#120238 Investor Presentation Speakers: McKeel Hagerty | Chief Executive Officer Patrick McClymont | Chief Financial Officer HAGERTY ice 55 berlinetta#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 Q3 2023 | 2#3TRANSPORT YTD Q3 2023 HIGHLIGHTS Total Revenue growth of 28% Written Premium growth of 16% Added over 200,000 new customers Launched State Farm partnership in four states » Received financial strength rating of A- (Excellent) from AM Best Marketplace revenue of $25 million, growth of 210% Significantly improved profitability Net Income¹ of $19 million compared to $35 million Adjusted EBITDA² of $78 million compared to $0 million INCREASED 2023 OUTLOOK Deliver sustained top-line momentum in 2023 with significantly improved profitability IN THOUSANDS Total Revenue³ Total Written Premium³ Net Income Adjusted EBITDA² REVISED OUTLOOK $992,000-$1,00,000 $893,000-$901,000 $2,000-$12,000 $75,000-$85,000 PRIOR OUTLOOK $968,000-$1,000,000 $878,000-$894,000 ($12,000)-$8,000 $60,000-$80,000 ¹ Net Income in the prior year period included a $35 million revaluation gain and a $38 million change in fair value of warrant liabilities. 2 See Appendix for additional information regarding this non-GAAP financial measure. 3 Total revenue growth of 26-27% and Total Written Premium growth of 15-16% expected in 2023. HAGERTY Q3 2023 | 3#4Jest Stop Never Driving HAGERTY HAGERTY MARKETPLACE Hagerty Marketplace was created to help consumers buy and sell enthusiast vehicles. Large and growing market opportunity with ~300,000 cars transacting for ~$12.5 billion through Hagerty's insurance book during 2022. >> We seek to provide an unmatched online and live Marketplace experience for consumers by serving 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. >> Other material opportunities include insurance sales and Hagerty Driver's Club (HDC) memberships. >> Proven leadership team with strong cultural fit. >> During the first nine months of 2023, Marketplace delivered $24.9 million in revenue from live auctions, private sales, online marketplace as well as financing. HAGERTY Q3 2023 | 4#5HAGERTY + STATE FARM PARTNERSHIP >> Began activating State Farm agents to offer State Farm Classic+ policies and Hagerty Drivers Club in four initial states in September of 2023 >> 480,000+ existing collector car policies plus up to 75% HDC enrollment possible on new insurance policies sold by State Farm's ~19,500 agents >> Anticipated average annual revenue per customer: $85-$110 >> State Farm aligned in the success of the 10-year commercial partnership with an initial $500 million investment in Hagerty in 2021 as well as an additional $50 million investment in June of 2023 and $25 million long-term financing for Hagerty Re State Farm HAGERTY. HAGERTY Q3 2023 | 5#62023 PRIORITIES Deliver sustained top-line momentum in 2023 with significantly improved profitability On track to deliver Total Revenue growth of 26-27% powered by Written Premium growth of 15-16% >> Sustain double-digit Written Premium growth trajectory » Deliver an unmatched online and live Marketplace experience >> Drive loyalty, referrals and incremental revenue and profit from Membership Continued evolution into an integrated insurance business Increase Hagerty Re's quota share reinsurance agreement in the U.S. and U.K. to ~80% Significantly improving profitability ($75 million to $85 million in Adjusted EBITDA¹) through operational efficiencies and cost containment measures ¹ See Appendix for additional information regarding this non-GAAP measure. HAGERTY Q3 2023 SO#7GROWTH $755M Total Revenue +28% YTD Q3 2023 FINANCIAL HIGHLIGHTS $714M Written Premium +16% ¹ See Appendix for additional information regarding this non-GAAP measure. PERSISTENCE 41.5% Loss Ratio 88.2% Retention PROFITABILITY $17M Operating Income $78M Adjusted EBITDA¹ $19M Net Income $0.04 Basic Earnings Per Share HAGERTY Q3 2023 | 7#8Millions Commission + fee revenue¹ Membership, marketplace + other revenue Earned premium in Hagerty Re GROWTH 27% $216 $85 $24 Q3 $107 Q3 2022 $276 $103 $33 Total Revenue $140 Q3 2023 Growth 21% 37% 30% $590 $243 GROWTH 28% $56 REVENUE COMPONENTS $291 YTD $755 $288 $83 $384 YTD Q3 2022 YTD Q3 2023 Growth 18% 47% 32% ¹ Includes base commissions, payment plan fees and contingent underwriting commissions. 