Conifer (CNFR) 10-K 27 Mar 23 2022 FY Annual report Financial data

Document and Entity Information

Document and Entity Information - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Mar. 27, 2023	Jun. 30, 2022
Cover [Abstract]
Document Type	10-K
Amendment Flag	false
Document Period End Date	Dec. 31, 2022
Document Fiscal Year Focus	2022
Document Fiscal Period Focus	FY
Entity Registrant Name	Conifer Holdings, Inc.
Entity Central Index Key	0001502292
Entity Current Reporting Status	Yes
Entity Voluntary Filers	No
Entity Interactive Data Current	Yes
Current Fiscal Year End Date	--12-31
Entity Filer Category	Non-accelerated Filer
Entity Well-known Seasoned Issuer	No
Entity Public Float				$ 5.3
Entity Common Stock, Shares Outstanding			12,215,849
Entity Shell Company	false
Entity Small Business	true
Entity Emerging Growth Company	false
Title of 12(b) Security	Common Stock, no par value
Trading Symbol	CNFR
Security Exchange Name	NASDAQ
Entity File Number	001-37536
Entity Incorporation, State or Country Code	MI
Entity Tax Identification Number	27-1298795
Entity Address, Address Line One	3001 West Big Beaver Road
Entity Address, Address Line Two	Suite 200
Entity Address, City or Town	Troy
Entity Address, State or Province	MI
Entity Address, Postal Zip Code	48084
City Area Code	248
Local Phone Number	559-0840
Document Annual Report	true
Document Transition Report	false
Auditor Firm ID	166	34
Auditor Name	Plante & Moran, PLLC	DELOITTE & TOUCHE LLP
Auditor Location	Chicago, Illinois	Detroit, Michigan

Consolidated Balance Sheets

Consolidated Balance Sheets - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Investment securities:
Debt securities, at fair value (amortized cost of $127,119 and $150,732, respectively)	$ 110,201	$ 149,783
Equity securities, at fair value (cost of $1,905 and $10,972, respectively)	1,267	9,931
Short-term investments, at fair value	25,929	23,013
Total investments	137,397	182,727
Cash and cash equivalents	28,035	9,913
Premiums and agents' balances receivable, net	21,802	21,197
Receivable from Affiliate	1,261	5,784
Reinsurance recoverables on unpaid losses	82,651	40,344
Reinsurance recoverables on paid losses	6,653	1,347
Prepaid reinsurance premiums	16,399	8,301
Deferred policy acquisition costs	10,290	12,267
Other assets	7,862	8,524
Total assets	312,350	290,404
Liabilities:
Unpaid losses and loss adjustment expenses	165,539	139,085
Unearned premiums	67,887	65,269
Reinsurance premium payable	6,144	5,318
Debt	33,876	33,564
Accounts payable and accrued expenses	19,954	6,665
Total liabilities	293,400	249,901
Commitments and contingencies	0	0
Shareholders' equity:
Common stock, no par value (100,000,000 shares authorized; 12,215,849 and 9,681,728 issued and outstanding, respectively)	97,913	92,692
Accumulated deficit	(60,760)	(50,079)
Accumulated other comprehensive income (loss)	(18,203)	(2,110)
Total shareholders' equity	18,950	40,503
Total liabilities and shareholders' equity	$ 312,350	$ 290,404

Consolidated Balance Sheets (Pa

Consolidated Balance Sheets (Parenthetical) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Statement of Financial Position [Abstract]
Debt securities, amortized cost	$ 127,119	$ 150,732
Equity securities, amortized cost	$ 1,905	$ 10,972
Common stock, par value (in dollars per share)	$ 0	$ 0
Common stock, shares authorized (in shares)	100,000,000	100,000,000
Common stock, shares issued (in shares)	12,215,849	9,707,817
Common stock, shares outstanding (in shares)	12,215,849	9,707,817

Consolidated Statements of Oper

Consolidated Statements of Operations - USD ($) $ in Thousands		12 Months Ended
		Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Revenue and Other Income
Gross earned premiums		$ 135,401	$ 123,050	$ 106,614
Ceded earned premiums		(38,690)	(24,248)	(17,511)
Net earned premiums		96,711	98,802	89,103
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
Loss portfolio transfer risk fee		(5,400)	0	0
Other gains (losses)		59	11,664	260
Other income		2,768	2,671	2,615
Total revenue and other income		104,889	115,963	103,488
Expenses
Losses 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
Interest expense		2,971	2,852	2,925
Total expenses		125,379	117,673	103,726
Income (loss) before income taxes		(20,490)	(1,710)	(238)
Equity earnings in Affiliate, net of tax		368	824	839
Income tax expense (benefit)		(9,441)	208	6
Net income (loss)		$ (10,681)	$ (1,094)	$ 595
Net income (loss) per share, basic		$ (1)	$ (0.11)	$ 0.06
Net income (loss) per share, diluted		$ (1)	$ (0.11)	$ 0.06
Weighted average common shares outstanding, basic	[1]	10,692,090	9,691,998	9,625,059
Weighted average common shares outstanding, diluted	[1]	10,692,090	9,691,998	9,625,059
[1] The non-vested shares of the restricted stock units and stock options were anti-dilutive as of December 31, 2022, 2021, and 2020. Therefore, the non-vested shares are excluded from earnings (loss) per share for the years ended December 31, 2022, 2021, and 2020 .

Consolidated Statements of Comp

Consolidated Statements of Comprehensive Income (Loss) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Statement of Comprehensive Income [Abstract]
Net income (loss)	$ (10,681)	$ (1,094)	$ 595
Unrealized investment gains (losses):
Unrealized investment gains (losses) during the period	(16,024)	(2,937)	1,589
Income tax expense (benefit)	0	0	0
Unrealized investment gains (losses), net of tax	(16,024)	(2,937)	1,589
Less: reclassification adjustments to:
Net realized investment gains (losses) included in net income (loss)	69	85	1,166
Income tax expense (benefit)	0	0	0
Total reclassifications included in net income (loss), net of tax	69	85	1,166
Other comprehensive income (loss)	(16,093)	(3,022)	423
Total comprehensive income (loss)	$ (26,774)	$ (4,116)	$ 1,018

Consolidated Statement of Chang

Consolidated Statement of Changes in Shareholders' Equity - USD ($) $ in Thousands	Total	No Par, Common Stock	Retained Earnings (Accumulated deficit)	Accumulated Other Comprehensive Income (Loss)
Balance at beginning of period at Dec. 31, 2019	$ 42,725	$ 91,816	$ (49,580)	$ 489
Balance at beginning of period (in shares) at Dec. 31, 2019		9,592,861
Net income (loss)	595		595
Repurchase of common stock	(36)	$ (36)
Repurchase of common stock (in shares)		(11,586)
Stock-based compensation expense	706	$ 706
Stock-based compensation expense, Shares		100,453
Other comprehensive income (loss)	423			423
Balance at end of period at Dec. 31, 2020	44,413	$ 92,486	(48,985)	912
Balance at end of period (in shares) at Dec. 31, 2020		9,681,728
Net income (loss)	(1,094)		(1,094)
Repurchase of common stock	(12)	$ (12)
Repurchase of common stock (in shares)		(3,886)
Stock-based compensation expense	218	$ 218
Stock-based compensation expense, Shares		29,975
Other comprehensive income (loss)	(3,022)			(3,022)
Balance at end of period at Dec. 31, 2021	40,503	$ 92,692	(50,079)	(2,110)
Balance at end of period (in shares) at Dec. 31, 2021		9,707,817
Net income (loss)	(10,681)		(10,681)
Repurchase of common stock	10	$ 10
Repurchase of common stock (in shares)		(1,968)
Issuance of common stock private placement	5,000	$ 5,000
Issuance of common stock private placement (in shares)		2,500,000
Stock-based compensation expense	211	$ 211
Stock-based compensation expense, Shares		10,000
Other comprehensive income (loss)	(16,093)			(16,093)
Balance at end of period at Dec. 31, 2022	$ 18,950	$ 97,913	$ (60,760)	$ (18,203)
Balance at end of period (in shares) at Dec. 31, 2022		12,215,849

Consolidated Statements of Cash

Consolidated Statements of Cash Flows (Unaudited) - USD ($) $ in Thousands		12 Months Ended
		Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Cash Flows from Operating Activities
Net income (loss)		$ (10,681)	$ (1,094)	$ 595
Adjustments to reconcile net income (loss) to net cash provided by (used in) operating activities:
Gain upon consolidation of VSRM and sale of agency business	[1]	(10,052)
Gain on sale of agency business			(8,910)
Depreciation and amortization		417	423	437
Amortization of bond premium and discount, net		320	523	655
Net realized investment (gains) losses		1,505	(2,878)	(8,126)
Change in fair value of equity securities		(403)	2,020	(228)
Loss on sale of fixed assets		33
Deferred income tax expense		(9,396)	0	0
Stock-based compensation expenses		211	218	706
Equity earnings in Affiliate, net of tax		(368)	(824)	(839)
PPP Loan forgiveness			(2,745)	0
Other		60	17	(262)
(Increase) decrease in:
Premiums, agents' balances and other receivables		(594)	(811)	311
Reinsurance recoverables		(47,613)	(15,335)	1,378
Prepaid reinsurance premiums		(8,098)	(6,985)	(66)
Deferred policy acquisition costs		1,977	(24)	(337)
Other assets		(138)	949	908
Increase (decrease) in:
Unpaid losses and loss adjustment expenses		26,454	27,815	4,024
Unearned premiums		2,618	9,045	4,721
Reinsurance premiums payable		11,926	5,318
Accounts payable and other liabilities		1,348	(1,367)	(895)
Net cash provided by operating activities		(40,474)	5,355	2,982
Cash Flows From Investing Activities
Purchases of investments		(318,227)	(226,794)	(391,588)
Proceeds from maturities and redemptions of investments		20,324	25,834	23,403
Proceeds from sales of investments		324,091	198,408	360,926
Proceeds from sale of agency business, net of $271 of cash disposed of	[1]	32,759	4,000
Purchase of VSRM, net of $3,920 cash acquired	[1]	(1,947)
Deconsolidation of SSU	[1]	(497)
Dividends from Affiliate			1,000
Other purchases			(1,071)	(78)
Net cash provided by (used in) investing activities		56,503	1,377	(7,337)
Cash Flows From Financing Activities
Proceeds received from issuance of shares of common stock		5,000
Repurchase of common stock		10	(12)	(36)
Borrowings under lines of credit		19,500	3,000	5,745
Repayment of lines of credit		(19,500)	(8,000)	(625)
Paydown of long-term debt		(2,917)
Net cash provided by (used in) financing activities		2,093	(5,012)	5,084
Net increase (decrease) in cash		18,122	1,720	729
Cash at beginning of period		9,913	8,193	7,464
Cash at end of period		28,035	9,913	8,193
Supplemental Disclosure of Cash Flow Information:
Interest paid		2,979	2,883	2,586
Income taxes paid (refunded), net		$ (11)	163	$ (82)
Increase in note receivable from sale of agency business			$ 6,000
[1] See Note 2 ~ VSRM Transaction

Consolidated Statements of Ca_2

Consolidated Statements of Cash Flows (Unaudited) (Parenthetical) $ in Thousands	12 Months Ended
	Dec. 31, 2022 USD ($)
Statement of Cash Flows [Abstract]
Cash used	$ 271
Cash acquired	$ 3,920

Summary of Significant Accounti

Summary of Significant Accounting Policies	12 Months Ended
	Dec. 31, 2022
Accounting Policies [Abstract]
Summary of Significant Accounting Policies	CONIFER HOLDINGS, INC. AND SUBSIDIARIES Notes to Consolidated Financial Statements 1. Summary of Significant Accounting Policies Recent Developments COVID-19 (the “Pandemic”) continues to cause significant disruption to public health, the global economy, financial markets, and commercial, social and community activity in general. As there has been a significant reduction in reported cases and correspondingly a reduction in government restrictions, we see reduced risk to our business. We continue to monitor potential risks the Pandemic may present including a potential resurgence. Our exposure to the Pandemic is manifold. The majority of our employees continue to work remotely however strict “shelter-in-place” or “stay-at-home” orders have been lifted. A significant portion of our revenues are generated from the hospitality sector within the U.S. which remains under stress due to the threats of resurgence and resource shortages that resulted from the Pandemic. We have continued to provide customer service, process new and renewal business, handle claims and otherwise manage all operations even though the vast majority of the staff is working remotely. To date, we have not seen a major disruption in our business as a result of the Pandemic and currently do not expect to see a material negative impact to our financial position or results of operations as a result of the Pandemic. Basis of Presentation and Management Representation The consolidated financial statements include accounts, after elimination of intercompany accounts and transactions, of Conifer Holdings, Inc. (the “Company” or “Conifer”), its wholly owned subsidiaries Conifer Insurance Company ("CIC"), Red Cedar Insurance Company ("RCIC"), White Pine Insurance Company ("WPIC"), Sycamore Insurance Agency, Inc. ("Sycamore"), and, as of October 13, 2022, VSRM, Inc. ("VSRM"). VSRM has substantially no operations following the contribution to SSU as described in Note 2 ~ VSRM Transaction . CIC, WPIC, and RCIC are collectively referred to as the "Insurance Company Subsidiaries." On a stand-alone basis Conifer Holdings, Inc. is referred to as the "Parent Company." The accompanying consolidated financial statements have been prepared in conformity with accounting principles generally accepted in the United States of America (“GAAP”), which differ from statutory accounting practices prescribed or permitted for insurance companies by regulatory authorities. Business The Company is engaged in the sale of property and casualty insurance products and has organized its principal operations into three types of insurance businesses: commercial lines, personal lines, and agency business. The Company underwrites a variety of specialty insurance products, including property, general liability, liquor liability, automobile, and homeowners and dwelling policies. The Company markets and sells its insurance products through a network of independent agents, including managing general agents, whereby policies are written in all 50 states in the United States (“U.S.”). The Company’s corporate headquarters are located in Troy, Michigan with additional office facilities in Florida and Michigan. Summary of Significant Accounting Policies Use of Estimates The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities at the date of the financial statements and the reported amounts of revenues and expenses during the reporting period. In applying these estimates, management makes subjective and complex judgments that frequently require assumptions about matters that are inherently uncertain, including uncertainties associated with the Pandemic. While management believes the amounts included in the consolidated financial statements reflect management's best estimates and assumptions, actual results may differ from these estimates. Cash, Cash Equivalents, and Short-term Investments Cash consists of cash deposits in banks, generally in operating accounts. Cash equivalents consist of money-market funds that are specifically used as overnight investments tied to cash deposit accounts. Short-term investments, consisting of money-market funds, are classified as short-term investments in the consolidated balance sheets as they relate to the Company’s investment activities. Lease Accounting The Company accounts for leases under FASB Accounting Standards Update ("ASU") No. 2016-02, Leases (Topic 842), which required the recognition of a right-of-use asset and a corresponding lease liability, discounted to the present value upon initial recognition, for all leases that extend beyond 12 months. For operating leases, the asset and liability are amortized over the lease term with expense recognized on a straight-line basis and all cash flows included in the operating section of the consolidated statement of cash flows. We do not have any financing leases. Our operating leases consist primarily of real estate utilized in the operation of our businesses with lease terms ranging from 5 to 10 years . Management has determined the appropriate discount rate to use in calculating the right-to-use asset and lease liability is 6.75 %. The Company records a right-of-use asset and lease liabilities included in Other Assets and Other Liabilities in the Consolidated Balance Sheets. As of December 31, 2022, the Company had a right-of-use asset of $ 1.3 million, and lease liabilities of $ 1.3 million. As of December 31, 2021, the Company had a right-of-use asset of $ 1.4 million, and lease liabilities of $ 1.5 million. Investment Securities Debt securities are classified as available-for-sale and reported at fair value. The Company determines the fair value using the market approach, which uses quoted prices or other relevant data based on market transactions involving identical or comparable assets. The Company purchases available-for-sale debt securities with the expectation that they will be held to maturity, however the Company may sell them if market conditions or credit‑related risk warrant earlier sales. The Company does not have any securities classified as held-to-maturity or trading. The change in unrealized gain and loss on debt securities is recorded as a component of accumulated other comprehensive income (loss), net of the related deferred tax effect, until realized. The debt securities portfolio includes structured securities. The Company recognizes income from these securities using a constant effective yield based on anticipated prepayments and the estimated economic life of the securities. When actual prepayments differ significantly from anticipated prepayments, the estimated economic life is recalculated and the remaining unamortized premium or discount is amortized prospectively over the remaining economic life. Premiums and discounts on structured securities are amortized or accreted over the life of the related available‑for‑sale security as an adjustment to yield using the effective interest method. Such amortization and accretion is included in interest income in the consolidated statements of operations. Dividend and interest income are recognized when earned. Realized gains and losses from the sale of available-for-sale securities are determined on a specific-identification basis and included in earnings on the trade date. Equity securities that do not result in consolidation and are not accounted for under the equity method are measured at fair value and any changes in fair value are recognized in net income in the Consolidated Statements of Operations. Investment company limited partnerships are measured at their net asset value, which approximates fair value. Any changes in the net asset value are recognized in net income in the Consolidated Statements of Operations. The Company carries other equity investments that do not have a readily determinable fair value at cost, less impairment and adjusted for observable price changes under the measurement alternative provided under GAAP. We review these investments for impairment during each reporting period. These investments are a component of Other Assets in the Consolidated Balance Sheets. Other-than-Temporary Impairments The Company reviews its impaired securities for possible other-than-temporary impairment ("OTTI") at each quarter-end. A security has an impairment loss when its fair value is less than its cost or amortized cost at the balance sheet date. The Company considers the following factors in performing its review: (i) the amount by which the security’s fair value is less than its cost, (ii) length of time the security has been impaired, (iii) whether management has the intent to sell the security, (iv) if it is more likely than not that management will be required to sell the security before recovery of its amortized cost basis, (v) whether the impairment is due to an issuer‑specific event, credit issues or change in market interest rates, (vi) the security’s credit rating and any recent downgrades or (vii) stress testing of expected cash flows under different scenarios. If the Company cannot conclude that declines in fair value below amortized cost are considered temporary, an OTTI loss is recorded through the Consolidated Statements of Operations in the current period. For all other impaired securities, the Company will assess whether the net present value of the cash flows expected to be collected from the security is less than its amortized cost basis. Such a shortfall in cash flows is referred to as a “credit loss.” For any such security, the Company separates the impairment loss into: (i) the credit loss and (ii) the non-credit loss, which is the amount related to all other factors such as interest rate changes, fluctuations in exchange rates and market conditions. The credit loss charge is recorded to the current period statements of operations and the non-credit loss is recorded to accumulated other comprehensive income (loss), within shareholders’ equity, on an after-tax basis. A security’s cost basis is permanently reduced by the amount of a credit loss. Income is accreted over the remaining life of a security based on the interest rate necessary to discount the expected future cash flows to the new basis. If the security is non-income producing, any cash proceeds are applied as a reduction of principal when received. Recognition of Premium Revenues All of the property and casualty policies written by our insurance companies are considered short-duration contracts. These policy premiums are earned on a daily pro-rata basis, net of reinsurance, over the term of the policy, which are primarily twelve months in duration. The portion of premiums written that relate to the unexpired terms of policies in force are deferred and reported as unearned premium at the balance sheet date. Reinsurance Reinsurance premiums, commissions, losses and loss adjustment expenses ("LAE") on reinsured business are accounted for on a basis consistent with that used in accounting for the original policies issued and the terms of the reinsurance contracts. The amounts reported as reinsurance recoverables include amounts billed to reinsurers on losses and LAE paid as well as estimates of amounts expected to be recovered from reinsurers on insurance liabilities that have not yet been paid. Reinsurance recoverables on unpaid losses and LAE are estimated based upon assumptions consistent with those used in establishing the gross liabilities as they are applied to the underlying reinsured contracts. The Company records an allowance for uncollectible reinsurance recoverables based on an assessment of the reinsurer’s creditworthiness and collectability of the recorded amounts. Management believes an allowance for uncollectible recoverables from its reinsurers was not necessary for the periods presented. The Company receives ceding commissions in connection with certain ceded reinsurance. The ceding commissions are recorded as a reduction of policy acquisition costs. In 2022, the Company entered into a loss portfolio transfer ("LPT") reinsurance agreement. The LPT is a retroactive reinsurance contract. See Note 8 ~ Reinsurance for further details regarding the LPT. Deferred Policy Acquisition Costs Costs incurred which are incremental and directly related to the successful acquisition of new or renewal insurance business is deferred. These deferred costs consist of commissions paid to agents (net of ceding commissions), premium taxes, and underwriting costs, including compensation and payroll related benefits. Proceeds from reinsurance transactions that represent recovery of acquisition costs reduce applicable unamortized acquisition costs in such a manner that net acquisition costs are capitalized and charged to expense. Amortization of such policy acquisition costs is charged to expense in proportion to premium earned over the estimated policy term. To the extent that unearned premiums on existing policies are not adequate to cover the sum of expected losses and LAE, unamortized acquisition costs and policy maintenance costs, unamortized deferred policy acquisition costs are charged to expense to the extent required to eliminate the premium deficiency. If the premium deficiency is greater than the unamortized policy acquisition costs, a liability is recorded for any such deficiency. As of December 31, 2022, there was no premium deficiency reserve. The Company considers anticipated investment income in determining whether a premium deficiency exists. Management performs this evaluation at each insurance product line level. Unpaid Losses and Loss Adjustment Expenses The liability for unpaid losses and LAE in the Consolidated Balance Sheets represents the Company’s estimate of the amount it expects to pay for the ultimate cost of all losses and LAE incurred that remain unpaid at the balance sheet date. The liability is recorded on an undiscounted basis, except for the liability for unpaid losses and LAE assumed related to any acquired companies which are initially recorded at fair value. The process of estimating the liability for unpaid losses and LAE is a complex process that requires a high degree of judgment. The liability for unpaid losses and LAE represents the accumulation of individual case estimates for reported losses and LAE, and actuarially determined estimates for incurred but not reported losses and LAE and includes a provision for estimated costs to settle all outstanding claims at the balance sheet date. The liability for unpaid losses and LAE is intended to include the ultimate net cost of all losses and LAE incurred but unpaid as of the balance sheet date. The liability is stated net of anticipated deductibles, salvage and subrogation, and gross of reinsurance ceded. The estimate of the unpaid losses and LAE liability is continually reviewed and updated. Although management believes the liability for losses and LAE is reasonable, the ultimate liability may be more or less than the current estimate. The estimation of ultimate liability for unpaid losses and LAE is a complex, imprecise and inherently uncertain process, and therefore involves a considerable degree of judgment and expertise. The Company utilizes various actuarially‑accepted reserving methodologies in deriving the continuum of expected outcomes and ultimately determining its estimated liability amount. These methodologies utilize various inputs, including but not limited to written and earned premiums, paid and reported losses and LAE, expected initial loss and LAE ratio, which is the ratio of incurred losses and LAE to earned premiums, and expected claim reporting and payout patterns (including company-specific and industry data). The liability for unpaid loss and LAE does not represent an exact measurement of liability, but is an estimate that is not directly or precisely quantifiable, particularly on a prospective basis, and is subject to a significant degree of variability over time. In addition, the establishment of the liability for unpaid losses and LAE makes no provision for the broadening of coverage by legislative action or judicial interpretation or for the extraordinary future emergence of new types of losses not sufficiently represented in the Company’s historical experience or which cannot yet be quantified. As a result, an integral component of estimating the liability for unpaid losses and LAE is the use of informed subjective estimates and judgments about the ultimate exposure to unpaid losses and LAE. The effects of changes in the estimated liability are included in the results of operations in the period in which the estimates are revised. The Company allocates the applicable portion of the unpaid losses and LAE to amounts recoverable from reinsurers under reinsurance contracts and reports those amounts separately as assets on the consolidated balance sheets. Income Taxes Income taxes are accounted for under the asset and liability method. Deferred tax assets and liabilities are recognized for the future tax consequences attributable to differences between the financial statement carrying amounts of existing assets and liabilities and their respective tax bases and operating loss and tax-credit carryforwards. Deferred tax assets and liabilities are measured using enacted tax rates expected to apply to taxable income in the years in which those temporary differences are expected to be recovered or settled. The effect on deferred tax assets and liabilities of a change in tax rates is recognized in income in the period that includes the enactment date. Deferred tax assets are recognized to the extent that there is sufficient positive evidence, as allowed under the Accounting Standard Codification ("ASC") 740, Income Taxes, to support the recoverability of those deferred tax assets. The Company establishes a valuation allowance to the extent that there is insufficient evidence to support the recoverability of the deferred tax asset under ASC 740. In making such a determination, management considers all available positive and negative evidence, including future reversals of existing taxable temporary differences, projected future taxable income, tax‑planning strategies, and results of recent operations. If it is determined that the deferred tax assets would be realizable in the future in excess of their net recorded amount, an adjustment would be made to the deferred tax asset valuation allowance, which would reduce the provision for income taxes. As of December 31, 2022 and 2021 , the Company did no t have any unrecognized tax benefits and had no accrued interest or penalties related to uncertain tax positions. Other Income Other income consists primarily of fees charged to policyholders by the Company for services outside of the premium charge, such as installment billings or policy issuance costs. Commission income is also received by the Company’s insurance agencies for writing policies for third party insurance companies. The Company recognizes commission income on the later of the effective date of the policy, the date when the premium can be reasonably established, or the date when substantially all services related to the insurance placement have been rendered. Operating Expenses Operating expenses consist primarily of other underwriting, compensation and benefits, information technology, facility and other administrative expenses. Accounting Guidance Not Yet Adopted In June 2016, the FASB issued ASU No. 2016-13, Financial Instruments - Credit Losses (Topic 326), which amends the current methodology and timing for recognizing credit losses. This amendment will replace the current GAAP "incurred loss" methodology for credit losses with a methodology based on expected credit losses. The new guidance will also require expanded consideration of a broader range of reasonable and increased supportable information for the credit loss estimates. This ASU is effective for annual and interim reporting periods beginning after December 15, 2022. Management does not expect the new guidance to have a material impact on the Company's consolidated financial statements. In January 2021, the FASB issued ASU 2022-06, Reference Rate Reform (Topic 848) . This guidance provides optional expedients and exceptions that are intended to ease the burden of updating contracts to contain a new reference rate due to the discontinuation of the London Inter-Bank Offered Rate (LIBOR). This guidance is available immediately and may be implemented in any period prior to the guidance expiration on December 31, 2024. Management does not expect the new guidance to have a material impact on the Company’s consolidated financial statements.

