DRCT

SEC source: 0001104659-24-093459 · tm2422704-5_4seq1.xml · nonDerivative · entry 2

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 81,973

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: 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.

SEC source: 0001104659-24-093459 · tm2422704-5_4seq1.xml · nonDerivative · entry 1

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 72,003

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: 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 · balance_after: Due to administrative error, the number of non-derivative securities beneficially owned by the Reporting Person was incorrectly reported as 32,058 instead of 32,003 on a Form 4 filed on March 20, 2024. This column reflects the corrected balance, as effected by the transactions reported on this Form 4.

SEC source: 0001104659-24-093457 · tm2422704-4_4seq1.xml · derivative · entry 7

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 19,940

Underlying: Class A Common Stock, par value $0.001 per share · 9,970 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: 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.

F6 · derivative.exercise_date: On March 20, 2023, the reporting person was granted 29,910 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 March 20, 2024, an additional 33% of the restricted stock units will vest on March 20, 2025, and the remaining balance of 34% of the restricted stock units will vest on March 20, 2026. 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).

F6 · derivative.expiration_date: On March 20, 2023, the reporting person was granted 29,910 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 March 20, 2024, an additional 33% of the restricted stock units will vest on March 20, 2025, and the remaining balance of 34% of the restricted stock units will vest on March 20, 2026. 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).

SEC source: 0001104659-24-093457 · tm2422704-4_4seq1.xml · derivative · entry 6

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class A Common Stock, par value $0.001 per share · 40,000 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: 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.

F5 · derivative.exercise_date: On March 20, 2023, the reporting person was granted 40,000 restricted stock units. 100% of the restricted stock units vested on March 20, 2024.

F5 · derivative.expiration_date: On March 20, 2023, the reporting person was granted 40,000 restricted stock units. 100% of the restricted stock units vested on March 20, 2024.

SEC source: 0001104659-24-093457 · tm2422704-4_4seq1.xml · nonDerivative · entry 2

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 81,973

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: 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.

SEC source: 0001104659-24-093457 · tm2422704-4_4seq1.xml · nonDerivative · entry 1

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 72,003

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: 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 · balance_after: Due to administrative error, the number of non-derivative securities beneficially owned by the Reporting Person was incorrectly reported as 32,058 instead of 32,003 on a Form 4 filed on March 20, 2024. This column reflects the corrected balance, as effected by the transactions reported on this Form 4.

SEC source: 0001104659-24-093451 · tm2422704-2_4seq1.xml · derivative · entry 3

Lowrey Maria Vilchez · CIK 0001943064 · Chief Growth Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class A Common Stock, par value $0.001 per share · 4,210 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: 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.

F4 · derivative.exercise_date: On March 20, 2023, the reporting person was granted 6,315 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 March 20, 2024, an additional 33% of the restricted stock units will vest on March 20, 2025, and the remaining balance of 34% of the restricted stock units will vest on March 20, 2026. 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).

F4 · derivative.expiration_date: On March 20, 2023, the reporting person was granted 6,315 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 March 20, 2024, an additional 33% of the restricted stock units will vest on March 20, 2025, and the remaining balance of 34% of the restricted stock units will vest on March 20, 2026. 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).

SEC source: 0001104659-24-093451 · tm2422704-2_4seq1.xml · nonDerivative · entry 1

Lowrey Maria Vilchez · CIK 0001943064 · Chief Growth Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 12,103

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: 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 · balance_after: Due to administrative error, the number of non-derivative securities beneficially owned by the Reporting Person was incorrectly reported as 10,053 instead of 9,998 on a Form 4 filed on March 20, 2024. This column reflects the corrected balance, as effected by the transactions reported on this Form 4.

