilities of a change in tax rates be recognized in the period the tax rate change was enacted.  In December of 2017, 
the SEC staff issued Staff Accounting Bulletin 118 ("SAB 118"), which provides that companies that have not completed their 
accounting for the effects of the Tax Act but can determine a reasonable estimate of those effects should include a provisional 
amount based on their reasonable estimate in their financial statements.

Pursuant to SAB 118, the Company recorded provisional amounts for the estimated income tax effects of the Tax Act on deferred 
income taxes.  The Company estimated that (1) the reduction in the corporate income tax rate decreased its net deferred income 
tax liability as of December 31, 2017 by $18.0 million and (2) the change in the AMT credit rules allowed the Company to reduce 
its valuation allowance against its gross deferred income tax assets by $0.1 million, for a combined Tax Act total of $18.1 million. 
The $18.1 million Tax Act amount was recorded as a decrease to income tax expense in the Company’s consolidated statements 
of operations for the year ended December 31, 2017.  In addition, as result of the reduction in the corporate income tax rate, the 
Company provisionally reduced its December 31, 2017 net deferred income tax asset balance and the related net deferred income 
tax valuation allowance by $105.6 million, the net effect of which had no impact on the Company’s consolidated statements of 
operations for the year ended December 31, 2017. 

Although the $18.1 million tax benefit represented what the Company believed was a reasonable estimate of the impact of the 
income tax effects of the Tax Act on the Company’s Consolidated Financial Statements as of December 31, 2017, it was considered 
provisional.  In the fourth quarter of 2018, the Company finalized its calculation of the income tax effects of the Tax Act on its 
deferred income taxes by recording an additional tax benefit of $0.1 million.

Income tax expense (benefit) consists of the following: 

(in thousands)

Current income tax expense
Deferred income tax benefit
Income tax expense (benefit)

Years ended December 31,
2017

2018

$

$

423
(108)
315

$

$

628
(17,316)
(16,688)

96

  
KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Income tax expense (benefit) varies from the amount that would result by applying the applicable U.S. corporate income tax rate 
of 21% in 2018 and 34% in 2017 to loss from continuing operations before income tax expense (benefit).  The following table 
summarizes the differences:

(in thousands)

Income tax benefit at U.S. statutory income tax rate
Tax Act adjustment
Valuation allowance
Indefinite life intangibles
Change in unrecognized tax benefits
Compensation
Investment income
Other
Income tax expense (benefit) for continuing operations

$

$

$

Years ended December 31,
2017
(4,255)
(18,052)
3,169
1,173
490
403
—
384
(16,688)

2018
(4,609)
(82)
4,562
92
233
(470)
747
(158)
315

$

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
Other
Valuation allowance
Deferred income tax assets
Deferred income tax liabilities:
Indefinite life intangibles
Depreciation and amortization
Fair value of debt
Land
Investments
Deferred acquisition costs
Other

Deferred income tax liabilities
Net deferred income tax liabilities

$

$

$

$
$

2018

180,012
1,670
2,538
1,017
841
727
783
693
(171,456)
16,825

(16,660)
(16,121)
(6,528)
(4,435)
(168)
(1,450)
—
(45,362)
(28,537)

December 31,

2017

185,574
1,513
2,484
988
758
807
183
21
(173,965)
18,363

(16,436)
(16,971)
(5,894)
(4,435)
(1,853)
(1,328)
(209)
(47,126)
(28,763)

$

$

$

$
$

The Company maintains a valuation allowance for its gross deferred income tax assets of $171.5 million (U.S. operations - $171.5 
million; Other - $0.0 million) and $174.0 million (U.S. operations - $167.6 million; Other - $6.4 million) at December 31, 2018
and December 31, 2017, 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, 2018 and December 31, 2017
net deferred income tax assets, excluding the deferred income tax liability, deferred state income tax assets, and deferred income 
tax assets relating to AMT credit amounts set forth in the paragraph below.  In 2018 and 2017, the Company released into income 
zero and $0.4 million, respectively, of its valuation allowance, as a result of its acquisition of CMC, 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.

97

 
KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

The Company carries net deferred income tax liabilities of $28.5 million at December 31, 2018, $8.0 million of which relates to 
deferred income tax liabilities that are scheduled to reverse in periods after the expiration of the KAI Tax Group's consolidated 
U.S. net operating loss carryforwards, $21.1 million of which relates to deferred income tax liabilities related to land and indefinite 
life intangible assets, $0.5 million of which relates to deferred state income tax assets, and $0.1 million of which relates to deferred 
income tax assets relating to AMT credits. The Company carries net deferred income tax liabilities of $28.8 million at December 31, 
2017, $8.0 million of which relates to deferred income tax liabilities that are scheduled to reverse in periods after the expiration 
of the KAI Tax Group's consolidated U.S. net operating loss carryfowards, $20.9 million of which relates to deferred income tax 
liabilities related to land and indefinite life intangible assets, and $0.1 million of which relates to deferred income tax assets relating 
to AMT credits. The Company considered a tax planning strategy in arriving at its December 31, 2018 and December 31, 2017
net deferred income tax liabilities.

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 KAI Tax Group's consolidated U.S. net operating loss carryforwards, totaling 
$845.7 million, are as follows:

Year of net operating loss
2007
2008
2009
2010
2011
2012
2013
2014
2016
2017

Expiration date
2027
2028
2029
2030
2031
2032
2033
2034
2036
2037

Net operating loss
(in thousands)
53,909
53,696
506,552
85,215
42,189
32,152
29,913
6,932
15,517
19,628

In addition, not reflected in the table above, are net operating loss carryforwards of (i) $6.5 million relating to separate U.S. tax 
returns, which losses will expire over various years through 2037 and (ii) $1.6 million, relating to operations in Barbados which 
losses will expire over various years through 2027.

A reconciliation of the beginning and ending unrecognized tax benefits, exclusive of interest and penalties, is as follows:

(in thousands)

Unrecognized tax benefits - beginning of year
Gross additions - current year tax positions
Gross additions - prior year tax positions
Gross reductions - prior year tax positions
Gross reductions - settlements with taxing authorities
Impact due to expiration of statute of limitations

Unrecognized tax benefits - end of year

2018
1,367
—
14
—
—
—
1,381

$

$

December 31,

2017
1,274
—
93
—
—
—
1,367

$

$

The amount of unrecognized tax benefits that, if recognized as of December 31, 2018 and December 31, 2017 would affect the 
Company's effective tax rate, was an expense of $0.2 million and $0.5 million, respectively.

As of December 31, 2018 and December 31, 2017, the Company carried a liability for unrecognized tax benefits of $1.4 million
and $1.4 million, 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.    During  the  years  ended 
December 31, 2018 and December 31, 2017, the Company recognized an expense for interest and penalties of $0.2 million and 

98

 
KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

$0.5 million, respectively.  At December 31, 2018 and December 31, 2017, the Company carried an accrual for the payment of 
interest and penalties of $1.1 million and $0.9 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 2014 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 2013 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 22 LOSS FROM CONTINUING OPERATIONS PER SHARE

The following table sets forth the reconciliation of numerators and denominators for the basic and diluted loss from continuing 
operations per share computation for the years ended December 31, 2018 and December 31, 2017:

(in thousands, except per share data)

Numerator:

(Loss) income from continuing operations

Less: net income attributable to noncontrolling interests

Less: dividends on preferred stock, net of tax

Loss from continuing operations attributable to common shareholders

Denominator:

Weighted average basic shares

Weighted average common shares outstanding

Weighted average diluted shares

Weighted average common shares outstanding

Effect of potentially dilutive securities

Total weighted average diluted shares

Basic loss from continuing operations per share

Diluted loss from continuing operations per share

Years ended December 31,

2018

2017

(restated)

$

$

$

$

$

(22,264)
(1,765)
(620)

(24,649)

$

21,728

21,728

—

21,728

(1.13)

(1.13)

$

$

4,174
(4,085)
(1,248)

(1,159)

21,547

21,547

—

21,547

(0.05)

(0.05)

Basic loss from continuing operations per share is calculated using weighted-average common shares outstanding.  Diluted loss 
from continuing operations 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 consist of stock options, unvested restricted stock awards, unvested restricted stock units, warrants and convertible 
preferred stock.  Because the Company is reporting a loss from continuing operations attributable to common shareholders for 
the years ended December 31, 2018 and December 31, 2017, 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.

NOTE 23 STOCK-BASED COMPENSATION

(a)  

Stock Options

On May 13, 2013, the Company's shareholders approved the 2013 Equity Incentive Plan ("2013 Plan").  The 2013 Plan replaced 
the Company's previous Amended and Restated Stock Option Plan ("Prior Plan"), with respect to the granting of future equity 
awards.  Under the 2013 Plan, the Company reserved for issuance to key employees selected by the Company new stock options 
("New Stock Options") to purchase up to an additional 300,000 common shares.  No New Stock Options were granted during the 
year ended December 31, 2018.  There are no New Stock Options remaining for future grants. 

On May 13, 2013, the Company's shareholders also approved the Option Exchange Program whereby the outstanding stock options 
under the Prior Plan held by current employees will be canceled and replaced with stock options granted under the 2013 Plan 

99

 
KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

("Replacement Options").  The maximum number of common shares available to be granted as Replacement Options is 355,625.  
No Replacement Options were granted during the year ended December 31, 2018.  There are no Replacement Options remaining 
for future grants.  

The Replacement Options and New Stock Options (collectively, the "Stock Options") are fully vested and exercisable at the date 
of grant and are exercisable for a period of four years. 

The following table summarizes the stock option activity during the year ended December 31, 2018:  

Number of
Options
Outstanding

Weighted-
Average
Exercise Price

Outstanding at December 31, 2017

651,875

$

Granted

Exercised

Expired 

Outstanding at December 31, 2018

Exercisable at December 31, 2018

—

—

(611,875)

40,000

40,000

$

$

4.51

—

—

4.50

4.67

4.67

Weighted-
Average
Remaining
Contractual
Term (in years)

Aggregate 
Intrinsic Value 
(in thousands)

0.4

$

352

1.3

1.3

$

$

—

—

The aggregate intrinsic value of stock options outstanding and exercisable is the difference between the December 31, 2018 market 
price for the Company's common shares and the exercise price of the options, multiplied by the number of options where the fair 
value exceeds the exercise price. 

At December 31, 2018 and December 31, 2017 the number of options exercisable was 40,000 and 651,875 respectively, with 
weighted average prices of $4.67 and $4.51, respectively.  No options were exercised during the years ended December 31, 2018 
and December 31, 2017.

The Company uses the Black-Scholes option pricing model to estimate the fair value of each option on the date of grant.  No 
options were granted during the years ended December 31, 2018 and December 31, 2017. 

(b)  

Restricted Stock Awards of the Company

Under the 2013 Plan, the Company made grants of restricted common stock awards to certain officers of the Company on March 
28, 2014 (the "2014 Restricted Stock Awards").  The 2014 Restricted Stock Awards shall become fully vested and the restriction 
period shall lapse as of March 28, 2024 subject to the officers' continued employment through the vesting date.  The 2014 Restricted 
Stock Awards are amortized on a straight-line basis over the ten-year requisite service period.  The grant-date fair value of the 
2014 Restricted Stock Awards was determined using the closing price of Kingsway common stock on the date of grant.  Total 
unamortized compensation expense related to unvested 2014 Restricted Stock Awards at December 31, 2018 was $0.7 million.  

During the third quarter of 2018, the Company modified the terms of the 2014 Restricted Stock Awards for two of its officers.

On September 5, 2018, the Company executed an Amended and Restated Restricted Stock Award Agreement ("Amended RSA 
Agreement") with its former Chief Executive Officer.  Under the terms of the Amended RSA Agreement, the former Chief Executive 
Officer was deemed to have forfeited 1,382,665 shares of the 2014 Restricted Stock Awards.  The Company’s accounting policy 
is to account for forfeitures when they occur.  As a result, the Company reversed during the third quarter of 2018 $2.4 million of 
compensation expense previously recognized from March 28, 2014 through June 30, 2018.

Pursuant to the terms of the Amended RSA Agreement, the Company granted to the former Chief Executive Officer a modified 
award of 350,000 shares of restricted common stock (the "2018 Modified Restricted Stock Award").  The Company deemed the 
2018 Modified Restricted Stock Award to be taxable to the former Chief Executive Officer on the modification date.  Pursuant to 
the terms of the 2013 Plan and the Amended RSA Agreement, the former Chief Executive Officer was entitled to satisfy the tax 
withholding obligation by authorizing the Company to withhold restricted common shares, which would otherwise be deliverable, 
having an aggregate fair market value, determined as of the tax date, equal to the tax withholding obligation.  The former Chief 
Executive Officer chose to satisfy the tax withholding obligation in this manner.  As a result, the Company cancelled 102,550 of 

100

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

the 350,000 shares of the 2018 Modified Restricted Stock Award and recognized payroll tax expense of $0.3 million during the 
third quarter of 2018.

The remaining 247,450 shares of the 2018 Modified Restricted Stock Award shall become fully vested after the satisfaction of 
certain performance conditions, as defined in the Amended RSA Agreement.  There is no defined term under which the performance 
conditions must be completed.  The unamortized compensation expense for the 2018 Modified Restricted Stock Award will be 
recognized at the time the performance condition has been satisfied.  The grant-date fair value of the 2018 Modified Restricted 
Stock Award was determined using the closing price of Kingsway common stock on the modification date.  Total unamortized 
compensation expense related to the unvested 2018 Modified Restricted Stock Award at December 31, 2018 was $0.6 million. 

On September 15, 2018, the Company executed an Employee Separation Agreement and Release ("Separation Agreement") with 
a former officer.  Under the terms of the Separation Agreement, the former officer forfeited 112,500 shares of the 2014 Restricted 
Stock Awards.  The Company’s accounting policy is to account for forfeitures when they occur.  As a result, the Company reversed 
during the third quarter of 2018 $0.4 million of compensation expense previously recognized from March 28, 2014 through June 
30, 2018.

The Separation Agreement modified the vesting terms related to the remaining 112,500 shares of the original 2014 Restricted 
Stock Awards ("Modified Restricted Stock Award"), such that they became fully vested on September 22, 2018.  The Company 
deemed the Modified Restricted Stock Award to be taxable to the former officer on the vesting date.  Pursuant to the terms of the 
2013 Plan and the Separation Agreement, the former officer was entitled to satisfy the tax withholding obligation by authorizing 
the Company to withhold restricted common shares, which would otherwise be deliverable, having an aggregate fair market value, 
determined as of the tax date, equal to the tax withholding obligation.  The former officer chose to satisfy the tax withholding 
obligation in this manner.  As a result, the Company cancelled 32,962 of the 112,500 shares of the Modified Restricted Stock 
Award and recognized payroll tax expense of $0.1 million during the third quarter of 2018. 

The Company also recorded during the third quarter of 2018 $0.2 million of compensation expense equal to the fair value of the 
remaining 79,538 fully vested shares of the Modified Restricted Stock Award.  The grant-date fair value of the Modified Restricted 
Stock Award was determined using the closing price of Kingsway common stock on the modification date.  Total unamortized 
compensation expense related to the unvested Modified Restricted Stock Award at December 31, 2018 was zero.

The Company granted restricted common stock units ("Restricted Stock Units") to an officer of the Company pursuant to a Restricted 
Stock Unit Agreement dated August 24, 2016.  On September 5, 2018, the Restricted Stock Unit Agreement was cancelled and 
500,000 restricted common stock awards were granted to the officer (the "2018 Restricted Stock Award").  There was no change 
to the vesting terms.  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, 2018 was $2.0 million.