VSRM Transaction

VSRM Transaction	12 Months Ended
	Dec. 31, 2022
Business Combinations [Abstract]
VSRM Transaction	2. VSRM Transaction Prior to October 13, 2022, Sycamore owned 50 % of Venture Agency Holdings, Inc. ("Venture") and has accounted for its ownership under the equity method of accounting. On October 13, 2022, Sycamore purchased the other 50 % of Venture from an individual for $ 9.7 million. Following this purchase, Sycamore obtained control and owned 100 % of Venture, which was then renamed to VSRM, Inc. ("VSRM"). VRSM and its two wholly owned subsidiaries, The Roots Insurance Agency, Inc. ("Roots") and Mitzel Insurance Agency, Inc. ("Mitzel") were incorporated into the Company's consolidated financial statements as of the date of the acquisition. Sycamore initially purchased the Venture shares with a promissory note for $ 9.7 million and ultimately settled the note with $ 5.9 million of cash received from the Security & Alarm Business sale, described below, and $ 3.8 million in the form of stock from the buyer of the Security & Alarm Business. The Company acquired the remaining outstanding shares of VSRM, in order to take advantage of net operating tax losses as part of a tax planning strategy to apply to the Security and Alarm Business sale described below, in addition to the strategic focus of getting out of the Security and Alarm line of business. The Company recognized Sycamore's purchase of the individual's shares of VSRM as a step acquisition and revalued all assets and liabilities upon the acquisition date. This resulted in the recognition of an $ 8.8 million non-operating gain reported in the Consolidated Statement of Operations as Gain from VSRM Transaction in the fourth quarter of 2022. The Company also utilized $ 12.5 million of federal income tax net operating losses carried forward and $ 14.8 million state income tax net operating losses carried forward, for a total net-of-tax benefit of $ 9.4 million. VSRM retained $ 8.9 million of debt, and $ 9.4 million of tax liabilities, as well as other smaller assets and liabilities that did not go with the transaction. A condensed schedule of assets and liabilities incorporated into the consolidated balance sheet from the VSRM acquisition is provided below: Cash $ 3,921 Trade receivables 4,604 Customer relationship intangible assets 37,122 Other assets 574 Total assets $ 46,221 Trade and other payables 7,624 Deferred tax liability 9,407 Note payable to Affiliate 6,000 Senior debt 2,917 Total Liabilities $ 25,948 Fair value of net assets acquired $ 20,273 The following table presents the calculation of the $ 8.8 million revaluation gain related to the Company's equity method investment in VSRM as a result of the VSRM Transaction: Carrying value of equity method investment in VSRM $ 1,773 Fair value of investment in VSRM 10,583 Gain on step acquisition $ 8,810 The fair value of the equity interest of VSRM immediately prior to the acquisition was $ 10.6 million. The fair value techniques used to measure the fair value of VSRM included using the recent valuations performed by third party valuation experts and the net realized proceeds received upon the sale of the Security & Alarm Business sold the following day. There were no material transaction costs incurred in the acquisition of VSRM. Additionally, no results of operations for the Security and Alarm business have been included the consolidated financial statements as that business was immediately disposed of. Results of operations for the retained business have been included from the date of acquisition through December 31, 2022. On October 14, 2022, VSRM sold all of its security guard and alarm installation insurance brokerage business (the "Security & Alarm Business") to a third party insurance brokerage firm for $ 38.2 million, of which $ 32.8 million was paid in cash and $ 3.8 million was in the form of the buyer's stock. The $ 3.8 million of buyer's stock was immediately used to settle a portion of the $ 9.7 million promissory note that was issued to buy the 50 % of Venture and the remainder of the promissory note was settled with cash from the sale of business. As part of the transaction, the individual who previously owned 50 % of VSRM transitioned employment to the buyer, along with a team of approximately eight other employees of VSRM. Also, the Company transferred to the buyer, $ 4.3 million of accounts receivable, $ 5.8 million of current liabilities, $ 271,000 in cash as well as all books and records of the business being purchased. The buyer held back $ 75,000 of cash for a future true up of the trade balances which the Company reflected as a current receivable. The Company recognized this transaction as the sale of a business. Because all assets and liabilities were just adjusted to fair value from the step acquisition described above, the basis of the net assets sold equaled the net proceeds from the sale, thus there was no gain recognized upon the sale of the Security & Alarm Business. The following table reconciles the net assets disposed of from this transaction: Cash at closing $ 32,759 Net liabilities transferred 1,499 Hold back 75 Stock of acquirer 3,822 Total purchase price $ 38,155 Cash $ 271 Premiums transferred to buyer 4,326 Intangible assets 38,154 Trade payables and accrued liabilities assumed by buyer ( 5,838 ) Net assets disposed of 36,913 Net gain 1,242 Broker fee transaction costs ( 1,242 ) Net gain $ — The net gain on revaluation of the investment in VSRM and the disposal of the Security and Alarm Business line are summarized below: Gross gains $ 10,052 Broker fee ( 1,242 ) Net gain $ 8,810 On December 30, 2022, VSRM contributed its remaining business, including its two wholly owned subsidiaries (Mitzel and Roots) to a new wholly owned subsidiary, Sycamore Specialty Underwriters, LLC ("SSU"). The business contributed to SSU consisted of customer accounts of substantially all of the personal lines business and a small subset of the commercial lines business underwritten by the Insurance Company Subsidiaries, and all of the customer accounts VSRM produced for third-party insurers, other than the security guard and alarm installation brokerage business previously sold. On December 31, 2022, Sycamore Financial Group, LLC ("SFG"), wholly owned by Andrew D. Petcoff purchased 50 % of SSU from VSRM, Inc. for $ 1,000 . As a result, SSU and its two wholly owned subsidiaries, Roots and Mitzel, are no longer consolidated in the Company's consolidated financial statements as of December 31, 2022, and VSRM's investment in SSU is accounted for using the equity method. The net assets transferred to SSU had a fair value of $ 0 at the time of the contribution. There was no gain or loss recognized upon the sale of half of SSU to SFG. Included in the net assets transferred to SSU was a $ 1.0 million promissory note obligation of VSRM that originated as part of the Venture Transaction described below, and is payable to CIC. The following table provides the assets and liabilities deconsolidated as a result of this transaction: Cash $ 497 Receivable from VSRM 934 Trade receivables 239 Intangible asset 196 Other assets 514 Total assets $ 2,380 Payable to Affiliates 286 Trade payables 193 Note payable 1,000 Other liabilities 901 Total Liabilities $ 2,380 In order to determine the value of the business contributed to SSU, the Company obtained a third party valuation based on a weighting of discounted cash flows and earnings before interest, taxes, depreciation and amortization (EBITDA) multiple valuation methods. The valuation included significant estimates and assumptions related to (i) forecasted revenue and EBITDA and (ii) the selection of the EBITDA multiple and discount rate.

Sale of Certain Agency Business

Sale of Certain Agency Business	12 Months Ended
	Dec. 31, 2022
Disclosure Text Block [Abstract]
Sale of Certain Agency Business	3. Sale of Certain Agency Business On June 30, 2021, Sycamore Insurance Agency sold to Venture Agency Holdings, Inc. the customer accounts and other related assets of some of its personal and commercial lines of business, hereby referred to as the (“Venture Transaction”). The customer accounts consist substantially of new and renewal rights and customer lists of the agency. Sycamore will continue to produce various personal and commercial lines that it did not sell to Venture, which is substantially all produced for, and underwritten by, the Insurance Company Subsidiaries. The Company recognized an $ 8.9 million gain on the sale which is reflected in Other Gains on the Consolidated Statements of Operations. The purchase price was $ 10.0 million of which $ 1.0 million was paid in cash on June 30, 2021, and $ 9.0 million was in the form of two promissory notes (one for $ 6.0 million and one for $ 3.0 million). Both notes require interest-only quarterly payments at a per annum rate of 7.0 %, with a five-year maturity. There are no prepayment penalties. On December 14, 2021, Venture paid off the $ 3.0 million note. On October 20, 2022, Venture paid down $ 5.0 million of the $ 6.0 million note. The remaining $ 1.0 million promissory note was assumed by SSU as part of the contribution of business to SSU described in Note 2 ~ Acquisition of Joint Venture and Subsequent Sale of Business. The assets sold included the customer accounts of substantially all of the personal lines business and a small subset of the commercial lines business underwritten by the Insurance Company Subsidiaries, and all of the customer accounts Sycamore produced for third-party insurers. The transaction included the transition of 21 employees from Conifer to Venture as well as necessary systems and office functions to operate the business. Venture is not assuming any in-force business or liabilities.

Investments

Investments	12 Months Ended
	Dec. 31, 2022
Investments, Debt and Equity Securities [Abstract]
Investments	. Invest ments The cost or amortized cost, gross unrealized gain or loss, and estimated fair value of the investments in securities classified as available-for-sale at December 31, 2022 and 2021 were as follows (dollars in thousands): December 31, 2022 Cost or Gross Unrealized Amortized Gains Losses Estimated Debt securities: U.S. Government $ 7,833 $ — $ ( 335 ) $ 7,498 State and local government 25,487 1 ( 4,672 ) 20,816 Corporate debt 35,347 — ( 4,788 ) 30,559 Asset-backed securities 21,742 — ( 1,246 ) 20,496 Mortgage-backed securities 29,194 — ( 5,157 ) 24,037 Commercial mortgage-backed securities 3,414 — ( 186 ) 3,228 Collateralized mortgage obligations 4,102 — ( 535 ) 3,567 Total debt securities available for sale $ 127,119 $ 1 $ ( 16,919 ) $ 110,201 December 31, 2021 Cost or Gross Unrealized Amortized Gains Losses Estimated Debt securities: U.S. Government $ 20,723 $ 74 $ ( 77 ) $ 20,720 State and local government 30,063 555 ( 189 ) 30,429 Corporate debt 30,808 88 ( 550 ) 30,346 Asset-backed securities 28,652 10 ( 224 ) 28,438 Mortgage-backed securities 33,178 105 ( 762 ) 32,521 Commercial mortgage-backed securities 1,659 31 — 1,690 Collateralized mortgage obligations 5,649 35 ( 45 ) 5,639 Total debt securities available for sale $ 150,732 $ 898 $ ( 1,847 ) $ 149,783 The following table summarizes the aggregate fair value and gross unrealized losses, by security type, of the available-for-sale securities in unrealized loss positions. The table segregates the holdings based on the length of time that individual securities have been in a continuous unrealized loss position (dollars in thousands): December 31, 2022 Less than 12 months 12 months or More Total No. Fair Value of Gross No. Fair Value of Gross No. Fair Value of Gross Debt securities: U.S. Government 8 $ 3,534 $ ( 135 ) 5 $ 3,964 $ ( 200 ) 13 $ 7,498 $ ( 335 ) State and local government 77 12,966 ( 2,318 ) 45 7,147 ( 2,354 ) 122 20,113 ( 4,672 ) Corporate debt 27 10,069 ( 1,373 ) 42 20,890 ( 3,415 ) 69 30,959 ( 4,788 ) Asset-backed securities 6 3,188 ( 76 ) 20 17,308 ( 1,170 ) 26 20,496 ( 1,246 ) Mortgage-backed securities 57 4,006 ( 573 ) 12 20,031 ( 4,584 ) 69 24,037 ( 5,157 ) Commercial mortgage 4 3,205 ( 186 ) - - - 4 3,205 ( 186 ) Collateralized mortgage 26 1,789 ( 196 ) 9 1,802 ( 339 ) 35 3,591 ( 535 ) Total debt securities 205 38,757 ( 4,857 ) 133 71,142 ( 12,062 ) 338 109,899 ( 16,919 ) December 31, 2021 Less than 12 months 12 months or More Total No. Fair Value of Gross No. Fair Value of Gross No. Fair Value of Gross Debt securities: U.S. Government 6 $ 10,323 $ ( 47 ) 1 $ 4,728 $ ( 30 ) 7 $ 15,051 $ ( 77 ) State and local government 41 8,875 ( 172 ) 4 446 ( 17 ) 45 9,321 ( 189 ) Corporate debt 41 22,748 ( 505 ) 1 705 ( 45 ) 42 23,453 ( 550 ) Asset-backed securities 24 24,305 ( 219 ) 2 1,893 ( 5 ) 26 26,198 ( 224 ) Mortgage-backed securities 12 27,034 ( 762 ) — — — 12 27,034 ( 762 ) Commercial mortgage 0 — 0 — — — 0 — 0 Collateralized mortgage 10 2,638 ( 45 ) 2 29 — 12 2,667 ( 45 ) Total debt securities 134 $ 95,923 $ ( 1,750 ) 10 $ 7,801 $ ( 97 ) 144 $ 103,724 $ ( 1,847 ) The Company analyzed its investment portfolio in accordance with its OTTI review procedures and determined the Company did not need to record a credit-related OTTI loss, nor recognize a non credit-related OTTI loss in other comprehensive income for the years ended December 31, 2022, 2021, and 2020. The Company’s sources of net investment income are as follows (dollars in thousands): December 31, 2022 2021 2020 Debt securities $ 2,517 $ 2,217 $ 3,213 Equity securities 52 194 220 Cash, cash equivalents, and short-term investments 776 2 138 Total investment income 3,345 2,413 3,571 Investment expenses ( 302 ) ( 445 ) ( 415 ) Net investment income $ 3,043 $ 1,968 $ 3,156 The following table summarizes the gross realized gains and losses from sales or maturities of available-for-sale debt securities and equity securities, as follows (dollars in thousands): December 31, 2022 2021 2020 Debt securities: Gross realized gains $ 6 $ 63 $ 4,646 Gross realized losses ( 155 ) ( 6 ) ( 8 ) Total debt securities ( 149 ) 57 4,638 Equity securities: Gross realized gains 375 4,605 4,854 Gross realized losses ( 1,731 ) ( 1,784 ) ( 1,366 ) Total equity securities ( 1,356 ) 2,821 3,488 Total net realized investment gains $ ( 1,505 ) $ 2,878 $ 8,126 Proceeds from the sales of available-for-sale securities were $ 32.0 million, $ 31.7 million and $ 101.2 million for the years ended December 31, 2022, 2021, and 2020, respectively. The gross realized gains from sales of available-for-sale securities for the years ended December 31, 2022, 2021, and 2020 were $ 5,000 , $ 27,000 , and $ 4.6 million, respectively. The gross realized losses from sales of available-for-sale securities for the years ended December 31, 2022, 2021, and 2020 were $ 155,000 , $ 6,000 , and $ 0 , respectively. As of December 31, 2022, 2021, and 2020 there were $ 0 , $ 1.0 million, and $1 .7 million of payables from securities purchased, respectively. As of December 31, 2022, 2021, and 2020 there were $ 650,000 , $ 523,000 , and $ 809,000 of receivables from securities sold, respectively. The Company's gross unrealized losses related to its equity investments were $ 638,000 , $ 1.0 million, and $ 0 as of December 31, 2022, 2021, and 2020, respectively. The Company had no gross unrealized gains related to its equity investments as of December 31, 2022 and 2021, respectively. The Company's gross unrealized gains related to its equity investments were $ 1.0 million as of December 31, 2020. The Company also carries other equity investments that do not have a readily determinable fair value and are recorded at cost, less impairment or observable changes in price. We review these investments for impairment during each reporting period. There was no impairment or observable changes in price recorded during 2022 related to the Company's equity securities without readily determinable fair value. These investments are a component of Other Assets in the Consolidated Balance Sheets. The value of these investments as of December 31, 2022 were $ 1.8 million. The table below summarizes the amortized cost and fair value of available-for-sale debt securities by contractual maturity at December 31, 2022. Actual maturities may differ from contractual maturities because certain borrowers have the right to call or prepay obligations with or without call or prepayment penalties (dollars in thousands): Amortized Estimated Due in one year or less $ 4,876 $ 4,770 Due after one year through five years 28,396 25,963 Due after five years through ten years 23,974 19,782 Due after ten years 11,421 8,358 Securities with contractual maturities 68,667 58,873 Asset-backed securities 21,742 20,496 Mortgage-backed securities 29,194 24,037 Commercial mortgage-backed securities 3,414 3,228 Collateralized mortgage obligations 4,102 3,567 Total debt securities $ 127,119 $ 110,201 At December 31, 2022 and 2021 , the Insurance Companies Subsidiaries had an aggregate of $ 8.0 million and $ 8.5 million, respectively, on deposit in trust accounts to meet the deposit requirements of various state insurance departments. At December 31, 2022 and 2021 , the Company had $ 95.7 million and $ 76.1 million held in trust accounts to meet collateral requirements with other third-party insurers, relating to various fronting arrangements. There are withdrawal and other restrictions on these deposits, including the type of investments that may be held, however, the Company may generally invest in high-grade bonds and short-term investments and earn interest on the funds.

Fair Value Measurements

Fair Value Measurements	12 Months Ended
	Dec. 31, 2022
Fair Value Disclosures [Abstract]
Fair Value Measurements	. Fair Value Measurements The Company’s financial instruments include assets carried at fair value, as well as debt carried at face value, net of unamortized debt issuance costs, and are disclosed at fair value in this note. All fair values disclosed in this note are determined on a recurring basis other than the debt which is a non-recurring fair value measure. Fair value is defined as the price that would be received for an asset or paid to transfer a liability in the principal most advantageous market for the asset or liability in an orderly transaction between market participants. In determining fair value, the Company applies the market approach, which uses prices and other relevant data based on market transactions involving identical or comparable assets and liabilities. The inputs to valuation techniques used to measure fair value are prioritized into a three-level hierarchy. The hierarchy gives the highest priority to quoted prices from sources independent of the reporting entity (“observable inputs”) and the lowest priority to prices determined by the reporting entity’s own assumptions about market participant assumptions developed based on the best information available in the circumstances (“unobservable inputs”). The fair value hierarchy is as follows: Level 1 —Valuations that are based on quoted prices (unadjusted) in active markets for identical assets or liabilities. Level 2 —Valuations that are based on observable inputs (other than Level 1 prices) such as quoted prices for similar assets or liabilities at the measurement date; quoted prices in markets that are not active; or other inputs that are observable, either directly or indirectly, for substantially the full term of the asset or liability. Level 3 —Unobservable inputs that are supported by little or no market activity. The unobservable inputs represent the Company’s best assumption of how market participants would price the assets or liabilities. Net Asset Value (NAV) —The fair values of investment company limited partnership investments and mutual funds are based on the capital account balances reported by the investment funds subject to their management review and adjustment. These capital account balances reflect the fair value of the investment funds. The following tables present the Company’s assets and liabilities measured at fair value, classified by the valuation hierarchy as of December 31, 2022 and 2021 (dollars in thousands): December 31, 2022 Fair Value Measurements Using Total Level 1 Level 2 Level 3 Assets: Debt Securities: U.S. Government $ 7,498 $ — $ 7,498 $ — State and local government 20,816 — 20,816 — Corporate debt 30,559 — 30,559 — Asset-backed securities 20,496 — 20,496 — Mortgage-backed securities 24,037 — 24,037 — Commercial mortgage-backed securities 3,228 — 3,228 — Collateralized mortgage obligations 3,567 — 3,567 — Total debt securities 110,201 — 110,201 — Equity Securities 917 160 757 — Short-term investments 25,929 25,929 — — Total marketable investments measured at fair value $ 137,047 $ 26,089 $ 110,958 $ — Investments measured at NAV: Investment in limited partnership 350 Total assets measured at fair value $ 137,397 Liabilities: Senior Unsecured Notes * $ 22,430 $ — $ 22,430 $ — Subordinated Notes * 11,300 — — 11,300 Total Liabilities (non-recurring fair value measure $ 33,730 $ — $ 22,430 $ 11,300 * Carried at face value of debt net of unamortized debt issuance costs on the consolidated balance sheet December 31, 2021 Fair Value Measurements Using Total Level 1 Level 2 Level 3 Assets: Debt Securities: U.S. Government $ 20,720 $ — $ 20,720 $ — State and local government 30,429 — 30,429 — Corporate debt 30,346 — 30,346 — Asset-backed securities 28,438 — 28,438 — Mortgage-backed securities 32,521 — 32,521 — Commercial mortgage-backed securities 1,690 — 1,690 — Collateralized mortgage obligations 5,639 — 5,639 — Total debt securities 149,783 — 149,783 — Equity Securities 9,437 9,154 283 — Short-term investments 23,013 23,013 — — Total marketable investments measured at fair value $ 182,233 $ 32,167 $ 150,066 $ — Investments measured at NAV: Investment in limited partnership 494 Total assets measured at fair value $ 182,727 Liabilities: Senior Unsecured Notes * $ 24,118 $ — $ 24,118 $ — Subordinated Notes * 11,704 — — 11,704 Total Liabilities measured at fair value $ 35,822 $ — $ 24,118 $ 11,704 * Carried at face value of debt net of unamortized debt issuance costs on the consolidated balance sheet Level 1 investments consist of equity securities traded in an active exchange market. The Company uses unadjusted quoted prices for identical instruments to measure fair value. Level 1 also includes money market funds and other interest-bearing deposits at banks, which are reported as short-term investments. The fair value measurements that were based on Level 1 inputs comprise 18 % of the fair value of the total marketable investments measured at fair value as of December 31, 2022. Level 2 investments include debt securities and equity securities, which consist of U.S. government agency securities, state and local municipal bonds (including those held as restricted securities), corporate debt securities, mortgage-backed and asset-backed securities. The fair value of securities included in the Level 2 category were based on the market values obtained from a third party pricing service that were evaluated using pricing models that vary by asset class and incorporate available trade, bid and other observable market information. The third party pricing service monitors market indicators, as well as industry and economic events. The fair value measurements that were based on Level 2 inputs comprise 82 % of the fair value of the total marketable investments measured at fair value as of December 31, 2022. The Company obtains pricing for each security from independent pricing services, investment managers or consultants to assist in determining fair value for its Level 2 investments. To validate that these quoted prices are reasonable estimates of fair value, the Company performs various quantitative and qualitative procedures, such as (i) evaluation of the underlying methodologies, (ii) analysis of recent sales activity, (iii) analytical review of our fair values against current market prices and (iv) comparison of the pricing services’ fair value to other pricing services’ fair value for the same investment. No markets for the investments were determined to be inactive at period-ends. Based on these procedures, the Company did not adjust the prices or quotes provided from independent pricing services, investment managers or consultants. As of December 31, 2022 and 2021, the fair value of the subordinated debt reported at amortized cost was considered a Level 3 liability in the fair value hierarchy and is entirely comprised of the Company's Subordinated Notes. In determining the fair value of the Subordinated Notes outstanding at December 31, 2022 and 2021, the security attributes (issue date, maturity, coupon, calls, etc.) and market rates on September 24, 2018 (the date of the restated and amended agreement which was repriced at that time) were entered into a valuation model. A lognormal trinomial interest rate lattice was created within the model to compute the option adjusted spread (“OAS”) which is the amount, in basis points, of interest rate required to be paid under the debt agreement over the risk-free U.S. Treasury rates. The OAS was then entered back into the model along with the December 31, 2022 and 2021 , U.S. Treasury rates, respectively. A new lattice was generated and the fair value was computed from the OAS. There were no changes in assumptions of credit risk from the issuance date.

