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SMITH W KEITH

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34774
SEC CIK
0001203452

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CompanyLast reported asReport datePublished
Direct Digital Holdings, Inc.DRCT · Entity 2630Director · PresidentJanuary 24, 2026June 29, 2026

Disclosed balances

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Latest available filing per company, not a reconstructed current portfolio. Matching sequences show the last reported balance with all source rows expandable; grouping alone does not establish account ownership. Do not add unresolved positions together. Filings may omit unchanged positions, and amendments may correct only part of an older disclosure. Jointly reported shares are not necessarily this owner's personal holdings.

Direct Digital Holdings, Inc.

Report date January 24, 2026 · Filed June 29, 2026

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Class A Common Stock, par value $0.001 per shareSEC Table I · non-derivativeDirect505 Reported balance After 2026-01-24 transaction · row 1 Account or security details depend on footnotes; rows are not merged.
1 source row

Row 1 · 2026-01-24 · Exercise / conversion · Acquired 204 · Balance 505

F1: 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.

F2: 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.

Class A Common Stock, par value $0.001 per shareSEC Table I · non-derivativeDirect444 Reported balance After 2026-01-24 transaction · row 2 Account or security details depend on footnotes; rows are not merged.
1 source row

Row 2 · 2026-01-24 · Tax withholding · Disposed 61 · Balance 444

F3: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F4: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

Class A Common Stock, par value $0.001 per shareSEC Table I · non-derivativeDirect489 Reported balance After 2026-03-20 transaction · row 3 Account or security details depend on footnotes; rows are not merged.
1 source row

Row 3 · 2026-03-20 · Exercise / conversion · Acquired 45 · Balance 489

F3: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F2: 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.

Class A Common Stock, par value $0.001 per shareSEC Table I · non-derivativeDirect475 Reported balance After 2026-03-20 transaction · row 4 Account or security details depend on footnotes; rows are not merged.
1 source row

Row 4 · 2026-03-20 · Tax withholding · Disposed 14 · Balance 475

F3: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F4: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

Class A Common Stock, par value $0.001 per shareSEC Table I · non-derivativeDirect542 Reported balance After 2026-04-01 transaction · row 5 Account or security details depend on footnotes; rows are not merged.
1 source row

Row 5 · 2026-04-01 · Exercise / conversion · Acquired 67 · Balance 542

F3: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F2: 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.

Class A Common Stock, par value $0.001 per shareSEC Table I · non-derivativeDirect522 Reported balance After 2026-04-01 transaction · row 6 Account or security details depend on footnotes; rows are not merged.
1 source row

Row 6 · 2026-04-01 · Exercise / conversion · Disposed 20 · Balance 522

F3: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F4: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

Restricted Stock UnitsSEC Table II · derivative / convertible securityDirect0 Reported balance After 2026-01-24 transaction · row 8 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 8 · 2026-01-24 · Exercise / conversion · Disposed 204 · Balance 0

F2: 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.

F5: On January 24, 2025, the reporting person was granted 204 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 January 24, 2026. This grant was previously reported as covering 45,000 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

Restricted Stock UnitsSEC Table II · derivative / convertible securityDirect0 Reported balance After 2026-03-20 transaction · row 9 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 9 · 2026-03-20 · Exercise / conversion · Disposed 45 · Balance 0

F2: 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.

F6: 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.

Restricted Stock UnitsSEC Table II · derivative / convertible securityDirect136 Reported balance After 2026-04-01 transaction · row 11 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 11 · 2026-04-01 · Exercise / conversion · Disposed 67 · Balance 136

F2: 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.

F8: 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.

Employee Stock Options (right to buy)SEC Table II · derivative / convertible security · Conversion / exercise price $3.32 · Expires 2036-03-24Direct8,750 Reported balance After 2026-03-24 transaction · row 10 Instrument identity requires review; Table II rows are not merged.
1 source row

Row 10 · 2026-03-24 · Grant · Acquired 8,750 · Balance 8,750

F3: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F7: This option is scheduled to vest in three equal annual installments beginning on March 24, 2027.

Class A Common Stock, par value $0.001 per shareSEC Table I · non-derivativeIndirectBy SKW Financial LLC2,114 Reported balance Holding disclosure · report date 2026-01-24 · row 7 Holding and transaction disclosures are not merged.
1 source row

Row 7 · Balance 2,114

F1: 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.

