Conifer (CNFR) 13D/A: $7.5M Series B Preferred and 4M Warrants Detailed

Rhea-AI Filing Summary

Conifer Holdings, Inc. (CNFR) Schedule 13D/A discloses that Clarkston Ventures, LLC holds 3,735,769 common shares (30.6%) and Clarkston 91 West, LLC holds warrants to purchase 4,000,000 shares (24.7%). Together with individual members Jeffrey A. Hakala and Gerald W. Hakala, the group beneficially owns 7,735,769 shares or 47.7% including the warrants. Clarkston 91 West purchased 1,500 then 500 shares of newly designated Series B Preferred Stock and warrants in private transactions totaling $7,500,000. The Series B shares rank senior to common stock, carry a dividend tied to prime plus 600 basis points (with a 12% floor) and grant 3,000 votes per share subject to a 19.99% aggregate voting cap. Warrants have a $1.50 exercise price and expire January 31, 2027.

Positive

• Material equity stake disclosed: Clarkston group beneficially owns up to 47.7% of common stock including warrants.
• Committed capital: Reporting persons invested $7,500,000 to acquire Series B Preferred Stock and warrants.
• Structured protections: Series B Preferred Stock ranks senior to common and provides a defined dividend formula (prime plus 600 basis points with a 12% floor).

Negative

• Voting concentration risk: Series B Preferred Stock grants 3,000 votes per share, creating concentrated governance influence subject to a 19.99% cap.
• Potential dilution for common holders: Warrants exercisable for 4,000,000 shares at $1.50 could materially dilute existing common shareholders upon exercise.
• Senior claim on liquidation: Series B Preferred Stock ranks senior to common, which reduces residual value available to common shareholders in a liquidation.

Insights

Financial Analyst

TL;DR: A single investor group holds near-majority economic and potential voting power via shares, warrants and preferred stock.

The filing documents a material ownership position: 3,735,769 common shares and warrants for 4,000,000 shares resulting in potential combined beneficial ownership of 47.7%. The $7.5 million invested acquired Series B preferred stock that ranks senior to common and warrants exercisable at $1.50 through January 31, 2027. For investors, this ownership concentration is material because it can influence corporate decisions and capital structure outcomes. The financial terms—prime plus 600 basis points dividend with a 12% floor and a capped preferred voting block of 19.99%—create fixed senior claims and concentrated voting rights that affect common shareholders' economic and governance positions.

Corporate Governance Expert

TL;DR: Preferred stock and high-vote shares materially alter governance balance and could constrain common shareholder influence.

The Certificate of Designation grants each Series B share 3,000 votes, subject to a 19.99% aggregate cap, and senior liquidation and dividend preferences. These provisions materially change the issuer's capital and voting structure because they introduce a sizeable senior claim and a separately weighted voting class. The filing shows the investors transact via private purchase agreements and special purpose vehicles; the existence of warrants exercisable after shareholder approval further underscores a structured pathway to near-majority economic interest without immediate full dilution. This is governance-impactful and should be considered material to shareholder rights and board dynamics.

SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

SCHEDULE 13D

Under the Securities Exchange Act of 1934

(Amendment No. 5)

Conifer Holdings, Inc.

(Name of Issuer)

Common Stock, no par value

(Title of Class of Securities)

20731J102

(CUSIP Number)

Clarkston Ventures, LLC
91 West Long Lake Road,
Bloomfield Hills, MI, 48304
248-205-2254

(Name, Address and Telephone Number of Person Authorized to Receive Notices and Communications)

12/12/2024

(Date of Event Which Requires Filing of This Statement)

If the filing person has previously filed a statement on Schedule 13G to report the acquisition that is the subject of this Schedule 13D, and is filing this schedule because of §§ 240.13d-1(e), 240.13d-1(f) or 240.13d-1(g), check the following box.

