Company: TIPT
Filing Date: 2025-03-17
Form Type: DEF 14A
Source: 0001393726-25-000038
Chunk: 7

Company: TIPTREE INC.
Filing Date: 2025-03-17
Form: DEF 14A
Chunk 7
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 best measured over the long term and that long term growth in our stock price plus dividends paid is the best metric for evaluating our performance. The table below shows growth in our stock price plus dividends paid annually during the one, three and five year period from December 31, 2024 and since inception (1) (June 2007), compared with the S&P 500 and Russell 2000, with all values calculated with dividends reinvested.

|                |     | Tiptree |     | S&P 500 |     | Russell 2000 |
| 1 Year         |     | 12.6%   |     | 25.0%   |     | 11.5%        |
| 3 Year         |     | 16.4%   |     | 8.9%    |     | 1.2%         |
| 5 Year         |     | 22.6%   |     | 14.5%   |     | 7.4%         |
| 10 Year        |     | 11.3%   |     | 13.1%   |     | 7.8%         |
| From Jun’07(1) |     | 10.7%   |     | 10.3%   |     | 7.3%         |

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(1) At Tiptree’s founding in 2007, book value per share was $5.36. Cumulative dividends paid from 2007 to December 31, 2024 represented $3.53 per share.

<div align='center'>4</div>

#### Stock Performance Graph
Set forth below is a line-graph presentation comparing the cumulative total return on our common stock against cumulative total returns of the Russell 2000 and the S&P Select Sector Financial Services Index (1) . The performance graph shows the total return on an investment of $100 for the period beginning December 31, 2019 (the last trading date) and ending December 31, 2024 assuming reinvestment of dividends. The stockholder return shown on the graph below is not necessarily indicative of future performance, and we will not make or endorse any predictions as to future stockholder returns.

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(1) We believe it is difficult to develop a peer group of companies similar to Tiptree as Tiptree owns subsidiaries engaged in a number of diverse business activities. However, management views Tiptree and its