DRCT

SEC source: 0001104659-23-094631 · tm2324608-3_4aseq1.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: 20,300

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: 0001104659-23-094629 · tm2324608-1_4aseq1.xml · derivative · entry 3

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 12,434

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.

F3 · derivative.exercise_date: On June 10, 2022, the reporting person was granted 18,650 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 18,650 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: 0001104659-23-094629 · tm2324608-1_4aseq1.xml · nonDerivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 4,394

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.

SEC source: 0001104659-23-094629 · tm2324608-1_4aseq1.xml · nonDerivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,216

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: 0001104659-23-094630 · tm2324608-2_4aseq1.xml · derivative · entry 4

SMITH W KEITH · CIK 0001203452 · Director · President · 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.

F4 · 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).

F4 · 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: 0001104659-23-094630 · tm2324608-2_4aseq1.xml · nonDerivative · entry 2

SMITH W KEITH · CIK 0001203452 · Director · President · 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.

SEC source: 0001104659-23-094630 · tm2324608-2_4aseq1.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 20,300

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: 0001104659-23-035651 · tm2310255-3_4seq1.xml · derivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,315

Underlying: Class A Common Stock, par value $0.001 per share · 6,315 shares

Expires 2033-03-20

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on March 20, 2024.

SEC source: 0001104659-23-035651 · tm2310255-3_4seq1.xml · derivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,315

Underlying: Class A Common Stock, par value $0.001 per share · 6,315 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, beginning on March 20, 2024. 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, beginning on March 20, 2024. 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: 0001104659-23-035653 · tm2310255-5_4seq1.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: 29,910

Underlying: Class A Common Stock, par value $0.001 per share · 29,910 shares

Expires 2033-03-20

F4 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on March 20, 2024.

SEC source: 0001104659-23-035653 · tm2310255-5_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: 29,910

Underlying: Class A Common Stock, par value $0.001 per share · 29,910 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, beginning on March 20, 2024. 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, beginning on March 20, 2024. 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: 0001104659-23-035653 · tm2310255-5_4seq1.xml · derivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 40,000

Underlying: Class A Common Stock, par value $0.001 per share · 40,000 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 100% on March 20, 2024. 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 100% on March 20, 2024. 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: 0001104659-23-035649 · tm2310255-1_4seq1.xml · derivative · entry 2

Echard Susan · CIK 0001796058 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,315

Underlying: Class A Common Stock, par value $0.001 per share · 6,315 shares

Expires 2033-03-20

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on March 20, 2024.

SEC source: 0001104659-23-035649 · tm2310255-1_4seq1.xml · derivative · entry 1

Echard Susan · CIK 0001796058 · Chief Financial Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,315

Underlying: Class A Common Stock, par value $0.001 per share · 6,315 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, beginning on March 20, 2024. 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, beginning on March 20, 2024. 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: 0001104659-23-035652 · tm2310255-4_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: 29,910

Underlying: Class A Common Stock, par value $0.001 per share · 29,910 shares

Expires 2033-03-20

F4 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on March 20, 2024.

SEC source: 0001104659-23-035652 · tm2310255-4_4seq1.xml · derivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 29,910

Underlying: Class A Common Stock, par value $0.001 per share · 29,910 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, beginning on March 20, 2024. 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, beginning on March 20, 2024. 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: 0001104659-23-035652 · tm2310255-4_4seq1.xml · derivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 40,000

Underlying: Class A Common Stock, par value $0.001 per share · 40,000 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 100% on March 20, 2024. 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 100% on March 20, 2024. 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: 0001104659-23-035650 · tm2310255-2_4seq1.xml · derivative · entry 2

Lowrey Maria Vilchez · CIK 0001943064 · Chief Growth Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,315

Underlying: Class A Common Stock, par value $0.001 per share · 6,315 shares

Expires 2033-03-20

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on March 20, 2024.

