#1#2FORWARD LOOKING STATEMENTS / NON-GAAP FINANCIAL MEASURES This presentation contains statements that constitute forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. Forward- looking statements include all statements that are not historical facts. These forward- looking statements reflect our current expectations and projections with respect to our expected future business and financial performance, including, among other things: (i) expected operating results, such as revenue growth and financial position; (ii) changes in the market for our products and services; (iii) our plans to expand market share, including planned investments and partnerships; (iv) anticipated business objectives; and (v) the strength of our business model. These statements may be preceded by, followed by, or include the words "anticipate," "believe," "envision," "estimate," "expect," "forecast," "future," "goal," "intend," "likely," "outlook," "plan," "potential," "project,” “seek,” “target," "can," "could,” “may,” “should," "would," "will," the negatives thereof and other words and terms of similar meaning. A number of factors could cause actual results or outcomes to differ materially from those indicated by these forward-looking statements. These factors include, among other things, our ability to: (i) compete effectively within our industry and attract and retain members; (ii) maintain key strategic relationships with our insurance distribution and underwriting carrier partners; (iii) prevent, monitor and detect fraudulent activity; (iv) manage risks associated with disruptions, interruptions, outages or other issues with our technology platforms or our use of third-party services; (v) accelerate the adoption of our membership products as well as any new insurance programs and products we offer; (vi) manage the cyclical nature of the insurance business, including through any periods of recession, economic downturn or inflation; (vii) address unexpected increases in the frequency or severity of claims; (viii) comply with the numerous laws and regulations applicable to our business, including state, federal, and foreign laws relating to insurance and rate increases, privacy, the internet and accounting matters; (ix) manage risks associated with being a controlled company; and (x) successfully defend any litigation, government inquiries and investigation. The forward-looking statements herein represent our judgment as of the date of this release and we disclaim any intent or obligation to publicly update or review any forward-looking statement, whether as a result of new information, future developments, or otherwise. This presentation should be read in conjunction with the information included in our filings with the SEC and press releases. Understanding the information contained in these filings is important in order to fully understand our reported financial results and our business outlook for future periods. In addition, this presentation contains certain "non-GAAP financial measures". The non-GAAP measures are presented for supplemental informational purposes only. Reconciliations to the most directly comparable financial measure calculated and presented in accordance with GAAP are provided in the appendix to this presentation. HAGERTY Q2 2023 | 2#3SOL 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#4es univa correre 40 SO 866-5192 673 1993 LBZ-2532 AAX 1568 75AY7) ERC 585 MFK-15M 33 IX316 875 7149 PF JKH-851113436A 8YB-H25 25501613147 ALASKA 1795 46246P 8D27559 441-TXB 927-Y80 QU243 27T-SKV 1279-26P 672TV KWD519 86 3W14582 TERAS -1859 BNC9072 8CDF612 572 GOT A4F 968 869-YOL BAD 0986 341 9796 9-88908 C25-1707 88 151 09139 056 4092 JRM-4011 542 14 DFS-2953 HAGERTY MARKETPLACE Hagerty Marketplace is a top focus area in 2023 as we seek to provide an unmatched online and live Marketplace experience for consumers. >> Our Marketplace is positioned as the trusted brand for auto enthusiasts, offering certification services, title and escrow, financing options and other high-value services that differentiate our product from competitors. >> Large and growing market opportunity with ~300,000 cars transacting for ~$12.5 billion through Hagerty's insurance book during 2022. >> Direct revenue from live auctions, private sales, online marketplace as well as financing options Other material opportunities include insurance sales and Hagerty Driver's Club (HDC) memberships >> Proven leadership team with strong cultural fit HAGERTY Q2 2023 | 4#5#6#7#8#9#10#11#12#13#14#15#16#17#18