Segment Information - Information by Reportable Operating Segment (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2021	Jun. 30, 2020	Jun. 30, 2021	Jun. 30, 2020
Segment Reporting Information [Line Items]
Gross written premiums	$ 34,981	$ 27,545	$ 65,354	$ 52,629
Net written premiums	28,532	23,065	53,015	44,116
Net earned premiums	24,838	21,758	47,673	43,775
Other income	666	713	1,222	1,371
Segment revenue	25,504	22,471	48,895	45,146
Losses and loss adjustment expenses, net	17,926	11,945	37,288	26,214
Policy acquisition costs	6,896	6,395	13,646	12,698
Operating expenses	4,342	4,859	8,691	9,904
Segment expenses	29,164	23,199	59,625	48,816
Segment gain (loss)	(3,660)	(728)	(10,730)	(3,670)
Net investment income	503	863	1,035	1,817
Net realized investment gains	1,060	245	3,984	1,173
Change in fair value of equity securities	(525)	1,576	(1,065)	(1,510)
Other gains	8,910	145	8,910	260
Interest expense	(732)	(731)	(1,453)	(1,462)
Income (loss) before equity earnings in Affiliate and income taxes	5,556	1,370	681	(3,392)
Operating Segments | Commercial Lines1
Segment Reporting Information [Line Items]
Gross written premiums	30,947	25,600	58,168	49,044
Net written premiums	24,672	21,377	46,229	41,064
Net earned premiums	22,188	20,105	42,894	40,536
Other income	52	82	108	156
Segment revenue	22,240	20,187	43,002	40,692
Losses and loss adjustment expenses, net	16,940	11,275	33,895	24,736
Policy acquisition costs	6,326	6,119	12,644	12,283
Operating expenses	2,852	3,145	5,807	6,648
Segment expenses	26,118	20,539	52,346	43,667
Segment gain (loss)	(3,878)	(352)	(9,344)	(2,975)
Income (loss) before equity earnings in Affiliate and income taxes	(3,878)	(352)	(9,344)	(2,975)
Operating Segments | Personal Lines
Segment Reporting Information [Line Items]
Gross written premiums	4,034	1,945	7,186	3,585
Net written premiums	3,860	1,688	6,786	3,052
Net earned premiums	2,650	1,653	4,779	3,239
Other income	44	36	84	72
Segment revenue	2,694	1,689	4,863	3,311
Losses and loss adjustment expenses, net	986	670	3,393	1,478
Policy acquisition costs	740	506	1,340	995
Operating expenses	391	272	740	547
Segment expenses	2,117	1,448	5,473	3,020
Segment gain (loss)	577	241	(610)	291
Income (loss) before equity earnings in Affiliate and income taxes	577	241	(610)	291
Operating Segments | Total Underwriting
Segment Reporting Information [Line Items]
Gross written premiums	34,981	27,545	65,354	52,629
Net written premiums	28,532	23,065	53,015	44,116
Net earned premiums	24,838	21,758	47,673	43,775
Other income	96	118	192	228
Segment revenue	24,934	21,876	47,865	44,003
Losses and loss adjustment expenses, net	17,926	11,945	37,288	26,214
Policy acquisition costs	7,066	6,625	13,984	13,278
Operating expenses	3,243	3,417	6,547	7,195
Segment expenses	28,235	21,987	57,819	46,687
Segment gain (loss)	(3,301)	(111)	(9,954)	(2,684)
Income (loss) before equity earnings in Affiliate and income taxes	(3,301)	(111)	(9,954)	(2,684)
Operating Segments | Wholesale Agency
Segment Reporting Information [Line Items]
Other income	1,971	2,081	3,697	4,015
Segment revenue	1,971	2,081	3,697	4,015
Policy acquisition costs	1,242	1,448	2,369	2,656
Operating expenses	816	736	1,560	1,641
Segment expenses	2,058	2,184	3,929	4,297
Segment gain (loss)	(87)	(103)	(232)	(282)
Income (loss) before equity earnings in Affiliate and income taxes	(87)	(103)	(232)	(282)
Corporate
Segment Reporting Information [Line Items]
Other income	28	132	71	163
Segment revenue	28	132	71	163
Operating expenses	283	706	584	1,068
Segment expenses	283	706	584	1,068
Segment gain (loss)	(255)	(574)	(513)	(905)
Net investment income	503	863	1,035	1,817
Net realized investment gains	1,060	245	3,984	1,173
Change in fair value of equity securities	(525)	1,576	(1,065)	(1,510)
Other gains	8,910	145	8,910	260
Interest expense	(732)	(731)	(1,453)	(1,462)
Income (loss) before equity earnings in Affiliate and income taxes	8,961	1,524	10,898	(627)
Eliminations
Segment Reporting Information [Line Items]
Other income	(1,429)	(1,618)	(2,738)	(3,035)
Segment revenue	(1,429)	(1,618)	(2,738)	(3,035)
Policy acquisition costs	(1,412)	(1,678)	(2,707)	(3,236)
Segment expenses	(1,412)	(1,678)	(2,707)	(3,236)
Segment gain (loss)	(17)	60	(31)	201
Income (loss) before equity earnings in Affiliate and income taxes	$ (17)	$ 60	$ (31)	$ 201