Kay Jeffrey R. 4

What Happened

• Jeffrey R. Kay, Chief Marketing Officer of SHF Holdings (SHFS), acquired 63 shares of the company's Series B Convertible Preferred Stock on 2025-09-30 at $800.00 per share for a total of $50,400. At the same time he received Series B warrants to initially acquire up to 4,057 shares of common stock (warrants reported at $0). The preferred shares are perpetual (no expiration). Later, the issuer redeemed one of his Series B preferred shares on 2025-12-10 for $800 and redeemed another on 2025-12-31 for $800 in each case under the Certificate of Designation.

Key Details

• Transaction dates/prices:
  • 2025-09-30: Purchased 63 Series B preferred shares @ $800.00 = $50,400 (plus Series B warrants to acquire up to 4,057 common shares, reported at $0).
  • 2025-12-10: Issuer redeemed 1 Series B preferred share @ $800.00 (disposition).
  • 2025-12-31: Issuer redeemed 1 Series B preferred share @ $800.00 (disposition).
• Shares owned after the reported transactions: not disclosed on the Form 4.
• Notable footnotes:
  • F1: The Form 4 was filed late due to an inadvertent administrative oversight.
  • F2: Purchase was pursuant to a Securities Purchase Agreement; the Series B preferred and warrants were issued subject to shareholder approval (approval obtained 2025-11-06).
  • F3: Series B preferred stock is perpetual (no expiration).
  • F4–F5: The December redemptions were made by the issuer under the Certificate of Designation.
• Timeliness: Filing was reported late (administrative oversight). Late filings can delay public disclosure but do not by themselves indicate the substance or intent of the trades.

Context

• These were derivative/security transactions (preferred stock and warrants), not a routine open-market common-stock buy; the purchase included both preferred shares and warrants to acquire common shares on the same terms as other participants in the offering.
• Redemptions were actions by the company under the preferred stock terms (not open-market sales by the insider).