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Ilany Jonathan

Disclosed activity across 1 company

Tapewire entity
43510
SEC CIK
0001499150

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Reported relationships

Latest disclosed role at each company.

CompanyLast reported asReport datePublished
TIPTREE INC.TIPT · Entity 5239DirectorMay 27, 2026May 28, 2026

Disclosed balances

About these balances

Latest available filing per company, not a reconstructed current portfolio. Matching sequences show the last reported balance with all source rows expandable; grouping alone does not establish account ownership. Do not add unresolved positions together. Filings may omit unchanged positions, and amendments may correct only part of an older disclosure. Jointly reported shares are not necessarily this owner's personal holdings.

TIPTREE INC.

Report date May 27, 2026 · Filed May 28, 2026

Security / awardOwnership accountDisclosed shares / unitsDisclosure context
Common StockSEC Table I · non-derivativeIndirectBy IRA193,011 Reported balance After 2026-05-27 transaction · row 1 Account identity is unresolved; indirect or unspecified ownership is not merged.
1 source row

Row 1 · 2026-05-27 · Purchase · Acquired 990 · Balance 193,011

Common StockSEC Table I · non-derivativeDirect274,742 Reported balance Holding disclosure · report date 2026-05-27 · row 2 Holding and transaction disclosures are not merged.
1 source row

Row 2 · Balance 274,742

Transaction history

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Purchases/sales include open-market and private transactions. Plan disclosure applies to the filing; individual rows may differ. “Not disclosed” is not “unplanned.”

The cutoff filters transaction history only. Company summaries and owner relationships show the latest available disclosures. Parser corrections can improve historical records.

Transaction dateCompanyActivity / securityShares / unitsReported priceReported valueDetails
May 27, 2026 Filed May 28, 2026 20:01 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 990 $17.45 $17,275.50
Disclosure

SEC source: 0001499150-26-000002 · ownership.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · By IRA

Disclosed balance after: 193,011

Read SEC document
September 15, 2025 Filed Sep 17, 2025 20:05 UTC TIPTREE INC. TIPT · Entity 5239 Exercise / conversionEmployee Stock Option · Derivative 351,155 $6.65 Strike: $6.65 $2,335,180.75
Disclosure

SEC source: 0001193125-25-206158 · ownership.xml · derivative · entry 5

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 351,155 shares

Expires 2027-02-22

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F5 · security: 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.

F6 · derivative.exercise_date: The option shares are fully vested and exercisable as of February 22, 2022.

Read SEC document
September 15, 2025 Filed Sep 17, 2025 20:05 UTC TIPTREE INC. TIPT · Entity 5239 Tax withholdingCommon Stock 124,787 $23.70 $2,957,451.90
Disclosure

SEC source: 0001193125-25-206158 · ownership.xml · nonDerivative · entry 3

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 274,742

F4 · kind: 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.

F3 · price: Represents the closing stock price as of the transaction date.

Read SEC document
September 15, 2025 Filed Sep 17, 2025 20:05 UTC TIPTREE INC. TIPT · Entity 5239 Tax withholdingCommon Stock 98,531 $23.70 $2,335,184.70
Disclosure

SEC source: 0001193125-25-206158 · ownership.xml · nonDerivative · entry 2

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 399,529

F2 · kind: 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.

F3 · price: Represents the closing stock price as of the transaction date.

Read SEC document
September 15, 2025 Filed Sep 17, 2025 20:05 UTC TIPTREE INC. TIPT · Entity 5239 Exercise / conversionCommon Stock 351,155 $6.65 $2,335,180.75
Disclosure

SEC source: 0001193125-25-206158 · ownership.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 498,060

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · kind: 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.

Read SEC document
September 02, 2025 Filed Sep 4, 2025 20:01 UTC TIPTREE INC. TIPT · Entity 5239 Exercise / conversionEmployee Stock Option · Derivative 13,704 $5.87 Strike: $5.87 $80,442.48
Disclosure

SEC source: 0001499150-25-000005 · wk-form4_1757016106.xml · derivative · entry 8

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 13,704 shares

Expires 2026-03-10

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F8 · security: On March 10, 2016, the Reporting Person was granted non-qualified stock options to purchase 13,704 shares of common stock of the Registrant at $5.87 per share, subject to the terms of a Stock Option Agreement.