The following table summarizes the activity related to unvested 2014 Restricted Stock Awards, 2018 Modified Restricted Stock 
Award, Modified Restricted Stock Award and 2018 Restricted Stock Award (collectively "Restricted Stock Awards") during the 
year ended December 31, 2018:

Unvested at December 31, 2017

Granted

Vested

Cancelled for Tax Withholding

Forfeited

Unvested at December 31, 2018

Number of Restricted
Stock Awards

Weighted-Average
Grant Date Fair Value
(per Share)

1,952,665

$

850,000
(79,538)
(135,512)
(1,495,165)
1,092,450

$

4.14

4.42

2.95

2.65

4.14

4.51

101

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

The unvested balance at December 31, 2018 in the table above is comprised of 345,000 shares of 2014 Restricted Stock Awards, 
247,450 shares of 2018 Modified Restricted Stock Award and 500,000 shares of the 2018 Restricted Stock Award.

(c)  

Restricted Stock Awards of PWSC

PWSC granted 1,000 restricted common stock awards ("PWSC Restricted Stock Award") to an officer of PWSC pursuant to an 
agreement dated September 7, 2018. The PWSC Restricted Stock Award contains both a service and a performance condition that 
affects vesting.  The service condition vests according to a graded vesting schedule and shall become fully vested on February 20, 
2022 subject to the officer's continued employment through the applicable vesting dates.   The service condition component of the 
PWSC Restricted Stock Award is amortized on a straight-line basis over the requisite service period.  The performance condition 
vests  on  February  20,  2022  and  is  based  on  the  internal  rate  of  return  of  PWSC.   Accruals  of  compensation  expense  for  the 
performance  condition  component  of  the  PWSC  Restricted  Stock Award  is  estimated  based  on  the  probable  outcome  of  the 
performance condition.  The grant-date fair value of the PWSC Restricted Stock Award was estimated using a valuation model.  
At December 31, 2018, there were 1,000 unvested shares of the PWSC Restricted Stock Award with a weighted-average grant 
date fair value of $824.47 per share.  Total unamortized compensation expense related to unvested PWSC Restricted Stock Award 
at December 31, 2018 was $0.7 million.

(d)  

Restricted Stock Units

The Company granted Restricted Stock Units to an officer of the Company pursuant to a Restricted Stock Unit Agreement dated 
August 24, 2016.  As discussed above, on September 5, 2018, the Restricted Stock Unit Agreement was cancelled. The following 
table summarizes the activity related to unvested Restricted Stock Units for the year ended December 31, 2018:

Unvested at December 31, 2017

Granted

Vested

Cancelled

Unvested at December 31, 2018

Number of Restricted
Stock Units

Weighted-Average
Grant Date Fair Value
(per Share)

500,000

$

—

—
(500,000)

— $

5.73

—

—

5.73

—

Total stock-based compensation, net of forfeitures, was a benefit of $1.7 million and an expense of $1.2 million for the years ended 
December 31, 2018 and December 31, 2017, respectively.

(d)  

Employee Share Purchase Plan

The Company has an employee share purchase plan ("ESPP Plan") whereby qualifying employees could 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, 2018 and December 31, 2017 totaled $0.1 million and $0.1 million, respectively.

NOTE 24 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 $18,500 and $18,000
in 2018 and 2017, respectively.  The Company matches an amount equal to 50% of each participant's contribution, limited to 
contributions up to 5% of a participant's earnings.

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, 2018 and December 31, 2017 totaled $0.2 million and $0.1 
million, respectively.  All Company obligations to the plans were fully funded as of December 31, 2018.

102

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

NOTE 25 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 will 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 will have priority over the common shares.

There were 222,876 shares of Class A preferred stock ("Preferred Shares") outstanding at December 31, 2018 and December 31, 
2017.  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 April 1, 2021.  As of December 31, 2018, the maximum number of common shares issuable upon 
conversion of the Preferred Shares is 1,392,975 common shares. 

During 2017, 40,000 Preferred Shares were converted into 250,000 common shares at the conversion price of $4.00 per common 
share, or $1.0 million, at the option of the holders.  As a result, $1.0 million was reclassified from Class A preferred stock to 
Shareholders' Equity on the consolidated balance sheet at December 31, 2017.  

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 April 1, 2021, 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.  At December 31, 2018 and December 31, 
2017, accrued dividends of $1.7 million and $1.6 million were included in Class A preferred stock in the consolidated balance 
sheets.  The redemption amount of the Preferred Shares as if they were currently redeemable was $7.3 million and $7.2 million 
at December 31, 2018 and December 31, 2017, respectively.

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 on April 1, 2021.  As such, the Preferred Shares are presented in 
temporary or mezzanine equity on the consolidated balance sheets and will be accreted, using the interest method, up to the stated 
redemption value of $5.6 million, through additional paid-in capital as a deemed dividend, from the date of issuance through the 
April 1, 2021 redemption date.   The Company also accrues dividends through additional paid-in-capital at the stated coupon, 
which the Company expects will total $2.6 million as of the April 1, 2021 redemption date.  As a result, the total redemption amount 
of the Preferred Shares as of the redemption date if the Preferred Shares are not converted is expected to be $8.2 million.

NOTE 26 SHAREHOLDERS' EQUITY

The Company is authorized to issue an unlimited number of zero par value common stock.  There were 21,787,728 and 21,708,190 
shares of common stock outstanding at December 31, 2018 and December 31, 2017, respectively.

There were no dividends declared during the years ended December 31, 2018 and December 31, 2017.

As described in Note 25, "Redeemable Class A Preferred Stock", during 2017, 40,000 Preferred Shares were converted into 250,000
common shares.  As a result, $1.0 million was reclassified from Class A preferred stock to Shareholders' Equity on the consolidated 
balance sheet at December 31, 2017. 

103

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

The Company has warrants outstanding, recorded in shareholders' equity, that will entitle each subscriber to purchase one common 
share of Kingsway for each warrant.  The following table summarizes information about warrants outstanding at December 31, 
2018:

Exercise Price

$
$

5.00
5.00

Date of Issue
16-Sep-13
3-Feb-14

Expiry Date
15-Sep-23
15-Sep-23

Total:

Remaining Contractual
Life (in years)
4.7
4.7
4.7

NOTE 27 ACCUMULATED OTHER COMPREHENSIVE INCOME (LOSS)

December 31, 2018

Number
Outstanding

3,280,790
1,392,975
4,673,765

The table below details the change in the balance of each component of accumulated other comprehensive income (loss), net of 
tax, for the years ended December 31, 2018 and December 31, 2017 as relates to shareholders' equity attributable to common 
shareholders on the consolidated balance sheets.  On the other hand, the consolidated statements of comprehensive loss present 
the components of other comprehensive income (loss), net of tax, only for the years ended December 31, 2018 and December 31, 
2017 and inclusive of the components attributable to noncontrolling interests in consolidated subsidiaries.

As further discussed in Note 4, "Recently Issued Accounting Standards," effective January 1, 2018, the Company adopted ASU 
2016-01.  As a result of the adoption, equity investments are no longer classified as available-for-sale with unrealized gains and 
losses recognized in other comprehensive income (loss); rather, changes in the fair value of equity investments are now recognized 
in net income (loss).  Also as a result of the adoption, the portion of the total change in the fair value of our subordinated debt 
resulting from the change in instrument-specific credit risk is no longer recognized in net income (loss) and is now presented in 
other comprehensive income (loss).  Prior periods have not been restated to conform to the current presentation.

104

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

(in thousands)

Balance, January 1, 2017

Other comprehensive loss arising during
the period

Amounts reclassified from accumulated
other comprehensive loss

Net current-period other comprehensive
(loss) income

Balance, December 31, 2017

Cumulative effect of adoption of ASU
2016-01

Balance at January 1, 2018, as adjusted

Other comprehensive income (loss)
arising during the period

Amounts reclassified from accumulated
other comprehensive income

Amounts removed from accumulated
other comprehensive income due to
disposal of discontinued operations

Net current-period other comprehensive
income (loss)

Balance, December 31, 2018

$

$

$

$

Unrealized
Gains
(Losses) on
Available-
for-Sale
Investments

$

3,572

Foreign
Currency
Translation
Adjustments
(3,780)

$

Change in
Fair Value
of Debt
Attributable
to
Instrument-
Specific
Credit Risk

Equity in Other
Comprehensive
Loss of Limited
Liability
Investment

Total
Accumulated
Other
Comprehensive
Income (Loss)

— $

— $

(208)

(5,214)

1,076

(4,138)

—

494

494

—

—

—

—

—

—

(5,214)

1,570

(3,644)

(566) $

(3,286) $

— $

— $

(3,852)

40

(526) $

—
(3,286) $

40,455

40,455

$

—

— $

40,495

36,643

13

(18)

371

—

—

—

3,804

(45)

3,772

—

—

—

—

(18)

371

366

$

— $

3,804

(160) $

(3,286)

44,259

$

$

(45) $

4,125

(45) $

40,768

105

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Components of accumulated other comprehensive income (loss) were reclassified to the following lines of the consolidated 
statements of operations for the years ended December 31, 2018 and December 31, 2017:

(in thousands)

Reclassification of accumulated other comprehensive income (loss) from
unrealized gains (losses) on available-for-sale investments to:

Net realized (losses) gains

Other-than-temporary impairment loss

$

Loss from continuing operations before income tax expense (benefit)

Income tax expense (benefit)

Income (loss) from discontinued operations, net of taxes
Net income (loss)

Reclassification of accumulated other comprehensive income (loss) from foreign
currency translation adjustments to:

Loss on liquidation of subsidiary, net of taxes
Income tax expense (benefit)

Net loss
Total reclassification from accumulated other comprehensive income (loss) to net
loss

NOTE 28 SEGMENTED INFORMATION

Years ended December 31,

2018

2017

$

18

—

18

—

—
18

—
—
—

(2)
—
(2)
—
(1,074)
(1,076)

(494)
—
(494)

$

18

$

(1,570)

The Company conducts its business through the following two reportable segments: Extended Warranty and Leased Real Estate. 

Prior to the second quarter of 2018, the Company conducted its business through a third reportable segment, Insurance Underwriting.  
Insurance Underwriting included the following subsidiaries of the Company: Mendota, Amigo and Kingsway Re.  As further 
discussed in Note 6, "Disposal, Discontinued Operations and Liquidation," on October 18, 2018, the Company announced that it 
had completed the sale of Mendota.  As a result, Mendota has been classified as discontinued operations and the results of their 
operations are reported separately for all periods presented.  As a result of classifying Mendota as discontinued operations, the 
composition of the Insurance Underwriting segment has changed such that it no longer meets the criteria of a reportable segment.  
As such, all segmented information has been restated to exclude the Insurance Underwriting segment for all periods presented. 

Extended Warranty Segment

Extended  Warranty  includes  the  following  subsidiaries  of  the  Company:    IWS,  Trinity  and  PWSC  (collectively,  "Extended 
Warranty"). 

IWS is a licensed motor vehicle service agreement company and is a provider of after-market vehicle protection services distributed 
by credit unions in 23 states and the District of Columbia to their members.

Trinity sells HVAC, standby generator, commercial LED lighting and 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 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.

106

  
KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

PWSC sells new 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.

Leased Real Estate Segment

Leased Real Estate includes the Company's subsidiary, CMC.  CMC owns the Real Property that is leased to a third-party pursuant 
to a long-term triple net lease with a single customer.  For the year ended December 31, 2018, revenue of $13.4 million from this 
single customer represents more than 10% of the Company’s consolidated revenues.  The Real Property is also subject to the 
Mortgage.  When assessing and measuring the operational and financial performance of the Leased Real Estate segment, interest 
expense related to the Mortgage is included in Leased Real Estate's segment operating income. 

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, 2018 and December 31, 
2017 were:

(in thousands)

Revenues:

Extended Warranty:

Years ended December 31,
2017
2018
(restated)

Service fee and commission income

$

38,286

$

Other income

Total Extended Warranty

Leased Real Estate:

Rental income

Other income

Total Leased Real Estate

Total segment revenues

Rental income not allocated to segments

Total revenues

171

38,457

13,366

245

13,611

52,068

10

$

52,078

$

30,530

191

30,721

13,364

493

13,857

44,578

20

44,598

107

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 (loss) income from continuing operations for the years ended 
December 31, 2018 and December 31, 2017 were:

(in thousands)

Segment operating income

Extended Warranty

Leased Real Estate

Total segment operating income

Net investment income

Net realized (losses) gains

Gain on change in fair value of equity investments

Loss on change in fair value of limited liability investments, at fair value

Net change in unrealized loss on private company investments

Interest expense not allocated to segments

Other income and expenses not allocated to segments, net

Amortization of intangible assets

Contingent consideration benefit

Loss on change in fair value of debt

Gain on disposal of subsidiary

Equity in net (loss) income of investee

Loss from continuing operations before income tax expense (benefit)

Income tax expense (benefit)

(Loss) income from continuing operations

Years ended December 31,
2017
2018
(restated)

4,215

2,485

6,700

2,957
(17)
381
(7,393)
(1,629)
(7,407)
(8,963)
(2,376)
—
(1,720)
17
(2,499)
(21,949)
315
(22,264)

$

$

3,680

3,099

6,779

7,087

306

—
(1,832)
(758)
(6,348)
(10,503)
(1,085)
212
(8,487)
—

2,115
(12,514)
(16,688)
4,174

$

$

NOTE 29 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.

108

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

•  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.

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  and  subordinated  debt  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 Company's investment in 1347 
Investors as well as the underlying investments of Net Lease and Argo Holdings. 1347 Investors owns common stock in Limbach 
Holdings,  Inc.,  a  publicly  traded  company.  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 the Company's investment in 1347 Investors is calculated based on a model that distributes the net equity 
of 1347 Investors to all classes of membership interests. The model uses quoted market prices and significant market 
observable inputs.  This investment is categorized in Level 2 of the fair value hierarchy. 

•  The fair value of Net Lease's investments in limited liability companies is based upon the net asset values of the underlying 
investments 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.

109

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

•  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.

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.

Contingent consideration - The consideration for certain of the Company's acquisitions included future payments to the former 
owners that were contingent upon the achievement of certain targets over future reporting periods.  Liabilities for contingent 
consideration were measured and reported at fair value and were included in accrued expenses and other liabilities in the consolidated 
balance sheets.  The fair value of contingent consideration liabilities was estimated using internal models without relevant observable 
market inputs.  Estimated payments were discounted using present value techniques to arrive at estimated fair value.  Contingent 
consideration liabilities were 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 were reported in the consolidated statements of operations as contingent 
consideration benefit.  During the second quarter of 2017, the Company settled its remaining contingent consideration liability; 
therefore, no contingent consideration liability remains on the consolidated balance sheets as of as of December 31, 2018 and 
December 31, 2017.

