Notes and Accounts Receivable, net -Schedule of Notes and Accounts Receivable, Net (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2019	Dec. 31, 2018	Dec. 31, 2017
Accounts, Notes, Loans and Financing Receivable [Line Items]
Accounts and premiums receivable, net	$ 50,712	$ 50,880
Retrospective commissions receivable	105,387	84,488
Trust receivables	63,925	53,424
Other Receivables	24,752	21,256
Total	286,968	223,105
Bad debt expense	140	243	$ 1,019
Accounts and premiums receivable
Accounts, Notes, Loans and Financing Receivable [Line Items]
Allowance for Doubtful Accounts Receivable	109	217
Bad debt expense	36	39	48
Tiptree Insurance | Notes Receivable
Accounts, Notes, Loans and Financing Receivable [Line Items]
Notes receivable, net - premium financing program (1)	42,192	13,057
Allowance for Doubtful Accounts Receivable	95	97
Bad debt expense	175	195	$ 374
Financing Receivables, Equal to Greater than 90 Days Past Due | Tiptree Insurance | Notes Receivable
Accounts, Notes, Loans and Financing Receivable [Line Items]
Financing Receivable, Recorded Investment, 90 Days Past Due and Still Accruing	$ 93	$ 368