F9 · derivative.exercise_date: The option shares are fully vested and exercisable as of March 10, 2021.

Read SEC document
September 02, 2025 Filed Sep 4, 2025 20:01 UTC TIPTREE INC. TIPT · Entity 5239 Exercise / conversionEmployee Stock Option · Derivative 137,038 $5.67 Strike: $5.67 $777,005.46
Disclosure

SEC source: 0001499150-25-000005 · wk-form4_1757016106.xml · derivative · entry 7

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

Underlying: Common Stock · 137,038 shares

Expires 2026-01-04

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F6 · security: On January 4, 2016, the Reporting Person was granted non-qualified stock options to purchase 137,038 shares of common stock of the Registrant at $5.67 per share, subject to the terms of a Stock Option Agreement.

F7 · derivative.exercise_date: The option shares are fully vested and exercisable as of January 4, 2021.

Read SEC document
September 02, 2025 Filed Sep 4, 2025 20:01 UTC TIPTREE INC. TIPT · Entity 5239 Tax withholdingCommon Stock 53,128 $23.36 $1,241,070.08
Disclosure

SEC source: 0001499150-25-000005 · wk-form4_1757016106.xml · nonDerivative · entry 5

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 146,905

F5 · kind: 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.

F3 · price: Represents the closing stock price as of the transaction date.

Read SEC document
September 02, 2025 Filed Sep 4, 2025 20:01 UTC TIPTREE INC. TIPT · Entity 5239 Tax withholdingCommon Stock 3,444 $23.36 $80,451.84
Disclosure

SEC source: 0001499150-25-000005 · wk-form4_1757016106.xml · nonDerivative · entry 4

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 200,033

F4 · kind: Reflects 3,444 shares withheld by the Issuer at the market price of $23.36 per share less an exercise price of $5.87 per share to fund the cashless exercise of 13,704 options.

F3 · price: Represents the closing stock price as of the transaction date.

Read SEC document
September 02, 2025 Filed Sep 4, 2025 20:01 UTC TIPTREE INC. TIPT · Entity 5239 Exercise / conversionCommon Stock 13,704 $5.87 $80,442.48
Disclosure

SEC source: 0001499150-25-000005 · wk-form4_1757016106.xml · nonDerivative · entry 3

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 203,477

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · kind: 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.

Read SEC document
September 02, 2025 Filed Sep 4, 2025 20:01 UTC TIPTREE INC. TIPT · Entity 5239 Tax withholdingCommon Stock 33,262 $23.36 $777,000.32
Disclosure

SEC source: 0001499150-25-000005 · wk-form4_1757016106.xml · nonDerivative · entry 2

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 189,773

F2 · kind: Reflects 33,262 shares withheld by the Issuer at the market price of $23.36 per share less an exercise price of $5.67 per share to fund the cashless exercise of 137,038 options.

F3 · price: Represents the closing stock price as of the transaction date.

Read SEC document
September 02, 2025 Filed Sep 4, 2025 20:01 UTC TIPTREE INC. TIPT · Entity 5239 Exercise / conversionCommon Stock 137,038 $5.67 $777,005.46
Disclosure

SEC source: 0001499150-25-000005 · wk-form4_1757016106.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 223,035

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · kind: 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.

Read SEC document
February 25, 2025 Filed Feb 26, 2025 21:19 UTC TIPTREE INC. TIPT · Entity 5239 Tax withholdingCommon Stock 65,781 $21.67 $1,425,474.27
Disclosure

SEC source: 0001393726-25-000021 · wk-form4_1740604786.xml · nonDerivative · entry 2

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 85,997

F1 · kind: Represents the number of shares withheld to satisfy the Reporting Person's withholding tax liability upon the issuance of shares.

F2 · price: Represents the closing stock price as of the transaction date.

Read SEC document
February 25, 2025 Filed Feb 26, 2025 21:19 UTC TIPTREE INC. TIPT · Entity 5239 GrantCommon Stock 151,778 $0.00 $0.00
Disclosure

SEC source: 0001393726-25-000021 · wk-form4_1740604786.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 151,778

Read SEC document
October 17, 2024 Filed Oct 18, 2024 20:04 UTC TIPTREE INC. TIPT · Entity 5239 Exercise / conversionPerformance Restricted Stock Units 2021 · Derivative 200,000 $0.00 $0.00
Disclosure

SEC source: 0001393726-24-000090 · wk-form4_1729281885.xml · derivative · entry 4

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,200,000

Underlying: Common Stock · 200,000 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: These PRSUs were granted to the Reporting Person on August 4, 2021. The PRSUs will vest upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $30 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Each PRSU represents a contingent right to receive one share of Tiptree common stock. Any unvested PRSUs shall expire on August 4, 2031.