110

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, 2018 and December 31, 2017 was 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)

December 31, 2018

Fair Value Measurements at the End of the Reporting Period Using

Quoted Prices
in Active
Markets for
Identical
Assets(Level 1)

Significant
Other
Observable
Inputs
(Level 2)

Total

Significant
Unobservable
Inputs (Level 3)

Measured at
Net Asset
Value

Recurring fair value

Assets:
Fixed maturities:

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

Equity investments:
Common stock
Warrants
Total equity investments
Limited liability investments, at
fair value
Real estate investments
Other investments
Short-term investments
Total assets

Liabilities:

Subordinated debt

Total liabilities

—

—
—
—
—

—
—
—

21,685

—
—
—
—

—
—
—

4,124
10,662
—
—
14,786

$

21,685

— $
— $

—
—

$

5,547

$

— $

5,547

$

— $

607
3,186
2,920
12,260

801
55
856

26,015
10,662
2,079
152
52,024

50,023
50,023

$

$
$

$

$
$

—
—
—
—

801
19
820

—
—
—
—
820

$

— $
— $

607
3,186
2,920
12,260

—
36
36

206
—
2,079
152
14,733

50,023
50,023

$

$
$

111

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

(in thousands) (restated)

December 31, 2017

Fair Value Measurements at the End of the Reporting Period Using

Quoted Prices
in Active
Markets for
Identical Assets
(Level 1)

Significant
Other
Observable
Inputs
(Level 2)

Total

Significant
Unobservable
Inputs(Level 3)

Measured 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

Corporate

Total fixed maturities

Equity investments:

        Common stock

        Warrants

        Total equity investments

Limited liability investments, at
fair value

Real estate investments

Other investments

Short-term investments

Total assets

Liabilities:

Subordinated debt

Total liabilities

$

5,612

$

— $

5,612

$

— $

626

2,876

5,427

14,541

3,570

1,019

4,589

32,211

10,662

3,721

151

—

—

—

—

3,570

171

3,741

—

—

—

—

626

2,876

5,427

14,541

—

848

848

10,314

—

3,721

151

—

—

—

—

—

—

—

—

—

—

—

—

—

—

—

1,397

10,662

—

—

20,500

—

—

—

$

$

$

65,875

$

3,741

$

29,575

$

12,059

$

20,500

52,105

52,105

$

$

— $

— $

52,105

52,105

$

$

— $

— $

—

—

112

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, 2018 and December 31, 2017:

(in thousands)

Assets:

Limited liability investments, at fair value:

Beginning balance

Purchases

Distributions received

Change in fair value of limited liability investments, at fair value included
in net loss

Ending balance

Real estate investments:

Beginning balance

Change in fair value of real estate investments included in net loss

Ending balance

Ending balance - assets

Liabilities:

Contingent consideration:

Beginning balance

Settlements of contingent consideration liabilities

Change in fair value of contingent consideration included in net loss

Ending balance - liabilities

Total

$

$

$

$

Years ended December 31,

2018

2017

$

1,397

$

1,580
(386)

1,533

4,124

10,662

—

10,662

14,786

$

— $
—

—

— $

939

664
(86)

(120)
1,397

10,662

—

10,662

12,059

325
(113)
(212)
—

14,786

$

12,059

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, 2018:

Categories

Limited liability
investments, at fair value

Real estate investments

$

$

Fair Value
(in thousands)

Valuation Techniques

Unobservable
Inputs

Input
Value(s)

4,124

Market approach

Valuation multiples

5.0x - 8.8x

10,662 Market and income approach

Cap rates

7.5%

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, 2017:

Categories

Limited liability 
investments, at fair value

Real estate investments

$

$

Fair Value
(in thousands)

Valuation Techniques

Unobservable
Inputs

Input
Value(s)

1,397

Market approach

Valuation multiples

5.0x - 7.0x

10,662 Market and income approach

Cap rates

7.5%

All transfers are recognized by the Company at the beginning of each reporting period.  Transfers between Levels 2 and 3 generally 
relate to whether significant unobservable inputs are used for the fair value measurements.  There were no transfers between levels 
in 2018 or 2017.

113

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Investments Measured Using the Net Asset Value per Share Practical Expedient

The following table summarizes investments for which fair value is measured using the net asset value per share practical expedient 
at December 31, 2018:

December 31, 2018

Limited liability
investments, at fair value

$

Fair Value
(in thousands)

Unfunded Commitments
(in thousands)

Redemption
Frequency

Redemption
Notice Period

21,685

n/a

n/a

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, 2017:

December 31, 2017

Limited liability
investments, at fair value

$

Fair Value
(in thousands)

Unfunded Commitments
(in thousands)

Redemption
Frequency

Redemption
Notice Period

20,500

n/a

n/a

n/a

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 year ended December 31, 2018, the Company 
recorded adjustments to decrease the fair value of certain investments in private companies for observable price changes of $0.6 
million and impairments of $1.0 million, respectively, which are included in net change in unrealized loss on private company 
investments in the consolidated statements of operations.  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. 

NOTE 30 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, 2018 and December 31, 2017, 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").  During 2018 and 2017, 
the Company funded approximately $0.5 million and $0.3 million, respectively, in response to Capital Calls.  During 2018 and 
2017,  Fitzgerald  and  Fitzgerald’s  immediate  family  members  funded  their  respective  Capital  Calls.   Argo  Holdings  used  the 
proceeds of the Capital Calls to make investments, cover general operating expenses and pay the management fee owed to Argo 
Management.

(b) 

1347 Property Insurance Holdings, Inc.

In November 2012, the Company formed Maison Insurance Company ("Maison"), a Louisiana domiciled property and casualty 
insurance company.  In preparation for a transaction to take Maison public, the Company formed 1347 Property Insurance Holdings, 
Inc. (“PIH”).  Maison was a wholly owned subsidiary of PIH, which completed an initial public offering effective March 31, 2014, 

114

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

pursuant to which the Company disposed of a majority interest in PIH.  The Company owned zero and 8% of the common shares 
of PIH at December 31, 2018 and December 31, 2017, respectively.  

D. Kyle Cerminara ("Cerminara") was appointed to the PIH Board of Directors on December 27, 2016 and became Chairman of 
the Board of Directors of PIH on May 11, 2018.  Since April 2012, Cerminara has also served as the Chief Executive Officer of 
Fundamental Global Investors, LLC ("FGI").  During 2018 and 2017, FGI was a shareholder known by the Company to be a 
beneficial owner of more than 5% of the Company’s outstanding common shares.  Larry G. Swets, Jr. ("Swets") has served as a 
member of the PIH Board of Directors since November 21, 2013 and served as the Chairman of the Board of Directors of PIH 
from March 5, 2017 to May 11, 2018.  Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until 
September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018.

On February 11, 2014, the Company's subsidiary, 1347 Advisors, entered into a management services agreement with PIH which 
provides for certain services, including forecasting, analysis of capital structure and reinsurance programs, consultation in future 
restructuring or capital raising transactions, and consultation in corporate development initiatives, that 1347 Advisors will provide 
to PIH unless and until 1347 Advisors and PIH agree to terminate the services.  On February 24, 2015, the Company announced 
that it had entered into a definitive agreement with PIH to terminate the management services agreement.  Pursuant to the transaction, 
1347 Advisors received the following consideration: $2.0 million in cash; $3.0 million of 8% preferred stock of PIH, mandatorily 
redeemable on February 24, 2020; a Performance Shares Grant Agreement with PIH, whereby 1347 Advisors will be entitled to 
receive 100,000 shares of PIH common stock if at any time the last sales price of PIH's common stock equals or exceeds $10.00
per share for any 20 trading days within any 30-trading day period; and warrants to purchase 1,500,000 shares of common stock 
of PIH with a strike price of $15.00, expiring on February 24, 2022. For the year ended December 31, 2018, the Company recognized 
$0.7 million of loss on change in fair value of equity investments in its consolidated statement of operations related to the change 
in fair value of the warrants to purchase 1,500,000 shares of common stock of PIH.

On March 26, 2014, the Company entered into a Performance Share Grant Agreement with PIH, whereby the Company will be 
entitled to receive up to an aggregate of 375,000 shares of PIH common stock upon achievement of certain milestones for PIH’s 
stock price. Pursuant to the terms of the Performance Share Grant Agreement, if at any time the last sales price of PIH’s common 
stock equals or exceeds: (i) $12.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and 
the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock; 
(ii) $15.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading 
days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 125,000
shares of common stock earned pursuant to clause (i) herein); and (iii) $18.00 per share (as adjusted for stock splits, stock dividends, 
reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 
125,000 shares of PIH common stock (in addition to the 250,000 shares of common stock earned pursuant to clauses (i) and (ii) 
herein).  

On January 2, 2018, the Company entered into an agreement with PIH to cancel the $10.00 per share Performance Share Grant 
Agreement in exchange for cash consideration of $0.3 million and to sell the $3.0 million of 8% preferred stock of PIH, mandatorily 
redeemable on February 24, 2020, for $3.0 million plus accrued but unpaid dividends.  On July 24, 2018, the Company entered 
into an agreement with PIH to cancel the $12.00 per share, $15.00 per share and $18.00 per share Performance Share Grant 
Agreement in exchange for cash consideration of $1.0 million. For the year ended December 31, 2018, the Company recorded 
gains, included in gain on change in fair value of equity investments in the consolidated statements of operations, of $1.3 million
related to these transactions.  No shares were received by the Company under either of the performance share grant agreements 
as of December 31, 2018.

(c) 

Itasca Capital Ltd.

Investment in investee includes the Company's investment in the common stock of ICL, a publicly traded Canadian corporation, 
and is accounted for under the equity method.  The Company owned 22.9% and 31.2% of the common shares of ICL at December 
31, 2018 and December 31, 2017, respectively.  

Ballantyne Strong Inc. ("Ballantyne") owned 40.6% and 32.3% of the common shares of ICL at December 31, 2018 and December 
31, 2017, respectively.  Cerminara has served as the Chief Executive Officer of Ballantyne since November 2015 and as Chairman 
of the Board of Ballantyne since May 2015.  Cerminara was appointed to the ICL Board of Directors on June 13, 2016 and became 
Chairman of the Board of Directors of ICL on June 4, 2018.  Since April 2012, Cerminara has also served as the Chief Executive 
Officer of FGI.  During 2018 and 2017, FGI was a shareholder known by the Company to be a beneficial owner of more than 5% 
of the Company’s outstanding common shares.  Swets has served as the ICL Chief Executive Officer and a member of the ICL 

115

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Board of Directors since June 9, 2016.  Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until 
September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018. 
Fitzgerald has served as a member of the ICL Board of Directors since June 9, 2016.  Fitzgerald joined the Company as an Executive 
Vice President in April 2016 following the Company’s acquisition of Argo.  Fitzgerald has served as the Company’s Chief Executive 
Officer since September 5, 2018 and has served on the Company’s Board of Directors since April 21, 2016.

ICL and the Company executed a management service agreement effective June 10, 2016 pursuant to which the Company provided 
management services to ICL, including the non-exclusive use and services of appropriately qualified individuals to serve as ICL’s 
Chief Executive Officer and Chief Financial Officer, for an annual service fee of $0.0 million.  This agreement was later amended 
on November 17, 2017 to provide an annual service fee of $0.0 million, beginning with full year 2017.  The agreement was 
ultimately terminated effective January 31, 2019.

On October 30, 2019, the Company executed an agreement to sell 1,974,113 shares of ICL common stock, at a price of C$0.35 
per share, to FGI for cash proceeds totaling C$0.7 million.  On October 31, 2019, the Company executed an agreement to sell 
3,011,447 shares of ICL common stock, at a price of C$0.35 per share, to Swets for consideration totaling C$1.1 million, comprised 
of cash proceeds of C$0.2 million and 247,450 shares of the Company’s common stock.  The 247,450 shares of the Company’s 
common stock were awarded to Swets pursuant to an Amended and Restated Restricted Stock Agreement (the "Swets Restricted 
Stock Agreement") executed on September 5, 2018 related to Swets’ departure from the Company.  Pursuant to the Swets Restricted 
Stock Agreement, Swets retained 350,000 shares of restricted Company common stock that were to vest upon (i) the completion 
of the sale by 1347 Investors of its entire interest in the shares of Limbach common stock and (ii) the subsequent completion of 
the liquidation of 1347 Investors and the distribution of its assets to its members.  Pursuant to a Distribution and Redemption 
Agreement, dated as of September 30, 2019, by and among 1347 Investors and its members, the Company received distributions 
of cash proceeds of $0.6 million and 0.6 million shares of Limbach common stock, which the Company deemed as having satisfied 
the performance obligations described in the Swets Restricted Stock Agreement.  Also, pursuant to the Swets Restricted Stock 
Agreement, Swets exercised his right to authorize the Company to withhold 102,550 shares of restricted Company common stock, 
which would otherwise have been delivered or available for vesting, in order to satisfy all federal, state, local or other taxes required 
to be withheld or paid in connection with such award, leaving Swets with 247,450 shares of the Company’s common stock.

(d) 

Fundamental Global Investors, LLC

During 2018 and 2017, FGI was a shareholder known by the Company to be a beneficial owner of more than 5% of the Company’s 
outstanding common shares.

On October 25, 2017, the Company executed an agreement to sell 900,000 shares of PIH common stock, at a price of $7.85 per 
share, to FGI in two separate transactions for cash proceeds totaling $7.1 million.  On November 1, 2017, the Company sold 
475,428 of the 900,000 shares of PIH common stock to FGI for cash proceeds totaling $3.7 million.  The second transaction, for 
the sale of the remaining 424,572 shares of PIH common stock for cash proceeds totaling $3.4 million, closed on March 15, 2018 
following FGI having obtained the necessary regulatory approvals.

On July 30, 2018, the Company executed an agreement to sell its remaining 75,000 shares of PIH common stock, at a price of 
$7.13 per share, to FGI for cash proceeds totaling $0.5 million.

On July 30, 2018, the Company executed an agreement to sell 1,813,889 shares of ICL common stock, at a price of C$0.72 per 
share, to FGI for cash proceeds totaling C$1.3 million.

For the year ended December 31, 2018, the Company recorded losses, included in gain on change in fair value of equity investments 
in the consolidated statements of operations, of $0.1 million related to these transactions. For the year ended December 31, 2017, 
the Company recorded gain, included in net realized (losses) gain in the consolidated statements of operations, of $0.1 million
related to this transaction.

(e) 

Insurance Income Strategies Ltd.

IIS is a Bermuda corporation, formed in October 2017, organized to offer collateralized reinsurance in the property catastrophe 
market through its wholly owned operating subsidiary IIS Re Ltd. The Company held 100% of the outstanding common stock of 
IIS at December 31, 2018 and December 31, 2017.  The Company did not invest any capital against the common shares and has 
not invested any capital in IIS via any other security of IIS.  The Company also does not have any commitment to provide capital 
to IIS.  See Note 7, "Variable Interest Entities," for further discussion of IIS.  Swets has served as the Chairman of the Board of 

116

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Directors of IIS since its formation.  Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 
5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018.

Effective August 10, 2018, simultaneous with IIS issuing preferred stock to a third-party investor, the Company and IIS entered 
into a management service agreement, which describes the Company’s duties and rights to remuneration.  The management service 
agreement describes the Company’s duties to include (a) identification and due diligence of potential transaction counterparties 
for consideration by IIS management; (b) advice on capital structure and corporate development opportunities; (c) support for 
compliance with the rules and regulations of the SEC; and (d) other periodic and special requests deemed within the scope of the 
management service agreement.  The management service agreement provides for a fee 0.9% of the assets of IIS and 9% of the 
annual net profits.

Pursuant to other agreements executed August 10, 2018 simultaneous with IIS issuing preferred stock to a third-party investor, 
the Company (a) is obligated to share with the IIS third-party investor 50% of any future fees generated under the management 
service agreement and (b) waives its right to receive any fees until such time that the IIS third-party investor is either redeemed 
or exchanged into publicly traded equity shares of IIS, in either case for consideration not less than the IIS third-party investor’s 
original $15.0 million investment.  As of December 31, 2018, neither of these scenarios had occurred, so the Company is not 
entitled to any fees under the management service agreement and has not recorded any such fees.

(f) 

Limited liability investments

The Company’s investments include investments in limited liability companies in which an officer of the Company is named as 
a Manager or is authorized to act on behalf of the Manager under the respective operating agreement.

Itasca Golf Investors, LLC:

Itasca Golf Investors, LLC ("IGI") was formed on April 8, 2014 for the general purpose of real estate investment.  The members 
entered into an operating agreement under which the Company acquired a 42.9% membership interest in IGI.  1347 Capital LLC, 
a wholly owned subsidiary of the Company, was named the Manager of IGI in the operating agreement.  Swets was authorized to 
act on behalf of the Manager.  Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 
2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018.  On September 5, 
2018, the Company sold its investment in IGI to IGI Partners LLC for $1.5 million.  Swets is a member of IGI Partners LLC. For 
the year ended December 31, 2018, the Company recorded loss, included in net realized (losses) gain in the consolidated statements 
of operations, of $0.4 million related to this transaction.