SEC source: 0001104659-23-035650 · tm2310255-2_4seq1.xml · derivative · entry 1

Lowrey Maria Vilchez · CIK 0001943064 · Chief Growth Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 6,315

Underlying: Class A Common Stock, par value $0.001 per share · 6,315 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, beginning on March 20, 2024. 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, beginning on March 20, 2024. 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: 0001104659-23-004464 · tm233700d2_4seq1.xml · derivative · entry 1

Locke Mistelle · CIK 0001960753 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 21,739

Underlying: Class A Common Stock, par value $0.001 per share · 21,739 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: 0001104659-22-123667 · tm2231764-1_4seq1.xml · derivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 27,259

Underlying: Class A Common Stock · 5,320 shares

Expires 2027-02-15

SEC source: 0001104659-22-122880 · tm2231532-1_4seq1.xml · derivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 21,939

Underlying: Class A Common Stock · 8,688 shares

Expires 2027-02-15

SEC source: 0001104659-22-122118 · tm2231367-2_4seq1.xml · derivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 13,251

Underlying: Class A Common Stock · 13,251 shares

Expires 2027-02-15

SEC source: 0001104659-22-122116 · tm2231367-1_4seq1.xml · derivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 71,124

Underlying: Class A Common Stock · 71,124 shares

Expires 2027-02-15

F1 · price: This transaction was executed in multiple trades at prices ranging from $0.35 to 0.40 per warrant. The price reported above reflects the weighted average purchase price on the date indicated. The reporting person hereby undertakes to provide upon request to the SEC staff, the issuer or a security holder of the issuer full information regarding the purchased warrants.

SEC source: 0001104659-22-096094 · tm2224797d1_4.xml · derivative · entry 3

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

10b5-1 filing: Not disclosed

Ownership: Indirect · By Direct Digital Management, LLC

Disclosed balance after: 5,589,000

Underlying: Class A Common Stock · 100,000 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: 0001104659-22-096094 · tm2224797d1_4.xml · nonDerivative · entry 2

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

10b5-1 filing: Not disclosed

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 40,000

F3 · price: Shares were transferred at fair market value in payment of an obligation owed by the Reporting Person to the transferee.

SEC source: 0001104659-22-096094 · tm2224797d1_4.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Indirect · By Direct Digital Management, LLC

Disclosed balance after: 100,000

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 100,000 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: 0001104659-22-096096 · tm2224797d2_4.xml · derivative · entry 3

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 11,278,000

Underlying: Class A Common Stock · 100,000 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.

F3 · balance_after: Due to an administrative error, the number of derivative securities beneficially owned by the Reporting Person was incorrectly reported as 5,689,000 instead of 11,378,000 on a Form 3 filed on February 17, 2022. This column reflects the corrected balance, as effected by the transactions reported on this Form 4.

SEC source: 0001104659-22-096096 · tm2224797d2_4.xml · nonDerivative · entry 2

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F2 · kind: The Reporting Person distributed 100,000 shares of Class A Common Stock to one of its members for no consideration.

SEC source: 0001104659-22-096096 · tm2224797d2_4.xml · nonDerivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 100,000

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: 0001104659-22-093724 · tm2224283d1_4.xml · derivative · entry 2

Lowrey Maria Vilchez · CIK 0001943064 · Chief Growth Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 11,700

Underlying: Class A Common Stock, par value $0.001 per share · 11,700 shares

Expires 2032-08-22

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on August 22, 2023.

SEC source: 0001104659-22-093724 · tm2224283d1_4.xml · derivative · entry 1

Lowrey Maria Vilchez · CIK 0001943064 · Chief Growth Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 11,700

Underlying: Class A Common Stock, par value $0.001 per share · 11,700 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: 0001104659-22-070579 · tm2218199-2_4seq1.xml · derivative · entry 2

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 60,900

Underlying: Class A Common Stock, par value $0.001 per share · 60,900 shares

Expires 2032-06-10

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on June 10, 2023.

SEC source: 0001104659-22-070579 · tm2218199-2_4seq1.xml · derivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 60,900

Underlying: Class A Common Stock, par value $0.001 per share · 60,900 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: 0001104659-22-070578 · tm2218199-1_4seq1.xml · derivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 13,900

Underlying: Class A Common Stock, par value $0.001 per share · 13,900 shares

Expires 2032-06-10

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on June 10, 2023.