SEC source: 0001104659-24-036805 · tm249373-4_4seq1.xml · nonDerivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,435

SEC source: 0001104659-24-036802 · tm249373-2_4seq1.xml · nonDerivative · entry 1

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 32,058

SEC source: 0001104659-24-036800 · tm249373-1_4seq1.xml · nonDerivative · entry 1

Diaz Diana P · CIK 0001493839 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,694

SEC source: 0001104659-24-036807 · tm249373-5_4seq1.xml · nonDerivative · entry 1

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 32,058

SEC source: 0001104659-24-036803 · tm249373-3_4seq1.xml · nonDerivative · entry 1

Lowrey Maria Vilchez · CIK 0001943064 · Chief Growth Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,053

SEC source: 0001104659-24-033994 · tm248688-1_4seq1.xml · nonDerivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 13,396

F1 · kind: Represents an award of fully vested shares of the Class A Common Stock, par value $0.001 per share ("Class A Common Stock") of Direct Digital Holdings, Inc. (the "Issuer") granted to the Reporting Person in lieu of annual incentive cash awards earned by the Reporting Person for the fiscal year ended December 31, 2023 under the Issuer's 2022 Omnibus Incentive Plan.

SEC source: 0001104659-24-033997 · tm248688-3_4seq1.xml · nonDerivative · entry 1

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 37,861

F1 · kind: Represents an award of fully vested shares of the Class A Common Stock, par value $0.001 per share ("Class A Common Stock") of Direct Digital Holdings, Inc. (the "Issuer") granted to the Reporting Person in lieu of annual incentive cash awards earned by the Reporting Person for the fiscal year ended December 31, 2023 under the Issuer's 2022 Omnibus Incentive Plan.

SEC source: 0001104659-24-034000 · tm248688-5_4seq1.xml · nonDerivative · entry 1

Diaz Diana P · CIK 0001493839 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,251

F1 · kind: Represents an award of fully vested shares of the Class A Common Stock, par value $0.001 per share ("Class A Common Stock") of Direct Digital Holdings, Inc. (the "Issuer") granted to the Reporting Person in lieu of annual incentive cash awards earned by the Reporting Person for the fiscal year ended December 31, 2023 under the Issuer's 2022 Omnibus Incentive Plan.

SEC source: 0001104659-24-033996 · tm248688-2_4seq1.xml · nonDerivative · entry 1

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 37,861

F1 · kind: Represents an award of fully vested shares of the Class A Common Stock, par value $0.001 per share ("Class A Common Stock") of Direct Digital Holdings, Inc. (the "Issuer") granted to the Reporting Person in lieu of annual incentive cash awards earned by the Reporting Person for the fiscal year ended December 31, 2023 under the Issuer's 2022 Omnibus Incentive Plan.

SEC source: 0001104659-24-033999 · tm248688-4_4seq1.xml · nonDerivative · entry 1

Lowrey Maria Vilchez · CIK 0001943064 · Chief Growth Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 12,833

F1 · kind: Represents an award of fully vested shares of the Class A Common Stock, par value $0.001 per share ("Class A Common Stock") of Direct Digital Holdings, Inc. (the "Issuer") granted to the Reporting Person in lieu of annual incentive cash awards earned by the Reporting Person for the fiscal year ended December 31, 2023 under the Issuer's 2022 Omnibus Incentive Plan.

SEC source: 0001104659-24-007864 · tm244384-1_4seq1.xml · nonDerivative · entry 1

Locke Mistelle · CIK 0001960753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 5,527

F1 · kind: Represents shares sold to cover withholding tax obligations on the settlement of the previously reported vesting of the Reporting Person's restricted share units.

SEC source: 0001104659-24-005325 · tm243720-1_4seq1.xml · derivative · entry 2

Locke Mistelle · CIK 0001960753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 14,493

Underlying: Class A Common Stock, par value $0.001 per share · 7,246 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: 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 · derivative.exercise_date: On January 16, 2023, the reporting person was granted 21,739 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on January 16, 2024, an additional 33 percent will vest on January 16, 2025, and the remaining balance of 34 percent of the restricted stock units will vest on January 16, 2026. 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).

F2 · derivative.expiration_date: On January 16, 2023, the reporting person was granted 21,739 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on January 16, 2024, an additional 33 percent will vest on January 16, 2025, and the remaining balance of 34 percent of the restricted stock units will vest on January 16, 2026. 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).

SEC source: 0001104659-24-005325 · tm243720-1_4seq1.xml · nonDerivative · entry 1

Locke Mistelle · CIK 0001960753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,246

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: 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.