F3 · derivative.exercise_date: These PRSUs were granted to the Reporting Person on August 4, 2021. The PRSUs will vest upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $30 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Each PRSU represents a contingent right to receive one share of Tiptree common stock. Any unvested PRSUs shall expire on August 4, 2031.

F3 · derivative.expiration_date: These PRSUs were granted to the Reporting Person on August 4, 2021. The PRSUs will vest upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $30 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Each PRSU represents a contingent right to receive one share of Tiptree common stock. Any unvested PRSUs shall expire on August 4, 2031.

Read SEC document
October 17, 2024 Filed Oct 18, 2024 20:04 UTC TIPTREE INC. TIPT · Entity 5239 GiftCommon Stock 200,000 $0.00 $0.00
Disclosure

SEC source: 0001393726-24-000090 · wk-form4_1729281885.xml · nonDerivative · entry 2

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 0

F2 · kind: The reporting person gifted the vested portion of the PRSUs on October 17, 2024 to a family trust of which the reporting person has no control or beneficial interest.

Read SEC document
October 17, 2024 Filed Oct 18, 2024 20:04 UTC TIPTREE INC. TIPT · Entity 5239 Exercise / conversionCommon Stock 200,000 Not disclosed Not disclosed
Disclosure

SEC source: 0001393726-24-000090 · wk-form4_1729281885.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 200,000

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: The acquisition of the common stock resulted from the vesting of an equal number of performance restricted stock units ("PRSUs") upon achieving the $20 Tiptree Inc. ("Tiptree") share price target milestone (adjusted for dividends paid).

Read SEC document
May 28, 2024 Filed May 28, 2024 20:08 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 1,550 $17.50 $27,125.00
Disclosure

SEC source: 0001393726-24-000065 · wk-form4_1716926883.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Indirect · By 401K

Disclosed balance after: 192,021

Read SEC document
March 05, 2024 Filed Mar 6, 2024 19:23 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 2,900 $16.95 $49,155.00
Disclosure

SEC source: 0001393726-24-000037 · wk-form4_1709752986.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Indirect · By 401K

Disclosed balance after: 190,471

Read SEC document
January 09, 2024 Filed Jan 10, 2024 16:22 UTC TIPTREE INC. TIPT · Entity 5239 GiftCommon Stock 17,863 $0.00 $0.00
Disclosure

SEC source: 0001393726-24-000018 · wk-form4_1704903757.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 0

F1 · kind: Shares were a charitable donation to a donor advised fund.

Read SEC document
January 01, 2024 Filed Jan 2, 2024 21:06 UTC TIPTREE INC. TIPT · Entity 5239 GrantPerformance Restricted Stock Units 2024 · Derivative 550,000 $0.00 $0.00
Disclosure

SEC source: 0001393726-24-000004 · wk-form4_1704229594.xml · derivative · entry 3

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 550,000

Underlying: Common Stock · 550,000 shares

Expires not disclosed

F1 · derivative.exercise_price: Each performance restricted stock unit (PRSU) represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving a share price target milestone based on the average of the thirty (30) trading day closing stock price of $70 (adjusted for dividends paid) prior to the 10th anniversary of the grant date, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on January 1, 2034.

F1 · derivative.exercise_date: Each performance restricted stock unit (PRSU) represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving a share price target milestone based on the average of the thirty (30) trading day closing stock price of $70 (adjusted for dividends paid) prior to the 10th anniversary of the grant date, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on January 1, 2034.

F1 · derivative.expiration_date: Each performance restricted stock unit (PRSU) represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving a share price target milestone based on the average of the thirty (30) trading day closing stock price of $70 (adjusted for dividends paid) prior to the 10th anniversary of the grant date, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on January 1, 2034.