Filing footnotes · ownership attribution and instrument terms

F1: 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.

F2: 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.

F3: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F4: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

F5: On January 24, 2025, the reporting person was granted 204 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 January 24, 2026. This grant was previously reported as covering 45,000 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

F6: 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.

F7: This option is scheduled to vest in three equal annual installments beginning on March 24, 2027.

F8: 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.

Transaction history

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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

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Transaction dateCompanyActivity / securityShares / unitsReported priceReported valueDetails
April 01, 2026 Filed Jun 29, 2026 21:09 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 67 $0.00 $0.00
Disclosure

SEC source: 0001203452-26-000002 · wk-form4_1782767347.xml · derivative · entry 11

SMITH W KEITH · CIK 0001203452 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 136

Underlying: Class A Common Stock, par value $0.001 per share · 67 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.

F2 · derivative.exercise_price: 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.

F8 · shares: 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.

F8 · derivative.exercise_date: 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.

F8 · derivative.expiration_date: 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.

F8 · derivative.underlying_shares: 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.

F8 · balance_after: 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.

Read SEC document
April 01, 2026 Filed Jun 29, 2026 21:09 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock, par value $0.001 per share 20 $3.29 $65.80
Disclosure

SEC source: 0001203452-26-000002 · wk-form4_1782767347.xml · nonDerivative · entry 6

SMITH W KEITH · CIK 0001203452 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 522

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.

F3 · shares: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F4 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

F3 · price: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Read SEC document
April 01, 2026 Filed Jun 29, 2026 21:09 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock, par value $0.001 per share 67 Not disclosed Not disclosed
Disclosure

SEC source: 0001203452-26-000002 · wk-form4_1782767347.xml · nonDerivative · entry 5

SMITH W KEITH · CIK 0001203452 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 542

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.

F3 · shares: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F2 · price: 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.

Read SEC document
March 24, 2026 Filed Jun 29, 2026 21:09 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantEmployee Stock Options (right to buy) · Derivative 8,750 $0.00 Strike: $3.32 $0.00
Disclosure

SEC source: 0001203452-26-000002 · wk-form4_1782767347.xml · derivative · entry 10

SMITH W KEITH · CIK 0001203452 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 8,750

Underlying: Class A Common Stock, par value $0.001 per share · 8,750 shares

Expires 2036-03-24

F3 · derivative.exercise_price: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F3 · shares: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F7 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on March 24, 2027.

F3 · derivative.underlying_shares: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F3 · balance_after: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Read SEC document
March 20, 2026 Filed Jun 29, 2026 21:09 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 45 $0.00 $0.00
Disclosure

SEC source: 0001203452-26-000002 · wk-form4_1782767347.xml · derivative · entry 9

SMITH W KEITH · CIK 0001203452 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class A Common Stock, par value $0.001 per share · 45 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.

F2 · derivative.exercise_price: 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.

F6 · shares: 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.

F6 · derivative.exercise_date: 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.

F6 · derivative.expiration_date: 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.

F6 · derivative.underlying_shares: 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.

Read SEC document
March 20, 2026 Filed Jun 29, 2026 21:09 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock, par value $0.001 per share 14 $3.52 $49.28
Disclosure

SEC source: 0001203452-26-000002 · wk-form4_1782767347.xml · nonDerivative · entry 4

SMITH W KEITH · CIK 0001203452 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 475

F3 · shares: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F4 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

F3 · price: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Read SEC document
March 20, 2026 Filed Jun 29, 2026 21:09 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock, par value $0.001 per share 45 Not disclosed Not disclosed
Disclosure

SEC source: 0001203452-26-000002 · wk-form4_1782767347.xml · nonDerivative · entry 3

SMITH W KEITH · CIK 0001203452 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 489

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.

F3 · shares: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F2 · price: 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.

Read SEC document
January 24, 2026 Filed Jun 29, 2026 21:09 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 204 $0.00 $0.00
Disclosure

SEC source: 0001203452-26-000002 · wk-form4_1782767347.xml · derivative · entry 8

SMITH W KEITH · CIK 0001203452 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Class A Common Stock, par value $0.001 per share · 204 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.

