Exhibit 99.1

KINGSWAY REPORTS First QUARTER 2025 FINANCIAL RESULTS

Management to Host Conference Call Today at 5 p.m. ET

Chicago - May 8, 2025 - (NYSE: KFS) Kingsway Financial Services Inc. (“Kingsway” or the “Company”), the only publicly-traded US company employing the Search Fund model to acquire and build great businesses, today announced its operating results for the three months ended March 31, 2025.

First Quarter 2025 Consolidated Financial Highlights

Recent Business Highlights

Management Commentary

“Kingsway made solid progress in the first quarter of 2025, both financially and strategically,” said JT Fitzgerald, Kingsway’s President and CEO. “KSX revenue grew 23.3% year-on-year and KSX adjusted EBITDA grew 23.2% year-on-year. Under the surface, our operator CEO’s are executing their strategic plans to position their businesses for accelerating growth on both the top and bottom lines.

“Importantly, Kingsway has already completed two acquisitions this year under the KSX umbrella. In March, Kingsway acquired Bud’s Plumbing and established KSX Skilled Trade Services, our third KSX operating platform. In April, SPI Software acquired ViewPoint to accelerate its product roadmap and to open up exciting opportunities for geographic and market expansion. I’m thrilled to welcome Rob Casper, who leads the KSX Skilled Trades Services platform, as our newest operator CEO, and to continue supporting Drew Richard, President of SPI Software, who leads the KSX Vertical Market Solutions platform.

“I’m also encouraged by the momentum building in Kingsway’s Extended Warranty segment. Although adjusted EBITDA declined year-over-year in the first quarter, the business has returned to growth in cash sales, and key forward-looking indicators of profitability are now solidly positive. After two challenging years marked by industry headwinds and cyclical pressures, Extended Warranty appears to be entering a more favorable phase of recovery, with early signs pointing to both healthy top-line growth and renewed operating leverage.

“Kingsway is well-positioned for the months and years ahead, and the first quarter was another step in the right direction,” concluded Mr. Fitzgerald. “Our KSX deal pipeline is robust, and we remain committed to employing the Search Fund model to acquire and grow asset-light, profitable, and recurring revenue services businesses that can deliver compelling returns for our shareholders.”

Conference Call and Webcast

Management will host a conference call at 5 p.m. Eastern Time today to discuss the results and host a live Q&A session. Additionally, investors may also submit questions via email to: [email protected].

Conference Call Information

Date: Thursday, May 8, 2025

Time: 5 p.m. Eastern Time

Toll Free: 877-545-0523; Code: 131755

International: 973-528-0016; Code: 131755

Live Webcast Link: https://bit.ly/3YykRi9

Conference Call Replay Information

Toll Free: 877-481-4010

International: 919-882-2331

Replay Passcode: 52464

Replay Webcast Link: https://bit.ly/3YykRi9

About the Company

Kingsway Financial Services Inc. (“Kingsway”) (NYSE: KFS) is the only publicly-traded US company employing the Search Fund model to acquire and build great businesses.

Kingsway owns and operates a collection of high-quality B2B and B2C services companies that are asset-light, growing, profitable, and that have recurring revenues. Kingsway seeks to compound long-term shareholder value on a per share basis via its decentralized management model, its talented team of operators, and its tax-advantaged corporate structure.

Non U.S. GAAP Financial Measure

Management believes that non-GAAP adjusted EBITDA, when presented in conjunction with comparable GAAP measures, provides useful information about the Company's operating results and enhances the overall ability to assess the Company's financial performance. Management uses non-GAAP adjusted EBITDA, together with other measures of performance under GAAP, to compare the relative performance of operations in planning, budgeting and reviewing the performance of its business. Non-GAAP adjusted EBITDA allows investors to make a more meaningful comparison between the Company’s core business operating results over different periods of time. Management believes that non-GAAP adjusted EBITDA, when viewed with the Company's results under GAAP and the accompanying reconciliations, provides useful information about the Company's business without regard to potential distortions. By eliminating potential differences in results of operations between periods caused by the factors listed in the attached schedules, Management believes that non-GAAP adjusted EBITDA can provide useful additional basis for comparing the current performance of the underlying operations being evaluated. Investors should consider this non-GAAP measure in addition to, not as a substitute for or as superior to, financial reporting measures prepared in accordance with GAAP. Investors are encouraged to review the Company's financial results prepared in accordance with GAAP to understand the Company's performance taking into account all relevant factors.

Forward-Looking Statements

This press release may include "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 that are not historical facts and involve risks and uncertainties that could cause actual results to differ materially from those expected and projected. Words such as "expects," "believes," "anticipates," "intends," "estimates," "seeks" and variations and similar words and expressions are intended to identify such forward-looking statements; however, the absence of any such words does not mean that a statement is a not a forward-looking statement. Such forward-looking statements relate to future events or future performance, but reflect Kingsway management's current beliefs, based on information currently available. A number of factors could cause actual events, performance or results to differ materially from the events, performance and results discussed in the forward-looking statements. For information identifying important factors that could cause actual results to differ materially from those anticipated in the forward-looking statements, please refer to the section entitled "Risk Factors" in the Company's 2024 Annual Report on Form 10-K and subsequent Form 10-Qs and Form 8-Ks filed with the Securities and Exchange Commission. Except as expressly required by applicable securities law, 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.

Additional Information

Additional information about Kingsway, including a copy of its Annual Reports, can be accessed on the EDGAR section of the U.S. Securities and Exchange Commission's website at www.sec.gov, on the Canadian Securities Administrators' website at www.sedar.com, or through the Company's website at www.kingsway-financial.com.

For Media Inquiries:

Hayden IR
   James Carbonara
   (646) 755-7412
   [email protected] 

For Company Inquiries:

Kingsway Financial Services Inc.

Kent Hansen, CFO

(312) 766-2163

[email protected]

Kingsway Financial Services Inc.

Reconciliation of GAAP Net Income (Loss) to Non-GAAP Adjusted Consolidated EBITDA

(in thousands)

(UNAUDITED)

Kingsway Financial Services Inc.

Reconciliation of Extended Warranty Segment Operating Income to Non-GAAP Adjusted EBITDA

and Pro Forma Non-GAAP Adjusted EBITDA

(in thousands)

(UNAUDITED)

Kingsway Financial Services Inc. 

Reconciliation of KSX Segment Operating Income to Non-GAAP Adjusted EBITDA 

(in thousands) 

(UNAUDITED)