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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."},{"field":"price","element":"transactionPricePerShare","label":"F3","text":"Represents the closing stock price as of the transaction date."}],"balance_after":399529,"source":{"system":"sec-edgar","filing":"0001193125-25-206158","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1499150/000119312525206158/ownership.xml","form_type":"4"}},{"id":1037724,"issuer":{"id":5239,"kind":"organization","name":"TIPTREE INC.","symbol":"TIPT"},"owners":[{"id":43510,"kind":"person","name":"Ilany Jonathan","position":1,"cik":"0001499150","reported_name":"Ilany Jonathan","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common 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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."}],"balance_after":498060,"source":{"system":"sec-edgar","filing":"0001193125-25-206158","document":"ownership.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1499150/000119312525206158/ownership.xml","form_type":"4"}},{"id":1047879,"issuer":{"id":5239,"kind":"organization","name":"TIPTREE INC.","symbol":"TIPT"},"owners":[{"id":43510,"kind":"person","name":"Ilany Jonathan","position":1,"cik":"0001499150","reported_name":"Ilany Jonathan","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Employee Stock 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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."}],"balance_after":203477,"source":{"system":"sec-edgar","filing":"0001499150-25-000005","document":"wk-form4_1757016106.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":3,"url":"https://www.sec.gov/Archives/edgar/data/1499150/000149915025000005/wk-form4_1757016106.xml","form_type":"4"}},{"id":1047874,"issuer":{"id":5239,"kind":"organization","name":"TIPTREE INC.","symbol":"TIPT"},"owners":[{"id":43510,"kind":"person","name":"Ilany Jonathan","position":1,"cik":"0001499150","reported_name":"Ilany Jonathan","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2025-09-04T20:01:49.000Z","date":"2025-09-02","kind":"tax_withholding","planned":false,"acquired":false,"shares":33262,"price":23.36,"value":777000.32,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F2","text":"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."},{"field":"price","element":"transactionPricePerShare","label":"F3","text":"Represents the closing stock price as of the transaction date."}],"balance_after":189773,"source":{"system":"sec-edgar","filing":"0001499150-25-000005","document":"wk-form4_1757016106.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1499150/000149915025000005/wk-form4_1757016106.xml","form_type":"4"}},{"id":1047873,"issuer":{"id":5239,"kind":"organization","name":"TIPTREE INC.","symbol":"TIPT"},"owners":[{"id":43510,"kind":"person","name":"Ilany Jonathan","position":1,"cik":"0001499150","reported_name":"Ilany Jonathan","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2025-09-04T20:01:49.000Z","date":"2025-09-02","kind":"exercise","planned":false,"acquired":true,"shares":137038,"price":5.67,"value":777005.46,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"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."}],"balance_after":223035,"source":{"system":"sec-edgar","filing":"0001499150-25-000005","document":"wk-form4_1757016106.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1499150/000149915025000005/wk-form4_1757016106.xml","form_type":"4"}},{"id":1243028,"issuer":{"id":5239,"kind":"organization","name":"TIPTREE INC.","symbol":"TIPT"},"owners":[{"id":43510,"kind":"person","name":"Ilany Jonathan","position":1,"cik":"0001499150","reported_name":"Ilany Jonathan","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2025-02-26T21:19:55.000Z","date":"2025-02-25","kind":"tax_withholding","planned":false,"acquired":false,"shares":65781,"price":21.67,"value":1425474.27,"ownership":{"direct":true},"footnotes":[{"field":"kind","element":"transactionCoding","label":"F1","text":"Represents the number of shares withheld to satisfy the Reporting Person's withholding tax liability upon the issuance of shares."},{"field":"price","element":"transactionPricePerShare","label":"F2","text":"Represents the closing stock price as of the transaction date."}],"balance_after":85997,"source":{"system":"sec-edgar","filing":"0001393726-25-000021","document":"wk-form4_1740604786.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":2,"url":"https://www.sec.gov/Archives/edgar/data/1499150/000139372625000021/wk-form4_1740604786.xml","form_type":"4"}},{"id":1243027,"issuer":{"id":5239,"kind":"organization","name":"TIPTREE INC.","symbol":"TIPT"},"owners":[{"id":43510,"kind":"person","name":"Ilany Jonathan","position":1,"cik":"0001499150","reported_name":"Ilany Jonathan","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Common Stock","published_at":"2025-02-26T21:19:55.000Z","date":"2025-02-25","kind":"grant","planned":false,"acquired":true,"shares":151778,"price":0,"value":0.0,"ownership":{"direct":true},"balance_after":151778,"source":{"system":"sec-edgar","filing":"0001393726-25-000021","document":"wk-form4_1740604786.xml","document_sequence":1,"table":"nonDerivative","row_type":"transaction","position":1,"url":"https://www.sec.gov/Archives/edgar/data/1499150/000139372625000021/wk-form4_1740604786.xml","form_type":"4"}},{"id":1384052,"issuer":{"id":5239,"kind":"organization","name":"TIPTREE INC.","symbol":"TIPT"},"owners":[{"id":43510,"kind":"person","name":"Ilany Jonathan","position":1,"cik":"0001499150","reported_name":"Ilany Jonathan","relationship":{"director":true,"officer":true,"ten_percent_owner":false,"other":false,"officer_title":"Chief Executive Officer"}}],"security":"Performance Restricted Stock Units 2021","published_at":"2024-10-18T20:04:52.000Z","date":"2024-10-17","kind":"exercise","planned":false,"acquired":false,"shares":200000,"price":0,"value":0.0,"ownership":{"direct":true},"footnotes":[{"field":"derivative.exercise_price","element":"conversionOrExercisePrice","label":"F3","text":"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."},{"field":"derivative.exercise_date","element":"exerciseDate","label":"F3","text":"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. 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