Deferred Policy Acquisition Cos

Deferred Policy Acquisition Costs	12 Months Ended
	Dec. 31, 2022
Deferred Policy Acquisition Costs Disclosures [Abstract]
Deferred Policy Acquisition Costs	. Deferred Policy Acquisition Costs The Company defers costs incurred which are incremental and directly related to the successful acquisition of new or renewal insurance business, net of corresponding amounts of ceded reinsurance commissions. Net deferred policy acquisition costs are amortized and charged to expense in proportion to premium earned over the estimated policy term. The Company anticipates that its deferred policy acquisition costs will be fully recoverable and there were no premium deficiencies for the years December 31, 2022, 2021, and 2020 . The activity in deferred policy acquisition costs, net of reinsurance transactions, is as follows (dollars in thousands): December 31, 2022 2021 2020 Balance at beginning of period $ 12,267 $ 12,243 $ 11,906 Deferred policy acquisition costs 20,202 28,475 26,442 Amortization of policy acquisition costs ( 22,179 ) ( 28,451 ) ( 26,105 ) Net change ( 1,977 ) 24 337 Balance at end of period $ 10,290 $ 12,267 $ 12,243

Unpaid Losses and Loss Adjustme

Unpaid Losses and Loss Adjustment Expenses	12 Months Ended
	Dec. 31, 2022
Insurance Loss Reserves [Abstract]
Unpaid Losses and Loss Adjustment Expenses	. Unpaid Losses and Loss Adjustment Expenses The Company establishes reserves for unpaid losses and LAE which represent the estimated ultimate cost of all losses incurred that were both reported and unreported (i.e., incurred but not yet reported losses, or “IBNR”) and LAE incurred as well as a provision for estimated future costs related to claim settlement for all claims that remain unpaid at the balance sheet date. The Company’s reserving process takes into account known facts and interpretations of circumstances and factors including the Company’s experience with similar cases, actual claims paid, historical trends involving claim payment patterns and pending levels of unpaid claims, loss management programs, product mix and contractual terms, changes in law and regulation, judicial decisions, and economic conditions. In the normal course of business, the Company may also supplement its claims processes by utilizing third party adjusters, appraisers, engineers, inspectors, and other professionals and information sources to assess and settle catastrophe and non-catastrophe related claims. The effects of inflation are implicitly considered in the reserving process. Reserves are estimates of unpaid portions of losses that have occurred, including IBNR losses, therefore the establishment of appropriate reserves, is an inherently uncertain and complex process. The ultimate cost of losses may vary materially from recorded amounts, which are based on management’s best estimates. The highest degree of uncertainty is associated with reserves for losses incurred in the current reporting period as it contains the greatest proportion of losses that have not been reported or settled. The Company regularly updates its reserve estimates as new information becomes available and as events unfold that may affect the resolution of unsettled claims. Changes in prior year reserve estimates, which may be material, are reported in the results of operations in the period such changes are determined to be needed and recorded. Management believes that the reserve for losses and LAE, any related estimates of reinsurance recoverables, is appropriately established in the aggregate and adequate to cover the ultimate net cost of reported and unreported claims arising from losses which had occurred by the date of the consolidated financial statements based on available facts and in accordance with applicable laws and regulations. The table below provides the changes in the reserves for losses and LAE, net of recoverables from reinsurers, for the periods indicated (dollars in thousands): December 31, 2022 2021 2020 Gross reserves - beginning of period $ 139,085 $ 111,270 $ 107,246 Less: reinsurance recoverables on unpaid losses 40,344 24,218 22,579 Net reserves - beginning of period 98,741 87,052 84,667 Add: incurred losses and loss adjustment expenses, net Current period 57,156 50,429 40,634 Prior period 24,284 19,432 15,594 Total net incurred losses and loss adjustment 81,440 69,861 56,228 Deduct: loss and loss adjustment expense payments, Current period 20,894 18,984 13,599 Prior period 76,399 39,188 40,244 Total net loss and loss adjustment expense 97,293 58,172 53,843 Net reserves - end of period 82,888 98,741 87,052 Plus: reinsurance recoverables on unpaid losses 82,651 40,344 24,218 Gross reserves - end of period $ 165,539 $ 139,085 $ 111,270 There was $ 24.3 million, $ 19.4 million, and $ 15.6 million of adverse development on prior accident year reserves in 2022, 2021 and 2020, respectively. There were no significant changes in the key methods utilized in the analysis and calculations of the Company’s reserves during 2022, 2021 or 2020. Of the $ 24.3 million of adverse development in 2022, $ 1.8 million was related to the 2021 accident year, $ 4.0 million was related to the 2020 accident year, $ 9.6 million was related to the 2019 accident year, $ 5.2 million was related to the 2018 accident year, and $ 3.7 million was related to 2017 and prior accident years. The adverse development was mostly related to the Company's commercial liability lines and was driven by multiple factors including significant social inflation generating higher severity than historical experience, and longer tail exposure than anticipated, particularly in certain jurisdictions. In 2021, the adverse development consisted of $ 18.5 million from commercial lines and $ 957,000 from personal lines. Of the $ 18.5 million of adverse development in commercial lines, the Company experienced $ 12.0 million and $ 6.5 million of adverse development in its hospitality and small business lines of business, respectively. The Company experienced $ 2.0 million of catastrophe losses, net of reinsurance recoverables, during the first quarter of 2021 from winter Storm Uri. In 2020, the adverse development consisted of $ 15.2 million from commercial lines and $ 352,000 from personal lines. Of the $ 15.2 million of adverse development in commercial lines, the Company experienced $ 12.0 million and $ 3.2 million of adverse development in its hospitality and small business lines of business, respectively. The $ 352,000 of adverse development in personal lines mostly was related to wind-exposed business. Loss Development Tables The following tables represent cumulative incurred loss and allocated loss adjustment expenses ("ALAE"), net of reinsurance, by accident year and cumulative paid loss and ALAE, net of reinsurance, by accident year, for the years ended December 31, 2013 to 2022, as well as total IBNR and the cumulative number of reported claims for the year ended December 31, 2022, by reportable segment and accident year (dollars in thousands). The tables do not include reinsurance recoverables from the LPT. Commercial Lines Incurred loss and allocated loss adjustment expenses, net of reinsurance Total Cumulative Accident Year 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 2022 2022 2013 10,018 9,435 9,893 10,237 11,252 11,218 11,624 11,804 11,867 12,046 — 613 2014 19,709 19,907 22,711 26,367 28,145 28,766 29,045 29,175 29,011 — 1,754 2015 22,442 26,633 31,861 34,478 36,372 37,795 38,824 39,093 26 2,361 2016 32,396 34,935 40,440 44,355 46,089 46,993 48,677 201 3,557 2017 44,251 44,495 49,749 51,883 55,589 56,649 671 5,832 2018 42,624 42,432 49,741 55,261 60,102 1,637 6,124 2019 41,286 42,129 46,329 55,263 4,529 6,320 2020 33,867 35,328 39,193 3,787 3,830 2021 40,388 42,266 8,744 2,861 2022 41,708 16,067 1,965 Total $ 424,008 $ 35,662 Commercial lines Cumulative paid loss and allocated loss adjustment expenses, net of reinsurance Accident Year 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 2013 3,979 6,211 7,643 8,622 10,147 10,650 11,137 11,620 11,702 11,935 2014 8,715 13,977 17,458 22,446 25,609 27,544 28,389 28,648 28,608 2015 10,470 17,817 22,549 30,475 34,497 35,833 37,563 38,685 2016 10,255 19,135 27,785 37,967 41,945 43,644 46,957 2017 12,448 23,020 34,205 42,308 47,148 52,800 2018 10,375 19,799 31,633 41,577 50,508 2019 10,078 20,462 28,958 39,893 2020 10,217 17,332 24,225 2021 12,870 21,313 2022 12,839 Total $ 327,763 Net Unpaid losses and ALAE, years 2013 through 2022 $ 96,245 Unpaid losses and ALAE, prior to 2013* 177 Unpaid Losses, LPT ( 25,913 ) Unpaid losses and ALAE, net of reinsurance $ 70,509 * Presented as unaudited required supplementary information. Personal Lines Incurred loss and allocated loss adjustment expenses, net of reinsurance Total Cumulative Accident For the years ended December 31, Year 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 2022 2022 2013 18,034 17,996 18,925 19,138 19,167 19,202 19,222 19,226 19,227 19,365 — 5,208 2014 17,951 17,471 17,735 17,880 17,929 18,082 18,095 18,097 18,052 — 3,737 2015 10,877 13,445 14,721 15,285 15,364 15,427 15,427 15,448 — 2,152 2016 11,619 13,418 14,949 15,550 15,655 15,634 15,679 — 1,814 2017 14,058 13,550 14,493 14,793 14,911 14,957 — 2,917 2018 5,893 6,378 6,283 6,382 6,298 — 803 2019 3,099 2,712 2,898 2,862 — 342 2020 2,339 2,590 2,636 — 366 2021 4,409 4,332 116 580 2022 9,404 1,427 652 Total $ 109,033 $ 1,543 Personal lines Cumulative paid loss and allocated loss adjustment expenses, net of reinsurance Accident For the years ended December 31, Year 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 2013 9,955 15,883 18,052 18,600 19,014 19,174 19,214 19,222 19,227 19,365 2014 12,819 16,515 17,260 17,746 17,855 18,047 18,068 18,070 18,025 2015 7,771 11,873 13,844 15,159 15,250 15,290 15,416 15,444 2016 7,119 11,238 14,442 15,110 15,351 15,452 15,679 2017 8,320 12,944 14,004 14,526 14,866 14,957 2018 4,296 5,618 6,100 6,242 6,244 2019 2,119 2,604 2,692 2,850 2020 1,307 2,455 2,605 2021 3,022 3,980 2022 5,397 Total $ 104,546 Net Unpaid losses and ALAE, years 2013 through 2022 $ 4,487 Unpaid losses and ALAE, prior to 2013* — Unpaid losses and ALAE, net of reinsurance $ 4,487 * Presented as unaudited required supplementary information. Total Lines Incurred loss and allocated loss adjustment expenses, net of reinsurance Total Cumulative number of reported claims Accident For the years ended December 31, Year 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 2022 2022 2013 28,052 27,431 28,817 29,375 30,419 30,420 30,846 31,030 31,094 31,411 — 5,821 2014 37,660 37,378 40,446 44,247 46,074 46,848 47,140 47,272 47,063 — 5,491 2015 33,319 40,078 46,581 49,763 51,736 53,222 54,251 54,541 26 4,513 2016 44,015 48,353 55,389 59,905 61,744 62,627 64,356 201 5,371 2017 58,309 58,045 64,242 66,676 70,500 71,606 671 8,749 2018 48,517 48,810 56,024 61,643 66,400 1,637 6,927 2019 44,385 44,841 49,227 58,125 4,529 6,662 2020 36,206 37,918 41,829 3,787 4,196 2021 44,797 46,598 8,860 3,441 2022 51,112 17,494 2,617 Total 533,041 37,205 Total lines Cumulative paid loss and allocated loss adjustment expenses, net of reinsurance Accident For the years ended December 31, Year 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 2013 13,934 22,094 25,695 27,223 29,162 29,824 30,351 30,842 30,929 31,300 2014 21,534 30,492 34,718 40,192 43,464 45,591 46,457 46,718 46,633 2015 18,241 29,690 36,393 45,634 49,747 51,123 52,979 54,129 2016 17,374 30,373 42,227 53,077 57,296 59,096 62,636 2017 20,768 35,964 48,209 56,834 62,014 67,757 2018 14,671 25,417 37,733 47,819 56,752 2019 12,197 23,066 31,650 42,743 2020 11,524 19,787 26,830 2021 15,892 25,293 2022 18,236 Total $ 432,309 Net Unpaid losses and ALAE, years 2013 through 2022 $ 100,732 Unpaid losses and ALAE, prior to 2013* 177 Unpaid losses, LPT ( 25,913 ) Unpaid losses and ALAE, net of reinsurance $ 74,996 * Presented as unaudited required supplementary information. The following table reconciles the loss development information to the consolidated balance sheet for the year ended December 31, 2022, by reportable segment (dollars in thousands). December 31, Net unpaid losses claims and ALAE Commercial Lines $ 70,509 Personal Lines 4,487 Total unpaid losses and LAE, net of reinsurance 74,996 Reinsurance recoverable on losses and LAE Commercial Lines 81,301 Personal Lines 1,350 Total reinsurance recoverable on unpaid losses and LAE 82,651 ULAE expense 7,892 Total gross unpaid losses and LAE $ 165,539 Loss Duration Disclosure (unaudited) The following table represents the average annual percentage payout of incurred losses by age, net of reinsurance, for each reportable segment. Average annual percentage payout of incurred losses by age, net of reinsurance Year 1 Year 2 Year 3 Year 4 Year 5 Year 6 Year 7 Year 8 Year 9 Year Commercial Lines 34.4 % 23.0 % 17.7 % 10.0 % 8.0 % 3.6 % 1.8 % 0.8 % 0.4 % 0.3 % Personal Lines 69.4 % 16.6 % 10.1 % 2.6 % 0.9 % 0.2 % 0.1 % 0.1 % 0.0 % 0.0 % Total Lines 35.7 % 22.8 % 17.5 % 9.7 % 7.7 % 3.5 % 1.7 % 0.8 % 0.4 % 0.2 %

Reinsurance

Reinsurance	12 Months Ended
	Dec. 31, 2022
Reinsurance Disclosures [Abstract]
Reinsurance	8. Reinsurance In the normal course of business, the Company participates in reinsurance agreements in order to limit losses that may arise from catastrophes or other individually severe events. The Company primarily ceded all specific loss commercial liability risks in excess of $ 340,000 in 2022, and $ 400,000 in 2021 and 2020. The Company ceded specific loss commercial property risks in excess of $ 300,000 in 2022 and $ 200,000 in 2021. The Company ceded 40 % of specific loss commercial property risks in excess of $ 400,000 and 60 % in excess of $ 300,000 in 2020. The Company ceded homeowners specific risks in excess of $ 300,000 in 2022, 2021, and 2020. A "treaty" is a reinsurance agreement in which coverage is provided for a class of risks and does not require policy by policy underwriting of the reinsurer. "Facultative" reinsurance is where a reinsurer negotiates an individual reinsurance agreement for every policy it will reinsure on a policy-by-policy basis. A loss is covered under a reinsurance contract if the loss occurs within the effective dates of the agreement notwithstanding when the loss is reported. The Company entered into new specific loss reinsurance treaties on December 31, 2021 and January 1, 2022 which included a 40 % ceding commission. The reinsurance premiums related to these treaties increased by the same amount as the ceding commission. Reinsurance does not discharge the Company, as the direct insurer, from liability to its policyholders. Failure of reinsurers to honor their obligations could result in losses to the Company. The Company evaluates the financial condition of its reinsurers and monitors the concentration of credit risk arising from similar geographic regions, activities, or economic characteristics of the reinsurers to minimize its exposure to significant losses from reinsurer insolvencies. To date, the Company has not experienced any significant difficulties in collecting reinsurance recoverables. The Company's current reinsurance structure includes the following primary categories: Casualty Clash • Clash coverage is a type of reinsurance that provides additional coverage in the event that one casualty loss event results in two or more claims and recovery under the reinsurance treaties may otherwise be limited due to the amount, type or number of claims. Clash reinsurance further protects the balance sheet as it reduces the potential maximum loss on either a single risk or a large number of risks. • Effective January 1, 2022 through December 31, 2022, the company was party to a workers’ compensation and casualty clash reinsurance treaty with a limit of $ 29.0 million in excess of $ 1.0 million. • Effective January 1, 2019 through December 31, 2021, the Company was party to a workers' compensation and casualty clash reinsurance treaty with a limit of $ 19.0 million in excess of a $ 1.0 million retention. Effective January 1, 2021 through December 31, 2021, the Company ceded 87.0 % of its casualty clash risks with a limit of $ 10.0 million in excess of a $ 20.0 million retention. Facultative • The Company was party to a facultative reinsurance agreement with a large reinsurer for commercial auto physical damage risks primarily in excess of $ 400,000 . • The Company was party to a facultative reinsurance agreement with a large reinsurer for property risks with total insured values above the other reinsurance treaty limits. Liability • Effective January 1, 2019 through December 31, 2022, the Company was party to an excess of loss reinsurance treaty for commercial liability coverage with a limit of $ 600,000 in excess of $ 400,000 . Property • Effective January 1, 2020 through December 31, 2022, the Company was party to an excess of loss reinsurance treaty for personal property coverage with a limit of $ 1.7 million in excess of $ 300,000 , for homeowners' and dwelling fire business. • Effective January 1, 2022 through December 31, 2022, the Company was party to an excess of loss reinsurance treaty for commercial property coverage with a limit of $ 7.7 million in excess of $ 300,000 . • Effective January 1, 2021 through December 31, 2021, the Company was party to an excess of loss reinsurance treaty for commercial property coverage with a limit of $ 7.8 million in excess of $ 200,000 . • Effective January 1, 2020 through December 31, 2020, the Company was party to an excess of loss reinsurance treaty for commercial property coverage with a limit of $ 7.7 million in excess of $ 300,000 . • At December 31, 2022, the Company was covered for property catastrophe losses up to $ 28.0 million in excess of a $ 2.0 million retention for the first event. This treaty terminates on June 1, 2023 . • At December 31, 2021, the Company was covered for property catastrophe losses up to $ 28.0 million in excess of a $ 2.0 million retention for the first event. This treaty terminates on June 1, 2022 . • At December 31, 2020, the Company was covered for property catastrophe losses up to $ 28.0 million in excess of a $ 2.0 million retention for the first event. This treaty terminated on June 1, 2021 . Multiple Line • Effective January 1, 2019 through December 31, 2021, the Company was party to a multi-line excess of loss treaty that covers commercial property and casualty losses up to $ 600,000 in excess of a $ 400,000 retention. Quota Share • The Company cedes 90 % to 100 % of its commercial umbrella coverages under quota share treaties. Under a quota share agreement, the reinsurer pays a percentage of all losses the insurer sustains in return for a similar percent of the premiums written on that risk. A ceding commission is paid by the reinsurer to the insurer to cover acquisition and operating expenses. Loss Portfolio Transfe r • On November 1, 2022, the Company entered into a loss portfolio transfer (“LPT”) reinsurance agreement with Fleming Reinsurance Ltd (“Fleming Re”). Under the agreement, Fleming Re will cover an aggregate limit of $ 66.3 million of paid losses on $ 40.8 million of stated net reserves as of June 30, 2022, relating to accident years 2019 and prior. This covers substantially all of the commercial liability lines underwritten by the Company. Within the aggregate limit, there is a $ 5.5 million loss corridor in which the Company retains losses in excess of $ 40.8 million. Fleming Re is then responsible to cover paid losses in excess of $ 46.3 million up to $ 66.3 million. Accordingly, there is $ 20.0 million of adverse development cover for accident years 2019 and prior. Under the agreement, Fleming Re was compensated with $ 40.8 million for stated net reserves as of June 30, 2022, plus a one-time risk fee of $ 5.4 million. Recoverables due to the Company under this agreement are recorded as reinsurance recoverables. The agreement is between CIC and WPIC and Fleming Re. As of December 31, 2022, the Company has recorded losses through the $ 5.5 million corridor and $ 644,000 into the $ 20.0 million layer. As of December 31, 2022, the Consolidated Balance Sheet included $ 3.8 million of reinsurance recoverables on paid losses related to the LPT, and $ 25.9 million of reinsurance recoverables on unpaid losses related to the LPT. Equipment Breakdown, Employment Practice Liability, and Data Compromise and Identity Recovery • The Company ceded 100 % of a small number of equipment breakdown, employment practices liability, and data compromise coverages that are occasionally bundled with other products under a quota share agreement with a reinsurer. The Company assumes written premiums under a few fronting arrangements. The fronting arrangements are with unaffiliated insurers who write on behalf of the Company in markets that require a higher A.M. Best rating than the Company’s rating, or where the policies are written in a state where the Company is not licensed or for other strategic reasons. The Company assumed $ 42.2 million, $ 34.3 million, and $ 28.9 million of written premiums under the insurance fronting arrangements for the years ended December 31, 2022, 2021 and 2020, respectively. The following table presents the effects of reinsurance and assumption transactions on written premiums, earned premiums and losses and LAE (dollars in thousands). In 2022, ceded written and earned premium amounts included $ 1.6 million of reinsurance reinstatement costs relating to Hurricane Ian. In 2021, ceded written and earned amounts included $ 340,000 of reinsurance reinstatement costs relating to Winter Storm Uri. In 2021 and 2020, the ceded written and earned premium amounts include $ 86,000 and $ 195,000 of reinsurance reinstatement costs relating to Hurricane Irma, respectively. Year Ended December 31, 2022 2021 2020 Written premiums: Direct $ 95,832 $ 97,801 $ 82,430 Assumed 42,187 34,294 28,905 Ceded ( 46,787 ) ( 30,666 ) ( 18,395 ) Net written premiums $ 91,232 $ 101,429 $ 92,940 Earned premiums: Direct $ 97,843 $ 91,943 $ 75,130 Assumed 37,558 31,107 31,484 Ceded ( 38,690 ) ( 24,248 ) ( 17,511 ) Net earned premiums $ 96,711 $ 98,802 $ 89,103 Loss and loss adjustment expenses: Direct $ 73,000 $ 71,021 $ 48,780 Assumed 43,487 25,740 24,429 Ceded ( 35,047 ) ( 26,900 ) ( 16,981 ) Net loss and LAE $ 81,440 $ 69,861 $ 56,228

Debt

Debt	12 Months Ended
	Dec. 31, 2022
Debt Disclosure [Abstract]
Debt	. Debt As of December 31, 2022 , the Company’s debt is comprised of two instruments: $ 24.4 million of publicly traded senior unsecured notes which were issued in 2018 and $ 10.5 million of privately placed Subordinated Notes. A summary of the Company's outstanding debt is as follows (dollars in thousands): December 31, 2022 2021 Senior unsecured notes $ 24,186 $ 23,926 Subordinated notes 9,690 9,638 Total $ 33,876 $ 33,564 Senior unsecured notes The Company issued $ 25.3 million of Notes in 2018. The Notes bear an interest rate of 6.75 % per annum, payable quarterly at the end of March, June, September and December and mature on September 30, 2023 . The Company may redeem the Notes, in whole or in part, at face value at any time after September 30, 2021. The Company did no t repurchase any of the Notes during 2022 or 2021. Management plans to issue new public debt or sell assets to provide sufficient cash flow to pay off the senior unsecured notes that are coming due within the next twelve months. Management believes it is probable that it will be able to issue new public debt and/or sell assets as necessary to repay the senior unsecured notes by September 30, 2023. Subordinated Notes The Company also has outstanding $ 10.5 million of Subordinated Notes maturing on September 30, 2038 . The Subordinated Notes bear an interest rate of 7.5 % per annum until September 30, 2023, and 12.5 % thereafter, and allow for four quarterly interest payment deferrals. Interest is payable quarterly at the end of March, June, September and December . Beginning September 30, 2021, the Company may redeem the Subordinated Notes, in whole or in part, for a call premium of $ 1.1 million. The call premium escalates each quarter to ultimately $ 1.75 million on September 30, 2023, then steps up to $ 3.05 million on December 31, 2023, and increases quarterly at a 12.5 % per annum rate thereafter. As of December 31, 2022 , the carrying value of the Notes and Subordinated Notes are offset by $ 195,000 and $ 810,000 of debt issuance costs, respectively. The debt issuance costs are amortized through interest expense over the life of the loans. The Subordinated Notes contain various restrictive financial debt covenants that relate to the Company’s minimum tangible net worth, minimum fixed-charge coverage ratios, dividend paying capacity, reinsurance retentions, and risk-based capital ratios. As of December 31, 2022, the Company was in compliance with all of its financial covenants. Line of credit The Company maintained a $ 10.0 million line of credit with a national bank (the “Lender”) during 2022. The line of credit carried an interest rate at LIBOR plus 2.75 % per annum, payable monthly. The line of credit agreement matured on December 1, 2022, and was not renewed. Paycheck Protection Program loan On April 24, 2020, the Company received a $ 2.7 million loan from the line of credit Lender pursuant to the Paycheck Protection Program of the CARES Act administered by the U.S. Small Business Administration (“SBA”). The Company received notice from the SBA that the loan was 100% forgiven, including accrued interest, on July 8, 2021 . This resulted in a $ 2.8 million gain that is included in Other Gains on the Consolidated Statement of Operations in 2021 .