Read SEC document
June 07, 2023 Filed Jun 7, 2023 18:10 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 1,600 $14.27 $22,832.00
Disclosure

SEC source: 0001393726-23-000057 · wk-form4_1686161392.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: No plan indicated

Ownership: Indirect · By 401K

Disclosed balance after: 187,571

Read SEC document
March 13, 2023 Filed Mar 14, 2023 20:16 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 2,900 $15.00 $43,500.00
Disclosure

SEC source: 0001393726-23-000030 · wf-form4_167882496152939.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By 401K

Disclosed balance after: 185,971

Read SEC document
August 10, 2022 Filed Aug 11, 2022 17:09 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 1,916 $11.99 $22,965.18
Disclosure

SEC source: 0001393726-22-000076 · wf-form4_166023772644119.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By 401K

Disclosed balance after: 183,071

F1 · ownership.nature: The Reporting Person caused his indirectly held shares to be consolidated and transferred 144,019 shares from the IRA account into the 401K account.

Read SEC document
June 01, 2022 Filed Jun 2, 2022 20:11 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 400 $10.59 $4,236.00
Disclosure

SEC source: 0001393726-22-000044 · wf-form4_165420065382825.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By 401K

Disclosed balance after: 37,136

Read SEC document
March 16, 2022 Filed Mar 16, 2022 20:05 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 2,336 $12.58 $29,386.88
Disclosure

SEC source: 0001393726-22-000024 · wf-form4_164746112646534.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By 401K

Disclosed balance after: 36,736

Read SEC document
November 22, 2021 Filed Nov 22, 2021 22:03 UTC TIPTREE INC. TIPT · Entity 5239 Exercise / conversionPerformance Restricted Stock Units · Derivative 100,000 $0.00 $0.00
Disclosure

SEC source: 0001393726-21-000121 · wf-form4_163761856970650.xml · derivative · entry 5

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,400,000

Underlying: Common Stock · 100,000 shares

Expires not disclosed

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F3 · derivative.exercise_price: The PRSUs will vest upon Tiptree achieving each of five Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $15 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on August 4, 2031.

F3 · derivative.exercise_date: The PRSUs will vest upon Tiptree achieving each of five Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $15 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on August 4, 2031.

F3 · derivative.expiration_date: The PRSUs will vest upon Tiptree achieving each of five Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $15 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on August 4, 2031.

Read SEC document
November 22, 2021 Filed Nov 22, 2021 22:03 UTC TIPTREE INC. TIPT · Entity 5239 GiftCommon Stock 100,000 $0.00 $0.00
Disclosure

SEC source: 0001393726-21-000121 · wf-form4_163761856970650.xml · nonDerivative · entry 2

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 17,863

F2 · kind: The reporting person gifted the vested portion of the PRSUs on November 22, 2021 to a family trust of which the reporting person has no control or beneficial interest.

Read SEC document
November 22, 2021 Filed Nov 22, 2021 22:03 UTC TIPTREE INC. TIPT · Entity 5239 Exercise / conversionCommon Stock 100,000 Not disclosed Not disclosed
Disclosure

SEC source: 0001393726-21-000121 · wf-form4_163761856970650.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 117,863

Exercise/conversion can include RSU settlement. Transaction price and option strike are different fields; a missing price is not zero. Derivative and underlying rows can describe the same event.

F1 · price: The acquisition of the common stock resulted from the vesting of an equal number of performance restricted stock units ("PRSUs") granted on August 4, 2021. Each PRSU represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock.

Read SEC document
August 04, 2021 Filed Aug 5, 2021 18:20 UTC TIPTREE INC. TIPT · Entity 5239 GrantPerformance Restricted Stock Units · Derivative 1,500,000 $0.00 $0.00
Disclosure

SEC source: 0001393726-21-000095 · wf-form4_162818759465047.xml · derivative · entry 4

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 1,500,000

Underlying: Common Stock · 1,500,000 shares

Expires not disclosed

F1 · derivative.exercise_price: Each performance restricted stock unit ("PRSU") represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving each of five Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $15 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on August 4, 2031. See the Remarks below for the share price target milestones.

F1 · derivative.exercise_date: Each performance restricted stock unit ("PRSU") represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving each of five Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $15 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on August 4, 2031. See the Remarks below for the share price target milestones.

F1 · derivative.expiration_date: Each performance restricted stock unit ("PRSU") represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock. The PRSUs will vest upon Tiptree achieving each of five Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $15 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on August 4, 2031. See the Remarks below for the share price target milestones.

