[Form 4] Conifer Holdings, Inc Insider Trading Activity

Rhea-AI Filing Summary

Jeffrey Anthony Hakala, a director and >10% owner of Conifer Holdings, Inc. (CNFR), reported multiple transactions across equity classes. On 08/30/2024 he disposed of 1,000 Series A preferred shares for $6,000 that are held by Clarkston 91 West LLC, an entity he partially owns. On 12/12/2024 he acquired 100,000 common shares at $2.00 each held by Clarkston Ventures, LLC, bringing the reported beneficial ownership of common stock to 3,735,769 shares (indirect). On 02/27/2025 and 03/03/2025 he reported purchases of Series B preferred shares (1,000 and 500 shares at $5,000 each) held by Clarkston 91 West LLC. He also reported a warrant transaction on 02/27/2025 for 4,000,000 warrants exercisable into common shares (exercise price $1.50) with an exercisable date of 06/03/2025 and expiration 01/31/2027, showing 4,000,000 underlying common shares held indirectly by Clarkston 91 West LLC. In each case Mr. Hakala disclaims direct beneficial ownership except to the extent of his pecuniary interest in the holding entities.

Positive

• Acquisition of 100,000 common shares at $2.00, increasing reported indirect common holdings to 3,735,769 shares
• 4,000,000 warrants reported (exercise $1.50, exercisable 06/03/2025, expiring 01/31/2027), providing clear disclosure of potential future equity exposure
• Purchases of Series B preferred (1,000 and 500 shares at $5,000 each) documented and disclosed

Negative

• Indirect ownership structure through affiliated entities (Clarkston 91 West LLC and Clarkston Ventures, LLC) limits clarity on direct economic control
• Large warrant position could result in future dilution if exercised, though the filing does not state intent to exercise

Insights

Financial Analyst

TL;DR: Insider reported significant indirect equity exposure via entity holdings and a large warrant position, increasing potential future common dilution.

The reported 4,000,000-warrant position is the most notable item because it represents potential future common shares if exercised, with a $1.50 strike and a 2027 expiration. The 100,000-common share purchase at $2.00 increases reported indirect common holdings to 3,735,769 shares. Series B preferred share purchases at $5,000 each and the earlier disposal of 1,000 Series A preferred for $6,000 are smaller in scale compared with the warrant position. All holdings are reported as indirect through affiliated entities (Clarkston 91 West LLC and Clarkston Ventures, LLC), and Mr. Hakala expressly disclaims direct beneficial ownership beyond his pecuniary interest. From an investor perspective, the warrant exposure could lead to dilution or capital infusion if exercised, but the filing does not state whether exercise or conversion is likely.

Corporate Governance Expert

TL;DR: Transactions are disclosed properly and highlight indirect ownership via affiliated vehicles; no governance red flags appear in the filing.

The Form 4 shows timely reporting of multiple equity transactions and provides the required explanations that holdings are indirect through named entities. The disclaimer of direct beneficial ownership is standard where holdings are held by related entities. There is no indication of related-party transaction terms beyond prices and quantities, and no amendments or corrections are shown. Governance implications center on transparency of control: investors should note that a director and >10% owner holds material economic exposure indirectly, but the document contains the expected disclosures and signatures.

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

OMB APPROVAL

OMB Number:			3235-0287
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hours per response:			0.5

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 Jeffrey Anthony

(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)

X	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/ Jeffrey Hakala	08/22/2025
	** 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 insider transactions did Jeffrey Hakala report for CNFR?

He reported a disposal of 1,000 Series A preferred on 08/30/2024, acquisition of 100,000 common shares on 12/12/2024 at $2.00, purchases of Series B preferred on 02/27/2025 (1,000) and 03/03/2025 (500) at $5,000 each, and a 4,000,000-warrant position on 02/27/2025.

How many common shares does the filing show Jeffrey Hakala indirectly owns?

The filing reports 3,735,769 common shares beneficially owned indirectly by Mr. Hakala.

What are the key terms of the reported warrant position?

4,000,000 warrants exercisable into common stock at $1.50, exercisable from 06/03/2025 through 01/31/2027.

Are Mr. Hakala's holdings direct or indirect according to the filing?

All reported holdings are disclosed as indirect (held by Clarkston 91 West LLC and Clarkston Ventures, LLC); Mr. Hakala disclaims direct beneficial ownership except for pecuniary interest.

Does the filing show any amendments or corrections?

No amendment dates are indicated; the form is filed as a single reporting person filing with the signature dated 08/22/2025.