Segment Information - Information by Reportable Operating Segment (Details) - USD ($) $ in Thousands	3 Months Ended		9 Months Ended
	Sep. 30, 2022	Sep. 30, 2021	Sep. 30, 2022	Sep. 30, 2021
Segment Reporting Information [Line Items]
Gross written premiums	$ 33,088	$ 33,704	$ 103,470	$ 99,058
Net written premiums	23,693	26,069	68,980	79,084
Net earned premiums	24,958	24,941	73,489	72,614
Other income	603	752	1,964	1,974
Segment revenue	25,561	25,693	75,453	74,588
Losses and loss adjustment expenses, net	16,671	16,159	56,940	53,447
Policy acquisition costs	6,230	7,173	17,419	20,819
Operating expenses	4,380	4,077	13,010	12,768
Segment expenses	27,281	27,409	87,369	87,034
Segment gain (loss)	(1,720)	(1,716)	(11,916)	(12,446)
Net investment income	860	514	1,931	1,549
Net realized investment gains (losses)		(101)	(1,505)	3,883
Change in fair value of equity securities	(151)	(2,169)	446	(3,234)
Other gains (losses)	66	2,778	60	11,688
Interest expense	(778)	(701)	(2,216)	(2,154)
Income (loss) before equity earnings in Affiliate and income taxes	(1,723)	(1,395)	(13,200)	(714)
Operating Segments | Commercial Lines1
Segment Reporting Information [Line Items]
Gross written premiums	27,635	29,849	88,297	88,017
Net written premiums	18,730	22,456	55,456	68,685
Net earned premiums	20,789	21,975	62,097	64,869
Other income	57	50	195	158
Segment revenue	20,846	22,025	62,292	65,027
Losses and loss adjustment expenses, net	13,348	14,697	49,864	48,592
Policy acquisition costs	4,950	6,458	13,717	19,102
Operating expenses	3,297	2,954	9,966	8,761
Segment expenses	21,595	24,109	73,547	76,455
Segment gain (loss)	(749)	(2,084)	(11,255)	(11,428)
Income (loss) before equity earnings in Affiliate and income taxes	(749)	(2,084)	(11,255)	(11,428)
Operating Segments | Personal Lines
Segment Reporting Information [Line Items]
Gross written premiums	5,453	3,855	15,173	11,041
Net written premiums	4,963	3,613	13,524	10,399
Net earned premiums	4,169	2,966	11,392	7,745
Other income	26	29	58	113
Segment revenue	4,195	2,995	11,450	7,858
Losses and loss adjustment expenses, net	3,323	1,462	7,076	4,855
Policy acquisition costs	1,214	838	3,530	2,178
Operating expenses	519	336	1,405	1,076
Segment expenses	5,056	2,636	12,011	8,109
Segment gain (loss)	(861)	359	(561)	(251)
Income (loss) before equity earnings in Affiliate and income taxes	(861)	359	(561)	(251)
Operating Segments | Total Underwriting
Segment Reporting Information [Line Items]
Gross written premiums	33,088	33,704	103,470	99,058
Net written premiums	23,693	26,069	68,980	79,084
Net earned premiums	24,958	24,941	73,489	72,614
Other income	83	79	253	271
Segment revenue	25,041	25,020	73,742	72,885
Losses and loss adjustment expenses, net	16,671	16,159	56,940	53,447
Policy acquisition costs	6,164	7,296	17,247	21,280
Operating expenses	3,816	3,290	11,371	9,837
Segment expenses	26,651	26,745	85,558	84,564
Segment gain (loss)	(1,610)	(1,725)	(11,816)	(11,679)
Income (loss) before equity earnings in Affiliate and income taxes	(1,610)	(1,725)	(11,816)	(11,679)
Operating Segments | Wholesale Agency
Segment Reporting Information [Line Items]
Other income	793	1,235	2,969	4,932
Segment revenue	793	1,235	2,969	4,932
Policy acquisition costs	498	778	2,026	3,147
Operating expenses	245	500	811	2,060
Segment expenses	743	1,278	2,837	5,207
Segment gain (loss)	50	(43)	132	(275)
Income (loss) before equity earnings in Affiliate and income taxes	50	(43)	132	(275)
Corporate
Segment Reporting Information [Line Items]
Other income	113	148	407	219
Segment revenue	113	148	407	219
Operating expenses	319	287	828	871
Segment expenses	319	287	828	871
Segment gain (loss)	(206)	(139)	(421)	(652)
Net investment income	860	514	1,931	1,549
Net realized investment gains (losses)		(101)	(1,505)	3,883
Change in fair value of equity securities	(151)	(2,169)	446	(3,234)
Other gains (losses)	66	2,778	60	11,688
Interest expense	(778)	(701)	(2,216)	(2,154)
Income (loss) before equity earnings in Affiliate and income taxes	(209)	182	(1,705)	11,080
Eliminations
Segment Reporting Information [Line Items]
Other income	(386)	(710)	(1,665)	(3,448)
Segment revenue	(386)	(710)	(1,665)	(3,448)
Policy acquisition costs	(432)	(901)	(1,854)	(3,608)
Segment expenses	(432)	(901)	(1,854)	(3,608)
Segment gain (loss)	46	191	189	160
Income (loss) before equity earnings in Affiliate and income taxes	$ 46	$ 191	$ 189	$ 160