Kingsway Corporation · NYSE:KWY
Kingsway — Investor Day (May 2026)
68 slides from Kingsway's investor day presentation, May 18, 2026
Slide 1: Investor Day: Building through Search
NYSE: KFS Investor Day May 18, 2026 Building through Search
Slide 2: Forward-Looking Statements
Forward-Looking Statements This presentation includes "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
Slide 3: Agenda
The Last 12 Months at Kingsway Agenda 2026 Outlook The Equity Story Capital Markets Update Theory to Action: KBS Deployment Operator Spotlight: Miles Mamon Operator Spotlight: Davide Zanchi Q&A Building through Search Fireside Chat
Slide 4: About Us
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, profi
Slide 5: Kingsway Investor Days: Three-Year Narrative Arc
Kingsway Investor Days: Three-Year Narrative Arc From “Vision” to “System” to “Proof”. Vision System Proof 2024 2025 Today A repeatable model to An operating system to Tangible evidence compound intrinsic turn good acquisitions Kingsway’s vision is value per share. into great businesses. becoming a
Slide 6: The Last 12 Months at Kingsway
The Last 12 Months at Kingsway
Slide 7: 2025 Scorecard
2025 Scorecard Kingsway delivered on the targets we set out last year. What We Said What We Did Completed 6 acquisitions in 2025 Target 3-5 high-quality ACQUISITIONS including Bud’s Plumbing, ViewPoint, acquisitions per year Roundhouse, AAA, The HR Team, and Southside Plumbing Run-rate adjusted Achi
Slide 8: Kingsway Acquired Six High-Quality B2B and B2C Services Businesses
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 Building through Search NYSE:KFS 8
Slide 9: KSX is Majority of Revenue and EBITDA for First Time
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
Slide 10: 2026 Outlook
2 2026 Outlook
Slide 11: Strong Start to 2026
Strong Start to 2026 Operating performance is ahead of internal expectations, while continuing to execute disciplined M&A. Kingsway delivered a KSX achieved record Reiterated expectations for On January 7, announced strong first quarter of 2026, quarterly revenue and double-digit organic growth acqu
Slide 12: Reiterating 2026 Financial Targets
Reiterating 2026 Financial Targets Delivering the two key pillars of value creation for Kingsway shareholders: organic and inorganic growth. ORGANIC GROWTH INORGANIC GROWTH KINGSWAY FLYWHEEL Double Digit Target 3-5 Per-Share Revenue and High-Quality Value EBITDA Acquisitions Accretion Building throu
Slide 13: Double-Digit Organic Growth
Double-Digit Organic Growth Kingsway is budgeting double-digit organic revenue and profit growth from both KSX and Extended Warranty. Kingsway Search Extended Xcelerator Warranty KSX Investments Paying Off Strong Cash Sales, Moderating Claims Growth Recurring revenues, capital-light, Sales momentum
Slide 14: Target 3-5 Acquisitions
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 30%+ IRR hurdle Mid-single-digit EBITDA multiples Capital-light business Strong demand tailwinds Active OIR New platform
Slide 15: Governance Change to Support Next Stage of Growth
Governance Change to Support Next Stage of Growth Adam Patinkin appointed Board Chairman, with Terry Kavanagh transitioning to Board Vice-Chairman Adam J. Patinkin Terence M. Kavanagh Chairman of the Board Vice-Chairman of the Board Founder and Managing Partner of David Chairman of Kingsway from
Slide 16: The Equity Story
3 The Equity Story
Slide 17: Search Has Compelling Long-Term Returns
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
Slide 18: Search Serves A Clear Market Purpose
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 No Succession Plan or Heir Talented and Motivated Seller Requires Monetization Event Provides a Financial Exit Buyer No PE
Slide 19: Why Search Outperforms
Why Search Outperforms An energetic, talented, and incentivized operator often finds numerous paths to improve a “lifestyle” business. “Lifestyle” Business Motivated Operator Building through Search Founder-Led Sales Professional Sales Team Kingsway employs the traditional Search Fund model to acqui
Slide 20: The "Silver Tsunami" Of Business Owner Retirements Has Arrived
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 More than 2 million small Lower middle market Search Funds can help fill worth, representing the businesses are
Slide 21: Search Is Difficult To Access
Search Is Difficult To Access Kingsway offers a unique vehicle to participate in the Search Fund asset class via an NYSE-listed company. Private Fund of Funds or DIY Search Fund Investing Search Accelerators Building through Search Most Search Fund investing is An alternative approach is to As a pub
