Direct Digital Holdings President Acquires 185,000 Shares Through Unit Conversion

Keith W. Smith, President, Director, and 10% Owner of Direct Digital Holdings (DRCT), reported significant securities transactions on June 18, 2025.

Rhea-AI Filing Summary

Keith W. Smith, President, Director, and 10% Owner of Direct Digital Holdings (DRCT), reported significant securities transactions on June 18, 2025. The filing details two key transactions:

• Acquisition of 185,000 shares of Class A Common Stock (indirect ownership through SKW Financial LLC)
• Conversion of 185,000 Class A Common Units of Direct Digital Holdings LLC (held indirectly through Direct Digital Management, LLC)

Following these transactions, Smith's holdings include 66,370 shares held directly and 5,194,000 derivative securities through Direct Digital Management, LLC. The Class A Common Units are exchangeable for Class A Common Stock on a one-for-one basis, with concurrent cancellation of corresponding Class B Common Stock shares. This transaction reflects a significant insider position change and demonstrates continued executive investment in the company.

Insider Trade Summary

185,000 shares exercised/converted

Exercise 3 txns

Insider SMITH W KEITH

Role President

Type	Security	Shares	Price	Value
Conversion	Class A Common Units of Direct Digital Holdings LLC	185,000	$0.00	$0.00
Conversion	Class A Common Stock, par value $0.001 per share	185,000	$0.00	$0.00
holding	Class A Common Stock, par value $0.001 per share	--	--	--

Holdings After Transaction: Class A Common Units of Direct Digital Holdings LLC — 5,194,000 contracts (Indirect, By Direct Digital Management, LLC); Class A Common Stock, par value $0.001 per share — 185,000 shares (Indirect, By SKW Financial LLC); Class A Common Stock, par value $0.001 per share — 66,370 shares (Direct)

Footnotes (1)

1. F1. Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings, LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person (indirectly through the Reporting Person's ownership interest in Direct Digital Management, LLC) are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

FAQ

AI-generated questions and answers. How Rhea-AI works. Not financial advice.

What insider transaction did DRCT's Keith Smith report on June 18, 2025?

Keith Smith, who serves as President, Director, and 10% Owner of DRCT, acquired 185,000 shares of Class A Common Stock indirectly through SKW Financial LLC. This transaction was related to the conversion of Class A Common Units of Direct Digital Holdings LLC.

How many DRCT shares does Keith Smith own directly after the reported transaction?

Following the reported transaction, Keith Smith directly owns 66,370 shares of DRCT Class A Common Stock.

What is the total indirect ownership of DRCT Class A Common Units held by Keith Smith through Direct Digital Management, LLC?

After the reported transaction, Keith Smith indirectly owns 5,194,000 Class A Common Units of Direct Digital Holdings LLC through Direct Digital Management, LLC.

What is the exchange ratio for DRCT's Class A Common Units to Class A Common Stock?

According to the filing, Class A Common Units are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. When exchanged, an equal number of Class B Common Stock shares are cancelled.

What positions does Keith Smith hold at Direct Digital Holdings (DRCT)?

Keith Smith holds multiple positions at DRCT: President, Director, and is also a 10% Owner of the company.

AI-generated analysis. How Rhea-AI works. Not financial advice.

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Accepted by SEC EDGAR 06/20/2025 - 04:12 PM Learn about SEC filing dates

SEC Form 4

FORM 4

UNITED 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^*

SMITH W KEITH

(Last) (First) (Middle)

C/O DIRECT DIGITAL HOLDINGS, INC.

1177 WEST LOOP SOUT, SUITE 1300

(Street)

HOUSTON TX 77027

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Direct Digital Holdings, Inc. [ DRCT ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director	X	10% Owner
X	Officer (give title below)		Other (specify below)
	President

3. Date of Earliest Transaction (Month/Day/Year)
06/18/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

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)
			Code	V	Amount	(A) or (D)	Price
Class A Common Stock, par value $0.001 per share	06/18/2025		C		185,000	A	(1)	185,000	I	By SKW Financial LLC
Class A Common Stock, par value $0.001 per share								66,370	D

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)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Class A Common Units of Direct Digital Holdings LLC	(1)	06/18/2025		C			185,000	(1)	(1)	Class A Common Stock, par value $0.001 per share	185,000	$0	5,194,000	I	By Direct Digital Management, LLC

Explanation of Responses:

1. Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings, LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person (indirectly through the Reporting Person's ownership interest in Direct Digital Management, LLC) are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

Remarks:

	/s/ Mark Walker, attorney-in-fact for Keith W. Smith	06/18/2025
	** Signature of Reporting Person	Date
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.