HGTY / Hagerty, Inc. - Pengajuan SECLaporan Tahunan, Pernyataan Proksi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 August 7, 2025 Date of Report (date of earliest event reported) HAGERTY, INC. (Exac

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 August 7, 2025 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commis

Hagerty, Inc. 9,700,000 Shares of Class A Common Stock Underwriting Agreement August 7, 2025

EX-1.1 Exhibit 1.1 Hagerty, Inc. 9,700,000 Shares of Class A Common Stock Underwriting Agreement August 7, 2025 Keefe, Bruyette & Woods, Inc. J.P. Morgan Securities LLC As Representatives of the several Underwriters listed in Schedule 1 hereto c/o Keefe, Bruyette & Woods, Inc. 787 Seventh Avenue, 4th Floor New York, NY 10019 c/o J.P. Morgan Securities LLC 383 Madison Avenue New York, NY 10179 Ladi

Hagerty Announces Pricing of its Upsized Secondary Offering of Class A Common Stock

EX-99.1 Exhibit 99.1 For Immediate Release Hagerty Announces Pricing of its Upsized Secondary Offering of Class A Common Stock TRAVERSE CITY, Michigan, August 7, 2025 /PRNewswire/ – Hagerty, Inc. (NYSE: HGTY) (“Hagerty”), an automotive enthusiast brand and leading specialty vehicle insurance provider, announced the pricing of its secondary offering, upsized to 9,700,000 shares of Hagerty’s Class A

9,700,000 Shares Hagerty, Inc. Class A Common Stock

424B7 Table of Contents Filed Pursuant to Rule 424(b)(7) Registration File No. 333-261810 PROSPECTUS SUPPLEMENT (To Prospectus dated February 7, 2023) 9,700,000 Shares Hagerty, Inc. Class A Common Stock The selling stockholders named in this prospectus supplement, Hagerty Holding Corp. (“HHC”) and Aldel LLC (“Aldel LLC”), are offering a total of 9,700,000 shares of our Class A common stock, par va

Hagerty Announces Secondary Offering of its Class A Common Stock

EX-99.1 Exhibit 99.1 For Immediate Release Hagerty Announces Secondary Offering of its Class A Common Stock TRAVERSE CITY, Michigan, August 6, 2025 /PRNewswire/ – Hagerty, Inc. (NYSE: HGTY) (“Hagerty”), an automotive enthusiast brand and leading specialty vehicle insurance provider, announced that Hagerty Holding Corp. (“HHC”) and Aldel LLC (“Aldel” and together with HHC, the “Selling Stockholders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 August 6, 2025 Date of Report (date of earliest event reported) HAGERTY, INC. (Exac

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 August 6, 2025 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commis

Subject to Completion, Dated August 6, 2025 8,700,000 Shares Hagerty, Inc. Class A Common Stock

424B7 Table of Contents Filed Pursuant to Rule 424(b)(7) Registration File No. 333-261810 The information in this preliminary prospectus supplement is not complete and may be changed. This preliminary prospectus supplement and the accompanying prospectus are not an offer to sell nor do they seek an offer to buy these securities in any jurisdiction where the offer or sale is not permitted. Subject

Investor Presentation Q2 2025 SPEAKERS: McKeel Hagerty | Chief Executive Officer and Chairman Patrick McClymont | Chief Financial Officer HAGERTY Q2 2025 | 2 FORWARD LOOKING STATEMENTS / NON-GAAP FINANCIAL MEASURES This presentation contains statemen

a25-q2xinvestorxdeck08x0 Investor Presentation Q2 2025 SPEAKERS: McKeel Hagerty | Chief Executive Officer and Chairman Patrick McClymont | Chief Financial Officer HAGERTY Q2 2025 | 2 FORWARD LOOKING STATEMENTS / NON-GAAP FINANCIAL MEASURES This presentation contains statements that constitute “forward-looking statements” within the meaning of the federal securities laws.

Stockholder Letter Q2 2025 HAGERTY Q2 2025 | 2 Summer driving season is the best time to be a classic car owner. Top down, windows open, music up, chrome gleaming — these are the simple joys that ignite a lifelong love affair with automobiles. For th

a25-q2stockholderletter0 Stockholder Letter Q2 2025 HAGERTY Q2 2025 | 2 Summer driving season is the best time to be a classic car owner.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-40244 HAGERTY, I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 August 4, 2025 Date of Report (date of earliest event reported) HAGERTY, INC. (Exac

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 August 4, 2025 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commis

Hagerty Reports Second Quarter 2025 Results Increases 2025 Outlook for Revenue and Profit Growth

For Immediate Release Hagerty Reports Second Quarter 2025 Results Increases 2025 Outlook for Revenue and Profit Growth •The Company increased its full year 2025 outlook for Total Revenue growth to 13-14%, Net Income growth of 43-53%, and Adjusted EBITDA growth of 30-38% •Second quarter 2025 Total Revenue increased 18% year-over-year to $368.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 July 24, 2025 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 July 24, 2025 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commiss

Hagerty Announces LOI for New Fronting Arrangement with Markel; Hagerty Re to Assume 100% of the Premium

For Immediate Release Hagerty Announces LOI for New Fronting Arrangement with Markel; Hagerty Re to Assume 100% of the Premium TRAVERSE CITY, Michigan, July 24, 2025 – Hagerty, Inc.

Hagerty, Inc. Up to 251,033,906 Shares of Class A Common Stock Issuable Upon Exchange of Class V Common Stock and OpCo Units Up to 20,005,550 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Up to 339,121,956 Shares of Class A Common

Filed Pursuant to Rule 424(b)(7) Registration File No. 333-261810 PROSPECTUS SUPPLEMENT NO. 1 (To Prospectus dated February 7, 2023) Hagerty, Inc. Up to 251,033,906 Shares of Class A Common Stock Issuable Upon Exchange of Class V Common Stock and OpCo Units Up to 20,005,550 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Up to 339,121,956 Shares of Class A Common Stock Offered by

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 3, 2025 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 3, 2025 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commissi

Stockholder Letter Q1 2025 HAGERTY Q1 2025 | 2 Spring is upon us, and with it comes the joyful sound of classic engines roaring to life after a long winter’s rest. As enthusiasts across the country begin planning their first drives of the season, it

Stockholder Letter Q1 2025 HAGERTY Q1 2025 | 2 Spring is upon us, and with it comes the joyful sound of classic engines roaring to life after a long winter’s rest.

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 7, 2025 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commissio

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-40244 HAGERTY,

Investor Presentation Q1 2025 SPEAKERS: McKeel Hagerty | Chief Executive Officer and Chairman Patrick McClymont | Chief Financial Officer HAGERTY Q1 2025 | 2 FORWARD LOOKING STATEMENTS / NON-GAAP FINANCIAL MEASURES This presentation contains statemen

Investor Presentation Q1 2025 SPEAKERS: McKeel Hagerty | Chief Executive Officer and Chairman Patrick McClymont | Chief Financial Officer HAGERTY Q1 2025 | 2 FORWARD LOOKING STATEMENTS / NON-GAAP FINANCIAL MEASURES This presentation contains statements that constitute “forward-looking statements” within the meaning of the federal securities laws.

Hagerty Reports First Quarter 2025 Results Reaffirms 2025 Outlook for Revenue and Profit Growth

For Immediate Release Hagerty Reports First Quarter 2025 Results Reaffirms 2025 Outlook for Revenue and Profit Growth •First quarter 2025 Total Revenue increased 18% year-over-year to $319.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the app

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy State

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the app

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy State

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 April 16, 2025 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commis

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 March 7, 2025 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commiss

Credit Agreement, dated as of March 7, 2025, among The Hagerty Group, LLC, the Foreign Subsidiary Borrowers party hereto, the Lenders party hereto, and JPMorgan Chase Bank, N.A., as Administrative Agent,

Exhibit 10.1 Material indicated with a “[***]” has been omitted from this exhibit because it is both (i) not material and (ii) would likely cause competitive harm to the Company if publicly disclosed. Execution Version CREDIT AGREEMENT dated as of March 7, 2025 among THE HAGERTY GROUP, LLC, THE FOREIGN SUBSIDIARY BORROWERS PARTY HERETO, THE LENDERS PARTY HERETO, JPMORGAN CHASE BANK, N.A., as Admin

Description of Registrant's Securities, filed herewith.

Exhibit 4.1 DESCRIPTION OF SECURITIES The following description of the securities of Hagerty, Inc. (“we,” “our,” “us,” “Hagerty,” “HGTY,” and the “Company”) is a summary and does not purport to be complete. It is subject to, and qualified in its entirety by reference to, our Third Amended and Restated Certificate of Incorporation (“Amended and Restated Charter”), our Amended and Restated Bylaws (“

Subsidiaries of the Company, filed herewith.

Exhibit 21.1 Name State or Other Jurisdiction of Incorporation Doing Business As The Hagerty Group, LLC Delaware Hagerty Asset Management, LLC Michigan Hagerty International Holdings Limited United Kingdom Classic Car Analytics GMBH Germany Hagerty International Limited United Kingdom Hagerty Enthusiast Limited United Kingdom Hagerty Insurance Agency, LLC Delaware Hagerty Canada, LLC Delaware Hage

Stockholder Letter Q4 2024 HAGERTY Q4 2024 | 2 Hagerty joined the New York Stock Exchange as a publicly listed company three years ago in December. What a ride it has been, almost doubling our revenue from 2021 to $1.2 billion as we have added 767,00

Stockholder Letter Q4 2024 HAGERTY Q4 2024 | 2 Hagerty joined the New York Stock Exchange as a publicly listed company three years ago in December.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-40

HAGERTY Q4 2024 | 3 2024 OUTLOOK (AS OF 3/12/24)* 2024 RESULTS Total Revenue Growth 15% - 17% +20% Written Premium Growth 13% - 14% +15% Significantly improve profitability1: Net Income $61M - $70M $78M (+178%) Adjusted EBITDA2 $124M - $135M $124M (+

HAGERTY Q4 2024 | 3 2024 OUTLOOK (AS OF 3/12/24)* 2024 RESULTS Total Revenue Growth 15% - 17% +20% Written Premium Growth 13% - 14% +15% Significantly improve profitability1: Net Income $61M - $70M $78M (+178%) Adjusted EBITDA2 $124M - $135M $124M (+41%) * Hagerty shared the initial 2024 Outlook on the fourth quarter 2023 earnings call on March 12, 2024.

Hagerty Insider Trading Policy, dated December 13, 2024, filed herewith.

Hagerty Insider Trading Policy Date 12/13/2024 Document Properties Property Description Distribution Info Classification Public Document Owner Chief Legal Officer Effective Date 12/13/2024 As a public company, Hagerty, Inc.

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 March 4, 2025 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commiss

Hagerty Reports Full Year 2024 Results Provides 2025 Outlook for Revenue and Profit Growth

For Immediate Release Hagerty Reports Full Year 2024 Results Provides 2025 Outlook for Revenue and Profit Growth •Full year 2024 Total Revenue increased 20% year-over-year to $1.

