Slide 1: Investor Q1 2026 Presentation
INVESTOR Q1 2026 PRESENTATION Speakers: McKeel Hagerty, Chief Executive Officer and Chairman Patrick McClymont, Chief Financial Officer
Slide 2: Forward Looking Statements / Non-GAAP Financial Measures
Forward Looking Statements / Non-GAAP Financial Measures This presentation contains statements that constitute “forward- manage risks associated with disruptions, interruptions, outages, marketing and advertising, digital services, accounting matters, looking statements” within the meaning of the fe
Slide 3: Q1 2026 Highlights
Q1 2026 Highlights Total Revenue1 of $312 million Completed strategic evolution to assume control of Markel program and 1. Written Premium growth of 18% to $289 million 100% of premium post transition to » Added a record 112,000 new members in the fronting arrangement first quarter and increased pol
Slide 4: 2026 Priorities
2026 Priorities Double policies in force to 3.0 million by 2030 INVESTING IN OUR MEMBER-CENTRIC APPROACH TO DELIVER COMPOUNDING PROFIT GROWTH: » Implement Markel Fronting Arrangement with 100% quota share and realize anticipated benefits » Accelerate insurance growth with State Farm rollout » Levera
Slide 5: First Quarter 2026 Financial Highlights
FIRST QUARTER 2026 Financial Highlights GROWTH PERSISTENCE PROFITABILITY $312M 38.4% $21M $13M HAGERTY RE TOTAL REVENUE 1 LOSS RATIO 2 LOSS BEFORE TAXES 1 NET LOSS -5% -164% -147% 86.6% HAGERTY RE COMBINED RATIO 3 $289M $85M $(0.06) 88.5% WRITTEN PREMIUM ADJUSTED EBITDA 4 BASIC EARNINGS (LOSS) PER S
Slide 6: Revenue Components
Revenue Components 18% Growth in Written Premium Fueled by 15% PIF Growth TOTAL REVENUE FIRST QUARTER 2026 HIGHLIGHTS Earned premium (+42%) Earned premium » Quota share increased to 100% effective January 1, 2026 under Commission and fee revenue1 the Markel Fronting Arrangement Membership + other re
Slide 7: First Quarter 2026 Earnings Analysis
First Quarter 2026 Earnings Analysis Delivering Sustained Underlying Profit Growth FIRST QUARTER NET INCOME 1 FIRST QUARTER ADJUSTED EBITDA 2 $85 $27 $48 $8 $36 $(13) YTDQ1 YTD Q12024 2024 YTD YTDQ1 Q12025 2025 YTD YTD Q1 2026 Q1 2026 YTD Q1 2024 YTD Q1 2024 YTD Q1 2025 YTD YTD YTD Q1 2025 Q1 2026 Q
Slide 8: 2026 Outlook
2026 Outlook Sustained Compounding Growth IN THOUSANDS 2025 RESULTS 2026 OUTLOOK ($) 2026 OUTLOOK (%) LOW END HIGH END LOW END HIGH END Total Written Premium $1,193,548 $1,373,000 $1,385,000 15% 16% Total Revenue 1 $1,456,389 $1,280,000 $1,300,000 (12)% (11)% Net Income (Loss) 2, 3 $149,225 $(51,000
Slide 9: Non-GAAP Financial Measures | 2026 Outlook
NON-GAAP FINANCIAL MEASURES | 2026 OUTLOOK Net Income (Loss) to Adjusted EBITDA IN THOUSANDS 2026 Low 2026 High Net Loss1 ($51,000) ($41,000) Interest expense and other, net2 5,000 5,000 Income tax expense 33,000 34,000 Depreciation and amortization 40,000 40,000 Share-based compensation expense 19,
Slide 10: Appendix
Appendix
Slide 11: Revenue Components by Quarter