AK Realty I LLC:

AK Realty I LLC ("AKR") was formed on September 21, 2015 for the purpose of becoming a member of AKA Opportunity 
Investments I LLC, a limited liability company formed for the purpose of investing, directly or indirectly, in real estate projects.  
The members of AKR entered into an operating agreement under which the Company acquired a 33.3% membership interest in 
AKR.  Management of AKR is vested in a two-member Executive Committee.  The Company designates one of the two members 
of  the  Executive  Committee.    Decisions  of  the  Executive  Committee  require  the  unanimous  approval  of  the  members  of  the 
Executive Committee.  The Company designated Swets as its representative on the Executive Committee.  Swets also served as 
the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors 
from September 16, 2013 through December 21, 2018.

Logistics Leasing, LLC:

Logistics Leasing ("Logistics") was formed on July 26, 2017 for the purpose of acquiring and leasing small vehicles.  The members 
of Logistics entered into an operating agreement under which the Company acquired a 50% membership interest in Logistics.  The 
Company designates one of the two managers of Logistics.  Major Decisions, as defined in the operating agreement, require the 
approval of members holding at least 51% of the membership interest.  The Company designated Swets as a manager.  Swets also 
served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board 
of Directors from September 16, 2013 through December 21, 2018.

1347 Energy Holdings LLC:

1347 Energy Holdings LLC ("Energy") was formed on April 20, 2016 for the purpose of making investments in hydrocarbon assets 
as described in the operating agreement.  At December 31, 2018 and December 31, 2017, the Company owned 45.6% of the 
membership interests.  The Company also held collateralized notes in principal amount of  $0.6 million and $1.8 million and a 

117

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

surety deposit of zero and $0.7 million at December 31, 2018 and December 31, 2017, respectively. Fitzgerald owned 0.8% of the 
membership interests at December 31, 2018 and December 31, 2017.  Energy was managed through a Board of Managers comprised 
of five managers, two of whom, Swets and Fitzgerald, were appointed by 1347 Capital LLC, a wholly owned subsidiary of the 
Company.  With respect to any matter before the Board of Managers, the act of a majority of the managers constituting a quorum 
constituted the act of the Board.  Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 
5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018.  Fitzgerald joined 
the Company as an Executive Vice President in April 2016 following the Company’s acquisition of Argo.  Fitzgerald has served 
as the Company’s Chief Executive Officer since September 5, 2018 and has served on the Company’s Board of Directors since 
April 21, 2016.  During 2018, Energy entered into a purchase and sale agreement dated, February 12, 2018, for the sale of Energy 
to an unrelated third party, pursuant to which the Company’s $1.8 million collateralized loan to Energy and $0.7 million surety 
deposit were repaid in full and the Company’s equity investment, previously written down to zero under the equity method of 
accounting, was purchased.  The transaction closed in a series of installments during the fourth quarter of 2018 and the first quarter 
of  2019.    For  the  year  ended  December 31,  2018,  the  Company  recorded  gain,  included  in  net  realized  (losses)  gain  in  the 
consolidated statements of operations, of $0.0 million related to this transaction.

1347 Investors LLC:

1347 Investors was formed on April 15, 2014 for the purpose of investing in and holding securities of 1347 Capital Corp., which 
subsequently merged with Limbach Holdings, Inc., a publicly traded company.  The Company owned 26.7% of the membership 
units at December 31, 2018 and December 31, 2017.  The Company's investment in 1347 Investors is accounted for at fair value 
and reported as limited liability investments, at fair value in the consolidated balance sheets, with any changes in fair value to be 
reported in (loss) gain on change in fair value of limited liability investment, at fair value in the consolidated statements of operations.  
The fair value of this investment is calculated based on a model that distributes the net equity of 1347 Investors to all classes of 
membership interests.  The model uses quoted market prices and significant market observable inputs.  The most significant input 
to the model is the observed stock price of Limbach common stock.  

ICL owned 47.6% of the membership units at December 31, 2018 and December 31, 2017.  Ballantyne owned 40.6% and 32.3%
of the common shares of ICL at December 31, 2018 and December 31, 2017, respectively.  

Swets and Cerminara are the named managers of 1347 Investors.  All acts of the managers must be unanimous.  Cerminara has 
served as the Chief Executive Officer of Ballantyne since November 2015 and as Chairman of the Board of Ballantyne since May 
2015.  Cerminara was appointed to the ICL Board of Directors on June 13, 2016 and became Chairman of the Board of Directors 
of ICL on June 4, 2018.  Since April 2012, Cerminara has also served as the Chief Executive Officer of FGI.  During 2017 and 
2018, FGI was a shareholder known by the Company to be a beneficial owner of more than 5% of the Company’s outstanding 
common shares.  Swets has served as the ICL Chief Executive Officer and a member of the ICL Board of Directors since June 9, 
2016.  Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the 
Company’s Board of Directors from September 16, 2013 through December 21, 2018.  Fitzgerald has served as a member of the 
ICL Board of Directors since June 9, 2016.  Fitzgerald joined the Company as an Executive Vice President in April 2016 following 
the Company’s acquisition of Argo.  Fitzgerald has served as the Company’s Chief Executive Officer since September 5, 2018 
and has served on the Company’s Board of Directors since April 21, 2016.

Pursuant to a Distribution and Redemption Agreement, dated as of September 30, 2019, by and among 1347 Investors and its 
members, the Company received distributions on November 19, 2019 of cash proceeds of $0.6 million, 594,750 shares of Limbach 
common stock and 400,000 warrants, exercisable at $15 and expiring July 20, 2023, on Limbach common shares.  As a result of 
this distribution, the Company no longer owns membership units in 1347 Investors.

(g) 

Atlas Financial Holdings, Inc.

In November 2010, the Company issued promissory notes (the "Notes") to five employees (each a "Debtor" and collectively the 
"Debtors") for a total of $1.1 million, each Note bearing an interest rate of 3% (not compounding).  The Debtors used the proceeds 
to purchase shares of common stock in Atlas Financial Holdings, Inc. ("Atlas").  Atlas was created via a triangular merger and 
spun-off from the Company in December 2010, at which time the Debtors became employees of Atlas and were no longer employees 
of the Company.  The Notes required annual payments of interest on the anniversary date of the Notes, with the principal and any 
unpaid interest due in full on or before January 1, 2017, in the case of one of the Debtors, and November 1, 2017, in the case of 
the other four Debtors.  Each Debtor was required to pledge to the Company the shares purchased utilizing the Notes proceeds, 
and such pledge was to be released once the note was paid in full.  The current market value of the pledged shares is $0.1 million.

118

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

The Notes have been amended three times since their issuance, generally to extend payments of principal while also requiring 
progress payments that were not part of the original Notes.  No principal has been waived, and interest continues to accrue on 
unpaid principal. The remaining principal amount outstanding on the Notes was $0.7 million as of December 31, 2018.  The 
Company has concluded there are no indications the Debtors were experiencing financial difficulties at the time of the amendments, 
and the Company expects to collect all amounts due.  The Debtors are current with the amended terms of the Notes.  As a result, 
the Company has concluded the Notes are not impaired.

(h) 

Other related party transactions

On July 16, 2018, the Company entered into a definitive agreement to sell Mendota to Premier Holdings LLC.  Steve Harrison, 
President of Mendota, is a minority investor in Premier Holdings LLC.

On September 5, 2018, the Company entered into a Senior Advisor Agreement with Swets, its former Chief Executive Officer.  
The Senior Advisor Agreement was for a one-year term with an annual consulting fee of $0.3 million. After September 5, 2019, 
Swets will continue to provide certain consulting services for an hourly fee on an as-needed basis.

NOTE 31 COMMITMENTS AND CONTINGENT LIABILITIES

(a)         Legal proceedings:

In April 2018, TRT LeaseCo, LLC ("TRT LeaseCo"), an indirect subsidiary of Kingsway, was named as a defendant in a lawsuit 
filed in the United States District Court for the Southern District of New York relating to CMC and its subsidiaries.  Kingsway 
indirectly owns 81% of CMC.  TRT LeaseCo (an indirect wholly owned subsidiary of CMC) entered into a Management Services 
Agreement (the "MSA") with DGI-BNSF Corp. ("DGI") (an affiliate of the entity that owns the remaining 19% of CMC) in July 
2016 pursuant to which, among other things, DGI agreed to provide services to TRT LeaseCo in exchange for the fees specified 
in the MSA.  The complaint filed by DGI alleges that DGI is owed certain fees under the MSA that have not been paid.  If the case 
is decided against TRT LeaseCo, CMC and its subsidiaries (including TRT LeaseCo) would be unable to fulfill certain payment 
obligations to Kingsway under the transaction documents such that Kingsway may no longer be able to realize a material portion 
of the economic benefits originally anticipated to result from the CMC transaction, which could have a material adverse effect on 
Kingsway’s financial position, results of operations and cash flows.  Kingsway disagrees with DGI’s allegations and is vigorously 
defending these claims; however, there can be no assurance that Kingsway will ultimately prevail.  The Company’s potential 
exposure under these agreements is not reasonably determinable, and no liability has been recorded in the audited consolidated 
financial statements at December 31, 2018.  No assurances can be given, however, that the Company will not be required to perform 
under these agreements in a manner that would have a material adverse effect on the Company’s financial position, results of 
operations and cash flow.

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 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.  
The Company’s potential exposure under these agreements was not reasonably determinable at December 31, 2018, and no liability 
has been recorded in the audited consolidated financial statements at December 31, 2018.  

(b)         Guarantee:

As further discussed in Note 6, "Disposal, Discontinued Operations and Liquidation," as part of the transaction to sell Mendota, 
the Company will indemnify the buyer for loss and loss adjustment expenses with respect to open claims and certain specified 
claims in excess of Mendota's carried unpaid loss and loss adjustment expenses at June 30, 2018 related to the open claims and 
specified claims.  The Company's potential exposure under these agreements was not reasonably determinable at December 31, 
2018, and no liability has been recorded in the consolidated financial statements at December 31, 2018.

119

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

(c) 

Commitments:

The Company has entered into subscription agreements to commit up to $2.6 million of capital to allow for participation in limited 
liability investments.  At December 31, 2018, the unfunded commitment was $0.6 million.

(d)         Collateral pledged and restricted cash:

Short-term investments with an estimated fair value of $0.2 million and $0.2 million at December 31, 2018 and December 31, 
2017, respectively, were on deposit with state and provincial regulatory authorities.  The Company also has restricted cash of $17.0 
million and $15.0 million at December 31, 2018 and December 31, 2017, respectively.  Included in restricted cash are (i) $5.0 
million and zero at December 31, 2018 and December 31, 2017, respectively, held in escrow as part of the transaction to sell 
Mendota; (ii) $10.0 million and $12.2 million at December 31, 2018 and December 31, 2017, respectively, held as deposits by 
IWS and PWSC; (iii) $1.9 million and $1.9 million at December 31, 2018 and December 31, 2017, respectively, on deposit with 
state and provincial regulatory authorities; and (iv) $0.1 million and $0.9 million at December 31, 2018 and December 31, 2017, 
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 32 REGULATORY CAPITAL REQUIREMENTS AND RATIOS

In  the  United  States,  a  risk-based  capital  ("RBC")  formula  is  used  by  the  National Association  of  Insurance  Commissioners 
("NAIC") to identify property and casualty insurance companies that may not be adequately capitalized.  In general, insurers 
reporting surplus as regards policyholders below 200% of the authorized control level, as defined by the NAIC, at December 31 
are subject to varying levels of regulatory action, including discontinuation of operations.  As of December 31, 2018, surplus as 
regards policyholders reported by Amigo exceeded the 200% threshold.

During the fourth quarter of 2012, the Company began taking steps to place all of Amigo into voluntary run-off.  As of December 
31, 2012, Amigo’s  RBC was 157%.  In April 2013, Kingsway  filed a comprehensive run-off  plan with the Florida Office of 
Insurance Regulation, which outlines plans for Amigo's run-off.  Amigo remains in compliance with that plan.  As of December 31, 
2018, Amigo's RBC was 1,905%.

Kingsway Re, which is domiciled in Barbados, is required by the regulator in Barbados to maintain minimum capital levels.  As 
of December 31, 2018, the capital maintained by Kingsway Re was in excess of the regulatory capital requirements in Barbados.

NOTE 33 STATUTORY INFORMATION AND POLICIES

The Company's insurance subsidiary, Amigo, prepares statutory basis financial statements in accordance with accounting practices 
prescribed or permitted by the Florida Office of Insurance Regulation. "Prescribed" statutory accounting practices include state 
laws, regulations and general administrative rules, as well as a variety of publications of the NAIC. "Permitted" statutory accounting 
practices encompass all accounting practices that are not prescribed.  Such practices may differ from state to state; may differ from 
company to company within a state; and may change in the future.  

Amigo is required to report results of operations and financial position to insurance regulatory authorities based upon statutory 
accounting practices.  In converting from statutory to U.S. GAAP, typical adjustments include the inclusion of statutory non-
admitted  assets  in  the  balance  sheets,  the  inclusion  of  net  unrealized  holding  gains  or  losses  related  to  fixed  maturities  in 
shareholders’ equity, and the inclusion of changes in deferred tax assets and liabilities in net (loss) income.

Statutory capital and surplus and statutory net loss for Amigo are:

(in thousands)

Net loss, statutory basis

Capital and surplus, statutory basis

2018
(1,506)
2,662

$

$

December 31,

2017
(1,357)
4,168

$

$

120

KINGSWAY FINANCIAL SERVICES INC.
Notes to Consolidated Financial Statements

Amigo is required to hold minimum levels of statutory capital and surplus to satisfy regulatory requirements. The minimum 
statutory capital and surplus, or company action level RBC, necessary to satisfy regulatory requirements for Amigo was $0.3 
million at December 31, 2018. Company action level RBC is the level at which an insurance company is required to file a corrective 
action plan with its regulators and is equal to 200% of the authorized control level RBC.

Dividends paid by Amigo are restricted by regulatory requirements of the Florida Office of Insurance Regulation.  The maximum 
amount of dividends that can be paid to shareholders by insurance companies domiciled in the state of Florida without prior 
regulatory approval is generally limited to the greater of (i) 10% of a company's statutory capital and surplus at the end of the 
previous year or (ii) 100% of the company's net income for the previous year and is generally required to be paid out of an insurance 
company's unassigned funds.

At December 31, 2018, Amigo was restricted from making any dividend payments to the holding company without regulatory 
approval.  

NOTE 34 SUBSEQUENT EVENT

On March 1, 2019, the Company acquired 100% of the outstanding shares of Geminus Holding Company, Inc. ("Geminus") for 
approximately $8.4 million.  Geminus is a specialty, full-service provider of vehicle service contracts ("VSCs") and other finance 
and insurance ("F&I") products to used car buyers around the country.  Geminus, headquartered in Wilkes-Barre, Pennsylvania, 
has been creating, marketing and administering VSCs and F&I products on high-mileage used cars through its subsidiaries, The 
Penn Warranty Corporation ("Penn") and Prime Auto Care, Inc. ("Prime"), since 1988.  Penn and Prime distribute these products 
via independent used car dealerships and franchised car dealerships, respectively.  Geminus' balance sheet and results of operations 
will be included in the consolidated financial statements of the Company, beginning with the first quarter of 2019.

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, 2018.  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, 2018, the Company's disclosure controls and procedures were not effective as a result of material weaknesses in 
the  Company's  internal  control  over  financial  reporting  related  to  the  accounting  for  and  disclosure  of  certain  complex  and 
nonrecurring  transactions;  the  accounting  for  and  disclosure  of  certain  other  items;  monitoring  the  collectability  of  accounts 
receivable balances; other-than-temporary impairment on equity method investments; and certain account reconciliations.

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 

121

KINGSWAY FINANCIAL SERVICES INC.

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, 2018, our internal controls over financial reporting were not effective because 
of the existence of material weaknesses in internal control over financial reporting related to the accounting for and disclosure of 
certain complex and nonrecurring transactions; the accounting for and disclosure of certain other items; monitoring the collectability 
of  accounts  receivable  balances;  other-than-temporary  impairment  on  equity  method  investments;  and  certain  account 
reconciliations.