The information required on the remainder of this cover page shall not be deemed to be "filed" for the purpose of Section 18 of the Securities Exchange Act of 1934 ("Act") or otherwise subject to the liabilities of that section of the Act but shall be subject to all other provisions of the Act (however, see the Notes).

SCHEDULE 13D

CUSIP No. 20731J102

1

Name of reporting person

Clarkston Ventures, LLC

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

WC

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

MICHIGAN

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 3,735,769.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 3,735,769.00

11

Aggregate amount beneficially owned by each reporting person

3,735,769.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

30.6 %

14

Type of Reporting Person (See Instructions)

PN

SCHEDULE 13D

CUSIP No. 20731J102

1

Name of reporting person

Jeffrey A. Hakala

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

AF

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

UNITED STATES

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 7,735,769.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 7,735,769.00

11

Aggregate amount beneficially owned by each reporting person

7,735,769.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

47.7 %

14

Type of Reporting Person (See Instructions)

IN

Comment for Type of Reporting Person:

Note to row 8, 10 and 11: Includes 4,000,000 shares of common stock issuable upon exercise of warrants held by Clarkston 91 West LLC.

SCHEDULE 13D

CUSIP No. 20731J102

1

Name of reporting person

Gerald W. Hakala

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

AF

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

UNITED STATES

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 7,735,769.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 7,735,769.00

11

Aggregate amount beneficially owned by each reporting person

7,735,769.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

47.7 %

14

Type of Reporting Person (See Instructions)

IN

Comment for Type of Reporting Person:

Note to row 8, 10 and 11: Includes 4,000,000 shares of common stock issuable upon exercise of warrants held by Clarkston 91 West LLC.

SCHEDULE 13D

CUSIP No. 20731J102

1

Name of reporting person

Clarkston 91 West, LLC

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

WC

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

MICHIGAN

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 4,000,000.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 4,000,000.00

11

Aggregate amount beneficially owned by each reporting person

4,000,000.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

24.7 %

14

Type of Reporting Person (See Instructions)

PN

Comment for Type of Reporting Person:

Note to row 8, 10 and 11: Includes 4,000,000 shares of common stock issuable upon exercise of warrants.