Read SEC document
June 04, 2021 Filed Jun 4, 2021 20:06 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 430 $10.00 $4,300.00
Disclosure

SEC source: 0001393726-21-000062 · wf-form4_162283718374132.xml · nonDerivative · entry 2

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By 401K

Disclosed balance after: 34,400

Read SEC document
June 04, 2021 Filed Jun 4, 2021 20:06 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 1,500 $9.96 $14,941.50
Disclosure

SEC source: 0001393726-21-000062 · wf-form4_162283718374132.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By IRA

Disclosed balance after: 144,019

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March 16, 2021 Filed Mar 17, 2021 15:45 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 4,000 $6.96 $27,836.00
Disclosure

SEC source: 0001393726-21-000023 · wf-form4_161599591112641.xml · nonDerivative · entry 2

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By 401K

Disclosed balance after: 33,970

F1 · price: This purchase was executed in multiple purchases at prices ranging from $6.76 to $6.96, inclusive. The price reported above reflects the weighted average price. The reporting person undertakes to provide to the issuer, any security holder of the issuer, or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares and prices at which the transaction was effected.

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March 16, 2021 Filed Mar 17, 2021 15:45 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 1,000 $7.83 $7,831.00
Disclosure

SEC source: 0001393726-21-000023 · wf-form4_161599591112641.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By IRA

Disclosed balance after: 142,519

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May 27, 2020 Filed May 28, 2020 14:17 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 3,400 $6.49 $22,066.00
Disclosure

SEC source: 0001393726-20-000160 · wf-form4_159067544476089.xml · nonDerivative · entry 2

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By IRA

Disclosed balance after: 141,519

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May 27, 2020 Filed May 28, 2020 14:17 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 530 $6.43 $3,405.25
Disclosure

SEC source: 0001393726-20-000160 · wf-form4_159067544476089.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By 401K

Disclosed balance after: 29,970

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March 16, 2020 Filed Mar 17, 2020 13:48 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 3,900 $6.25 $24,375.00
Disclosure

SEC source: 0001393726-20-000043 · wf-form4_158445288364168.xml · nonDerivative · entry 2

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By 401K

Disclosed balance after: 29,440

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March 13, 2020 Filed Mar 17, 2020 13:48 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 690 $5.25 $3,622.50
Disclosure

SEC source: 0001393726-20-000043 · wf-form4_158445288364168.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By 401K

Disclosed balance after: 25,540

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February 20, 2020 Filed Feb 21, 2020 22:11 UTC TIPTREE INC. TIPT · Entity 5239 GrantEmployee Stock Option · Derivative 255,166 $0.00 Strike: $7.25 $0.00
Disclosure

SEC source: 0001393726-20-000024 · wf-form4_158232304392163.xml · derivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 255,166

Underlying: Common Stock · 255,166 shares

Expires 2030-02-20

F1 · security: The Reporting Person was granted non-qualified stock options to purchase 255,166 shares of common stock of the Registrant, subject to the terms of a Stock Option Agreement between the Registrant and the Reporting person (the "Stock Option Agreement").

F2 · derivative.exercise_date: Exercise of the Stock Option is subject to both (1) a time-based vesting requirement with one-third vesting each of February 20, 2023, 2024 and 2025 and (2) a performance-based vesting requirement that, at any time during the option term, achievement of a 20-day volume weighted average stock price of Registrant's Common Stock, that exceeds the per share book value on an as exchanged basis as of December 31, 2019 (as reported in the Registrant's filings with the Securities and Exchange Commission).

F3 · derivative.expiration_date: The Stock Option will expire on the earlier of (1) February 20, 2030 and (2) the date of the termination of the Reporting Person's service with the Registrant for Cause (as defined in the Stock Option Agreement) or the Reporting Person's voluntary termination of service with the Registrant.