Slide 22: Kingsway's Advantages
Kingsway’s Advantages Kingsway is well-positioned for success with permanent capital and years of investment in its Search infrastructure. Strong Track Infrastructure Disciplined Record and Support Investment Criteria Top Quality World-Class Public Company Searcher Talent Advisory Board Reputation P
Slide 23: Top Quality Searcher Talent
Top Quality Searcher Talent In 2025, Kingsway had hundreds of applicants for three open OIR positions. Davide Zanchi Timi Okah IS Technology Ravix Platform Paul Vidal Operator-in-Residence Portfolio Operators In CEO’s Residence Charles Mokuolu Colter Hanson SNS, Inc. Skilled Trades Platform To be An
Slide 24: Disciplined Investment Criteria
Disciplined Investment Criteria Kingsway seeks to acquire high-quality B2B and B2C services businesses with consistent characteristics. High percentage Capital light & Operating in a of recurring non-cyclical fragmented revenue business industry B2B or B2C Long history of Low customer Growth busines
Slide 25: A World-Class Advisory Board
A World-Class Advisory Board Kingsway’s Operators-In-Residence and Business CEO’s have access to an exceptional team of advisors. BOARD PROFILES Tom Joyce Will Thorndike Tyler Gordy Mr. Tom Joyce served as CEO of Mr. Will Thorndike is widely known as Mr. Tyler Gordy is a Partner at Artesian, a Danah
Slide 26: A Tax-Advantaged Corporate Structure
A Tax-Advantaged Corporate Structure Kingsway has $628m of valuable NOL tax assets. Kingsway’s tax assets stem from a legacy insurance business exited a decade ago. $385m Kingsway’s NOL’s relate to a truck insurance business that suffered during the 2008 financial crisis. $92m Kingsway began its piv
Slide 27: Kingsway's Strategy: A Self-Funding Flywheel
Kingsway’s Strategy: A Self-Funding Flywheel Cash flows from Kingsway’s portfolio of asset-light businesses can fund further acquisitions and growth. Invest To Grow Acquire Great Businesses 2 1 Typical Organic Growth Path Post-Transaction Investment period to position the business for growth Kingswa
Slide 28: A Promising Track Record
A Promising Track Record Kingsway’s experience with Search provides confidence the model is working. PWSC Kingsway’s proof-of-concept with the Search Fund model was the acquisition of a new home warranty business called PWSC. PWSC was acquired for $10m, funded 50% with preferred equity. Tyler Gordy,
Slide 29: Conclusion
Conclusion Kingsway is the only publicly-traded US company employing the Search Fund model to acquire and build great businesses. Strong Track Infrastructure Disciplined Record and Support Investment Criteria Portfolio of High- Quality Services Companies Top Quality World-Class Public Company Search
Slide 30: Capital Markets Update
4. Capital Markets Update
Slide 31: Capital Markets Upgrades
Capital Markets Upgrades A comprehensive refresh of Kingsway’s capital markets presence is underway. Framework Workstreams A rebrand that accurately reflects our strategic direction Branding Name Change Ticker Change Brand Refresh New Website A new website that addresses Kingsway’s key stakeholders
Slide 32: Kingsway Corporation
Kingsway Corporation Following shareholder approval this morning, Kingsway will rebrand tomorrow as Kingsway Corporation with ticker KWY. Notes Name and ticker change approved by Old New shareholders at 2026 AGM. ‘Financial Services’ is a branding relic of the Kingsway Kingsway legacy insurance hold
Slide 33: New Brand Identity and Kingsway Website
New Brand Identity and Kingsway Website To be launched in summer 2026. Unified Kingsway Revised Refreshed New Brand New Website Clear Audience Brand Logomark Color Scheme Typography Guidelines and Domain Messaging Segmentation Shareholders Entrepreneurs Business Owners Intermediaries Dedicated Inves
Slide 34: Simplified Face Financial Statements
Simplified Face Financial Statements New income statement and balance sheet presentations are more reflective of Kingsway’s focus on the KSX model. Old Income Statement Structure New Income Statement Structure 20X5 20X4 20X6 20X5 Service fee and commission revenue Revenues Claims authorized on vehic
Slide 35: Standardized Data Aggregator Descriptions
Standardized Data Aggregator Descriptions A ‘single source of truth’ for data aggregators to make Kingsway more accessible to the investment community. Today Planned Planned Submissions to Aggregators Disparate and incorrect information is Name change is an opportunity to causing confusion for inves
Slide 36: Enhanced Investor Reporting