SEC source: 0001104659-23-125823 · tm2332846-1_4seq1.xml · nonDerivative · entry 2

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 130,722

F2 · price: Reflects the weighted average purchase price of multiple same-way open market sale transactions effected by the Reporting Person on the same day at different prices through a purchase order executed by a broker-dealer. The Reporting Person reported on a single line all such transactions that occurred within a one-dollar price range. The range of prices for the sale transactions on December 12, 2023 was $10.00 to $10.54. The Reporting Person hereby undertakes to provide upon request by the Securities Exchange Commission staff, the issuer, or a stockholder of the issuer, full information regarding the number of shares sold at each separate price.

F3 · ownership.nature: The Reporting Person, as owner of SKW Financial LLC and a Managing Partner of Direct Digital Management, LLC, may be deemed to have beneficial ownership of the securities directly held by SKW Financial LLC and Direct Digital Management, LLC. On December 11, 2023, on behalf of the reporting person, SKW Financial LLC sold 77,930 shares of Class A Common Stock at a weighted average price of $11.1314. On December 12, 2023, on behalf of the reporting person, SKW Financial LLC sold 130,722 shares of Class A Common Stock at a weighted average price of $10.22.

SEC source: 0001104659-23-125823 · tm2332846-1_4seq1.xml · nonDerivative · entry 1

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 172,070

F1 · price: Reflects the weighted average purchase price of multiple same-way open market sale transactions effected by the Reporting Person on the same day at different prices through a purchase order executed by a broker-dealer. The Reporting Person reported on a single line all such transactions that occurred within a one-dollar price range. The range of prices for the sale transactions on December 11, 2023 was $10.83 to $11.55. The Reporting Person hereby undertakes to provide upon request by the Securities Exchange Commission staff, the issuer, or a stockholder of the issuer, full information regarding the number of shares sold at each separate price.

F3 · ownership.nature: The Reporting Person, as owner of SKW Financial LLC and a Managing Partner of Direct Digital Management, LLC, may be deemed to have beneficial ownership of the securities directly held by SKW Financial LLC and Direct Digital Management, LLC. On December 11, 2023, on behalf of the reporting person, SKW Financial LLC sold 77,930 shares of Class A Common Stock at a weighted average price of $11.1314. On December 12, 2023, on behalf of the reporting person, SKW Financial LLC sold 130,722 shares of Class A Common Stock at a weighted average price of $10.22.

SEC source: 0001104659-23-124376 · tm2332455-1_4seq1.xml · derivative · entry 3

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: No plan indicated

Ownership: Indirect · By Direct Digital Management, LLC

Disclosed balance after: 5,489,000

Underlying: Class A Common Stock, par value $0.001 per share · 200,000 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: 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.

F1 · derivative.exercise_date: 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.

F1 · derivative.expiration_date: 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.

SEC source: 0001104659-23-124376 · tm2332455-1_4seq1.xml · nonDerivative · entry 1

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: No plan indicated

Ownership: Indirect · By AJN Energy & Transport Ventures, LLC

Disclosed balance after: 200,000

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: 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.

F2 · ownership.nature: Upon receipt of the securities converted from Table II, Direct Digital Management, LLC distributed 200,000 shares of Class A Common Stock to one of its members, AJN Energy & Transport Ventures, LLC, for no consideration. The Reporting Person, as owner of AJN Energy & Transport Ventures, LLC and a Managing Partner of Direct Digital Management, LLC, may be deemed to have beneficial ownership of the securities directly held by AJN Energy & Transport Ventures, LLC and Direct Digital Management, LLC.

SEC source: 0001104659-23-124377 · tm2332455-2_4seq1.xml · derivative · entry 3

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Indirect · By Direct Digital Management, LLC

Disclosed balance after: 5,379,000

Underlying: Class A Common Stock, par value $0.001 per share · 210,000 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: 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.

F1 · derivative.exercise_date: 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.

F1 · derivative.expiration_date: 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.

SEC source: 0001104659-23-124377 · tm2332455-2_4seq1.xml · nonDerivative · entry 1

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 250,000

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: 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.

F2 · ownership.nature: Upon receipt of the securities converted from Table II, Direct Digital Management, LLC distributed 210,000 shares of Class A Common Stock to one of its members, SKW Financial LLC, for no consideration. The Reporting Person, as owner of SKW Financial LLC and a Managing Partner of Direct Digital Management, LLC, may be deemed to have beneficial ownership of the securities directly held by SKW Financial LLC and Direct Digital Management, LLC.