F2 · derivative.exercise_price: 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.

F5 · shares: On January 24, 2025, the reporting person was granted 204 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 January 24, 2026. This grant was previously reported as covering 45,000 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

F5 · derivative.exercise_date: On January 24, 2025, the reporting person was granted 204 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 January 24, 2026. This grant was previously reported as covering 45,000 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

F5 · derivative.expiration_date: On January 24, 2025, the reporting person was granted 204 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 January 24, 2026. This grant was previously reported as covering 45,000 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

F5 · derivative.underlying_shares: On January 24, 2025, the reporting person was granted 204 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 January 24, 2026. This grant was previously reported as covering 45,000 restricted stock units, but was adjusted to reflect the Reverse Stock Splits.

Read SEC document
January 24, 2026 Filed Jun 29, 2026 21:09 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock, par value $0.001 per share 61 $16.48 $1,005.28
Disclosure

SEC source: 0001203452-26-000002 · wk-form4_1782767347.xml · nonDerivative · entry 2

SMITH W KEITH · CIK 0001203452 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 444

F3 · shares: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

F4 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units on the applicable transaction date.

F3 · price: The shares and price reported for the applicable transaction have been adjusted to reflect the April Reverse Stock Split.

Read SEC document
January 24, 2026 Filed Jun 29, 2026 21:09 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock, par value $0.001 per share 204 Not disclosed Not disclosed
Disclosure

SEC source: 0001203452-26-000002 · wk-form4_1782767347.xml · nonDerivative · entry 1

SMITH W KEITH · CIK 0001203452 · Director · President

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 505

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 · shares: 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.

F2 · price: 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.

F1 · balance_after: 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.

Read SEC document
November 14, 2025 Filed Nov 17, 2025 21:04 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 100,000 $0.21 $21,000.00
Disclosure

SEC source: 0001203452-25-000010 · wk-form4_1763413489.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: 457,058

F2 · price: This transaction was executed in multiple trades at prices ranging from $0.20 to $0.23 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.

Read SEC document
November 13, 2025 Filed Nov 17, 2025 21:04 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 71,242 $0.37 $26,359.54
Disclosure

SEC source: 0001203452-25-000010 · wk-form4_1763413489.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: 557,058

F1 · price: This transaction was executed in multiple trades at prices ranging from $0.35 to $0.38 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.

Read SEC document
September 11, 2025 Filed Oct 2, 2025 20:11 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 ConversionClass A Common Units of Direct Digital Holdings LLC · Derivative 600,000 $0.00 $0.00
Disclosure

SEC source: 0001203452-25-000008 · wk-form4_1759435857.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: 4,594,000

Underlying: Class A Common Stock, par value $0.001 per share · 600,000 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.

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September 11, 2025 Filed Oct 2, 2025 20:11 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 ConversionClass A Common Stock, par value $0.001 per share 600,000 Not disclosed Not disclosed
Disclosure

SEC source: 0001203452-25-000008 · wk-form4_1759435857.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: 628,300

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: 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.

Read SEC document
July 28, 2025 Filed Jul 28, 2025 21:04 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 8,050 $0.54 $4,347.00
Disclosure

SEC source: 0001628280-25-036228 · wk-form4_1753736690.xml · nonDerivative · entry 3

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 28,300

F3 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.53 to $0.56 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.

Read SEC document
July 25, 2025 Filed Jul 28, 2025 21:04 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 8,900 $0.53 $4,717.00
Disclosure

SEC source: 0001628280-25-036228 · wk-form4_1753736690.xml · nonDerivative · entry 2

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 36,350

F2 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.52 to $0.56 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.

Read SEC document
July 24, 2025 Filed Jul 28, 2025 21:04 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 15,800 $0.53 $8,374.00
Disclosure

SEC source: 0001628280-25-036228 · wk-form4_1753736690.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 45,250

F1 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.52 to $0.55 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.

Read SEC document
July 23, 2025 Filed Jul 23, 2025 21:47 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 11,934 $0.51 $6,086.34
Disclosure

SEC source: 0001880613-25-000073 · wk-form4_1753307245.xml · nonDerivative · entry 3

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 61,050

F3 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.50 to $0.54 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.