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 accounting for and 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 reclassification of investment income, related to equity method investments, from loss from discontinued operations, 
net of taxes to net investment income in the consolidated statement of operations;
the identification, accounting and disclosure of investments demonstrating characteristics of variable interest entities, 
including the consolidation of certain investments;
the adoption and application of ASU 2014-09;
identification, disclosure and accounting for equity-classified warrants; and
purchase accounting, as it relates to the identification and valuation of intangible assets and goodwill.

Concerning the accounting for and disclosure of certain other items, the execution of the controls over the application of accounting 
literature did not operate effectively with respect to separating restricted cash from cash and cash equivalents on the face of the 
consolidated balance sheet.  Additionally, the Company did not have adequate controls in place pertaining to disclosure of related 
parties.

Regarding the collectability of accounts receivable balances, the Company did not have adequate controls and procedures with 
respect to evaluating balances for collectability, including the lack of a formal policy governing the review of accounts, as well 
as calculating and documenting necessary reserves.  

With respect to other-than-temporary impairment on equity method investments, the Company did not properly apply the accounting 
literature when performing its analysis in determining whether its investment in investee was other-than-temporarily impaired as 
of December 31, 2018.

Finally,  with  respect  to  the  lack  of  adequate  procedures  regarding  certain  account  reconciliations,  there  were  errors  in  the 
reconciliation of account balances as they were not performed timely and/or at a level of precision to identify errors and incorrect 
balance sheet and income statement classification for certain cash, receivable, deposit, accounts payable, deferred revenue, escheat 
liability and investment income accounts.

The matters were discovered during the course of the 2018 external audit of the accounts and were reviewed with the Company's 
Audit Committee.  As explained in Note 3 to the consolidated financial statements, certain of these material weaknesses resulted 
in the restatement of our consolidated financial statements for the year ended December 31, 2017 and our unaudited consolidated 
financial statements for each of the quarters ended March 31, 2018, June 30, 2018 and September 30, 2018.  The misstatements 
in the consolidated financial statements were corrected prior to the issuance of the Company's consolidated financial statements 
as of and for the year ended December 31, 2018.

As a result of the identified material weaknesses, 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 weaknesses 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 
2018 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.

122

KINGSWAY FINANCIAL SERVICES INC.

Remediation Process

The Company is evaluating the material weaknesses and developing a plan of remediation to strengthen the effectiveness of the 
design and operation of its internal control environment.  The remediation plan will include the following actions:

• 

Perform a comprehensive assessment of all existing accounting policies and revise existing policies and/or introduce new 
policies, as needed;

•  Enhance the formality of its review procedures with respect to its accounting for any new investments, as well as the 

• 

• 

periodic evaluation of existing investments;
Implement additional review procedures with respect to its accounting under ASU 2014-09 to ensure the Company’s 
accounting will continue to be in accordance with that standard on a go-forward basis;
Implement  additional  identification,  accounting  and  review  controls  with  respect  to  complex  and  nonrecurring 
transactions, as well as augment existing staff with outside skilled accounting resources, as appropriate, and strengthen 
the review process to improve the operation of financial reporting and corresponding internal controls; 

•  Enhance the formality and rigor with respect to identifying and tracking all material related party transactions, as well 

updating its disclosures controls to enhance the focus on related party disclosure requirements; and

•  Enhance the formality and rigor of review with respect to the collectability of accounts receivable balances, other-than-

temporary impairment reviews on equity method investments and the account reconciliation procedures.

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.  The Company has started to implement these steps; however, some of these 
steps will take time to be fully integrated and confirmed to be effective and sustainable.  Additional controls may also be required 
over time.  Until the remediation steps set forth above are fully implemented and tested, the material weakness described above 
will continue to exist.

Changes in Internal Control over Financial Reporting

There have been no changes in the Company's internal control over financial reporting during the period beginning October 1, 
2018, and ending December 31, 2018, that have materially affected, or are reasonably likely to materially affect, its internal control 
over financial reporting.

123

 
KINGSWAY FINANCIAL SERVICES INC.

Item 9B. Other Information

None

PART III. 

Item 10. Directors, Executive Officers, and Corporate Governance

Board of Directors(1)

John T. 
Fitzgerald

Age: 48

Residence:  
Illinois, 
United States 
of America

Director 
Since: April 
21, 2016

Not 
independent

Gregory P. 
Hannon

Age: 65

Residence: 
Ontario, Canada

Director Since: 
September 16, 
2009

Independent(2)

John T. Fitzgerald has served as Chief Executive Officer of Kingsway since September 2018. Mr. Fitzgerald 
joined  Kingsway  as  Executive Vice  President  on April  21,  2016  following  Kingsway’s  acquisition  of Argo 
Management Group, a private equity investment partnership co-founded by Mr. Fitzgerald in 2002. Effective 
March 8, 2017, Mr. Fitzgerald was appointed President and Chief Operating Officer of Kingsway. Prior to co-
founding Argo  Management  Group,  Mr.  Fitzgerald  was  managing  director  of Adirondack  Capital,  LLC,  a 
financial futures and derivatives trading firm, and he was a seat-owner on the Chicago Board of Trade. Mr. 
Fitzgerald was previously the CEO of Hunter MFG, LLP and, from 2006 to 2016, Mr. Fitzgerald served as its 
Chairman. Mr. Fitzgerald received a Bachelor of Science degree from DePaul University and is an MBA graduate 
of the Kellogg School of Management, Northwestern University. Mr. Fitzgerald’s education, background and 
experience qualify him for his role with Kingsway.
Board Committee
Membership:
Board

Director, Atlas Financial Holdings, Inc. since May 2013

Public Board Membership:

Director, Itasca Capital, Ltd., since June 2016

Gregory P. Hannon has been a Vice-President and Director of Oakmont Capital Inc., a Toronto-based private 
investment company, since 1997.  He previously was a founding partner of Lonrisk, a Toronto-based specialty 
insurer and subsidiary of the London Insurance Group, where he was the Chief Financial Officer.  Prior to that, 
Mr. Hannon worked for the Continental Bank of Canada in commercial credit and as auditor for Arthur Andersen 
and Company, Chartered Accountants.  Mr. Hannon received a Bachelor of Commerce degree from Queen’s 
University in 1978 and an M.B.A. from The Harvard Business School in 1987.  Mr. Hannon brings to the Board 
entrepreneurial experience, as well as expertise in accounting, auditing and financial reporting.
Board Committee
Membership:
Board

Public Board Membership:

None

Audit Committee

Nominating  and  Corporate 
Governance Committee

124

KINGSWAY FINANCIAL SERVICES INC.

Terence M. 
Kavanagh

Age: 65

Residence: 
Ontario, Canada

Director Since: 
April 23, 2009

Independent(2)

Terence M. Kavanagh has, since 1997, served as President and a Director of Oakmont Capital Inc., a Toronto-
based  private  investment  company.    Prior  to  co-founding  Oakmont  Capital,  Mr.  Kavanagh’s  previous 
experience includes managing the Brentwood Pooled Investment Fund, a North American based investment 
fund, and managing a number of family-owned operating businesses in the real estate, property management 
and building services industries.  Mr. Kavanagh was previously an investment banker in New York and Toronto 
with The First Boston Corporation and Lehman Brothers.  Mr. Kavanagh received a Bachelor of Law degree 
from Western University in 1978, and an M.B.A. from the Tuck School of Business at Dartmouth College in 
1982. Mr. Kavanagh brings extensive knowledge of the financial services industry to the Board.
Board Committee Membership:

Public Board Membership:

Board

None

Compensation & Management Resources
Committee

Audit Committee

Investment Committee (prior to May 30,
2018)

Plan Committee

Doug Levine

Age: 61

Doug Levine has been the President of Levine Management, a real estate developer, since January 2013.  He 
graduated in 1980 from Tufts University with a Bachelor’s Degree in Economics.
Board Committee Membership:

Public Board Membership:

Residence:  
Florida, United 
States of 
America

Director Since: 
May 30, 2018

Joseph D. 
Stilwell 

Age: 58

Residence:  
New York, 
United States of 
America

Director Since: 
April 23, 2009

Independent(2)

Notes: 

Board (since May 30, 2018)

None

Audit Committee (since May 30, 2018)

Investment Committee (since May 30, 2018)

Joseph D. Stilwell is the owner and managing member of Stilwell Value LLC, the General Partner of a group 
of funds known as The Stilwell Group.  Mr. Stilwell started his first fund in 1993 and has been reviewing and 
analyzing financial statements and managing investment funds for well over 20 years.  He graduated in 1983 
from the Wharton School at the University of Pennsylvania with a Bachelor of Science in Economics.
Board Committee Membership:

Public Board Membership:

Board

None

Audit Committee (prior to May 30, 2018)

Investment Committee (since May 30, 2018)

Nominating and Corporate Governance
Committee (since May 30, 2018)
Compensation & Management Resources
Committee

Plan Committee

(1)  All of the directors attended the 2018 annual meeting of shareholders.
(2) 

“Independent”  refers  to  the  standards  of  independence  established  under  section  301  of  the  Sarbanes-Oxley Act  of  2002  (“SOX”)  and  the  criteria  for 
independence established by the NYSE and SEC.

125

KINGSWAY FINANCIAL SERVICES INC.

Executive Officers Who Are Not Directors

Name (Age)

Executive Officer Since Current Position

Previous Business Experience

William A. Hickey, Jr. (61) August 30, 2010

EVP and CFO

Paul R. Hogan (35)

May 2019

Secretary  and  General 
Counsel

Mr.  Hickey  has  served  as  Executive  Vice 
President of the Company since August 2010, as 
CFO since April 2011, and as Chief Operating 
Officer  from  August  2010  to  March  2017.  
Before joining the Corporation, Mr. Hickey was 
a  Managing  Director  at  the  Chicago  office  of 
Macquarie  Capital,  a  corporate  finance  and 
investment firm, from 2009 to 2010.  Mr. Hickey 
earned his Bachelor of Business Administration 
degree  in  accountancy  from  the  University  of 
Notre  Dame 
in  1981  and  a  Master  of 
Management degree in finance and management 
policy  from 
the  J.L.  Kellogg  School  of 
Management  at  Northwestern  University  in 
1986.  He was awarded the Chartered Financial 
Analyst  designation  in  1989  and  the  Certified 
Public Accountant designation in 1981.

Mr.  Hogan  joined  the  Company  as  General 
Counsel  on  May  1,  2019  and  was  elected 
Secretary later that month. Prior to joining the 
Corporation, Mr. Hogan was a Senior Corporate 
Attorney  for  KapStone  Paper  and  Packaging 
Corporation. Mr. Hogan joined KapStone after 
working in private legal practice, most recently 
with Greenberg Traurig LLP. Mr. Hogan holds 
an  undergraduate  degree 
Indiana 
University,  with  majors 
in  mathematics, 
economics  and  political  science,  and  a  Juris 
Doctorate from the Indiana University Maurer 
School of Law - Bloomington. 

from 

Involvement in Certain Legal Proceedings

Mr. Hannon was a director of Delhi Solac Inc., which was placed into bankruptcy on June 6, 2014.

Mr. Fitzgerald was a director of Hunter Licensed Sports Distributing Corporation, which was the subject of a receivership order 
from the Superior Court of Quebec dated March 3, 2017. The receivership ended on September 27, 2017 following a Court order. 
Hunter was subsequently placed into bankruptcy on August 20, 2018.

In March of 2015, Mr. Stilwell and his affiliate, Stilwell Value LLC, an SEC-registered investment adviser (“Value”), consented 
to the entry of an administrative SEC order (the “Order”) that alleged civil violations of certain securities regulations for, among 
other things, failing to adequately disclose conflicts of interest presented by inter-fund loans between certain private investment 
partnerships managed by Value or Mr. Stilwell, which loans were repaid in full without monetary loss to investors from the alleged 
conduct. Under the Order, among other things, (1) Mr. Stilwell was suspended from March 2015 to March 2016 from association 
with Value or any other SEC-regulated investment business and paid a civil money penalty of $100,000, and (2) Value paid a civil 
money penalty of $250,000 and repaid certain management fees. All obligations under the Order have been satisfied.

The Audit Committee

The Board has a standing Audit Committee which operates pursuant to a written charter adopted by the Board. The Audit Committee 
consists  of  three  or  more  directors,  each  of  whom  is  an  outside  director  who  is  unrelated  to  the  Corporation,  free  from  any 
relationship that would interfere with the exercise of his or her independent judgment and each of whom is "independent" under 
the listing rules of the NYSE. Audit Committee members meet the requirements of all applicable securities laws and the NYSE. 
All members of the Audit Committee are financially literate, being defined as able to read and understand basic financial statements, 
and the Chair of the Audit Committee has accounting or related financial management expertise. At least one member of the Audit 
Committee is an "audit committee financial expert" as defined in the rules and regulations of the SEC. Pursuant to the Audit 

126

KINGSWAY FINANCIAL SERVICES INC.

Committee Charter, members of the Audit Committee may not simultaneously serve on the audit committees of more than two 
other public companies without the approval of the Audit Committee.

The primary purpose of the Audit Committee is to:

(i) 

Identify and monitor the management of the principal risks that could impact the financial reporting of the Corporation;

(ii) 
reporting and accounting appropriateness and compliance;

Monitor the integrity of the Corporation’s financial reporting process and system of internal controls regarding financial 

(iii) 

Appoint, replace and monitor the independence and performance of the Corporation’s external auditors;

(iv) 

Provide an avenue of communication among the external auditors, management and the Board; and

(v) 

Review the annual audited and quarterly unaudited financial statements with management and the external auditors.

As of February 27, 2020, the Audit Committee was comprised of Gregory P. Hannon (Chair), Terence M. Kavanagh and Doug 
Levine. The Board has determined that each member of the Audit Committee is "independent" and meets the financial literacy 
requirements of the NYSE listing standards, and that each member of the Audit Committee meets the enhanced independence 
standards established by the SEC (including Section 10A(m)(3) of and Rule 10A-3 under the Exchange Act). The following is a 
description of the education and experience of each member of the Audit Committee that is relevant to the performance of his 
responsibilities as a member of the Audit Committee:

Gregory P. Hannon has been a Vice-President and Director of Oakmont Capital Inc. since 1997. He previously was a founding 
partner of Lonrisk, a Toronto-based specialty insurer and subsidiary of the London Insurance Group, where he was the Chief 
Financial Officer. Prior to that, Mr. Hannon worked for the Continental Bank of Canada in commercial credit and as an auditor 
for Arthur Andersen and Company, Chartered Accountants. Mr. Hannon received a Bachelor of Commerce degree from Queen’s 
University in 1978 and a Master of Business Administration from The Harvard Business School in 1987. The Board has determined 
that Mr. Hannon qualifies as an "audit committee financial expert" as that term is defined in the rules and regulations established 
by the SEC.

Terence M. Kavanagh has served as President and a Director of Oakmont Capital Inc. since 1997. Prior to his cofounding of 
Oakmont Capital Inc., he managed the Brentwood Pooled Investment Fund and worked as an investment banker in New York and 
Toronto. Mr. Kavanagh earned a Bachelor of Law degree from Western University and a Master of Business Administration from 
the Tuck School of Business at Dartmouth College.

Doug Levine has been the President of Levine Management, a real estate developer, since January 2013. He graduated in 1980 
from Tufts University with a Bachelor’s Degree in Economics.

The Audit Committee held fourteen (14) meetings in the fiscal year ended December 31, 2018. The responsibilities and duties of 
the Audit Committee are set out in the Audit Committee’s charter, which was amended and adopted by the Board on May 23, 2019 
and is available on the Corporation’s website at www.kingsway-financial.com.

Report of the Audit Committee

The Audit Committee has met and held discussions with management and the independent auditors. Management represented to 
the Audit  Committee  that  the  Corporation’s  consolidated  financial  statements  were  prepared  in  accordance  with  accounting 
principles generally accepted in the United States of America, and the Audit Committee has reviewed and discussed the audited 
consolidated  financial  statements  with  management  and  the  independent  auditors.  The Audit  Committee  discussed  with  the 
independent auditors the matters required to be discussed by the applicable requirements of the Public Company Accounting 
Oversight Board ("PCAOB") and the SEC.