Income Taxes

Income Taxes	12 Months Ended
	Dec. 31, 2022
Income Tax Disclosure [Abstract]
Income Taxes	10. Income Taxes At December 31, 2022 , the Company had current income tax receivable of $ 58,000 included in other assets in the consolidated balance sheets. At December 31, 2021 , the Company had current income tax payable of $ 34,000 included in other assets in the consolidated balance sheets. The income tax expense (benefit) is comprised of the following (dollars in thousands): Year Ended December 31, 2022 2021 2020 Current tax expense (benefit) $ ( 45 ) $ 208 $ 6 Deferred tax expense (benefit) ( 9,396 ) — — Total income tax expense (benefit) $ ( 9,441 ) $ 208 $ 6 The income tax expense (benefit) differed from the amounts computed by applying the statutory U.S. federal income tax rate of 21 % in 2022, 2021 and 2020 to pretax income as a result of the following (dollars in thousands): Year Ended December 31, 2022 2021 2020 Income (loss) before income taxes $ ( 20,490 ) $ ( 1,710 ) $ ( 238 ) Statutory U.S. federal income tax rate ( 4,303 ) ( 359 ) ( 50 ) State income taxes, net of federal benefit ( 5,984 ) 174 44 Tax‑exempt investment income and dividend received deduction ( 22 ) ( 40 ) ( 50 ) Nondeductible meals and entertainment 79 33 23 Valuation allowance on deferred tax assets 3,715 676 ( 205 ) Equity-earnings from Affiliate 195 170 88 Net gain from sale of agency assets ( 2,848 ) — — Utilization of state NOLs ( 386 ) — — PPP Loan forgiveness — ( 578 ) — Other 113 132 156 Income tax expense (benefit) $ ( 9,441 ) $ 208 $ 6 Effective tax rate 46.1 % ( 12.2 )% ( 2.6 )% The tax effects of temporary differences that give rise to significant portions of the deferred tax assets and deferred tax liabilities are presented below (dollars in thousands): December 31, 2022 2021 Deferred tax assets: Discounted unpaid losses and loss adjustment expenses $ 1,217 $ 1,555 Unearned premiums 2,324 2,561 Net operating loss carryforwards 12,152 12,544 Net unrealized losses on investments 3,687 418 State net operating loss carryforwards 5,097 822 Other 403 102 Gross deferred tax assets 24,880 18,002 Less valuation allowance ( 21,663 ) ( 14,594 ) Total deferred tax assets, net of allowance 3,217 3,408 Deferred tax liabilities: Investment basis difference 23 15 Tax rate change transition discounting 137 183 Equity investment in Affiliate 691 470 Net unrealized gains on investments — — Deferred policy acquisition costs 2,161 2,576 Intangible assets 115 115 Property and equipment 41 47 Other 49 2 Total deferred tax liabilities 3,217 3,408 Net deferred tax liability $ — $ — The net deferred tax liability is recorded in accounts payable and accrued expenses in the consolidated balance sheets. As of December 31, 2022 , the Company has NOL carryforwards for federal income tax purposes of $ 65.6 million, of which $ 50.4 million expire in tax years 2030 through 2042 and $ 15.2 million never expire. Of this amount, $ 7.6 million are limited in the amount that can be utilized in any one year and may expire before they are realized under Section 382 of the Internal Revenue Code. The Company has state net operating loss carryforwards of $ 107.2 million, which expire in tax years 2023 through 2042. Management assesses the available positive and negative evidence to estimate whether sufficient future taxable income will be generated to permit the use of the existing deferred tax assets under the guidance of ASC 740. A significant piece of objective negative evidence evaluated was the cumulative loss incurred over the three‑year period ended December 31, 2022. Such objective evidence limits the Company's ability to consider other subjective evidence, such as management's projections for future growth. Based on its evaluation, the Company has recorded a valuation allowance of $ 21.7 million and $ 14.6 million at December 31, 2022 and 2021, respectively, to reduce the deferred tax assets to an amount that is more likely than not to be realized based on the provisions in ASC 740. The amount of the deferred tax assets considered realizable, however, could be adjusted if estimates of future taxable income during the carryforward period are reduced or if objective negative evidence in the form of cumulative losses is no longer present, and additional weight may be given to subjective evidence, such as the Company’s projections for growth. The Company files consolidated federal income tax returns. For the years before 2019, the Company is no longer subject to U.S. federal examinations; however, the Internal Revenue Service has the ability to review years prior to 2019 to the extent the Company utilized tax attributes carried forward from those prior years. The statute of limitations on state filings is generally three to four years .

Statutory Financial Data, Risk-

Statutory Financial Data, Risk-Based Capital and Dividend Restrictions	12 Months Ended
	Dec. 31, 2022
Insurance [Abstract]
Statutory Financial Data, Risk-Based Capital and Dividend Restrictions	11. Statutory Financial Data, Risk-Based Capital and Dividend Restrictions U.S. state insurance laws and regulations prescribe accounting practices for determining statutory net income and capital and surplus for insurance companies. In addition, state regulators may permit statutory accounting practices that differ from prescribed practices. Statutory accounting practices prescribed or permitted by regulatory authorities for the Company’s Insurance Company Subsidiaries differ from GAAP. The principal differences between statutory accounting practices ("SAP") and GAAP as they relate to the financial statements of the Company’s Insurance Company Subsidiaries are (i) policy acquisition costs are expensed as incurred under SAP, whereas they are deferred and amortized under GAAP, (ii) deferred tax assets are subject to more limitations regarding what amounts can be recorded under SAP and (iii) bonds are recorded at amortized cost under SAP and fair value under GAAP. Risk-Based Capital ("RBC") requirements as promulgated by the National Association of Insurance Commissioners (‘‘NAIC’’) require property and casualty insurers to maintain minimum capitalization levels determined based on formulas incorporating various business risks (e.g., investment risk, underwriting profitability, etc.) of the Insurance Company Subsidiaries. As of December 31, 2022, 2021 and 2020, the Insurance Company Subsidiaries’ adjusted capital and surplus exceeded their authorized control level as determined by the NAIC’s risk-based capital models. Summarized 2022, 2021 and 2020 statutory basis information for the non-captive Insurance Company Subsidiaries, which differs from generally accepted accounting principles, is as follows (dollars in thousands). CIC WPIC 2022 Statutory capital and surplus $ 47,827 $ 20,651 RBC authorized control level 15,541 5,098 Statutory net income (loss) ( 6,846 ) ( 4,171 ) RBC % 308 % 405 % CIC WPIC 2021 Statutory capital and surplus $ 50,194 $ 23,603 RBC authorized control level 15,868 5,331 Statutory net income (loss) ( 9,161 ) ( 614 ) RBC % 316 % 443 % CIC WPIC 2020 Statutory capital and surplus $ 49,271 $ 24,723 RBC authorized control level 14,221 4,547 Statutory net income (loss) 2,059 1,024 RBC % 346 % 544 % Dividend Restrictions The state insurance statutes in which the Insurance Company Subsidiaries are domiciled limit the amount of dividends that they may pay annually without first obtaining regulatory approval. Generally, the limitations are based on the greater of statutory net income for the preceding year or 10 % of statutory surplus at the end of the preceding year. The Insurance Company Subsidiaries must receive regulatory approval in order to pay dividends to the Parent Company from its Insurance Company Subsidiaries.

Shareholders' Equity

Shareholders' Equity	12 Months Ended
	Dec. 31, 2022
Stockholders' Equity Note [Abstract]
Shareholders' Equity	12. Shareholders’ Equity Common Stock On August 10, 2022, the Company issued $ 5.0 million of common equity through a private placement of 2,500,000 shares priced at $ 2.00 per share. The participants in the private placement consisted of members of the Company's Board of Directors. The Company used the proceeds for growth capital in the Company's specialty core business segments. For the year ended December 31, 2022 , the Company repurchased 1,968 shares of stock valued at approximately $ 4,000 related to the vesting of the Company’s restricted stock units. The Company's additional paid-in capital relating to the Company's stock repurchases was $ 10,000 for the year ended December 31, 2022. The capital increase was due to a $ 14,000 adjustment for cash returned related to the Company's stock repurchase program. For the year ended December 31, 2021 , the Company repurchased 3,886 shares of stock valued at approximately $ 12,000 related to the vesting of the Company’s restricted stock units. Upon the repurchase of the Company’s shares, the shares remain authorized, but not issued or outstanding. As of December 31, 2022 and 2021 , the Company had 12,215,849 and 9,707,817 issued and outstanding shares of common stock, respectively. Holders of common stock are entitled to one vote per share and to receive dividends only when and if declared by the board of directors. The holders have no preemptive, conversion or subscription rights.

Accumulated Other Comprehensive

Accumulated Other Comprehensive Income (Loss)	12 Months Ended
	Dec. 31, 2022
Equity [Abstract]
Accumulated Other Comprehensive Income (Loss)	13. Accumulated Other Comprehensive Income (Loss) The following table presents changes in accumulated other comprehensive income (loss) for unrealized gains and losses on available-for-sale securities (dollars in thousands): Year Ended 2022 2021 Balance at beginning of period $ ( 2,110 ) $ 912 Other comprehensive income (loss) before reclassifications ( 16,024 ) ( 2,937 ) Less: amounts reclassified from accumulated other comprehensive income (loss) 69 85 Net current period other comprehensive income (loss) ( 16,093 ) ( 3,022 ) Balance at end of period $ ( 18,203 ) $ ( 2,110 )

Earnings Per Share

Earnings Per Share	12 Months Ended
	Dec. 31, 2022
Earnings Per Share [Abstract]
Earnings Per Share	14. Earnings Per Share Basic and diluted earnings (loss) per share are computed by dividing net income by the weighted average number of common shares outstanding during the period. The following table presents the calculation of basic and diluted earnings (loss) per common share, as follows (dollars in thousands, except share and per share amounts): Year Ended 2022 2021 2020 Net income (loss) $ ( 10,681 ) $ ( 1,094 ) $ 595 Weighted average common shares, basic and diluted* 10,692,090 9,691,998 9,625,059 Earnings (loss) per share, basic and diluted ( 1.00 ) $ ( 0.11 ) $ 0.06 * The non-vested shares of the restricted stock units and stock options were anti-dilutive as of December 31, 2022, 2021, and 2020. Therefore, the non-vested shares are excluded from earnings (loss) per share for the years ended December 31, 2022, 2021, and 2020 .

Stock-based Compensation

Stock-based Compensation	12 Months Ended
	Dec. 31, 2022
Share-Based Payment Arrangement [Abstract]
Stock-based Compensation	15. Stock-based Compensation On March 8, 2022 the Company issued options to purchase 630,000 shares of the Company's common stock to two named executive officers. The right to exercise the options will vest over a five-year period on a straight-line basis. The options have a strike price of $ 4.53 per share and will expire on March 8, 2032 . The estimated fair value of these options is $ 612,000 , which is being expensed ratably over the vesting period. A Black Scholes model was used to determine the fair value of the options at the time the options were issued, using the Company’s historical 5-year market price of its stock to determine volatility (equating to 65.04 %), an estimated 5-year term to exercise the options, a 5-year risk-free rate of return of 1.8 %, and the market price for the Company’s stock of $ 2.40 per share. On June 30, 2020, the Company issued options to purchase 280,000 shares of the Company’s common stock to certain executive officers and other employees. The right to exercise the options will vest over a five-year period on a straight-line basis. The options have a strike price of $ 3.81 per share and expire on June 30, 2030 . The estimated value of these options is $ 290,000 , which will be expensed ratably over the vesting period. In 2016 and 2018, the Company issued 111,281 and 70,000 , respectively, of restricted stock units (“RSUs”) to various employees to be settled in shares of common stock, which were valued at $ 909,000 , and $ 404,000 , respectively, on the dates of grant. The Company recorded $ 56,000 , $ 166,000 , and $ 677,000 of compensation expense related to the RSUs for the years ended December 31, 2022, 2021, and 2020 , respectively. There were 9,000 unvested RSUs as of December 31, 2022 , which will generate an estimated future expense of $ 17,000 . The Company recorded $ 53,000 , $ 52,000 , and $ 29,000 of compensation expense for the year ended December 31, 2022, 2021, and 2020 , respectively, related to the stock options granted on June 30, 2020. There were 153,000 options outstanding and unvested as of December 31, 2022 , which will generate an estimated future expense of $ 132,000 . The Company recorded $ 102,000 of compensation expense for the year ended December 31, 2022 , related to the stock options granted on March 8, 2022. There were 630,000 options outstanding and unvested as of December 31, 2022 , which will generate an estimated future expense of $ 510,000 .

Related Party Transactions

Related Party Transactions	12 Months Ended
	Dec. 31, 2022
Related Party Transactions [Abstract]
Related Party Transactions	16. Related Party Transactions The Company employs Nicholas J. Petcoff as its Co-Chief Executive Officer and a Director of the Company's Board of Directors. The Company employed Andrew D. Petcoff as its Senior Vice President of Personal Lines and as President of Sycamore, until June 30, 2021. The Company’s employment of Andrew D. Petcoff ended as the result of the Venture Transaction. See Note 3 ~ Sale of Certain Agency Business for additional details. Andrew D. Petcoff resigned from the Company's Board of Directors on December 31, 2022. Andrew D. Petcoff is now the President of Sycamore Specialty Underwriters, LLC ("SSU"), a related Affiliate to the Company as of December 31, 2022. See Note 2 ~ VSRM Transaction for additional details. Nicholas J. Petcoff has been employed with the Company since 2009. Andrew D. Petcoff had formerly been employed with the Company since 2009. They are the sons of the Company's Executive Chairman and Co-Chief Executive Officer, James G. Petcoff. The Company employed B. Matthew Petcoff as Vice President of Sycamore until June 30, 2021. B. Matthew Petcoff is the brother of the Executive Chairman and Co-Chief Executive Officer, James G. Petcoff. The Company also employed Hilary Petcoff as its Vice President of Enterprise Risk Management until June 30, 2021. Ms. Petcoff is the daughter of the Company’s Executive Chairman and Co-Chief Executive Officer, James G. Petcoff. As a result of the transaction in Note 2 ~ VSRM Transaction , B. Matthew Petcoff and Hilary Petcoff are no longer employees of Venture Agency Holdings, Inc., and are no longer affiliated with the Company as of December 31, 2022. In October 2022, the Company acquired control over Venture (a previous equity method investee) for total consideration of $ 9.7 million as further described in Note 2 ~ VRSM Transaction. See Note 12 ~ Shareholders' Equity for stock issuance to the Company's Board.

Employee Benefit Plans

Employee Benefit Plans	12 Months Ended
	Dec. 31, 2022
Retirement Benefits [Abstract]
Employee Benefit Plans	17. Employee Benefit Plans The Company maintains a retirement savings plan under section 401(k) of the Internal Revenue Code (the “Plan”) for certain eligible employees. Eligible employees electing to participate in the 401(k) plan may defer and contribute from 1 % to 100 % of their compensation on a pre‑tax or post-tax basis, subject to statutory limits. The Company will match the employees’ contributions up to the first 4 % of their compensation. The Company’s Plan expense amounted to $ 457,000 , $ 508,000 and $ 508,000 for the years ended December 31, 2022, 2021 and 2020 , respectively.

Commitments and Contingencies

Commitments and Contingencies	12 Months Ended
	Dec. 31, 2022
Commitments and Contingencies Disclosure [Abstract]
Commitments and Contingencies	18. Commitments and Contingencies Legal proceedings The Company and its subsidiaries are subject at times to various claims, lawsuits and proceedings relating principally to alleged errors or omissions in the placement of insurance, claims administration, and other business transactions arising in the ordinary course of business. Where appropriate, the Company vigorously defends such claims, lawsuits and proceedings. Some of these claims, lawsuits and proceedings seek damages, including consequential, exemplary or punitive damages, in amounts that could, if awarded, be significant. Most of the claims, lawsuits and proceedings arising in the ordinary course of business are covered by the insurance policy at issue. We account for such activity through the establishment of unpaid losses and LAE reserves. In accordance with accounting guidance, if it is probable that a liability has been incurred as of the date of the financial statements and the amount of loss is reasonably estimable; then an accrual for the costs to resolve these claims is recorded by the Company in the accompanying consolidated balance sheets. Periodic expenses related to the defense of such claims are included in the accompanying consolidated statements of operations. On the basis of current information, the Company does not believe that there is a reasonable possibility that any material loss exceeding amounts already accrued, if any, will result from any of the claims, lawsuits and proceedings to which the Company is subject to, either individually, or in the aggregate. Commitments The Company is party to an agreement with an unaffiliated company to provide a policy administration, billing, and claims system for the Company. The scope of work and fee structure has changed over time. Currently, the agreement requires a minimum monthly payment of $ 30,000 with a fee schedule that is scalable with the premium volume, and expires on November 1, 2026.

