KEITH W. SMITH - 18 Jun 2025 Form 4 Insider Report for Direct Digital Holdings, Inc. (DRCT)

Role: President, Director, 10%+ Owner
Signature: /s/ Mark Walker, attorney-in-fact for Keith W. Smith
Issuer symbol: DRCT
Transactions as of: 18 Jun 2025
Transactions value $: $0
Form type: 4
Filing time: 20 Jun 2025, 16:12:40 UTC
Previous filing: 12 Jun 2025
Next filing: 16 Jul 2025
SEC: View on sec.gov

Reporting Owners (1)

Name	Relationship	Address	Signature	Signature date	CIK
SMITH W KEITH	President, Director, 10%+ Owner	C/O DIRECT DIGITAL HOLDINGS, INC., 1177 WEST LOOP SOUT, SUITE 1300, HOUSTON	/s/ Mark Walker, attorney-in-fact for Keith W. Smith	18 Jun 2025	0001203452

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	DRCT	Class A Common Stock, par value $0.001 per share	Conversion of derivative security		+185,000			185,000	18 Jun 2025	By SKW Financial LLC	F1
holding	DRCT	Class A Common Stock, par value $0.001 per share						66,370	18 Jun 2025	Direct

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	DRCT	Class A Common Units of Direct Digital Holdings LLC	Conversion of derivative security	$0	-185,000	-3.44%	$0.000000	5,194,000	18 Jun 2025	Class A Common Stock, par value $0.001 per share	185,000		By Direct Digital Management, LLC	F1

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
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.

Content

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.