| Date | Name | Symbol | Type | Security | Shares | Price | Value | Ownership | Reported |
| 02/07/2023 | TIPTREE INC. | TIPT | Payment of Exercise | Common Stock | 9.3k | $15.88 | $148.4k | | 02/07/2023 |
| 02/07/2023 | TIPTREE INC. | TIPT | Payment of Exercise | Common Stock | 967 | $15.88 | $15.4k | | 02/07/2023 |
| 02/07/2023 | TIPTREE INC. | TIPT | Payment of Exercise | Common Stock | 26.3k | $15.88 | $418k | | 02/07/2023 |
| 02/07/2023 | TIPTREE INC. | TIPT | Exercise | January 2016 Stock Option | 26.2k | $5.67 | $148.4k | | 02/07/2023 |
| 02/07/2023 | TIPTREE INC. | TIPT | Exercise | March 2016 Stock Option | 2.6k | $5.87 | $15.4k | | 02/07/2023 |
| 02/07/2023 | TIPTREE INC. | TIPT | Exercise | February 2017 Stock Option | 62.9k | $6.65 | $418k | | 02/07/2023 |
| 09/01/2022 | TIPTREE INC. | TIPT | Grant | | 26.2k | $5.67 | $148.4k | | 09/01/2022 |
| 09/01/2022 | TIPTREE INC. | TIPT | Grant | | 2.6k | $5.87 | $15.4k | | 09/01/2022 |
| 09/01/2022 | TIPTREE INC. | TIPT | Grant | | 62.9k | $6.65 | $418k | | 09/01/2022 |
| 06/27/2022 | TIPTREE INC. | TIPT | Exercise | Tiptree Inc. warrant 2022 | 440.3k | $6.93 | $3.1M | | 06/27/2022 |
| 03/17/2021 | TIPTREE INC. | TIPT | Purchase | Common Stock | 48.3k | $7.68 | $370.9k | | 03/17/2021 |
| 03/17/2021 | TIPTREE INC. | TIPT | Purchase | Common Stock | 36.7k | $8.87 | $325.5k | | 03/17/2021 |
| 03/16/2021 | TIPTREE INC. | TIPT | Purchase | Common Stock | 39.1k | $7.32 | $286.1k | | 03/16/2021 |
| 03/16/2021 | TIPTREE INC. | TIPT | Purchase | Common Stock | 900 | $7.87 | $7.1k | | 03/16/2021 |
| 04/10/2018 | TIPTREE INC. | TIPT | Other (acquisition) | Class A Common Stock | 1.7M | $0.00 | $0 | | 04/10/2018 |
| 04/10/2018 | TIPTREE INC. | TIPT | Other (disposition) | Tiptree Financial Partners, L.P. partnership unit | 616.4k | $0.00 | $0 | | 04/10/2018 |
| 04/10/2018 | TIPTREE INC. | TIPT | Other (disposition) | Tiptree Financial Partners, L.P. partnership unit warrant | 143.7k | $7.59 | $1.1M | | 04/10/2018 |
| 04/10/2018 | TIPTREE INC. | TIPT | Other (acquisition) | Tiptree Inc. warrant 2018 | 26.1k | $11.33 | $296.1k | | 04/10/2018 |
| 04/10/2018 | TIPTREE INC. | TIPT | Other (acquisition) | Tiptree Inc. warrant 2022 | 401.9k | $7.59 | $3.1M | | 04/10/2018 |
| 12/18/2017 | TIPTREE INC. | TIPT | Other (acquisition) | Tiptree Financial Partners, L.P. partnership unit | 395.7k | $0.00 | $0 | | 12/18/2017 |
| 12/18/2017 | TIPTREE INC. | TIPT | Other (acquisition) | Tiptree Financial Partners, L.P. partnership unit warrant | 143.6k | $7.59 | $1.1M | | 12/18/2017 |
| 11/21/2017 | TIPTREE INC. | TIPT | Purchase | Class A Common Stock | 100 | $6.95 | $695 | | 11/21/2017 |
| 11/21/2017 | TIPTREE INC. | TIPT | Purchase | Class A Common Stock | 32.4k | $7.00 | $226.5k | | 11/21/2017 |
| 11/21/2017 | TIPTREE INC. | TIPT | Purchase | Class A Common Stock | 200 | $7.03 | $1.4k | | 11/21/2017 |
| 11/21/2017 | TIPTREE INC. | TIPT | Purchase | Class A Common Stock | 16.7k | $7.05 | $117.7k | | 11/21/2017 |
| 11/21/2017 | TIPTREE INC. | TIPT | Purchase | Class A Common Stock | 20.6k | $7.15 | $147.6k | | 11/21/2017 |
| 06/06/2017 | TIPTREE INC. | TIPT | Other (acquisition) | Class A Common Stock | 506k | $5.36 | $2.7M | | 06/05/2017 |
| 06/05/2017 | TIPTREE INC. | TIPT | Other (disposition) | Tiptree Financial Partners, L.P. partnership unit option | 1.5M | $5.36 | $8.1M | By: Tricadia Capital Management, LLC | 06/05/2017 |
| 04/11/2017 | TIPTREE INC. | TIPT | Other (acquisition) | Class A Common Stock | 9k | $0.00 | $0 | | 04/11/2017 |
| 04/10/2017 | TIPTREE INC. | TIPT | Other (acquisition) | Class A Common Stock | 16.1k | $0.00 | $0 | | 04/10/2017 |
| 03/10/2016 | TIPTREE INC. | TIPT | Grant | Class A Common Stock | 4.6k | $0.00 | $0 | By: Tricadia Holdings, L.P. | 03/10/2016 |
| 03/10/2016 | TIPTREE INC. | TIPT | Grant | | 9.1k | $5.87 | $53.6k | By: Tricadia Holdings, L.P. | 03/10/2016 |
| 01/04/2016 | TIPTREE INC. | TIPT | Other (acquisition) | Tiptree Financial Partners, L.P. partnership unit warrant | 598 | $7.54 | $4.5k | By: TFPLP Holdings I LLC and TFPLP Holdings III LLC | 01/01/2016 |
| 01/04/2016 | TIPTREE INC. | TIPT | Grant | Class A Common Stock | 45.7k | $0.00 | $0 | By: Tricadia Holdings, L.P. | 01/04/2016 |
| 01/04/2016 | TIPTREE INC. | TIPT | Grant | | 91.4k | $5.67 | $518k | By: Tricadia Holdings, L.P. | 01/04/2016 |
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