Segment Information

Segment Information	12 Months Ended
	Dec. 31, 2022
Segment Reporting [Abstract]
Segment Information	19. Segment Information The Company is engaged in the sale of property and casualty insurance products and has organized its business model around three classes of insurance businesses: commercial lines, personal lines, and wholesale agency business. Within these three businesses, the Company offers various insurance products and insurance agency services. Such insurance businesses are engaged in underwriting and marketing insurance coverages, and administering claims processing for such policies. The Company views the commercial and personal lines segments as underwriting business (business that takes on insurance underwriting risk). The wholesale agency business provides non-risk bearing revenue through commissions and policy fees. The wholesale agency business increases the product options to the Company’s independent retail agents by offering both insurance products from the Insurance Company Subsidiaries as well as products offered by other insurers. The Company defines its operating segments as components of the business where separate financial information is available and used by the co-chief operating decision makers in deciding how to allocate resources to its segments and in assessing its performance. In assessing performance of its operating segments, the Company’s co-chief operating decision makers, the Co-Chief Executive Officers, review a number of financial measures including gross written premiums, net earned premiums, losses and LAE, net of reinsurance recoveries, and other revenue and expenses. The primary measure used for making decisions about resources to be allocated to an operating segment and assessing its performance is segment underwriting gain or loss which is defined as segment revenues, consisting of net earned premiums and other income, less segment expenses, consisting of losses and LAE, policy acquisition costs and operating expenses of the operating segments. Operating expenses primarily include compensation and related benefits for personnel, policy issuance and claims systems, rent and utilities. The Company markets, distributes and sells its insurance products through its own insurance agencies and a network of independent agents. All of the Company’s insurance activities are conducted in the United States with a concentration of activity in Michigan, Florida, Texas and California. For the years ended December 31, 2022, 2021, and 2020 , gross written premiums attributable to these four states were 54.1 %, 50.6 %, and 49.6 % respectively, of the Company’s total gross written premiums. The following table summarizes our net earned premiums: Net Earned Premium 2022 2021 2020 Commercial 84 % 89 % 92 % Personal 16 % 11 % 8 % Total 100 % 100 % 100 % The wholesale agency business sells insurance products on behalf of the Company’s commercial and personal lines businesses as well as to third-party insurers. Certain acquisition costs incurred by the commercial and personal lines businesses are reflected as commission revenue for the wholesale agency business and are eliminated in the Eliminations category. In addition to the reportable segments, the Company maintains a Corporate and Other category to reconcile segment results to the consolidated totals. The Corporate and Other category includes: (i) corporate operating expenses such as salaries and related benefits of the Company’s executive management team, some finance and information technology personnel, and other corporate headquarters expenses, (ii) interest expense on the Company’s debt obligations; (iii) depreciation and amortization on property and equipment, and (iv) all investment income activity. All investment income activity is reported within net investment income, net realized investment gains, and change in fair value of equity securities on the consolidated statements of operations. The Company’s assets on the consolidated balance sheet are not allocated to the reportable segments. The following tables present information by reportable segment (dollars in thousands): Year Ended December 31, 2022 Commercial Personal Under-writing Wholesale Agency Corp-orate Elim-inations Total Gross written premiums $ 116,868 $ 21,151 $ 138,019 $ — $ — $ — $ 138,019 Net written premiums $ 72,318 $ 18,914 $ 91,232 $ — $ — $ — $ 91,232 Net earned premiums $ 80,823 $ 15,888 $ 96,711 $ — $ — $ — $ 96,711 Other income 245 82 327 5,712 271 ( 3,542 ) 2,768 Segment revenue 81,068 15,970 97,038 5,712 271 ( 3,542 ) 99,479 Loss and loss adjustment expenses, net 70,762 10,678 81,440 — — — 81,440 Policy acquisition costs 17,682 4,604 22,286 3,653 — ( 3,760 ) 22,179 Operating expenses 13,069 1,936 15,005 2,612 1,192 ( 20 ) 18,789 Loss portfolio transfer risk fee 5,400 — — — — — 5,400 Segment expenses 106,913 17,218 118,731 6,265 1,192 ( 3,780 ) 127,808 Segment underwriting gain (loss) ( 25,845 ) ( 1,248 ) ( 21,693 ) ( 553 ) ( 921 ) 238 ( 28,329 ) Net investment income 32 3,011 3,043 Net realized investment gains (losses) ( 1,505 ) ( 1,505 ) Change in fair value of equity securities 403 403 Gain from VSRM Transaction 8,810 8,810 Other gains ( 1 ) 60 59 Interest expense ( 42 ) ( 2,929 ) ( 2,971 ) Income (loss) before income taxes $ ( 25,845 ) $ ( 1,248 ) $ ( 21,693 ) $ ( 564 ) $ 6,929 $ 238 $ ( 20,490 ) Selected Balance Sheet Data: Deferred policy acquisition costs $ 7,683 $ 2,796 $ ( 189 ) $ 10,290 Unearned premiums 56,565 11,322 67,887 Unpaid losses and loss adjustment expenses 159,558 5,981 165,539 Year Ended December 31, 2021 Commercial Personal Under-writing Wholesale Agency Corp-orate Elim-inations Total Gross written premiums $ 117,075 $ 15,020 $ 132,095 $ — $ — $ — $ 132,095 Net written premiums $ 87,307 $ 14,122 $ 101,429 $ — $ — $ — $ 101,429 Net earned premiums $ 87,759 $ 11,043 $ 98,802 $ — $ — $ — $ 98,802 Other income 215 143 358 5,848 365 ( 3,900 ) 2,671 Segment revenue 87,974 11,186 99,160 5,848 365 ( 3,900 ) 101,473 Loss and loss adjustment expenses, net 63,868 5,993 69,861 — — — 69,861 Policy acquisition costs 25,687 3,307 28,994 3,727 — ( 4,270 ) 28,451 Operating expenses 11,648 1,357 13,005 2,382 1,122 — 16,509 Segment expenses 101,203 10,657 111,860 6,109 1,122 ( 4,270 ) 114,821 Segment underwriting gain (loss) ( 13,229 ) 529 ( 12,700 ) ( 261 ) ( 757 ) $ 370 ( 13,348 ) Net investment income 1,968 1,968 Net realized investment gains 2,878 2,878 Change in fair value of equity securities ( 2,020 ) ( 2,020 ) Other gains 11,664 11,664 Interest expense ( 2,852 ) ( 2,852 ) Income (loss) before income taxes $ ( 13,229 ) $ 529 $ ( 12,700 ) $ ( 261 ) $ 10,881 $ 370 $ ( 1,710 ) Selected Balance Sheet Data: Deferred policy acquisition costs $ 10,619 $ 2,075 $ ( 427 ) $ 12,267 Unearned premiums 57,491 7,778 65,269 Unpaid losses and loss adjustment expenses 135,084 4,001 139,085 Year Ended December 31, 2020 Commercial Personal Under-writing Wholesale Agency Corp-orate Elim-inations Total Gross written premiums $ 102,763 $ 8,572 $ 111,335 $ — $ — $ — $ 111,335 Net written premiums $ 85,385 $ 7,555 $ 92,940 $ — $ — $ — $ 92,940 Net earned premiums $ 82,409 $ 6,694 $ 89,103 $ — $ — $ — $ 89,103 Other income 242 150 392 7,571 245 ( 5,593 ) 2,615 Segment revenue 82,651 6,844 89,495 7,571 245 ( 5,593 ) 91,718 Loss and loss adjustment expenses, net 53,263 2,965 56,228 — — — 56,228 Policy acquisition costs 25,051 2,044 27,095 4,938 — ( 5,928 ) 26,105 Operating expenses 12,644 1,069 13,713 3,107 1,648 — 18,468 Segment expenses 90,958 6,078 97,036 8,045 1,648 ( 5,928 ) 100,801 Segment underwriting gain (loss) ( 8,307 ) 766 ( 7,541 ) ( 474 ) ( 1,403 ) $ 335 ( 9,083 ) Net investment income 3,156 3,156 Net realized investment gains 8,126 8,126 Change in fair value of equity securities 228 228 Other gains 260 260 Interest expense ( 2,925 ) ( 2,925 ) Income (loss) before income taxes $ ( 8,307 ) $ 766 $ ( 7,541 ) $ ( 474 ) $ 7,442 $ 335 $ ( 238 ) Selected Balance Sheet Data: Deferred policy acquisition costs $ 11,858 $ 1,183 $ ( 798 ) $ 12,243 Unearned premiums 51,535 4,689 56,224 Unpaid losses and loss adjustment expenses 106,662 4,608 111,270

Schedule II - Condensed Financi

Schedule II - Condensed Financial Information of Registrant	12 Months Ended
	Dec. 31, 2022
Condensed Financial Information Disclosure [Abstract]
Schedule II - Condensed Financial Information of Registrant	Sched ule II Conifer Holdings, Inc. Condensed Financial Information of Registrant Balance Sheets – Parent Company Only (dollars in thousands) December 31, 2022 2021 Assets Investment in subsidiaries $ 56,670 $ 79,511 Cash 9,022 750 Due from subsidiaries ( 9,754 ) ( 7,055 ) Due from Affiliate 113 220 Other assets 2,434 2,522 Total assets $ 58,485 $ 75,948 Liabilities and Shareholders' Equity Liabilities: Debt $ 33,876 $ 33,564 Other liabilities 5,659 1,881 Total liabilities 39,535 35,445 Shareholders' equity: Common stock, no par value ( 100,000,000 shares authorized; 12,215,849 9,707,817 issued and outstanding, respectively) 97,913 92,692 Accumulated deficit ( 60,760 ) ( 50,079 ) Accumulated other comprehensive income (loss) ( 18,203 ) ( 2,110 ) Total shareholders' equity 18,950 40,503 Total liabilities and shareholders' equity $ 58,485 $ 75,948 The accompanying notes are an integral part of the Condensed Financial Information of Registrant. Schedule II Conifer Holdings, Inc. Condensed Financial Information of Registrant Statements of Comprehensive Income (Loss) – Parent Company Only (dollars in thousands) Year Ended December 31, 2022 2021 2020 Revenue Management fees from subsidiaries $ 4,980 $ 15,952 $ 12,527 Other income 190 2,900 483 Total revenue 5,170 18,852 13,010 Expenses Operating expenses 14,365 12,736 14,459 Interest expense 2,816 2,852 2,925 Total expenses 17,181 15,588 17,384 Income (loss) before equity in earnings (losses) of subsidiaries and income tax expense (benefit) ( 12,011 ) 3,264 ( 4,374 ) Income tax expense (benefit) ( 4,078 ) 156 ( 813 ) Income (loss) before equity earnings (losses) of subsidiaries ( 7,933 ) 3,108 ( 3,561 ) Equity earnings (losses) in subsidiaries ( 2,748 ) ( 4,202 ) 4,156 Net income (loss) ( 10,681 ) ( 1,094 ) 595 Other Comprehensive Income Equity in other comprehensive income (loss) of subsidiaries ( 16,093 ) ( 3,022 ) 423 Total Comprehensive income (loss) $ ( 26,774 ) $ ( 4,116 ) $ 1,018 The accompanying notes are an integral part of the Condensed Financial Information of Registrant. Schedule II Conifer Holdings, Inc. Condensed Financial Information of Registrant Statement of Cash Flows – Parent Company Only (dollars in thousands) Year Ended December 31, 2022 2021 2020 Cash Flows from Operating Activities Net income (loss) $ ( 10,681 ) $ ( 1,094 ) $ 595 Adjustments to reconcile net income (loss) to net cash used in Depreciation and amortization 436 415 421 Equity in undistributed (income) loss of subsidiaries 2,748 4,202 ( 4,156 ) Stock-based compensation expense 211 218 706 Deferred income tax expense 3,884 — — Other (gain) loss — ( 2,593 ) ( 260 ) Changes in operating assets and liabilities: Due from subsidiaries 2,699 8,800 ( 852 ) Due from Affiliate 107 ( 220 ) 214 Current income tax recoverable — — 539 Other assets 62 890 625 Other liabilities ( 203 ) ( 915 ) ( 715 ) Net cash provided by (used in) operating activities ( 737 ) 9,703 ( 2,883 ) Cash Flows From Investing Activities Contributions to subsidiaries 4,000 ( 5,400 ) ( 1,150 ) Dividends received from subsidiaries — — — Purchases of investments — — ( 79 ) Purchases of property and equipment — ( 20 ) — Net cash provided by (used in) investing activities 4,000 ( 5,420 ) ( 1,229 ) Cash Flows From Financing Activities Proceeds received from issuance of shares of common stock 5,000 — — Repurchase of common stock 10 ( 12 ) ( 36 ) Borrowings under debt arrangements 5,000 3,000 5,745 Repayment of borrowings under debt arrangements ( 5,000 ) ( 8,000 ) ( 625 ) Stock and debt issuance costs — — — Net cash provided by financing activities 5,010 ( 5,012 ) 5,084 Net increase (decrease) in cash 8,273 ( 729 ) 972 Cash at beginning of period 749 1,478 506 Cash at end of period $ 9,022 $ 749 $ 1,478 Supplemental Disclosure of Cash Flow Information: Interest paid $ 2,979 $ 2,883 $ 2,586 The accompanying notes are an integral part of the Condensed Financial Information of Registrant. 1. Accounting Policies Organization Conifer Holdings, Inc. (the “Parent”) is a Michigan‑domiciled holding company organized for the purpose of managing its insurance entities. The Parent conducts its principal operations through these entities. Basis of Presentation The accompanying condensed financial information should be read in conjunction with the Consolidated Financial Statements and related Notes of Conifer Holdings, Inc. and Subsidiaries. Investments in subsidiaries are accounted for using the equity method. Under the equity method, the investment in subsidiaries is stated at cost plus contributions and equity in undistributed income (loss) of consolidated subsidiaries less dividends received since the date of acquisition. The Parent’s operations consist of income earned from management and administrative services performed for the insurance entities pursuant to intercompany services agreements. These management and administrative services include providing management, marketing, offices and equipment, and premium collection, for which the insurance companies pay fees based on a percentage of gross premiums written. Also, the Parent receives commission income for performing agency services. The primary operating costs of the Parent are salaries and related costs of personnel, information technology, administrative expenses, and professional fees. The income received from the management and administrative services is used to cover operating costs, meet debt service requirements and cover other holding company obligations. Estimates and Assumptions Preparation of the condensed financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the amounts reported in the condensed financial statements and accompanying disclosures. Those estimates are inherently subject to change, and actual results may ultimately differ from those estimates. Dividends The Parent received a $ 10.8 million dividend from Sycamore during the fourth quarter of 2022. The Parent received no cash dividends from its subsidiaries in 2021 and 2020. In 2021, the Parent received a $ 6.0 million non-cash dividend from one of its subsidiaries in the form of a promissory note from Affiliate, which the Parent subsequently contributed to one of the insurance subsidiaries. 2. Guarantees The Parent has guaranteed the principal and interest obligations of a $ 10.0 million surplus note issued by Conifer Insurance Company to White Pine Insurance Company (both wholly owned subsidiaries). The note pays interest annually at a per annum rate of 4 % and has no maturity.

Schedule V - Valuation and Qual

Schedule V - Valuation and Qualifying Accounts	12 Months Ended
	Dec. 31, 2022
SEC Schedule, 12-09, Valuation and Qualifying Accounts [Abstract]
Schedule V - Valuation and Qualifying Accounts	Balance at Charged to Decrease to Deductions from Balance at Valuation for Deferred Tax Assets 2022 14,594 3,715 3,354 — 21,663 2021 13,292 676 626 — 14,594 2020 13,572 ( 205 ) ( 75 ) — 13,292

Summary of Significant Accoun_2

Summary of Significant Accounting Policies (Policies)	12 Months Ended
	Dec. 31, 2022
Accounting Policies [Abstract]
Basis of Presentation and Management Representation	Recent Developments COVID-19 (the “Pandemic”) continues to cause significant disruption to public health, the global economy, financial markets, and commercial, social and community activity in general. As there has been a significant reduction in reported cases and correspondingly a reduction in government restrictions, we see reduced risk to our business. We continue to monitor potential risks the Pandemic may present including a potential resurgence. Our exposure to the Pandemic is manifold. The majority of our employees continue to work remotely however strict “shelter-in-place” or “stay-at-home” orders have been lifted. A significant portion of our revenues are generated from the hospitality sector within the U.S. which remains under stress due to the threats of resurgence and resource shortages that resulted from the Pandemic. We have continued to provide customer service, process new and renewal business, handle claims and otherwise manage all operations even though the vast majority of the staff is working remotely. To date, we have not seen a major disruption in our business as a result of the Pandemic and currently do not expect to see a material negative impact to our financial position or results of operations as a result of the Pandemic. Basis of Presentation and Management Representation The consolidated financial statements include accounts, after elimination of intercompany accounts and transactions, of Conifer Holdings, Inc. (the “Company” or “Conifer”), its wholly owned subsidiaries Conifer Insurance Company ("CIC"), Red Cedar Insurance Company ("RCIC"), White Pine Insurance Company ("WPIC"), Sycamore Insurance Agency, Inc. ("Sycamore"), and, as of October 13, 2022, VSRM, Inc. ("VSRM"). VSRM has substantially no operations following the contribution to SSU as described in Note 2 ~ VSRM Transaction . CIC, WPIC, and RCIC are collectively referred to as the "Insurance Company Subsidiaries." On a stand-alone basis Conifer Holdings, Inc. is referred to as the "Parent Company." The accompanying consolidated financial statements have been prepared in conformity with accounting principles generally accepted in the United States of America (“GAAP”), which differ from statutory accounting practices prescribed or permitted for insurance companies by regulatory authorities.
Business	Business The Company is engaged in the sale of property and casualty insurance products and has organized its principal operations into three types of insurance businesses: commercial lines, personal lines, and agency business. The Company underwrites a variety of specialty insurance products, including property, general liability, liquor liability, automobile, and homeowners and dwelling policies. The Company markets and sells its insurance products through a network of independent agents, including managing general agents, whereby policies are written in all 50 states in the United States (“U.S.”). The Company’s corporate headquarters are located in Troy, Michigan with additional office facilities in Florida and Michigan.
Use of Estimates	Use of Estimates The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities at the date of the financial statements and the reported amounts of revenues and expenses during the reporting period. In applying these estimates, management makes subjective and complex judgments that frequently require assumptions about matters that are inherently uncertain, including uncertainties associated with the Pandemic. While management believes the amounts included in the consolidated financial statements reflect management's best estimates and assumptions, actual results may differ from these estimates.
Cash, Cash Equivalents, and Short-term Investments	Cash, Cash Equivalents, and Short-term Investments Cash consists of cash deposits in banks, generally in operating accounts. Cash equivalents consist of money-market funds that are specifically used as overnight investments tied to cash deposit accounts. Short-term investments, consisting of money-market funds, are classified as short-term investments in the consolidated balance sheets as they relate to the Company’s investment activities.
Lease Accounting	Lease Accounting The Company accounts for leases under FASB Accounting Standards Update ("ASU") No. 2016-02, Leases (Topic 842), which required the recognition of a right-of-use asset and a corresponding lease liability, discounted to the present value upon initial recognition, for all leases that extend beyond 12 months. For operating leases, the asset and liability are amortized over the lease term with expense recognized on a straight-line basis and all cash flows included in the operating section of the consolidated statement of cash flows. We do not have any financing leases. Our operating leases consist primarily of real estate utilized in the operation of our businesses with lease terms ranging from 5 to 10 years . Management has determined the appropriate discount rate to use in calculating the right-to-use asset and lease liability is 6.75 %. The Company records a right-of-use asset and lease liabilities included in Other Assets and Other Liabilities in the Consolidated Balance Sheets. As of December 31, 2022, the Company had a right-of-use asset of $ 1.3 million, and lease liabilities of $ 1.3 million. As of December 31, 2021, the Company had a right-of-use asset of $ 1.4 million, and lease liabilities of $ 1.5 million.
Investment Securities and Other-than-temporary Impairments	Investment Securities Debt securities are classified as available-for-sale and reported at fair value. The Company determines the fair value using the market approach, which uses quoted prices or other relevant data based on market transactions involving identical or comparable assets. The Company purchases available-for-sale debt securities with the expectation that they will be held to maturity, however the Company may sell them if market conditions or credit‑related risk warrant earlier sales. The Company does not have any securities classified as held-to-maturity or trading. The change in unrealized gain and loss on debt securities is recorded as a component of accumulated other comprehensive income (loss), net of the related deferred tax effect, until realized. The debt securities portfolio includes structured securities. The Company recognizes income from these securities using a constant effective yield based on anticipated prepayments and the estimated economic life of the securities. When actual prepayments differ significantly from anticipated prepayments, the estimated economic life is recalculated and the remaining unamortized premium or discount is amortized prospectively over the remaining economic life. Premiums and discounts on structured securities are amortized or accreted over the life of the related available‑for‑sale security as an adjustment to yield using the effective interest method. Such amortization and accretion is included in interest income in the consolidated statements of operations. Dividend and interest income are recognized when earned. Realized gains and losses from the sale of available-for-sale securities are determined on a specific-identification basis and included in earnings on the trade date. Equity securities that do not result in consolidation and are not accounted for under the equity method are measured at fair value and any changes in fair value are recognized in net income in the Consolidated Statements of Operations. Investment company limited partnerships are measured at their net asset value, which approximates fair value. Any changes in the net asset value are recognized in net income in the Consolidated Statements of Operations. The Company carries other equity investments that do not have a readily determinable fair value at cost, less impairment and adjusted for observable price changes under the measurement alternative provided under GAAP. We review these investments for impairment during each reporting period. These investments are a component of Other Assets in the Consolidated Balance Sheets. Other-than-Temporary Impairments The Company reviews its impaired securities for possible other-than-temporary impairment ("OTTI") at each quarter-end. A security has an impairment loss when its fair value is less than its cost or amortized cost at the balance sheet date. The Company considers the following factors in performing its review: (i) the amount by which the security’s fair value is less than its cost, (ii) length of time the security has been impaired, (iii) whether management has the intent to sell the security, (iv) if it is more likely than not that management will be required to sell the security before recovery of its amortized cost basis, (v) whether the impairment is due to an issuer‑specific event, credit issues or change in market interest rates, (vi) the security’s credit rating and any recent downgrades or (vii) stress testing of expected cash flows under different scenarios. If the Company cannot conclude that declines in fair value below amortized cost are considered temporary, an OTTI loss is recorded through the Consolidated Statements of Operations in the current period. For all other impaired securities, the Company will assess whether the net present value of the cash flows expected to be collected from the security is less than its amortized cost basis. Such a shortfall in cash flows is referred to as a “credit loss.” For any such security, the Company separates the impairment loss into: (i) the credit loss and (ii) the non-credit loss, which is the amount related to all other factors such as interest rate changes, fluctuations in exchange rates and market conditions. The credit loss charge is recorded to the current period statements of operations and the non-credit loss is recorded to accumulated other comprehensive income (loss), within shareholders’ equity, on an after-tax basis. A security’s cost basis is permanently reduced by the amount of a credit loss. Income is accreted over the remaining life of a security based on the interest rate necessary to discount the expected future cash flows to the new basis. If the security is non-income producing, any cash proceeds are applied as a reduction of principal when received.
Recognition of Premium Revenues	Recognition of Premium Revenues All of the property and casualty policies written by our insurance companies are considered short-duration contracts. These policy premiums are earned on a daily pro-rata basis, net of reinsurance, over the term of the policy, which are primarily twelve months in duration. The portion of premiums written that relate to the unexpired terms of policies in force are deferred and reported as unearned premium at the balance sheet date.
Reinsurance	Reinsurance Reinsurance premiums, commissions, losses and loss adjustment expenses ("LAE") on reinsured business are accounted for on a basis consistent with that used in accounting for the original policies issued and the terms of the reinsurance contracts. The amounts reported as reinsurance recoverables include amounts billed to reinsurers on losses and LAE paid as well as estimates of amounts expected to be recovered from reinsurers on insurance liabilities that have not yet been paid. Reinsurance recoverables on unpaid losses and LAE are estimated based upon assumptions consistent with those used in establishing the gross liabilities as they are applied to the underlying reinsured contracts. The Company records an allowance for uncollectible reinsurance recoverables based on an assessment of the reinsurer’s creditworthiness and collectability of the recorded amounts. Management believes an allowance for uncollectible recoverables from its reinsurers was not necessary for the periods presented. The Company receives ceding commissions in connection with certain ceded reinsurance. The ceding commissions are recorded as a reduction of policy acquisition costs. In 2022, the Company entered into a loss portfolio transfer ("LPT") reinsurance agreement. The LPT is a retroactive reinsurance contract. See Note 8 ~ Reinsurance for further details regarding the LPT.
Deferred Policy Acquisition Costs	Deferred Policy Acquisition Costs Costs incurred which are incremental and directly related to the successful acquisition of new or renewal insurance business is deferred. These deferred costs consist of commissions paid to agents (net of ceding commissions), premium taxes, and underwriting costs, including compensation and payroll related benefits. Proceeds from reinsurance transactions that represent recovery of acquisition costs reduce applicable unamortized acquisition costs in such a manner that net acquisition costs are capitalized and charged to expense. Amortization of such policy acquisition costs is charged to expense in proportion to premium earned over the estimated policy term. To the extent that unearned premiums on existing policies are not adequate to cover the sum of expected losses and LAE, unamortized acquisition costs and policy maintenance costs, unamortized deferred policy acquisition costs are charged to expense to the extent required to eliminate the premium deficiency. If the premium deficiency is greater than the unamortized policy acquisition costs, a liability is recorded for any such deficiency. As of December 31, 2022, there was no premium deficiency reserve. The Company considers anticipated investment income in determining whether a premium deficiency exists. Management performs this evaluation at each insurance product line level.
Unpaid Losses and Loss Adjustment Expenses	Unpaid Losses and Loss Adjustment Expenses The liability for unpaid losses and LAE in the Consolidated Balance Sheets represents the Company’s estimate of the amount it expects to pay for the ultimate cost of all losses and LAE incurred that remain unpaid at the balance sheet date. The liability is recorded on an undiscounted basis, except for the liability for unpaid losses and LAE assumed related to any acquired companies which are initially recorded at fair value. The process of estimating the liability for unpaid losses and LAE is a complex process that requires a high degree of judgment. The liability for unpaid losses and LAE represents the accumulation of individual case estimates for reported losses and LAE, and actuarially determined estimates for incurred but not reported losses and LAE and includes a provision for estimated costs to settle all outstanding claims at the balance sheet date. The liability for unpaid losses and LAE is intended to include the ultimate net cost of all losses and LAE incurred but unpaid as of the balance sheet date. The liability is stated net of anticipated deductibles, salvage and subrogation, and gross of reinsurance ceded. The estimate of the unpaid losses and LAE liability is continually reviewed and updated. Although management believes the liability for losses and LAE is reasonable, the ultimate liability may be more or less than the current estimate. The estimation of ultimate liability for unpaid losses and LAE is a complex, imprecise and inherently uncertain process, and therefore involves a considerable degree of judgment and expertise. The Company utilizes various actuarially‑accepted reserving methodologies in deriving the continuum of expected outcomes and ultimately determining its estimated liability amount. These methodologies utilize various inputs, including but not limited to written and earned premiums, paid and reported losses and LAE, expected initial loss and LAE ratio, which is the ratio of incurred losses and LAE to earned premiums, and expected claim reporting and payout patterns (including company-specific and industry data). The liability for unpaid loss and LAE does not represent an exact measurement of liability, but is an estimate that is not directly or precisely quantifiable, particularly on a prospective basis, and is subject to a significant degree of variability over time. In addition, the establishment of the liability for unpaid losses and LAE makes no provision for the broadening of coverage by legislative action or judicial interpretation or for the extraordinary future emergence of new types of losses not sufficiently represented in the Company’s historical experience or which cannot yet be quantified. As a result, an integral component of estimating the liability for unpaid losses and LAE is the use of informed subjective estimates and judgments about the ultimate exposure to unpaid losses and LAE. The effects of changes in the estimated liability are included in the results of operations in the period in which the estimates are revised. The Company allocates the applicable portion of the unpaid losses and LAE to amounts recoverable from reinsurers under reinsurance contracts and reports those amounts separately as assets on the consolidated balance sheets.
Income Taxes	Income Taxes Income taxes are accounted for under the asset and liability method. Deferred tax assets and liabilities are recognized for the future tax consequences attributable to differences between the financial statement carrying amounts of existing assets and liabilities and their respective tax bases and operating loss and tax-credit carryforwards. Deferred tax assets and liabilities are measured using enacted tax rates expected to apply to taxable income in the years in which those temporary differences are expected to be recovered or settled. The effect on deferred tax assets and liabilities of a change in tax rates is recognized in income in the period that includes the enactment date. Deferred tax assets are recognized to the extent that there is sufficient positive evidence, as allowed under the Accounting Standard Codification ("ASC") 740, Income Taxes, to support the recoverability of those deferred tax assets. The Company establishes a valuation allowance to the extent that there is insufficient evidence to support the recoverability of the deferred tax asset under ASC 740. In making such a determination, management considers all available positive and negative evidence, including future reversals of existing taxable temporary differences, projected future taxable income, tax‑planning strategies, and results of recent operations. If it is determined that the deferred tax assets would be realizable in the future in excess of their net recorded amount, an adjustment would be made to the deferred tax asset valuation allowance, which would reduce the provision for income taxes. As of December 31, 2022 and 2021 , the Company did no t have any unrecognized tax benefits and had no accrued interest or penalties related to uncertain tax positions.
Other Income	Other Income Other income consists primarily of fees charged to policyholders by the Company for services outside of the premium charge, such as installment billings or policy issuance costs. Commission income is also received by the Company’s insurance agencies for writing policies for third party insurance companies. The Company recognizes commission income on the later of the effective date of the policy, the date when the premium can be reasonably established, or the date when substantially all services related to the insurance placement have been rendered.
Operating Expenses	Operating Expenses Operating expenses consist primarily of other underwriting, compensation and benefits, information technology, facility and other administrative expenses.
Accounting Guidance Not Yet Adopted	Accounting Guidance Not Yet Adopted In June 2016, the FASB issued ASU No. 2016-13, Financial Instruments - Credit Losses (Topic 326), which amends the current methodology and timing for recognizing credit losses. This amendment will replace the current GAAP "incurred loss" methodology for credit losses with a methodology based on expected credit losses. The new guidance will also require expanded consideration of a broader range of reasonable and increased supportable information for the credit loss estimates. This ASU is effective for annual and interim reporting periods beginning after December 15, 2022. Management does not expect the new guidance to have a material impact on the Company's consolidated financial statements. In January 2021, the FASB issued ASU 2022-06, Reference Rate Reform (Topic 848) . This guidance provides optional expedients and exceptions that are intended to ease the burden of updating contracts to contain a new reference rate due to the discontinuation of the London Inter-Bank Offered Rate (LIBOR). This guidance is available immediately and may be implemented in any period prior to the guidance expiration on December 31, 2024. Management does not expect the new guidance to have a material impact on the Company’s consolidated financial statements.
Risks and Uncertainties	Risks and Uncertainties The Company is exposed to interest rate risks as it maintains a significant amount of its investment portfolio in debt securities. As a result of changes in interest rates during 2022, the Company reported a $ 16.0 million net unrealized loss that was reflected in other comprehensive income. As of December 31, 2022, total net unrealized losses in the debt securities was $ 18.2 million. Management believes it will not need to sell debt securities at significant losses as it has the ability and intention to hold them until their values improve. Management has noted the media has reported a number of recent bank failures. The Company does not have any deposits or investments in any of these banks. Management does not expect any significant impact as a result of these events.