HGTY / Hagerty, Inc. / Polar Capital Holdings Plc Passive Investment

SC 13G 1 polar-hgty093024.htm UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* HAGERTY, INC. (Name of Issuer) Class A common stock, par value $0.0001 per share (Title of Class of Securities) 405166109 (CUSIP Number) September 30, 2024 (Date of Event Which Requires Filing of this Statement) Check the appro

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 7, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Ex

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 7, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Comm

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-40244 HAGER

Stockholder Letter Q3 2024 HAGERTY Q3 2024 | 2 November is when collectors in many parts of the country begin winterizing their beloved vintage cars, trucks, and motorcycles. There is detailing to be done, oil to be changed, batteries to be removed,

Stockholder Letter Q3 2024 HAGERTY Q3 2024 | 2 November is when collectors in many parts of the country begin winterizing their beloved vintage cars, trucks, and motorcycles.

88.8% Adjusted EBITDA2 $19 $19 $24 $24 $37 $(10) Q3 2022 Q3 2022Q3 2023 Q3 2023Q3 2024 Q3 2024 $78 $105 $-- $35 $70 $19 HAGERTY Q3 2024 | 10 IN THOUSANDS 2023 RESULTS PRIOR 2024 OUTLOOK2 REVISED 2024 OUTLOOK Total Written Premium $907,175 $1,034,000

investordeckq32024final 88.8% Adjusted EBITDA2 $19 $19 $24 $24 $37 $(10) Q3 2022 Q3 2022Q3 2023 Q3 2023Q3 2024 Q3 2024 $78 $105 $- $35 $70 $19 HAGERTY Q3 2024 | 10 IN THOUSANDS 2023 RESULTS PRIOR 2024 OUTLOOK2 REVISED 2024 OUTLOOK Total Written Premium $907,175 $1,034,000 - $1,043,000 $1,043,000 - $1,043,000 Total Revenue $1,000,213 $1,160,000 - $1,180,000 $1,180,000 - $1,190,000 Net Income3 $28,1

Hagerty Reports Third Quarter 2024 Results Updates 2024 Outlook for Revenue and Profit Growth

For Immediate Release Hagerty Reports Third Quarter 2024 Results Updates 2024 Outlook for Revenue and Profit Growth •Third quarter 2024 Total Revenue increased 17% year-over-year to $323.

Separation and Release of Claims Agreement, dated November 4, 2024, by and between Paul Rehrig and Hagerty Insurance Agency, LLC, filed herewith.

Exhibit 10.3 CONFIDENTIAL EMPLOYEE SEPARATION AND RELEASE OF CLAIMS AGREEMENT This Separation and Release of Claims Agreement ("Agreement") is entered into by and between Hagerty Insurance Agency, LLC, a Delaware limited liability company, (the "Employer"), on behalf of itself, its parents, subsidiaries, and other corporate affiliates, and each of their respective present and former employees, off

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 September 1, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Com

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-40244 HAGERTY, I

Stockholder Letter Q2 2024 HAGERTY Q2 2024 | 2 August is a golden time for collectible car lovers. The breezes are warm. Curvy roads beckon. There are car shows and auctions in abundance. Hagerty is built for these moments. With these quarterly lette

Stockholder Letter Q2 2024 HAGERTY Q2 2024 | 2 August is a golden time for collectible car lovers.

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 August 6, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commis

Form of Restricted Stock Unit Award Agreement pursuant to the Hagerty, Inc. 2021 Stock Incentive Plan (incorporated by reference to Exhibit 10.3 of the Company

Exhibit 10.3 RESTRICTED STOCK UNIT AWARD AGREEMENT PURSUANT TO THE HAGERTY, INC. 2021 STOCK INCENTIVE PLAN * * * * * Participant: #ParticipantName# Grant Date: #GrantDate# Number of Restricted Stock Units Granted Pursuant to this Agreement: #QuantityGranted# * * * * * THIS RESTRICTED STOCK UNIT AWARD AGREEMENT (this “Agreement”), dated as of the Grant Date specified above, is entered into by and b

Investor Presentation Q2 2024 SPEAKERS: McKeel Hagerty | Chief Executive Officer and Chairman Patrick McClymont | Chief Financial Officer HAGERTY Q2 2024 | 2 FORWARD LOOKING STATEMENTS / NON-GAAP FINANCIAL MEASURES This presentation contains statemen

Investor Presentation Q2 2024 SPEAKERS: McKeel Hagerty | Chief Executive Officer and Chairman Patrick McClymont | Chief Financial Officer HAGERTY Q2 2024 | 2 FORWARD 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.

Hagerty Reports Second Quarter 2024 Results Increases 2024 Outlook for Revenue and Profit Growth

For Immediate Release Hagerty Reports Second Quarter 2024 Results Increases 2024 Outlook for Revenue and Profit Growth •Second quarter 2024 Total Revenue increased 20% year-over-year to $313.

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 July 25, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commiss

EX-99.25

NOTIFICATION OF THE REMOVAL FROM LISTING AND REGISTRATION OF THE STATED SECURITIES The New York Stock Exchange hereby notifies the SEC of its intention to remove the entire class of the stated securities from listing and registration on the Exchange at the opening of business on August 02, 2024, pursuant to the provisions of Rule 12d2-2 (a).

HGTY / Hagerty, Inc. / STATE FARM MUTUAL AUTOMOBILE INSURANCE CO - SC 13D/A Activist Investment

SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 5) HAGERTY, INC. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 405166109 (CUSIP Number) Matthew D. Melick State Farm Mutual Automobile Insurance Company One State Farm Plaza Bloomington, IL 61710 (

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 July 9, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commissi

Hagerty Names Insurance Veteran Anthony J. Kuczinski to Hagerty’s Board of Directors

Exhibit 99.1 Hagerty Names Insurance Veteran Anthony J. Kuczinski to Hagerty’s Board of Directors TRAVERSE CITY, Mich., July 9, 2024 – Hagerty, Inc., (NYSE: HGTY) an automotive enthusiast brand and a leading specialty vehicle insurance provider, announced today that Anthony (Tony) J. Kuczinski, former Chief Executive Officer of Munich Reinsurance US Holdings (Munich Re US), will join Hagerty’s Boa

HGTY / Hagerty, Inc. / MARKEL CORP - SC 13D/A Activist Investment

SC 13D/A 1 ef20032165sc13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 2)* Hagerty, Inc. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 405166109 (CUSIP Number) Richard R. Grinnan Senior Vice President, Chief Legal Officer and Secretary

Amendment No. 1 to Warrant Agreement, dated July 3, 2024 , by and between the Company and Continental Stock Transfer & Trust Company (incorporated by reference to Exhibit 10.2 of the Company's Form 8-K (File No. 001-40244), filed with the SEC on July 5, 2024).

Exhibit 10.2 AMENDMENT NO. 1 TO WARRANT AGREEMENT THIS AMENDMENT NO. 1 TO WARRANT AGREEMENT (this “Amendment”), dated as of July 3, 2024, is made by and between Hagerty, Inc., a Delaware corporation (f/k/a Aldel Financial Inc.) (the “Company”), and Continental Stock Transfer & Trust Company, a New York corporation (the “Warrant Agent”), and constitutes an amendment to that certain Warrant Agreemen

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 July 3, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 July 3, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commissi

Hagerty Announces Expiration and Results of Warrant Exchange Offer and Consent Solicitation

Exhibit 99.1 Hagerty Announces Expiration and Results of Warrant Exchange Offer and Consent Solicitation TRAVERSE CITY, Mich., July 3, 2024 /PRNewswire/ – Hagerty, Inc. (NYSE: HGTY) (the “Company” or “Hagerty”), an automotive enthusiast brand and leading specialty vehicle insurance provider, announced today the expiration and results of its previously announced exchange offer (the “Offer”) and con

, by and between the Company and Continental Stock Transfer & Trust Company.

Exhibit 10.1 AMENDMENT NO. 1 TO WARRANT AGREEMENT THIS AMENDMENT NO. 1 TO WARRANT AGREEMENT (this “Amendment”), dated as of July 3, 2024, is made by and between Hagerty, Inc., a Delaware corporation (f/k/a Aldel Financial Inc.) (the “Company”), and Continental Stock Transfer & Trust Company, a New York corporation (the “Warrant Agent”), and constitutes an amendment to that certain Warrant Agreemen

Hagerty Announces Expiration and Results of Warrant Exchange Offer and Consent Solicitation

Exhibit 99.1 Hagerty Announces Expiration and Results of Warrant Exchange Offer and Consent Solicitation TRAVERSE CITY, Mich., July 3, 2024 /PRNewswire/ – Hagerty, Inc. (NYSE: HGTY) (the “Company” or “Hagerty”), an automotive enthusiast brand and leading specialty vehicle insurance provider, announced today the expiration and results of its previously announced exchange offer (the “Offer”) and con

Entry into a Material Definitive Agreement, Material Modification to Rights of Security Holders, Financial Statements and Exhibits, Other Events, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 July 3, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commissi

, by and between the Company and Continental Stock Transfer & Trust Company.

Exhibit 10.2 AMENDMENT NO. 1 TO WARRANT AGREEMENT THIS AMENDMENT NO. 1 TO WARRANT AGREEMENT (this “Amendment”), dated as of July 3, 2024, is made by and between Hagerty, Inc., a Delaware corporation (f/k/a Aldel Financial Inc.) (the “Company”), and Continental Stock Transfer & Trust Company, a New York corporation (the “Warrant Agent”), and constitutes an amendment to that certain Warrant Agreemen

, by and between the Company and Continental Stock Transfer & Trust Company.

Exhibit 10.1 AMENDMENT NO. 1 TO WARRANT AGREEMENT THIS AMENDMENT NO. 1 TO WARRANT AGREEMENT (this “Amendment”), dated as of July 3, 2024, is made by and between Hagerty, Inc., a Delaware corporation (f/k/a Aldel Financial Inc.) (the “Company”), and Continental Stock Transfer & Trust Company, a New York corporation (the “Warrant Agent”), and constitutes an amendment to that certain Warrant Agreemen

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 (AMENDMENT NO. 1) HAGERTY, INC. (Name of Subject Company and Filing P

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 (AMENDMENT NO. 1) HAGERTY, INC. (Name of Subject Company and Filing Person (Issuer)) Warrants to Acquire Shares of Class A Common Stock 405166117 Warrants to Acquire Shares of Class A Common Stock 405166125 (Title of Cl

PROSPECTUS/OFFER TO EXCHANGE Offer to Exchange Warrants to Acquire Shares of Class A Common Stock Hagerty, Inc. Shares of Class A Common Stock Hagerty, Inc. Consent Solicitation THE OFFER PERIOD (AS DEFINED BELOW) AND WITHDRAWAL RIGHTS WILL EXPIRE ON

Filed Pursuant to Rule 424(b)(3) Registration No. 333-279919 PROSPECTUS/OFFER TO EXCHANGE Offer to Exchange Warrants to Acquire Shares of Class A Common Stock of Hagerty, Inc. for Shares of Class A Common Stock of Hagerty, Inc. and Consent Solicitation THE OFFER PERIOD (AS DEFINED BELOW) AND WITHDRAWAL RIGHTS WILL EXPIRE ONE MINUTE AFTER 11:59 P.M., EASTERN TIME, ON JULY 2, 2024, OR SUCH LATER TIM

* * * *

DLA Piper LLP (US) 2525 East Camelback Road Suite 1000 Phoenix, AZ 85016 www.dlapiper.com Kevin Criddle [email protected] T 480 606 5129 June 12, 2024 Via Edgar U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street, NE Washington, D.C. 20549 Attention: David Duchovny Re: Hagerty, Inc. SC TO-I filed June 3, 2024 File No. 005-92476 Registration Statement on

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 4, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commissi

HGTY / Hagerty, Inc. / STATE FARM MUTUAL AUTOMOBILE INSURANCE CO - SC 13D/A Activist Investment

SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 4) HAGERTY, INC. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 405166109 (CUSIP Number) Matthew D. Melick State Farm Mutual Automobile Insurance Company One State Farm Plaza Bloomington, IL 61710 (

Filing Fee Table.

Filing Fee Exhibit Calculation of Filing Fee Table SC TO-I (Form Type) Hagerty, Inc.

Form of Notice of Guaranteed Delivery.

Exhibit 99.2 NOTICE OF GUARANTEED DELIVERY OF WARRANTS OF HAGERTY, INC. Pursuant to the Prospectus/Offer to Exchange, dated June 3, 2024 Instructions for Use Unless defined herein, terms used in this notice of guaranteed delivery (this “Notice of Guaranteed Delivery”) shall have the definitions set forth in the prospectus/offer to exchange, dated June 3, 2024 (as amended or supplemented from time

Form of Letter to Brokers, Dealers, Commercial Banks, Trust Companies, and Other Nominees (incorporated by reference to Exhibit 99.3 to the Company’s Registration Statement on Form S-4, filed with the SEC on

Exhibit 99.3 LETTER TO BROKERS, DEALERS, COMMERCIAL BANKS, TRUST COMPANIES AND OTHER NOMINEES Offer To Exchange Warrants to Acquire Shares of Class A Common Stock of Hagerty, Inc. for Shares of Class A Common Stock of Hagerty, Inc. and Consent Solicitation THE OFFER AND CONSENT SOLICITATION (AS DEFINED BELOW) AND WITHDRAWAL RIGHTS WILL EXPIRE AT ONE MINUTE AFTER 11:59 P.M., EASTERN TIME, ON JULY 2

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 3, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commissi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 3, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 3, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commissi

Form of Letter to Clients of Brokers, Dealers, Commercial Banks, Trust Companies, and Other Nominees (incorporated by reference to Exhibit 99.4 to the Company’s Registration Statement on Form S-4, filed with the SEC on

Exhibit 99.4 LETTER TO CLIENTS OF BROKERS, DEALERS, COMMERCIAL BANKS, TRUST COMPANIES AND OTHER NOMINEES Offer To Exchange Warrants to Acquire Shares of Class A Common Stock of Hagerty, Inc. for Shares of Class A Common Stock of Hagerty, Inc. and Consent Solicitation THE OFFER AND CONSENT SOLICITATION (AS DEFINED BELOW) AND WITHDRAWAL RIGHTS WILL EXPIRE AT ONE MINUTE AFTER 11:59 P.M., EASTERN TIME

Filing Fee Table.

Exhibit 107 Calculation of Filing Fee Tables Form S-4 (Form Type) Hagerty, Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered and Carry Forward Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule(1) Amount Registered(2) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Car

, 2024, by and among Hagerty, Inc. and the Holders party thereto.

Exhibit 10.37 TENDER AND SUPPORT AGREEMENT This Tender and Support Agreement (this “Agreement”), dated as of June 3, 2024, is entered into by and among Hagerty, Inc., a Delaware corporation (the “Company”), each of the persons listed on Schedule A hereto (each, a “Public Warrant Holder”), each of the persons listed on Schedule B hereto (each, a “PIPE Warrant Holder”), each of the persons listed on

As filed with the Securities and Exchange Commission on June 3, 2024

As filed with the Securities and Exchange Commission on June 3, 2024 Registration Statement No.

Form of Letter of Transmittal and Consent (incorporated by reference to Exhibit 99.1 to the Company’s Registration Statement on Form S-4, filed with the SEC on

Exhibit 99.1 LETTER OF TRANSMITTAL AND CONSENT Offer To Exchange Warrants to Acquire Shares of Class A Common Stock of Hagerty, Inc. for Shares of Class A Common Stock of Hagerty, Inc. and Consent Solicitation THE OFFER AND CONSENT SOLICITATION (AS DEFINED BELOW) AND WITHDRAWAL RIGHTS WILL EXPIRE AT ONE MINUTE AFTER 11:59 P.M., EASTERN TIME, ON JULY 2, 2024, OR SUCH LATER TIME AND DATE TO WHICH TH

, 2024, by and among Hagerty, Inc. and the warrant holders party thereto.

Exhibit (d)(xlvi) TENDER AND SUPPORT AGREEMENT This Tender and Support Agreement (this “Agreement”), dated as of June 3, 2024, is entered into by and among Hagerty, Inc.

Hagerty Commences Warrant Exchange Offer and Consent Solicitation

Exhibit 99.1 Hagerty Commences Warrant Exchange Offer and Consent Solicitation TRAVERSE CITY, Mich., June 3, 2024 /PRNewswire/ – Hagerty, Inc. (NYSE: HGTY) (the “Company” or “Hagerty”), an automotive enthusiast brand and leading specialty vehicle insurance provider, announced today that it has commenced an exchange offer (the “Offer”) and consent solicitation (the “Consent Solicitation”) relating

Hagerty Commences Warrant Exchange Offer and Consent Solicitation

Exhibit 99.1 Hagerty Commences Warrant Exchange Offer and Consent Solicitation TRAVERSE CITY, Mich., June 3, 2024 /PRNewswire/ – Hagerty, Inc. (NYSE: HGTY) (the “Company” or “Hagerty”), an automotive enthusiast brand and leading specialty vehicle insurance provider, announced today that it has commenced an exchange offer (the “Offer”) and consent solicitation (the “Consent Solicitation”) relating

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 HAGERTY, INC. (Name of Subject Company and Filing Person (Issuer))

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO TENDER OFFER STATEMENT UNDER SECTION 14(d)(1) OR 13(e)(1) OF THE SECURITIES EXCHANGE ACT OF 1934 HAGERTY, INC. (Name of Subject Company and Filing Person (Issuer)) Warrants to Acquire Shares of Class A Common Stock 405166117 Warrants to Acquire Shares of Class A Common Stock 405166125 (Title of Class of Securities)

effective as of July 1, 2024, by and between the Company and Jeff Briglia (incorporated

Exhibit 10.2 EMPLOYMENT AGREEMENT THIS EMPLOYMENT AGREEMENT (“Agreement”) is hereby entered into by and between HAGERTY, INC., a Delaware corporation (“Company”) and JEFFREY E. BRIGLIA (“Executive”). As used in this Agreement, the term “Affiliate” means any entity controlling, controlled by or under common control with the Company. The Company and Executive are herein referred to each as a “Party”

Hagerty Appoints Jeff Briglia as President of Insurance

Exhibit 99.1 FOR IMMEDIATE RELEASE Hagerty Appoints Jeff Briglia as President of Insurance TRAVERSE CITY, Mich., May 31, 2024 – Hagerty (NYSE: HGTY) announced today that Jeff Briglia has been named Hagerty’s new President of Insurance, effective July 1, 2024, to lead all aspects of the company’s insurance operations. “I am pleased to welcome Jeff to the Hagerty team as we continue to position the

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 29, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commissi

, 2024, among The Hagerty Group, LLC, Wells Fargo Bank, National Association, and JPMorgan Chase Bank, N.A., as administrative agent, issuing bank and swinglin

Exhibit 10.1 ELEVENTH AMENDMENT TO AMENDED AND RESTATED CREDIT AGREEMENT This Eleventh Amendment to Amended and Restated Credit Agreement, dated as of May 10, 2024 (this “Amendment”), is by and among THE HAGERTY GROUP, LLC (the “Company”), the New Lender (as defined below), and JPMORGAN CHASE BANK, N.A., a national banking association, as administrative agent for the Lenders party to the Credit Ag

Hagerty Reports First Quarter 2024 Results Reaffirms 2024 Outlook for Strong Growth and Margin Expansion

For Immediate Release Hagerty Reports First Quarter 2024 Results Reaffirms 2024 Outlook for Strong Growth and Margin Expansion •First quarter 2024 Total Revenue increased 24% year-over-year to $271.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-40244 HAGERTY,

Form of Restricted Stock Unit Award Agreement pursuant to the Hagerty, Inc. 2021 Stock Incentive Plan, filed herewith.

Exhibit 10.3 RESTRICTED STOCK UNIT AWARD AGREEMENT PURSUANT TO THE HAGERTY, INC. 2021 STOCK INCENTIVE PLAN * * * * * Participant: #ParticipantName# Grant Date: #GrantDate# Number of Restricted Stock Units Granted Pursuant to this Agreement: #QuantityGranted# * * * * * THIS RESTRICTED STOCK UNIT AWARD AGREEMENT (this “Agreement”), dated as of the Grant Date specified above, is entered into by and b

Amendment to Employment Agreement, dated as of January 1, 2024, by and between the Company and Kenneth Ahn, filed herewith.

Exhibit 10.1 Execution Version AMENDED AND RESTATED EMPLOYMENT AGREEMENT THIS AMENDED AND RESTATED EMPLOYMENT AGREEMENT (“Agreement”) is made by THE HAGERTY GROUP, LLC, a Delaware limited liability company (“Company”), and Kenneth H. Ahn (“Executive”). As used in this Agreement, the term “Affiliate” means any entity controlling, controlled by or under common control with the Company. RECITALS 1.Th

Total Revenue growth of 24% Commission and Fee growth of 19% Written Premium growth of 19% » Added 59,000 new customers in the quarter Membership, Marketplace and other revenue growth of 18% » Marketplace growth of 58% Significantly improved profitab

a24-q1xinvestorxdeckx050 Total Revenue growth of 24% Commission and Fee growth of 19% Written Premium growth of 19% » Added 59,000 new customers in the quarter Membership, Marketplace and other revenue growth of 18% » Marketplace growth of 58% Significantly improved profitability » Improved operating margin by 1,210 bps » Net Income1 of $8 million compared to $(15) million » Adjusted EBITDA2 of $27 million compared to $7 million 1 Net Income in the current year includes a $6 million loss as a result of an increase in the fair value of warrant liabilities.

Stockholder Letter Q1 2024 HAGERTY Q1 2024 | 2 Driving season is upon us! For car enthusiasts, these next six months are the best of the year, and Hagerty is there to protect people’s special vehicles as they get out on the road. Insurance, of course

a24-q1stockholderletter0 Stockholder Letter Q1 2024 HAGERTY Q1 2024 | 2 Driving season is upon us! For car enthusiasts, these next six months are the best of the year, and Hagerty is there to protect people’s special vehicles as they get out on the road.

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 7, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commissio

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the app

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy State

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the app

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy State

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 March 29, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exac

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 March 29, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commis

Form of Performance Restricted Stock Unit Award Agreement pursuant to the Hagerty, Inc. 2021 Stock Incentive Plan (incorporated by reference to Exhibit 10.1 of the Company's Form 8-K (File No. 001-40244), filed with the SEC on April 1, 2024).

EXHIBIT 10.1 PERFORMANCE RESTRICTED STOCK UNIT AWARD AGREEMENT PURSUANT TO THE HAGERTY, INC. 2021 STOCK INCENTIVE PLAN * * * * * Participant: as specified through the electronic acceptance process provided by the Company or its designee. Grant Date: as specified through the electronic acceptance process provided by the Company or its designee. Target Number of Performance Restricted Stock Units Gr

Policy for the Recovery of Erroneously Awarded Incentive Compensation, adopted by the Board of the Company dated November 16, 2023, filed herewith.

EXHIBIT 97.1 HAGERTY, INC. POLICY FOR RECOVERY OF ERRONEOUSLY AWARDED INCENTIVE COMPENSATION (Adopted Nov 16, 2023) 1. INTRODUCTION Hagerty, Inc. (the “Company”) is adopting this policy (this “Policy”) to provide for the Company’s recovery of certain Incentive Compensation (as defined below) erroneously awarded to Affected Officers (as defined below) under certain circumstances. This Policy is adm

Regulation FD Disclosure, Financial Statements and Exhibits, Completion of Acquisition or Disposition of Assets

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 March 12, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commis

Amended and Restated Annual Incentive Plan of The Hagerty Group, LLC., effective January 1, 2023, filed herewith.

HAGERTY FOURTH AMENDED AND RESTATED ANNUAL INCENTIVE PLAN Effective January 1, 2023 EXHIBIT 10.

Subsidiaries of the Company, filed herewith

Exhibit 21.1 Name State or Other Jurisdiction of Incorporation Doing Business As The Hagerty Group, LLC Delaware Hagerty Asset Management, LLC Michigan Hagerty International Holdings Limited United Kingdom Classic Car Analytics GMBH Germany Hagerty International Limited United Kingdom Hagerty Enthusiast Limited United Kingdom Hagerty Insurance Agency, LLC Delaware Hagerty Canada, LLC Delaware Hage

Amended and Restated Deferred Incentive Awards Plan of Hagerty Insurance Agency, LLC., effective January 1, 2019, filed herewith.

HAGERTY AMENDED AND RESTATED DEFERRED INCENTIVE AWARDS PLAN EXHIBIT 10.34 HAGERTY AMENDED AND RESTATED DEFERRED INCENTIVE AWARDS PLAN SECTION 1 Declaration 1.1 Establishment of Plan. This is the Hagerty Amended and Restated Deferred Incentive Awards Plan (“plan” or “this plan”), established by Hagerty Insurance Agency, LLC (the “Company”), as a nonqualified plan for a select group of management pe

HAGERTY Q4 2023 | 2 In 2024, Hagerty will celebrate our 40th year as a company. Along the way, we have enjoyed many significant milestones, but few as big as the transformation we undertook to adopt and implement a more efficient business model, one

HAGERTY Q4 2023 | 2 In 2024, Hagerty will celebrate our 40th year as a company. Along the way, we have enjoyed many significant milestones, but few as big as the transformation we undertook to adopt and implement a more efficient business model, one that allows us to significantly improve our profitability (necessary to reinvest back into our competitive advantages) while maintaining our high rate

Hagerty Insider Trading Policy, dated December 14, 2023, filed herewith.

EXHIBIT 19.1 Hagerty Insider Trading Policy Date 12/14/2023 Document Properties Property Description Distribution Info Classification Public Document Owner Chief Legal Officer Effective Date 12/14/2023 As a public company, Hagerty, Inc. (“Hagerty” or the “Company”) is required to comply with many federal securities laws and regulations. These laws also extend to employees, directors, and officers

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 forw

This presentation contains statements that constitute “forward-looking statements” within the meaning of the Private Securities Litigation Reform Act of 1995.

Hagerty Reports 2023 Results Expects Strong Growth and Margin Expansion to Continue in 2024

For Immediate Release Hagerty Reports 2023 Results Expects Strong Growth and Margin Expansion to Continue in 2024 •Fourth quarter 2023 Total Revenue increased 24% to $245.

Description of Registrant's Securities, filed herewith.

Exhibit 4.6 DESCRIPTION OF SECURITIES The following description of the securities of Hagerty, Inc. ("we," "our," "us," "Hagerty," "HGTY," and the "Company") is a summary and does not purport to be complete. It is subject to, and qualified in its entirety by reference to, our Third Amended and Restated Certificate of Incorporation (“Amended and Restated Charter”), our Amended and Restated Bylaws (“

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-40

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 26, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Com

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 January 12, 2024 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Comm

1 Hagerty Investor Update CNIC Acquisition February 12, 2024 EXHIBIT 99.1 2 Forward Looking Statements / Non-GAAP Financial Measures Hagerty: The world’s leading brand for auto enthusiasts to protect, buy, sell and enjoy their special cars 4 Evolutio

1 Hagerty Investor Update CNIC Acquisition February 12, 2024 EXHIBIT 99.1 2 Forward Looking Statements / Non-GAAP Financial Measures Hagerty: The world’s leading brand for auto enthusiasts to protect, buy, sell and enjoy their special cars 4 Evolution to Capture Commissions Plus Underwriting Profits Working Closely with our Partner Markel Markel acquired Essentia in 2012 to exclusively underwrite

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 December 18, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Com

Fifth Amended and Restated Master Alliance Agreement between the Company, The Hagerty Group, LLC, and Markel Corporation, dated December 18, 2023 (incorporated by reference to Exhibit 10.1 of the Company’s Form 8-K (File No. 001-40244), filed with the SEC on December 22, 2023).

Material indicated with a “[***]” has been omitted from this Exhibit because it is both (i) not material and (ii) would likely cause competitive harm to the Company if publicly disclosed.

Sixth Amended and Restated Limited Liability Company Agreement of The Hagerty Group, LLC, dated December 18, 2023 (incorporated by reference to Exhibit 10.2 of the Company’s Form 8-K (File No. 001-40244), filed with the SEC on December 22, 2023).

EXECUTION VERSION Exhibit 10.2 SIXTH AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT OF THE HAGERTY GROUP, LLC DATED AS OF DECEMBER 18, 2023 THE LIMITED LIABILITY COMPANY INTERESTS IN THE HAGERTY GROUP, LLC HAVE NOT BEEN REGISTERED UNDER THE U.S. SECURITIES ACT OF 1933, AS AMENDED, THE SECURITIES LAWS OF ANY STATE, OR ANY OTHER APPLICABLE SECURITIES LAWS, AND HAVE BEEN OR ARE BEING ISSUED

Tenth Amendment to Amended and Restated Credit Agreement, dated as of November 28, 2023, among The Hagerty Group, LLC, the Foreign Subsidiary Borrowers party hereto, the Lenders party hereto, and JPMorgan Chase Bank, N.A., as Administrative Agent (incorporated by reference to Exhibit 10.1 of the Company’s Form 8-K (File No. 001-40244), filed with the SEC on December 1, 2023).

Exhibit 10.1 Execution Version Material indicated with a “[***]” has been omitted from this exhibit because it is both (i) not material and (ii) would likely cause competitive harm to the Company if publicly disclosed. EXHIBIT A AMENDED AND RESTATED CREDIT AGREEMENT dated as of December 12, 2018 among THE HAGERTY GROUP, LLC, THE FOREIGN SUBSIDIARY BORROWERS PARTY HERETO, THE LENDERS PARTY HERETO a

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 28, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Com

HAGERTY Q3 2023 | 2 FORWARD 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-lookin

HAGERTY Q3 2023 | 2 FORWARD 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.

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 8, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Comm

Ninth Amendment to Amended and Restated Credit Agreement, dated as of September 19, 2023, among The Hagerty Group LLC, Broad Arrow Capital Europe Limited, Broad Arrow Capital UK Limited, the Lenders party hereto, and JPMorgan Chase Bank, N.A., as Administrative Agent (incorporated by reference to Exhibit 10.3 of the Company’s Form 10-Q (File No. 001-40244), filed with the SEC on November 8, 2023).

Exhibit 10.3 Execution Version NINTH AMENDMENT TO AMENDED AND RESTATED CREDIT AGREEMENT This Ninth Amendment to Amended and Restated Credit Agreement, dated as of September 18, 2023 (this “Amendment”), is by and among THE HAGERTY GROUP, LLC (the “Company”), Broad Arrow Capital Europe Limited, a private limited company incorporated in England and Wales with company number 13872922 (“BAC Europe”), B

Employment Agreement, dated August 1, 2023, by and between the Company and Diana Chafey (incorporated by reference to Exhibit 10.2 of the Company’s Form 10-Q (File No. 001-40244), filed with the SEC on November 8, 2023).

Exhibit 10.2 EMPLOYMENT AGREEMENT THIS EMPLOYMENT AGREEMENT (“Agreement”) is made by HAGERTY, INC., a Delaware corporation (“Company”) and DIANA CHAFEY (“Executive”). As used in this Agreement, the term “Affiliate” means any entity controlling, controlled by or under common control with the Company. 1.Effective Date and Term. This Agreement will take effect on August 1, 2023 (“Effective Date”) and

HAGERTY Q3 2023 | 2 For classic and enthusiast car owners, November is the time when we reminisce about the adventures of the past driving season (and a few flat- tire or popped gasket related misadventures) and begin to place some of our special car

HAGERTY Q3 2023 | 2 For classic and enthusiast car owners, November is the time when we reminisce about the adventures of the past driving season (and a few flat- tire or popped gasket related misadventures) and begin to place some of our special cars into hibernation while dreaming about the season to come.

Hagerty Reports Third Quarter 2023 Results Increases 2023 Outlook

For Immediate Release Hagerty Reports Third Quarter 2023 Results Increases 2023 Outlook •Third quarter 2023 Total Revenue increased 27% to $275.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-40244 HAGER

Up to 16,688,449 Shares of Series A Convertible Preferred Stock Offered by the Selling Stockholders Up to 13,347,928 Shares of Class A Common Stock Issuable Upon Conversion of Series A Convertible Preferred Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-274046 PROSPECTUS Up to 16,688,449 Shares of Series A Convertible Preferred Stock Offered by the Selling Stockholders Up to 13,347,928 Shares of Class A Common Stock Issuable Upon Conversion of Series A Convertible Preferred Stock On June 23, 2023, we consummated a private placement (the “Private Placement”) pursuant to that certain Securities

August 29, 2023

August 29, 2023 VIA EDGAR U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549-3720 Attention: Madeleine Mateo Re: Hagerty, Inc. Registration Statement on Form S-3 Filed August 17, 2023 File No. 333-274046 Acceleration Request Requested Date: August 31, 2023 Requested Time: 2:00 p.m., Eastern Time Ladies and Gentlemen: Pursuant to Rule 4

As filed with the Securities and Exchange Commission on August 17, 2023

As filed with the Securities and Exchange Commission on August 17, 2023 Registration No.

Filing Fee Table.

Exhibit 107 Calculation of Filing Fee Tables Form S-3 (Form Type) Hagerty, Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered(1) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Fees to Be Paid Equity Series A Convertib

HAGERTY Q2 2023 | 2 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 histori

a23-q2xinvestorxdeckxfin HAGERTY Q2 2023 | 2 This presentation contains statements that constitute “forward-looking statements” within the meaning of the Private Securities Litigation Reform Act of 1995.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-40244 HAGERTY, I

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 August 8, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commis

Eighth Amendment to Amended and Restated Credit Agreement, dated as of June 15, 2023, among The Hagerty Group LLC, Broad Arrow Capital Europe Limited, Broad Arrow Capital UK Limited, the Lenders party hereto, and JPMorgan Chase Bank, N.A., as Administrative Agent, (incorporated by reference to Exhibit 10.1 of the Company’s Form 10-Q (File No. 001-40244), filed with the SEC on August 8, 2023).

Exhibit 10.1 Execution Version EIGHTH AMENDMENT TO AMENDED AND RESTATED CREDIT AGREEMENT This Eighth Amendment to Amended and Restated Credit Agreement, dated as of June 15, 2023 (this “Amendment”), is by and among THE HAGERTY GROUP, LLC (the “Company”), Broad Arrow Capital Europe Limited, a private limited company incorporated in England and Wales with company number 13872922 (“BAC Europe”), Broa

HAGERTY Q2 2023 | 2 S T O C K H O L D E R L E T T E R Pivoting to Profitability August is the peak of driving season for the 67 million auto enthusiasts in the United States. The term “enthusiasts” means far more than people just liking their special

a23-q2stockholderletter0 HAGERTY Q2 2023 | 2 S T O C K H O L D E R L E T T E R Pivoting to Profitability August is the peak of driving season for the 67 million auto enthusiasts in the United States.

Hagerty Reports Second Quarter 2023 Results Increases 2023 Outlook

For Immediate Release Hagerty Reports Second Quarter 2023 Results Increases 2023 Outlook •Second quarter 2023 Total Revenue increased 27% to $261.

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 August 2, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commis

Executive Retention, Transition and Release Agreement, dated July 31, 2023, by and between The Hagerty Group, LLC and Barbara Matthews (incorporated by reference to Exhibit 10.1 of the Company’s Form 8-K (File No. 001-40244), filed with the SEC on August 2, 2023).

CONFIDENTIAL EXECUTIVE RETENTION, TRANSITION AND RELEASE AGREEMENT This is an Executive Retention, Transition and Release Agreement (“Agreement”), entered into between The Hagerty Group, LLC (“Hagerty” or “Company”), and Barbara Matthews (“Executive”).

HGTY / Hagerty Inc - Class A / MARKEL CORP - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 1)* Hagerty, Inc. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 405166109 (CUSIP Number) Richard R. Grinnan Senior Vice President, Chief Legal Officer and Secretary Markel Group Inc. 4521 Highwoods Parkway

Securities Purchase Agreement, dated as of June 23, 2023, by and among the Company, State Farm Mutual Automobile Insurance Company, Markel Group Inc., McKeel O Hagerty Revocable Trust dated September 18, 2003, and First Restated Tammy J. Hagerty Revocable Trust dated September 2, 2004 (incorporated by reference to Exhibit 10.1 of the Company’s Form 8-K (File No. 001-40244), filed with the SEC on June 23, 2023).

EXECUTION VERSION SECURITIES PURCHASE AGREEMENT This SECURITIES PURCHASE AGREEMENT (the “Agreement”), dated as of June 23, 2023 (this “Agreement”), is made by and among Hagerty, Inc.

Certificate of Designations, Preferences and Rights of Series A Convertible Preferred Stock of the Company dated June 23, 2023 (incorporated by reference to Exhibit 3.1 of the Company’s Form 8-K (File No. 001-40244), filed with the SEC on June 23, 2023).

EXECUTION VERSION CERTIFICATE OF DESIGNATIONS, PREFERENCES AND RIGHTS OF SERIES A CONVERTIBLE PREFERRED STOCK OF HAGERTY, INC.

Fifth Amended and Restated Limited Liability Company Agreement of The Hagerty Group, LLC, dated as of June 23, 2023.

EXECUTION VERSION FIFTH AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT OF THE HAGERTY GROUP, LLC DATED AS OF JUNE 23, 2023 THE LIMITED LIABILITY COMPANY INTERESTS IN THE HAGERTY GROUP, LLC HAVE NOT BEEN REGISTERED UNDER THE U.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 23, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 23, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commiss

Hagerty Raises $105 Million in Capital from Strategic Investors Proceeds for Profitable Growth Initiatives

For Immediate Release Hagerty Raises $105 Million in Capital from Strategic Investors Proceeds for Profitable Growth Initiatives TRAVERSE CITY, Mich.

HGTY / Hagerty Inc - Class A / STATE FARM MUTUAL AUTOMOBILE INSURANCE CO - SC 13D/A Activist Investment

SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 3) HAGERTY, INC. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 405166109 (CUSIP Number) Stephen M. McManus State Farm Mutual Automobile Insurance Company One State Farm Plaza Bloomington, IL 61710

Registration Rights Agreement, dated as of June 23, 2023, by and among the Company, State Farm Mutual Automobile Insurance Company, Markel Group Inc., McKeel O Hagerty Revocable Trust dated September 18, 2003, and First Restated Tammy J. Hagerty Revocable Trust dated September 2, 2004 (incorporated by reference to Exhibit 10.2 of the Company’s Form 8-K (File No. 001-40244), filed with the SEC on June 23, 2023).

EXECUTION VERSION REGISTRATION RIGHTS AGREEMENT This REGISTRATION RIGHTS AGREEMENT (this “Agreement”), dated as of June 23, 2023, is made by and among Hagerty, Inc.

Amendment No. 1 to Tax Receivable Agreement, dated as of June 23, 2023, by and among the Company, The Hagerty Group, LLC, Hagerty Holding Corp. and Markel Group Inc (incorporated by reference to Exhibit 10.4 of the Company’s Form 8-K (File No. 001-40244), filed with the SEC on June 23, 2023).

AMENDMENT NO. 1 TO TAX RECEIVABLE AGREEMENT THIS AMENDMENT NO. 1 TO TAX RECEIVABLE AGREEMENT (this “Amendment”), dated as of June 23, 2023, is hereby entered into by and among Hagerty, Inc., a Delaware corporation (“PubCo”), The Hagerty Group, LLC, a Delaware limited liability company (the “Company”), Hagerty Holding Corp., a Delaware close corporation (“HHC”), and Markel Group Inc. (f/k/a Markel

1 Investor Update Capital Raise June 23, 2023 2Proprietary and Confidential Forward Looking Statements / Non-GAAP Financial Measures 3 Hagerty’s strategy is delivering strong growth and improved profitability Hagerty’s Four Strategic Focus Areas 2022

capitalraiseinvestorslid 1 Investor Update Capital Raise June 23, 2023 2Proprietary and Confidential Forward Looking Statements / Non-GAAP Financial Measures 3 Hagerty’s strategy is delivering strong growth and improved profitability Hagerty’s Four Strategic Focus Areas 2022 KPIs 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.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 5, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 5, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commissi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-40244 HAGERTY,

HAGERTY Q1 2023 | 2 S T O C K H O L D E R L E T T E R A Burgeoning Opportunity As a car aficionado, the best day of the year to me is the day when the snow finally disappears and I get to fire up my red ’67 Porsche 911S and take to the road for the f

a23-q1stockholderletter0 HAGERTY Q1 2023 | 2 S T O C K H O L D E R L E T T E R A Burgeoning Opportunity As a car aficionado, the best day of the year to me is the day when the snow finally disappears and I get to fire up my red ’67 Porsche 911S and take to the road for the first drive of the season.

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 for

a23-q1xinvestorxdeckxwkx This presentation contains statements that constitute “forward-looking statements” within the meaning of the Private Securities Litigation Reform Act of 1995.

Sixth Amendment to Amended and Restated Credit Agreement, dated as of January 31, 2023, among The Hagerty Group LLC, and JPMorgan Chase Bank, N.A., as Administrative Agent to the Lenders (incorporated by reference to Exhibit 10.1 of the Company’s Form 10-Q (File No. 001-40244), filed with the SEC on May 9, 2023).

Exhibit 10.1 SIXTH AMENDMENT TO AMENDED AND RESTATED CREDIT AGREEMENT This Sixth Amendment to Amended and Restated Credit Agreement, dated as of January 31, 2023 (this “Amendment”), is by and among THE HAGERTY GROUP, LLC (the “Borrower”), and JPMORGAN CHASE BANK, N.A., a national banking association, as administrative agent for the Lenders party to the Credit Agreement described below (in such cap

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 9, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact n

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 9, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commissio

Seventh Amendment to Amended and Restated Credit Agreement, dated as of April 7, 2023, among The Hagerty Group LLC, and JPMorgan Chase Bank, N.A., as Administrative Agent to the Lenders (incorporated by reference to Exhibit 10.1 of the Company’s Form 10-Q (File No. 001-40244), filed with the SEC on May 9, 2023).

Exhibit 10.2 Execution Version SEVENTH AMENDMENT TO AMENDED AND RESTATED CREDIT AGREEMENT This Seventh Amendment to Amended and Restated Credit Agreement, dated as of April 7, 2023 (this “Amendment”), is by and among THE HAGERTY GROUP, LLC (the “Company”), Broad Arrow Capital Europe Limited, a private limited company incorporated in England and Wales with company number 13872922 (“BAC Europe”), Br

Hagerty Reports First Quarter 2023 Results On Track to Deliver Strong Growth and Improved Profitability in 2023

For Immediate Release Hagerty Reports First Quarter 2023 Results On Track to Deliver Strong Growth and Improved Profitability in 2023 •First quarter 2023 Total Revenue increased 30% year-over-year to $218.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the app

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Definitive Proxy State

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 April 12, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exac

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 April 12, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commis

Amendment to Employment Agreement, dated January 1, 2023, by and between the Company and Patrick McClymont (incorporated by reference to Exhibit 10.17 of the Company’s Form 10-K (File No. 001-40244), filed with the SEC on March 14, 2023).

Exhibit 10.17 AMENDMENT TO EMPLOYMENT AGREEMENT This Amendment to Employment Agreement (the “Amendment”), dated as of January 1, 2023, is entered into by and among Hagerty, Inc., a Delaware corporation (“Company”), and Patrick McClymont (“Executive”), also referred to as the "Parties", and each, a "Party". WHEREAS, the Parties have entered into the Employment Agreement, dated September 6, 2022, th

Fifth Amendment to Amended and Restated Credit Agreement, dated as of December 30, 2022, among The Hagerty Group, LLC, the Lenders party hereto, and JPMorgan Chase Bank, N.A., as Administrative Agent

Exhibit 10.24 Execution Version Material indicated with a “[***]” has been omitted from this exhibit because it is both (i) not material and (ii) would likely cause competitive harm to the company if publicly disclosed. Exhibit A - The Hagerty Group, LLC Fifth Amendment AMENDED AND RESTATED CREDIT AGREEMENT dated as of December 12, 2018 among THE HAGERTY GROUP, LLC, THE FOREIGN SUBSIDIARY BORROWER

Subsidiaries of the Company, filed herewith.

Exhibit 21.1 Name State or Other Jurisdiction of Incorporation Doing Business As The Hagerty Group, LLC Delaware Hagerty Asset Management, LLC Michigan Hagerty International Holdings Limited United Kingdom Classic Car Analytics GMBH Germany Hagerty International Limited United Kingdom Hagerty Enthusiast Limited United Kingdom Hagerty Insurance Agency, LLC Delaware Hagerty Canada, LLC Delaware Hage

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-40244 HAGERTY, INC.

Hagerty Reports Full Year 2022 Results Provides 2023 Outlook for 22-26% Total Revenue Growth

For Immediate Release Hagerty Reports Full Year 2022 Results Provides 2023 Outlook for 22-26% Total Revenue Growth •Fourth quarter 2022 Total Revenue increased 28% year-over-year to $197.

Amendment to Employment Agreement, dated January 1, 2023, by and between the Company and Paul E. Rehrig (incorporated by reference to Exhibit 10.13 of the Company’s Form 10-K (File No. 001-40244), filed with the SEC on March 14, 2023).

Exhibit 10.13 AMENDMENT TO EMPLOYMENT AGREEMENT This Amendment to Employment Agreement (the “Amendment”), dated as of January 1, 2023, is entered into by and among The Hagerty Group, LLC, a Delaware limited liability company (“Company”), and Paul E. Rehrig (“Executive”), also referred to as the "Parties", and each, a "Party". WHEREAS, the Parties have entered into the Employment Agreement, dated A

Employment Agreement, dated December 1, 2021, by and between the Company and Kenneth Ahn (incorporated by reference to Exhibit 10.18 of the Company’s Form 10-K (File No. 001-40244), filed with the SEC on March 14, 2023).

Exhibit 10.18 EMPLOYMENT AGREEMENT THIS EMPLOYMENT AGREEMENT (“Agreement”) is made by THE HAGERTY GROUP, LLC, a Delaware limited liability company (“Company”), and Kenneth H. Ahn (“Executive”). As used in this Agreement, the term “Affiliate” means any entity controlling, controlled by or under common control with the Company and the Company’s subsidiaries; however, as of the date of this Agreement

Exhibit 4.6

Exhibit 4.6 DESCRIPTION OF SECURITIES The following description of the securities of Hagerty, Inc. ("we," "our," "us," "Hagerty," "HGTY," and the "Company") is a summary and does not purport to be complete. It is subject to, and qualified in its entirety by reference to, our Second Amended and Restated Certificate of Incorporation (“Amended and Restated Charter”) and our Amended and Restated Bylaw

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 March 14, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exac

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 March 14, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commis

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 seas

a2022q4-stockholderlette HAGERTY Q4 2022 | 2 S T O C K H O L D E R L E T T E R Springing Forward T.

Amended and Restated Exchange Agreement, dated as of March 23, 2022, by and among the Company, The Hagerty Group, LLC, Markel Corporation, and Hagerty Holding Corp. Form of Indemnification Agreement by and between the Company and its directors and officers (incorporated by reference to Exhibit 10.8 of the Company’s Form 10-K (File No. 001-40244), filed with the SEC on March 14, 2023).

Exhibit 10.8 AMENDED AND RESTATED EXCHANGE AGREEMENT AMENDED AND RESTATED EXCHANGE AGREEMENT (this “Agreement”), originally dated as of December 2, 2021 and amended and restated as of March 23, 2022 (the “Effective Date”), by and among Hagerty, Inc., a Delaware corporation (the “Corporation”), The Hagerty Group, LLC, a Delaware limited liability company (together with any successor thereto, “OpCo”

Amendment to Employment Agreement, dated March 10, 2023, by and between the Company and McKeel O Hagerty (incorporated by reference to Exhibit 10.15 of the Company’s Form 10-K (File No. 001-40244), filed with the SEC on March 14, 2023).

Exhibit 10.15 AMENDMENT TO EMPLOYMENT AGREEMENT This Amendment to Employment Agreement (the “Amendment”), dated as of March 10, 2023, is entered into by and among The Hagerty Group, LLC, a Delaware limited liability company (“Company”), and McKeel O Hagerty (“Executive”), also referred to as the "Parties", and each, a "Party". WHEREAS, the Parties have entered into the Employment Agreement, dated

Amended and Restated Employment Agreement, dated January 1, 2023, by and between the Company and Kenneth Ahn (incorporated by reference to Exhibit 10.19 of the Company’s Form 10-K (File No. 001-40244), filed with the SEC on March 14, 2023).

Exhibit 10.19 Execution Version AMENDED AND RESTATED EMPLOYMENT AGREEMENT THIS AMENDED AND RESTATED EMPLOYMENT AGREEMENT (“Agreement”) is made by THE HAGERTY GROUP, LLC, a Delaware limited liability company (“Company”), and Kenneth H. Ahn (“Executive”). As used in this Agreement, the term “Affiliate” means any entity controlling, controlled by or under common control with the Company. RECITALS 1.T

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 hist

a2022q4-investorpresenta FORWARD LOOKING STATEMENTS / NON-GAAP FINANCIAL MEASURES This presentation contains forward-looking statements within the meaning of Private Securities Litigation Reform Act of 1995.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 March 7, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 March 7, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commiss

Hagerty Names Randall Harbert to Hagerty’s Board of Directors State Farm Veteran Succeeds Michael Tipsord as State Farm Designee

FOR IMMEDIATE RELEASE Hagerty Names Randall Harbert to Hagerty’s Board of Directors State Farm Veteran Succeeds Michael Tipsord as State Farm Designee TRAVERSE CITY, Mich.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 23, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (E

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 February 23, 2023 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Com

HGTY / Hagerty Inc - Class A / STATE FARM MUTUAL AUTOMOBILE INSURANCE CO - SC 13D/A Activist Investment

SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 2) HAGERTY, INC. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 405166109 (CUSIP Number) Stephen M. McManus State Farm Mutual Automobile Insurance Company One State Farm Plaza Bloomington, IL 61710

Up to 5,438,244 Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration Statement No. 333-269555 PROSPECTUS Up to 5,438,244 Shares of Class A Common Stock This prospectus relates to the resale from time to time by the selling stockholders identified in this prospectus (the “Selling Stockholders”) of up to 5,438,244 shares of our Class A Common Stock, par value $0.0001 per share (“Class A Common Stock”), consisting of up to

February 13, 2023

February 13, 2023 VIA EDGAR U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.E. Washington, D.C. 20549-3720 Attention: John Stickel Re: Hagerty, Inc. Registration Statement on Form S-3 Filed February 3, 2023 File No. 333-269555 Acceleration Request Requested Date: February 15, 2023 Requested Time: 2:00 p.m., Eastern Time Ladies and Gentlemen: Pursuant to Rule

HGTY / Hagerty Inc - Class A / STATE FARM MUTUAL AUTOMOBILE INSURANCE CO - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 1) HAGERTY, INC. (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 405166109 (CUSIP Number) Stephen M. McManus State Farm Mutual Automobile Insurance Company One State Farm Plaza Bloomington, IL 61710 (309) 766

Up to 251,033,906 Shares of Class A Common Stock Issuable Upon Exchange of Class V Common Stock and OpCo Units Up to 20,005,550 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Up to 339,121,956 Shares of Class A Common Stock Offered

Filed Pursuant to Rule 424(b)(3) Registration Statement No. 333-261810 PROSPECTUS Up to 251,033,906 Shares of Class A Common Stock Issuable Upon Exchange of Class V Common Stock and OpCo Units Up to 20,005,550 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Up to 339,121,956 Shares of Class A Common Stock Offered by the Selling Securityholders Up to 12,669,300 PIPE Warrants Offer

Filing Fee Table.

Exhibit 107 EX-FILING FEES Calculation of Filing Fee Tables Form S-3 (Form Type) Hagerty, Inc.

As filed with the Securities and Exchange Commission on February 3, 2023

As filed with the Securities and Exchange Commission on February 3, 2023 Registration No.

*****

January 20, 2023 VIA EDGAR Attention: Madeleine Joy Mateo and John Dana Brown United States Securities and Exchange Commission Division of Corporation Finance Office of Finance 100 F Street, NE Washington, D.

Third Amended and Restated Certificate of Incorporation of the Company, dated December 2, 2021 (incorporated by reference to Exhibit 3.1 of the Company’s Amendment No.3 to Form S-1 (File No. 333-261810), filed with the SEC on January 20, 2023).

Exhibit 3.1 EXECUTION VERSION THIRD AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF ALDEL FINANCIAL INC., a Delaware corporation Aldel Financial Inc., a corporation organized and existing under the laws of the State of Delaware (the “Corporation”), hereby certifies as follows: A. The name of the Corporation is Aldel Financial Inc. The Corporation’s original certificate of incorporation was fi

As filed with the Securities and Exchange Commission on January 20, 2023

As filed with the Securities and Exchange Commission on January 20, 2023 Registration No.

Filing Fee Table.

Exhibit 107 EX-FILING FEES Calculation of Filing Fee Tables Form S-3 (Form Type) Hagerty, Inc.

rporation of the Company, dated December 2,

Exhibit 3.1 EXECUTION VERSION THIRD AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF ALDEL FINANCIAL INC., a Delaware corporation Aldel Financial Inc., a corporation organized and existing under the laws of the State of Delaware (the ?Corporation?), hereby certifies as follows: A. The name of the Corporation is Aldel Financial Inc. The Corporation?s original certificate of incorporation was fi

As filed with the Securities and Exchange Commission on December 21, 2022

As filed with the Securities and Exchange Commission on December 21, 2022 Registration No.

344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 1,300,000 OTM Warrants Up to 257,500 Private Placement Warrants Up to 28,750 Underwriter Warrants

Filed pursuant to Rule 424(b)(3) Registration Statement No. 333-261810 Prospectus Supplement No. 10 (to Prospectus dated April 14, 2022) 344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 1,300,000 OTM Warrants Up to 257,500 Private Placement Warrants Up to 28,750 Underwriter Warrants This prospectus supplement updates, amends and supplements the prospectus dated April

Regulation FD Disclosure, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 December 1, 2022 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Comm

Fourth Amendment to Amended and Restated Credit Agreement, dated as of September 30, 2022, among The Hagerty Group LLC, the Lenders party hereto, and JPMorgan Chase Bank, N.A., as Administrative Agent. Portions of this Exhibit have been omitted.

Exhibit 10.1 Material indicated with a ?[***]? has been omitted from this exhibit because it is both (i) not material and (ii) would likely cause competitive harm to the company if publicly disclosed. Execution Version Exhibit A - The Hagerty Group, LLC Fourth Amendment AMENDED AND RESTATED CREDIT AGREEMENT dated as of December 12, 2018 among THE HAGERTY GROUP, LLC, The Lenders Party Hereto and JP

HAGERTY Q3 2022 | 2 S T O C K H O L D E R L E T T E R Welcome to Hagerty Marketplace! In Niall Ferguson’s 2011 book, “Civilization: The West and the Rest,” the Stanford historian posits that consumerism is a core strength of western society, without

HAGERTY Q3 2022 | 2 S T O C K H O L D E R L E T T E R Welcome to Hagerty Marketplace! In Niall Ferguson?s 2011 book, ?Civilization: The West and the Rest,? the Stanford historian posits that consumerism is a core strength of western society, without which the Industrial Revolution may have fizzled.

344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 1,300,000 OTM Warrants Up to 257,500 Private Placement Warrants Up to 28,750 Underwriter Warrants

Filed pursuant to Rule 424(b)(3) Registration Statement No. 333-261810 Prospectus Supplement No. 9 (to Prospectus dated April 14, 2022) 344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 1,300,000 OTM Warrants Up to 257,500 Private Placement Warrants Up to 28,750 Underwriter Warrants This prospectus supplement updates, amends and supplements the prospectus dated April

Regulation FD Disclosure, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 10, 2022 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Com

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 hist

FORWARD LOOKING STATEMENTS / NON-GAAP FINANCIAL MEASURES This presentation contains forward-looking statements within the meaning of Private Securities Litigation Reform Act of 1995.

Release and Settlement Agreement, dated November

RELEASE AND SETTLEMENT AGREEMENT This Release and Settlement Agreement (?Agreement?) is entered into by and between THE HAGERTY GROUP, LLC, a Delaware limited liability company (the ?Hagerty Group?), and KELLY SMITH (?Smith?) (the Hagerty Group and Smith are collectively referred to as the "Parties"), as of the date the Agreement is signed by both Parties.

344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 257,500 Private Placement Warrants Up to 1,300,000 OTM Warrants Up to 28,750 Underwriter Warrants

Filed pursuant to Rule 424(b)(3) Registration Statement No. 333-261810 Prospectus Supplement No. 8 (to Prospectus dated April 14, 2022) 344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 257,500 Private Placement Warrants Up to 1,300,000 OTM Warrants Up to 28,750 Underwriter Warrants This prospectus supplement updates, amends and supplements the prospectus dated April

, among The Hagerty Group, LLC, the Lenders party hereto, and JPMorgan Chase Bank, N.A., as Administrative Agent (incorporated by reference to Exhibit 10.1

Exhibit 10.1 Material indicated with a ?[***]? has been omitted from this exhibit because it is both (i) not material and (ii) would likely cause competitive harm to the company if publicly disclosed. Execution Version Exhibit A - The Hagerty Group, LLC Fourth Amendment AMENDED AND RESTATED CREDIT AGREEMENT dated as of December 12, 2018 among THE HAGERTY GROUP, LLC, The Lenders Party Hereto and JP

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 November 8, 2022 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Comm

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-40244 HAGER

Release and Settlement Agreement, dated November 8, 2022, by and between Kelly Smith and The Hagerty Group, LLC

RELEASE AND SETTLEMENT AGREEMENT This Release and Settlement Agreement (?Agreement?) is entered into by and between THE HAGERTY GROUP, LLC, a Delaware limited liability company (the ?Hagerty Group?), and KELLY SMITH (?Smith?) (the Hagerty Group and Smith are collectively referred to as the "Parties"), as of the date the Agreement is signed by both Parties.

Hagerty Reports Third Quarter 2022 Results

For Immediate Release Hagerty Reports Third Quarter 2022 Results ?Third quarter 2022 Total Revenue increased 29% year-over-year to $216.

344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 257,500 Private Placement Warrants Up to 1,300,000 OTM Warrants Up to 28,750 Underwriter Warrants

Filed pursuant to Rule 424(b)(3) Registration Statement No. 333-261810 Prospectus Supplement No. 7 (to Prospectus dated April 14, 2022) 344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 257,500 Private Placement Warrants Up to 1,300,000 OTM Warrants Up to 28,750 Underwriter Warrants This prospectus supplement updates, amends and supplements the prospectus dated April

Press Release, Dated August 23, 2022

FOR IMMEDIATE RELEASE Hagerty Appoints Patrick McClymont as new Chief Financial Officer, Announces Planned Retirement and Transition for Longtime CFO Fred Turcotte TRAVERSE CITY, Mich.

Hagerty Appoints Patrick McClymont as new Chief Financial Officer, Announces Planned Retirement and Transition for Longtime CFO Fred Turcotte

FOR IMMEDIATE RELEASE Hagerty Appoints Patrick McClymont as new Chief Financial Officer, Announces Planned Retirement and Transition for Longtime CFO Fred Turcotte TRAVERSE CITY, Mich.

Employment Agreement, dated August 19, 2022, by and between the Company and Patrick McClymont (incorporated by reference to Exhibit 10.1 of the Company’s Form 8-K (File No. 001-40244), filed with the SEC on August 23, 2022).

Exhibit 10.1 EMPLOYMENT AGREEMENT THIS EMPLOYMENT AGREEMENT (?Agreement?) is made by HAGERTY, INC., a Delaware corporation (?Company?) and PATRICK MCCLYMONT (?Executive?). As used in this Agreement, the term ?Affiliate? means any entity controlling, controlled by or under common control with the Company. 1. Effective Date and Term. This Agreement will take effect on September 6, 2022 (?Effective D

Employment Agreement, Dated August 19, 2022, by and between the Company and Patrick McClymont

Exhibit 10.1 EMPLOYMENT AGREEMENT THIS EMPLOYMENT AGREEMENT (?Agreement?) is made by HAGERTY, INC., a Delaware corporation (?Company?) and PATRICK MCCLYMONT (?Executive?). As used in this Agreement, the term ?Affiliate? means any entity controlling, controlled by or under common control with the Company. 1. Effective Date and Term. This Agreement will take effect on September 6, 2022 (?Effective D

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 August 23, 2022 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commi

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 August 16, 2022 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commi

344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 257,500 Private Placement Warrants Up to 1,300,000 OTM Warrants Up to 28,750 Underwriter Warrants

Filed pursuant to Rule 424(b)(3) Registration Statement No. 333-261810 Prospectus Supplement No. 6 (to Prospectus dated April 14, 2022) 344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 257,500 Private Placement Warrants Up to 1,300,000 OTM Warrants Up to 28,750 Underwriter Warrants This prospectus supplement updates, amends and supplements the prospectus dated April

Contribution and Exchange Agreement, dated August 9, 2022, by and among Hagerty, Inc., The Hagerty Group, LLC, Broad Arrow Group, Inc., Broad Arrow Holdings LLC, each other Contributor party thereto, and the Contributor Representative party thereto (incorporated by reference to Exhibit 10.1 of the Company’s Form 8-K (File No. 001-40244), filed with the SEC on August 10, 2022).

Exhibit 10.1 CONTRIBUTION AND EXCHANGE AGREEMENT BY AND AMONG HAGERTY, INC. THE HAGERTY GROUP, LLC, BROAD ARROW HOLDINGS LLC, BROAD ARROW GROUP, INC., THE CONTRIBUTOR REPRESENTATIVE, AND EACH OF THE CONTRIBUTORS PARTY THERETO TABLE OF CONTENTS Page Article 1 Contribution and Exchange; Closing 2 1.1 Contribution and Exchange 2 1.2 Closing; Delivery 4 1.3 Intended Tax Treatment 4 Article 2 Represent

Q2Stockholder Letter S T O C K H O L D E R L E T T E R Quarterly Update from McKeel Some people assume Henry Ford invented the automobile. He did not. That honor, arguably, goes to a gentleman named Karl Benz who patented the “Motorwagen” in 1886. Bu

Q2Stockholder Letter S T O C K H O L D E R L E T T E R Quarterly Update from McKeel Some people assume Henry Ford invented the automobile.

Hagerty Reports Second Quarter 2022 Results

For Immediate Release Hagerty Reports Second Quarter 2022 Results ?Second quarter 2022 Total Revenue increased 23% year-over-year to $206.

Regulation FD Disclosure, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 August 10, 2022 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commi

Contribution and Exchange Agreement, dated August 9, 2022, by and among Hagerty, Inc., The Hagerty Group, LLC, Broad Arrow Group, Inc., Broad Arrow Holdings LLC, each other Contributor party thereto, and the Contributor Representative party thereto.

Exhibit 10.1 CONTRIBUTION AND EXCHANGE AGREEMENT BY AND AMONG HAGERTY, INC. THE HAGERTY GROUP, LLC, BROAD ARROW HOLDINGS LLC, BROAD ARROW GROUP, INC., THE CONTRIBUTOR REPRESENTATIVE, AND EACH OF THE CONTRIBUTORS PARTY THERETO TABLE OF CONTENTS Page Article 1 Contribution and Exchange; Closing 2 1.1 Contribution and Exchange 2 1.2 Closing; Delivery 4 1.3 Intended Tax Treatment 4 Article 2 Represent

Hagerty Enters into Definitive Agreement to Acquire Broad Arrow Group

FOR IMMEDIATE RELEASE Hagerty Enters into Definitive Agreement to Acquire Broad Arrow Group TRAVERSE CITY, Mich.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-40244 HAGERTY, I

344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 257,500 Private Placement Warrants Up to 1,300,000 OTM Warrants Up to 28,750 Underwriter Warrants

Filed pursuant to Rule 424(b)(3) Registration Statement No. 333-261810 Prospectus Supplement No. 5 (to Prospectus dated April 14, 2022) 344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 257,500 Private Placement Warrants Up to 1,300,000 OTM Warrants Up to 28,750 Underwriter Warrants This prospectus supplement updates, amends and supplements the prospectus dated April

Speakers: McKeel Hagerty | Chief Executive Officer Frederick J. Turcotte | SVP & Chief Financial Officer Q2 HAGERTY Q2 2022 | 2 FORWARD-LOOKING STATEMENTS / NON-GAAP FINANCIAL MEASURES This presentation contains forward-looking statements within the

Speakers: McKeel Hagerty | Chief Executive Officer Frederick J. Turcotte | SVP & Chief Financial Officer Q2 HAGERTY Q2 2022 | 2 FORWARD-LOOKING STATEMENTS / NON-GAAP FINANCIAL MEASURES This presentation contains 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. Thes

Press Release, Dated August 10, 2022

FOR IMMEDIATE RELEASE Hagerty Enters into Definitive Agreement to Acquire Broad Arrow Group TRAVERSE CITY, Mich.

Regulation FD Disclosure

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 August 9, 2022 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commis

344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 257,500 Private Placement Warrants Up to 1,300,000 OTM Warrants Up to 28,750 Underwriter Warrants

Filed pursuant to Rule 424(b)(3) Registration Statement No. 333-261810 Prospectus Supplement No. 4 (to Prospectus dated April 14, 2022) 344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 257,500 Private Placement Warrants Up to 1,300,000 OTM Warrants Up to 28,750 Underwriter Warrants This prospectus supplement updates, amends and supplements the prospectus dated April

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 6, 2022 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 6, 2022 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commissi

344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 257,500 Private Placement Warrants Up to 1,300,000 OTM Warrants Up to 28,750 Underwriter Warrants

Filed pursuant to Rule 424(b)(3) Registration Statement No. 333-261810 Prospectus Supplement No. 3 (to Prospectus dated April 14, 2022) 344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 257,500 Private Placement Warrants Up to 1,300,000 OTM Warrants Up to 28,750 Underwriter Warrants This prospectus supplement updates, amends and supplements the prospectus dated April

344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 1,300,000 OTM Warrants Up to 257,500 Private Placement Warrants Up to 28,750 Underwriter Warrants

Filed pursuant to Rule 424(b)(3) Registration Statement No. 333-261810 Prospectus Supplement No. 1 (to Prospectus dated April 14, 2022) 344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 1,300,000 OTM Warrants Up to 257,500 Private Placement Warrants Up to 28,750 Underwriter Warrants This prospectus supplement updates, amends and supplements the prospectus dated April

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 17, 2022 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commiss

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 17, 2022 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 17, 2022 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commiss

Current Report

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 June 6, 2022 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commissi

Speakers: McKeel Hagerty | Chief Executive Officer Frederick J. Turcotte | SVP & Chief Financial Officer HAGERTY Q1 2022 | 2 FORWARD LOOKING STATEMENTS / NON-GAAP FINANCIAL MEASURES This presentation contains forward-looking statements within the mea

Speakers: McKeel Hagerty | Chief Executive Officer Frederick J. Turcotte | SVP & Chief Financial Officer HAGERTY Q1 2022 | 2 FORWARD LOOKING STATEMENTS / NON-GAAP FINANCIAL MEASURES This presentation contains 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 f

344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 1,300,000 OTM Warrants Up to 257,500 Private Placement Warrants Up to 28,750 Underwriter Warrants

Filed pursuant to Rule 424(b)(3) Registration Statement No. 333-261810 Prospectus Supplement No. 1 (to Prospectus dated April 14, 2022) 344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 1,300,000 OTM Warrants Up to 257,500 Private Placement Warrants Up to 28,750 Underwriter Warrants This prospectus supplement updates, amends and supplements the prospectus dated April

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-40244 HAGERTY,

HAGERTY Q1 2022 | 2 S T O C K H O L D E R L E T T E R 2022 is On Track & On Mission The cold winter months in much of North America found many automotive enthusiasts taking time off from driving. There were fewer car events, fewer drivable days, fewe

HAGERTY Q1 2022 | 2 S T O C K H O L D E R L E T T E R 2022 is On Track & On Mission The cold winter months in much of North America found many automotive enthusiasts taking time off from driving.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-Q (Mark One) ? QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2022 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission file number: 001-40244 HAGERTY,

Regulation FD Disclosure, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 May 9, 2022 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commissio

Hagerty Reports First Quarter 2022 Results - Total Revenue grew 30% year-over-year to $167.8 million - Written Premium grew 16% year-over-year to $154.8 million - Total Active Members grew 11% year-over-year to 2.5 million

For Immediate Release Hagerty Reports First Quarter 2022 Results - Total Revenue grew 30% year-over-year to $167.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the app

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy State

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant ☐ Check the app

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ? Filed by a Party other than the Registrant ? Check the appropriate box: ? Preliminary Proxy Statement ? Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ? Definitive Proxy State

344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 1,300,000 OTM Warrants Up to 257,500 Private Placement Warrants Up to 28,750 Underwriter Warrants

Filed Pursuant to Rule 424(b)(3) Registration Statement No. 333-261810 PROSPECTUS 344,871,956 Shares of Class A Common Stock Up to 12,669,300 PIPE Warrants Up to 1,300,000 OTM Warrants Up to 257,500 Private Placement Warrants Up to 28,750 Underwriter Warrants This prospectus relates to (i) the resale by the selling securityholders named in this prospectus (the ?Selling Securityholders?) of up to 7

As filed with the Securities and Exchange Commission on April 6, 2022 Registration No. 333-261810 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C . 20549 POST-EFFECTIVE AMENDMENT NO. 1 TO FORM S-1 REGISTRATION STATEMENT UNDER THE SEC

Table of Contents As filed with the Securities and Exchange Commission on April 6, 2022 Registration No.

Form 2 of Restricted Stock Unit Agreement pursuant to the Hagerty, Inc. 2021 Stock Incentive Plan (incorporated by reference to Exhibit 99.4 of the Company's Form S-8 (File No. 333-263989), filed with the SEC on March 30, 2022).

Exhibit 99.4 RESTRICTED STOCK UNIT AWARD AGREEMENT PURSUANT TO THE HAGERTY, INC. 2021 STOCK INCENTIVE PLAN * * * * * Participant: [?] Grant Date: [?] Number of Restricted Stock Units Granted: [?] * * * * * THIS RESTRICTED STOCK UNIT AWARD AGREEMENT (this ?Agreement?), dated as of the Grant Date specified above, is entered into by and between Hagerty, Inc., a corporation organized in the State of D

Performance Restricted Stock Unit Agreement pursuant to the Hagerty, Inc. 2021 Stock Incentive Plan (incorporated by reference to Exhibit 99.5 of the Company's Form S-8 (File No. 333-263989), filed with the SEC on March 30, 2022).

Exhibit 99.5 PERFORMANCE RESTRICTED STOCK UNIT AWARD AGREEMENT PURSUANT TO THE HAGERTY, INC. 2021 STOCK INCENTIVE PLAN * * * * * Participant: [?] Grant Date: [?] Number of Performance Restricted Stock Units Granted: [?] * * * * * THIS PERFORMANCE RESTRICTED STOCK UNIT AWARD AGREEMENT (this ?Agreement?), dated as of the Grant Date specified above, is entered into by and between Hagerty, Inc., a cor

Form 1 of Restricted Stock Unit Agreement pursuant to the Hagerty, Inc. 2021 Stock Incentive Plan (incorporated by reference to Exhibit 99.3 of the Company's Form S-8 (File No. 333-263989), filed with the SEC on March 30, 2022).

Exhibit 99.3 RESTRICTED STOCK UNIT AWARD AGREEMENT PURSUANT TO THE HAGERTY, INC. 2021 STOCK INCENTIVE PLAN * * * * * Participant: [?] Grant Date: [?] Number of Restricted Stock Units Granted: [?] * * * * * THIS RESTRICTED STOCK UNIT AWARD AGREEMENT (this ?Agreement?), dated as of the Grant Date specified above, is entered into by and between Hagerty, Inc., a corporation organized in the State of D

Filing Fee Table

EX-FILING FEES 2 ex107.htm EX-FILING FEES Exhibit 107 Calculation of Filing Fee Tables FORM S-8 (Form Type) Hagerty, Inc. (Exact Name of Registrant as Specified in its Charter) Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered(1) Proposed Maximum Offering Price per Share Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee(2) Fees

As filed with the Securities and Exchange Commission on March 30, 2022

As filed with the Securities and Exchange Commission on March 30, 2022 Registration No.

Speakers: McKeel Hagerty | Chief Executive Officer Frederick J. Turcotte | SVP & Chief Financial Officer FORWARD LOOKING STATEMENTS / NON-GAAP FINANCIAL MEASURES This presentation contains forward-looking statements within the meaning of Section 27A

Speakers: McKeel Hagerty | Chief Executive Officer Frederick J. Turcotte | SVP & Chief Financial Officer FORWARD LOOKING STATEMENTS / NON-GAAP FINANCIAL MEASURES This presentation contains forward-looking statements within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended. These statements may relate to, but are

Amended and Restated Exchange Agreement, dated as of March 23, 2022, by and among the Company, The Hagerty Group, LLC, Markel Corporation, and Hagerty Holding Corp., filed herewith.

Exhibit 10.8 AMENDED AND RESTATED EXCHANGE AGREEMENT AMENDED AND RESTATED EXCHANGE AGREEMENT (this ?Agreement?), originally dated as of December 2, 2021 and amended and restated as of March 23, 2022 (the ?Effective Date?), by and among Hagerty, Inc., a Delaware corporation (the ?Corporation?), The Hagerty Group, LLC, a Delaware limited liability company (together with any successor thereto, ?OpCo?

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2021 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to HAGERTY, INC. (Exact name of registrant as speci

Subsidiaries of the Company, filed herewith.

EX-21.1 4 hgty-20220324xex211.htm EX-21.1 Exhibit 21.1 Name State or Other Jurisdiction of Incorporation Doing Business As The Hagerty Group, LLC Delaware Hagerty Asset Management, LLC Michigan Hagerty International Holdings Limited England Classic Car Analytics GMBH Germany Hagerty International Limited England Hagerty Enthusiast Limited England Hagerty Insurance Agency, LLC Delaware Hagerty Cana

S T O C K H O L D E R L E T T E R Start your engines! HAGERTY Q4 2021 | 2 Hagerty went public for a simple reason: to better serve the vast community of people who love cars. These people wake up in the morning asking, “How can I spend more money and

S T O C K H O L D E R L E T T E R Start your engines! HAGERTY Q4 2021 | 2 Hagerty went public for a simple reason: to better serve the vast community of people who love cars.

Hagerty Reports Full Year 2021 Results Full Year 2021 - Total Revenue grew 24% year-over-year to $619.1 million - Written Premium grew 17% year-over-year to 674.3 million - Total Active Members grew 13% year-over-year to 2.4 million

EX-99.2 3 pressrelease.htm EX-99.2 For Immediate Release Hagerty Reports Full Year 2021 Results Full Year 2021 - Total Revenue grew 24% year-over-year to $619.1 million - Written Premium grew 17% year-over-year to 674.3 million - Total Active Members grew 13% year-over-year to 2.4 million TRAVERSE CITY, Mich., March 24, 2022 /PRNewswire/ – Hagerty, Inc. (NYSE: HGTY), an automotive lifestyle brand

Exhibit 4.6

Exhibit 4.6 DESCRIPTION OF SECURITIES The following description of the securities of Hagerty, Inc. ("we," "our," "us," "Hagerty," "HGTY," and the "Company") is a summary and does not purport to be complete. It is subject to, and qualified in its entirety by reference to, our Second Amended and Restated Certificate of Incorporation (?Amended and Restated Charter?) and our Amended and Restated Bylaw

Regulation FD Disclosure, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT Pursuant to Section 13 OR 15(d) of The Securities Exchange Act of 1934 March 24, 2022 Date of Report (date of earliest event reported) HAGERTY, INC. (Exact name of registrant as specified in its charter) Delaware 001-40244 86-1213144 (State or other jurisdiction of incorporation or organization) (Commis

HGTY / Hagerty Inc - Class A / BASSO CAPITAL MANAGEMENT, L.P. - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* Hagerty, Inc.** (Name of Issuer) Class A Common Stock, $0.0001 par value (Title of Class of Securities) 405166109 (CUSIP Number) December 31, 2021 (Date of Event which Requires Filing of this Statement) Check the appropriate box to designate the rule pur

FNCH / Finch Therapeutics Group, Inc. / WALTON S ROBSON - SCHEDULE 13G Passive Investment

SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 SCHEDULE 13G* (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1(b), (c), AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2 (AMENDMENT NO. 1)* Hagerty, Inc. ** (Name of Issuer) Class A Common Stock, $0.0001 Par Value (Title of Class of Securities) 405166109 (CUSIP Number) December 2, 2021 (Date o