Hagerty Holding Corp. - 13 Aug 2025 Form 4 Insider Report for Hagerty, Inc. (HGTY)

Role: 10%+ Owner
Signature: HAGERTY HOLDING CORP. By: /s/ Jessica Sullivan Name: Jessica Sullivan Title: Secretary
Issuer symbol: HGTY
Transactions as of: 13 Aug 2025
Net transactions value: -$11,031,439
Form type: 4
Filing time: 15 Aug 2025, 21:04:27 UTC
Previous filing: 11 Aug 2025
SEC: View on sec.gov

Reporting Owners (1)

Name	Relationship	Address	Signature	Signature date	CIK
Hagerty Holding Corp.	10%+ Owner	175 WILSON ROAD, TRAVERSE CITY	HAGERTY HOLDING CORP. By: /s/ Jessica Sullivan Name: Jessica Sullivan Title: Secretary	15 Aug 2025	0001899295

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	HGTY	Class A Common Stock	Conversion of derivative security		+1,236,750			1,236,750	13 Aug 2025	Direct	F1
transaction	HGTY	Class A Common Stock	Sale	$11,031,439	-1,236,750	-100%	$8.92	0	13 Aug 2025	Direct

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	HGTY	Class V Common Stock	Conversion of derivative security		-1,236,750	-0.74%		166,552,156	13 Aug 2025	Class A Common Stock	1,236,750		Direct	F1, F2

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	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.
F2	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.

Content

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.

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.