Kingsway Financial Services : May 17, 2026 Investor Presentation

About this update from Kingsway Corporation

NYSE: KFS I stor Day May 18, 2026 Building through Search Agenda Building through Search The Last 12 Months at Kingsway 2026 Outlook The Equity Story Capital Markets Update Theory to Action: KBS Deployment Operator Spotlight: Miles Mamon Operator Spotlight: Davide Zanchi Q&A Fireside Chat About Us 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. Kingsway Investor Days: Three-Year Narrative Arc From "Vision" to "System" to "Proof". Vision System Proof 2024 2025 Today A repeatable model to compound intrinsic value per share. An operating system to turn good acquisitions into great businesses. Tangible evidence Kingsway's vision is becoming a reality. The Last 12 Months at Kingsway 2025 Scorecard Kingsway delivered on the targets we set out last year. ACQUISITIONS What We Said Target 3-5 high-quality acquisitions per year What We Did Completed 6 acquisitions in 2025 including Bud's Plumbing, ViewPoint, Roundhouse, AAA, The HR Team, and Southside Plumbing EBITDA GROWTH Run-rate adjusted EBITDA of $18-$19M Achieved Portfolio LTM EBITDA of $22-$23M as of March 31, 2026 Kingsway Acquired Six High-Quality B2B and B2C Services Businesses Each acquisition met or exceeded our target underwriting IRR hurdle rate of 30%+. Skilled Trades Skilled Trades Skilled Trades MRO Services B2B Services Vertical Market SaaS KSX is Majority of Revenue and EBITDA for First Time Kingsway's public search fund model is now the primary driver of shareholder value creation. Why this matters Validates the strategic pivot from legacy insurance holding company to operator-led public search platform Removes investor confusion about Kingsway's strategy and business model KSX's high-growth profile now drives the consolidated equity story Underpins rationale for retiring the 'Financial Services' name 2026 Outlook Strong Start to 2026 Operating performance is ahead of internal expectations, while continuing to execute disciplined M&A. Kingsway delivered a strong first quarter of 2026, with profits at both KSX and Extended Warranty coming in ahead of budget . KSX achieved record quarterly revenue and record quarterly adjusted EBITDA in Q1 2026 - in a seasonally light quarter for many KSX businesses. Reiterated expectations for double-digit organic growth in revenue and profit at both KSX and Extended Warranty in 2026. Reiterated target of 3-5 acquisitions in 2026. On January 7, announced acquisition of Ledgers by Ravix Group. On May 11, announced sale of Trinity Warranty Solutions via management buy-out. Reiterating 2026 Financial Targets Delivering the two key pillars of value creation for Kingsway shareholders: organic and inorganic growth. ORGANIC GROWTH Double Digit Revenue and EBITDA INORGANIC GROWTH Target 3-5 High-Quality Acquisitions KINGSWAY FLYWHEEL Per-Share Value Accretion Double-Digit Organic Growth Kingsway is budgeting double-digit organic revenue and profit growth from both KSX and Extended Warranty. Kingsway Search Xcelerator Extended Warranty KSX Investments Paying Off Strong Cash Sales, Moderating Claims Growth Recurring revenues, capital-light, and with demand tailwinds Investments made in 2025 now poised to accelerate growth Sales momentum from H2 2025 carrying into 2026 Warranty claims growth is moderating in both frequency and severity Target 3-5 Acquisitions KSX now running parallel M&A programs of (1) de novo platforms and (2) tuck-in acquisitions. Inorganic Growth Engine Strong Underwriting Discipline Active OIR pipeline New platform creation Operator-led tuck ins 30%+ IRR hurdle Mid-single-digit EBITDA multiples Capital-light business Strong demand tailwinds Clear operational improvements Governance Change to Support Next Stage of Growth Adam Patinkin appointed Board Chairman, with Terry Kavanagh transitioning to Board Vice-Chairman Adam J. Patinkin Chairman of the Board Founder and Managing Partner of David Capital Partners, LLC, a long-term oriented alternative investment firm Kingsway Director since 2025 Playing an active role supporting Kingsway's management team to deliver the Company's strategic and financial ambitions Terence M. Kavanagh Vice-Chairman of the Board Chairman of Kingsway from 2012 to 2026 Guided Kingsway through strategic shift from legacy insurance holding company to Search Fund platform Continues tenure on the Board as Vice-Chairman, providing experience and expertise The Equity Story Search Has Compelling Long-Term Returns The Search Fund model - or "Entrepreneurship Through Acquisition" (ETA) - has an attractive historical track record. " " Since 1996 the Center for Entrepreneurial Studies at Stanford Graduate School of Business (GSB) has conducted a biennial study of core search funds, an entrepreneurial path undertaken by one or two individuals who form an investment vehicle with a small group of investors to search for, acquire, and lead a privately held company for the medium to long term, typically five to ten years. Through this research, Stanford seeks to provide insight into the factors that influence the outcomes of these entrepreneurship vehicles for first-time searcher-CEOs and their investors. This survey includes data from every known core search fund in the United States and Canada . +35.1 % Median historical return across all Search Funds tracked by the Stanford Graduate School of Business since 1984 Stanford GSB's research on Search Funds can be found at: https://www.gsb.stanford.edu/experience/about/centers-institutes/ces/research/search-funds Search Serves A Clear Market Purpose Search provides an exit to small business owners looking to retire, but who don't have a logical succession plan. Looking to Retire Post-MBA Seller No Succession Plan or Heir Requires Monetization Event No PE Interest Strategic Sale A Bad Outcome Talented and Motivated Provides a Financial Exit Provides a Succession Plan Preserves Founder's Legacy Buyer Search facilitates a win-win outcome for both seller and buyer. Why Search Outperforms "Lifestyle" Business Motivated Operator Founder-Led Sales Professional Sales Team "Pen & Paper" Technology & Systems Local Market Regional Expansion Cash Distributions Investing For Growth An energetic, talented, and incentivized operator often finds numerous paths to improve a "lifestyle" business. Building through Search Kingsway employs the traditional Search Fund model to acquire and grow a collection of high-quality services businesses. Kingsway seeks to acquire small businesses with EBITDA of $1-3M for roughly 4-6x EBITDA using a 50/50 split of equity and debt. The new operator then invests in the business to position it for growth. Kingsway provides support both during the business acquisition phase as well as post-close, including via implantation of the Kingsway Business System (KBS) for operational excellence. The "Silver Tsunami" Of Business Owner Retirements Has Arrived The next two decades will see record numbers of Baby Boomer business owners looking for an exit. Nearly $4.8 trillion of net worth, representing the largest intergenerational shift of wealth in US history , will be transferred over the next 20 years More than 2 million small businesses are expected to transition leadership over the next ten years. Lower middle market private equity buyers are hesitant to purchase businesses in which the primary operator seeks an exit from day-to-day operating responsibilities. Search Funds can help fill the gap - but with just a few hundred active searches at any time, the overwhelming number of small businesses for sale creates a favorable supply/demand dynamic for Search Fund buyers. It's not a "Silver Wave"…it's a "Silver Tsunami" Building through Search NYSE:KFS 20 Attention : This is an excerpt of the original content. To continue reading it, access the original document here .

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