DRCT · Direct Digital Holdings, Inc. · Insider Trading

This transaction was executed in multiple trades at prices ranging from $1.95 to $2.165 per share. 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 number of shares sold at each separate price within the range set forth in this footnote.

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.

On January 12, 2026, Direct Digital Holdings, Inc. effected a 55-to-1 reverse stock split and subsequently on April 27, 2026, the Company effected a 4-to-1 reverse stock split (collectively, the "Reverse Stock Splits"). The Class A Common Units held by the Reporting Person had been adjusted as a result of the Reverse Stock Splits.

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.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

On June 12, 2023, the reporting person was granted 111 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 12, 2024, an additional 33 percent vested on June 12, 2025, and the remaining balance of 34 percent of the restricted stock units vested on June 12, 2026. This grant was previously reported as covering 24,615 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

On June 12, 2023, the reporting person was granted 111 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 12, 2024, an additional 33 percent vested on June 12, 2025, and the remaining balance of 34 percent of the restricted stock units vested on June 12, 2026. This grant was previously reported as covering 24,615 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

On January 12, 2026, Direct Digital Holdings, Inc. (the "Company") effected a 55-to-1 reverse stock split (the "January Reverse Stock Split") and subsequently on April 27, 2026, the Company effected a 4-to-1 reverse stock split (the "April Reverse Stock Split," and together with the January Reverse Stock Split, the "Reverse Stock Splits"). The Securities Acquired reported in connection with this transaction have been adjusted to reflect the April Reverse Stock Split and the Amount of Securities Beneficially Owned Following Reported Transaction in connection with this transaction have been adjusted to reflect the Reverse Stock Splits.

This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 11, 2024. This transaction was executed in multiple trades at prices ranging from $2.76 to $2.84 per share. The price reported above reflects the weighted average purchase price on the date indicated rounded to the nearest penny. 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 number of shares.

Represents shares sold solely to satisfy tax liabilities associated with the reported vesting of restricted stock units for 37 shares.

Represents shares sold solely to satisfy tax liabilities associated with the reported vesting of restricted stock units for 37 shares.

Represents shares sold solely to satisfy tax liabilities associated with the reported vesting of restricted stock units for 37 shares.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

On June 12, 2023, the reporting person was granted 111 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 12, 2024, an additional 33 percent vested on June 12, 2025, and the remaining balance of 34 percent of the restricted stock units vested on June 12, 2026. This grant was previously reported as covering 24,615 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

Represents shares sold solely to satisfy tax liabilities associated with the reported vesting of restricted stock units for 159 shares.

Represents shares sold solely to satisfy tax liabilities associated with the reported vesting of restricted stock units for 159 shares.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

On June 9, 2025, the reporting person was granted 159 restricted stock units, vesting on the first anniversary of the grant date conditioned on continued employment as of the vesting date. All of the restricted stock units vested on June 9, 2026. This grant was previously reported as covering 35,000 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

On June 9, 2025, the reporting person was granted 159 restricted stock units, vesting on the first anniversary of the grant date conditioned on continued employment as of the vesting date. All of the restricted stock units vested on June 9, 2026. This grant was previously reported as covering 35,000 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

Represents shares sold solely to satisfy tax liabilities associated with the reported vesting of restricted stock units for 159 shares.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

On June 9, 2025, the reporting person was granted 159 restricted stock units, vesting on the first anniversary of the grant date conditioned on continued employment as of the vesting date. All of the restricted stock units vested on June 9, 2026. This grant was previously reported as covering 35,000 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

On April 1, 2025, the reporting person was granted 203 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 April 1, 2026, an additional 33% of the restricted stock units will vest on April 1, 2027, and the remaining balance of 34% of the restricted stock units will vest on April 1, 2028. 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). This grant was previously reported as covering 45,000 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

On April 1, 2025, the reporting person was granted 101 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 April 1, 2026, an additional 33% of the restricted stock units will vest on April 1, 2027, and the remaining balance of 34% of the restricted stock units will vest on April 1, 2028. 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). This grant was previously reported as covering 22,500 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

On April 1, 2025, the reporting person was granted 101 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 April 1, 2026, an additional 33% of the restricted stock units will vest on April 1, 2027, and the remaining balance of 34% of the restricted stock units will vest on April 1, 2028. 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). This grant was previously reported as covering 22,500 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

On April 1, 2025, the reporting person was granted 101 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 April 1, 2026, an additional 33% of the restricted stock units will vest on April 1, 2027, and the remaining balance of 34% of the restricted stock units will vest on April 1, 2028. 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). This grant was previously reported as covering 22,500 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

On April 1, 2025, the reporting person was granted 203 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 April 1, 2026, an additional 33% of the restricted stock units will vest on April 1, 2027, and the remaining balance of 34% of the restricted stock units will vest on April 1, 2028. 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). This grant was previously reported as covering 45,000 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

This option is scheduled to vest in three equal annual installments beginning on March 24, 2027.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

This option is scheduled to vest in three equal annual installments beginning on March 24, 2027.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

This option is scheduled to vest in three equal annual installments beginning on March 24, 2027.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

This option is scheduled to vest in three equal annual installments beginning on March 24, 2027.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

This option is scheduled to vest in three equal annual installments beginning on March 24, 2027.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

On March 20, 2023, the reporting person was granted 28 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 vested on March 20, 2025, and the remaining balance of 34% of the restricted stock units vested on March 20, 2026. This grant was previously reported as covering 6,315 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

On March 20, 2023, the reporting person was granted 135 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 vested on March 20, 2025, and the remaining balance of 34% of the restricted stock units vested on March 20, 2026. This grant was previously reported as covering 29,910 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Restricted stock units convert into shares of the Company's Class A Common Stock, par value $0.001 per share, on a one-for-one basis.

Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.