Conifer Holdings SEC Filings

Presurance Holdings, Inc. reported a smaller loss from continuing operations in Q3 2025 as it reshaped its underwriting and strengthened capital at its primary insurer. The company posted a net loss of $3.97 million for the quarter, compared with a $6.89 million loss a year ago, as net earned premiums fell to $6.82 million from $14.60 million with commercial lines largely in run‑off and focus on specialty homeowners.

Total revenue and other income were $6.68 million, while losses and LAE declined to $6.39 million from $15.15 million. Shareholders’ equity increased to $25.30 million from $21.53 million at year‑end, helped by unrealized gains. Assets were $285.0 million.

Liquidity remains tight at the parent company level with $0.894 million in cash at September 30, 2025, quarterly public debt interest of about $412,000, and Series B preferred dividends. The insurer subsidiary TIC’s estimated RBC ratio improved to ~261% after a $6.5 million capital contribution and a new 50% homeowners quota share effective June 1, 2025. Presurance has 9.75% senior notes due 2028 outstanding ($16.9 million gross; $12.12 million net on the balance sheet) and $7.5 million of mandatorily redeemable Series B Preferred issued with 4,000,000 warrants at $1.50.

Clarkston 91 West LLC reported the disposition of certain securities of Presurance Holdings, Inc. (PRHI) on 10/08/2025. The filing shows a sale/disposition of 1,500 Series B preferred shares (reported price $5,000) leaving 0 Series B shares beneficially owned. The filing also reports a disposition of 4,000,000 warrants to purchase common stock (exercise price $1.50, expiration 01/31/2027) with 0 underlying common shares retained. The reporting person is listed as a Director and 10% owner; the form is signed by Jeffrey Hakala.

Reporting person Clarkston Companies, Inc. filed an initial Form 3 disclosing ownership in Presurance Holdings, Inc. (PRHI). The filing shows 1,500 shares of Series B Preferred Stock held directly and a direct warrant to purchase 4,000,000 shares of common stock exercisable at $1.50. The warrant becomes exercisable on 06/03/2025 and expires on 01/31/2027. The form is signed by Jeffrey Hakala on 10/09/2025.

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.