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June 03, 2019 Filed Jun 4, 2019 18:42 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 200 $6.07 $1,214.00
Disclosure

SEC source: 0001393726-19-000110 · wf-form4_155967375980740.xml · nonDerivative · entry 2

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By 401K

Disclosed balance after: 24,850

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June 03, 2019 Filed Jun 4, 2019 18:42 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 1,750 $6.08 $10,640.00
Disclosure

SEC source: 0001393726-19-000110 · wf-form4_155967375980740.xml · nonDerivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By IRA

Disclosed balance after: 138,119

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May 08, 2019 Filed May 9, 2019 14:07 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 4,500 $5.93 $26,685.00
Disclosure

SEC source: 0001393726-19-000090 · wf-form4_155741083630655.xml · nonDerivative · entry 2

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By 401K

Disclosed balance after: 24,650

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February 26, 2019 Filed Feb 28, 2019 18:19 UTC TIPTREE INC. TIPT · Entity 5239 GrantEmployee Stock Option · Derivative 135,489 $0.00 Strike: $6.26 $0.00
Disclosure

SEC source: 0001393726-19-000031 · wf-form4_155137795833167.xml · derivative · entry 1

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Direct

Disclosed balance after: 135,489

Underlying: Common Stock · 135,489 shares

Expires not disclosed

F1 · security: The Reporting Person was granted non-qualified stock options to purchase 135,489 shares of common stock of the Registrant, subject to the terms of a Stock Option Agreement between the Registrant and the Reporting person (the "Stock Option Agreement").

F2 · derivative.exercise_date: Exercise of the Stock Option is subject to both (1) a time-based vesting requirement with one-third vesting each of February 26, 2022, 2023 and 2024 and (2) a performance-based vesting requirement that, at any time during the option term, achievement of a 20-day volume weighted average stock price of Registrant's Common Stock, that exceeds the per share book value on an as exchanged basis as of December 31, 2018 (as reported in the Registrant's filings with the Securities and Exchange Commission).

F3 · derivative.expiration_date: The Stock Option will expire on the earlier of (1) February 26, 2029 and (2) the date of the termination of Jonathan Ilany's service with the Registrant for Cause (as defined in the Stock Option Agreement) or Jonathan Ilany's voluntary termination of service with the Registrant.

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December 07, 2018 Filed Dec 10, 2018 18:08 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 600 $5.33 $3,198.00
Disclosure

SEC source: 0001393726-18-000065 · wf-form4_154446530818251.xml · nonDerivative · entry 3

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By 401K

Disclosed balance after: 156,519

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December 07, 2018 Filed Dec 10, 2018 18:08 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseCommon Stock 3,200 $5.33 $17,056.00
Disclosure

SEC source: 0001393726-18-000065 · wf-form4_154446530818251.xml · nonDerivative · entry 2

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By IRA

Disclosed balance after: 155,919

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March 16, 2018 Filed Mar 16, 2018 20:20 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseClass A Common Stock 600 $6.72 $4,032.00
Disclosure

SEC source: 0001628280-18-003304 · wf-form4_152123159084737.xml · nonDerivative · entry 6

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By IRA

Disclosed balance after: 152,719

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March 16, 2018 Filed Mar 16, 2018 20:20 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseClass A Common Stock 2,295 $6.20 $14,229.00
Disclosure

SEC source: 0001628280-18-003304 · wf-form4_152123159084737.xml · nonDerivative · entry 5

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By 401K

Disclosed balance after: 152,119

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March 16, 2018 Filed Mar 16, 2018 20:20 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseClass A Common Stock 607 $6.15 $3,733.05
Disclosure

SEC source: 0001628280-18-003304 · wf-form4_152123159084737.xml · nonDerivative · entry 4

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By 401K

Disclosed balance after: 149,824

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March 16, 2018 Filed Mar 16, 2018 20:20 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseClass A Common Stock 100 $6.10 $610.00
Disclosure

SEC source: 0001628280-18-003304 · wf-form4_152123159084737.xml · nonDerivative · entry 3

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By 401K

Disclosed balance after: 149,217

Read SEC document
March 16, 2018 Filed Mar 16, 2018 20:20 UTC TIPTREE INC. TIPT · Entity 5239 PurchaseClass A Common Stock 977 $6.05 $5,910.85
Disclosure

SEC source: 0001628280-18-003304 · wf-form4_152123159084737.xml · nonDerivative · entry 2

Ilany Jonathan · CIK 0001499150 · Director · Chief Executive Officer

10b5-1 filing: Not disclosed

Ownership: Indirect · By 401K

Disclosed balance after: 149,117

Read SEC document

Value uses the disclosed total when available, otherwise shares × reported transaction price. It is not an estimate of exercise cash cost or investment performance.