The  Corporation’s  independent  auditors  also  provided  to  the Audit  Committee  the  written  disclosures  required  by  applicable 
requirements  of  the  PCAOB  regarding  the  independent  auditors’  communications  with  the  Audit  Committee  concerning 
independence, and the Audit Committee discussed with the independent auditors that firm’s independence. The Audit Committee 
also considered whether the provision of non-audit services by the independent auditors is compatible with their independence.

127

KINGSWAY FINANCIAL SERVICES INC.

Based  upon  the Audit  Committee’s  discussion  with  management  and  the  Corporation’s  independent  auditors  and  the Audit 
Committee’s review of the representation of management and the report of the independent auditors to the Audit Committee, the 
Audit Committee recommended that the Board include the audited consolidated financial statements in the Corporation’s Annual 
Report on Form 10-K for the fiscal year ended December 31, 2018 filed with the SEC.

Members of the Audit Committee

Gregory P. Hannon (Chair)

Terence M. Kavanagh

Doug Levine

Code of Ethics

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

Named Executive Officers for 2018

The following individuals are the named executive officers for 2018.  Each of the following individuals, except for Mr. Swets, 
held the position(s) set forth opposite his name as of December 31, 2018.  Mr. Swets held the position of Chief Executive Officer 
until his resignation on September 5, 2018.

Name

Title

John T. Fitzgerald

William A. Hickey, Jr.

Larry G. Swets, Jr.

Hassan R. Baqar

Notes:  

President & Chief Executive Officer(1)

Executive Vice President & Chief Financial Officer

Former Chief Executive Officer(2)
Vice President(3)

(1)  Mr. Fitzgerald has served as Chief Executive Officer of the Company since September 2018. 
(2)  Mr. Swets served as Chief Executive Officer of the Company from July 2010 until September 2018.
(3)  Mr. Baqar served as Vice President of the Company from January 2014 until his resignation in January 2019. 

128

KINGSWAY FINANCIAL SERVICES INC.

2018 Summary Compensation Table 

The following table provides information regarding the compensation of our named executive officers for the last three completed 
fiscal years. 

Name and Principal
Position

Year

Salary  ($)

Bonus  
($)

Stock Awards
($)

Option
Awards  ($)

All Other 
Compensation(1)
($)

Total
($)

John T. Fitzgerald,
President & Chief
Executive Officer

William A. Hickey, Jr.,
Executive Vice President 
& Chief Financial Officer

Larry G. Swets, Jr.,
Former Chief Executive
Officer

Hassan R. Baqar, Vice
President

2018

2017

2016

2018

2017

2016

2018

2017

2016

2018

2017

2016

432,564

350,000

209,231

360,000

360,000

360,000

364,101

500,000

500,000

240,000

205,000

170,000

250,000 (2)

—
185,000 (3)
50,000 (2)

—

30,000 (2)

—

—

340,000 (3)

—

—

200,000 (3)

—

—
2,865,000 (4)

—

—
71,764 (5)

—

—

—

—

—

—

—

—

—

—

—

—

—

—

—

—

—

—

28,876

20,235

1,772

25,907

25,782

26,340

28,513

39,359

32,296

12,240

12,177

16,783

461,440

370,235

3,332,767

385,907

385,782

416,340

392,614

539,359

872,296

252,240

217,177

386,783

Notes: 

(1) 

(2) 
(3) 
(4) 

(5) 

For each named executive officer, amounts reported in this column include employer-paid life insurance premiums and contributions to the Company’s 
401(k) retirement plan and Employee Stock Purchase Plan. The Company also paid for executive wellness physicals for certain of our named executive 
officers.

This amount represents a discretionary cash bonus paid to Messrs. Fitzgerald and Hickey in 2019 for work performed in 2018.

This amount represents a discretionary cash bonus paid to Messrs. Swets, Hickey and Baqar in 2017 for work performed in 2016.

Amount reflects the aggregate grant date fair value of Restricted Stock Units. The amount was determined by multiplying the grant date fair value of 
the award by the number of Restricted Stock Units granted. This amount represents Restricted Stock Units awarded August 24, 2016, which become 
fully vested on March 28, 2024 if Mr. Fitzgerald remains in continuous employment with the Company through such date. The actual value that Mr. 
Fitzgerald may receive depends on market prices, and there can be no assurance that the amounts reflected will actually be realized.

Amount represents the aggregate grant date fair value of options. The amount does not represent the realized or unrealized earnings or value earned in 
the year. The actual value that the named executive officer may receive depends on market prices, and there can be no assurance that the amounts 
reflected will actually be realized.

129

KINGSWAY FINANCIAL SERVICES INC.

2018 Outstanding Equity Awards at Fiscal Year-End

Option Awards

Stock Awards

Number of
Securities
Underlying
Unexercised
Options
Exercisable (#)
40,000 (2)

—

—

—

Number of
Securities
Underlying
Unexercised
Options
Unexercisable
(#)

n/a

n/a

n/a

n/a

Option Exercise
Price ($)

Option
Expiration Date

4.67

April 20, 2020

Number of
Unearned Shares
or Units That
Have Not Vested
(#)
500,000 (3)

Market Value of  
Shares or Units 
That Have Not 
Vested 
($)(1)
$1,435,000

n/a

n/a

n/a

n/a

n/a

n/a

229,500 (4)

$658,665

247,450 (5)

$710,182

115,500 (6)

$331,485

Name

John T. Fitzgerald

William A. Hickey, Jr.

Larry G. Swets, Jr.

Hassan R. Baqar

Notes: 

(1) 

(2) 
(3) 

(4) 

(5) 

The value of the Common Shares is based on the closing price of the Common Shares on the NYSE of $2.87 as of December 31, 2018, the last trading 
day of the fiscal year.

This amount represents 40,000 options granted April 20, 2016, which were immediately vested and exercisable as of that date.

This amount represents Restricted  Common Shares awarded September 5, 2018, which become fully vested on March 28, 2024 if Mr. Fitzgerald 
remains in continuous employment with the Company through such date. 

This amount represents Restricted Common Shares awarded March 28, 2014, which become fully vested as of the tenth anniversary of the date of grant 
if the participant remains in continuous employment with the Company through such anniversary.

This amount represents Restricted Common Shares awarded September 5, 2018, which become fully vested after the satisfaction of certain performance 
conditions, as defined in the Amended and Restated Restricted Stock Award Agreement, dated September 5, 2018.  

Potential Payments Upon Termination or Change in Control

The Company maintains a severance policy for the payment of certain benefits to certain eligible employees of the Company, 
including the named executive officers.  Benefits are paid under this policy following a termination of employment in connection 
with a reduction in work force.  Under the policy, upon a qualifying termination of employment, the named executive officers are 
entitled to two weeks of severance pay for each full year of service with the Company, with a minimum of twelve weeks of 
severance pay and a maximum of 39 weeks of severance pay.  Participants are also entitled to receive subsidized benefits as 
provided under the Consolidated Omnibus Budget Reconciliation Act ("COBRA") during the severance period.

Mr. Fitzgerald, Mr. Hickey and Mr. Baqar are (or were, as of December 31, 2018, in the case of Mr. Baqar) entitled to receive 
severance benefits consisting of twelve months of base salary for a termination of employment by the Company, other than for 
“cause” or by such executive officer for "good reason" or "Constructive Termination," pursuant to the terms of their respective 
severance and employment arrangements. As defined in each of Messrs. Hickey and Baqar’s respective severance agreements, 
(A) "cause" means the executive’s involuntary termination due to commission of fraud, embezzlement, theft or other illegal or 
unethical act likely to materially damage the Company; commission of a terminable offense under the Company’s policies and 
procedures; conviction of certain crimes; breach of the executive’s confidentiality obligations or duty of loyalty; or the executive’s 
willful failure to follow the lawful directions of the Company and (B) "good reason" means the executive’s voluntary termination 
of employment due to a material reduction in the executive’s salary or authority or the Company’s breach of the severance agreement. 
As defined in Mr. Fitzgerald’s severance agreements, (A) "Cause" means the executive’s involuntary termination due to: (i) an 
intentional act of fraud, embezzlement, theft, or any other illegal act against the Company, any of which would constitute a felony; 
(ii)  the  executive’s  improper  disclosure  or  use  of  the  Company’s  confidential  information  but  only  where  the  Company  has 
established that such disclosure or use has financially and materially injured the Company; or (iii) a material breach of the executive’s 
duty of loyalty to the Company but only where the Company has established that such breach has financially and materially injured 
the Company and (B) "Constructive Termination" means the voluntary termination of the executive’s employment within forty-
five (45) days following written notice to each independent member of the Board setting forth in reasonable detail the occurrence 
of any of the following events without the executive’s written consent that is not cured by the Company within thirty (30) days 
after such notice: (i) any material diminution in job duties and responsibilities or the imposition of job requirements materially 
inconsistent with the executive’s position with the Company; (ii) a reduction in the executive’s then-current base salary, other than 

130

KINGSWAY FINANCIAL SERVICES INC.

an across-the-board reduction of no more than ten percent (10%) in the base salary of all executive level employees, (iii) a material 
reduction in the executive’s annual incentive compensation opportunities; or (iv) the executive has established that he has been 
subject to a hostile work environment.

The named executive officers have accelerated vesting of their restricted stock under certain scenarios.

Director Compensation – Narrative Description

The Company’s director compensation program is designed to provide nominal compensation for the risks and responsibilities of 
being  a  director.    Only  non-employee  directors  of  the  Board  are  remunerated for  serving  as  directors of  the  Company.  Non-
employee directors received a single retainer fee, payable quarterly, in the amount of CAD$100,000 for 2018.  The Company also 
paid an additional fee of CAD$50,000 to each of the Chairman of the Board and the Chair of the Audit Committee.  In 2018, the 
exchange rate fluctuated between $1.00 = CAD$1.2512 and CAD$1.3133.  The retainers were paid in the currency of each director’s 
country of residence. 

2018 Director Compensation

The following table provides information regarding the compensation of our non-employee directors for 2018. 

Name

Gregory P. Hannon

Terence M. Kavanagh

Doug Levine(2)

Gary R. Schaevitz(3)

Joseph D. Stilwell

Notes:

Fees Earned or Paid in 
Cash

All Other 
Compensation 

($)(1)
116,647

116,647

44,889

32,759

77,765

($)

n/a

n/a

n/a

n/a

n/a

Total 

($)

116,647

116,647

44,889

32,759

77,765

(1)  Amounts reported in this column include the annual retainer paid to each non-employee director, plus an additional fee of CAD$50,000 paid to each of 
Messrs. Kavanagh and Hannon for serving as Chairman of the Board and Chair of the Audit Committee, respectively.  The annual retainer and the additional 
fees paid to Messrs. Kavanagh and Hannon were paid in the currency of each director’s country of residence and converted to U.S. dollars based on the 
exchange rates in effect at the time the payments were made.  Messrs. Hannon and Kavanagh were paid in Canadian dollars, and Messrs. Levine, Schaevitz 
and Stilwell were paid in U.S. dollars.

(2)  Mr. Levine was elected to the Board on May 30, 2018.  He received three payments at the CAD$100,000 annualized rate.
(3)  Mr. Schaevitz was a member of the Board through May 30, 2018.  He received two payments at the CAD$100,000 annualized rate.

Compensation Committee Interlocks and Insider Participation 

The Board has a standing Compensation & Management Resources Committee (the "Compensation Committee") which operates 
pursuant to a written charter adopted by the Board.  The Compensation Committee shall consist of two or more directors, each of 
whom must satisfy the applicable independence requirements of the New York Stock Exchange and any other regulatory authorities.  
At least two members of the Committee also must qualify as “outside” directors within the meaning of Internal Revenue Code of 
1986, as amended (the "Code") Section 162(m) and as "non-employee" directors within the meaning of Rule 16b-3 under the 
Securities Exchange Act of 1934, as amended.  The Board has determined that each member of the Compensation Committee in 
the fiscal year ended December 31, 2018 was independent under the criteria established by the applicable regulatory authorities.

The Compensation Committee held three (3) meetings in the fiscal year ended December 31, 2018.  The responsibilities and duties 
of the Compensation Committee are set out in the Compensation Committee’s charter, which was amended and adopted by the 
Board on March 17, 2017 and is available on the Company’s website at www.kingsway-financial.com.

131

 
KINGSWAY FINANCIAL SERVICES INC.

The primary purpose of the Compensation Committee is to: 

(i) 

(ii) 
(iii) 

(iv) 

Assist  the  Board  in  discharging  its  responsibilities  in  respect  of  compensation  of  the  Company’s  executive 
officers and subsidiary Presidents; 
Provide recommendations to the Board in connection with directors' compensation; 
Provide recommendations to the Board in connection with succession planning for senior management of the 
Company; and
Produce an annual report for inclusion in the Proxy Statement and Annual Report on Form 10-K.

In  making  its  compensation  decisions  and  recommendations,  the  Compensation  Committee  may  take  into  account  the 
recommendations of the Chief Executive Officer with respect to the other senior officers of the Company and the President of 
each of the Company’s subsidiaries.  Other than giving such recommendations, however, the Chief Executive Officer has no formal 
role and no authority to determine the amount or form of executive and director compensation. 

The Compensation Committee shall have the sole authority to retain and terminate (or obtain the advice of) any adviser to assist 
it in the performance of its duties, but only after taking into consideration all factors relevant to the adviser’s independence from 
management, including those specified in Section 303A.05(c) of the New York Stock Exchange Listed Company Manual.  The 
Compensation Committee shall evaluate and determine whether any compensation consultant retained or to be retained by it has 
any conflict of interest in accordance with Item 407(e)(3)(iv) of Regulation S-K under the rules and regulations of the SEC.  As 
currently constituted, the Compensation Committee has never engaged a compensation consultant nor does it have any plans to 
ever do so.

As of February 27, 2020, the Compensation Committee was comprised of Joseph D. Stilwell (Chair) and Terence M. Kavanagh.

Item 12. Security Ownership of Certain Beneficial Owners and Management and Related Stockholder Matters

Securities Authorized For Issuance Under Equity Compensation Plans

Equity Compensation Plan Information

Plan Category

Equity compensation plans approved by
security holders

Equity compensation plans not approved
by security holders

Total

Number of securities to be issued 
upon exercise of outstanding 
options, warrants and rights

Weighted-average exercise price 
of outstanding options, warrants 
and rights

Number of securities remaining 
available for future issuance 
under equity compensation plans 
(excluding securities reflected in 
column (a))

(a)

40,000

—
40,000

(b)

$4.67

n/a

$4.67

(c)

—

—

—

Security Ownership of Certain Beneficial Owners and Management 

In accordance with U.S. securities laws, the following table sets forth certain information regarding beneficial ownership or control 
or direction, directly or indirectly, of the Common Shares as of February 27, 2020, by: (i) each shareholder known by the Company 
to be a beneficial owner of more than 5% of the Company’s outstanding Common Shares; (ii) each director and director nominee 
of the Company; (iii) the Chief Executive Officer and each additional executive officer named under the heading "2018 Summary 
Compensation Table" in the Proxy Statement; and (iv) all directors, director nominees and executive officers of the Company as 
a group.  The Company believes that, except as otherwise noted, each individual named has sole investment and voting power 
with respect to the Common Shares indicated as beneficially owned by such individual.  Unless otherwise indicated, the business 
address of each named person is: 150 Pierce Road, 6th Floor, Itasca, IL, 60143.

132

KINGSWAY FINANCIAL SERVICES INC.