VSRM Transaction (Tables)

VSRM Transaction (Tables)	12 Months Ended
	Dec. 31, 2022
Business Combinations [Abstract]
Schedule of Condensed Assets and Liabilities Incorporated Into Consolidated Balance Sheet from VSRM Acquisition	A condensed schedule of assets and liabilities incorporated into the consolidated balance sheet from the VSRM acquisition is provided below: Cash $ 3,921 Trade receivables 4,604 Customer relationship intangible assets 37,122 Other assets 574 Total assets $ 46,221 Trade and other payables 7,624 Deferred tax liability 9,407 Note payable to Affiliate 6,000 Senior debt 2,917 Total Liabilities $ 25,948 Fair value of net assets acquired $ 20,273
Schedule of Calculation of Revaluation Gain Related to Company's Equity Method Investment in VSRM as a Result of VSRM Transaction	The following table presents the calculation of the $ 8.8 million revaluation gain related to the Company's equity method investment in VSRM as a result of the VSRM Transaction: Carrying value of equity method investment in VSRM $ 1,773 Fair value of investment in VSRM 10,583 Gain on step acquisition $ 8,810
Schedule of Reconciles the Net Assets Disposed	The following table reconciles the net assets disposed of from this transaction: Cash at closing $ 32,759 Net liabilities transferred 1,499 Hold back 75 Stock of acquirer 3,822 Total purchase price $ 38,155 Cash $ 271 Premiums transferred to buyer 4,326 Intangible assets 38,154 Trade payables and accrued liabilities assumed by buyer ( 5,838 ) Net assets disposed of 36,913 Net gain 1,242 Broker fee transaction costs ( 1,242 ) Net gain $ — The net gain on revaluation of the investment in VSRM and the disposal of the Security and Alarm Business line are summarized below: Gross gains $ 10,052 Broker fee ( 1,242 ) Net gain $ 8,810
Schedule of Assets And Liabilites Deconsolidated as a Result of This Transaction	The following table provides the assets and liabilities deconsolidated as a result of this transaction: Cash $ 497 Receivable from VSRM 934 Trade receivables 239 Intangible asset 196 Other assets 514 Total assets $ 2,380 Payable to Affiliates 286 Trade payables 193 Note payable 1,000 Other liabilities 901 Total Liabilities $ 2,380

Investments (Tables)

Investments (Tables)	12 Months Ended
	Dec. 31, 2022
Investments, Debt and Equity Securities [Abstract]
Schedule of Available-for-sale Securities	The cost or amortized cost, gross unrealized gain or loss, and estimated fair value of the investments in securities classified as available-for-sale at December 31, 2022 and 2021 were as follows (dollars in thousands): December 31, 2022 Cost or Gross Unrealized Amortized Gains Losses Estimated Debt securities: U.S. Government $ 7,833 $ — $ ( 335 ) $ 7,498 State and local government 25,487 1 ( 4,672 ) 20,816 Corporate debt 35,347 — ( 4,788 ) 30,559 Asset-backed securities 21,742 — ( 1,246 ) 20,496 Mortgage-backed securities 29,194 — ( 5,157 ) 24,037 Commercial mortgage-backed securities 3,414 — ( 186 ) 3,228 Collateralized mortgage obligations 4,102 — ( 535 ) 3,567 Total debt securities available for sale $ 127,119 $ 1 $ ( 16,919 ) $ 110,201 December 31, 2021 Cost or Gross Unrealized Amortized Gains Losses Estimated Debt securities: U.S. Government $ 20,723 $ 74 $ ( 77 ) $ 20,720 State and local government 30,063 555 ( 189 ) 30,429 Corporate debt 30,808 88 ( 550 ) 30,346 Asset-backed securities 28,652 10 ( 224 ) 28,438 Mortgage-backed securities 33,178 105 ( 762 ) 32,521 Commercial mortgage-backed securities 1,659 31 — 1,690 Collateralized mortgage obligations 5,649 35 ( 45 ) 5,639 Total debt securities available for sale $ 150,732 $ 898 $ ( 1,847 ) $ 149,783
Schedule Of Unrealized Loss On Investments	The following table summarizes the aggregate fair value and gross unrealized losses, by security type, of the available-for-sale securities in unrealized loss positions. The table segregates the holdings based on the length of time that individual securities have been in a continuous unrealized loss position (dollars in thousands): December 31, 2022 Less than 12 months 12 months or More Total No. Fair Value of Gross No. Fair Value of Gross No. Fair Value of Gross Debt securities: U.S. Government 8 $ 3,534 $ ( 135 ) 5 $ 3,964 $ ( 200 ) 13 $ 7,498 $ ( 335 ) State and local government 77 12,966 ( 2,318 ) 45 7,147 ( 2,354 ) 122 20,113 ( 4,672 ) Corporate debt 27 10,069 ( 1,373 ) 42 20,890 ( 3,415 ) 69 30,959 ( 4,788 ) Asset-backed securities 6 3,188 ( 76 ) 20 17,308 ( 1,170 ) 26 20,496 ( 1,246 ) Mortgage-backed securities 57 4,006 ( 573 ) 12 20,031 ( 4,584 ) 69 24,037 ( 5,157 ) Commercial mortgage 4 3,205 ( 186 ) - - - 4 3,205 ( 186 ) Collateralized mortgage 26 1,789 ( 196 ) 9 1,802 ( 339 ) 35 3,591 ( 535 ) Total debt securities 205 38,757 ( 4,857 ) 133 71,142 ( 12,062 ) 338 109,899 ( 16,919 ) December 31, 2021 Less than 12 months 12 months or More Total No. Fair Value of Gross No. Fair Value of Gross No. Fair Value of Gross Debt securities: U.S. Government 6 $ 10,323 $ ( 47 ) 1 $ 4,728 $ ( 30 ) 7 $ 15,051 $ ( 77 ) State and local government 41 8,875 ( 172 ) 4 446 ( 17 ) 45 9,321 ( 189 ) Corporate debt 41 22,748 ( 505 ) 1 705 ( 45 ) 42 23,453 ( 550 ) Asset-backed securities 24 24,305 ( 219 ) 2 1,893 ( 5 ) 26 26,198 ( 224 ) Mortgage-backed securities 12 27,034 ( 762 ) — — — 12 27,034 ( 762 ) Commercial mortgage 0 — 0 — — — 0 — 0 Collateralized mortgage 10 2,638 ( 45 ) 2 29 — 12 2,667 ( 45 ) Total debt securities 134 $ 95,923 $ ( 1,750 ) 10 $ 7,801 $ ( 97 ) 144 $ 103,724 $ ( 1,847 )
Schedule of Investment Income	The Company’s sources of net investment income are as follows (dollars in thousands): December 31, 2022 2021 2020 Debt securities $ 2,517 $ 2,217 $ 3,213 Equity securities 52 194 220 Cash, cash equivalents, and short-term investments 776 2 138 Total investment income 3,345 2,413 3,571 Investment expenses ( 302 ) ( 445 ) ( 415 ) Net investment income $ 3,043 $ 1,968 $ 3,156
Schedule of Gross Realized Gains and Losses on Securities	The following table summarizes the gross realized gains and losses from sales or maturities of available-for-sale debt securities and equity securities, as follows (dollars in thousands): December 31, 2022 2021 2020 Debt securities: Gross realized gains $ 6 $ 63 $ 4,646 Gross realized losses ( 155 ) ( 6 ) ( 8 ) Total debt securities ( 149 ) 57 4,638 Equity securities: Gross realized gains 375 4,605 4,854 Gross realized losses ( 1,731 ) ( 1,784 ) ( 1,366 ) Total equity securities ( 1,356 ) 2,821 3,488 Total net realized investment gains $ ( 1,505 ) $ 2,878 $ 8,126
Summary of Amortized Cost and Fair Value of Securities	The table below summarizes the amortized cost and fair value of available-for-sale debt securities by contractual maturity at December 31, 2022. Actual maturities may differ from contractual maturities because certain borrowers have the right to call or prepay obligations with or without call or prepayment penalties (dollars in thousands): Amortized Estimated Due in one year or less $ 4,876 $ 4,770 Due after one year through five years 28,396 25,963 Due after five years through ten years 23,974 19,782 Due after ten years 11,421 8,358 Securities with contractual maturities 68,667 58,873 Asset-backed securities 21,742 20,496 Mortgage-backed securities 29,194 24,037 Commercial mortgage-backed securities 3,414 3,228 Collateralized mortgage obligations 4,102 3,567 Total debt securities $ 127,119 $ 110,201

Fair Value Measurements (Tables

Fair Value Measurements (Tables)	12 Months Ended
	Dec. 31, 2022
Fair Value Disclosures [Abstract]
Summary of Assets and Liabilities Measured at Fair Value	The following tables present the Company’s assets and liabilities measured at fair value, classified by the valuation hierarchy as of December 31, 2022 and 2021 (dollars in thousands): December 31, 2022 Fair Value Measurements Using Total Level 1 Level 2 Level 3 Assets: Debt Securities: U.S. Government $ 7,498 $ — $ 7,498 $ — State and local government 20,816 — 20,816 — Corporate debt 30,559 — 30,559 — Asset-backed securities 20,496 — 20,496 — Mortgage-backed securities 24,037 — 24,037 — Commercial mortgage-backed securities 3,228 — 3,228 — Collateralized mortgage obligations 3,567 — 3,567 — Total debt securities 110,201 — 110,201 — Equity Securities 917 160 757 — Short-term investments 25,929 25,929 — — Total marketable investments measured at fair value $ 137,047 $ 26,089 $ 110,958 $ — Investments measured at NAV: Investment in limited partnership 350 Total assets measured at fair value $ 137,397 Liabilities: Senior Unsecured Notes * $ 22,430 $ — $ 22,430 $ — Subordinated Notes * 11,300 — — 11,300 Total Liabilities (non-recurring fair value measure $ 33,730 $ — $ 22,430 $ 11,300 * Carried at face value of debt net of unamortized debt issuance costs on the consolidated balance sheet December 31, 2021 Fair Value Measurements Using Total Level 1 Level 2 Level 3 Assets: Debt Securities: U.S. Government $ 20,720 $ — $ 20,720 $ — State and local government 30,429 — 30,429 — Corporate debt 30,346 — 30,346 — Asset-backed securities 28,438 — 28,438 — Mortgage-backed securities 32,521 — 32,521 — Commercial mortgage-backed securities 1,690 — 1,690 — Collateralized mortgage obligations 5,639 — 5,639 — Total debt securities 149,783 — 149,783 — Equity Securities 9,437 9,154 283 — Short-term investments 23,013 23,013 — — Total marketable investments measured at fair value $ 182,233 $ 32,167 $ 150,066 $ — Investments measured at NAV: Investment in limited partnership 494 Total assets measured at fair value $ 182,727 Liabilities: Senior Unsecured Notes * $ 24,118 $ — $ 24,118 $ — Subordinated Notes * 11,704 — — 11,704 Total Liabilities measured at fair value $ 35,822 $ — $ 24,118 $ 11,704 * Carried at face value of debt net of unamortized debt issuance costs on the consolidated balance sheet

Deferred Policy Acquisition C_2

Deferred Policy Acquisition Costs (Tables)	12 Months Ended
	Dec. 31, 2022
Deferred Policy Acquisition Costs Disclosures [Abstract]
Summary of Deferred Policy Acquisition Costs	The activity in deferred policy acquisition costs, net of reinsurance transactions, is as follows (dollars in thousands): December 31, 2022 2021 2020 Balance at beginning of period $ 12,267 $ 12,243 $ 11,906 Deferred policy acquisition costs 20,202 28,475 26,442 Amortization of policy acquisition costs ( 22,179 ) ( 28,451 ) ( 26,105 ) Net change ( 1,977 ) 24 337 Balance at end of period $ 10,290 $ 12,267 $ 12,243

Unpaid Losses and Loss Adjust_2

Unpaid Losses and Loss Adjustment Expenses (Tables)	12 Months Ended
	Dec. 31, 2022
Insurance Loss Reserves [Abstract]
Schedule of the Changes in the Reserves for Losses and Loss Adjustment Expense	The table below provides the changes in the reserves for losses and LAE, net of recoverables from reinsurers, for the periods indicated (dollars in thousands): December 31, 2022 2021 2020 Gross reserves - beginning of period $ 139,085 $ 111,270 $ 107,246 Less: reinsurance recoverables on unpaid losses 40,344 24,218 22,579 Net reserves - beginning of period 98,741 87,052 84,667 Add: incurred losses and loss adjustment expenses, net Current period 57,156 50,429 40,634 Prior period 24,284 19,432 15,594 Total net incurred losses and loss adjustment 81,440 69,861 56,228 Deduct: loss and loss adjustment expense payments, Current period 20,894 18,984 13,599 Prior period 76,399 39,188 40,244 Total net loss and loss adjustment expense 97,293 58,172 53,843 Net reserves - end of period 82,888 98,741 87,052 Plus: reinsurance recoverables on unpaid losses 82,651 40,344 24,218 Gross reserves - end of period $ 165,539 $ 139,085 $ 111,270
Short-duration Insurance Contracts, Claims Development	The following tables represent cumulative incurred loss and allocated loss adjustment expenses ("ALAE"), net of reinsurance, by accident year and cumulative paid loss and ALAE, net of reinsurance, by accident year, for the years ended December 31, 2013 to 2022, as well as total IBNR and the cumulative number of reported claims for the year ended December 31, 2022, by reportable segment and accident year (dollars in thousands). The tables do not include reinsurance recoverables from the LPT. Commercial Lines Incurred loss and allocated loss adjustment expenses, net of reinsurance Total Cumulative Accident Year 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 2022 2022 2013 10,018 9,435 9,893 10,237 11,252 11,218 11,624 11,804 11,867 12,046 — 613 2014 19,709 19,907 22,711 26,367 28,145 28,766 29,045 29,175 29,011 — 1,754 2015 22,442 26,633 31,861 34,478 36,372 37,795 38,824 39,093 26 2,361 2016 32,396 34,935 40,440 44,355 46,089 46,993 48,677 201 3,557 2017 44,251 44,495 49,749 51,883 55,589 56,649 671 5,832 2018 42,624 42,432 49,741 55,261 60,102 1,637 6,124 2019 41,286 42,129 46,329 55,263 4,529 6,320 2020 33,867 35,328 39,193 3,787 3,830 2021 40,388 42,266 8,744 2,861 2022 41,708 16,067 1,965 Total $ 424,008 $ 35,662 Commercial lines Cumulative paid loss and allocated loss adjustment expenses, net of reinsurance Accident Year 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 2013 3,979 6,211 7,643 8,622 10,147 10,650 11,137 11,620 11,702 11,935 2014 8,715 13,977 17,458 22,446 25,609 27,544 28,389 28,648 28,608 2015 10,470 17,817 22,549 30,475 34,497 35,833 37,563 38,685 2016 10,255 19,135 27,785 37,967 41,945 43,644 46,957 2017 12,448 23,020 34,205 42,308 47,148 52,800 2018 10,375 19,799 31,633 41,577 50,508 2019 10,078 20,462 28,958 39,893 2020 10,217 17,332 24,225 2021 12,870 21,313 2022 12,839 Total $ 327,763 Net Unpaid losses and ALAE, years 2013 through 2022 $ 96,245 Unpaid losses and ALAE, prior to 2013* 177 Unpaid Losses, LPT ( 25,913 ) Unpaid losses and ALAE, net of reinsurance $ 70,509 * Presented as unaudited required supplementary information. Personal Lines Incurred loss and allocated loss adjustment expenses, net of reinsurance Total Cumulative Accident For the years ended December 31, Year 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 2022 2022 2013 18,034 17,996 18,925 19,138 19,167 19,202 19,222 19,226 19,227 19,365 — 5,208 2014 17,951 17,471 17,735 17,880 17,929 18,082 18,095 18,097 18,052 — 3,737 2015 10,877 13,445 14,721 15,285 15,364 15,427 15,427 15,448 — 2,152 2016 11,619 13,418 14,949 15,550 15,655 15,634 15,679 — 1,814 2017 14,058 13,550 14,493 14,793 14,911 14,957 — 2,917 2018 5,893 6,378 6,283 6,382 6,298 — 803 2019 3,099 2,712 2,898 2,862 — 342 2020 2,339 2,590 2,636 — 366 2021 4,409 4,332 116 580 2022 9,404 1,427 652 Total $ 109,033 $ 1,543 Personal lines Cumulative paid loss and allocated loss adjustment expenses, net of reinsurance Accident For the years ended December 31, Year 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 2013 9,955 15,883 18,052 18,600 19,014 19,174 19,214 19,222 19,227 19,365 2014 12,819 16,515 17,260 17,746 17,855 18,047 18,068 18,070 18,025 2015 7,771 11,873 13,844 15,159 15,250 15,290 15,416 15,444 2016 7,119 11,238 14,442 15,110 15,351 15,452 15,679 2017 8,320 12,944 14,004 14,526 14,866 14,957 2018 4,296 5,618 6,100 6,242 6,244 2019 2,119 2,604 2,692 2,850 2020 1,307 2,455 2,605 2021 3,022 3,980 2022 5,397 Total $ 104,546 Net Unpaid losses and ALAE, years 2013 through 2022 $ 4,487 Unpaid losses and ALAE, prior to 2013* — Unpaid losses and ALAE, net of reinsurance $ 4,487 * Presented as unaudited required supplementary information. Total Lines Incurred loss and allocated loss adjustment expenses, net of reinsurance Total Cumulative number of reported claims Accident For the years ended December 31, Year 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 2022 2022 2013 28,052 27,431 28,817 29,375 30,419 30,420 30,846 31,030 31,094 31,411 — 5,821 2014 37,660 37,378 40,446 44,247 46,074 46,848 47,140 47,272 47,063 — 5,491 2015 33,319 40,078 46,581 49,763 51,736 53,222 54,251 54,541 26 4,513 2016 44,015 48,353 55,389 59,905 61,744 62,627 64,356 201 5,371 2017 58,309 58,045 64,242 66,676 70,500 71,606 671 8,749 2018 48,517 48,810 56,024 61,643 66,400 1,637 6,927 2019 44,385 44,841 49,227 58,125 4,529 6,662 2020 36,206 37,918 41,829 3,787 4,196 2021 44,797 46,598 8,860 3,441 2022 51,112 17,494 2,617 Total 533,041 37,205 Total lines Cumulative paid loss and allocated loss adjustment expenses, net of reinsurance Accident For the years ended December 31, Year 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 2013 13,934 22,094 25,695 27,223 29,162 29,824 30,351 30,842 30,929 31,300 2014 21,534 30,492 34,718 40,192 43,464 45,591 46,457 46,718 46,633 2015 18,241 29,690 36,393 45,634 49,747 51,123 52,979 54,129 2016 17,374 30,373 42,227 53,077 57,296 59,096 62,636 2017 20,768 35,964 48,209 56,834 62,014 67,757 2018 14,671 25,417 37,733 47,819 56,752 2019 12,197 23,066 31,650 42,743 2020 11,524 19,787 26,830 2021 15,892 25,293 2022 18,236 Total $ 432,309 Net Unpaid losses and ALAE, years 2013 through 2022 $ 100,732 Unpaid losses and ALAE, prior to 2013* 177 Unpaid losses, LPT ( 25,913 ) Unpaid losses and ALAE, net of reinsurance $ 74,996 * Presented as unaudited required supplementary information.
Short-duration Insurance Contracts, Reconciliation of Loss Development to Liability	The following table reconciles the loss development information to the consolidated balance sheet for the year ended December 31, 2022, by reportable segment (dollars in thousands). December 31, Net unpaid losses claims and ALAE Commercial Lines $ 70,509 Personal Lines 4,487 Total unpaid losses and LAE, net of reinsurance 74,996 Reinsurance recoverable on losses and LAE Commercial Lines 81,301 Personal Lines 1,350 Total reinsurance recoverable on unpaid losses and LAE 82,651 ULAE expense 7,892 Total gross unpaid losses and LAE $ 165,539
Loss Duration Schedule	The following table represents the average annual percentage payout of incurred losses by age, net of reinsurance, for each reportable segment. Average annual percentage payout of incurred losses by age, net of reinsurance Year 1 Year 2 Year 3 Year 4 Year 5 Year 6 Year 7 Year 8 Year 9 Year Commercial Lines 34.4 % 23.0 % 17.7 % 10.0 % 8.0 % 3.6 % 1.8 % 0.8 % 0.4 % 0.3 % Personal Lines 69.4 % 16.6 % 10.1 % 2.6 % 0.9 % 0.2 % 0.1 % 0.1 % 0.0 % 0.0 % Total Lines 35.7 % 22.8 % 17.5 % 9.7 % 7.7 % 3.5 % 1.7 % 0.8 % 0.4 % 0.2 %