2 Currently applies to U.S. and U.K. programs. Generally described as an arrangement where underwriting risk and profit is shared proportionately. YTD Q3 2023 Highlights Commission + fee revenue (+18%) >> Written premium growth of 16% >> Policies in Force retention of 88% Membership, marketplace + other revenue (+47%) Membership revenue growth of 20% Marketplace revenue growth of 210% >> 80% of new insurance customers joined Hagerty Drivers Club (HDC) Earned premium in Hagerty Re (+32%) >> Contractual quota share² increased to ~80% in 2023 HAGERTY Q3 2023 | 8#9Millions Net Income 2023 2022 $24 $19 Q3 $35 $19 YTD Adjusted EBITDA $(10) $37 EARNINGS ANALYSIS Q3 $0 $78 YTD Adjusted EBITDA Q3 2023 $18,623 (6,260) 4,604 10,753 473 (850) 4,935 4,112 IN THOUSANDS Net income Interest and other (income) expense Income tax (benefit) expense Depreciation and amortization Restructuring, impairment and related charges, net Change in fair value of warrant liabilities Share-based compensation expense Losses and impairments related to divestitures Revaluation gain previously held equity method investment Other unusual items¹ Adjusted EBITDA² Q3 2022 YTD 2023 $24,313 $19,137 (662) (15,677) (91) 12,002 8,890 34,893 8,857 1,419 3,858 12,869 4,112 (11,583) (34,735) 837 987 $37,377 $(10,010) $78,449 2 See Appendix for additional information regarding this non-GAAP financial measure. YTD 2022 $34,636 375 4,077 24,337 (37,869) 8,165 (34,735) 1,110 $96 ¹ Other unusual items primarily includes a net legal settlement accrual recognized in the three and nine months ended September 30, 2023 and non-restructuring severance expense recognized in the nine months ended September 30, 2022. HAGERTY Q3 2023 | 9#102023 OUTLOOK: GROWTH AND PROFITABILITY Strong top-line momentum continuing in 2023 with significantly improved profitability IN THOUSANDS Total Revenue¹ Total Written Premium¹ Net Income Adjusted EBITDA² Low End Range $992,000 $893,000 $2,000 $75,000 2023 Outlook ¹ Total revenue growth of 26-27% and Total Written Premium growth of 15-16% expected in 2023. 2 See Appendix for additional information regarding this non-GAAP financial measure. High End Range $1,000,000 $901,000 $12,000 $85,000 Prior Outlook at Q2 2023 Low End Range $968,000 $878,000 $(12,000) $60,000 High End Range $1,000,000 $894,000 $8,000 $80,000 HAGERTY Q3 2023 | 10#11APPENDIX#12MILLIONS 250 200 150 100 50 $ IN THOUSANDS Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 2018 2019 2020 2021 2022 2018 2019 2020 2021 2022 5 Year Average Total Written Premium % Total Written Premium Q1 82,514 96,732 112,421 133,707 154,790 20% Q2 HISTORICAL SEASONALITY TRENDS 137,943 158,501 184,423 208,091 237,697 31% Q3 123,385 142,030 163,520 192,091 222,136 29% Q4 86,621 99,747 117,870 140,417 162,041 20% Total 430,463 497,010 578,234 674,306 776,664 100% THOUSANDS 90 80 70 60 50 40 30 20 10 New Business Count (Insurance) Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 2018 2019 2020 2021 2022 2018 2019 2020 2021 2022 5 Year Average New Business Count % Q1 32,610 36,848 41,510 51,799 47,514 19% Q2 56,729 62,842 70,622 77,013 74,922 32% Q3 51,795 57,426 73,619 68,077 68,561 29% North American footprint creates seasonal differences by quarter for written premium and new business count Q4 35,356 37,585 50,914 47,589 43,523 20% Total 176,490 194,701 236,665 244,478 234,520 100% HAGERTY Q3 2023 | 12#13Paid Membership Counts U.S. Insurance Member Insurance + HDC HDC Standalone Total U.S. Paid Member Count Canada Insurance Member Insurance + HDC HDC Standalone Total Canada Paid Member Count Total Insurance Member Insurance + HDC HDC Standalone Total HDC Paid Member Count Total Paid Member Count Q3 2022 462,289 660,304 29,769 1,152,362 82,728 58,085 1,582 142,395 545,017 718,389 31,351 749,740 1,294,757 Q3 2023 480,616 709,468 33,237 1,223,321 84,713 63,153 974 148,840 565,329 772,621 34,211 806,832 1,372,161 HAGERTY MEMBERSHIP Total Member Count 1.4 million Paid Members (+6%) Paid Member Count Individuals who have an in-force insurance policy or HDC membership as of a specified point in time. HDC Paid Member Count HDC standalone plus insurance + HDC. A customer with an active/in-force paying HDC membership that has full access to HDC benefits as of a specified point in time. 8% growth 6% growth Guest User Counts U.S. Canada Total Guest User Count Q3 2022 1,183,201 79,271 1,262,472 Q3 2023 1,305,743 85,892 1,391,635 Guest Member An individual who has created an on-line profile by providing email, establishing a password, and verifying email. HAGERTY Q3 2023 | 13#14RECONCILIATION OF NON-GAAP METRICS Net Income to Adjusted EBITDA IN THOUSANDS Net income Interest and other (income) expense Income tax (benefit) expense Depreciation and amortization Restructuring, impairment and related charges, net Change in fair value of warrant liabilities Share-based compensation expense Losses and impairments related to divestitures Revaluation gain previously held equity method investment Other unusual items Adjusted EBITDA Q3 2023 $18,623 (6,260) 4,604 10,753 473 (850) 4,935 4,112 987 $37,377 Q3 2022 $24,313 (662) (91) 8,890 (11,583) 3,858 (34,735) $(10,010) YTD 2023 $19,137 (15,677) 12,002 34,893 8,857 1,419 12,869 4,112 837 $78,449 YTD 2022 $34,636 375 4,077 24,337 (37,869) 8,165 (34,735) 1,110 $96 Adjusted EBITDA We define Adjusted EBITDA as consolidated Net income (loss) excluding interest and other income (expense), income tax (expense) benefit, and depreciation and amortization, adjusted to exclude (i) changes in fair value of warrant liabilities; (ii) share-based compensation expense; and when applicable, (iii) restructuring, impairment and related charges, net; (iv) the net gain or loss from asset disposals; (v) losses and impairments related to divestitures; (vi) revaluation gain on previously held equity method investment; and (vii) certain other unusual items. We present Adjusted EBITDA because we consider it to be an important supplemental measure of the Company's performance and believe it is frequently used by securities analysts, investors, and other interested parties in the evaluation of companies in our industry. Management uses Adjusted EBITDA as a measure of the operating performance of our business on a consistent basis, as it removes the impact of items not directly resulting from our core operations. By providing this non-GAAP financial measure, together with a reconciliation to net income (loss), which is the most comparable GAAP measure, we believe we are enhancing investors' understanding of our business and our results of operations, as well as assisting investors in evaluating how well we are executing our strategic initiatives. However, Adjusted EBITDA has limitations as an analytical tool, and should not be considered in isolation, or as an alternative to, or a substitute for net income (loss) or other financial statement data presented in our Condensed Consolidated Financial Statements as indicators of financial performance. Hagerty's Adjusted EBITDA may be determined or calculated differently than similarly titled measures of other companies in our industry, which could reduce the usefulness of this non-GAAP financial measure when comparing our performance to that of other companies. HAGERTY Q3 2023 | 14#15RECONCILIATION OF NON-GAAP METRICS Basic Earnings Per Share to Adjusted Earnings (Loss) Per Share IN THOUSANDS (EXCEPT PER SHARE AMOUNTS) Numerator: Net income available to Class A Common Stockholders¹ Undistributed earnings allocated to Series A Convertible Preferred Stock Accretion of Series A Convertible Preferred Stock Net income (loss) attributable to non-controlling interest Consolidated net income Change in fair value of warrant liabilities Revaluation gain on previously held equity method investment Adjusted consolidated net income (loss)² Denominator: Weighted-average shares of Class A Common Stock Outstanding - basic¹ Total potentially dilutive shares outstanding: Conversion of non-controlling interest Hagerty Group Units to Class A Common Stock Conversion of Series A Convertible Preferred Stock to Class A Common Stock Total unissued share-based compensation awards Total warrants outstanding Potentially dilutive shares outstanding Fully dilutive shares outstanding² Basic Earnings per Share¹ Adjusted Earnings (Loss) per Share² Q3 2023 $3,255 261 1,838 13,269 18,623 (850) $17,773 84,479 255,499 6,785 8,490 19,484 290,258 374,737 $0.04 $0.05 Q3 2022 $14,714 9,599 24,313 (11,583) (34,735) $(22,005) 82,816 255,758 6,878 19,484 282,120 364,936 $0.18 $(0.06) YTD 2023 $3,712 110 1,838 13,477 19,137 1,419 $20,556 84,042 255,499 6,785 8,490 19,484 290,258 374,300 $0.04 $0.05 YTD 2022 $36,685 (2,049) 34,636 (37,869) (34,735) $(37,968) 82,569 255,758 6,878 19,484 282,120 364,689 $0.44 $(0.10) ¹ Numerator and Denominator of the GAAP measure Basic EPS 2 Numerator and Denominator of the non-GAAP measure Adjusted EPS Adjusted EPS We define Adjusted Earnings (Loss) Per Share ("Adjusted EPS") as consolidated Net income (loss), less the change in fair value of our warrants divided by our outstanding and total potentially dilutive securities, which includes (i) the weighted-average issued and outstanding shares of Class A Common Stock; (ii) all issued and outstanding non-controlling interest Hagerty Group Units; (iii) all unexercised warrants; (iv) all unissued share-based compensation awards; and (v) all issued and outstanding shares of the Series A Convertible Preferred Stock. In the third quarter of 2022, we began removing (i) the change in fair value of our warrants and (ii) the revaluation gain on previously held equity method investment from consolidated Net income (loss) for purposes of calculating Adjusted EPS. For comparability, references to prior period non-GAAP measures have been updated to show the