SHF Holdings (SHFS) officer buys Series B stake, receives large option
Filing Impact
Filing Sentiment
Form Type
4
Rhea-AI Filing Summary
SHF Holdings, Inc. Chief Investment & Strategy Officer Michael Regan reported several 2025 equity-linked transactions. On September 30, 2025, he entered a Securities Purchase Agreement under which the company issued 63 shares of Series B Convertible Preferred Stock at $800 per share and Series B Warrants initially exercisable for 4,057 common shares at $7.7644, on the same terms as other participants, subject to shareholder approval obtained on November 6, 2025. That day he also held a previously granted stock option for 45,875 common shares at $2.40, which vested 100% when the company completed an equity financing with at least $4 million in gross proceeds on September 30. The company later redeemed one Series B Preferred share on December 10, 2025 and another on December 31, 2025, leaving 61 Series B Preferred shares. The filing notes it was reported late due to an administrative oversight.
Positive
- None.
Negative
- None.
Insider Trade Summary
Net Buyer: 4,120 shares ($50,400)
Net Buy
5 txns
Insider
Regan Michael
Role
Chief Inv. & Strat. Officer
Bought
4,120 shs ($50K)
| Type | Security | Shares | Price | Value |
|---|---|---|---|---|
| Other | Series B Convertible Preferred Stock | 1 | $800.00 | $800.00 |
| Other | Series B Convertible Preferred Stock | 1 | $800.00 | $800.00 |
| Grant/Award | Stock Option (Right to Buy) | 45,875 | $0.00 | -- |
| Purchase | Series B Convertible Preferred Stock | 63 | $800.00 | $50K |
| Purchase | Series B Warrant to Purchase Common Stock (Right to Buy) | 4,057 | $0.00 | -- |
Holdings After Transaction:
Series B Convertible Preferred Stock — 61 shares (Direct, null);
Stock Option (Right to Buy) — 45,875 shares (Direct, null);
Series B Warrant to Purchase Common Stock (Right to Buy) — 4,057 shares (Direct, null)
Footnotes (1)
- This transaction is being reported late due to an inadvertent administrative oversight. 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. 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. The Series B Preferred Stock is perpetual and therefore has no expiration date. 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. 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.
Key Figures
Series B Preferred purchase: 63 shares at $800
Series B Warrant position: 4,057 shares at $7.7644
Stock option grant: 45,875 shares at $2.40
+3 more
6 metrics
Series B Preferred purchase
63 shares at $800
Purchased September 30, 2025 under Securities Purchase Agreement
Series B Warrant position
4,057 shares at $7.7644
Warrants to buy common stock acquired September 30, 2025
Stock option grant
45,875 shares at $2.40
Option award vesting fully on September 30, 2025
Financing vesting trigger
$4 million gross proceeds
Equity financing required for option vesting, satisfied September 30, 2025
Series B redemptions
1 share each date
Redemptions on December 10 and December 31, 2025
Series B Preferred remaining
61 shares
Holdings after redemptions as of December 31, 2025
Key Terms
Series B Convertible Preferred Stock, Series B Warrants, Securities Purchase Agreement, equity financing, +1 more
5 terms
Series B Convertible Preferred Stock financial
"63 shares of the Issuer's Series B Convertible Preferred Stock"
Series B convertible preferred stock is a class of shares sold during a later-stage private financing that combines features of a loan and common stock: it usually pays priority dividends or has a priority claim if the company is sold, and it can be converted into common shares under predefined rules. Investors care because these shares affect ownership stakes and payout order—like having a reserved place in line and a ticket that can turn into regular ownership—so they influence potential returns and dilution for other shareholders.
Series B Warrants financial
"common stock purchase warrants (the "Series B Warrants") to initially acquire up to 4,057 shares"
Series B warrants are contracts issued alongside a company's Series B financing that give the holder the right to buy a set number of shares at a fixed price within a specified time. For investors, they matter because they can provide leveraged upside if the company grows, or they can dilute existing shareholders when exercised—like a coupon promising a future share at a known price that can add value or change ownership stakes.
Securities Purchase Agreement financial
"the Reporting Person entered into a Securities Purchase Agreement with the Issuer"
A securities purchase agreement is a written contract between a buyer and a seller outlining the terms for buying or selling financial assets such as stocks or bonds. It specifies details like the price, quantity, and conditions of the transaction, similar to a shopping list with agreed-upon terms. For investors, it provides clarity and legal protection when transferring ownership of these financial instruments.
equity financing financial
"successful completion of an equity financing that resulted in gross proceeds to the Issuer of at least $4 million"
Equity financing is when a company raises money by selling ownership pieces (shares) to investors instead of borrowing; think of selling slices of a pie to get cash for the business. It matters to investors because buying shares gives them a claim on future profits and a voice in decisions, while existing owners give up some control and the value of each slice can change as the company grows or falters.
Certificate of Designation financial
"in accordance with the terms of the Series B Preferred Stock's Certificate of Designation"
A certificate of designation is a formal document that spells out the specific rights and rules attached to a particular class or series of stock, usually preferred shares. Think of it as a rulebook or menu that lists dividend terms, liquidation priority, conversion or redemption rights and any special voting protections; investors use it to judge how much income, control or downside protection those shares will provide compared with other securities.
FAQ
What insider transactions did SHF Holdings (SHFS) report for Michael Regan?
SHF Holdings reported that officer Michael Regan acquired 63 Series B Convertible Preferred shares at $800 each, Series B Warrants for 4,057 common shares, and a stock option for 45,875 shares at $2.40, along with two later redemptions of one preferred share each.
How did the $4 million financing affect Michael Regan’s SHFS stock option?
Regan’s stock option for 45,875 SHF Holdings common shares at $2.40 vested 100% when the company completed an equity financing with at least $4 million in gross proceeds on September 30, 2025, satisfying the defined Financing Vesting Condition in the award terms.
What were the terms of Michael Regan’s Series B investments in SHF Holdings (SHFS)?
On September 30, 2025, Regan bought 63 Series B Convertible Preferred shares at $800 each and Series B Warrants initially exercisable for 4,057 common shares at $7.7644, on the same terms as other participants, subject to shareholder approval obtained November 6, 2025.
What redemptions of SHF Holdings Series B Preferred Stock were reported?
SHF Holdings redeemed one share of Regan’s Series B Convertible Preferred Stock on December 10, 2025, and another share on December 31, 2025, in each case under the Series B Certificate of Designation, reducing his Series B Preferred holdings from 63 shares to 61 shares.
Was the Form 4 for SHF Holdings (SHFS) insider Michael Regan filed on time?
No. A footnote states the transaction was reported late because of an inadvertent administrative oversight. This explanation accompanies the detailed disclosure of his 2025 preferred stock, warrant, and stock option transactions with SHF Holdings.