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SMITH W KEITH

Disclosed activity across 1 company

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34774
SEC CIK
0001203452

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Reported relationships

Latest disclosed role at each company.

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

Disclosed balances

About these balances

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.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction dateCompanyActivity / securityShares / unitsReported priceReported valueDetails
December 13, 2024 Filed Jan 15, 2025 21:02 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Disposition to issuerRestricted Stock Units · Derivative 40,000 $0.00 $0.00
Disclosure

SEC source: 0001628280-25-001598 · wk-form4_1736974961.xml · derivative · entry 4

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

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

Expires not disclosed

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.

Read SEC document
December 13, 2024 Filed Jan 15, 2025 21:02 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Disposition to issuerClass A Common Stock, par value $0.001 per share 7,542 Not disclosed Not disclosed
Disclosure

SEC source: 0001628280-25-001598 · wk-form4_1736974961.xml · nonDerivative · entry 2

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 44,001

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 · 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.

Read SEC document
December 13, 2024 Filed Jan 15, 2025 21:02 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Disposition to issuerClass A Common Stock, par value $0.001 per share 25,435 Not disclosed Not disclosed
Disclosure

SEC source: 0001628280-25-001598 · wk-form4_1736974961.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 51,543

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 · 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.

Read SEC document
November 15, 2024 Filed Nov 19, 2024 21:23 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock 313 $1.80 $563.40
Disclosure

SEC source: 0001628280-24-048454 · wk-form4_1732051376.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 76,978

F1 · price: This transaction was executed in multiple trades at prices ranging from $1.80 to $1.81 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
June 14, 2024 Filed Jun 15, 2024 01:24 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock 7,989 $2.64 $21,090.96
Disclosure

SEC source: 0001104659-24-071906 · tm2417375-6_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 44,369

F1 · shares: Represents shares withheld to satisfy tax liabilities associated with the previously reported vesting of restricted stock units for 20,300 shares on June 10, 2024.

Read SEC document
June 10, 2024 Filed Jun 12, 2024 23:56 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 20,300 $0.00 $0.00
Disclosure

SEC source: 0001104659-24-070956 · tm2417141-5_4seq1.xml · derivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 20,300

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.

F2 · 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 will vest on June 10, 2025. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

F2 · derivative.expiration_date: 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 will vest on June 10, 2025. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

Read SEC document
June 10, 2024 Filed Jun 12, 2024 23:56 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock 20,300 Not disclosed Not disclosed
Disclosure

SEC source: 0001104659-24-070956 · tm2417141-5_4seq1.xml · nonDerivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 52,358

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, 2024 Filed Aug 27, 2024 20:32 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock 2,428 $15.24 $37,002.72
Disclosure

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

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 64,980

F4 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units for 9,970 shares.

Read SEC document
April 01, 2024 Filed Aug 27, 2024 20:32 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock 14,565 $15.24 $221,970.60
Disclosure

SEC source: 0001104659-24-093457 · tm2422704-4_4seq1.xml · nonDerivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 67,408

F3 · shares: Represents shares withheld to satisfy tax liabilities associated with the reported vesting of restricted stock units for 40,000 shares.

Read SEC document
March 20, 2024 Filed Aug 27, 2024 20:32 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 9,970 $0.00 $0.00
Disclosure

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

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 19,940

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

Expires not disclosed

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

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F6 · derivative.exercise_date: On March 20, 2023, the reporting person was granted 29,910 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on March 20, 2024, an additional 33% of the restricted stock units will vest on March 20, 2025, and the remaining balance of 34% of the restricted stock units will vest on March 20, 2026. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

F6 · derivative.expiration_date: On March 20, 2023, the reporting person was granted 29,910 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on March 20, 2024, an additional 33% of the restricted stock units will vest on March 20, 2025, and the remaining balance of 34% of the restricted stock units will vest on March 20, 2026. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

Read SEC document
March 20, 2024 Filed Aug 27, 2024 20:32 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 40,000 $0.00 $0.00
Disclosure

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

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

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

Expires not disclosed

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

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

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

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

Read SEC document
March 20, 2024 Filed Aug 27, 2024 20:32 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock 9,970 Not disclosed Not disclosed
Disclosure

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

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 81,973

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

F1 · price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

Read SEC document
March 20, 2024 Filed Aug 27, 2024 20:32 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock 40,000 Not disclosed Not disclosed
Disclosure

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

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 72,003

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

F1 · price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · balance_after: Due to administrative error, the number of non-derivative securities beneficially owned by the Reporting Person was incorrectly reported as 32,058 instead of 32,003 on a Form 4 filed on March 20, 2024. This column reflects the corrected balance, as effected by the transactions reported on this Form 4.

