Segment Information - Information by Reportable Operating Segment (Details) - USD ($) $ in Thousands	3 Months Ended
	Mar. 31, 2021	Mar. 31, 2020
Segment Reporting Information [Line Items]
Gross written premiums	$ 30,373	$ 25,084
Net written premiums	24,483	21,051
Net earned premiums	22,835	22,017
Other income	556	658
Segment revenue	23,391	22,675
Losses and loss adjustment expenses, net	19,362	14,269
Policy acquisition costs	6,750	6,303
Operating expenses	4,349	5,045
Segment expenses	30,461	25,617
Segment gain (loss)	(7,070)	(2,942)
Net investment income	532	954
Net realized investment gains	2,924	928
Change in fair value of equity securities	(540)	(3,086)
Other gains		115
Interest expense	(721)	(731)
Income (loss) before equity earnings in Affiliate and income taxes	(4,875)	(4,762)
Operating Segments | Commercial Lines
Segment Reporting Information [Line Items]
Gross written premiums	27,221	23,444
Net written premiums	21,557	19,687
Net earned premiums	20,706	20,431
Other income	56	74
Segment revenue	20,762	20,505
Losses and loss adjustment expenses, net	16,955	13,461
Policy acquisition costs	6,318	6,164
Operating expenses	2,955	3,503
Segment expenses	26,228	23,128
Segment gain (loss)	(5,466)	(2,623)
Income (loss) before equity earnings in Affiliate and income taxes	(5,466)	(2,623)
Operating Segments | Personal Lines
Segment Reporting Information [Line Items]
Gross written premiums	3,152	1,640
Net written premiums	2,926	1,364
Net earned premiums	2,129	1,586
Other income	40	36
Segment revenue	2,169	1,622
Losses and loss adjustment expenses, net	2,407	808
Policy acquisition costs	600	489
Operating expenses	349	275
Segment expenses	3,356	1,572
Segment gain (loss)	(1,187)	50
Income (loss) before equity earnings in Affiliate and income taxes	(1,187)	50
Operating Segments | Total Underwriting
Segment Reporting Information [Line Items]
Gross written premiums	30,373	25,084
Net written premiums	24,483	21,051
Net earned premiums	22,835	22,017
Other income	96	110
Segment revenue	22,931	22,127
Losses and loss adjustment expenses, net	19,362	14,269
Policy acquisition costs	6,918	6,653
Operating expenses	3,304	3,778
Segment expenses	29,584	24,700
Segment gain (loss)	(6,653)	(2,573)
Income (loss) before equity earnings in Affiliate and income taxes	(6,653)	(2,573)
Operating Segments | Wholesale Agency
Segment Reporting Information [Line Items]
Other income	1,726	1,934
Segment revenue	1,726	1,934
Policy acquisition costs	1,127	1,208
Operating expenses	744	905
Segment expenses	1,871	2,113
Segment gain (loss)	(145)	(179)
Income (loss) before equity earnings in Affiliate and income taxes	(145)	(179)
Corporate
Segment Reporting Information [Line Items]
Other income	43	31
Segment revenue	43	31
Operating expenses	301	362
Segment expenses	301	362
Segment gain (loss)	(258)	(331)
Net investment income	532	954
Net realized investment gains	2,924	928
Change in fair value of equity securities	(540)	(3,086)
Other gains		115
Interest expense	(721)	(731)
Income (loss) before equity earnings in Affiliate and income taxes	1,937	(2,151)
Eliminations
Segment Reporting Information [Line Items]
Other income	(1,309)	(1,417)
Segment revenue	(1,309)	(1,417)
Policy acquisition costs	(1,295)	(1,558)
Segment expenses	(1,295)	(1,558)
Segment gain (loss)	(14)	141
Income (loss) before equity earnings in Affiliate and income taxes	$ (14)	$ 141