#1103 Q1 Investor Presentation Speakers: McKeel Hagerty | Chief Executive Officer Patrick McClymont | SVP & Chief Financial Officer 500 11 HAGERTY#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 Q1 2023 | 2#36 KEY Q1 2023 HIGHLIGHTS Total Revenue growth of 30% Written Premium growth of 18% Improved Profitability >> Net Income (Loss) of $(15) million compared to $16 million in the prior year period due primarily to the $32 million change in fair value of the warrant liabilities Adjusted EBITDA of $7 million, an improvement of $13 million from the prior year period's loss of $6 million >> Q1 restructuring should yield an incremental $20 million to $25 million of annualized savings, including $15 million in 2023 2023 OUTLOOK Pivot to significantly improved profitability fueled by top- line momentum, cost containment & efficiency measures >> Total Revenue growth of 22-26% » Written Premium growth of 11-13% » Net Income (Loss) of $(13)-7 million Adjusted EBITDA (¹) of $55-75 million 2023 Outlook as of the Company's fourth quarter earnings call on March 14th, 2023 was for Net income (loss) of $(20) to $0 million and Adjusted EBITDA of $40 to $60 million. ¹ See Appendix for additional information regarding this non-GAAP financial measure. HAGERTY Q1 2023 | 3#4HAGERTY 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 opportunities include insurance sales, Hagerty Driver's Club (HDC) memberships, Hagerty Garage + Social (HG+S) storage fees, media sales and owner/ operator event revenue >> Proven leadership team with strong cultural fit HAGERTY Q1 2023 | 4#5INAISON HAGERTY + STATE FARM PARTNERSHIP >> Digital and technology teams are progressing through the testing phase and regulatory approval process Expect to begin activating State Farm's approximately 19,200 agents to sell classic car policies in 2023 >> 480,000+ existing collector car policies and up to 75% HDC enrollment possible on new insurance policies >> Anticipated average annual revenue per customer: $85-$110 State Farm aligned in the success of the strategic partnership with $500 million investment in Hagerty and 10-year initial contract State Farm HAGERTY. HAGERTY Q1 2023 |#62023 PRIORITIES Strong top-line momentum expected to continue in 2023 with significantly improved profitability Total Revenue growth of 22-26% powered by Written Premium growth of 11-13% >> 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 improved profitability ($55 million to $75 million in Adjusted EBITDA¹) through Cost Containment measures and Operational Efficiencies ¹ See Appendix for additional information regarding this non-GAAP measure. W HAGERTY Q1 2023 | 6 A#7GROWTH $218M Total Revenue 30% $183M Written Premium 18% ¹ See Appendix for additional information regarding this non-GAAP measure. Q1 2023 FINANCIAL HIGHLIGHTS PERSISTENCE 41.3% Loss Ratio 87.9% Retention PROFITABILITY $(16) M Operating Income (Loss) $7M Adjusted EBITDA¹ $(15) M Net Income (Loss) $(0.03) Basic Earnings (Loss) Per Share HAGERTY Q1 2023 |#8Millions Total Revenue Q1 2023 Commission + fee revenue¹ Membership, marketplace + other revenue Earned premium in Hagerty Reinsurance GROWTH 30% $167 $62 $16 $89 Q1 2022 $218 $75 $26 REVENUE COMPONENTS $117 Q1 2023 Growth 19% 63% 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. Q1 2023 Highlights Commission + fee revenue (+19%) >> Written Premium growth 18% >> Policies in Force retention of 87.9% Membership, marketplace + other revenue (+63%) Membership revenue growth of 22% Marketplace delivered $7 million in revenue »> 77% of new insurance customers join HDC >> Earned premium in Hagerty Reinsurance (+32%) >> Contractual quota share² increased to ~80% in 2023 HAGERTY Q1 2023 | 8#9Millions $16 Adjusted EBITDA Net Income (Loss) Q1 2022 $(6) Q1 2023 $(15) ¹ See Appendix for additional information regarding this non-GAAP financial measure. EARNINGS ANALYSIS Significantly improved profitability Q1 2023 $7 Adjusted EBITDA IN THOUSANDS Net Income (Loss) 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 Stock-based Compensation Expense Adjusted EBITDA¹ Q1 2023 $(15,025) (5,647) 3,668 13,743 5,535 515 3,916 $6,705 Q1 2022 $15,866 684 2,030 7,147 (31,686) $(5,959) HAGERTY Q1 2023 | 9#10in thousands Total Revenue Total Written Premium Net Income (Loss) Adjusted EBITDA¹ 2023 OUTLOOK Strong top-line momentum expected to continue in 2023 with significantly improved profitability ¹ See Appendix for additional information regarding this non-GAAP financial measure. 2022 Results $787,588 $776,664 $2,403 $(1,940) 2023 Outlook Low End Range $961,000 $862,000 $(13,000) $55,000 High End Range $993,000 $878,000 $7,000 $75,000 2022 Results vs 2023 Outlook High End Range 26% 13% $4,597 $76,940 Low End Range 22% 11% $(15,403) $56,940 HAGERTY Q1 2023 | 10#11APPENDIX#12MILLIONS 250 200 150 100 50 $ IN THOUSANDS holl 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 Q1 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 Q1 2022 447,473 640,239 29,271 1,116,983 79,890 54,424 3,076 137,390 527,363 694,663 32,347 727,010 1,254,373 Q1 2023 475,425 674,897 32,850 1,183,172 82,304 58,851 1,274 142,429 557,729 733,748 34,124 767,872 1,325,601 HAGERTY MEMBERSHIP Total Member Count 1.3 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. 6% growth 6% growth 8% growth Guest User Counts U.S. Canada Total Guest User Count Q1 2022 1,139,099 74,526 1,213,625 Q1 2023 1,228,161 80,358 1,308,519 Guest Member An individual who has created an on-line profile by providing email, establishing a password, and verifying email. HAGERTY Q1 2023 | 13#14RECONCILIATION OF NON-GAAP METRICS Net Income (Loss) to Adjusted EBITDA IN THOUSANDS Net Income (Loss) 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 Stock-based Compensation Expense Adjusted EBITDA Q1 2023 ($15,025) (5,647) 3,668 13,743 5,535 515 3,916 $6,705 Q1 2022 $15,866 684 2,030 7,147 (31,686) ($5,959) 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) restructuring, impairment and related charges, net; (ii) changes in fair value of warrant liabilities; (iii) stock-based compensation expense; (iv) when applicable, the net gain or loss from asset disposals; and (v) when applicable certain other unusual items. We present Adjusted EBITDA because we consider it to be an important supplemental measure of our performance and believe it is frequently used by securities analysts, investors, and other interested parties in the evaluation of companies in our industry. By providing this non-GAAP financial measure, together with a reconciliation to net income (loss), which is the most directly 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, a substitute for net income (loss) or other financial statement data presented in our 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 Q1 2023 | 14#15RECONCILIATION OF NON-GAAP METRICS Basic Earnings (Loss) Per Share to Adjusted Earnings (Loss) Per Share IN THOUSANDS EXCEPT FOR PER SHARE AMOUNTS Net Income (Loss) attributable to controlling interest¹ Net Income (Loss) attributable to non-controlling interest Consolidated Net Income (Loss) Change in Fair Value of Warrant Liabilities Adjusted Consolidated Net Income (Loss)² Weighted-average shares of Class A Common Stock Outstanding: Basic¹ Potentially dilutive shares outstanding: Conversion of non-controlling interest Hagerty Group Units to Class A Common Stock Total warrants outstanding Total unissued stock-based compensation Potentially dilutive shares outstanding Fully dilutive shares outstanding² Basic Earnings (Loss) per Share¹ Adjusted Earnings (Loss) per Share² ¹ Numerator and Denominator of the GAAP measure Basic EPS (Net income (loss) attributable to controlling interest / Weighted-average shares of Class A Common Stock outstanding) 2 Numerator and Denominator of the non-GAAP measure Adjusted EPS (Adjusted consolidated net income (loss) / Fully dilutive shares outstanding) Q1 2023 ($2,099) (12,926) ($15,025) 515 ($14,510) 83,227 255,640 19,484 6,870 281,994 365,221 ($0.03) ($0.04) Q1 2022 $27,507 (11,641) $15,866 (31,686) ($15,820) 82,433 251,034 19,484 270,518 352,951 $0.33 ($0.04) Adjusted EPS We define Adjusted Earnings (Loss) Per Share ("Adjusted EPS") as consolidated Net income (loss) attributable to both our controlling and non-controlling interest, less the change in fair value of our warrants and the revaluation gain on previously held equity method investment, divided by our outstanding and total potentially dilutive securities. The total potentially dilutive securities includes (1) the weighted-average issued and outstanding shares of Class A Common Stock, (2) all issued and outstanding non-controlling interest Hagerty Group Units, (3) all unexercised warrants and (4) all unissued stock-based compensation awards. In the third quarter of 2022, we began removing (1) the change in fair value of our warrants and (2) the revaluation gain on previously held equity method investment from consolidated Net income (loss) attributable to both our controlling and non-controlling interest 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) attributable to controlling interest divided by the weighted average of Class A Common Stock 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 Q1 2023 | 15#16RECONCILIATION OF NON-GAAP METRICS | 2023 OUTLOOK Net Income (Loss) to Adjusted EBITDA IN THOUSANDS Net Income (Loss) 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 Stock-based Compensation Expense Adjusted EBITDA 2023 Low ($13,000) (10,750) 14,300 41,700 5,535 515 16,700 $55,000 2023 High $7,000 (10,750) 14,300 41,700 5,535 515 16,700 $75,000 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) restructuring, impairment and related charges, net; (ii) changes in fair value of warrant liabilities; (iii) stock-based compensation expense; (iv) when applicable, the net gain or loss from asset disposals; and (v) when applicable certain other unusual items. We present Adjusted EBITDA because we consider it to be an important supplemental measure of our performance and believe it is frequently used by securities analysts, investors, and other interested parties in the evaluation of companies in our industry. By providing this non-GAAP financial measure, together with a reconciliation to net income (loss), which is the most directly 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 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 Q1 2023 | 16#17Never Stop Driving HAGERTY