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March 18, 2024 Filed Mar 20, 2024 21:58 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock 5,803 $28.87 $167,532.61
Disclosure

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

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 32,058

Read SEC document
March 11, 2024 Filed Mar 13, 2024 21:01 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantClass A Common Stock 22,505 $0.00 $0.00
Disclosure

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

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 37,861

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

Read SEC document
December 12, 2023 Filed Dec 14, 2023 02:45 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock 41,348 $10.22 $422,576.56
Disclosure

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

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

10b5-1 filing: No plan indicated

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 130,722

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

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

Read SEC document
December 11, 2023 Filed Dec 14, 2023 02:45 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock 77,930 $11.13 $867,360.90
Disclosure

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

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

10b5-1 filing: No plan indicated

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 172,070

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

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

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December 05, 2023 Filed Dec 8, 2023 00:59 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 ConversionClass A Common Units of Direct Digital Holdings LLC · Derivative 210,000 $0.00 $0.00
Disclosure

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

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

10b5-1 filing: No plan indicated

Ownership: Indirect · By Direct Digital Management, LLC

Disclosed balance after: 5,379,000

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

Expires not disclosed

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

F1 · derivative.exercise_price: Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings, LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person (indirectly through the Reporting Person's ownership interest in Direct Digital Management, LLC) are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

F1 · derivative.exercise_date: Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings, LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person (indirectly through the Reporting Person's ownership interest in Direct Digital Management, LLC) are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

F1 · derivative.expiration_date: Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings, LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person (indirectly through the Reporting Person's ownership interest in Direct Digital Management, LLC) are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

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December 05, 2023 Filed Dec 8, 2023 00:59 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 ConversionClass A Common Stock 210,000 Not disclosed Not disclosed
Disclosure

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

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

10b5-1 filing: No plan indicated

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 250,000

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

F1 · price: Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings, LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person (indirectly through the Reporting Person's ownership interest in Direct Digital Management, LLC) are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

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

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June 10, 2023 Filed Jun 13, 2023 22:31 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 20,097 $0.00 $0.00
Disclosure

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

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 40,803

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

Expires not disclosed

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

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F3 · derivative.exercise_date: On June 10, 2022, the reporting person was granted 60,900 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent will vest on June 10, 2024, and the remaining balance of 34 percent of the restricted stock units will vest on June 10, 2025. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

F3 · derivative.expiration_date: On June 10, 2022, the reporting person was granted 60,900 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33 percent of the restricted stock units vested on June 10, 2023, an additional 33 percent will vest on June 10, 2024, and the remaining balance of 34 percent of the restricted stock units will vest on June 10, 2025. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

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June 10, 2023 Filed Jun 13, 2023 22:31 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock 20,097 $0.00 $0.00
Disclosure

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

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 20,097

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

F1 · price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

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June 10, 2023 Filed Aug 24, 2023 01:32 UTC Amendment Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionRestricted Stock Units · Derivative 20,300 $0.00 $0.00
Disclosure

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

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 40,600

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

Expires not disclosed

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

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F4 · derivative.exercise_date: On June 10, 2022, the reporting person was granted 60,900 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on June 10, 2023, an additional 33% will vest on June 10, 2024, and the remaining balance of 34% of the restricted stock units will vest on June 10, 2025. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

F4 · derivative.expiration_date: On June 10, 2022, the reporting person was granted 60,900 restricted stock units, vesting in three annual installments beginning on the first anniversary of the grant date. 33% of the restricted stock units vested on June 10, 2023, an additional 33% will vest on June 10, 2024, and the remaining balance of 34% of the restricted stock units will vest on June 10, 2025. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

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June 10, 2023 Filed Aug 24, 2023 01:32 UTC Amendment Direct Digital Holdings, Inc. DRCT · Entity 2630 Tax withholdingClass A Common Stock 4,944 $3.25 $16,068.00
Disclosure

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

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 15,356

F2 · shares: Due to administrative error, the withholding of shares to satisfy the tax liability incident to the vesting of the restricted stock unit was inadvertently omitted from the original version of this report.

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June 10, 2023 Filed Aug 24, 2023 01:32 UTC Amendment Direct Digital Holdings, Inc. DRCT · Entity 2630 Exercise / conversionClass A Common Stock 20,300 Not disclosed Not disclosed
Disclosure

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

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 20,300

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

F1 · price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

Read SEC document
March 20, 2023 Filed Mar 22, 2023 21:01 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantEmployee Stock Options (right to buy) · Derivative 29,910 $0.00 Strike: $3.96 $0.00
Disclosure

SEC source: 0001104659-23-035652 · tm2310255-4_4seq1.xml · derivative · entry 3

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 29,910

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

Expires 2033-03-20

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

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March 20, 2023 Filed Mar 22, 2023 21:01 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantRestricted Stock Units · Derivative 29,910 $0.00 $0.00
Disclosure