Enhanced Investor Reporting Intention to begin reporting organic growth metrics once Kingsway’s comps set is meaningful. Planned Investor Reporting Short-to-Mid Term: Consolidated Basis Organic Revenue Growth Organic EBITDA Growth Centralized Accounting Mid-to-Long Term: Segmented, Subject to Scale
Slide 37: Theory to Action: KBS Deployment
Theory to Action: KBS Deployment
Slide 38: Improving the Probability of Search Success
Improving the Probability of Search Success Kingsway seeks to “bend the curve” towards better KSX outcomes by proactively addressing potential points of failure. Pre-Deal Factors Post-Deal Factors Customer Poor Industry Highly Levered Concentration Growth Balance Sheet Just as we have a playbook for
Slide 39: The Kingsway Business System (KBS)
The Kingsway Business System (KBS) KBS is a comprehensive, integrated approach to continuous improvement inspired by best practices at firms like Danaher. Talent Hiring and promoting the best people available at every salary level is what distinguishes premier companies from mediocre firms. Plan Cre
Slide 40: Kingsway Supports Operator CEOs at Every Stage
Kingsway Supports Operator CEOs at Every Stage KBS provides practical tools and frameworks to drive real-world results. Centralized Leadership Training KSX Community Knowledge Hub Establishing Priorities Proprietary to Kingsway Peer Feedback Building Culture Tools, Case Studies, etc. Coa
Slide 41: The Operator Journey: Crawl, Walk, Run
The Operator Journey: Crawl, Walk, Run KBS helps sequence what OIRs install, in what order, and at a pace the organization can sustain. Entry and Diagnosis The KBS Four-Stage Deployment Sequence Install Operating System Go Deeper and Strategic Development Breakthrough Execution Start CRAWL 1 Year WA
Slide 42: Operator Spotlight: Miles Mamon
Operator Spotlight: Miles Mamon
Slide 43: Operator Bio
Operator Bio Miles Mamon is the CEO of Roundhouse Electric & Equipment Co., Inc. United States Army Air Defense Artillery Officer forward deployed to the Middle East. In 2019, graduated with a JD/MBA from Northwestern University. Promoted to VP in Merchant Banking division. Building through Search N
Slide 44: Why Kingsway
Why Kingsway KSX is an attractive home to pursue the Search Fund model. Pivot to Search KSX Benefits Interested in Search Fund model at Kellogg; a desire to 1 2 3 strengthen business and Deep Search Alignment on Ready-to-Go financial acumen first Experience Investing / Operating Platform Decision po
Slide 45: Roundhouse Electric
Roundhouse Electric Roundhouse provides electric motor maintenance, repair, testing, and sales services to natural gas infrastructure companies. Transaction Details Mission-Critical Services Business With Secular Tailwinds Date Jul ‘25 Location Odessa, TX Financial Profile Customers & Culture Secula
Slide 46: Kingsway's Tangible Impact
Kingsway’s Tangible Impact Four case studies highlight how the “theory” of Kingsway translates to positive real-world outcomes. Pre-Deal No “J-Curve” Framework To Scale Talent Deal Support Building Credibility Installing Infrastructure Hiring and Retaining Kingsway’s deal team provided Without Derai
Slide 47: #1: Deal Support
#1: Deal Support Kingsway provided significant resources to steward a complex deal over the finish line. How Kingsway Supported Roundhouse Acquisition Challenge A nuanced transaction with multiple owners and a sale-leaseback agreement Committed Deal Team Highly Nimble Single Decision Point Problem-S
Slide 48: KBS Stage 1: The First 100 Days
KBS Stage 1: The First 100 Days Many new business owners have an urge to immediately “fix everything”…but KBS sets out an entirely different approach. “The first 100 days are about learning, not changing. It’s a time to engage, listen, and learn – not to fix.” “The core belief is that your initial m
Slide 49: #2: No "J-Curve"
#2: No “J-Curve” Roundhouse has continued to consistently grow revenues and adjusted EBITDA at 20%+ year-over-year. Earning the “Right to Lead” at Roundhouse Challenge Building trust and credibility in a 50-year- old family business as an outsider Genuine partnership with Maintain strong No turnover
Slide 50: #3: Framework To Scale
#3: Framework To Scale Roundhouse revenue grew from $2m to $20m – but going from $20m to $100m requires different, more scalable systems. Building the Right Foundation at Roundhouse Challenge Identified and Implemented ERP Implemented KPI Preserving the features filled talent gaps system upgrades sc
Slide 51: #4: Talent