REVENUE COMPONENTS BY QUARTER $ in Millions COMMISSION + FEE REVENUE 1 EARNED PREMIUM MEMBERSHIP, MARKETPLACE + OTHER REVENUE 143 240 137 129 116 193 187 106 178 166 168 169 100 158 89 152 89 56 50 48 48 48 42 34 31 27 16 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4
Slide 12: Non-GAAP Financial Measures: Adjusted EBITDA
NON-GAAP FINANCIAL MEASURES Adjusted EBITDA IN THOUSANDS Q1 2025 Q2 2025 - Q4 2025 Q1 2026 TTM Net income (loss) $27,293 $121,932 ($12,745) $109,187 Interest expense and other, net1 1,689 39,207 922 40,129 Income tax (benefit) expense 5,489 (15,532) (8,192) (23,724) Depreciation and amortization 9,4
Slide 13: Non-GAAP Financial Measures: Adjusted Net Income and Diluted EPS
NON-GAAP FINANCIAL MEASURES Adjusted Net Income (Loss) and Adjusted Diluted EPS THREE MONTHS ENDED MARCH 31, Adjusted Net Income and Adjusted Diluted EPS Series A Convertible Preferred Stock, we believe these measures facilitate 2026 2025 Adjusted Net Income (Loss) represents Net income (loss) attri
Slide 14: Markel Fronting Arrangement
Markel Fronting Arrangement Evolving the decade-long partnership, with Hagerty controlling 100% of the premium in 2026 PREVIOUS MODEL NEW FRONTING STRUCTURE (1/1/26) » Hagerty earned 42% total » Hagerty Re earns 100% of the commissions as an MGA and retained premium and retains 100% of the risk ~80%
Slide 15: Q1 2026 P&L Comparability Bridge
Q1 2026 P&L COMPARABILITY BRIDGE THREE MONTHS ENDED MARCH 31, 2026 Hagerty Re: Essentia Hagerty Re: Essentia Policy Year 2026 & Policy Year 20251 Other Carriers2 Hagerty Re Total MGA+4 Consolidation Entries5 Insurance Segment REVENUES: in thousands Earned premium, net $218,273 $21,369 $239,642 $— $—
Slide 16: Well-Positioned to Capture Additional Market Share
WELL-POSITIONED TO CAPTURE ADDITIONAL MARKET SHARE Consistent low to mid-teens premium growth with historically low volatility underwriting TYPE TOTAL ADDRESSABLE HAGERTY TARGET HAGERTY TCM HAGERTY PENETRATION AND U.S. AUTO INSURED VEHICLE COUNT MARKET (M) MARKET (M) PENETRATION Pre 1981 Vehicles 11
Slide 17: Hagerty's Differentiated Model Delivers High-Quality Growth
HAGERTY’S DIFFERENTIATED MODEL DELIVERS HIGH-QUALITY GROWTH Consistent low to mid-teens premium growth with low volatility underwriting HAGERTY U.S. AUTO PREMIUM GROWTH VS. INDUSTRY TOP 100 HAGERTY U.S. AUTO LOSS PERFORMANCE VS. INDUSTRY TOP 100 Hagerty U.S. Auto - CAGR 13% Hagerty Loss Ratio - aver
Slide 18: Historical Written Premium Growth
HISTORICAL WRITTEN PREMIUM GROWTH TOTAL U.S. AUTO WRITTEN PREMIUM U.S. AUTO WRITTEN PREMIUM ANNUAL GROWTH 1,200 20% 18% 1,000 15% 800 13% 600 10% 8% 400 5% 200 3% 0 —% 2012 2011 2010 2009 2008 2007 2006 2025 2024 2023 2022 2021 2020 2019 2018 2017 2016 2015 2014 2013 2009 2016 2023 2005 2012 2019 20
Slide 19: Written Premium Growth Fueled by New Members
WRITTEN PREMIUM GROWTH FUELED BY NEW MEMBERS Consistent share gains drive new business count 450,000 400,000 350,000 300,000 250,000 200,000 150,000 100,000 50,000 0 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 2024 2025 • New business count accelerated with commencement of State Farm Classic+
Slide 20: Hagerty: Never Stop Driving
HAGERTY lA NEVER STOP DRIVING