Read SEC document
July 22, 2025 Filed Jul 23, 2025 21:47 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 15,321 $0.51 $7,813.71
Disclosure

SEC source: 0001880613-25-000073 · wk-form4_1753307245.xml · nonDerivative · entry 2

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 72,984

F2 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.50 to $0.54 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.

Read SEC document
July 21, 2025 Filed Jul 23, 2025 21:47 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 16,987 $0.52 $8,833.24
Disclosure

SEC source: 0001880613-25-000073 · wk-form4_1753307245.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 88,305

F1 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.51 to $0.55 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.

Read SEC document
July 18, 2025 Filed Jul 18, 2025 21:05 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 19,488 $0.51 $9,938.88
Disclosure

SEC source: 0001880613-25-000068 · wk-form4_1752872739.xml · nonDerivative · entry 3

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 105,292

F3 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.50 to $0.54 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.

Read SEC document
July 17, 2025 Filed Jul 18, 2025 21:05 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 19,950 $0.52 $10,374.00
Disclosure

SEC source: 0001880613-25-000068 · wk-form4_1752872739.xml · nonDerivative · entry 2

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 124,780

F2 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.51 to $0.53 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.

Read SEC document
July 16, 2025 Filed Jul 18, 2025 21:05 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 11,694 $0.53 $6,197.82
Disclosure

SEC source: 0001880613-25-000068 · wk-form4_1752872739.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 144,730

F1 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.52 to $0.54 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.

Read SEC document
July 15, 2025 Filed Jul 16, 2025 20:05 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 8,100 $0.54 $4,374.00
Disclosure

SEC source: 0001880613-25-000055 · wk-form4_1752696315.xml · nonDerivative · entry 2

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 156,424

F2 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.53 to $0.56 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.

Read SEC document
July 14, 2025 Filed Jul 16, 2025 20:05 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 20,476 $0.55 $11,261.80
Disclosure

SEC source: 0001880613-25-000055 · wk-form4_1752696315.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 164,524

F1 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.53 to $0.59 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.

Read SEC document
June 18, 2025 Filed Jun 20, 2025 20:12 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 ConversionClass A Common Units of Direct Digital Holdings LLC · Derivative 185,000 $0.00 $0.00
Disclosure

SEC source: 0001880613-25-000052 · wk-form4_1750450354.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: 5,194,000

Underlying: Class A Common Stock, par value $0.001 per share · 185,000 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.

Read SEC document
June 18, 2025 Filed Jun 20, 2025 20:12 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 ConversionClass A Common Stock, par value $0.001 per share 185,000 Not disclosed Not disclosed
Disclosure

SEC source: 0001880613-25-000052 · wk-form4_1750450354.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: 185,000

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.

Read SEC document
June 10, 2025 Filed Jun 12, 2025 20:20 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 20,300 $0.00 $0.00
Disclosure

SEC source: 0001880613-25-000026 · wk-form4_1749759614.xml · derivative · entry 3

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 · 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: 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 vested on June 10, 2024, and the remaining balance of 34 percent of the restricted stock units vested on June 10, 2025.

F3 · derivative.expiration_date: 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 vested on June 10, 2024, and the remaining balance of 34 percent of the restricted stock units vested on June 10, 2025.

Read SEC document
June 10, 2025 Filed Jun 12, 2025 20:20 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock, par value $0.001 per share 4,944 $0.56 $2,768.64
Disclosure

SEC source: 0001880613-25-000026 · wk-form4_1749759614.xml · nonDerivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 66,370

F2 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units for 2,300 shares.

Read SEC document
June 10, 2025 Filed Jun 12, 2025 20:20 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock, par value $0.001 per share 20,300 Not disclosed Not disclosed
Disclosure

SEC source: 0001880613-25-000026 · wk-form4_1749759614.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 71,314

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.

Read SEC document
April 01, 2025 Filed Apr 4, 2025 21:49 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantEmployee Stock Options (right to buy) · Derivative 45,000 $0.00 Strike: $0.64 $0.00
Disclosure

SEC source: 0001628280-25-016872 · wk-form4_1743803339.xml · derivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 45,000

Underlying: Class A Common Stock, par value $0.001 per share · 45,000 shares

Expires 2035-04-01

F3 · derivative.exercise_date: This option is scheduled to vest in three equal annual installments beginning on April 1, 2026.

