[Form 4] Hagerty, Inc. Insider Trading Activity

Rhea-AI Filing Summary

Hagerty, Inc. (HGTY) director and reporting person exchanged 1,236,750 Paired Interests for an equal number of Class A common shares and then sold those 1,236,750 Class A shares on 08/13/2025 at $8.9197 per share. The filing shows 1,236,750 shares issued via the Amended and Restated Exchange Agreement and the same number sold the same day. After the transactions, the reporting person beneficially owns 166,552,156 shares of Class A common stock.

Positive

• Transaction disclosed promptly on Form 4, showing compliance with Section 16 reporting requirements
• Conversion executed under an existing Exchange Agreement, indicating the action followed contract terms

Negative

• Sale of 1,236,750 Class A shares at $8.9197 on 08/13/2025, representing a material insider disposition
• Gross proceeds implied (~$11.03 million) from the sale (1,236,750 x $8.9197) which may be notable to investors monitoring insider sales

Insights

Financial Analyst

TL;DR: Director converted Paired Interests to Class A shares and sold 1.24M shares at $8.9197, reducing his convertible holdings for cash.

The Form 4 records a simultaneous conversion and sale on 08/13/2025: 1,236,750 Paired Interests were surrendered under the Exchange Agreement and exchanged for 1,236,750 Class A shares, which were then sold at $8.9197 per share. This generates gross proceeds of approximately $11.03 million before fees and taxes. The reporting person retains a large residual stake of 166.55 million Class A shares, indicating continued significant ownership despite the sale.

Corporate Governance Expert

TL;DR: Transaction follows the issuer's Exchange Agreement mechanics and was disclosed via Form 4, demonstrating compliance with Section 16 reporting.

The filing documents an allowed conversion of Paired Interests (each consisting of Class V stock plus OpCo units) into Class A shares per the Amended and Restated Exchange Agreement, and an immediate sale of those resulting Class A shares. The Exchange Agreement permits surrender for shares or cash; here the reporting person received shares and sold them. The Form 4 is properly signed and dated by the company's secretary, reflecting standard insider reporting protocol.

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Hagerty Holding Corp.

(Last) (First) (Middle)

175 WILSON ROAD

(Street)

TRAVERSE CITY MI 49686

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Hagerty, Inc. [ HGTY ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director	X	10% Owner
	Officer (give title below)		Other (specify below)

3. Date of Earliest Transaction (Month/Day/Year)
08/13/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Class A Common Stock	08/13/2025		C		1,236,750	A	(1)	1,236,750	D
Class A Common Stock	08/13/2025		S		1,236,750	D	$8.9197	0	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Class V Common Stock	(2)	08/13/2025		C			1,236,750	(2)	(2)	Class A Common Stock	1,236,750	(1)	166,552,156	D

Explanation of Responses:

1. 1,236,750 shares of Class A Common Stock were issued in exchange for an equal number of Paired Interests (as defined below) that were surrendered by the Reporting Person pursuant to the Amended and Restated Exchange Agreement, dated as of December 2, 2021 and amended and restated as of March 23, 2022 (the "Exchange Agreement"), among the Issuer, The Hagerty Group, LLC ("OpCo"), the Reporting Person, Markel Corporation ("Markel") and each of the Reporting Person's and Markel's Qualified Transferees (as defined therein). Each "Paired Interest" consists of one share of Class V Common Stock of the Issuer and one unit of limited liability company interest of OpCo and may be surrendered by the Reporting Person pursuant to the Exchange Agreement in exchange for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, cash.

2. Each Paired Interest has no expiration date and may be surrendered by the Reporting Person pursuant to the Exchange Agreement in exchange for a share of Class A Common Stock of the Issuer or, at the option of the Issuer, cash.

	HAGERTY HOLDING CORP. By: /s/ Jessica Sullivan Name: Jessica Sullivan Title: Secretary	08/15/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

What did the Hagerty (HGTY) Form 4 report on 08/13/2025?

The Form 4 reports that the reporting person exchanged 1,236,750 Paired Interests for 1,236,750 Class A shares and sold those 1,236,750 Class A shares at $8.9197 per share on 08/13/2025.

How many shares does the reporting person own after the transactions?

After the transactions, the reporting person beneficially owns 166,552,156 Class A common shares.

What are Paired Interests mentioned in the Form 4?

Paired Interests are defined in the filing as one share of Class V common stock plus one unit of OpCo limited liability company interest; they may be surrendered under the Exchange Agreement in exchange for one Class A share or cash.

At what price were the shares sold and what are the implied proceeds?

The shares were sold at $8.9197 per share; 1,236,750 shares at that price imply gross proceeds of approximately $11.03 million (before fees and taxes).

Was the transaction executed under an agreement or plan?

Yes. The exchange was made pursuant to the Amended and Restated Exchange Agreement dated December 2, 2021 and amended March 23, 2022, as stated in the filing.