Company: TIPT
Filing Date: 2025-10-17
Form Type: PREM14A
Source: 0001140361-25-038514
Chunk: 59

Company: TIPTREE INC.
Filing Date: 2025-10-17
Form: PREM14A
Chunk 59
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 in Tiptree’s or Fortegra’s business or operating results; |

| • | any disruption of Tiptree or Fortegra management’s ability to spend time on the ongoing business operations of Tiptree and Fortegra due to the Merger; |

| • | limitations placed on Fortegra’s ability to operate the business by the Merger Agreement; |

| • | failure to complete the Merger in a timely manner or at all; |

| • | failure of Tiptree to realize financial benefits currently anticipated from the Merger; |

| • | competitive pressures in the markets in which Tiptree and Fortegra operate; |

| • | the effects of market volatility or macroeconomic changes and financial market regulations on the industries in which Tiptree operates; |

| • | the effects of changes in, or our failure to comply with, laws and regulations; and |

| • | cybersecurity attacks or information system failures disrupting Tiptree’s or Fortegra’s businesses. |

For additional information about risks and uncertainties that may cause actual results of the Merger and the other transactions contemplated by the Merger Agreement to differ materially from those described, please refer to our reports filed with the SEC, including without limitation the “Risk Factors” and/or other information included in such reports. While the list of factors presented here is considered representative, no such list should be considered to be a complete statement of all risks and uncertainties. Unlisted factors may present significant additional obstacles to the realization of forward-looking statements. The forward-looking statements in this proxy statement speak only as of the date of this proxy statement. Except as required by law, we assume no obligation to update or revise these forward-looking statements for any reason, even if new information becomes available in the future.

27

#### TABLE OF CONTENTS

### RISK FACTORS
**In addition to the other information included and referred to in this proxy statement, including the matters addressed in the section of this proxy statement entitled “Cautionary Statement Regarding Forward-Looking Statements,” beginning on page 27 , you should carefully consider the following risk factors before deciding how to vote your shares of Tiptree common stock at the special meeting. These factors should be considered in conjunction with the other information included by Tiptree in this proxy statement and the risk factors described in Tiptree’s other filings with the SEC, including in the “Risk Factors” sections of Tiptree’s Annual Report on Form 10-K for the fiscal year ended December 31, 2024, as filed