Welcome to our dedicated page for Conifer Holdings SEC filings (Ticker: CNFR), a comprehensive resource for investors and traders seeking official regulatory documents including 10-K annual reports, 10-Q quarterly earnings, 8-K material events, and insider trading forms.
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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.
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.
Clarkston Ventures, LLC reported a non-derivative purchase of 100,000 shares of Conifer Holdings, Inc. (CNFR) on 12/12/2024 at $2.00 per share. After the transaction the reporting person states ownership of 3,735,769 shares, with a disclaimer that the reporting person disclaims beneficial ownership of shares held in client accounts. The Form 4 was signed by Jeffrey A. Hakala as a member on 08/22/2025. The filing identifies the reporting person as a director and indicates the form was filed by one reporting person.
Conifer Holdings insider Clarkston 91 West LLC, reporting through member Jeffrey Hakala, purchased 500 Series B preferred shares on 03/03/2025 at a reported price of $5,000. After the transaction the reporting person beneficially owned 1,500 shares directly. The Form 4 indicates a routine purchase (code P) and is signed by the reporting person.
Conifer Holdings, Inc. (CNFR) Form 3 discloses initial beneficial ownership by Clarkston 91 West LLC, identifying the reporting person as a director. The filing shows direct ownership of 1,000 shares of Series B Preferred Stock and a direct warrant exercisable on 06/03/2025 expiring 01/31/2027 to purchase 4,000,000 shares of Common Stock at an exercise price of $1.50 per share. The event requiring the statement is dated 02/27/2025 and the form is signed by Jeffrey Hakala on 08/22/2025. The filing is an initial ownership disclosure required under Section 16.
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.
Conifer Holdings reported a return to quarterly profitability, recording net income of $2.051 million for the three months ended June 30, 2025, compared with a loss of $3.792 million in the prior-year quarter. Revenue and underwriting activity declined as the company shifted strategy and sold its wholesale agency business; net earned premiums fell to $9.564 million from $16.666 million year-over-year for the quarter. Investment holdings totaled $135.6 million and the company held $58.3 million in cash, cash equivalents and short-term investments.
The insurance subsidiaries remain large drivers of risk: unpaid losses and loss adjustment expenses were $164.6 million and Conifer recorded an accumulated deficit of $60.6 million. Management contributed capital to support CIC, raising CIC's estimated RBC to approximately 247% as of June 30, 2025. The CIS sale generated $46.6 million of cash proceeds and contingent consideration is partially recognized (the second earnout was received in Q2 2025 and a third $10.0 million earnout is valued at $7.8 million). New Series B mandatorily redeemable preferred stock of $7.5 million was issued in early 2025.
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