SCHEDULE 13D

Item 1.	Security and Issuer
(a)	Title of Class of Securities: Common Stock, no par value
(b)	Name of Issuer: Conifer Holdings, Inc.
(c)	Address of Issuer's Principal Executive Offices: 3001 West Big Beaver Road, Suite 319, Troy, MICHIGAN , 48084.
Item 2.	Identity and Background
(a)	This Amendment No. 5 to Schedule 13D is being filed with respect to shares of the Issuer's Common Stock held by Clarkston Ventures, LLC and a warrant to purchase shares of the Issuer's Common Stock held by Clarkston 91 West, LLC. Jeffrey A. Hakala and Gerald W. Hakala (the "Individual Members") are the members of Clarkston Ventures, LLC and Clarkston 91 West, LLC and are each deemed to have beneficial ownership over the Issuer's Common Stock owned by Clarkston Ventures, LLC and the warrant to purchase shares of the Issuer's Common Stock owned by Clarkston 91 West, LLC. Together with Clarkston Ventures, LLC and Clarkston 91 West, LLC, the Individual Members comprise a group within the meaning of Section 13(d)(3) of the Act.
(f)	Clarkston 91 West, LLC is a Michigan limited liability company
Item 3.	Source and Amount of Funds or Other Consideration
	Clarkston Ventures LLC acquired 100,000 shares of the Issuer's Common stock in a private purchase on December 12, 2024 using working capital. Clarkston 91 West, LLC purchased a warrant entitling it to purchase up to 4,000,000 shares of Common Stock on February 27, 2025 in a private purchase pursuant to a Securities Purchase Agreement using working capital of Clarkston 91 West, LLC. The warrants became exercisable upon receipt of stockholder approval on June 3, 2025.
Item 4.	Purpose of Transaction
	Clarkston Ventures, LLC purchased its 3,735,769 shares of Common Stock of the Issuer for investment purposes. Clarkston Ventures, LLC is a private special purpose vehicle and is not an operating company or public company. Clarkston 91 West LLC purchased 1,500 shares of Series B Preferred Stock of the Issuer and warrants to purchase 4,000,000 shares of common stock of the Issuer for investment purposes. See item 6 below for additional information regarding the purchases of these securities and their terms and, in particular, voting rights included therein. Clarkston 91 West LLC is a private special purpose vehicle and is not an operating company or public company.
Item 5.	Interest in Securities of the Issuer
(a)	As of the time of this filing, Clarkston Ventures, LLC owns 3,735,769 shares of the Issuer's Common Stock, or 30.6%, and Clarkston 91 West, LLC owns a warrant that entitles them to purchase 4,000,000 shares of the Issuer's Common Stock, or 24.7%. For the Individual Members, who together with Clarkston Ventures, LLC and Clarkston 91 West, LLC comprise a group within the meaning of Section 13(d)(3) of the Act, see Items 7-13 of the individual cover pages above.
(b)	See Items 7-13 of the individual cover pages above.
(c)	Clarkston Ventures LLC acquired 100,000 shares of the Issuer's Common stock in a private purchase on December 12, 2024 using working capital. Clarkston 91 West, LLC purchased a warrant entitling it to purchase up to 4,000,000 shares of Common Stock on February 27, 2025 in a private purchase pursuant to a Securities Purchase Agreement using working capital of Clarkston 91 West, LLC. The warrants became exercisable upon receipt of stockholder approval on June 3, 2025.
(d)	N/A
(e)	N/A
Item 6.	Contracts, Arrangements, Understandings or Relationships With Respect to Securities of the Issuer
	On February 27, 2025, the Issuer sold 1,000 shares of its newly designated Series B Preferred Stock, no par value (the "Series B Preferred Stock") and common stock purchase warrants (the "Warrants") exercisable for 4,000,000 shares of Common Stock (together with the Warrants and Series B Preferred Stock, the "Securities"), to Clarkston 91 West LLC ("Clarkston 91 West"), an entity affiliated with each of the Individual Members, for an aggregate purchase price of $5,000,000 pursuant to a Securities Purchase Agreement (the "Purchase Agreement"). The Warrants, which entitle Clarkston 91 West to purchase up to 4,000,000 shares of Common Stock at an exercise price of $1.50 per share, were subject to approval by the Issuer's stockholders, which was received on June 3, 2025. The Warrants will expire on January 31, 2027. On March 3, 2025, the Issuer sold an additional 500 shares of Series B Preferred Stock to Clarkston 91 West, for an aggregate purchase price of $2,500,000. The sale of these Securities was consummated pursuant to a Securities Purchase Agreement (the "Additional Purchase Agreement"). The Series B Preferred Stock were issued pursuant to a Certificate of Designation of Series B Preferred Stock to the Issuer's Second Amended and Restated Certificate of Incorporation with the Secretary of State of the State of Michigan on February 27, 2025 (the "Certificate of Designation"). The Series B Preferred Stock will rank senior to all of the common stock of the Issuer. In the event of any Liquidation Event (as defined in the Certificate of Designation), after the satisfaction in full of the debts of the Issuer and the payment of any liquidation preference owed to the holders of shares of capital stock of the Issuer ranking senior to the Series B Preferred Stock, pari passu with the holders of any Parity Securities (as defined in the Certificate of Designation) by reason of their ownership thereof, but before any distribution or payment out of the assets of the Issuer shall be made to the holders of Junior Securities (as defined in the Certificate of Designation) by reason of their ownership thereof, an amount in cash per share equal to the Series B Redemption Price (as defined below). The Series B Preferred Stock shall be entitled to a dividend at a rate equal to the prime rate of Waterford Bank, N.A. ("Waterford Bank") on the date that is 30 days prior to the applicable Dividend Payment Date (as defined in the Certificate of Designation) plus 600 basis points, provided, however, that if the prime rate determined by Waterford Bank shall ever be less than 12.0% per annum, (the "Floor" as defined in the Certificate of Designation), then the prime rate shall be deemed to be the Floor. Each share of the Series B Preferred Stock entitles the Holder to 3,000 votes on each matter properly submitted to the Issuer's shareholders for their vote, however the aggregate voting power of all outstanding shares of the Series B Preferred Stock shall not exceed 19.99% of the aggregate voting power of all voting securities. The Purchase Agreement and Additional Purchase Agreement are attached hereto as Exhibits 99.2 and 99.3, respectively. The Certificate of Designation is attached hereto as Exhibit 99.4. The form of Warrant is attached hereto as Exhibit 99.5. Except as set forth in this Schedule 13D, there are no contracts, arrangements, understandings or relationships among the Reporting Persons, or between the Reporting Persons and any other person, with respect to the securities of the Issuer.
Item 7.	Material to be Filed as Exhibits.
	Exhibit 99.1 Joint Filing Agreement Exhibit 99.2 Securities Purchase Agreement, dated February 27, 2025, by and between Conifer Holdings, Inc. and Clarkston 91 West LLC (incorporated by reference to Exhibit 10.1 to the Issuer's Current Report on Form 8-K filed with the SEC on March 4, 2025) Exhibit 99.3 Securities Purchase Agreement, dated March 3, 2025, by and between Conifer Holdings, Inc. and Clarkston 91 West LLC (incorporated by reference to Exhibit 10.3 to the Issuer's Current Report on Form 8-K filed with the SEC on March 4, 2025) Exhibit 99.4 Certificate of Designation of Series B Preferred Stock (incorporated by reference to Exhibit 3.1 to the Issuer's Current Report on Form 8-K filed with the SEC on March 4, 2025) Exhibit 99.5 Form of Warrant (incorporated by reference to Exhibit 10.2 to the Issuer's Current Report on Form 8-K filed with the SEC on March 4, 2025)

