STOCK TITAN

Insider Jeffrey Kay adds SHF Holdings (SHFS) Series B preferred and warrants

Filing Impact
(Neutral)
Filing Sentiment
(Positive)
Form Type
4

Rhea-AI Filing Summary

SHF Holdings, Inc. Chief Marketing Officer Jeffrey R. Kay reported multiple transactions in Series B securities. 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 to buy 4,057 shares of common stock at a conversion price of $7.7644 per share, with the warrants expiring on May 10, 2029. The acquisition was subject to shareholder approval obtained on November 6, 2025. The Series B Preferred Stock is perpetual. The company later redeemed one preferred share on December 10, 2025 and another on December 31, 2025, leaving Kay with 61 Series B preferred shares. The filing notes the transactions were reported late due to an administrative oversight.

Positive

  • None.

Negative

  • None.
Insider Kay Jeffrey R.
Role Chief Marketing 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
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); Series B Warrant to Purchase Common Stock (Right to Buy) — 4,057 shares (Direct, null)
Footnotes (1)
  1. This transaction is being reported late due to an inadvertent administrative oversight. On September 30, 2025, the Reporting Person entered into a Securities Purchase Agreement with SHF Holdings, Inc. (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.
Series B preferred purchased 63 shares at $800 per share Acquired under Securities Purchase Agreement on September 30, 2025
Series B warrants acquired 4,057 warrants Right to buy common stock at $7.7644 per share
Warrant exercise price $7.7644 per share Exercise price for Series B Warrants
Warrant expiry May 10, 2029 Expiration date of Series B Warrants
Preferred shares after redemptions 61 shares Total Series B Convertible Preferred Stock following December 31, 2025 redemption
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"
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
"entered into a Securities Purchase Agreement with SHF Holdings, Inc."
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.
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.
redemed financial
"the Issuer redeemed one share of the Reporting Person's Series B Preferred Stock"
SEC Form 4
FORM 4UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940
OMB APPROVAL
OMB Number:3235-0287
Estimated average burden
hours per response:0.5
Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.
1. Name and Address of Reporting Person*
Kay Jeffrey R.

(Last)(First)(Middle)
1526 COLE BLVD,
SUITE 250

(Street)
GOLDEN COLORADO 80401

(City)(State)(Zip)

UNITED STATES

(Country)
2. Issuer Name and Ticker or Trading Symbol
SHF Holdings, Inc. [ SHFS ]
5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
Director10% Owner
XOfficer (give title below)Other (specify below)
Chief Marketing Officer
2a. Foreign Trading Symbol
3. Date of Earliest Transaction (Month/Day/Year)
09/30/2025
6. Individual or Joint/Group Filing (Check Applicable Line)
XForm filed by One Reporting Person
Form filed by More than One Reporting Person
4. If Amendment, Date of Original Filed (Month/Day/Year)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3) 2. Transaction Date (Month/Day/Year)2A. Deemed Execution Date, if any (Month/Day/Year)3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeVAmount(A) or (D)Price
Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3) 2. Conversion or Exercise Price of Derivative Security 3. Transaction Date (Month/Day/Year)3A. Deemed Execution Date, if any (Month/Day/Year)4. Transaction Code (Instr. 8) 5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 6. Date Exercisable and Expiration Date (Month/Day/Year)7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4) 8. Price of Derivative Security (Instr. 5) 9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4) 10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 11. Nature of Indirect Beneficial Ownership (Instr. 4)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
Series B Convertible Preferred Stock$7.764409/30/2025(1)(2)P6309/30/2025 (3)Common Stock8,114$80063D
Series B Warrant to Purchase Common Stock (Right to Buy)$7.764409/30/2025(1)(2)P4,05705/11/202605/10/2029Common Stock4,057$04,057D
Series B Convertible Preferred Stock$7.764412/10/2025(1)J(4)109/30/2025 (3)Common Stock7,986$80062D
Series B Convertible Preferred Stock$7.764412/31/2025(1)J(5)109/30/2025 (3)Common Stock7,858$80061D
Explanation of Responses:
1. This transaction is being reported late due to an inadvertent administrative oversight.
2. On September 30, 2025, the Reporting Person entered into a Securities Purchase Agreement with SHF Holdings, Inc. (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.
3. The Series B Preferred Stock is perpetual and therefore has no expiration date.
4. 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.
5. 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.
/s/ Jeffrey R. Kay05/08/2026
** Signature of Reporting PersonDate
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.
* Form 4: SEC 1474 (03-26)

FAQ

What did SHF Holdings (SHFS) insider Jeffrey R. Kay buy?

Jeffrey R. Kay acquired 63 shares of Series B Convertible Preferred Stock at $800 per share and Series B Warrants to purchase 4,057 shares of common stock, all under a Securities Purchase Agreement subject to shareholder approval.

What are the key terms of the Series B Warrants at SHF Holdings (SHFS)?

The Series B Warrants initially allow purchase of 4,057 common shares at a $7.7644 per share exercise price. They become exercisable on May 11, 2026 and expire on May 10, 2029, according to the reported Form 4 transactions.

Is the SHF Holdings (SHFS) Series B Convertible Preferred Stock perpetual?

Yes. The filing states the Series B Convertible Preferred Stock is perpetual and therefore has no expiration date. However, the company may redeem shares, as shown by the redemptions of one share each on December 10 and December 31, 2025.

How many Series B preferred shares does Jeffrey R. Kay hold after these SHFS transactions?

After purchasing 63 Series B preferred shares and subsequent issuer redemptions of one share on December 10 and one on December 31, 2025, Jeffrey R. Kay holds 61 shares of Series B Convertible Preferred Stock, based on the totals reported following each transaction.

Were the SHF Holdings (SHFS) insider transactions reported on time?

No. A footnote explains that at least one transaction was reported late due to an inadvertent administrative oversight. This comment refers to the timing of the Form 4 filing rather than the economic terms of the insider’s transactions.

Did SHF shareholders approve Jeffrey R. Kay’s Series B securities purchase?

Yes. The filing notes his acquisition of Series B Preferred Stock and Series B Warrants was subject to shareholder approval, which was obtained on November 6, 2025. This approval allowed the transaction terms under the Securities Purchase Agreement to become effective.