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SHF Holdings, Inc.·4

May 8, 9:56 PM ET

Regan Michael 4

4 · SHF Holdings, Inc. · Filed May 8, 2026

Research Summary

AI-generated summary of this filing

Updated

SHF Holdings (SHFS) CIO Regan Michael Receives Award, Buys Preferred

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.

Insider Transaction Report

Form 4
Period: 2025-09-30
SHF Holdings, Inc.SHFS
Regan Michael
Chief Inv. & Strat. Officer
Transactions
  • Award

    Stock Option (Right to Buy)

    [F1][F2]
    2025-09-30+45,875→ 45,875 total
    Exercise: $2.40From: 2025-09-30Exp: 2035-08-07→ Common Stock (45,875 underlying)
  • Purchase

    Series B Convertible Preferred Stock

    [F1][F3][F4]
    2025-09-30$800.00/sh+63$50,400→ 63 total
    Exercise: $7.76From: 2025-09-30→ Common Stock (8,114 underlying)
  • Purchase

    Series B Warrant to Purchase Common Stock (Right to Buy)

    [F1][F3]
    2025-09-30+4,057→ 4,057 total
    Exercise: $7.76From: 2026-05-11Exp: 2029-05-10→ Common Stock (4,057 underlying)
  • Other

    Series B Convertible Preferred Stock

    [F1][F5][F4]
    2025-12-10$800.00/sh−1$800→ 62 total
    Exercise: $7.76From: 2025-09-30→ Common Stock (7,986 underlying)
  • Other

    Series B Convertible Preferred Stock

    [F1][F6][F4]
    2025-12-31$800.00/sh−1$800→ 61 total
    Exercise: $7.76From: 2025-09-30→ Common Stock (7,857 underlying)
Footnotes (6)
  • [F1]This transaction is being reported late due to an inadvertent administrative oversight.
  • [F2]The Reporting Person received the stock option award on August 7, 2025. The stock option would vest 100% upon SHF Holdings, Inc.'s (the "Issuer") successful completion of an equity financing that resulted in gross proceeds to the Issuer of at least $4 million (the "Financing Vesting Condition"). The Financing Vesting Condition was satisfied on September 30, 2025 and the stock option vested 100% on that date.
  • [F3]On September 30, 2025, the Reporting Person entered into a Securities Purchase Agreement with the Issuer, pursuant to which the Issuer issued and sold to the Reporting Person 63 shares of the Issuer's Series B Convertible Preferred Stock (the "Series B Preferred Stock") and common stock purchase warrants (the "Series B Warrants") to initially acquire up to 4,057 shares of the Issuer's common stock on the same terms and conditions as the other participants in the transaction. The Reporting Person's acquisition of the Series B Preferred Stock and the Series B Warrants was subject to shareholder approval, which was obtained on November 6, 2025.
  • [F4]The Series B Preferred Stock is perpetual and therefore has no expiration date.
  • [F5]On December 10, 2025, the Issuer redeemed one share of the Reporting Person's Series B Preferred Stock in accordance with the terms of the Series B Preferred Stock's Certificate of Designation.
  • [F6]On December 31, 2025, the Issuer redeemed one share of the Reporting Person's Series B Preferred Stock in accordance with the terms of the Series B Preferred Stock's Certificate of Designation.
Signature
/s/ Michael Regan|2026-05-08

Documents

1 file
  • 4
    ownership.xmlPrimary

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