Investor Slides

2026 Investor Presentation

1. Company Overview

   
   
   

   Our Vision

   Creating a world where loved cars are driven, shared and enjoyed

   
   
   

   "People take good care of their toys."

   Louise Hagerty

   
   
   

   The Leading Brand for Auto Enthusiasts

   Creating an Enthusiast-Centered Ecosystem

   
   
   

   1 Per SNL Financial, by auto premiums written as of FY2024.

   Insurance: Protect

   Custom, specialized insurance

   for enthusiast vehicles

   Marketplace: Buy s Sell

   Trusted marketplace for buying and

   selling classic and collector cars

   Membership: Enjoy

   Affinity program with the world's largest automotive membership community and award-winning content & entertainment

   HAGERTY | 6

   Hagerty Summary Highlights

   Leading specialty insurance provider and automotive brand for the vast collector car enthusiast ecosystem

   Recurring revenue model fueled by unique expertise in underwriting, servicing and monetizing collector cars

   All components of the engine come together to create a powerful flywheel effect resulting in happy customers who view Hagerty as additive to their passion and not simply a commodity

   Underpinned by proprietary database meticulously constructed, cataloged and scrubbed over 40+ years leading to measurable data advantages

   • Highly predictable and stable underwriting economics captured via underwriting entities

   • Commission and fee-based economics earned in an MGA capacity

   • Membership, marketplace and other economics from Hagerty Drivers Club (HDC) subscriptions, auto auctions, private sales, online marketplaces, events, collector car lending and more

   GROWTH AND RETENTION

   $1,456M

   2025Y Total Revenue

   +17% from 2024Y

   88.7%

   2025Y

   Policy Retention

   >80

   5 Year Net Promoter Score1

   PROFITABILITY

   39.3%

   2025Y

   Loss Ratio2

   $149M

   10%3

   2025Y Net Income

   +91% YOY

   $237M

   16%3

   2025Y Adj. EBITDA4

   +46% YOY

   Note: Statistics shown LTM for the period ended December 31, 2025.

   1 NPS is measured twice annually through a web-based survey sent by email invitation to a random sample of existing HDC Members and is reported annually using an average of the two surveys.

   2 Hagerty Re Loss Ratio is the ratio of (i) Hagerty Re's losses and loss adjustment expenses to (ii) its earned premium.

   3 Net income margin and adjusted EBITDA margin, respectively.

   4 Non-GAAP financial measure. Please see the appendix for a reconciliation to most applicable GAAP metric.

   Unique Ecosystem to Authentically Engage with Passionate Enthusiasts

   Membership

   Suite of Products and Services Help Enthusiasts

   Protect, Buy, Sell, and Enjoy…

   Driving Engagement Across Every Mile of the Hagerty Experience - Our "Secret Sauce"

   .. While Constant Engagement Helps Build the Brand and Feed the Hagerty Insurance Engine
   data collection

   • Authentic interaction with customers and policyholders - not just at insurance renewal

   • Allows insurance business to flourish

   • Ability to reach all collector car enthusiasts

   • Source of vast amount of

   • Outsized new customer growth

   • Excellent customer retention and NPS

   • Decreased Customer Acquisition Cost

   • Improved underwriting

   • Earnings diversification

   • Differentiated means of competing in insurance

   
   
   

   479M lifetime views and

   4.7M followers

Media and Events

Marketplace

HAGERTY | 8

Compelling Financial Profile

$G07

$1,044

$1,000

$1,200

$1,456

$1,1G4

$237

2023 2024 2025 2023 2024 2025

$88

$124

2023 2024 2025

CAT Non-CAT

41.5% 46.4% 3G.3%

1.2% 5.6% 2.4%

2023 2024 2025

38%

25%

34%

$14G

$78

$28

2023 2024 2025

2023 2024 2025

1 Non-GAAP financial measure. Please see the appendix for a reconciliation to most applicable GAAP metric.

2 Total Written Premium is the total amount of insurance premium written by our MGA subsidiaries on behalf of insurance carrier partners during the period.

3 Hagerty Re Loss Ratio is the ratio of (i) Hagerty Re's losses and loss adjustment expenses to (ii) its earned premium.

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1. Investment Highlights

   
   
   Why Hagerty

   • Visionary, founder-led leadership team with deep insurance

     expertise and diverse backgrounds

   • Attractive combination of

     1. Retained underwriting economics

     2. Commission and fee-based MGA revenue

     3. And synergistic membership, marketplace and other revenue

   • Robust and diversified omni-channel distribution

   • State Farm partnership and Enthusiast+ product spring-loaded to sustain high rates of profitable growth

   • Large and underpenetrated target market with deep fragmentation

   • Advanced data collection will be augmented by recent technology investments

   • Risk bearing entity producing strong returns with a robust and conservative balance sheet

High Quality Leadership Team

McKeel Hagerty

Chief Executive Officer & Chairman of the Board

Mark Elliott

Chief Investment Officer

Patrick McClymont

Chief Financial Officer

Kenneth Ahn

President of Marketplace

Collette Champagne

Chief HR Officer & Chief Administrative Officer

Jeff Briglia

President of Insurance

Russell (Russ) Page

Chief Information Officer

Jay Koval

SVP of Investor Relations and Communications

Diana Chafey

Chief Legal Officer

Marc Burns

SVP of Brand and Marketing

Diversified Sources of Revenue

Total Revenue ($M)

1 Includes base commissions, payment plan fees and contingent underwriting commissions.

2 Quota share percentages by geographic area for the year ended December 31, 2025, were 81% for core U.S. business, 50% in Canada, and 80% in the U.K. Hagerty Re is no longer reinsuring the risks underwritten by its U.K. MGA affiliate as of 1/1/2024, and the book is in run-off. Hagerty began assuming 100% of the risk in the U.S. book starting on January 1, 2026 as more fully described on page 21.

