HAGERTY Q4 2022 | 2 S T O C K H O L D E R L E T T E R Springing Forward T.S. Eliot said that April is the cruelest month. For many car lovers, these late winter and early spring days are difficult to bear. The days are getting longer and driving season is almost upon us. We know that miles of great roads lie just in front of us. And we are ready. Hagerty is in a similar transition period. We are proud of how we weathered 2022’s macroeconomic realities, delivering total revenue growth of 27%. But those realities also challenged us to evaluate our strategy and prioritize our investments so that we drive improved profitability in 2023. We intend to do that by focusing on the parts of the business that provide the most underlying value while also looking for ways to drive additional efficiencies. With this approach, we believe we will return to our historic levels of profitability while maintaining strong top line momentum through thoughtful investments. At the core of our competitive advantages is the long-standing strength of the Hagerty brand. We will continue to invest in that brand, our people, and our technology, but with an eye on fiscal discipline. This includes the actions taken during the fourth quarter to reduce our workforce and take a hard look at our overall cost structure as a managing general agency. As I have said before, we have a resilient business model but are not immune to the broader economy. For example, during the darkest moments of 2008 and 2009, we still were able to grow our written premiums in the 7-8% range. While this is lower than the mid-teens growth that we have targeted and delivered, we have since re-accelerated back to 15% growth in 2022 and compounded at 13% over the last decade. Resilience like this does not happen by accident. It is the product of long-term planning and an outstanding product delivered by a dedicated team of employees, whom we call One Team Hagerty. Because of them, our Net Promoter Score increased to a robust 83, double the industry average and proof that we are delivering every day on our promise to provide the very best member experience and a superior value proposition. Dear Hagerty Stockholders, Members and One Team Hagerty,  

HAGERTY Q4 2022 | 3 Though Hagerty has been selling insurance since the 1980s, in many ways, we are just getting started. Currently, we insure roughly 2.2 million vehicles, and yet we are only scratching the surface of the addressable market that we serve with a 4.1% share of the more than 45 million vehicles in North America. This addressable market continues to grow, with 69 million people in the U.S. alone self-describing as “automotive enthusiasts,” and looking to acquire their first enthusiast vehicle. It is a robust opportunity and a highly fragmented market, meaning we are well positioned to lengthen our leadership position by finding new ways to serve our members. Yes, we will continue to sell insurance to more and more of these enthusiasts, but we also expect to see an ever-increasing percentage of our growth come from our broader ecosystem of automotive events, membership services and transactions that we offer and enable. The newest part of that ecosystem is our buy/ sell Marketplace, which aims to be a leading global trading platform in the collector car industry, differentiated by the quality of cars offered, the best advice based on research and data analytics, and exceptional client service. A key piece of this was our acquisition of Broad Arrow Group, a newly formed team of industry veterans with a track record of success in the live auction, private sale, and asset-lending space. The market seems to agree. By the end of the 2022 – in just five months – Broad Arrow tallied $86 million in vehicle sales. Earlier this year, we also launched digital auction sales through Marketplace. While still in test mode, we believe Marketplace – fueled by the trusted Hagerty name and new confidence-building features for buyers – will prove popular and allow us to capture a meaningful piece of the global transactional market for collectible vehicles, the value of which measures over one trillion dollars in vehicle value and billions of potential commissions. Since becoming a publicly listed company on the New York Stock Exchange in December of 2021, our share price, despite the typical ups and downs, has performed well against well- established indices, and even better against U.S. Auto Written Premium Annual Growth 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 —% 3% 5% 8% 10% 13% 15% 18% 20%

HAGERTY Q4 2022 | 4 newly listed companies. We believe this is indicative of the good things to come. It means our investors believe in the fundamentals of our business, our future growth potential, and our path to dramatically improved profitability. We have a detailed long-term strategy and a team that is committed to achieve our 2023 plans. We are building on our strengths and history and yet executing with agility to address the significant opportunity in the auto enthusiast world. They say the only constant in life is change. And that is certainly true of our uncertain spring weather here in Michigan, our home base, and the fits and starts of the global economy. However, we are fortunate to operate in a space where there is one constant, and that is the universal passion for cool cars and great drives with our loved ones. Our opportunity as a company, and as a movement, has never been greater. And while no one is immune to difficult times, agile companies adjust as necessary, reorient on the road ahead, and punch the accelerator. That is precisely what we intend to do in 2023. Keep on driving!   McKeel Hagerty CEO, Hagerty 

FORWARD LOOKING STATEMENTS / NON-GAAP FINANCIAL MEASURES This presentation contains forward-looking statements within the meaning of 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 increases in earned premium; (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 “aim,” “anticipate,” “believe,” “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, but are not limited to: (i) our ability to compete effectively within our industry and attract and retain members; (ii) our dependence on a limited number of insurance distribution and underwriting carrier partners; (iii) our ability to prevent, monitor and detect fraudulent activity, including our reliance on a limited number of payment processing services; (iv) disruptions, interruptions, outages with our technology platforms or third-party services; (v) the limited operating history of some of our membership products and the success of any new insurance programs and products; (vi) adverse impacts from the COVID-19 pandemic and current and future variants of the virus; (vii) manage the cyclical nature of the insurance business, including through any periods of recession, economic downturn or inflation; (viii) unexpected increases in the frequency or severity of claims; (ix) compliance 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; (x) whether investors or securities analysts view our stock structure unfavorably, particularly our dual-class structure; (xi) the fact that we are a controlled company; and (xii) other risks and uncertainties indicated from time to time in documents we file or will file with the Securities and Exchange Commission (the “SEC”). 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 terms”. 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.

Total Revenue growth of 27% Written Premium growth of 15% Broad Arrow Group acquisition » Three live auctions with $86 million in total vehicle sales » Expect to begin writing new policies in 2023 State Farm partnership progressing well through the testing phase and regulatory approval process 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 ($20) - $0 million » Adjusted EBITDA (1) of $40 - $60 million KEY 2022 HIGHLIGHTS 2023 OUTLOOK 1 See Appendix for additional information regarding this non-GAAP financial measure.

» Significant adjacent market opportunity with ~300,000 cars transacting for ~$12.5 billion through Hagerty’s insurance book in 2022 » Executed three live auctions with $86 million in total vehicle sales helping drive $14 million in Marketplace revenue in 2022 » Other opportunities include insurance sales, Hagerty Drivers Club (HDC) memberships, Hagerty Garage + Social (HG+S) storage fees, media sales and owner/ operator event revenue » Launched Marketplace online auctions during the fourth quarter » Proven leadership team with strong cultural fit HAGERTY MARKETPLACE

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 » 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 » 460,000+ existing collector car policies and up to 75% HDC enrollment possible on new insurance policies

» 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 » Continue evolution into an Integrated Insurance Business » Increase Hagerty Re’s quota share reinsurance agreement in the U.S. and U.K. to ~80% » Significantly improve profitability ($40 million to $60 million in Adjusted EBITDA (1)) through cost containment measures and operational efficiencies 2023 - PIVOT TO PROFITABILITY 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.

2023 OUTLOOK Strong top-line momentum expected to continue in 2023 with significantly improved profitability 2022 Results 2023 Outlook 2022 Results vs 2023 Outlook in thousands Low End Range High End Range Low End Range High End Range Total Revenue $787,588 $961,000 $993,000 22% 26% Total Written Premium $776,664 $862,000 $878,000 11% 13% Net Income (Loss) $2,403 $(20,000) $— $(22,403) $(2,403) Adjusted EBITDA1 $(1,940) $40,000 $60,000 $41,940 $61,940 1 See Appendix for additional information regarding this non-GAAP financial measure.

REVENUE COMPONENTS 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. $154 $197 $83 $112 $13 $21$58 $64 Q4 2021 Q4 2022 $619 $788 $296 $403 $52 $78 $271 $307 YTD Q4 2021 YTD Q4 2022 M illi on s Total Revenue Commission + fee revenue1 Membership, marketplace + other revenue Earned premium in Hagerty Reinsurance 11% 56% 35% Growth 13% 50% 36% Growth GROWTH 27% GROWTH 27% Q4 YTD Commission + fee revenue (+13%) » Written Premium growth 15% » Policies in Force retention of 88.0% Membership, marketplace + other revenue (+50%) » Membership revenue growth of 11% » Marketplace delivered $14 million in revenue, including $8 million in auction revenue » 75% of new insurance customers join HDC Earned premium in Hagerty Reinsurance (+36%) » Contractual quota share2 increased to 70% in 2022 2022 Highlights

1 Adjusted EBITDA and Net Income (Loss) in 2022 were negatively impacted by $16.5 million in losses related to Hurricane Ian and increased 2022 U.S. reserves, as well as a $4.1 million reduction in CUC. 2 See Appendix for additional information regarding this non-GAAP financial measure. $(66) $(32) $(61) $2 $(3) $(2) $25 $(2) Q4 2021 Q4 2022 YTD Q4 2021 YTD Q4 2022 Adjusted EBITDA Net Income (Loss)M illi on s Adjusted EBITDAQ4 YTD EARNINGS ANALYSIS IN THOUSANDS Q4 2021 Q4 2022 YTD 2021 YTD 2022 Net Income (Loss)1 $(66,459) $(32,233) $(61,354) $2,403 Interest and Other (Income) Expense 952 (2,403) 1,993 (2,028) Income Tax (Benefit) Expense 1,962 2,940 6,751 7,017 Depreciation and Amortization 6,862 9,550 22,144 33,887 Restructuring, Impairment and Related Charges, Net — 18,324 — 18,324 Change in Fair Value of Warrant Liabilities 42,540 (4,030) 42,540 (41,899) Stock-based Compensation Expense — 3,964 — 12,129 Revaluation Gain on Previously Held Equity Method Investment — — — (34,735) Accelerated Vesting of Incentive Plans 9,321 — 9,321 — Net (Gain) Loss from Asset Disposals — 1,970 1,764 1,970 Other Unusual Items 2,191 (118) 2,191 992 Adjusted EBITDA1, 2 $(2,631) $(2,036) $25,350 $(1,940) Net Income (Loss) and Adjusted EBITDA include substantial pre-revenue costs related to scaling infrastructure, legacy systems and newly-developed digital platforms, human resources and occupancy to accommodate our alliance with State Farm and other potential distribution partnerships as well as to further develop our Marketplace transactional platform. 2021 $31M | 2022 $30M Pre-Revenue Investments for Growth

1 Hagerty’s 2022 loss ratio of 45.3% includes the $10.0 million impact from Hurricane Ian (2.5%) and increased U.S. reserves of $6.5 million (1.6%). 2 See Appendix for additional information regarding this non-GAAP measure. FULL YEAR 2022 FINANCIAL HIGHLIGHTS 45.3% Loss Ratio1Total Revenue 88.0% Retention (1)% $777M Written Premium 15% GROWTH PERSISTENCE PROFITABILITY $(68)M Operating Income (Loss) $(2)M Adjusted EBITDA2 $2M Net Income (Loss) $788M 27% 4.0% $0.39 Basic Earnings Per Share

On Mission On Track 2022 + Beyond Full Year 2022 Progress Insurance » Grow omnichannel distribution (onboard new partners and deepen existing) » Expand share of insurance underwriting profit » Deliver frictionless experience (sales, service, claims) » State Farm partnership progress continues with regulatory approvals and systems testing » Delivering key broker results and encouraging success with private client efforts » 2022 rate approvals completed, increasing impact on written premium growth Reinsurance » Increase contractual quota share » Grow international footprint » U.S. and U.K. Reinsurance Quota Share up to 70% further increasing our share of profit Membership » Drive increase in paid membership » Enhance value proposition » Develop partnership model » Expand to international markets » Paid HDC membership increased 5% to ~753,000 Members » HDC average revenue per new Member grew 10% to $65 as we moved to a single tier at $70/year » HDC attach rate of approximately 75% » Launched new HDC digital onboarding journey » HG+S ended the year with nine locations and over 1,500 HG&S Members after expanding with additional locations in Palm Beach, FL; Van Nuys, CA; and Culver City, CA Marketplace » Leverage Broad Arrow Group investment » Launch live and time-based auctions » Grow asset-based lending » Newly acquired Broad Arrow Group delivered $10.8 million in revenue during 2022 » Produced live auction sales of $86 million (838 lots sold and an 84% sell through rate) » Launched online auctions, an addition to augment the existing Marketplace business » Acquired Speed Digital, a software-as-a-service solution for classic car dealers & auction houses » Launched Hagerty Classifieds, a platform for car enthusiasts to buy and sell » Large and growing market opportunity demonstrated by ~300,000 cars transacting for ~$12.5 billion through Hagerty’s insurance book over the last twelve months Media + Entertainment » Develop owned and operated events » Expand digital audience » Leverage Sony partnership with Gran Turismo gaming platform » Expand video distribution » Increase advertising and sponsorship revenue » Hagerty’s YouTube content generated >100 million views with 721,000 added subscribers » Hagerty’s media website had average monthly page views of 2.4 million » Announced a multi-year commercial partnership with Exxon Mobil1 » Launched our annual car valuation media franchise Bull Market across print, digital and video channels with 232,000 page views on our website and 14 million impressions on YouTube » Held the rebranded Motorlux event that kicked off Monterey Car Week and used the event to preview the Broad Arrow Group auction with 3,200 ticketed attendees and over 50 sponsors » Held the inaugural Detroit Concours with ~5,000 participants in the heart of downtown Motor City Impact » Create carbon neutrality plan » Establish government affairs program » Rolled out carbon neutral driving event strategy at the California Mille » First draft of enthusiast carbon offset program designed for a 2023 launch MILESTONES & HIGHLIGHTS

3 Hagerty’s 2022 loss ratio of 45.3% includes the $10.0 million impact from Hurricane Ian (2.5%) and increased U.S. reserves of $6.5 million (1.6%). 2 Metrics measured as of the end of the period. 1 See Appendix for additional information regarding these non-GAAP financial measures. QUARTERLY KEY PERFORMANCE INDICATORS Q1 2021 Q2 2021 Q3 2021 Q4 2021 TOTAL 2021 Q1 2022 Q2 2022 Q3 2022 Q4 2022 TOTAL 2022 HDC Paid Member Count2 666,609 690,407 711,749 718,583 718,583 727,010 742,825 749,740 752,754 752,754 Total Written Premium (thousands) $133,707 $208,091 $192,091 $140,416 $674,305 $154,790 $237,697 $222,136 $162,041 $776,664 New Business Count (Insurance) 51,799 77,013 68,077 47,589 244,478 47,514 74,922 68,561 43,523 234,520 Policies in Force Retention2 90.0% 89.3% 89.0% 89.1% 89.1% 88.9% 88.2% 88.0% 88.0% 88.0% Loss Ratio3 41.4% 41.4% 41.0% 41.3% 41.3% 41.4% 41.0% 56.4% 41.2% 45.3% Total Revenue (thousands) $129,200 $167,409 $168,086 $154,384 $619,079 $167,811 $206,017 $216,757 $197,003 $787,588 Net Promoter Score2 82 81 81 82 82 82 82 82 83 83 Operating Income (Loss) (thousands) $(5,096) $14,274 $1,758 $(21,006) $(10,070) $(13,004) $2,387 $(21,223) $(35,726) $(67,566) Net Income (Loss) (thousands) $(6,850) $12,503 $(548) $(66,459) $(61,354) $15,866 $(5,543) $24,313 $(32,233) $2,403 Basic Earnings (Loss) per Share N/A N/A N/A $(0.56) $(0.56) $0.33 $(0.07) $0.18 ($0.06) $0.39 Adjusted EBITDA1 (thousands) $1,039 $19,299 $7,644 $(2,632) $25,350 $(5,959) $16,065 $(10,010) $(2,036) $(1,940) Adjusted Earnings (Loss) per Share1 N/A N/A N/A $(0.07) $(0.05) $0.04 $(0.02) $(0.06) $(0.10) $(0.20)

HISTORICAL WRITTEN PREMIUM GROWTH Total U.S. Auto Written Premium U.S. Auto Written Premium Annual Growth Growing during good times and bad 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 0 100 200 300 400 500 600 700 800 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 —% 3% 5% 8% 10% 13% 15% 18% 20%

PROVEN TRACK RECORD OF PROFITABLE LONG-TERM GROWTH 1 Hagerty’s 2022 loss ratio of 45.3% includes the $10.0 million impact from Hurricane Ian (2.5%) as well as the increased U.S. liability reserves of $6.5 million (1.6%). Recently implemented rate changes expected to drive 2023 loss ratios in line with historical results. Source: Hagerty Internal Data, S&P Global Market Intelligence (2022). Hagerty U.S. Auto Premium Growth vs. Industry Top 100 Hagerty U.S. Auto - CAGR 13% Industry Top 100 - CAGR 4% Sustained Growth 5X the Industry Top 100 Hagerty U.S. Auto Loss Performance vs. Industry Top 100 To ta l L os s Pe rfo rm an ce 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 20% 30% 40% 50% 60% 70% 80% Hagerty Loss Ratio - average = 38% Industry Loss Ratio - average = 66% Stable and Predictable Loss Performance well below Industry Average To ta l P er ce nt ag e G ro w th 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 0 100 200 300 400 59% 288% Written Premium Growth 2010-2021 CAGR 2022 Hagerty 13% 15% Industry 4% Delta 9% Loss Ratio 2010-2021 Average 2022 Hagerty1 38% 45% Industry 66% Delta (28)%

Total Written Premium New Business Count (Insurance) HISTORICAL SEASONALITY TRENDS $ IN THOUSANDS Q1 Q2 Q3 Q4 Total 2018 82,514 137,943 123,385 86,621 430,463 2019 96,732 158,501 142,030 99,747 497,010 2020 112,421 184,423 163,520 117,870 578,234 2021 133,707 208,091 192,091 140,417 674,306 2022 154,790 237,697 222,136 162,041 776,664 5 Year Average Total Written Premium % 20% 31% 29% 20% 100% Q1 Q2 Q3 Q4 Total 2018 32,610 56,729 51,795 35,356 176,490 2019 36,848 62,842 57,426 37,585 194,701 2020 41,510 70,622 73,619 50,914 236,665 2021 51,799 77,013 68,077 47,589 244,478 2022 47,514 74,922 68,561 43,523 234,520 5 Year Average New Business Count % 19% 32% 29% 20% 100% 0 50 100 150 200 250 0 10 20 30 40 50 60 70 80 90 North American footprint creates seasonal differences by quarter for written premium and new business count

21% 27% 28% 25% Q1 Q2 Q3 Q4 —% 10% 20% 30% 40% (8)% 47% 52% 9% Q1 Q2 Q3 Q4 (30)% (20)% (10)% —% 10% 20% 30% 40% 50% 60% 70% Total Revenue Operating Income 5 YEAR AVERAGE 5 YEAR AVERAGE Geographic footprint of our North American book creates seasonal differences by quarter for revenue and operating income HISTORICAL SEASONALITY TRENDS $ IN THOUSANDS Q1 Q2 Q3 Q4 Total 2018 60,489 85,799 83,864 71,547 301,699 2019 78,479 109,722 111,472 97,601 397,274 2020 106,859 135,462 135,781 121,446 499,548 2021 129,200 167,409 168,086 154,384 619,079 2022 167,811 206,017 216,757 197,003 787,588 5 Year Average Total Revenue % 21% 27% 28% 25% 100% $ IN THOUSANDS Q1 Q2 Q3 Q4 Total 2018 (2,880) 12,968 6,861 (8,337) 8,612 2019 (5,508) 13,247 9,258 (6,149) 10,848 2020 (4,171) 17,441 12,650 (10,074) 15,846 2021 (5,096) 14,274 1,758 (21,006) (10,070) 2022 (13,004) 2,387 (21,223) (35,726) (67,566) 4 Year Average Operating Income % (8)% 47% 52% 9% 100%

1 Includes base commissions, payment plan fees and contingent underwriting commissions. REVENUE COMPONENTS BY QUARTER 50 53 57 60 63 70 79 83 89 94 107 112 Q1 2020 Q2 2020 Q3 2020 Q4 2020 Q1 2021 Q2 2021 Q3 2021 Q4 2021 Q1 2022 Q2 2022 Q3 2022 Q4 2022 46 72 68 50 54 83 76 58 62 96 86 64 Q1 2020 Q2 2020 Q3 2020 Q4 2020 Q1 2021 Q2 2021 Q3 2021 Q4 2021 Q1 2022 Q2 2022 Q3 2022 Q4 2022 10 11 11 11 12 14 13 13 16 16 24 21 Q1 2020 Q2 2020 Q3 2020 Q4 2020 Q1 2021 Q2 2021 Q3 2021 Q4 2021 Q1 2022 Q2 2022 Q3 2022 Q4 2022 Earned premium in Hagerty Reinsurance Commission + fee revenue1 Membership, marketplace + other revenue $ IN MILLIONS

1 Metrics measured as of the end of the period. SUPPLEMENTAL FINANCIAL INFORMATION Policies and Vehicles in Force Policies in Force1 Q1 2021 Q1 2022 Q2 2021 Q2 2022 Q3 2021 Q3 2022 Q4 2021 Q4 2022 % Growth U.S. 1,020,638 1,101,557 1,051,423 1,124,545 1,072,634 1,140,892 1,080,909 1,147,920 6% CAN 126,039 136,136 131,494 140,820 134,196 142,671 133,515 141,155 6% U.K. 24,517 26,224 25,091 26,773 25,675 27,083 32,632 26,902 (18)% Total 1,171,194 1,263,917 1,208,008 1,292,138 1,232,505 1,310,646 1,247,056 1,315,977 6% Vehicles Covered1 Q1 2021 Q1 2022 Q2 2021 Q2 2022 Q3 2021 Q3 2022 Q4 2021 Q4 2022 % Growth U.S. 1,724,680 1,874,514 1,776,202 1,919,325 1,815,734 1,955,747 1,861,248 1,974,196 6% CAN 175,331 190,224 182,767 196,802 186,801 199,940 188,518 200,880 7% U.K. 53,367 57,044 49,205 58,636 56,270 59,425 53,419 59,385 11% Total 1,953,378 2,121,782 2,008,174 2,174,763 2,058,805 2,215,112 2,103,185 2,234,461 6%

Guest User Counts Q4 2021 Q4 2022 U.S. 1,116,451 1,202,465 Canada 73,321 79,497 7% growth Total Guest User Count 1,189,772 1,281,962 Guest User An individual who has created an online profile by providing email, establishing a password, and verifying email. Paid Membership Counts U.S. Q4 2021 Q4 2022 Insurance Member 443,137 465,003 Insurance + HDC 630,323 661,583 HDC Standalone 31,817 30,486 Total U.S. Paid Member Count 1,105,277 1,157,072 Canada Insurance Member 79,692 81,511 Insurance + HDC 53,763 59,487 HDC Standalone 2,680 1,198 Total Canada Paid Member Count 136,135 142,196 Total Insurance Member 522,829 546,514 Insurance + HDC 684,086 721,070 HDC Standalone 34,497 31,684 Total HDC Paid Member Count 718,583 752,754 5% growth Total Paid Member Count 1,241,412 1,299,268 5% growth SUPPLEMENTAL FINANCIAL INFORMATION Total Member Count 1.3 million Paid Members (+5%)

Adjusted EBITDA We define Adjusted EBITDA as consolidated net income (loss) (the most directly comparable GAAP measure) before 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 the fair value of warrant liabilities, (iii) stock-based compensation expense, (iv) the revaluation gain on a previously held equity method investment, (v) expense associated with the accelerated vesting of incentive plans, (vi) net gains and losses from asset disposals and (vii) 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. Our management uses Adjusted EBITDA: as a measurement of operating performance of our business on a consistent basis, as it removes the impact of items not directly resulting from our core operations; for planning purposes, including the preparation of our internal annual operating budget and financial projections; to evaluate the performance and effectiveness of our operational strategies; to evaluate our capacity to expand our business; as a performance factor in measuring performance under our executive compensation plan; and as a predictor of core operating performance, comparisons to prior periods and competitive positioning. 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. 1 Other unusual items in 2021 relates to expenses incurred related to the Business Combination. Other unusual items in 2022 relates to certain severance and legal settlement expenses. RECONCILIATION OF NON-GAAP METRICS Net Income (Loss) to Adjusted EBITDA IN THOUSANDS Q4 2021 Q4 2022 YTD 2021 YTD 2022 Net Income (Loss) ($66,459) ($32,233) ($61,354) $2,403 Interest and Other (Income) Expense 952 (2,403) 1,993 (2,028) Income Tax (Benefit) Expense 1,962 2,940 6,751 7,017 Depreciation and Amortization 6,862 9,550 22,144 33,887 Restructuring, Impairment and Related Charges, Net — 18,324 — 18,324 Change in Fair Value of Warrant Liabilities 42,540 (4,030) 42,540 (41,899) Stock-based Compensation Expense — 3,964 — 12,129 Revaluation Gain on Previously Held Equity Method Investment — — — (34,735) Accelerated Vesting of Incentive Plans 9,321 — 9,321 — Net (Gain) Loss from Asset Disposals — 1,970 1,764 1,970 Other Unusual Items1 2,191 (118) 2,191 992 Adjusted EBITDA ($2,631) ($2,036) $25,350 ($1,940)

Adjusted EPS 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. RECONCILIATION OF NON-GAAP METRICS Basic Earnings Per Share to Adjusted Earnings (Loss) Per Share 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) IN THOUSANDS EXCEPT FOR PER SHARE AMOUNTS Q4 2021 Q4 2022 YTD 2021 YTD 2022 Net Income attributable to controlling interest1 ($46,358) ($4,607) ($46,358) $32,078 Net Income (Loss) attributable to non-controlling interest (194) (27,626) (398) (29,675) Net Income (Loss) attributable to redeemable non-controlling interest (19,907) — (14,598) — Consolidated net income (loss) ($66,459) ($32,233) ($61,354) $2,403 Change in fair value of warrants 42,540 (4,030) 42,540 (41,899) Revaluation gain on previously held equity method investment — — — (34,735) Adjusted Consolidated Net Income (Loss)2 ($23,919) ($36,263) ($18,814) ($74,231) Weighted-average shares of Class A Common Stock Outstanding: Basic1 82,327 83,203 82,327 82,728 Potentially dilutive shares outstanding: Conversion of non-controlling interest Hagerty Group Units to Class A Common Stock 251,034 255,758 251,034 255,758 Total warrants outstanding 20,006 19,484 20,006 19,484 Total unissued stock-based compensation — 6,902 — 6,902 Potentially dilutive shares outstanding 271,040 282,144 271,040 282,144 Fully dilutive shares outstanding2 353,367 365,347 353,367 364,872 Basic Earnings per Share1 ($0.56) ($0.06) ($0.56) $0.39 Adjusted Earnings (Loss) per Share2 ($0.07) ($0.10) ($0.05) ($0.20) 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. 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.