SEC source: 0001104659-23-124378 · tm2332455-3_4seq1.xml · derivative · entry 3

Direct Digital Management, LLC · CIK 0001897454 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 10,868,000

Underlying: Class A Common Stock · 410,000 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: 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 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.

F1 · derivative.exercise_date: 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 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.

F1 · derivative.expiration_date: 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 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.

SEC source: 0001104659-23-124378 · tm2332455-3_4seq1.xml · nonDerivative · entry 2

Direct Digital Management, LLC · CIK 0001897454 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

F2 · kind: The Reporting Person distributed 410,000 shares of Class A Common Stock to two of its members for no consideration.

SEC source: 0001104659-23-124378 · tm2332455-3_4seq1.xml · nonDerivative · entry 1

Direct Digital Management, LLC · CIK 0001897454 · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 410,000

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: 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 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.

SEC source: 0001104659-23-109872 · tm2328560d1_4.xml · derivative · entry 2

Diaz Diana P · CIK 0001493839 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 18,650

Underlying: Class A Common Stock, par value $0.001 per share · 18,650 shares

Expires 2033-10-16

F3 · derivative.exercise_date: This option is scheduled to vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date beginning on October 16, 2024.

SEC source: 0001104659-23-109872 · tm2328560d1_4.xml · derivative · entry 1

Diaz Diana P · CIK 0001493839 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 18,650

Underlying: Class A Common Stock, par value $0.001 per share · 18,650 shares

Expires not disclosed

F1 · derivative.exercise_price: 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 · derivative.exercise_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. 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).

F2 · derivative.expiration_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. 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).

SEC source: 0001104659-23-094632 · tm2324608-4_4seq1.xml · derivative · entry 3

Lowrey Maria Vilchez · CIK 0001943064 · Chief Growth Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,800

Underlying: Class A Common Stock, par value $0.001 per share · 3,900 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: 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 · derivative.exercise_date: On August 22, 2023, the reporting person was granted 11,700 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 August 22, 2023, an additional 33% will vest on August 22, 2024, and the remaining balance of 34% of the restricted stock units will vest on August 22, 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).

F2 · derivative.expiration_date: On August 22, 2023, the reporting person was granted 11,700 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 August 22, 2023, an additional 33% will vest on August 22, 2024, and the remaining balance of 34% of the restricted stock units will vest on August 22, 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).

SEC source: 0001104659-23-094632 · tm2324608-4_4seq1.xml · nonDerivative · entry 2

Lowrey Maria Vilchez · CIK 0001943064 · Chief Growth Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,743

SEC source: 0001104659-23-094632 · tm2324608-4_4seq1.xml · nonDerivative · entry 1

Lowrey Maria Vilchez · CIK 0001943064 · Chief Growth Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,900

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: 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.

SEC source: 0001104659-23-070909 · tm2318595-3_4seq1.xml · derivative · entry 3

Cohen Richard · CIK 0001298692 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,615

Underlying: Class A Common Stock, par value $0.001 per share · 24,615 shares

Expires not disclosed

F1 · derivative.exercise_price: 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.

F3 · derivative.exercise_date: The restricted stock units will vest in three equal annual installments on each of the first, second and third anniversaries of the grant date. 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).

F3 · derivative.expiration_date: The restricted stock units will vest in three equal annual installments on each of the first, second and third anniversaries of the grant date. 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).

SEC source: 0001104659-23-070908 · tm2318595-2_4seq1.xml · derivative · entry 3

Leatherberry Antoinette Renee · CIK 0001834624 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,615

Underlying: Class A Common Stock, par value $0.001 per share · 24,615 shares

Expires not disclosed

F1 · derivative.exercise_price: 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.

F3 · derivative.exercise_date: The restricted stock units will vest in three equal annual installments on each of the first, second and third anniversaries of the grant date. 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).

F3 · derivative.expiration_date: The restricted stock units will vest in three equal annual installments on each of the first, second and third anniversaries of the grant date. 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).

SEC source: 0001104659-23-070913 · tm2318595-6_4seq1.xml · derivative · entry 1

Locke Mistelle · CIK 0001960753 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 24,615

Underlying: Class A Common Stock, par value $0.001 per share · 24,615 shares

Expires not disclosed

F1 · derivative.exercise_price: 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 · derivative.exercise_date: The restricted stock units will vest in three equal annual installments on each of the first, second and third anniversaries of the grant date. 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).

