Regan Michael 4

What Happened

• Regan Michael, SHF Holdings' Chief Investment & Strategy Officer, had a few related derivative transactions reported on a Form 4. The primary items: 45,875 option-based shares vested (awarded) on Sept 30, 2025 (no cash paid), and he acquired 63 shares of Series B Convertible Preferred Stock at $800 each for $50,400. He also obtained warrants to acquire up to 4,057 common shares as part of that Series B purchase. Later, the issuer redeemed one Series B preferred share on Dec 10, 2025 and another on Dec 31, 2025 for $800 each (total $1,600 returned).
• These were mostly derivative transactions (options, preferred stock, and warrants) rather than open-market buys of common stock. The option award vested upon the company meeting a financing milestone; the preferred purchase was subject to—and later received—shareholder approval.

Key Details

• Form filing date: May 8, 2026; Reported period / primary vesting date: Sept 30, 2025. Filing was reported late due to an administrative oversight (footnote F1).
• Transactions (summary):
  • Sept 30, 2025: Award vested — 45,875 shares (derivative option) @ $0.00 (vested after financing condition) — value dependent on future conversion/exercise.
  • Sept 30, 2025: Purchased 63 shares of Series B Convertible Preferred @ $800 each = $50,400 (derivative).
  • Sept 30, 2025: Received Series B warrants to initially acquire up to 4,057 common shares (recorded as 4,057 @ $0.00 in filing).
  • Dec 10, 2025: Issuer redeemed 1 share of Reporting Person's Series B Preferred @ $800 = $800.
  • Dec 31, 2025: Issuer redeemed 1 share of Reporting Person's Series B Preferred @ $800 = $800.
• Shares owned after these transactions: not specified in the provided Form 4 details here.
• Notable footnotes: F2 explains the option award was granted Aug 7, 2025 and vested 100% on Sept 30 after a financing threshold was met; F3 notes the Series B preferred & warrants purchase required shareholder approval (obtained Nov 6, 2025); F4 confirms the Series B preferred is perpetual; F5/F6 explain the redemptions on Dec 10 and Dec 31.

Context

• The 45,875 award was an option that vested due to a financing milestone — not a cash purchase or immediate sale of common stock. The 4,057 units recorded at $0 reflect warrants tied to the preferred purchase, not free common shares.
• The $50,400 purchase of Series B preferred is a direct insider investment in the company’s preferred securities; the two $800 redemptions were issuer-initiated returns of capital under the preferred terms.
• Filing was late (footnote F1); late filings can delay public visibility into insider activity but the filing discloses the relevant dates and conditions.