Company: TIPT
Filing Date: 2025-10-31
Form Type: DEFM14A
Source: 0001140361-25-039949
Chunk: 24

Company: TIPTREE INC.
Filing Date: 2025-10-31
Form: DEFM14A
Chunk 24
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 from or in addition to the interests of our stockholders generally.

See the section of this proxy statement entitled “The Merger—Interests of Tiptree’s Directors and Executive Officers in the Merger” beginning on page 66 .

#### Financing of the Merger (Page66)
Purchaser anticipates that the total amount of funds necessary to consummate the Merger and the other transactions contemplated by the Merger Agreement will be approximately $1.68 billion. Purchaser expects to finance the Merger through cash on hand. The obligations of Purchaser and Merger Sub under the Merger Agreement are not conditioned upon their ability to obtain financing (or upon any cooperation by Tiptree in respect of any such financing).

**Material U.S. Federal Income Tax Consequences of the Merger (Page**

#### 67
#### )

For U.S. federal income tax purposes, the proposed Merger will be treated as a taxable sale of Fortegra common stock by Tiptree. The proposed Merger is entirely a corporate action undertaken by Tiptree. Our stockholders will not realize any direct taxable gain or loss on their shares of Tiptree common stock for U.S. federal income tax purposes as a result of the Merger, as our stockholders will not receive any direct proceeds from the Merger. We do not anticipate that the Merger or the other transactions contemplated by the Merger Agreement will result in any U.S. federal income tax consequences to our stockholders.

See the section of this proxy statement entitled “The Merger—Material U.S. Federal Income Tax Consequences of the Merger” beginning on page 67 and the section of this proxy statement entitled “Unaudited Pro Forma Condensed Consolidated Financial Statements” beginning on page 118 for additional information.

#### Stockholder Approval Requirement
The Tiptree Board is seeking stockholder approval of the Merger and the other transactions contemplated by the Merger Agreement because Tiptree is a Maryland corporation and the Merger may constitute a “transfer of assets” under Section 3-105 of the MGCL. Additionally, approval of the Merger Proposal by the affirmative vote of the holders of shares of Tiptree common stock entitled to cast a majority of all of the votes entitled to be cast on the Merger and the other transactions contemplated by the Merger Agreement is a closing condition under the Merger Agreement.

#### The Special Meeting (Page33)

#### Date, Time and Place
The special meeting of our stockholders to consider and vote