Notes and Accounts Receivable, net -Schedule of Notes and Accounts Receivable, Net (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2020	Mar. 31, 2019	Dec. 31, 2019
Accounts, Notes, Loans and Financing Receivable [Line Items]
Accounts and premiums receivable, net	$ 71,360		$ 50,712
Retrospective commissions receivable	118,518		105,387
Trust receivables	49,626		63,925
Other Receivables	27,889		24,752
Total	322,793		286,968
Bad debt expense	60	$ 80
Accounts and premiums receivable
Accounts, Notes, Loans and Financing Receivable [Line Items]
Accounts Receivable, Allowance for Credit Loss	150		109
Bad debt expense	8	11
Tiptree Insurance | Notes Receivable
Accounts, Notes, Loans and Financing Receivable [Line Items]
Notes receivable, net - premium financing program (1)	55,400		42,192
Accounts Receivable, Allowance for Credit Loss	101		95
Bad debt expense	49	$ 69
Financing Receivables, Equal to Greater than 90 Days Past Due | Tiptree Insurance | Notes Receivable
Accounts, Notes, Loans and Financing Receivable [Line Items]
Financing Receivable, 90 Days or More Past Due, Still Accruing	$ 200		$ 93