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

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 29,910

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

Expires not disclosed

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F3 · derivative.exercise_date: The restricted stock units will vest in three equal annual installments, beginning on March 20, 2024. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

F3 · derivative.expiration_date: The restricted stock units will vest in three equal annual installments, beginning on March 20, 2024. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

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March 20, 2023 Filed Mar 22, 2023 21:01 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantRestricted Stock Units · Derivative 40,000 $0.00 $0.00
Disclosure

SEC source: 0001104659-23-035652 · tm2310255-4_4seq1.xml · derivative · entry 1

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

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 40,000

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

Expires not disclosed

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · derivative.exercise_date: The restricted stock units will vest 100% on March 20, 2024. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

F2 · derivative.expiration_date: The restricted stock units will vest 100% on March 20, 2024. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

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November 22, 2022 Filed Nov 25, 2022 21:16 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 PurchaseWarrants (right to buy) · Derivative 71,124 $0.35 Strike: $5.50 $24,893.40
Disclosure

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

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 71,124

Underlying: Class A Common Stock · 71,124 shares

Expires 2027-02-15

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

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August 26, 2022 Filed Aug 30, 2022 21:00 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 ConversionClass A Common Units of Direct Digital Holdings LLC · Derivative 100,000 $0.00 $0.00
Disclosure

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

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

10b5-1 filing: Not disclosed

Ownership: Indirect · By Direct Digital Management, LLC

Disclosed balance after: 5,589,000

Underlying: Class A Common Stock · 100,000 shares

Expires not disclosed

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

F1 · derivative.exercise_price: Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings, LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person (indirectly through the Reporting Person's ownership interest in Direct Digital Management, LLC) are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

F1 · derivative.exercise_date: Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings, LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person (indirectly through the Reporting Person's ownership interest in Direct Digital Management, LLC) are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

F1 · derivative.expiration_date: Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings, LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person (indirectly through the Reporting Person's ownership interest in Direct Digital Management, LLC) are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

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August 26, 2022 Filed Aug 30, 2022 21:00 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 SaleClass A Common Stock 60,000 $3.13 $187,800.00
Disclosure

SEC source: 0001104659-22-096094 · tm2224797d1_4.xml · nonDerivative · entry 2

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

10b5-1 filing: Not disclosed

Ownership: Indirect · By SKW Financial LLC

Disclosed balance after: 40,000

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

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August 26, 2022 Filed Aug 30, 2022 21:00 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 ConversionClass A Common Stock 100,000 Not disclosed Not disclosed
Disclosure

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

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

10b5-1 filing: Not disclosed

Ownership: Indirect · By Direct Digital Management, LLC

Disclosed balance after: 100,000

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

F1 · price: Pursuant to the Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings, LLC, dated as of February 15, 2022, Class A Common Units (as defined therein) held by the Reporting Person (indirectly through the Reporting Person's ownership interest in Direct Digital Management, LLC) are exchangeable for shares of Class A Common Stock on a one-for-one basis, subject to certain exceptions, conditions and adjustments. The Class A Common Units have no expiration date. At the time of any such exchange, an equal number of shares of Class B Common Stock of the Issuer held by the Reporting Person, which have no economic value and entitle holders thereof to one vote per share on all matters on which stockholders of the Issuer are entitled to vote generally, are cancelled.

F2 · ownership.nature: Upon receipt of the securities converted from Table II, Direct Digital Management, LLC distributed 100,000 shares of Class A Common Stock to one of its members, SKW Financial LLC, for no consideration. The Reporting Person, as owner of SKW Financial LLC and a Managing Partner of Direct Digital Management, LLC, may be deemed to have beneficial ownership of the securities directly held by SKW Financial LLC and Direct Digital Management, LLC.

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June 10, 2022 Filed Jun 13, 2022 20:57 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantEmployee Stock Options (right to buy) · Derivative 60,900 $0.00 Strike: $1.62 $0.00
Disclosure

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

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 60,900

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

Expires 2032-06-10

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

Read SEC document
June 10, 2022 Filed Jun 13, 2022 20:57 UTC Direct Digital Holdings, Inc. DRCT · Entity 2630 GrantRestricted Stock Units · Derivative 60,900 $0.00 $0.00
Disclosure

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

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

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 60,900

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

Expires not disclosed

F1 · derivative.exercise_price: Each restricted stock unit represents a contingent right to one share of DRCT's Class A Common Stock, par value $0.001 per share, upon settlement.

F2 · derivative.exercise_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

F2 · derivative.expiration_date: The restricted stock units will vest in three annual installments, with 33% to vest on each of the first and second anniversary of the grant date and the remaining 34% to vest on the third anniversary of the grant date. Vesting will be accelerated upon certain termination of employment events and upon a "Change in Control" (as defined in the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan).

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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.