Form 4: Pineapple Financial COO Boosts Stake with Significant Share Acquisitions

Pineapple Financial Inc.'s Chief Operating Officer, Kendall Leo Marin, has substantially increased his direct beneficial ownership in the company through a series of common share purchases in mid-July 2025.

Summary

• Kendall Leo Marin, COO, Director, and 10% Owner of Pineapple Financial Inc. (PAPL), reported multiple direct purchases of common shares.
• On July 11, 2025, Marin acquired 1,000 common shares at a price of $0.1 per share.
• On July 14, 2025, Marin acquired a total of 7,000 common shares, consisting of 4,000 shares at $0.095 each and 3,000 shares at $0.09 each.
• On July 15, 2025, Marin acquired a total of 81,000 common shares, comprising 12,000 shares at $0.089 each, 1,000 shares at $0.1 each, and 68,000 shares at $0.095 each.
• Following these transactions, Marin's direct beneficial ownership of common shares increased to 2,380,923.
• The reported total beneficial ownership excludes 126,652 stock options and 25,651 warrants held by Marin.
• The stock options were granted on November 03, 2023, under the 2022 Omnibus Equity Incentive Compensation Plan, exercisable at $3.60 per share, with 25% vesting on the grant date and the remainder vesting in equal installments every 6 months over 2 years.

Sentiment

Score: 8

Explanation: The significant insider buying by a key executive and major shareholder is a strong positive signal, indicating management's belief in the company's value and future performance, despite the low share price.

Positives

• A key insider, the Chief Operating Officer, Director, and 10% Owner, significantly increased his direct ownership in the company, signaling strong confidence in future prospects.
• The acquisition of 89,000 common shares demonstrates a tangible commitment from management.

Negatives

• The purchase prices for the common shares ranged from $0.089 to $0.1, indicating a very low current stock valuation for Pineapple Financial Inc.

Risks

• No specific risks were detailed in this Form 4 filing, as it primarily reports insider transactions.

Future Outlook

The stock options granted to Kendall Marin on November 03, 2023, are set to continue vesting over a two-year period, with remaining unvested options vesting in equal installments every six months.

Management Comments

• The direct purchase of a significant number of common shares by COO Kendall Leo Marin implicitly signals strong confidence in Pineapple Financial Inc.'s current valuation and future prospects.

Industry Context

This Form 4 filing reflects a standard insider transaction, where a key executive and significant shareholder increases their stake. Such actions are often interpreted by the market as a positive signal, indicating management's belief in the company's intrinsic value and future performance, especially in the financial services or fintech sector where Pineapple Financial operates.

Comparison to Industry Standards

• Not directly applicable as this is a report of specific insider share purchases rather than company-wide financial performance or operational metrics. Insider buying, however, is generally viewed positively across all industries as a sign of management confidence.

Corporate Governance

Related Party Transactions

• Kendall Leo Marin, as COO, Director, and 10% Owner, directly purchased common shares of Pineapple Financial Inc., which constitutes a related party transaction.

Stakeholder Impact

• Shareholders may view the insider buying as a positive indicator of future stock performance and management confidence, potentially increasing investor trust.
• Employees may perceive increased stability and confidence from leadership, which could positively impact morale.

Next Steps

• Continued vesting of Kendall Marin's stock options, with installments every 6 months over the remaining period of the 2-year vesting schedule.

Key Dates

Recommendation

Keywords

Pineapple Financial, PAPL, SEC Form 4, Insider Trading, Share Purchase, Beneficial Ownership, Kendall Marin, COO, Equity Incentive Plan, Stock Options, Warrants