#4: Talent “Debottlenecking” Roundhouse’s capacity to serve its customers is key to maintaining and accelerating growth. Building a Repeatable Hiring, Training, and Retention Process Challenge Demand has outstripped Roundhouse’s service capacity for years Implemented in- Engaged 3rd-party Prioritize
Slide 52: Conclusion
Conclusion Kingsway and KBS have provided a clear framework for business improvement, with tangible results at Roundhouse. 1. Business Entry and Diagnosis 2. Install Operating System 3. Earned Trust With Stakeholders Drafting One-Page Plan Built credibility by following-through promises Vision, crit
Slide 53: Operator Spotlight: Davide Zanchi
Operator Spotlight: Davide Zanchi
Slide 54: Operator Bio
Operator Bio Davide Zanchi is the CEO of IS Technology. MBA at Stanford & PhD in Neuroscience. Background in pharma and biotech/healthcare with successful management experience. Leveraged background and network to purchase and operate a technology-focused business. Building through Search NYSE:KFS 5
Slide 55: Why Kingsway
Why Kingsway KSX is an attractive home to pursue the Search Fund model. Pivot to Search KSX Benefits Combines two passions: (1) investing and (2) operating; 1 2 3 the Search Fund model offers Public Company Public Company Built-In Support a path to both acquire and lead a business Structure Reputati
Slide 56: IS Technology
IS Technology The largest IT Managed Services business in Western North Carolina. Transaction Details Attractive Business With Significant Potential Date Sep ‘24 Location Fletcher, NC Financial Profile Customer Loyalty Internal Improvements M&A Potential Deal Price $19.5m Growth business Triple-
Slide 57: A Hurricane…and Three Business Challenges
A Hurricane…and Three Business Challenges On first day as CEO, a once-in-a-century hurricane devastated Western North Carolina. Force Majeure Sales Talent Technology Systems Hurricane Helene Hiring the Right Installing Appropriate Design Data-Driven In triage mode to support Salespeople to Drive Sys
Slide 58: IS Technology Helped the Community Recover
IS Technology Helped the Community Recover Immediately went into crisis management mode to make sure employees and customers were supported post-Hurricane. Office became a safe space Proactive outreach to for employees and loved ones customers for tech needs Negotiated extended Contacted local chamb
Slide 59: #1: Sales Talent
#1: Sales Talent Built a full customer retention and expansion engine – and for first time now have an outbound sales team. Actions Taken to Resolve Bottleneck Challenge Sales team had one account manager for Territory Mapping KBS Talent Identification Contacted OIRs 450 accounts, with Divided IST’s
Slide 60: #2: Technology
#2: Technology By following the KBS framework, a money-losing segment flipped to meaningful profitability. Actions Taken to Resolve Bottleneck Challenge Managed print services should be a KBS Diagnosis Framework Fixed MSP IT Root Issue Tech-Driven Processes high-margin recurring Identified process e
Slide 61: #3: Systems
#3: Systems IS Technology was largely operated with “pen and paper”; implementation of systems provided a foundation to scale. Actions Taken to Resolve Bottleneck Challenge IS Technology needed to move from a “pen Implemented Systems Upgrades and paper” operation Optimizing core workflows beyond to
Slide 62: Conclusion
Conclusion Kingsway and KBS have provided a clear framework for business improvement, with tangible results at IS Technology. 1. Entry & Diagnosis + 2. Install Op System 3. Go Deeper and Strategic Development 4. Breakthrough Execution Earned Trust With Stakeholders Develop Strategic Vision Connected
Slide 63: Q&A
Q&A
Slide 64: Fireside Chat
7 Fireside Chat
Slide 65: Appendix
Appendix
Slide 66: 12-Month Run-Rate Adjusted EBITDA Definition
12-Month Run-Rate Adjusted EBITDA Definition This metric is not intended to be guidance by management regarding the future earnings of the Company; rather, it is intended to capture the twelve-month earnings of what the Company currently owns or has recently acquired; as such, it includes: The a
Slide 67: Portfolio LTM EBITDA Definition
Portfolio LTM EBITDA Definition Portfolio LTM EBITDA represents management’s estimate of the trailing twelve-month adjusted EBITDA generated by the Company’s portfolio of operating businesses, including the KSX segment and the Extended Warranty segment. For the KSX segment, Portfolio LTM EBITDA
Slide 68: Building through Search
Building through Search Kent Hansen James Carbonara kingsway-financial.com Chief Financial Officer Partner, Hayden IR (312) 766-2163 (646) 755-7412 khansen@kingsway-financial.com james@haydenir.com