Jonathan Ilany - 15 Sep 2025 Form 4 Insider Report for TIPTREE INC. (TIPT)

Reporting relationship: Chief Executive Officer, Director
Issuer ticker: TIPT
Reported as of: 15 Sep 2025
Net transaction value: -$5,292,637
SEC form: 4
Accepted by SEC: 17 Sep 2025, 16:05:40 UTC
Prior SEC filing: 04 Sep 2025
Next SEC filing: 28 May 2026
Source filing: View source filing
Reporting owner signature: /s/ Neil C. Rifkind as Attorney-in-Fact for Jonathan Ilany

Key filing fact

Jonathan Ilany filed Form 4 for TIPTREE INC. (TIPT) on 17 Sep 2025.

Key facts

This page summarizes Jonathan Ilany's Form 4 filing for TIPTREE INC. (TIPT).
4 reported transactions and 1 derivative row are listed below.
Accepted by SEC: 17 Sep 2025, 16:05.

Change

Previous filing in this sequence was filed on 04 Sep 2025.
Current net transaction value: -$5,292,637.

Research use

This tells you what this filing adds before you inspect full transaction and derivative tables.
You can trace every row back to the original SEC filing document.

Evidence

Filed on Form 4

Ownership activity is grounded in SEC Form 4 disclosures.

View source filing

Reporting Owners (1)

CIK 0001499150 Primary reporting owner

Ilany Jonathan

Relationship: Chief Executive Officer, Director
Address: C/O TIPTREE INC., 660 STEAMBOAT ROAD, GREENWICH
Signature: /s/ Neil C. Rifkind as Attorney-in-Fact for Jonathan Ilany
Signature date: 17 Sep 2025

Reported non-derivative transactions

Shares, units, or other non-derivative securities reported in this filing.

TIPT transaction

Common Stock

Options Exercise

Transaction value: $2,335,181
Shares: +351,155
Change %: +239%
Price: $6.65
Shares after: 498,060
Date: 15 Sep 2025
Ownership: Direct
Footnotes: F1

TIPT transaction

Common Stock

Tax liability

Transaction value: $2,335,185
Shares: -98,531
Change %: -20%
Price: $23.70
Shares after: 399,529
Date: 15 Sep 2025
Ownership: Direct
Footnotes: F2, F3

TIPT transaction

Common Stock

Tax liability

Transaction value: $2,957,452
Shares: -124,787
Change %: -31%
Price: $23.70
Shares after: 274,742
Date: 15 Sep 2025
Ownership: Direct
Footnotes: F3, F4

TIPT holding

Common Stock

No transaction description listed

Transaction value
Shares
Change %
Price
Shares after: 192,021
Date: 15 Sep 2025
Ownership: By 401K

Reported derivative securities

Options, warrants, convertible securities, or similar derivative positions disclosed in the filing.

TIPT transaction Derivative

Employee Stock Option

Options Exercise

Transaction value: $2,335,181
Shares: -351,155
Change %: -100%
Price: $6.65
Shares after: 0
Date: 15 Sep 2025
Ownership: Direct
Underlying class: Common Stock
Underlying amount: 351,155
Exercise price: $6.65
Footnotes: F5, F6

^* marks a reported price that did not pass the local price check.

Additional SEC filing notes

Filing notes and footnotes

Explanation of responses 6 footnotes

Footnote F1

The transactions reported above in Table I reflect the cashless exercise of stock options. The cashless exercise for the options is reported in two lines. The lines coded M in column 3 of Table I report in column 4 the number of shares issuable upon exercise of the options had cash been paid to exercise the options, together with the exercise price with Code A for acquired. The lines coded F in column 3 of Table I relates to the same cashless exercise on the preceding line and reports in Column 4 the number of shares deducted from the total number of shares issuable to pay for the cashless exercise of such options with Code D for disposed.

Footnote F2

Reflects 98,531 shares withheld by the Issuer at the market price of $23.70 per share less an exercise price of $6.65 per share to fund the cashless exercise of 351,155 options.

Footnote F3

Represents the closing stock price as of the transaction date.

Footnote F4

Represents the number of shares withheld to satisfy the Reporting Person's withholding tax liability upon the issuance of options exercised cashless calculated at the closing stock price of the exercise date.

Footnote F5

On February 22, 2017, the Reporting Person was granted non-qualified stock options to purchase 351,155 shares of common stock of the Registrant at $6.65 per share, subject to the terms of a Stock Option Agreement.

Footnote F6

The option shares are fully vested and exercisable as of February 22, 2022.