Reinsurance (Tables)

Reinsurance (Tables)	12 Months Ended
	Dec. 31, 2022
Reinsurance Disclosures [Abstract]
Summary of the Effects of Reinsurance	The following table presents the effects of reinsurance and assumption transactions on written premiums, earned premiums and losses and LAE (dollars in thousands). In 2022, ceded written and earned premium amounts included $ 1.6 million of reinsurance reinstatement costs relating to Hurricane Ian. In 2021, ceded written and earned amounts included $ 340,000 of reinsurance reinstatement costs relating to Winter Storm Uri. In 2021 and 2020, the ceded written and earned premium amounts include $ 86,000 and $ 195,000 of reinsurance reinstatement costs relating to Hurricane Irma, respectively. Year Ended December 31, 2022 2021 2020 Written premiums: Direct $ 95,832 $ 97,801 $ 82,430 Assumed 42,187 34,294 28,905 Ceded ( 46,787 ) ( 30,666 ) ( 18,395 ) Net written premiums $ 91,232 $ 101,429 $ 92,940 Earned premiums: Direct $ 97,843 $ 91,943 $ 75,130 Assumed 37,558 31,107 31,484 Ceded ( 38,690 ) ( 24,248 ) ( 17,511 ) Net earned premiums $ 96,711 $ 98,802 $ 89,103 Loss and loss adjustment expenses: Direct $ 73,000 $ 71,021 $ 48,780 Assumed 43,487 25,740 24,429 Ceded ( 35,047 ) ( 26,900 ) ( 16,981 ) Net loss and LAE $ 81,440 $ 69,861 $ 56,228

Debt (Tables)

Debt (Tables)	12 Months Ended
	Dec. 31, 2022
Debt Disclosure [Abstract]
Schedule of Outstanding Senior Debt	A summary of the Company's outstanding debt is as follows (dollars in thousands): December 31, 2022 2021 Senior unsecured notes $ 24,186 $ 23,926 Subordinated notes 9,690 9,638 Total $ 33,876 $ 33,564

Income Taxes (Tables)

Income Taxes (Tables)	12 Months Ended
	Dec. 31, 2022
Income Tax Disclosure [Abstract]
Schedule of Income Tax Expense (Benefit)	The income tax expense (benefit) is comprised of the following (dollars in thousands): Year Ended December 31, 2022 2021 2020 Current tax expense (benefit) $ ( 45 ) $ 208 $ 6 Deferred tax expense (benefit) ( 9,396 ) — — Total income tax expense (benefit) $ ( 9,441 ) $ 208 $ 6
Summary of Income Tax Expense (Benefit) Reconciliation	The income tax expense (benefit) differed from the amounts computed by applying the statutory U.S. federal income tax rate of 21 % in 2022, 2021 and 2020 to pretax income as a result of the following (dollars in thousands): Year Ended December 31, 2022 2021 2020 Income (loss) before income taxes $ ( 20,490 ) $ ( 1,710 ) $ ( 238 ) Statutory U.S. federal income tax rate ( 4,303 ) ( 359 ) ( 50 ) State income taxes, net of federal benefit ( 5,984 ) 174 44 Tax‑exempt investment income and dividend received deduction ( 22 ) ( 40 ) ( 50 ) Nondeductible meals and entertainment 79 33 23 Valuation allowance on deferred tax assets 3,715 676 ( 205 ) Equity-earnings from Affiliate 195 170 88 Net gain from sale of agency assets ( 2,848 ) — — Utilization of state NOLs ( 386 ) — — PPP Loan forgiveness — ( 578 ) — Other 113 132 156 Income tax expense (benefit) $ ( 9,441 ) $ 208 $ 6 Effective tax rate 46.1 % ( 12.2 )% ( 2.6 )%
Schedule of Deferred Tax Assets and Liabilities	The tax effects of temporary differences that give rise to significant portions of the deferred tax assets and deferred tax liabilities are presented below (dollars in thousands): December 31, 2022 2021 Deferred tax assets: Discounted unpaid losses and loss adjustment expenses $ 1,217 $ 1,555 Unearned premiums 2,324 2,561 Net operating loss carryforwards 12,152 12,544 Net unrealized losses on investments 3,687 418 State net operating loss carryforwards 5,097 822 Other 403 102 Gross deferred tax assets 24,880 18,002 Less valuation allowance ( 21,663 ) ( 14,594 ) Total deferred tax assets, net of allowance 3,217 3,408 Deferred tax liabilities: Investment basis difference 23 15 Tax rate change transition discounting 137 183 Equity investment in Affiliate 691 470 Net unrealized gains on investments — — Deferred policy acquisition costs 2,161 2,576 Intangible assets 115 115 Property and equipment 41 47 Other 49 2 Total deferred tax liabilities 3,217 3,408 Net deferred tax liability $ — $ —

Statutory Financial Data, Ris_2

Statutory Financial Data, Risk-Based Capital and Dividend Restrictions (Tables)	12 Months Ended
	Dec. 31, 2022
Insurance [Abstract]
Summary of Statutory Basis Information	Summarized 2022, 2021 and 2020 statutory basis information for the non-captive Insurance Company Subsidiaries, which differs from generally accepted accounting principles, is as follows (dollars in thousands). CIC WPIC 2022 Statutory capital and surplus $ 47,827 $ 20,651 RBC authorized control level 15,541 5,098 Statutory net income (loss) ( 6,846 ) ( 4,171 ) RBC % 308 % 405 % CIC WPIC 2021 Statutory capital and surplus $ 50,194 $ 23,603 RBC authorized control level 15,868 5,331 Statutory net income (loss) ( 9,161 ) ( 614 ) RBC % 316 % 443 % CIC WPIC 2020 Statutory capital and surplus $ 49,271 $ 24,723 RBC authorized control level 14,221 4,547 Statutory net income (loss) 2,059 1,024 RBC % 346 % 544 %

Accumulated Other Comprehensi_2

Accumulated Other Comprehensive Income (Loss) (Tables)	12 Months Ended
	Dec. 31, 2022
Equity [Abstract]
Schedule of Accumulated Other Comprehensive Income (Loss)	The following table presents changes in accumulated other comprehensive income (loss) for unrealized gains and losses on available-for-sale securities (dollars in thousands): Year Ended 2022 2021 Balance at beginning of period $ ( 2,110 ) $ 912 Other comprehensive income (loss) before reclassifications ( 16,024 ) ( 2,937 ) Less: amounts reclassified from accumulated other comprehensive income (loss) 69 85 Net current period other comprehensive income (loss) ( 16,093 ) ( 3,022 ) Balance at end of period $ ( 18,203 ) $ ( 2,110 )

Earnings Per Share (Tables)

Earnings Per Share (Tables)	12 Months Ended
	Dec. 31, 2022
Earnings Per Share [Abstract]
Schedule of Earnings Per Share	The following table presents the calculation of basic and diluted earnings (loss) per common share, as follows (dollars in thousands, except share and per share amounts): Year Ended 2022 2021 2020 Net income (loss) $ ( 10,681 ) $ ( 1,094 ) $ 595 Weighted average common shares, basic and diluted* 10,692,090 9,691,998 9,625,059 Earnings (loss) per share, basic and diluted ( 1.00 ) $ ( 0.11 ) $ 0.06 * The non-vested shares of the restricted stock units and stock options were anti-dilutive as of December 31, 2022, 2021, and 2020. Therefore, the non-vested shares are excluded from earnings (loss) per share for the years ended December 31, 2022, 2021, and 2020 .

Segment Information (Tables)

Segment Information (Tables)	12 Months Ended
	Dec. 31, 2022
Segment Reporting [Abstract]
Schedule of Information by Reportable Segment	The following table summarizes our net earned premiums: Net Earned Premium 2022 2021 2020 Commercial 84 % 89 % 92 % Personal 16 % 11 % 8 % Total 100 % 100 % 100 % The wholesale agency business sells insurance products on behalf of the Company’s commercial and personal lines businesses as well as to third-party insurers. Certain acquisition costs incurred by the commercial and personal lines businesses are reflected as commission revenue for the wholesale agency business and are eliminated in the Eliminations category. In addition to the reportable segments, the Company maintains a Corporate and Other category to reconcile segment results to the consolidated totals. The Corporate and Other category includes: (i) corporate operating expenses such as salaries and related benefits of the Company’s executive management team, some finance and information technology personnel, and other corporate headquarters expenses, (ii) interest expense on the Company’s debt obligations; (iii) depreciation and amortization on property and equipment, and (iv) all investment income activity. All investment income activity is reported within net investment income, net realized investment gains, and change in fair value of equity securities on the consolidated statements of operations. The Company’s assets on the consolidated balance sheet are not allocated to the reportable segments. The following tables present information by reportable segment (dollars in thousands): Year Ended December 31, 2022 Commercial Personal Under-writing Wholesale Agency Corp-orate Elim-inations Total Gross written premiums $ 116,868 $ 21,151 $ 138,019 $ — $ — $ — $ 138,019 Net written premiums $ 72,318 $ 18,914 $ 91,232 $ — $ — $ — $ 91,232 Net earned premiums $ 80,823 $ 15,888 $ 96,711 $ — $ — $ — $ 96,711 Other income 245 82 327 5,712 271 ( 3,542 ) 2,768 Segment revenue 81,068 15,970 97,038 5,712 271 ( 3,542 ) 99,479 Loss and loss adjustment expenses, net 70,762 10,678 81,440 — — — 81,440 Policy acquisition costs 17,682 4,604 22,286 3,653 — ( 3,760 ) 22,179 Operating expenses 13,069 1,936 15,005 2,612 1,192 ( 20 ) 18,789 Loss portfolio transfer risk fee 5,400 — — — — — 5,400 Segment expenses 106,913 17,218 118,731 6,265 1,192 ( 3,780 ) 127,808 Segment underwriting gain (loss) ( 25,845 ) ( 1,248 ) ( 21,693 ) ( 553 ) ( 921 ) 238 ( 28,329 ) Net investment income 32 3,011 3,043 Net realized investment gains (losses) ( 1,505 ) ( 1,505 ) Change in fair value of equity securities 403 403 Gain from VSRM Transaction 8,810 8,810 Other gains ( 1 ) 60 59 Interest expense ( 42 ) ( 2,929 ) ( 2,971 ) Income (loss) before income taxes $ ( 25,845 ) $ ( 1,248 ) $ ( 21,693 ) $ ( 564 ) $ 6,929 $ 238 $ ( 20,490 ) Selected Balance Sheet Data: Deferred policy acquisition costs $ 7,683 $ 2,796 $ ( 189 ) $ 10,290 Unearned premiums 56,565 11,322 67,887 Unpaid losses and loss adjustment expenses 159,558 5,981 165,539 Year Ended December 31, 2021 Commercial Personal Under-writing Wholesale Agency Corp-orate Elim-inations Total Gross written premiums $ 117,075 $ 15,020 $ 132,095 $ — $ — $ — $ 132,095 Net written premiums $ 87,307 $ 14,122 $ 101,429 $ — $ — $ — $ 101,429 Net earned premiums $ 87,759 $ 11,043 $ 98,802 $ — $ — $ — $ 98,802 Other income 215 143 358 5,848 365 ( 3,900 ) 2,671 Segment revenue 87,974 11,186 99,160 5,848 365 ( 3,900 ) 101,473 Loss and loss adjustment expenses, net 63,868 5,993 69,861 — — — 69,861 Policy acquisition costs 25,687 3,307 28,994 3,727 — ( 4,270 ) 28,451 Operating expenses 11,648 1,357 13,005 2,382 1,122 — 16,509 Segment expenses 101,203 10,657 111,860 6,109 1,122 ( 4,270 ) 114,821 Segment underwriting gain (loss) ( 13,229 ) 529 ( 12,700 ) ( 261 ) ( 757 ) $ 370 ( 13,348 ) Net investment income 1,968 1,968 Net realized investment gains 2,878 2,878 Change in fair value of equity securities ( 2,020 ) ( 2,020 ) Other gains 11,664 11,664 Interest expense ( 2,852 ) ( 2,852 ) Income (loss) before income taxes $ ( 13,229 ) $ 529 $ ( 12,700 ) $ ( 261 ) $ 10,881 $ 370 $ ( 1,710 ) Selected Balance Sheet Data: Deferred policy acquisition costs $ 10,619 $ 2,075 $ ( 427 ) $ 12,267 Unearned premiums 57,491 7,778 65,269 Unpaid losses and loss adjustment expenses 135,084 4,001 139,085 Year Ended December 31, 2020 Commercial Personal Under-writing Wholesale Agency Corp-orate Elim-inations Total Gross written premiums $ 102,763 $ 8,572 $ 111,335 $ — $ — $ — $ 111,335 Net written premiums $ 85,385 $ 7,555 $ 92,940 $ — $ — $ — $ 92,940 Net earned premiums $ 82,409 $ 6,694 $ 89,103 $ — $ — $ — $ 89,103 Other income 242 150 392 7,571 245 ( 5,593 ) 2,615 Segment revenue 82,651 6,844 89,495 7,571 245 ( 5,593 ) 91,718 Loss and loss adjustment expenses, net 53,263 2,965 56,228 — — — 56,228 Policy acquisition costs 25,051 2,044 27,095 4,938 — ( 5,928 ) 26,105 Operating expenses 12,644 1,069 13,713 3,107 1,648 — 18,468 Segment expenses 90,958 6,078 97,036 8,045 1,648 ( 5,928 ) 100,801 Segment underwriting gain (loss) ( 8,307 ) 766 ( 7,541 ) ( 474 ) ( 1,403 ) $ 335 ( 9,083 ) Net investment income 3,156 3,156 Net realized investment gains 8,126 8,126 Change in fair value of equity securities 228 228 Other gains 260 260 Interest expense ( 2,925 ) ( 2,925 ) Income (loss) before income taxes $ ( 8,307 ) $ 766 $ ( 7,541 ) $ ( 474 ) $ 7,442 $ 335 $ ( 238 ) Selected Balance Sheet Data: Deferred policy acquisition costs $ 11,858 $ 1,183 $ ( 798 ) $ 12,243 Unearned premiums 51,535 4,689 56,224 Unpaid losses and loss adjustment expenses 106,662 4,608 111,270

Summary of Significant Accoun_3

Summary of Significant Accounting Policies - Narrative (Details)	12 Months Ended
	Dec. 31, 2022 USD ($) State Class_business	Dec. 31, 2021 USD ($)
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Number of types of business | Class_business	3
Number of states in which entity operates | State	50
Discount rate	6.75%
Unrecognized tax benefits	$ 0	$ 0
Income tax penalties and interest accrued	0	0
Net unrealized losses	16,000,000
Net unrealized losses in debt securities	18,200,000
Accounting Standards Update 2016-02
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Right-of-use asset	$ 1,300,000	$ 1,400,000
Operating Lease, Right-of-Use Asset, Statement of Financial Position [Extensible Enumeration]	Other assets	Other assets
Lease liability	$ 1,300,000	$ 1,500,000
Operating Lease, Liability, Statement of Financial Position [Extensible Enumeration]	Other liabilities	Other liabilities
Minimum
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Lease term	5 years
Maximum
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Lease term	10 years

VSRM Transaction - Narrative (D

VSRM Transaction - Narrative (Details) - USD ($)				1 Months Ended	3 Months Ended	12 Months Ended
	Oct. 14, 2022	Oct. 13, 2022	Oct. 12, 2022	Dec. 31, 2022	Dec. 31, 2022	Dec. 31, 2021
Business Acquisition [Line Items]
Asset acquisition debt not transferred		$ 8,900,000
Asset acquisition tax liability not transferred		9,400,000
Asset purchase agreement purchase price	$ 38,200,000
Operating loss carry forwards, net of tax		9,400,000
Gain or loss on sale of business						$ 8,910,000
VSRM
Business Acquisition [Line Items]
Ownership percentage	50%
Accounts receivable	$ 4,300,000
Current liabilities	5,800,000
Cash	271,000
Asset purchase agreement purchase price paid in cash	32,800,000
Asset purchase agreement purchase price paid in the form of the buyer's stock	3,800,000
Cash held back by buyer	(75,000)
Fair value of equity interest prior to acquisition			$ 10,600,000
VSRM | Promissory Note
Business Acquisition [Line Items]
Payments to acquire interest in venture	$ 9,700,000
Domestic
Business Acquisition [Line Items]
Net operating loss carryforwards		12,500,000
State
Business Acquisition [Line Items]
Net operating loss carryforwards		$ 14,800,000		$ 107,200,000	$ 107,200,000
Sycamore Specialty Underwriters | VSRM
Business Acquisition [Line Items]
Net asset transferred, fair value				0
Promissory note assumed as part of contribution of business				1,000,000
Sycamore Specialty Underwriters | VSRM | Vice President [Member]
Business Acquisition [Line Items]
Purchase price amount				1,000	1,000
Gain or loss on sale of business				$ 0
Asset Purchase Agreement
Business Acquisition [Line Items]
Non-operating gains, net of taxes generated					$ 8,800,000
Venture
Business Acquisition [Line Items]
Percentage of ownership interest purchased	50%	50%	50%
Payments to acquire interest in venture		$ 9,700,000
Settled the note with cash received from sale of Security & Alarm Business		5,900,000
Form of stock from the buyer of the Security & Alarm Business		3,800,000
Revaluation gain on step acquisition		$ 8,810,000
Ownership percentage		100%
Accounts receivable		$ 4,604,000
Cash		3,921,000
Venture | Promissory Note
Business Acquisition [Line Items]
Payments to acquire interest in venture		$ 9,700,000
Sycamore Specialty Underwriters | VSRM | Vice President [Member]
Business Acquisition [Line Items]
Percentage of ownership interest purchased				50%	50%

VSRM Transaction - Schedule of

VSRM Transaction - Schedule of Condensed Assets and Liabilities Incorporated Into The Consolidated Balance Sheet from The VSRM Acquisition (Details) - Venture $ in Thousands	Oct. 13, 2022 USD ($)
Business Acquisition [Line Items]
Cash	$ 3,921
Trade receivables	4,604
Customer relationship intangible assets	37,122
Other assets	574
Total assets	46,221
Trade and other payables	7,624
Deferred tax liability	9,407
Note payable to Affiliate	6,000
Senior debt	2,917
Total Liabilities	25,948
Fair value of net assets acquired	$ 20,273

VSRM Transaction - Schedule o_2

VSRM Transaction - Schedule of Calculation of Revaluation Gain Related to Company's Equity Method Investment in VSRM as a Result of VSRM Transaction (Details) - Venture $ in Thousands	Oct. 13, 2022 USD ($)
Business Acquisition [Line Items]
Carrying value of equity method investment in VSRM	$ 1,773
Fair value of investment in VSRM	10,583
Gain on step acquisition	$ 8,810

VSRM Transaction - Schedule o_3

VSRM Transaction - Schedule of Calculation of Gain on VSRM Transaction (Parenthetical) (Details)	Oct. 14, 2022	Oct. 13, 2022	Oct. 12, 2022
Venture
Business Acquisition [Line Items]
Percentage of ownership interest purchased	50%	50%	50%

VSRM Transaction - Schedule o_4

VSRM Transaction - Schedule of Reconciles the Net Assets Disposed (Details) $ in Thousands	Oct. 14, 2022 USD ($)
Business Acquisition [Line Items]
Purchase price	$ 38,200
Venture
Business Acquisition [Line Items]
Cash at closing	32,759
Net liabilities transferred	1,499
Hold back	75
Stock of acquirer	3,822
Purchase price	38,155
Cash	271
Premiums transferred to buyer	4,326
Intangible assets	38,154
Trade payables and accrued liabilities assumed by buyer	(5,838)
Net assets disposed of	36,913
Net gain	1,242
Broker fee transaction costs	$ (1,242)

VSRM Transaction - Net Gain on

VSRM Transaction - Net Gain on Revaluation of the Investment in VSRM and the Disposal of the Security and Alarm Business Line (Details) - USD ($) $ in Thousands		12 Months Ended
	Oct. 14, 2022	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Business Acquisition [Line Items]
Net gain		$ 8,810	$ 0	$ 0
Venture
Business Acquisition [Line Items]
Gross gains	$ 10,052
Broker fee	(1,242)
Net gain	$ 8,810

VSRM Transaction - Schedule o_5

VSRM Transaction - Schedule of Assets And Liabilities Deconsolidated as a Result of This Transaction (Details) - VSRM - Sycamore Specialty Underwriters $ in Thousands	Dec. 31, 2022 USD ($)
Business Acquisition [Line Items]
Cash	$ 497
Receivable from VSRM	934
Trade receivables	239
Intangible asset	196
Other assets	514
Total assets	2,380
Payable to Affiliates	286
Trade payables	193
Note payable	1,000
Other liabilities	901
Total Liabilities	$ 2,380

Sale of Certain Agency Busine_2

Sale of Certain Agency Business - Narrative (Details)			6 Months Ended	12 Months Ended
	Oct. 20, 2022 USD ($)	Dec. 14, 2021 USD ($)	Jun. 30, 2021 USD ($)	Dec. 31, 2022 USD ($) Interger	Dec. 31, 2021 USD ($)	Dec. 31, 2020 USD ($)
Other gains (losses)				$ 59,000	$ 11,664,000	$ 260,000
Venture Holdings, Inc
Other gains (losses)			$ 8,900,000
Purchase price			10,000,000
Paid in cash			$ 1,000,000
Number of promissory notes | Interger				2
Payment annum rate				7%
Payment maturity period				5 years
Repayments of Debt	$ 5,000,000	$ 3,000,000
Venture Holdings, Inc | Prepayment Penalty
Repayments of Debt				$ 0
Venture Holdings, Inc | Promissory Notes
Remaining balance paid by promissory note				9,000,000
Venture Holdings, Inc | Promissory Notes One
Remaining balance paid by promissory note	$ 6,000,000			6,000,000
Venture Holdings, Inc | Promissory Notes Two
Remaining balance paid by promissory note				3,000,000
Sycamore Specialty Underwriters | Promissory Notes One
Promissory note assumed as part of contribution of business				$ 1,000,000

