Company: TIPT
Filing Date: 2025-11-25
Form Type: DEFA14A
Source: 0001140361-25-043224
Chunk: 2

Company: TIPTREE INC.
Filing Date: 2025-11-25
Form: DEFA14A
Chunk 2
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 the Proxy Statement. All page references below are to pages in the Proxy Statement, and terms used below, unless otherwise defined herein, have the meanings given to such terms in the Proxy Statement. Paragraph references used herein refer to the Proxy Statement before any additions or deletions resulting from the supplemental disclosures. The information contained herein speaks only as of the date of this Supplement, unless the information indicates another date applies. Except as specifically noted herein, the information set forth in the Proxy Statement remains unchanged. This Supplement supplements and updates the disclosures in the Proxy Statement as follows (new text is underlined; deleted text is lined-out):

| • | Under “Selected Comparable Company Analysis” on page 58, replace the paragraph    
 starting with “The results of this” and the chart that follow with the following: |

| The results of this warranty comparable company analysis aresummarizedlistedbelow: |

| MetricPeers            |     | Second Quarter  
 2025 Actual     
 (“Q2’25A”) P/BV |     | Q2'25A 
 P/TBV  |     | Non-     
 GAAP     
 P/E '26E |
| WarrantyAssurant, Inc. |     | 1.92x           |     | 4.52x  |     | 10.7x    |

The results of this selected specialty comparable company analysis are listed below:

| Metric(1)                                  |     | Low   |     | Median |     | Mean  |     | High  |
| Second Quarter 2025 Actual (“Q2’25A”) P/BV |     | 0.96x |     | 2.13x  |     | 2.12x |     | 5.80x |
| Q2'25A P/TBV                               |     | 0.97x |     | 2.23x  |     | 2.28x |     | 5.81x |
| Non-GAAP P/E '26E                          |     | 5.4x  |     | 12.5x  |     | 12.8x |     | 20.8x |

| Peers                                   |     | Second Quarter  
 2025 Actual     
 (“Q2’25A”) P/BV |     | Q2'25A 
 P/TBV  |     | Non-     
 GAAP     
 P/E '26E |
| Arch Capital Group Ltd.                 |     |