Hagerty Investor Presentation Deck

SOL YTD Q2 2023 HIGHLIGHTS Total Revenue growth of 28% Written Premium growth of 17% Improved Profitability >> Net Income of $1 million compared to $10 million in the prior year period >>> Adjusted EBITDA of $41 million compared to $10 million in the prior year period >> Raised $105 million in capital on June 23, 2023 >> $80 million in convertible preferred equity and a $25 million commitment for Hagerty Re Limited INCREASED 2023 OUTLOOK Pivot to significantly improved profitability fueled by top- line momentum, cost containment & efficiency measures >> Total Revenue growth of 23-27% » Written Premium growth of 13-15% >> Net Income (Loss) of $(12)-8 million Adjusted EBITDA (¹) of $60-80 million The Company's outlook on the May 9, 2023 first quarter earnings call was for Total Revenue growth of 22-26%, Written Premium growth of 11-13%, Net Income of $(13)-7 million and Adjusted EBITDA of $55-75 million ¹ See Appendix for additional information regarding this non-GAAP financial measure. HAGERTY Q2 2023 | 3

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