Company: TIPT
Filing Date: 2025-10-31
Form Type: DEFM14A
Source: 0001140361-25-039949
Chunk: 2

Company: TIPTREE INC.
Filing Date: 2025-10-31
Form: DEFM14A
Chunk 2
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 A Liquidation Preference (as defined in this proxy statement).

Tiptree estimates that Tiptree will receive total gross proceeds of approximately $1.12 billion in cash upon consummation of the Merger, subject to adjustments for Leakage (as defined in this proxy statement) and assuming a closing date for the transactions contemplated by the Merger Agreement prior to June 1, 2026, having an estimated book value of approximately $930 million as of September 30, 2025, net of estimated transaction-related taxes and expenses. Tiptree intends to use proceeds from the Merger for working capital and general corporate purposes, including to pay transaction expenses, to pay taxes on the transactions contemplated by the Merger Agreement, to repay existing debt of Tiptree, to engage in opportunistic stock repurchases and/or pay dividends, to purchase additional assets or businesses and/or for any other purpose that the Tiptree board of directors (the “Tiptree Board”) deems appropriate.

We are soliciting proxies from our stockholders for exercise at the special meeting or any postponement or adjournment thereof to consider and vote upon: (i) the Merger Proposal and (ii) the proposal to approve one or more

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adjournments of the special meeting, if necessary, to solicit additional proxies, in the event that there are insufficient votes to approve the Merger Proposal at the special meeting. All stockholders should read the accompanying proxy statement and the documents included with the accompanying proxy statement carefully and in their entirety.

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 Maryland General Corporation Law. Additionally, approval of the Merger Proposal by the affirmative vote of the holders of shares of Tiptree common stock, par value $0.001 per share (“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 Tiptree Board, after considering the reasons more fully described in the accompanying proxy statement, has unanimously: (i) determined that the Merger and the other transactions contemplated by the Merger Agreement are advisable and in the best interests of Tiptree and its stockholders; (ii) approved the execution and