Read SEC document
April 01, 2025 Filed Apr 4, 2025 21:49 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantRestricted Stock Units · Derivative 45,000 $0.00 $0.00
Disclosure

SEC source: 0001628280-25-016872 · wk-form4_1743803339.xml · derivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 45,000

Underlying: Class A Common Stock, par value $0.001 per share · 45,000 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 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).

Read SEC document
March 27, 2025 Filed Mar 27, 2025 23:55 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 12,186 $0.78 $9,505.08
Disclosure

SEC source: 0001628280-25-015294 · wk-form4_1743119721.xml · nonDerivative · entry 5

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 0

F5 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.70 to $0.87 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.

Read SEC document
March 26, 2025 Filed Mar 27, 2025 23:55 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 20,563 $0.78 $16,039.14
Disclosure

SEC source: 0001628280-25-015294 · wk-form4_1743119721.xml · nonDerivative · entry 4

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 12,186

F4 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.75 to $0.82 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.

Read SEC document
March 25, 2025 Filed Mar 27, 2025 23:55 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 7,700 $0.76 $5,852.00
Disclosure

SEC source: 0001628280-25-015294 · wk-form4_1743119721.xml · nonDerivative · entry 3

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 32,749

F3 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.75 to $0.77 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.

Read SEC document
March 24, 2025 Filed Mar 24, 2025 22:49 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 10,300 $0.76 $7,828.00
Disclosure

SEC source: 0001628280-25-014575 · wk-form4_1742856573.xml · nonDerivative · entry 3

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 40,449

F3 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.74 to $0.81 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.

Read SEC document
March 21, 2025 Filed Mar 24, 2025 22:49 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 5,831 $0.76 $4,431.56
Disclosure

SEC source: 0001628280-25-014575 · wk-form4_1742856573.xml · nonDerivative · entry 2

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 50,749

F2 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.74 to $0.78 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.

Read SEC document
March 20, 2025 Filed Mar 24, 2025 22:49 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 15,631 $0.79 $12,348.49
Disclosure

SEC source: 0001628280-25-014575 · wk-form4_1742856573.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 56,580

F1 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.74 to $0.85 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.

Read SEC document
March 20, 2025 Filed Mar 27, 2025 23:55 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 9,970 $0.00 $0.00
Disclosure

SEC source: 0001628280-25-015294 · wk-form4_1743119721.xml · derivative · entry 7

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 9,970

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 vested 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 vested 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).

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March 20, 2025 Filed Mar 27, 2025 23:55 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock, par value $0.001 per share 2,957 $0.79 $2,336.03
Disclosure

SEC source: 0001628280-25-015294 · wk-form4_1743119721.xml · nonDerivative · entry 2

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 51,014

F2 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units for 9,970 shares.

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March 20, 2025 Filed Mar 27, 2025 23:55 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock, par value $0.001 per share 9,970 Not disclosed Not disclosed
Disclosure

SEC source: 0001628280-25-015294 · wk-form4_1743119721.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 53,971

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.

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March 19, 2025 Filed Mar 19, 2025 22:42 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 10,171 $0.80 $8,136.80
Disclosure

SEC source: 0001628280-25-013907 · wk-form4_1742424151.xml · nonDerivative · entry 3

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 72,211

F3 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.76 to $0.83 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.

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March 18, 2025 Filed Mar 19, 2025 22:42 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 5,125 $0.80 $4,100.00
Disclosure

SEC source: 0001628280-25-013907 · wk-form4_1742424151.xml · nonDerivative · entry 2

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 82,382

F2 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.80 to $0.83 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.

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March 17, 2025 Filed Mar 19, 2025 22:42 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 8,657 $0.73 $6,319.61
Disclosure

SEC source: 0001628280-25-013907 · wk-form4_1742424151.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 87,507

F1 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.65 to $0.79 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.

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March 14, 2025 Filed Mar 17, 2025 11:37 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 15,874 $0.77 $12,222.98
Disclosure

SEC source: 0001628280-25-012905 · wk-form4_1742211438.xml · nonDerivative · entry 3

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 96,164

F3 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.75 to $0.83 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.

