| Date | Name | Symbol | Type | Security | Shares | Price | Value | Ownership | Reported |
| 06/10/2023 | Direct Digital Holdings, Inc. | | Payment of Exercise | Class A Common Stock | 4.9k | $3.25 | $16.1k | | 06/10/2023 |
| 06/10/2023 | Direct Digital Holdings, Inc. | | Exercise | Restricted Stock Units | 20.3k | $0.00 | $0 | | 06/10/2023 |
| 03/20/2023 | Direct Digital Holdings, Inc. | | Grant | Employee Stock Options (right to buy) | 29.9k | $3.96 | $118.4k | | 03/20/2023 |
| 03/20/2023 | Direct Digital Holdings, Inc. | | Grant | Restricted Stock Units | 29.9k | $0.00 | $0 | | 03/20/2023 |
| 03/20/2023 | Direct Digital Holdings, Inc. | | Grant | Restricted Stock Units | 40k | $0.00 | $0 | | 03/20/2023 |
| 11/22/2022 | Direct Digital Holdings, Inc. | | Purchase | Warrants (right to buy) | 71.1k | $5.50 | $391.2k | | 11/22/2022 |
| 08/26/2022 | Direct Digital Holdings, Inc. | | Conversion | Class A Common Units of Direct Digital Holdings LLC | 100k | $0.00 | $0 | By Direct Digital Management, LLC | 08/26/2022 |
| 08/26/2022 | Direct Digital Holdings, Inc. | | Sale | Class A Common Stock | 60k | $3.13 | $187.8k | By SKW Financial LLC | 08/26/2022 |
| 08/26/2022 | Direct Digital Holdings, Inc. | | Conversion | Class A Common Stock | 100k | $0.00 | $0 | By Direct Digital Management, LLC | 08/26/2022 |
| 06/10/2022 | Direct Digital Holdings, Inc. | | Grant | Restricted Stock Units | 60.9k | $0.00 | $0 | | 06/10/2022 |
| 06/10/2022 | Direct Digital Holdings, Inc. | | Grant | Employee Stock Options (right to buy) | 60.9k | $1.62 | $98.7k | | 06/10/2022 |
| 01/09/2010 | DENTSPLY SIRONA Inc. | XRAY | Grant | | 4.46 | $35.44 | $158.1 | | 01/09/2010 |