Number of Common Shares, Including
Restricted Common Shares

Percent of Common Shares, Including 
Restricted Common Shares, Outstanding (1)

1,017,834(2)

3,096,074(3)(4)

3,096,074(3)(5)

3,096,074(3)(6)

1,270,786(7)

5,679,539(8)

1,145,809 (9)

358,677 (10)

136,743 (11)

11,422,910

4.45%

13.24%

13.24%

13.24%

5.56%

24.77%

4.98%

1.57%

*

48.13%

Beneficial Owner 

John T. Fitzgerald

Gregory P. Hannon

Terence M. Kavanagh

Oakmont Capital

Doug Levine

Joseph D. Stilwell

Larry G. Swets, Jr.

William A. Hickey, Jr.

Hassan R. Baqar

All Directors, Director Nominees and
Executive Officers as a Group (6
persons)

* Indicates less than 1%.
(1)  All percentages in this column are calculated based upon: (i) the total number of Common Shares, including Restricted Common Shares, held by the beneficial 
owner (or all directors and executive officers as a group); plus the number of options, Series B Warrants and Preferred Shares, held by the beneficial owner 
(or all directors and executive officers as a group), exercisable or convertible within sixty (60) days; divided by (ii) 22,843,909, being the total number of 
Common Shares, including Restricted Common Shares, outstanding as of February 27, 2020; plus the number of options, Series B Warrants and Preferred 
Shares, held by the beneficial owner (or all directors and executive officers as a group),  exercisable or convertible within sixty (60) days.  Accordingly, this 
calculation is not based upon maximum dilution and instead assumes that only the beneficial owner (or all directors and executive officers as a group) 
exercises or converts all options, Series B Warrants and Preferred Shares exercisable or convertible within sixty (60) days.

(2)  Mr. Fitzgerald owns 977,834 Common Shares, including 500,000 Restricted Common Shares, plus 40,000 options that are currently exercisable.
(3)  Number of Common Shares is reported as described in a Schedule 13D filed with the SEC on March 21, 2019 jointly on behalf of Oakmont Capital Inc., an 
Ontario corporation ("Oakmont"), E.J.K. Holdings Inc., an Ontario corporation ("EJK"), 1272562 Ontario Inc., an Ontario corporation ("1272562"), Gregory 
P. Hannon and Terence M. Kavanagh (collectively, the "Oakmont Group"). The business address of these shareholders is 45 St. Clair Avenue West, Suite 
400, Toronto, Ontario, M4V 1K9 Canada.

(4)  Mr. Hannon has sole voting power and sole dispositive power with respect to 22,500 Common Shares owned directly by him or through a self-directed 
Retirement Savings Plan and 4,500 Common Shares owned directly by two trusts for Mr. Hannon’s children (Mr. Hannon is the sole trustee of both of these 
trusts). In addition, Mr. Hannon has shared voting power and shared dispositive power with respect to (i) 3,000 Common Shares owned directly by 1272562, 
by virtue of his ownership of all of the outstanding voting stock of 1272562; (ii) 4,000 Common Shares owned directly by Gilter Inc., an Ontario corporation 
of which all of the outstanding voting stock is owned by the Gregory Hannon Family Trust (Mr. Hannon is one of two trustees of this trust); (iii) 2,468,037 
Common Shares owned directly by Oakmont, by virtue of his ownership of all of the capital stock of 1272562, and 1272562’s ownership of 50% of the 
outstanding voting stock of Oakmont and its right to nominate one of the two members of the Board of Directors of Oakmont; (iv) 82,143 Common Shares 
issuable upon the conversion of 13,143 shares of Preferred Shares owned by Oakmont; (v) 463,394 Common Shares currently issuable upon exercise of 
Series B Warrants owned by Oakmont; and (vi) 13,750 Common Shares owned directly by Mr. Hannon’s spouse. Mr. Hannon may be deemed to be a 
beneficial owner of the balance of the 3,096,074 Common Shares beneficially owned by the Oakmont Group, by virtue of his participation in the Oakmont 
Group.

(5)  Mr. Kavanagh has sole voting power and sole dispositive power with respect to 26,875 Common Shares owned through a self-directed Retirement Savings 
Plan, 1,750 Common Shares owned directly and 125 Common Shares owned directly by a trust for his nephew (Mr. Kavanagh is the sole trustee). Mr. 
Kavanagh has shared voting power and shared dispositive power with respect to (i) the 6,000 Common Shares owned directly by EJK, by virtue of Mr. 
Kavanagh’s ownership of all of the outstanding voting stock of EJK; (ii) the 2,468,037 Common Shares owned directly by Oakmont, by virtue of Mr. 
Kavanagh’s ownership of all the outstanding voting stock of EJK, and EJK’s ownership of 50% of the outstanding voting stock of Oakmont and its right to 
nominate one of the two members of the Board of Directors of Oakmont; (iii) 82,143 Common Shares issuable upon the conversion of 13,143 shares of 
Preferred Shares owned by Oakmont; and (iv) 463,394 Common Shares currently issuable upon exercise of Series B Warrants owned by Oakmont. Mr. 
Kavanagh may be deemed to be a beneficial owner of the balance of the 3,096,074 Common Shares beneficially owned by the Oakmont Group, by virtue 
of his participation in the Oakmont Group.

(6)  Oakmont has sole voting power and sole dispositive power with respect to: (i) the 2,468,037 Common Shares that it owns directly; (ii) 82,143 Common 
Shares issuable upon the conversion of 13,143 shares of Preferred Shares owned by Oakmont; and (iii) 463,394 Common Shares currently issuable upon 
exercise of Series B Warrants owned by Oakmont. Oakmont may be deemed to be a beneficial owner of the balance of the 3,096,074 Common Shares 
beneficially owned by the Oakmont Group, by virtue of its participation in the Oakmont Group.

(7)  Mr. Levine directly owns 991,484 Common Shares.  Mr. Levine indirectly owns 90,200 Common Shares, through the holdings of family members, and 

189,102 Common Shares via a trust. 

133

KINGSWAY FINANCIAL SERVICES INC.

(8)  Number of Common Shares is reported as described in a Schedule 13D filed with the SEC on March 29, 2019 on behalf of Stilwell Activist Fund, L.P., a 
Delaware limited partnership ("Stilwell Activist Fund"); Stilwell Activist Investments, L.P., a Delaware limited partnership ("Stilwell Activist Investments"); 
Stilwell Associates, L.P., a Delaware limited partnership ("Stilwell Associates"); Stilwell Value Partners VII, L.P., a Delaware limited partnership ("Stilwell 
Value Partners VII"); Stilwell Value LLC, a Delaware limited liability company ("Stilwell Value LLC" and, collectively with Stilwell Activist Fund, Stillwell 
Activist Investments, Stilwell Associates, and Stilwell Value Partners VII, the "Investment Partnership"); and Joseph D. Stilwell, a U.S. citizen. The Investment 
Partnerships are private investment partnerships engaged in the purchase and sale of securities for their own accounts. Stilwell Value LLC is the general 
partner of each of the Investment Partnerships, and Mr. Stilwell is the managing member and owner of Stilwell Value LLC. The Investment Partnerships 
have shared voting and shared dispositive power over 5,679,539 Common Shares, consisting of (i) 5,597,396 Common Shares owned of record, and (ii)  
82,143 Common Shares issuable upon the conversion of 13,143 shares of Preferred Shares. The members of the Group also hold Series B Warrants to 
purchase  708,347  Common  Shares  currently  issuable  upon  exercise  of  Series  B Warrants;  however,  each  of  the  Investment  Partnerships  has  entered  a 
Statement of Undertaking with the Company in which they undertook not to exercise the Series B Warrants until the earlier of: (i) July 15, 2020; or (ii) the 
execution by all of the Investment Partnerships and the Company of a written instrument that terminates the Statement of Undertaking.. The business address 
of this shareholder is 111 Broadway, 12th Floor, New York, NY 10006.

(9)  Mr. Swets owns 963,273 Common Shares, including 247,450 Restricted Common Shares; and 182,536 Common Shares currently issuable upon exercise 

of Series B Warrants.

(10)  Mr. Hickey owns 333,177 Common Shares, including 229,500 Restricted Common Shares; and 25,500 Common Shares currently issuable upon exercise 

of Series B Warrants.

(11)  Mr. Baqar owns 124,243 Common Shares and 12,500 Common Shares currently issuable upon exercise of Series B Warrants.

Item 13. Certain Relationships and Related Transactions, and Director Independence

Certain Relationships and Transactions with Related Persons

For a description of the Company’s relationships and transactions with related persons, see Note 30, "Related Parties," to the 
Consolidated Financial Statements.

Item 14. Principal Accounting Fees and Services 

Audit Fees

The aggregate fees billed by RSM US LLP ("RSM US") for professional services rendered for the audit of the consolidated financial 
statements of the Company and its subsidiaries, including expenses reimbursed, were $1,274,171 related to fiscal year 2018.  The 
aggregate fees billed by BDO USA, LLP ("BDO USA") for professional services rendered for the audit of the consolidated financial 
statements of the Company and its subsidiaries, and for the reviews of the Company’s quarterly financial statements, including 
expenses reimbursed, were $108,768 for partial year worked performed in fiscal year 2018 and $957,237 related to fiscal year 
2017.

Audit-Related Fees

The aggregate audit-related fees, including expenses reimbursed, billed by RSM US for services rendered to the Company and its 
subsidiaries pertaining to the audit of the 401(k) plan were $18,703 related to fiscal year 2018.  The aggregate audit-related fees, 
including expenses reimbursed, billed by BDO USA for services rendered to the Company and its subsidiaries pertaining to the 
audit of the 401(k) plan were $17,910 related to fiscal year 2017.

Tax Fees

The aggregate fees, including expenses reimbursed, billed by RSM US for tax compliance, tax advice and tax planning serviceswere 
zero in fiscal year 2018.  The aggregate fees, including expenses reimbursed, billed by BDO USA for tax compliance, tax advice 
and tax planning services were zero in fiscal years 2018 and 2017. 

All Other Fees

The aggregate fees, including expenses reimbursed, billed by RSM US for services other than the services reported above under 
"Audit Fees," "Audit-Related Fees" and "Taxes" were zero in fiscal year 2018.  The aggregate fees, including expenses reimbursed, 
billed by BDO USA for services other than the services reported above under "Audit Fees," "Audit-Related Fees" and "Taxes" 
were $60,015 related to fiscal year 2018 and $4,175 related to fiscal year 2017.

134

KINGSWAY FINANCIAL SERVICES INC.

135

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 2018 Annual 
Report on Form 10-K.  

Reports of Independent Registered Public Accounting Firms

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 

Investments Other Than Investments in Related Parties

Schedule II 

Financial Information of Registrant (Parent Company)

Schedule III 

Valuation and Qualifying Accounts

(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

136

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
KINGSWAY FINANCIAL SERVICES INC.

SCHEDULE I. Investments Other Than Investments in Related Parties

(in thousands)

Fixed maturities:

Cost or
Amortized
Cost

December 31, 2018

Amount Shown
on Consolidated
Balance Sheet

Fair Value

U.S. government, government agencies and authorities

$

5,594

$

5,547

$

States, municipalities and political subdivisions

Mortgage-backed

Corporate

Total fixed maturities

Equity investments:

Common stock

Warrants

Total equity investments
Limited liability investments (1)
Limited liability investments, at fair value

Investments in private companies

Real estate investments
Other investments (1)
Short-term investments (1)
Total investments

621

3,256

2,961

12,432

1,286

988

2,274

4,790

26,015

2,465

10,225

2,079

152

607

3,186

2,920

12,260

801

55

856

—

26,015

3,090

10,662

—

—

$

60,432

$

52,883

$

5,547

607

3,186

2,920

12,260

801

55

856

4,790

26,015

3,090

10,662

2,079

152

59,904

(1) Cost approximates fair value for limited liability investments, other investments and short-term investments.

See accompanying report of independent registered accounting firm.

137

KINGSWAY FINANCIAL SERVICES INC.

SCHEDULE II.  Financial Information of Registrant (Parent Company)

Parent Company Balance Sheets 

(in thousands)

December 31, 2018

December 31, 2017

Assets
Investments in subsidiaries
Equity investments
Cash and cash equivalents
Investment in investee
Other assets
Total Assets
Liabilities and Shareholders' Equity
Liabilities:
Accrued expenses and other liabilities
Total Liabilities

Class A preferred stock

Shareholders' Equity:
Common stock
Additional paid-in capital
Accumulated deficit
Accumulated other comprehensive income (loss)
Shareholders' equity attributable to common shareholders
Total Liabilities, Class A preferred stock and Shareholders' Equity

See accompanying report of independent registered accounting firm.

$

$

$

$

16,843
71
759
951
82
18,706

444
444

5,800

—
353,890
(382,196)
40,768
12,462
18,706

$

$

$

$

39,186
491
688
5,230
3,134
48,729

2,183
2,183

5,180

—
356,171
(310,953)
(3,852)
41,366
48,729

138

KINGSWAY FINANCIAL SERVICES INC.

SCHEDULE II.  Financial Information of Registrant (Parent Company)

Parent Company Statements of Operations

(in thousands)

Revenues:

Net investment (loss) income
Loss on change in fair value of equity investments

Total revenues
Expenses:

General and administrative expenses
Non-operating other expense (income)
Equity in net loss (income) of investee

Total expenses
Loss from continuing operations before income tax expense (benefit) and
equity in loss of subsidiaries
Income tax expense (benefit)
Equity in loss of subsidiaries
Net loss

See accompanying report of independent registered accounting firm.

Years ended December 31,
2017

2018

$

$

$

(2)
(211)
(213)

223
132
2,499
2,854

(3,067)
—
(25,269)
(28,336)

$

35
—
35

3,760
(165)
(2,115)
1,480

(1,445)
—
(10,164)
(11,609)

139

KINGSWAY FINANCIAL SERVICES INC.

SCHEDULE II.  Financial Information of Registrant (Parent Company)

Parent Company Statements of Comprehensive Loss  

(in thousands)

Net loss
Other comprehensive income (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 income (loss) of subsidiaries
Other comprehensive income (loss)
Comprehensive loss

Years ended December 31,
2017

2018

$

(28,336) $

(11,609)

—
—
—
4,124
4,124
(24,212) $

(139)
—
(139)
(3,504)
(3,643)
(15,252)

$

 (1) Net of income tax expense (benefit) of $0 and $0 in 2018 and 2017, respectively

See accompanying report of independent registered accounting firm.

140

KINGSWAY FINANCIAL SERVICES INC.

SCHEDULE II.  Financial Information of Registrant (Parent Company)

Parent Company Statements of Cash Flows 

(in thousands)

Cash provided by (used in):
Operating activities:
Net loss
Adjustments to reconcile net loss to net cash used in operating activities:

Equity in net loss of subsidiaries
Equity in net loss (income) of investee
Dividend received from investee
Stock-based compensation (benefit) expense, net of forfeitures
Loss on change in fair value of equity investments
Other, net

Net cash used in operating activities
Investing activities:
Purchases of equity investments
Proceeds from sale of equity investments
Proceeds from sale of investee
Net cash provided by (used in) investing activities
Financing activities:
Proceeds from issuance of common stock, net
Capital contributions to subsidiaries
Net cash used in financing activities
Net increase (decrease) in cash and cash equivalents
Cash and cash equivalents at beginning of period
Cash and cash equivalents at end of period

See accompanying report of independent registered accounting firm.

Years ended December 31,
2017
2018

$

(28,336)

$

(11,609)

25,269
2,499
780
(1,661)
211
138
(1,100)

—
215
1,001
1,216

—
(45)
(45)
71
688
759

$

10,164
(2,115)
—
1,186
—
(404)
(2,778)

(630)
—
—
(630)

(47)
(7,326)
(7,373)
(10,781)
11,469
688

$

141

 
KINGSWAY FINANCIAL SERVICES INC.

SCHEDULE III. Valuation and Qualifying Accounts

(in thousands)

Balance at
Beginning
of Year

Charged to
Income Tax
(Benefit)
Expense

Tax Act
Rate Change

Disposals
and Other

Balance at
End of Year

Valuation Allowance for Deferred Tax
Assets:

Year Ended December 31, 2018

Year Ended December 31, 2017

$

$

173,965

268,418

$

$

4,562

3,169

$

$

— $
(105,598) $

(7,071) $
$
7,976

171,456

173,965

See accompanying report of independent registered accounting firm.

