Slide 1: Investor Presentation Q2 2026
INVESTOR PRESENTATION Q2 2026 Speakers: McKeel Hagerty, Chief Executive Officer and Chairman Patrick McClymont, Chief Financial Officer
Slide 2: Forward Looking Statements / Non-GAAP Financial Measures
HAGERTY Q2 2026 | 2 Forward Looking Statements / Non-GAAP Financial Measures This presentation contains statements that constitute “forward- looking statements” within the meaning of the federal securities laws. All statements we provide, other than statements of historical fact, are forward-looking
Slide 3: Second Quarter YTD 2026 Highlights
HAGERTY Q2 2026 | 3 SECOND QUARTER YTD 2026 Highlights 1 YTD Q2 2026 reflects the transition of business under the Markel Fronting Arrangement, which resulted in a decrease in Commission and fee revenue and the recognition of transitional costs to amortize the remaining deferred ceding commissions r
Slide 4: 2026 Priorities
Grow 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 » Leverage technology to e
Slide 5: Second Quarter YTD 2026 Financial Highlights
HAGERTY Q2 2026 | 5 SECOND QUARTER YTD 2026 Financial Highlights 1 YTD Q2 2026 reflects the transition of business under the Markel Fronting Arrangement, which resulted in a decrease in Commission and fee revenue and the recognition of transitional costs to amortize the remaining deferred ceding com
Slide 6: Revenue Components
HAGERTY Q2 2026 | 6 Revenue Components 19% Growth in Written Premium Fueled by PIF Growth 1 Includes base commissions, payment plan fees and contingent underwriting commissions. 2026 now reflects the transition of our business under the Markel Fronting Arrangement, which resulted in a decrease in Co
Slide 7: Second Quarter Earnings Analysis
HAGERTY Q2 2026 | 7 Q2 2024 Q2 2025 Q2 2026Q2 2024 Q2 2025 Q2 2026 1 Q2 2024 Net Income includes a $2 million loss as a result of a change in the fair value of our warrant liabilities. Q2 2026 Net Income includes $64 million of pre-tax transitional costs associated with the new Markel Fronting Arran
Slide 8: Second Quarter YTD 2026 Earnings Analysis
HAGERTY Q2 2026 | 8 Q2 2024 Q2 2025 Q2 2026 Q2 2024 Q2 2025 Q2 2026 1 YTD Q2 2024 Net Income includes an $8 million loss as a result of a change in the fair value of our warrant liabilities. YTD Q2 2026 Net Loss includes $153 million of pre-tax transitional costs associated with the new Markel Front
Slide 9: Increased 2026 Outlook
HAGERTY Q2 2026 | 9 Increased 2026 Outlook 1 Prior 2026 Outlook shared on the Company’s first quarter earnings call on May 6th, 2026. 2 Revenue guidance reflects the accounting impact of the Markel Fronting Arrangement. Beginning in 2026, we now control the Essentia book of business with the benefit
Slide 10: Non-GAAP Financial Measures | 2026 Outlook
HAGERTY Q2 2026 | 10 NON-GAAP FINANCIAL MEASURES | 2026 OUTLOOK Net Income to Adjusted EBITDA IN THOUSANDS 2026 Low 2026 High Net Income $18,000 $30,000 Interest expense and other, net1 5,000 5,000 Income tax benefit (11,000) (13,000) Depreciation and amortization 40,000 40,000 Share-based compensat
Slide 11: Appendix
Appendix
Slide 12: Revenue Components by Quarter
HAGERTY Q2 2026 | 12 REVENUE COMPONENTS BY QUARTER $ in Millions 152 158 166 168 169 178 187 193 240 252 Q1 2024 Q2 2024 Q3 2024 Q4 2024 Q1 2025 Q2 2025 Q3 2025 Q4 2025 Q1 2026 Q2 2026 89 129 116 89 100 143 137 106 16 24 Q1 2024 Q2 2024 Q3 2024 Q4 2024 Q1 2025 Q2 2025 Q3 2025 Q4 2025 Q1 2026 Q2 2026
Slide 13: Net Income to Adjusted EBITDA Reconciliation
HAGERTY Q2 2026 | 13 IN THOUSANDS Q2 2025 Q3 2025 - Q1 2026 Q2 2026 TTM Net income $47,202 $61,985 $8,041 $70,026 Interest expense and other, net1 4,946 35,183 28 35,211 Income tax expense (benefit) 6,161 (29,885) (5,809) (35,694) Depreciation and amortization 8,833 28,909 9,716 38,625 EBITDA 67,142
Slide 14: Non-GAAP Reconciliation Footnotes
HAGERTY Q2 2026 | 14 1 For the three and six months ended June 30, 2026, other unusual items includes professional fees related to the pending acquisition of Bennetts and additional severance expenses associated with the actions taken in the fourth quarter of 2025.For the three and six months ended
Slide 15: Markel Fronting Arrangement
Markel Fronting Arrangement Evolving the decade-long partnership, with Hagerty controlling 100% of the premium in 2026 HAGERTY Q2 2026 | 15 → Somewhere between a race car and a work of art sits the 1956 Arnolt-Bristol — shown here at The Greenwich Concours d’Elegance. PHOTOGRAPHER: ANDREW SNUCINS DR
Slide 16: Second Quarter P&L Comparability Bridge
HAGERTY Q2 2026 | 16 SECOND QUARTER P&L COMPARABILITY BRIDGE a Represents Hagerty Re’s earned premium and associated policy acquisition costs related to Essentia policies issued in 2025. b Represents Hagerty Re’s earned premium and associated policy acquisition costs related to Essentia policies iss
Slide 17: Second Quarter YTD P&L Comparability Bridge
HAGERTY Q2 2026 | 17 SECOND QUARTER YTD P&L COMPARABILITY BRIDGE a Represents Hagerty Re’s earned premium and associated policy acquisition costs related to Essentia policies issued in 2025. b Represents Hagerty Re’s earned premium and associated policy acquisition costs related to Essentia policies
Slide 18: Well-Positioned to Capture Additional Market Share
HAGERTY Q2 2026 | 18 WELL-POSITIONED TO CAPTURE ADDITIONAL MARKET SHARE Large and underpenetrated target market Hagerty Target Market is the subset of TAM identified as more likely to be currently used as collector vehicles based on age, inherent vehicle characteristics and expert curation. Source:
Slide 19: Hagerty's Differentiated Model Delivers High-Quality Growth
HAGERTY Q2 2026 | 19 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 2024 2025 —% 100% 200% 300% 400% 500% 600% Hagerty U.S. Auto - CAGR 13% Industry Top 100 - CAGR 5% Hagerty Loss Ratio - average = 39% Industry Loss Ratio - average = 68% HAGERTY U.S. AUTO PREMIUM GROWTH VS. IN
Slide 20: Historical Written Premium Growth
HAGERTY Q2 2026 | 20 HISTORICAL WRITTEN PREMIUM GROWTH 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 2024 2025 0 200 400 600 800 1,000 1,200 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 2024 2025 —% 3% 5% 8
Slide 21: Written Premium Growth Fueled by New Members
HAGERTY Q2 2026 | 21 450,000 400,000 350,000 300,000 250,000 200,000 150,000 100,000 50,000 0 2025 2024 2023 2022 2021 2020 2019 2018 2017 2016 2015 2014 • New business count accelerated with commencement of State Farm Classic+ conversion WRITTEN PREMIUM GROWTH FUELED BY NEW MEMBERS Consistent share
Slide 22: Never Stop Driving
HAGERTY B NEVER STOP DRIVING