SIGNATURE

After reasonable inquiry and to the best of my knowledge and belief, I certify that the information set forth in this statement is true, complete and correct.

Clarkston Ventures, LLC

Signature:	/s/ Jeffrey A. Hakala
Name/Title:	Jeffrey A. Hakala/Member
Date:	08/22/2025

Jeffrey A. Hakala

Signature:	/s/ Jeffrey A. Hakala
Name/Title:	Jeffrey A. Hakala
Date:	08/22/2025

Gerald W. Hakala

Signature:	/s/ Gerald W. Hakala
Name/Title:	Gerald W. Hakala
Date:	08/22/2025

Clarkston 91 West, LLC

Signature:	/s/ Salvatore F. Gianino
Name/Title:	Salvatore F. Gianino, Chief Financial Officer
Date:	08/22/2025

FAQ

How much of Conifer Holdings (CNFR) does the Clarkston group beneficially own?

The Clarkston group beneficially owns 7,735,769 shares including warrants, representing 47.7% of the class as reported.

What securities did Clarkston 91 West, LLC acquire from Conifer?

Clarkston 91 West acquired Series B Preferred Stock and warrants to purchase 4,000,000 common shares under private purchase agreements for an aggregate of $7,500,000.

What are the economic rights of the Series B Preferred Stock?

Series B Preferred ranks senior to common, entitles holders to a dividend at prime plus 600 basis points with a 12% floor, and has specified liquidation preferences described in the Certificate of Designation.

What are the terms of the warrants purchased by Clarkston 91 West?

The warrants permit purchase of up to 4,000,000 common shares at an exercise price of $1.50 per share and expire on January 31, 2027.

Does the filing indicate any other agreements between the reporting persons and the issuer?

Aside from the Securities Purchase Agreement(s), the filing states no other contracts, arrangements, understandings or relationships with respect to the issuer's securities.