Investments - Available-for-sal

Investments - Available-for-sale Securities (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Debt Securities, Available-for-sale [Line Items]
Debt securities, Cost or Amortized Cost	$ 127,119	$ 150,732
Debt securities, Gross Unrealized Gain	1	898
Debt securities, Gross Unrealized Losses	(16,919)	(1,847)
Debt securities, Estimated Fair Value	110,201	149,783
U.S. Government
Debt Securities, Available-for-sale [Line Items]
Debt securities, Cost or Amortized Cost	7,833	20,723
Debt securities, Gross Unrealized Gain	0	74
Debt securities, Gross Unrealized Losses	(335)	(77)
Debt securities, Estimated Fair Value	7,498	20,720
State and local government
Debt Securities, Available-for-sale [Line Items]
Debt securities, Cost or Amortized Cost	25,487	30,063
Debt securities, Gross Unrealized Gain	1	555
Debt securities, Gross Unrealized Losses	(4,672)	(189)
Debt securities, Estimated Fair Value	20,816	30,429
Corporate debt
Debt Securities, Available-for-sale [Line Items]
Debt securities, Cost or Amortized Cost	35,347	30,808
Debt securities, Gross Unrealized Gain	0	88
Debt securities, Gross Unrealized Losses	(4,788)	(550)
Debt securities, Estimated Fair Value	30,559	30,346
Asset-backed securities
Debt Securities, Available-for-sale [Line Items]
Debt securities, Cost or Amortized Cost	21,742	28,652
Debt securities, Gross Unrealized Gain	0	10
Debt securities, Gross Unrealized Losses	(1,246)	(224)
Debt securities, Estimated Fair Value	20,496	28,438
Mortgage-backed securities
Debt Securities, Available-for-sale [Line Items]
Debt securities, Cost or Amortized Cost	29,194	33,178
Debt securities, Gross Unrealized Gain	0	105
Debt securities, Gross Unrealized Losses	(5,157)	(762)
Debt securities, Estimated Fair Value	24,037	32,521
Commercial mortgage-backed securities
Debt Securities, Available-for-sale [Line Items]
Debt securities, Cost or Amortized Cost	3,414	1,659
Debt securities, Gross Unrealized Gain	0	31
Debt securities, Gross Unrealized Losses	(186)	0
Debt securities, Estimated Fair Value	3,228	1,690
Collateralized mortgage obligations
Debt Securities, Available-for-sale [Line Items]
Debt securities, Cost or Amortized Cost	4,102	5,649
Debt securities, Gross Unrealized Gain	0	35
Debt securities, Gross Unrealized Losses	(535)	(45)
Debt securities, Estimated Fair Value	$ 3,567	$ 5,639

Investments - Available-for-s_2

Investments - Available-for-sale Securities in Unrealized Loss Positions (Details) $ in Thousands	Dec. 31, 2022 USD ($) Security	Dec. 31, 2021 USD ($) Security
Debt Securities, Available-for-sale, Continuous Unrealized Loss Position, Number of Positions [Abstract]
Debt securities, less than 12 months, number of issues | Security	205	134
Debt securities, 12 months or More, number of issues | Security	133	10
Debt securities, number of issues | Security	338	144
Debt Securities, Available-for-sale, Unrealized Loss Position [Abstract]
Debt securities, less than 12 months, fair value	$ 38,757	$ 95,923
Debt securities, 12 months or More, fair value	71,142	7,801
Debt securities, fair value	109,899	103,724
Debt Securities, Available-for-sale, Unrealized Loss Position, Accumulated Loss [Abstract]
Debt securities, less than 12 months, unrealized losses	(4,857)	(1,750)
Debt securities, 12 months or More, unrealized losses	(12,062)	(97)
Debt securities, total unrealized losses	$ (16,919)	$ (1,847)
U.S. Government
Debt Securities, Available-for-sale, Continuous Unrealized Loss Position, Number of Positions [Abstract]
Debt securities, less than 12 months, number of issues | Security	8	6
Debt securities, 12 months or More, number of issues | Security	5	1
Debt securities, number of issues | Security	13	7
Debt Securities, Available-for-sale, Unrealized Loss Position [Abstract]
Debt securities, less than 12 months, fair value	$ 3,534	$ 10,323
Debt securities, 12 months or More, fair value	3,964	4,728
Debt securities, fair value	7,498	15,051
Debt Securities, Available-for-sale, Unrealized Loss Position, Accumulated Loss [Abstract]
Debt securities, less than 12 months, unrealized losses	(135)	(47)
Debt securities, 12 months or More, unrealized losses	(200)	(30)
Debt securities, total unrealized losses	$ (335)	$ (77)
State and local government
Debt Securities, Available-for-sale, Continuous Unrealized Loss Position, Number of Positions [Abstract]
Debt securities, less than 12 months, number of issues | Security	77	41
Debt securities, 12 months or More, number of issues | Security	45	4
Debt securities, number of issues | Security	122	45
Debt Securities, Available-for-sale, Unrealized Loss Position [Abstract]
Debt securities, less than 12 months, fair value	$ 12,966	$ 8,875
Debt securities, 12 months or More, fair value	7,147	446
Debt securities, fair value	20,113	9,321
Debt Securities, Available-for-sale, Unrealized Loss Position, Accumulated Loss [Abstract]
Debt securities, less than 12 months, unrealized losses	(2,318)	(172)
Debt securities, 12 months or More, unrealized losses	(2,354)	(17)
Debt securities, total unrealized losses	$ (4,672)	$ (189)
Corporate debt
Debt Securities, Available-for-sale, Continuous Unrealized Loss Position, Number of Positions [Abstract]
Debt securities, less than 12 months, number of issues | Security	27	41
Debt securities, 12 months or More, number of issues | Security	42	1
Debt securities, number of issues | Security	69	42
Debt Securities, Available-for-sale, Unrealized Loss Position [Abstract]
Debt securities, less than 12 months, fair value	$ 10,069	$ 22,748
Debt securities, 12 months or More, fair value	20,890	705
Debt securities, fair value	30,959	23,453
Debt Securities, Available-for-sale, Unrealized Loss Position, Accumulated Loss [Abstract]
Debt securities, less than 12 months, unrealized losses	(1,373)	(505)
Debt securities, 12 months or More, unrealized losses	(3,415)	(45)
Debt securities, total unrealized losses	$ (4,788)	$ (550)
Asset-backed securities
Debt Securities, Available-for-sale, Continuous Unrealized Loss Position, Number of Positions [Abstract]
Debt securities, less than 12 months, number of issues | Security	6	24
Debt securities, 12 months or More, number of issues | Security	20	2
Debt securities, number of issues | Security	26	26
Debt Securities, Available-for-sale, Unrealized Loss Position [Abstract]
Debt securities, less than 12 months, fair value	$ 3,188	$ 24,305
Debt securities, 12 months or More, fair value	17,308	1,893
Debt securities, fair value	20,496	26,198
Debt Securities, Available-for-sale, Unrealized Loss Position, Accumulated Loss [Abstract]
Debt securities, less than 12 months, unrealized losses	(76)	(219)
Debt securities, 12 months or More, unrealized losses	(1,170)	(5)
Debt securities, total unrealized losses	$ (1,246)	$ (224)
Mortgage-backed securities
Debt Securities, Available-for-sale, Continuous Unrealized Loss Position, Number of Positions [Abstract]
Debt securities, less than 12 months, number of issues | Security	57	12
Debt securities, 12 months or More, number of issues | Security	12	0
Debt securities, number of issues | Security	69	12
Debt Securities, Available-for-sale, Unrealized Loss Position [Abstract]
Debt securities, less than 12 months, fair value	$ 4,006	$ 27,034
Debt securities, 12 months or More, fair value	20,031	0
Debt securities, fair value	24,037	27,034
Debt Securities, Available-for-sale, Unrealized Loss Position, Accumulated Loss [Abstract]
Debt securities, less than 12 months, unrealized losses	(573)	(762)
Debt securities, 12 months or More, unrealized losses	(4,584)	0
Debt securities, total unrealized losses	$ (5,157)	$ (762)
Commercial mortgage-backed securities
Debt Securities, Available-for-sale, Continuous Unrealized Loss Position, Number of Positions [Abstract]
Debt securities, less than 12 months, number of issues | Security	4	0
Debt securities, 12 months or More, number of issues | Security	0	0
Debt securities, number of issues | Security	4	0
Debt Securities, Available-for-sale, Unrealized Loss Position [Abstract]
Debt securities, less than 12 months, fair value	$ 3,205	$ 0
Debt securities, 12 months or More, fair value	0	0
Debt securities, fair value	3,205	0
Debt Securities, Available-for-sale, Unrealized Loss Position, Accumulated Loss [Abstract]
Debt securities, less than 12 months, unrealized losses	(186)	0
Debt securities, 12 months or More, unrealized losses	0	0
Debt securities, total unrealized losses	$ (186)	$ 0
Collateralized mortgage obligations
Debt Securities, Available-for-sale, Continuous Unrealized Loss Position, Number of Positions [Abstract]
Debt securities, less than 12 months, number of issues | Security	26	10
Debt securities, 12 months or More, number of issues | Security	9	2
Debt securities, number of issues | Security	35	12
Debt Securities, Available-for-sale, Unrealized Loss Position [Abstract]
Debt securities, less than 12 months, fair value	$ 1,789	$ 2,638
Debt securities, 12 months or More, fair value	1,802	29
Debt securities, fair value	3,591	2,667
Debt Securities, Available-for-sale, Unrealized Loss Position, Accumulated Loss [Abstract]
Debt securities, less than 12 months, unrealized losses	(196)	(45)
Debt securities, 12 months or More, unrealized losses	(339)	0
Debt securities, total unrealized losses	$ (535)	$ (45)

Investments - Net Investment In

Investments - Net Investment Income (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Net Investment Income [Line Items]
Investment income	$ 3,345	$ 2,413	$ 3,571
Investment expenses	(302)	(445)	(415)
Net investment income	3,043	1,968	3,156
Debt securities
Net Investment Income [Line Items]
Investment income	2,517	2,217	3,213
Equity securities
Net Investment Income [Line Items]
Investment income	52	194	220
Cash, cash equivalents and short-term investments
Net Investment Income [Line Items]
Investment income	$ 776	$ 2	$ 138

Investments - Gross Realized Ga

Investments - Gross Realized Gains and Losses (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Debt securities:
Gross realized gains	$ 6	$ 63	$ 4,646
Gross realized losses	(155)	(6)	(8)
Total debt securities	(149)	57	4,638
Equity securities:
Gross realized gains	375	4,605	4,854
Gross realized losses	(1,731)	(1,784)	(1,366)
Total equity securities	(1,356)	2,821	3,488
Total net realized investment gains	$ (1,505)	$ 2,878	$ 8,126

Investments - Narrative (Detail

Investments - Narrative (Details) - USD ($)	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020	Dec. 31, 2019
Investments, Debt and Equity Securities [Abstract]
Proceeds from sale of available-for-sale debt securities	$ 32,000,000	$ 31,700,000		$ 101,200,000
Gross realized gains from sales of available-for-sale debt securities	5,000	27,000	$ 4,600,000
Gross realized losses from sales of available-for-sale debt securities	155,000	6,000	0
Gross unrealized gains	0	0	1,000,000
Gross unrealized losses	638,000	1,000,000	0
Amount payable for securities purchased	0	1,000,000	700,000
Amount receivable for securities sold	650,000	523,000	$ 809,000
Other than temporary impairments losses, investments	0
Investments	1,800,000
Deposits held in trust accounts	8,000,000	8,500,000
Deposits, held in trust for collateral requirements	$ 95,700,000	$ 76,100,000

Investments - Available-for-s_3

Investments - Available-for-sale Fixed Maturity Securities by Contractual Maturity (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Amortized Cost
Due in one year or less	$ 4,876
Due after one year through five years	28,396
Due after five years through ten years	23,974
Due after ten years	11,421
Securities with contractual maturities	68,667
Total debt securities	127,119	$ 150,732
Estimated Fair Value
Due in one year or less	4,770
Due after one year through five years	25,963
Due after five years through ten years	19,782
Due after ten years	8,358
Securities with contractual maturities	58,873
Total debt securities	110,201	149,783
Asset-backed securities
Amortized Cost
Total debt securities	21,742	28,652
Estimated Fair Value
Total debt securities	20,496	28,438
Mortgage-backed securities
Amortized Cost
Total debt securities	29,194	33,178
Estimated Fair Value
Total debt securities	24,037	32,521
Commercial mortgage-backed securities
Amortized Cost
Total debt securities	3,414	1,659
Estimated Fair Value
Total debt securities	3,228	1,690
Collateralized mortgage obligations
Amortized Cost
Total debt securities	4,102	5,649
Estimated Fair Value
Total debt securities	$ 3,567	$ 5,639

Fair Value Measurements - Finan

Fair Value Measurements - Financial Instruments (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021	Apr. 24, 2020
Assets:
Debt securities, Estimated Fair Value	$ 110,201	$ 149,783
Equity Securities	917	9,437
Short-term investments	25,929	23,013
Total marketable investments measured at fair value	137,047	182,233
Total assets measured at fair value	137,397	182,727
Liabilities:
Total Liabilities (non-recurring fair value measure)	33,730	35,822
Debt	33,876	33,564
Paycheck Protection Program
Liabilities:
Debt			$ 2,700
U.S. Government
Assets:
Debt securities, Estimated Fair Value	7,498	20,720
State and local government
Assets:
Debt securities, Estimated Fair Value	20,816	30,429
Corporate debt
Assets:
Debt securities, Estimated Fair Value	30,559	30,346
Asset-backed securities
Assets:
Debt securities, Estimated Fair Value	20,496	28,438
Mortgage-backed securities
Assets:
Debt securities, Estimated Fair Value	24,037	32,521
Commercial mortgage-backed securities
Assets:
Debt securities, Estimated Fair Value	3,228	1,690
Collateralized mortgage obligations
Assets:
Debt securities, Estimated Fair Value	3,567	5,639
Senior Unsecured Notes
Liabilities:
Debt	22,430	24,118
Subordinated notes
Liabilities:
Debt	11,300	11,704
Partnership interest
Assets:
Investments measured at NAV	350	494
Level 1
Assets:
Debt securities, Estimated Fair Value	0	0
Equity Securities	160	9,154
Short-term investments	25,929	23,013
Total marketable investments measured at fair value	26,089	32,167
Liabilities:
Total Liabilities (non-recurring fair value measure)	0	0
Level 1 | U.S. Government
Assets:
Debt securities, Estimated Fair Value	0	0
Level 1 | State and local government
Assets:
Debt securities, Estimated Fair Value	0	0
Level 1 | Corporate debt
Assets:
Debt securities, Estimated Fair Value	0	0
Level 1 | Asset-backed securities
Assets:
Debt securities, Estimated Fair Value	0	0
Level 1 | Mortgage-backed securities
Assets:
Debt securities, Estimated Fair Value	0	0
Level 1 | Commercial mortgage-backed securities
Assets:
Debt securities, Estimated Fair Value	0	0
Level 1 | Collateralized mortgage obligations
Assets:
Debt securities, Estimated Fair Value	0	0
Level 1 | Senior Unsecured Notes
Liabilities:
Debt	0	0
Level 1 | Subordinated notes
Liabilities:
Debt	0	0
Level 2
Assets:
Debt securities, Estimated Fair Value	110,201	149,783
Equity Securities	757	283
Short-term investments	0
Total marketable investments measured at fair value	110,958	150,066
Liabilities:
Total Liabilities (non-recurring fair value measure)	22,430	24,118
Level 2 | U.S. Government
Assets:
Debt securities, Estimated Fair Value	7,498	20,720
Level 2 | State and local government
Assets:
Debt securities, Estimated Fair Value	20,816	30,429
Level 2 | Corporate debt
Assets:
Debt securities, Estimated Fair Value	30,559	30,346
Level 2 | Asset-backed securities
Assets:
Debt securities, Estimated Fair Value	20,496	28,438
Level 2 | Mortgage-backed securities
Assets:
Debt securities, Estimated Fair Value	24,037	32,521
Level 2 | Commercial mortgage-backed securities
Assets:
Debt securities, Estimated Fair Value	3,228	1,690
Level 2 | Collateralized mortgage obligations
Assets:
Debt securities, Estimated Fair Value	3,567	5,639
Level 2 | Senior Unsecured Notes
Liabilities:
Debt	22,430	24,118
Level 2 | Subordinated notes
Liabilities:
Debt	0	0
Level 3
Assets:
Debt securities, Estimated Fair Value	0	0
Equity Securities	0	0
Short-term investments	0	0
Total marketable investments measured at fair value	0	0
Liabilities:
Total Liabilities (non-recurring fair value measure)	11,300	11,704
Level 3 | U.S. Government
Assets:
Debt securities, Estimated Fair Value	0	0
Level 3 | State and local government
Assets:
Debt securities, Estimated Fair Value	0	0
Level 3 | Corporate debt
Assets:
Debt securities, Estimated Fair Value	0	0
Level 3 | Asset-backed securities
Assets:
Debt securities, Estimated Fair Value	0	0
Level 3 | Mortgage-backed securities
Assets:
Debt securities, Estimated Fair Value	0	0
Level 3 | Commercial mortgage-backed securities
Assets:
Debt securities, Estimated Fair Value	0	0
Level 3 | Collateralized mortgage obligations
Assets:
Debt securities, Estimated Fair Value	0	0
Level 3 | Senior Unsecured Notes
Liabilities:
Debt	0	0
Level 3 | Subordinated notes
Liabilities:
Debt	$ 11,300	$ 11,704

Fair Value Measurements - Narra

Fair Value Measurements - Narrative (Details)	Dec. 31, 2022
Level 1
Fair Value, Concentration of Risk, Financial Statement Captions [Line Items]
Marketable investment percentage	18%
Level 2
Fair Value, Concentration of Risk, Financial Statement Captions [Line Items]
Marketable investment percentage	82%

Deferred Policy Acquisition C_3

Deferred Policy Acquisition Costs - Activity in Deferred Policy Acquisition Costs (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Movement Analysis of Deferred Policy Acquisition Costs [Roll Forward]
Balance at beginning of period	$ 12,267	$ 12,243	$ 11,906
Deferred policy acquisition costs	20,202	28,475	26,442
Amortization of policy acquisition costs	(22,179)	(28,451)	(26,105)
Net change	(1,977)	24	337
Balance at end of period	$ 10,290	$ 12,267	$ 12,243

Unpaid Losses and Loss Adjust_3

Unpaid Losses and Loss Adjustment Expenses - Changes in the Liability for Unpaid Losses and Loss Adjustment Expenses (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Gross reserves - beginning of period	$ 139,085	$ 111,270	$ 107,246
Less: reinsurance recoverables on unpaid losses	40,344	24,218	22,579
Net reserves - beginning of period	98,741	87,052	84,667
Add: incurred losses and loss adjustment expenses, net of reinsurance
Current period	57,156	50,429	40,634
Prior period	24,284	19,432	15,594
Total net incurred losses and LAE	81,440	69,861	56,228
Deduct: loss and loss adjustment expense payments, net of reinsurance
Current period	20,894	18,984	13,599
Prior period	76,399	39,188	40,244
Total net loss and loss adjustment expense payments	97,293	58,172	53,843
Net reserves - end of period	82,888	98,741	87,052
Plus: reinsurance recoverables on unpaid losses	82,651	40,344	24,218
Gross reserves - end of period	$ 165,539	$ 139,085	$ 111,270

Unpaid Losses and Loss Adjust_4

Unpaid Losses and Loss Adjustment Expenses - Narrative (Details) - USD ($)	3 Months Ended	12 Months Ended
	Mar. 31, 2021	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020	Dec. 31, 2019
Liability for Claims and Claims Adjustment Expense [Line Items]
Prior year adjustments		$ 24,284,000	$ 19,432,000	$ 15,594,000
Losses and loss adjustment expenses, net		81,440,000	69,861,000	56,228,000
Unpaid losses and loss adjustment expenses		165,539,000	139,085,000	111,270,000	$ 107,246,000
Short-Duration Insurance Contract, Accident Year 2021 [Member]
Liability for Claims and Claims Adjustment Expense [Line Items]
Prior year adjustments		1,800,000
Short-Duration Insurance Contract, Accident Year 2020 [Member]
Liability for Claims and Claims Adjustment Expense [Line Items]
Prior year adjustments		4,000,000
Short-Duration Insurance Contract, Accident Year 2019 [Member]
Liability for Claims and Claims Adjustment Expense [Line Items]
Prior year adjustments		9,600,000
Short-Duration Insurance Contracts, Accident Year 2018 [Member]
Liability for Claims and Claims Adjustment Expense [Line Items]
Prior year adjustments		5,200,000
Short-Duration Insurance Contracts, Accident Year 2017 [Member]
Liability for Claims and Claims Adjustment Expense [Line Items]
Prior year adjustments		$ 3,700,000
Winter Storm Uri
Liability for Claims and Claims Adjustment Expense [Line Items]
Losses and loss adjustment expenses, net	$ 2,000,000
Commercial Line
Liability for Claims and Claims Adjustment Expense [Line Items]
Prior year adjustments			18,500,000	15,200,000
Personal Line
Liability for Claims and Claims Adjustment Expense [Line Items]
Prior year adjustments			957,000	352,000
Hospitality
Liability for Claims and Claims Adjustment Expense [Line Items]
Prior year adjustments			12,000,000	12,000,000
Small Business Lines
Liability for Claims and Claims Adjustment Expense [Line Items]
Prior year adjustments			$ 6,500,000	$ 3,200,000

Unpaid Losses and Loss Adjust_5

Unpaid Losses and Loss Adjustment Expenses - Loss Development (Details) $ in Thousands	Dec. 31, 2022 USD ($) Claim	Dec. 31, 2021 USD ($) Claim	Dec. 31, 2020 USD ($)	Dec. 31, 2019 USD ($)	Dec. 31, 2018 USD ($)	Dec. 31, 2017 USD ($)	Dec. 31, 2016 USD ($)	Dec. 31, 2015 USD ($)	Dec. 31, 2014 USD ($)	Dec. 31, 2013 USD ($)
Claims Development [Line Items]
Incurred	$ 533,041
Total IBNR	37,205
Cumulative Paid	432,309
Net Unpaid losses and ALAE, years 2013 through 2022	100,732
Unpaid losses and ALAE, prior to 2013	177
Unpaid Losses, LPT	(25,913)
Unpaid losses and ALAE, net of reinsurance	74,996
Commercial Lines
Claims Development [Line Items]
Incurred	424,008									$ 10,018
Total IBNR	35,662
Cumulative Paid		$ 327,763
Net Unpaid losses and ALAE, years 2013 through 2022	96,245
Unpaid losses and ALAE, prior to 2013	177
Unpaid Losses, LPT	(25,913)
Unpaid losses and ALAE, net of reinsurance	70,509
Personal Lines
Claims Development [Line Items]
Incurred	109,033
Total IBNR	1,543
Cumulative Paid	104,546
Net Unpaid losses and ALAE, years 2013 through 2022	4,487
Unpaid losses and ALAE, net of reinsurance	4,487
Accident Year 2013
Claims Development [Line Items]
Incurred	31,411	31,094	$ 31,030	$ 30,846	$ 30,420	$ 30,419	$ 29,375	$ 28,817	$ 27,431	28,052
Total IBNR
Cumulative number of reported claims | Claim	5,821
Cumulative Paid	$ 31,300	30,929	30,842	30,351	29,824	29,162	27,223	25,695	22,094	13,934
Accident Year 2013 | Commercial Lines
Claims Development [Line Items]
Incurred	12,046	11,867	11,804	11,624	11,218	11,252	10,237	9,893	9,435
Total IBNR
Cumulative number of reported claims | Claim	613
Cumulative Paid	$ 11,935	11,702	11,620	11,137	10,650	10,147	8,622	7,643	6,211	3,979
Accident Year 2013 | Personal Lines
Claims Development [Line Items]
Incurred	19,365	19,227	19,226	19,222	19,202	19,167	19,138	18,925	17,996	18,034
Total IBNR	$ 0
Cumulative number of reported claims | Claim	5,208
Cumulative Paid	$ 19,365	19,227	19,222	19,214	19,174	19,014	18,600	18,052	15,883	$ 9,955
Accident Year 2014
Claims Development [Line Items]
Incurred	47,063	47,272	47,140	46,848	46,074	44,247	40,446	37,378	37,660
Total IBNR
Cumulative number of reported claims | Claim	5,491
Cumulative Paid	$ 46,633	46,718	46,457	45,591	43,464	40,192	34,718	30,492	21,534
Accident Year 2014 | