#1HAGERTY MICHELIN Investor Overview TRANN#2FORWARD 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 here in 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.#3It Saving Driving and Fueling Car Culture for Future Generations To meet that challenge, we are building an ecosystem of high value-added products, services and entertainment for car lovers that honors and catalyzes the passion for cars and driving. MCKEEL HAGERTY#4Hagerty: A Leading Auto Enthusiast Insurance Provider We are leveraging Hagerty's trusted brand status in insurance to become the leading consumer lifestyle brand focused on car lovers Hagerty's Four Strategic Focus Areas Marketplace Insurance Media & Entertainment Membership 2022 loss ratio includes the third quarter impact from hurricane lan (2.5%) and decision to increase liability reserves (1.6%) $788M Total Revenue +27% YOY $777M Written Premium +15% YOY 2.2M 2022 KPIs Vehicles Insured. 45%* Loss Ratio 88% Retention 83 Net Promoter Score 4#5The Hagerty Affinity Ecosystem More than a great specialty insurance business 01 Large and underpenetrated market opportunity Tapping underserved passion-led automotive enthusiast market Never 02 High growth auto enthusiast insurance Established platform to drive scale and leverage data advantage 03 Membership, Marketplace and Media ecosystem for car lovers Exceptional brand loyalty with multiple points of monetization Stop 04 Proven and resilient financial profile Track record of revenue and profit growth 05 Investing in sustained revenue growth and margin expansion Reinvesting to scale the Hagerty ecosystem Driving 5#6A Engaging Through a Shared Love and Passion for Cars Status Competition Ritual Community ONBILET D Family Fun TRIDENT B 6#7Hagerty's Auto Enthusiast Model Maximizes Lifetime Value Weaving together an ecosystem of offerings for consumers The Auto Enthusiast spends >$10K/year Enjoyment + social Insurance Guaranteed value policies Restoration Body, mechanicals, engine Connection and Community Auto club, storage, events, shows Fun Swag, media, gaming Status Prestige, recognition Illustrative Economic Value with 90% retention 10 Year Life Reader Survey 2020; Based on internal records NSX The Daily Driver Focus on mobility Insurance Gas Car lease Parking Maintenance Illustrative Economic Value 2-3 Year Life 7#867mm Auto Enthusiasts Create a Long Runway For Growth Just ~4% share of the U.S. collectible car market today Hagerty Insured Vehicles 2.4mm U.S. Car Enthusiasts 67mm U.S. Collectible Cars² 45mm Global Car Enthusiasts 1 >500mm Age groups & demographics Late teens 20s 50s High net worth individuals 30s 60s Hobbyists at home 40s 70s & beyond Industry professionals Source: Hagerty company reports based on aggregated data of various sources; 1 Per Facebook analytics, members who have expressed an interest in or 'Liked" automobiles or associated interests 2 Per Hagerty company reports based on aggregate data of various sources. 3 Policies in force of 1.4mm as of October 31, 2023 8#9The Automobile Enthusiast Market Compares Favorably to other Lifestyle Segments Hagerty is the Leading Platform in a Large and Fragmented Segment 3mm Surfing a O'NEILL H BILLABONG QUIKSILVER 9mm Skiing VAIL RESORTS EXPERIENCE OF A LIFETIME ATOMIC SKI S ke SPORTSA L BURTON 24mm Golf Titleist CLUBCORPⓇ Callaway GOLF TOPGOLF 42mm Outdoor KREI www.rei.com patagonia ARC'TERYX 60mm Fitness SPI Membership models Source: Polk, National Ski Areas Association, Outdoor Foundation, Statista, MRI; Note: Bubbles represent estimated number of participants; 1¹ U.S. collectible vehicles PELOTON SOULCYCLE BARRY'S EQU NOX pure barre CrossFit 67mm U.S. Auto Enthusiasts HAGERTY.. 9#10The Hagerty Affinity Ecosystem: Driving Engagement and Brand Love 10#11Unparalleled Specialty Insurance for Auto Enthusiasts Data driven value proposition and unparalleled customer service for auto enthusiasts Guaranteed value Compared to stated value with appreciation in car values equaling coverage Greater savings* On average 34% lower than a stated value policy Greater specificity, protection and customer service Reflecting Hagerty's data advantage FORD Added value services for car lovers Roadside service, expert repair network, parts finder specialists and more * Based upon 2021 consumer data collected by Hagerty on single car quotes, with premiums $5000 and under, from daily driver auto insurance carriers."#12Consumer and Partner Focus Unlocks a Growing $12-15B TAM Hagerty's omni-channel strategy allows us to interact with members across three channels Distribution Channels 45% Direct distribution 32% Agency and broker channel 23% National insurance partners 1 Per SNL Financial, by auto premiums written 2 Per Business Insurance Key Stats → State of the art call centers plus digital distribution. → Sales agents in 25 states and 3 countries → Over 45,000 agents → 10 of the top 10 brokers by revenue² → 9 of the top 10 auto insurers including new partners¹ → Top 5 partners each report double-digit growth and segment acceleration Value Proposition → Drives new business flow (insurance & membership) → Enhances service and increases efficiency Deepens relevancy to client → Partner to win → No channel conflict 12#13Win-win for Insurance Carrier Partners Hagerty's partnership focus allows us to methodically grow our membership through indirect channels Total Insurance Solution → Team of passionate experts → Tailored product coverage → Sales & services Compelling Partner Benefits → High intimacy model → Protects their bundle Claims handling → → Underwriting & claims → Pricing → Proprietary technology Launching new partnerships such as Hagerty administering State Farm's Classic+ Program with 480,000+ initial policies beginning in the Fall of 2023 → Valuation tools → Expert repair network We now partner with nine of the top ten auto insurers State FarmⓇ HAGERTY. Never Stop Driving HAGER HAGERTY Ride & Dri Never Stop Driving HAGERTY 11 Never Stop Driving HAGERTY#14Hagerty Delivers Consistent Double-Digit Written Premium Growth Large penetration opportunity given only 4% today, particularly post-1980 enthusiast vehicles Total Percentage Growth Hagerty U.S. Auto Premium Growth vs. Industry Top 100 Hagerty U.S. Auto - CAGR 13.4% Industry Top 100 - CAGR 4.3% 400 300 200 100 O 2010 2011 2012 2013 2014 2015 2016 2017 2018 Sustained Growth 5X the Industry 351% 69% 2019 2020 2021 2022 Collectible vehicles by year Type Pre-1981 Classics Post 1980 Collectibles Total Total Market (cars, mm) 11.3 34.0 ~45.3 Hagerty Penetration 12.1% 1.4% 4.1% 14#15Decades of Underwriting Drives Predictably Low Loss Ratios Under 40% Resulting in an additional 10% contingent underwriting commission (CUC) annually since 2010 Hagerty U.S. Auto Loss Performance vs. Industry Top 100 Total Loss Performance 80 60 60 30 20 2010 Hagerty Loss Ratio - average = 38% Industry Loss Ratio - average = 66% 2013 2014 2015 2016 2017 Til 2020 Stable and Predictable Loss Performance well below Industry Average 501 Multi-dimensional first-party data advantage → Decades of claims data → 40,000 vehicles in Hagerty Valuation Tools → Effective pricing of risk to maintain low loss ratios → Engaging, seamless member experience and cross-selling → Well-positioned to mine the full auto enthusiast TAM 15#16Excellence in Insurance is just the Beginning Hagerty's trusted brand status positions us to monetize our members' passion for cars Insurance is a mandated purchase for nearly every vehicle Most companies just focus on making the process easier and the premiums cheaper. We have designed a better product set using proprietary data Last 4 Years Volve-Sav Feb 2019 $64.33 Flat Market Nov 2019 $62.64 ↑ February 2020 62.55 Current Market Rating Expanding Market Feb 2018 $64.54 Nov 2018 $62.32 ↑ 4:21 HAGERTY Insider Find Your Car's Hagerty Value Year, Make, Model How we build our price guide Upcoming Auctions Mecum Auctions 2 83% ☆ Large, proprietary data sets provide segmentation and pricing advantage. Our products are genuinely appreciated by our members Customer retention of ~90% over the last decade. 16#17Marketplace Platform A $1.6T Collector Vehicle Market, with $1.0T in the US MARKET VALUE TRANSACTION VALUE Source - Company estimates and data as of December 31, 2022 $1.6T in collector vehicles globally (73 million vehicles) $1.0T in U.S. collector vehicles (43M vehicles) $12.5B* on Hagerty's book (300k vehicles) $3B global auctions 17#18Hagerty Marketplace Leverages the Power of the Ecosystem Existing size, scale and trusted brand status position Marketplace for success Auctions Hagerty Time-Based Auctions Buy/Sell Live Auctions Private Sales Hagerty Classifieds Collectors Garage Asset-Based Lending Broad Arrow Capital Leverage Hagerty Valuation Tools, membership, and media content assets to build a comprehensive, trust-based suite of transactional offerings to drive data, revenue and engagement 18#19If Hagerty Drivers Club Cultivates Loyalty and Engagement Ecosystem of 1.3 million paying members. Multiple Points of Engagement I Compelling Advantages I Strong Brand Loyalty Bruce's Buggy Slides On Members enjoy Exclusive automotive offers Ask Hagerty Hagerty Valuation Tools® Hagerty Drivers Club magazine Events and experiences Hagerty Marketplace Emergency services Hagerty Insider And more! Net Promoter Score® Hagerty NPS Industry Avg 83 39 Net Promoter Score (NPS) is a loyalty metric. NPS represents how we are doing in the minds of our clients. HAGERTY Drivers Club Shift Happens 14855 Frank G. $39.000 Boston, MA Q Hagerty Marketplace Mustang De Paracho James F. FL $10.000 19 Sen Diego, CA Buy. Sell. Dream. Drive.#20Hagerty Live Exclusive Interviews HAGERTY Drivers Club OCTANE 101 1 As of November 2022 T CAFFEINE OCTANE SPELD&STYLE 63 312 CAB Thunder Beach FORD Achaine OCTANE Spets Caffeine OCTANE Spacy s Exclusive Premieres D Dream COLLECTIONS Exclusive Series Hagerty Media & Entertainment Multiple, high touch contact points create more engaged customers than TV advertising alone Media 479 M lifetime views Print 2nd Largest automotive magazine by audited circulation. Events 2,500 attended annually Social Media 4.7 M followers on Hagerty channels Owner and operator of 3 of the largest Concours d'Elegance in the U.S. 20#21Hagerty Flywheel 1 2 3 4 5 6 Offer an umatched suite of products and services to enable, validate and fuel the love of cars Overdeliver on enthusiast expectations with world class experiences & H-factor hospitality Drive deeper engagement and adoption of revenue generating products Inspire loyal brand ambassadors who can't live without us Attract new members into our ecosystem with enticing content & experiences Deliver profitable growth to reinvest in new products and services reinvest in our Deliver profitable growth Attract new members offerings 11 Inspire loyal brand ambassadors Offer an umatched suite of products & services Overdeliver on enthusiast expectations Drive deeper engagement 21#22Financial Model E 22#23● ● 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 O O O 2023 Outlook* - Growth and Profitability Strong top-line momentum continuing in 2023 with significantly improved profitability Continue evolution into an Integrated Insurance Business Increase Hagerty Re's quota share reinsurance agreement in the U.S. and U.K. to ~80% O • Significantly improving profitability ($75 million to $85 million in Adjusted EBITDA) through Cost Containment measures and Operational Efficiencies Company outlook from third quarter earnings call on November 8, 2023 23#24Positioned to Deliver Sustained Growth in Written Premiums While growing diversified revenue streams 2018 2019 2020 2021 2022 2023E Marketplace & New partnerships Contractural quota share expansion 2024E Premium revenue Commissions, fees & membership 2025E 24