HAGERTY | 13

•

Earned

Premium

Earned portion of written premiums

that Hagerty Re has assumed under ~80%2 quota share reinsurance agreements with carrier partners

•

Commission

and Fees

Gross commissions and fees

earned from the underwriting, sale and servicing of insurance policies written on behalf of carriers, prior to any offsetting ceding commission expense

Membership

and Other &

Marketplace

• Revenue primarily earned through HDC subscriptions, auto auctions,

private sales, online marketplaces, industry-leading events, collector car lending, media and more

Omni-Channel Distribution Network Unlocks Target Market

Direct Distribution Channel

Value proposition: Belonging, camaraderie,

45% 55% Partnership Channel

AGENCY & BROKER PARTNERS

32%

understanding, admiration, joy

• Membership model drives significant percentage

  of new business flow

• Promotes brand awareness

  Value proposition: Enhance service, increase efficiency

• Over 50,000 agents

• 10 of the top 10 brokers by revenue1

  NATIONAL INSURANCE PARTNERS

  Value proposition: Enhance service, true partner, no channel conflict

  • 9 of the top 10 largest auto insurers2

    23%

  • 4 of our top 5 partners report double digit growth

  • Recent new partnerships

REPRESENTATIVE PARTNERS

1 Per Business Insurance.

2 Per SNL Financial, by auto premiums written as of FY2024.

Durable and Consistent Mid-Teens Growth

3.0

2.5

2.0

1.5

1.0

0.5

Hagerty PIF Count(M)

Hagerty vs. Industry Top 1001 Total

U.S. Auto Written Premium Growth

700%

600%

500%

400%

300%

200%

100%

Hagerty vs. Peers 2020-2025 Median Total Revenue Growth2

25%

23%

16%

3.0M PIF count goal by 2030

0.0

Note: All premium amounts shown for Hagerty reflect total written premium.

0%

HGTY U.S. Auto Industry Top 100

Specialty P&C3

Brokers 4

1Industry Top 100 represents the top 100 U.S. P&C insurers with a private auto LOB. 2 Source: Company filings. 3 Specialty P&C peers include BOW, KNSL, PGR, PLMR, RLI, SKWD, and WRB.

4Brokers peers include AJG, AON, BRO, BWIN, GSHD, MMC, NP, RYAN, TWFG, and WTW.

HAGERTY | 15

Decades of Underwriting Drive Predictably Low Loss Ratios

Hagerty MGA delivers consistent, high quality written premium growth

Multi-dimensional first-party data advantage

→ Superior value proposition and innovative partnerships

→ Engaging, seamless member experience and cross-selling

→ Decades of claims data with 40,000 distinct makes/models in Hagerty Valuation Tools

→ Effective pricing of risk to maintain low loss ratios

Near and Medium-Term Initiatives at Inflection Point

• Distribution relationship since 2022; agreement in place through 2030

  
  
  

• Alignment of interest via State Farm ~15% stake in Hagerty

• 525k+ existing State Farm collector car policies moving to Hagerty platform by 2027

• State Farm agents selling new policies in 27 states; expect to be selling in majority of US by YE 2026

• 100% MGA-based economic arrangement

Enthusiast+ Program

• Broadening underwriting appetite and addressable market

  • Distinct pricing and leading product features

  • Natural evolution of risk appetite and business model

  • Initial launch in 3Q'25; full rollout in the United States in next 3-4 years

  • Opportunity to leverage onshore insurance carrier, Drivers Edge

• Designed to target more modern enthusiast vehicles that are inherently more drivable

HAGERTY | 17

Well Positioned to Capture Additional Market Share

Niche, but large and underpenetrated, target market

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 Vehicles in force as of December 31, 2025.

Technology and Data Driving Superior Results

Industry-Leading Valuation Tool Powering Hagerty's Ecosystem Today

HISTORICAL DATA COLLECTION

CURRENT TECHNOLOGY AND DATA

FUTURE AREAS OF EXPANSION

HAGERTY | 19

Underwriting Snapshot

• Our risk-bearing entity assumes risk from our capacity partners via quota share reinsurance

  • Core U.S. = 80% moving to 100%1

  • Canada = 50%

  • Steady increase in assumed premium over time given profitability of the book

• Track record of industry-leading consistent and stable loss ratios

  • 3Y average loss ratio of 43% vs. ~75% industry average

• Fundamentally different risk profile vs. daily driving auto insurance

• Diversified high-quality investment portfolio with 95% comprised of investment grade fixed maturity securities as of 4Q'25

• Prudently booked reserves

$1,1G4M

2025

Net Written Premium

1G5%

12/31/2025

BSCR2

3G.3%

2025

Loss Ratio

$382M

12/31/25

Capital3

$727M

2025

Net Earned Premium

~34%

2025 Return on Equity

86.6%

2025 Combined Ratio

A-

A.M. Best FSR

Positive

1 Hagerty will assume 100% of the risk in the U.S. book starting on January 1, 2026. 2 Bermuda Solvency Capital Requirement. 3 Represents Hagerty Re equity of $357 plus the State Farm loan of $25M that is treated as debt per GAAP however received favorable capital treatment from A.M. Best and has received approval from the Bermuda Monetary Authority to be recorded as Other Fixed Capital on the Statutory Statement of Capital and Surplus and as Tier 2 Ancillary Capital.

HAGERTY | 20