Keith W. Smith - Jun 10, 2023 Form 4/A - Amendment Insider Report for Direct Digital Holdings, Inc. (DRCT)

Role: President, Director, 10%+ Owner
Signature: /s/ Keith W. Smith
Stock symbol: DRCT
Transactions as of: Jun 10, 2023
Transactions value $: -$16,068
Form type: 4/A - Amendment
Date filed: 8/23/2023, 09:32 PM
Date Of Original Report: Jun 13, 2023
Previous filing: Mar 22, 2023
Next filing: Dec 7, 2023

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	DRCT	Class A Common Stock	Options Exercise		+20.3K			20.3K	Jun 10, 2023	Direct	F1
transaction	DRCT	Class A Common Stock	Tax liability	-$16.1K	-4.94K	-24.35%	$3.25	15.4K	Jun 10, 2023	Direct	F2
holding	DRCT	Class A Common Stock						40K	Jun 10, 2023	By SKW Financial LLC	F3

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	Restricted Stock Units	Options Exercise	$0	-20.3K	-33.33%	$0.00	40.6K	Jun 10, 2023	Class A Common Stock, par value $0.001 per share	20.3K		Direct	F1, F4

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

Explanation of Responses:

Id	Content
F1	Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.
F2	Due to administrative error, the withholding of shares to satisfy the tax liability incident to the vesting of the restricted stock unit was inadvertently omitted from the original version of this report.
F3	The reporting person, as owner of SKW Financial LLC, may be deemed to have beneficial ownership of the securities directly held by SKW Financial LLC.
F4	On June 10, 2022, the reporting person was granted 60,900 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on June 10, 2023, an additional 33% will vest on June 10, 2024, and the remaining balance of 34% of the restricted stock units will vest on June 10, 2025. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).