SEC source: 0001104659-22-070578 · tm2218199-1_4seq1.xml · derivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 13,900

Underlying: Class A Common Stock, par value $0.001 per share · 13,900 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: 0001104659-22-070582 · tm2218199-4_4seq1.xml · derivative · entry 2

Echard Susan · CIK 0001796058 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 13,900

Underlying: Class A Common Stock, par value $0.001 per share · 13,900 shares

Expires 2032-06-10

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on June 10, 2023.

SEC source: 0001104659-22-070582 · tm2218199-4_4seq1.xml · derivative · entry 1

Echard Susan · CIK 0001796058 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 13,900

Underlying: Class A Common Stock, par value $0.001 per share · 13,900 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: 0001104659-22-070584 · tm2218199-5_4seq1.xml · derivative · entry 1

Cohen Richard · CIK 0001298692 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 49,382

Underlying: Class A Common Stock, par value $0.001 per share · 49,382 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 service 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 service events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

SEC source: 0001104659-22-070581 · tm2218199-3_4seq1.xml · derivative · entry 2

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 60,900

Underlying: Class A Common Stock, par value $0.001 per share · 60,900 shares

Expires 2032-06-10

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on June 10, 2023.

SEC source: 0001104659-22-070581 · tm2218199-3_4seq1.xml · derivative · entry 1

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 60,900

Underlying: Class A Common Stock, par value $0.001 per share · 60,900 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: 0001104659-22-070585 · tm2218199-6_4seq1.xml · derivative · entry 1

Leatherberry Antoinette Renee · CIK 0001834624 · Director

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 49,382

Underlying: Class A Common Stock, par value $0.001 per share · 49,382 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 service 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 service events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

SEC source: 0001104659-22-073022 · tm2218805-2_4aseq1.xml · derivative · entry 2

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,650

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

Expires 2032-06-10

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on June 10, 2023.

SEC source: 0001104659-22-073022 · tm2218805-2_4aseq1.xml · derivative · entry 1

Pillai Anu · CIK 0001896798 · Chief Technology Officer

10b5-1 filing: Not disclosed

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: 0001104659-22-073004 · tm2218805-1_4aseq1.xml · derivative · entry 2

Echard Susan · CIK 0001796058 · Chief Financial Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 18,650

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

Expires 2032-06-10

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on June 10, 2023.

SEC source: 0001104659-22-073004 · tm2218805-1_4aseq1.xml · derivative · entry 1

Echard Susan · CIK 0001796058 · Chief Financial Officer

10b5-1 filing: Not disclosed

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: 0001918700-22-000010 · primary_doc.xml · nonDerivative · entry 3

Grittani Timothy · CIK 0001918700 · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 0

F3 · price: Represents the weighted average sales price. The shares were sold in multiple transactions at prices ranging from $3.74 to $4.48, inclusive, per share. Full information regarding the number of shares sold at each price shall be provided to the Securities and Exchange Commission Staff (the "Staff"), Issuer or any security holder, upon request.

SEC source: 0001918700-22-000010 · primary_doc.xml · nonDerivative · entry 2

Grittani Timothy · CIK 0001918700 · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 80,000

F2 · price: Represents the weighted average sales price. The shares were sold in multiple transactions at prices ranging from $2.47 to $3.95, inclusive, per share. Full information regarding the number of shares sold at each price shall be provided to the Securities and Exchange Commission Staff (the "Staff"), Issuer or any security holder, upon request.

SEC source: 0001918700-22-000010 · primary_doc.xml · nonDerivative · entry 1

Grittani Timothy · CIK 0001918700 · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 200,000

F1 · price: Represents the weighted average sales price. The shares were sold in multiple transactions at prices ranging from $2.40 to $2.43, inclusive, per share. Full information regarding the number of shares sold at each price shall be provided to the Securities and Exchange Commission Staff (the "Staff"), Issuer or any security holder, upon request.

SEC source: 0001918700-22-000008 · primary_doc.xml · nonDerivative · entry 2

Grittani Timothy · CIK 0001918700 · 10% owner

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 265,000

F2 · price: Represents the weighted average sales price. The shares were sold in multiple transactions at prices ranging from $2.8501 to $2.855, inclusive, per share. Full information regarding the number of shares sold at each price shall be provided to the Securities and Exchange Commission Staff (the "Staff"), Issuer or any security holder, upon request.