F2 · derivative.expiration_date: The restricted stock units will vest in three equal annual installments on each of the first, second and third anniversaries of the grant date. 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).

SEC source: 0001104659-23-070910 · tm2318595-4_4seq1.xml · derivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 9,313

Underlying: Class A Common Stock, par value $0.001 per share · 4,587 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: 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 · derivative.exercise_date: On June 10, 2022, the reporting person was granted 13,900 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent will vest on June 10, 2024, and the remaining balance of 34 percent 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).

F2 · derivative.expiration_date: On June 10, 2022, the reporting person was granted 13,900 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent will vest on June 10, 2024, and the remaining balance of 34 percent 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).

SEC source: 0001104659-23-070910 · tm2318595-4_4seq1.xml · nonDerivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,587

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: 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.

SEC source: 0001104659-23-070911 · tm2318595-5_4seq1.xml · derivative · entry 2

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 40,803

Underlying: Class A Common Stock, par value $0.001 per share · 20,097 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: 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 · derivative.exercise_date: 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 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent will vest on June 10, 2024, and the remaining balance of 34 percent 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).

F2 · derivative.expiration_date: 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 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent will vest on June 10, 2024, and the remaining balance of 34 percent 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).

SEC source: 0001104659-23-070911 · tm2318595-5_4seq1.xml · nonDerivative · entry 1

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 20,097

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: 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.

SEC source: 0001104659-23-070909 · tm2318595-3_4seq1.xml · derivative · entry 2

Cohen Richard · CIK 0001298692 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 33,086

Underlying: Class A Common Stock, par value $0.001 per share · 16,296 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: 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 · derivative.exercise_date: On June 10, 2022, the reporting person was granted 49,382 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent will vest on June 10, 2024, and the remaining balance of 34 percent 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).

F2 · derivative.expiration_date: On June 10, 2022, the reporting person was granted 49,382 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent will vest on June 10, 2024, and the remaining balance of 34 percent 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).

SEC source: 0001104659-23-070909 · tm2318595-3_4seq1.xml · nonDerivative · entry 1

Cohen Richard · CIK 0001298692 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,296

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: 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.

SEC source: 0001104659-23-070907 · tm2318595-1_4seq1.xml · derivative · entry 3

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 40,803

Underlying: Class A Common Stock, par value $0.001 per share · 20,097 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: 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.

F3 · derivative.exercise_date: 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 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent will vest on June 10, 2024, and the remaining balance of 34 percent 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).

F3 · derivative.expiration_date: 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 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent will vest on June 10, 2024, and the remaining balance of 34 percent 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).

SEC source: 0001104659-23-070907 · tm2318595-1_4seq1.xml · nonDerivative · entry 1

SMITH W KEITH · CIK 0001203452 · Director · President · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 20,097

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: 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.

SEC source: 0001104659-23-070908 · tm2318595-2_4seq1.xml · derivative · entry 2

Leatherberry Antoinette Renee · CIK 0001834624 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 33,086

Underlying: Class A Common Stock, par value $0.001 per share · 16,296 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: 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 · derivative.exercise_date: On June 10, 2022, the reporting person was granted 49,382 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent will vest on June 10, 2024, and the remaining balance of 34 percent 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).

F2 · derivative.expiration_date: On June 10, 2022, the reporting person was granted 49,382 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent will vest on June 10, 2024, and the remaining balance of 34 percent 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).

SEC source: 0001104659-23-070908 · tm2318595-2_4seq1.xml · nonDerivative · entry 1

Leatherberry Antoinette Renee · CIK 0001834624 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 16,296

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: 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.

SEC source: 0001104659-23-094631 · tm2324608-3_4aseq1.xml · derivative · entry 3

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 40,600

Underlying: Class A Common Stock, par value $0.001 per share · 20,300 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · derivative.exercise_price: 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.

F3 · derivative.exercise_date: 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).

F3 · derivative.expiration_date: 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).

SEC source: 0001104659-23-094631 · tm2324608-3_4aseq1.xml · nonDerivative · entry 2

Walker Mark D · CIK 0001896664 · Director · Chairman and CEO · 10% owner

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 15,356

F2 · shares: 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.