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March 13, 2025 Filed Mar 17, 2025 11:37 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 3,803 $0.81 $3,080.43
Disclosure

SEC source: 0001628280-25-012905 · wk-form4_1742211438.xml · nonDerivative · entry 2

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 112,038

F2 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.79 to $0.84 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.

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March 12, 2025 Filed Mar 17, 2025 11:37 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock, par value $0.001 per share 14,881 $0.83 $12,351.23
Disclosure

SEC source: 0001628280-25-012905 · wk-form4_1742211438.xml · nonDerivative · entry 1

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

10b5-1 filing: Plan reported

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 115,841

F1 · price: This sale was made pursuant to a 10b5-1 plan previously entered into by the reporting person on December 12, 2024. This transaction was executed in multiple trades at prices ranging from $0.79 to $0.94 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.

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January 24, 2025 Filed Jan 28, 2025 21:37 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantEmployee Stock Options (right to buy) · Derivative 45,000 $0.00 Strike: $1.38 $0.00
Disclosure

SEC source: 0001628280-25-002812 · wk-form4_1738100235.xml · derivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 45,000

Underlying: Class A Common Stock, par value $0.001 per share · 45,000 shares

Expires 2035-01-24

F3 · derivative.exercise_date: This option will vest one year from the date of grant conditioned on continued employment as of the vesting date.

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January 24, 2025 Filed Jan 28, 2025 21:37 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantRestricted Stock Units · Derivative 45,000 $0.00 $0.00
Disclosure

SEC source: 0001628280-25-002812 · wk-form4_1738100235.xml · derivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 45,000

Underlying: Class A Common Stock, par value $0.001 per share · 45,000 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: Grant of restricted stock units under the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan. The restricted stock units will vest one year from the date of grant conditioned on continued employment as of the vesting date.

F2 · derivative.expiration_date: Grant of restricted stock units under the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan. The restricted stock units will vest one year from the date of grant conditioned on continued employment as of the vesting date.

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December 13, 2024 Filed Jan 15, 2025 21:02 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Disposition to issuerRestricted Stock Units · Derivative 9,970 $0.00 $0.00
Disclosure

SEC source: 0001628280-25-001598 · wk-form4_1736974961.xml · derivative · entry 5

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 · 9,970 shares

Expires not disclosed

F1 · derivative.exercise_price: On December 13, 2024, the issuer and the reporting person entered into a rescission agreement to effect the reporting person's voluntary request to rescind all restricted stock units and underlying shares of Class A Common Stock issued to the reporting person in 2024, as reported in the issuer's Form 8-K filed on December 18, 2024.

F1 · kind: On December 13, 2024, the issuer and the reporting person entered into a rescission agreement to effect the reporting person's voluntary request to rescind all restricted stock units and underlying shares of Class A Common Stock issued to the reporting person in 2024, as reported in the issuer's Form 8-K filed on December 18, 2024.

F1 · derivative.exercise_date: On December 13, 2024, the issuer and the reporting person entered into a rescission agreement to effect the reporting person's voluntary request to rescind all restricted stock units and underlying shares of Class A Common Stock issued to the reporting person in 2024, as reported in the issuer's Form 8-K filed on December 18, 2024.

F1 · derivative.expiration_date: On December 13, 2024, the issuer and the reporting person entered into a rescission agreement to effect the reporting person's voluntary request to rescind all restricted stock units and underlying shares of Class A Common Stock issued to the reporting person in 2024, as reported in the issuer's Form 8-K filed on December 18, 2024.

F1 · balance_after: On December 13, 2024, the issuer and the reporting person entered into a rescission agreement to effect the reporting person's voluntary request to rescind all restricted stock units and underlying shares of Class A Common Stock issued to the reporting person in 2024, as reported in the issuer's Form 8-K filed on December 18, 2024.

F1 · ownership.direct: On December 13, 2024, the issuer and the reporting person entered into a rescission agreement to effect the reporting person's voluntary request to rescind all restricted stock units and underlying shares of Class A Common Stock issued to the reporting person in 2024, as reported in the issuer's Form 8-K filed on December 18, 2024.

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Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.