Segment Information - Information by Reportable Operating Segment (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2023	Jun. 30, 2022	Jun. 30, 2023	Jun. 30, 2022
Segment Reporting Information [Line Items]
Gross written premiums	$ 44,674	$ 37,418	$ 80,888	$ 70,382
Net written premiums	29,328	27,266	47,670	45,287
Net earned premiums	23,183	24,576	45,135	48,531
Other income	398	663	1,024	1,361
Segment revenue	23,581	25,239	46,159	49,892
Losses and LAE, net	19,319	22,251	33,032	40,269
Policy acquisition costs	4,413	5,725	9,134	11,189
Operating expenses	5,114	4,470	9,393	8,630
Segment expenses	28,846	32,446	51,559	60,088
Segment gain (loss)	(5,265)	(7,207)	(5,400)	(10,196)
Net investment income	1,354	564	2,661	1,071
Net realized investment gains (losses)	0	(1,436)	0	(1,505)
Change in fair value of equity securities	(12)	317	682	597
Other gains (losses)	0	(1)	0	(6)
Interest expense	(820)	(727)	(1,506)	(1,438)
Income (loss) before equity earnings in Affiliate and income taxes	(4,743)	(8,490)	(3,563)	(11,477)
Operating Segments | Commercial Lines
Segment Reporting Information [Line Items]
Gross written premiums	34,761	32,076	63,736	60,662
Net written premiums	20,485	22,386	32,726	36,726
Net earned premiums	17,487	20,784	34,610	41,308
Other income	56	67	108	138
Segment revenue	17,543	20,851	34,718	41,446
Losses and LAE, net	13,597	19,906	24,144	36,516
Policy acquisition costs	2,966	4,410	6,162	8,767
Operating expenses	3,600	3,508	6,628	6,669
Segment expenses	20,163	27,824	36,934	51,952
Segment gain (loss)	(2,620)	(6,973)	(2,216)	(10,506)
Income (loss) before equity earnings in Affiliate and income taxes	(2,620)	(6,973)	(2,216)	(10,506)
Operating Segments | Personal Lines
Segment Reporting Information [Line Items]
Gross written premiums	9,913	5,342	17,152	9,720
Net written premiums	8,843	4,880	14,944	8,561
Net earned premiums	5,696	3,792	10,525	7,223
Other income	23	26	46	32
Segment revenue	5,719	3,818	10,571	7,255
Losses and LAE, net	5,722	2,345	8,888	3,753
Policy acquisition costs	1,453	1,223	2,842	2,316
Operating expenses	792	484	1,384	886
Segment expenses	7,967	4,052	13,114	6,955
Segment gain (loss)	(2,248)	(234)	(2,543)	300
Income (loss) before equity earnings in Affiliate and income taxes	(2,248)	(234)	(2,543)	300
Operating Segments | Total Underwriting
Segment Reporting Information [Line Items]
Gross written premiums	44,674	37,418	80,888	70,382
Net written premiums	29,328	27,266	47,670	45,287
Net earned premiums	23,183	24,576	45,135	48,531
Other income	79	93	154	170
Segment revenue	23,262	24,669	45,289	48,701
Losses and LAE, net	19,319	22,251	33,032	40,269
Policy acquisition costs	4,419	5,633	9,004	11,083
Operating expenses	4,392	3,992	8,012	7,555
Segment expenses	28,130	31,876	50,048	58,907
Segment gain (loss)	(4,868)	(7,207)	(4,759)	(10,206)
Income (loss) before equity earnings in Affiliate and income taxes	(4,868)	(7,207)	(4,759)	(10,206)
Operating Segments | Wholesale Agency
Segment Reporting Information [Line Items]
Other income	594	1,064	1,473	2,176
Segment revenue	594	1,064	1,473	2,176
Policy acquisition costs	349	770	897	1,528
Operating expenses	365	274	717	566
Segment expenses	714	1,044	1,614	2,094
Segment gain (loss)	(120)	20	(141)	82
Income (loss) before equity earnings in Affiliate and income taxes	(120)	20	(141)	82
Corporate
Segment Reporting Information [Line Items]
Other income	74	147	146	294
Segment revenue	74	147	146	294
Operating expenses	357	204	664	509
Segment expenses	357	204	664	509
Segment gain (loss)	(283)	(57)	(518)	(215)
Net investment income	1,354	564	2,661	1,071
Net realized investment gains (losses)		(1,436)	0	(1,505)
Change in fair value of equity securities	(12)	317	682	597
Other gains (losses)		(1)		(6)
Interest expense	(820)	(727)	(1,506)	(1,438)
Income (loss) before equity earnings in Affiliate and income taxes	239	(1,340)	1,319	(1,496)
Eliminations
Segment Reporting Information [Line Items]
Other income	(349)	(641)	(749)	(1,279)
Segment revenue	(349)	(641)	(749)	(1,279)
Policy acquisition costs	(355)	(678)	(767)	(1,422)
Segment expenses	(355)	(678)	(767)	(1,422)
Segment gain (loss)	6	37	18	143
Income (loss) before equity earnings in Affiliate and income taxes	$ 6	$ 37	$ 18	$ 143