Segment Information - Information by Reportable Segment (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020	Dec. 31, 2019
Segment Reporting Information [Line Items]
Gross written premiums	$ 138,019	$ 132,095	$ 111,335
Net written premiums	91,232	101,429	92,940
Net earned premiums	96,711	98,802	89,103
Other income	2,768	2,671	2,615
Segment revenue	99,479	101,473	91,718
Loss and loss adjustment expenses, net	81,440	69,861	56,228
Policy acquisition costs	22,179	28,451	26,105
Operating expenses	18,789	16,509	18,468
Loss portfolio transfer risk fee	5,400	0	0
Segment expenses	127,808	114,821	100,801
Segment underwriting gain (loss)	(28,329)	(13,348)	(9,083)
Net investment income	3,043	1,968	3,156
Net realized investment gains (losses)	(1,505)	2,878	8,126
Change in fair value of equity securities	403	(2,020)	228
Gain from VSRM Transaction	8,810	0	0
Other gains (losses)	59	11,664	260
Interest expense	(2,971)	(2,852)	(2,925)
Income (loss) before income taxes	(20,490)	(1,710)	(238)
Deferred policy acquisition costs	10,290	12,267	12,243	$ 11,906
Unearned premiums	67,887	65,269	56,224
Unpaid losses and loss adjustment expenses	165,539	139,085	111,270	$ 107,246
Operating Segments | Commercial Lines
Segment Reporting Information [Line Items]
Gross written premiums	116,868	117,075	102,763
Net written premiums	72,318	87,307	85,385
Net earned premiums	80,823	87,759	82,409
Other income	245	215	242
Segment revenue	81,068	87,974	82,651
Loss and loss adjustment expenses, net	70,762	63,868	53,263
Policy acquisition costs	17,682	25,687	25,051
Operating expenses	13,069	11,648	12,644
Loss portfolio transfer risk fee	5,400
Segment expenses	106,913	101,203	90,958
Segment underwriting gain (loss)	(25,845)	(13,229)	(8,307)
Income (loss) before income taxes	(25,845)	(13,229)	(8,307)
Deferred policy acquisition costs	7,683	10,619	11,858
Unearned premiums	56,565	57,491	51,535
Unpaid losses and loss adjustment expenses	159,558	135,084	106,662
Operating Segments | Personal Lines
Segment Reporting Information [Line Items]
Gross written premiums	21,151	15,020	8,572
Net written premiums	18,914	14,122	7,555
Net earned premiums	15,888	11,043	6,694
Other income	82	143	150
Segment revenue	15,970	11,186	6,844
Loss and loss adjustment expenses, net	10,678	5,993	2,965
Policy acquisition costs	4,604	3,307	2,044
Operating expenses	1,936	1,357	1,069
Segment expenses	17,218	10,657	6,078
Segment underwriting gain (loss)	(1,248)	529	766
Income (loss) before income taxes	(1,248)	529	766
Deferred policy acquisition costs	2,796	2,075	1,183
Unearned premiums	11,322	7,778	4,689
Unpaid losses and loss adjustment expenses	5,981	4,001	4,608
Operating Segments | Underwriting
Segment Reporting Information [Line Items]
Gross written premiums	138,019	132,095	111,335
Net written premiums	91,232	101,429	92,940
Net earned premiums	96,711	98,802	89,103
Other income	327	358	392
Segment revenue	97,038	99,160	89,495
Loss and loss adjustment expenses, net	81,440	69,861	56,228
Policy acquisition costs	22,286	28,994	27,095
Operating expenses	15,005	13,005	13,713
Segment expenses	118,731	111,860	97,036
Segment underwriting gain (loss)	(21,693)	(12,700)	(7,541)
Income (loss) before income taxes	(21,693)	(12,700)	(7,541)
Operating Segments | Wholesale Agency
Segment Reporting Information [Line Items]
Other income	5,712	5,848	7,571
Segment revenue	5,712	5,848	7,571
Policy acquisition costs	3,653	3,727	4,938
Operating expenses	2,612	2,382	3,107
Segment expenses	6,265	6,109	8,045
Segment underwriting gain (loss)	(553)	(261)	(474)
Net investment income	32
Other gains (losses)	(1)
Interest expense	(42)
Income (loss) before income taxes	(564)	(261)	(474)
Corp-orate
Segment Reporting Information [Line Items]
Other income	271	365	245
Segment revenue	271	365	245
Operating expenses	1,192	1,122	1,648
Segment expenses	1,192	1,122	1,648
Segment underwriting gain (loss)	(921)	(757)	(1,403)
Net investment income	3,011	1,968	3,156
Net realized investment gains (losses)	(1,505)	2,878	8,126
Change in fair value of equity securities	403	(2,020)	228
Gain from VSRM Transaction	8,810
Other gains (losses)	60	11,664	260
Interest expense	(2,929)	(2,852)	(2,925)
Income (loss) before income taxes	6,929	10,881	7,442
Eliminations
Segment Reporting Information [Line Items]
Other income	(3,542)	(3,900)	(5,593)
Segment revenue	(3,542)	(3,900)	(5,593)
Policy acquisition costs	(3,760)	(4,270)	(5,928)
Operating expenses	(20)
Segment expenses	(3,780)	(4,270)	(5,928)
Segment underwriting gain (loss)	238	370	335
Income (loss) before income taxes	238	370	335
Deferred policy acquisition costs	$ (189)	$ (427)	$ (798)