effect of removing the change in the fair value of our warrants from Adjusted EPS. We believe this updated presentation of Adjusted EPS enhances investors' understanding of our financial performance from activities occurring in the ordinary course of our business.. The most directly comparable GAAP measure is basic earnings per share ("Basic EPS"), which is calculated as Net income (loss) available to Class A Common Stockholders divided by the weighted average number of Class A Common Stock shares outstanding during the period. We caution investors that Adjusted EPS is not a recognized measure under GAAP and should not be considered in isolation or as a substitute for, or superior to, the financial information prepared and presented in accordance with GAAP, including Basic EPS, and that Adjusted EPS, as we define it, may be defined or calculated differently by other companies. In addition, Adjusted EPS has limitations as an analytical tool and should not be considered as a measure of profit or loss per share. HAGERTY Q3 2023 | 15#16RECONCILIATION OF NON-GAAP METRICS | 2023 OUTLOOK Net Income to Adjusted EBITDA IN THOUSANDS Net Income Interest and Other (Income) Expense Income Tax (Benefit) Expense Depreciation and Amortization Restructuring, Impairment and Related Charges, Net Change in Fair Value of Warrant Liabilities Share-based Compensation Expense Losses and impairments related to divestitures Adjusted EBITDA 2023 Low $2,000 (18,500) 15,500 44,112 8,857 1,419 17,500 4,112 $75,000 2023 High $12,000 (18,500) 15,500 44,112 8,857 1,419 17,500 4,112 $85,000 Adjusted EBITDA We define Adjusted EBITDA as consolidated Net income (loss) excluding interest and other income (expense), income tax (expense) benefit, and depreciation and amortization, adjusted to exclude (i) changes in fair value of warrant liabilities; (ii) share-based compensation expense; and when applicable, (iii) restructuring, impairment and related charges, net; (iv) the net gain or loss from asset disposals; (v) losses and impairments related to divestitures; (vi) revaluation gain on previously held equity method investment; and (vii) certain other unusual items. We present Adjusted EBITDA because we consider it to be an important supplemental measure of the Company's performance and believe it is frequently used by securities analysts, investors, and other interested parties in the evaluation of companies in our industry. Management uses Adjusted EBITDA as a measure of the operating performance of our business on a consistent basis, as it removes the impact of items not directly resulting from our core operations. By providing this non-GAAP financial measure, together with a reconciliation to net income (loss), which is the most comparable GAAP measure, we believe we are enhancing investors' understanding of our business and our results of operations, as well as assisting investors in evaluating how well we are executing our strategic initiatives. However, Adjusted EBITDA has limitations as an analytical tool, and should not be considered in isolation, or as an alternative to, or a substitute for net income (loss) or other financial statement data presented in our Condensed Consolidated Financial Statements as indicators of financial performance. Hagerty's Adjusted EBITDA may be determined or calculated differently than similarly titled measures of other companies in our industry, which could reduce the usefulness of this non-GAAP financial measure when comparing our performance to that of other companies. HAGERTY Q3 2023 | 16#17RAISED $105M OF CAPITAL IN JUNE OF 2023 TO DRIVE GROWTH AND VALUE CREATION $80M of capital raised at Hagerty, Inc. to support strategic growth initiatives Strong sponsorship from existing strategic investors >> $50M from State Farm >> $15M from Markel Hagerty family investment of $15M Attractive opportunity to deploy capital to drive profitable growth and returns: >> Establish new products to offer differentiated solutions to car enthusiasts >> Support growing Marketplace business including Broad Arrow Capital's lending activity >> Working capital as Hagerty continues to pivot to sustainable profitability by creating a scalable platform for growth in Insurance and Membership >> >> Bolsters cash and liquidity ($264M as of September 30, 2023 with $91M in cash and cash equivalents and $173M available under credit facility) $25M of Tier 2 capital at Hagerty Re provided by State Farm Support growth in our quota share risk taking with Essentia Prepare to take direct risk as we evolve to become a more integrated insurance business Support our efforts to obtain a credit agency rating for Hagerty Re HAGERTY Q3 2023 | 17#18Never Stop Driving HAGERTY