Item 16.  Form 10-K Summary

None.

142

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:

February 27, 2020

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

Chief Executive Officer, President and Director

February 27, 2020

/s/ William A. Hickey, Jr.
William A. Hickey, Jr.

Executive Vice President and Chief Financial Officer
(principal financial and accounting officer)

February 27, 2020

/s/ Terence Kavanagh
Terence Kavanagh

/s/ Gregory Hannon
Gregory Hannon

/s/ Doug Levine
Doug Levine

/s/ Joseph Stilwell
Joseph Stilwell

Chairman of the Board and Director

February 27, 2020

Director

Director

Director

February 27, 2020

February 27, 2020

February 27, 2020

143

 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
KINGSWAY FINANCIAL SERVICES INC.

EXHIBIT INDEX

Exhibit Description

2.1

2.2

2.3

2.4

3.1

3.2

4.1

4.2

4.3

4.4

4.5

4.6

4.7

4.8

10.1

10.2

Stock Purchase Agreement, dated April 1, 2015, by and among National General Holdings Corp., as Buyer, and 
Kingsway America Inc. and Mendota Insurance Company, as Sellers (included as Exhibit 2.1 to the Form 8-K, 
filed April 7, 2015, and incorporated herein by reference).

Stock Purchase Agreement, dated as of May 17, 2016, by and among CMC Acquisition, LLC, CRIC TRT 
Acquisition LLC and BNSF-Delpres Investments Ltd. (included as Exhibit 2.1 to the Form 8-K, filed July 20, 
2016, and incorporated herein by reference).

Amendment to Stock Purchase Agreement, dated as of June 17, 2016, by and among CMC Acquisition, LLC, 
CRIC TRT Acquisition LLC, and BNSF-Delpres Investments Ltd. (included as Exhibit 2.1 to the Form 8-K, filed 
June 17, 2016, and incorporated herein by reference).

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).

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 among 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 among 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).

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). *

Form of Subscription Agreement (included as Exhibit 10.1 to the Form 8-K, filed December 27, 2013, and 
incorporated herein by reference).

144

 
 
 
 
 
 
 
KINGSWAY FINANCIAL SERVICES INC.

10.3

10.4

10.5

10.6

Registration Rights Agreement, dated as of 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). *

Agreement to Buyout and Release, dated as of February 24, 2015, by and between 1347 Advisors LLC and 1347 
Property Insurance Holdings, Inc. (included as Exhibit 10.1 to the Form 8-K, filed February 27, 2015, and 
incorporated herein by reference).

Stockholders’ Agreement, dated as of July 14, 2016, by and between CMC Industries, Inc., CMC Acquisition LLC 
and CRIC TRT Acquisition LLC (included as Exhibit 10.1 to Form 8-K, filed July 20, 2016, and incorporated 
herein by reference).

10.7 Management Services Agreement, dated as of July 14, 2016, by and between TRT LeaseCo, LLC and DGI-BNSF 
Corp. (included as Exhibit 10.2 to Form 8-K, filed July 20, 2016, and incorporated herein by reference).

10.8

10.9

10.10

10.11

TRT LeaseCo, LLC 4.07% Senior Secured Note, Due May 15, 2034 (included as Exhibit 10.3 to Form 10-Q, filed 
August 4, 2016, and incorporated herein by reference).

Deed of Trust, Security Agreement, Assignment of Leases and Rents and Fixture Filing Statement, dated as of 
March 12, 2015, from TRT LeaseCo, LLC to Malcolm Morris, as Deed of Trust Trustee for the benefit of Wells 
Fargo Bank Northwest, N.A., as trustee (included as Exhibit 10.4 to Form 10-Q, filed August 4, 2016, and 
incorporated herein by reference).

Lease between TRT LeaseCo, LLC, as Landlord, and BNSF Railway Company (f/k/a The Burlington Northern and 
Santa Fe Railway Company), as Tenant, dated as of June 1, 2014 (included as Exhibit 10.5 to Form 10-Q, filed 
August 4, 2016, and incorporated herein by reference).

Stock Purchase Agreement, dated as of November 9, 2016, by and between the Company and GrizzlyRock 
Institutional Value Partners, LP (included as Exhibit 10.1 to Form 8-K, filed November 16, 2016, and incorporated 
herein by reference).

10.12

Stock Purchase Agreement, dated as of November 9, 2016, by and between the Company and W.H.I. Growth Fund 
Q.P., L.P. (included as Exhibit 10.2 to Form 8-K, filed November 16, 2016, and incorporated herein by reference).

10.13

10.14

10.15

10.16

10.17

10.18

10.19

Stock Purchase Agreement, dated as of November 9, 2016, by and between the Company and Yorkmont Capital 
Partners, LP (included as Exhibit 10.3 to Form 8-K, filed November 16, 2016, 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).

Offer Letter, dated as of September 5, 2018, by and 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).

145

KINGSWAY FINANCIAL SERVICES INC.

10.20

10.21

10.22

10.23

10.24

10.25

Severance Agreement, dated as of September 5, 2018, by and 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).

Restricted Stock Agreement, dated as of September 5, 2018, by and 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).

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).

Separation Agreement and Release, dated as of September 5, 2018, by and between Kingsway America Inc. and 
Larry G. Swets, Jr. (included as Exhibit 10.6 to Form 8-K, filed September 10, 2018, and incorporated herein by 
reference).

Senior Advisor Agreement, dated as of September 5, 2018, by and between Kingsway America Inc. and Larry G. 
Swets, Jr. (included as Exhibit 10.7 to Form 8-K, filed September 10, 2018, and incorporated herein by reference).

Amended and Restated Restricted Stock Agreement, dated as of September 5, 2018, by and between the Company 
and Larry G. Swets, Jr. (included as Exhibit 10.8 to Form 8-K, filed September 10, 2018, and incorporated herein 
by reference).

10.26 Membership Interest Purchase Agreement, dated as of September 5, 2018, by and between 1347 Capital LLC and 

IGI Partners, LLC (included as Exhibit 10.9 to Form 8-K, filed September 10, 2018, and incorporated herein by 
reference).

10.27

14

Letter Agreement, dated as of May 30, 2018, by and between the Company and Larry Swets (included as Exhibit 
10.9 to Form 10-Q, Filed November 9, 2018, and incorporated herein by reference).

Kingsway Financial Services Inc. Code of Business Conduct & Ethics (included as Exhibit 14 to Form 10-K, Filed 
March 16, 2018, and incorporated herein by reference).

21

Subsidiaries of Kingsway Financial Services Inc.

23.1

Consent of RSM US LLP

23.2

Consent of BDO USA, LLP

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

32.2

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

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 XBRL Instance Document

101.SCH XBRL Taxonomy Extension Schema

101.CAL XBRL Taxonomy Extension Calculation Linkbase

101.DEF XBRL Taxonomy Extension Definition Linkbase

101.LAB XBRL Taxonomy Extension Label Linkbase

101.PRE XBRL Taxonomy Extension Presentation Linkbase

*  Management contract or compensatory plan or arrangement.

146

 
Subsidiaries of Kingsway Financial Services Inc.

Exhibit 21

Subsidiaries

Kingsway America II Inc.

1347 Advisors LLC

1347 Capital LLC

Itasca Investors LLC

Itasca Capital Corp.

1347 Venture Opportunity LLC

American Country Underwriting Agency Inc.

Argo Management Group, LLC

ARM Holdings, Inc.

Mattoni Insurance Brokerage, Inc.

Appco Finance Corporation

CMC Acquisition LLC

CMC Industries Inc.

Texas Rail Terminal LLC

TRT Leaseco, LLC

DPM SPV, LLC

Flower Portfolio 001, LLC

KAI Management Services Inc.

Kingsway America Inc.

Kingsway Amigo Insurance Company

Kingsway America Agency Inc.

Kingsway General Insurance Company

Kingsway LGIC Holdings, LLC

Kingsway Reinsurance Corporation

Kingsway Warranty Holdings LLC

IWS Acquisition Corporation

Trinity Warranty Solutions LLC

Net Lease Investment Grade Portfolio LLC

Professional Warranty Services LLC

                Professional Warranty Service Corporation

Jurisdiction of Incorporation/Organization

Delaware

Delaware

Delaware

Delaware

Delaware

Delaware

Illinois

Delaware

Illinois

Washington

Pennsylvania

Delaware

Texas

Delaware

Delaware

Delaware

Delaware

Illinois

Delaware

Florida

Illinois

Ontario

Delaware

Barbados

Delaware

Florida

Delaware

Delaware

Delaware

Virginia

Exhibit 23.1

Consent of Independent Registered Public Accounting Firm

We consent to the incorporation by reference in the Registration Statements (Nos. 333-228286, 333-196633 and 333-194108) 
on Form S-8 of Kingsway Financial Services Inc. of our report dated February 27, 2020 relating to the consolidated financial 
statements and the financial statement schedules of Kingsway Financial Services Inc., appearing in this Annual Report on 
Form 10-K of Kingsway Financial Services Inc. for the year ended December 31, 2018.

/s/ RSM US LLP

Chicago, Illinois
February 27, 2020

Exhibit 23.2

Consent of Independent Registered Public Accounting Firm

Kingsway Financial Services Inc.
Itasca, Illinois

We hereby consent to the incorporation by reference in the Registration Statements on Form S -8 (Nos. 333-228286, 333-196633 
and 333-194108) of Kingsway Financial Services Inc. of our report dated March 16, 2018 except for Notes 3, 6 and 28, as to which 
the date is February 27, 2020, relating to the consolidated financial statements and schedules as of and for the year ended December 
31, 2017 which appears in this Form 10-K.

/s/ BDO USA, LLP
Grand Rapids, Michigan

February 27, 2020

EXHIBIT 31.1 

Certification of Chief Executive Officer pursuant to Section 302 of the Sarbanes-Oxley Act of 2002

CERTIFICATION PURSUANT TO SECTION 302 

I, John T. Fitzgerald, certify that: 

1. I have reviewed this report on Form 10-K of Kingsway Financial Services Inc.; 

2. Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact 
necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading 
with respect to the period covered by this report; 

3. Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all 
material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods 
presented in this report; 

4. The registrant's other certifying officer and I are responsible for establishing and maintaining disclosure controls and 
procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) and internal control over financial reporting (as 
defined in Exchange Act Rules 13a-15(f) and 15d-15(f)) for the registrant and have: 

a) Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed 
under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, 
is made known to us by others within those entities, particularly during the period in which this report is being prepared; 

b) Designed such internal control over financial reporting, or caused such internal control over financial reporting to be 
designed under our supervision, to provide reasonable assurance regarding the reliability of financial reporting and the 
preparation of financial statements for external purposes in accordance with generally accepted accounting principles; 

c) Evaluated the effectiveness of the registrant's disclosure controls and procedures and presented in this report our 
conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this 
report based on such evaluation; and 

d) Disclosed in this report any change in the registrant's internal control over financial reporting that occurred during the 
registrant's most recent fiscal quarter (the registrant's fourth fiscal quarter in the case of an annual report) that has 
materially affected, or is reasonably likely to materially affect, the registrant's internal control over financial reporting; and

5. The registrant's other certifying officer and I have disclosed, based on our most recent evaluation of internal control over 
financial reporting, to the registrant's auditors and the audit committee of the registrant's board of directors (or persons 
performing the equivalent functions): 

a) All significant deficiencies and material weaknesses in the design or operation of internal control over financial 
reporting which are reasonably likely to adversely affect the registrant's ability to record, process, summarize and report 
financial information; and 

b) Any fraud, whether or not material, that involves management or other employees who have a significant role in the 
registrant's internal control over financial reporting. 

Date: February 27, 2020 

By /s/ John T. Fitzgerald

John T. Fitzgerald, Chief Executive Officer and President

(Principal Executive Officer)

EXHIBIT 31.2 

CERTIFICATION 

Certification of Chief Financial Officer pursuant to Section 302 of the Sarbanes-Oxley Act of 2002

I, William A. Hickey, Jr., certify that: 

1. I have reviewed this Form 10-K of Kingsway Financial Services Inc.; 

2. Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact 
necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading 
with respect to the period covered by this report; 

3. Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all 
material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods 
presented in this report; 

4. The registrant's other certifying officer and I are responsible for establishing and maintaining disclosure controls and 
procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) and internal control over financial reporting (as 
defined in Exchange Act Rules 13a-15(f) and 15d-15(f)) for the registrant and have: 

(a) Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed 
under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, 
is made known to us by others within those entities, particularly during the period in which this report is being prepared; 

(b) Designed such internal control over financial reporting, or caused such internal control over financial reporting to be 
designed under our supervision, to provide reasonable assurance regarding the reliability of financial reporting and the 
preparation of financial statements for external purposes in accordance with generally accepted accounting principles; 

(c) Evaluated the effectiveness of the registrant's disclosure controls and procedures and presented in this report our 
conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this 
report based on such evaluation; and 

(d) Disclosed in this report any change in the registrant's internal control over financial reporting that occurred during the 
registrant's most recent fiscal quarter (the registrant's fourth fiscal quarter in the case of an annual report) that has 
materially affected, or is reasonably likely to materially affect, the registrant's internal control over financial reporting; and

5. The registrant's other certifying officer and I have disclosed, based on our most recent evaluation of internal control over 
financial reporting, to the registrant's auditors and the audit committee of the registrant's board of directors (or persons 
performing the equivalent functions): 

(a) All significant deficiencies and material weaknesses in the design or operation of internal control over financial 
reporting which are reasonably likely to adversely affect the registrant's ability to record, process, summarize and report 
financial information; and 

(b) Any fraud, whether or not material, that involves management or other employees who have a significant role in the 
registrant's internal control over financial reporting. 

Date: February 27, 2020 

By /s/ William A. Hickey, Jr.

William A. Hickey, Jr., Chief Financial Officer and Executive Vice President

(Principal Financial Officer)

EXHIBIT 32.1 

CERTIFICATION PURSUANT TO 

18 U.S.C. SECTION 1350, 

AS ADOPTED PURSUANT TO 

SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002 

In connection with the Annual Report on Form 10-K of Kingsway Financial Services Inc. (the “Company”) for the year ended 
December 31, 2018 as filed with the Securities and Exchange Commission on the date hereof (the "Report"), the undersigned 
John T. Fitzgerald, the Chief Executive Officer and Principal Executive Officer of the Company, hereby certifies, pursuant to 
18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002, that, to the best of the 
undersigned's knowledge and belief: 

(1) the Report fully complies with the requirements of Section 13(a) or 15(d) of the Securities Exchange Act of 1934; and 

(2) the information contained in the Report fairly presents, in all material respects, the financial condition and results of 
operations of the Company.

Date: February 27, 2020 

By /s/ John T. Fitzgerald

John T. Fitzgerald, Chief Executive Officer and President 

(Principal Executive Officer) 

EXHIBIT 32.2

CERTIFICATION PURSUANT TO 

18 U.S.C. SECTION 1350, 

AS ADOPTED PURSUANT TO 

SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002 

In connection with the Annual Report on Form 10-K of Kingsway Financial Services Inc. (the “Company”) for the year ended 
December 31, 2018 as filed with the Securities and Exchange Commission on the date hereof (the "Report"), the undersigned 
William A. Hickey, Jr., the Chief Financial Officer and Principal Financial Officer of the Company, hereby certifies, pursuant to 
18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002, that, to the best of the 
undersigned's knowledge and belief: 

(1) the Report fully complies with the requirements of Section 13(a) or 15(d) of the Securities Exchange Act of 1934; and 

(2) the information contained in the Report fairly presents, in all material respects, the financial condition and results of 
operations of the Company.

Date: February 27, 2020 

By /s/ William A. Hickey, Jr.

William A. Hickey, Jr., Chief Financial Officer and Executive Vice President

(Principal Financial Officer)