[Form 4] Conifer Holdings, Inc Insider Trading Activity

Rhea-AI Filing Summary

Gerald W. Hakala, a director of Conifer Holdings, Inc. (CNFR), reported multiple transactions across 2024–2025 involving preferred stock, common stock and warrants. The filing shows a disposition of 1,000 Series A Preferred shares on 08/30/2024 with a reported price of $6,000. It also shows purchases of equity: 100,000 common shares on 12/12/2024 at $2.00 per share, 1,000 Series B Preferred shares on 02/27/2025 at $5,000 each, and 500 Series B Preferred shares on 03/03/2025 at $5,000 each. In addition, a warrant to purchase 4,000,000 common shares with a $1.50 exercise price was acquired on 02/27/2025 (exercisable 06/03/2025, expiring 01/31/2027). Reported holdings are held indirectly through Clarkston 91 West LLC and Clarkston Ventures, LLC, in which Mr. Hakala disclaims beneficial ownership except to his pecuniary interest.

Insights

Financial Analyst

TL;DR: Multiple insider purchases and a sizable warrant position increase potential equity exposure but reflect transactions by affiliated entities, not direct personal holdings.

The filing documents material equity purchases and a large warrant arrangement held by entities affiliated with Mr. Hakala. The acquisition of 100,000 common shares at $2.00 and a warrant covering 4,000,000 common shares with a $1.50 strike are notable for potential dilution and future equity leverage. Preferred series transactions show purchases at substantially higher per-share values ($5,000 each for Series B) versus the Series A disposition reported at $6,000. All securities are held indirectly by Clarkston 91 West LLC and Clarkston Ventures, LLC, and Mr. Hakala disclaims beneficial ownership except to his pecuniary interest, which affects direct control interpretation.

Corporate Governance Expert

TL;DR: Routine Section 16 disclosure of affiliated-entity transactions; governance implications are limited since holdings are indirect.

From a governance standpoint, timely disclosure of acquisitions and disposals complies with Section 16 reporting obligations. The fact that holdings are reported as indirect and disclosed with disclaimers reduces immediate concerns about personal concentrated ownership changes by the director. The warrant exercisability window and expiration are disclosed, which is important for transparency. No amendments or corrections are noted and signature is dated 08/22/2025, providing a clear filing record.

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^*

Hakala Gerald W

(Last) (First) (Middle)

3001 WEST BIG BEAVER ROAD

SUITE 319

(Street)

TROY MI 48084

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Conifer Holdings, Inc. [ CNFR ]

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)
08/30/2024

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
Series A Preferred Stock	08/30/2024		D		1,000	D	$6,000	0	I	Held by Clarkston 91 West LLC(1)
Common Stock	12/12/2024		P		100,000	A	$2	3,735,769	I	Held by Clarkston Ventures, LLC(2)
Series B Preferred Stock	02/27/2025		P		1,000	A	$5,000	1,000	I	Held by Clarkston 91 West LLC(1)
Series B Preferred Stock	03/03/2025		P		500	A	$5,000	500	I	Held by Clarkston 91 West LLC(1)

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
Warrant to Purchase Common Stock	$1.5	02/27/2025		P		4,000,000		06/03/2025	01/31/2027	Common Stock	4,000,000	$0	4,000,000	I	Held by Clarkston 91 West LLC(1)

Explanation of Responses:

1. The securities are held directly by Clarkston 91 West LLC ("C91") and indirectly by Mr. Hakala as a shareholder of the parent company of C91. Mr. Hakala disclaims beneficial ownership in the securities held by C91 except to the extent of his pecuniary ownership therein.

2. The securities are held directly by Clarkston Ventures, LLC ("CV") and indirectly by Mr. Hakala as a partner of CV. Mr. Hakala disclaims beneficial ownership in the securities held by CV except to the extent of his pecuniary ownership therein.

	/s/ Gerald W. Hakala	08/22/2025
	** Signature of Reporting Person	Date
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