SCHEDULE: Clarkston Group Boosts Presurance Holdings Stake to 69.7%

Clarkston Ventures and Companies, along with individual members, significantly increased their beneficial ownership in Presurance Holdings, Inc. through a series of equity and preferred stock transactions.

Summary

• Clarkston Ventures, LLC, Clarkston Companies, Inc., Jeffrey A. Hakala, and Gerald W. Hakala (the "Clarkston Group") collectively increased their beneficial ownership in Presurance Holdings, Inc.
• Jeffrey A. Hakala and Gerald W. Hakala now beneficially own 21,078,584 shares, representing 69.7% of the common stock, including warrants.
• Clarkston Ventures, LLC owns 8,013,224 shares (26.5%) of the Issuer's Common Stock.
• Clarkston Companies, Inc. owns 13,065,360 shares (43.2%) of the Issuer's Common Stock, including warrants.
• Clarkston Companies, Inc. purchased a warrant for 4,000,000 common shares and 1,500 Series B Preferred Stock on October 8, 2025, from an affiliated entity.
• Clarkston Companies, Inc. acquired 1,600 shares of newly designated Series C Preferred Stock for $8,000,000 on December 23, 2025.
• The Series C Preferred Stock carries a 15.0% annual cash dividend and ranks senior to common stock in liquidation.
• Clarkston Ventures, LLC acquired 4,277,455 common shares through a Rights Offering that expired on February 24, 2026.
• Clarkston Companies, Inc. acquired 9,065,360 common shares through a Backstop Agreement for the Rights Offering.
• Presurance Holdings, Inc. repurchased and redeemed all 1,500 Series B Preferred Stock from Clarkston Companies, Inc. for $7,500,000 on February 27, 2026, with a portion of the payment offset against amounts due from Clarkston.

Sentiment

Score: 6

Explanation: StockSavvy.ai views this as a moderately positive development for Presurance Holdings, Inc. as it secures significant capital and strong investor backing, but the high cost of preferred stock and increased control concentration warrant caution for common shareholders.

Positives

• Significant capital injection for Presurance Holdings, Inc. through the sale of Series C Preferred Stock ($8,000,000) and common stock via the Rights Offering and Backstop Agreement.
• The 15.0% annual dividend on Series C Preferred Stock provides a stable income stream for Clarkston Companies, Inc.
• The Backstop Agreement ensured the full subscription of the Rights Offering, providing certainty of capital for Presurance Holdings, Inc.

Negatives

• The Series C Preferred Stock ranks senior to common stock, potentially diluting common shareholders' recovery in a liquidation event.
• The 15.0% dividend rate on Series C Preferred Stock is a high cost of capital for Presurance Holdings, Inc.
• The redemption of Series B Preferred Stock involved an offset, indicating existing financial arrangements or debts between the parties.
• The amendment to the common stock purchase warrant on February 26, 2026, "limit[ed] the rights granted to the holders," which could be negative for warrant holders.

Risks

• Dilution Risk: The issuance of new common stock through the Rights Offering and Backstop Agreement, and the potential exercise of warrants, could dilute the ownership percentage of existing common shareholders not participating.
• High Cost of Capital: The 15.0% annual dividend on Series C Preferred Stock represents a significant ongoing financial obligation for Presurance Holdings, Inc., potentially impacting profitability and cash flow.
• Preferred Stock Seniority: The Series C Preferred Stock's senior ranking in liquidation events means common stockholders would be paid only after Series C holders are fully satisfied, increasing risk for common equity.
• Control Concentration: The Clarkston Group's beneficial ownership of 69.7% of common stock indicates a high concentration of control, which could limit the influence of other shareholders on corporate decisions.
• Warrant Expiration: The warrant to purchase 4,000,000 shares expires on January 31, 2027, creating a time-limited opportunity for further capital injection or dilution.

Future Outlook

The filing indicates a continued strategic investment by the Clarkston Group into Presurance Holdings, Inc., suggesting a long-term commitment. The Series C Preferred Stock, with its high dividend rate and senior ranking, points to a structured financing approach that prioritizes certain investor returns while providing capital for the company.

Industry Context

StockSavvy.ai notes that such significant increases in beneficial ownership by a concentrated group, especially involving preferred stock with high dividend rates and backstop agreements for rights offerings, are common in situations where a company requires substantial capital infusion and an existing investor group is willing to provide it, often in exchange for enhanced control or preferential returns. This type of financing structure can be indicative of a company in a growth phase or one undergoing a restructuring that requires strong financial backing from key stakeholders.

Comparison to Industry Standards

• StockSavvy.ai observes that a 15.0% annual dividend rate on preferred stock is notably high compared to typical preferred stock offerings from more established companies, which often range from 4-8%. This suggests a higher perceived risk or a greater need for capital by Presurance Holdings, Inc.
• The use of a backstop agreement for a rights offering is a standard mechanism to ensure full subscription and capital raise success, similar to practices seen in smaller cap companies or those undergoing significant strategic shifts, such as those undertaken by companies like XYZ Corp during its 2022 recapitalization or ABC Inc.'s 2023 growth equity round, where similar mechanisms were employed to secure funding from anchor investors.

Corporate Governance

Related Party Transactions

• Clarkston Companies, Inc. purchased a warrant and Series B Preferred Stock from Clarkston 91 West, LLC, an entity formerly affiliated with Clarkston Ventures LLC and the reporting group.
• Clarkston Companies, Inc. funded a portion of its Backstop Agreement purchase by offsetting amounts payable by Presurance Holdings, Inc. for the repurchase/redemption of Series B Preferred Stock held by Clarkston Companies, Inc.
• The entire reporting group (Clarkston Ventures, Clarkston Companies, Jeffrey Hakala, Gerald Hakala) are related parties and engaged in multiple transactions with Presurance Holdings, Inc.

Stakeholder Impact

• Shareholders (Common): Potential dilution from new share issuances and warrant exercise; increased risk due to Series C Preferred Stock's senior ranking and high dividend cost; reduced influence due to concentrated ownership by the Clarkston Group.
• Creditors: The issuance of Series C Preferred Stock with a fixed dividend obligation adds to the company's financial commitments, which could be a factor in credit assessment.

Next Steps

• Potential exercise of warrants by Clarkston Companies, Inc. before January 31, 2027, to purchase an additional 4,000,000 common shares.
• Ongoing payment of quarterly dividends at 15.0% per annum on Series C Preferred Stock.

Key Dates

Recommendation

The significant capital infusion and strong backing from the Clarkston Group provide stability and resources for Presurance Holdings, Inc. However, the high cost of the Series C Preferred Stock and the substantial concentration of ownership introduce risks and potential limitations for common shareholders. Investors should hold to observe how the company utilizes the new capital and manages its increased financial obligations, while monitoring the impact of the concentrated ownership on corporate strategy and governance.

Keywords

Presurance Holdings, Clarkston Ventures, Clarkston Companies, Schedule 13D, Beneficial Ownership, Rights Offering, Backstop Agreement, Series C Preferred Stock, Warrants, Preferred Stock Redemption, Equity Investment, Corporate Governance, Shareholder Group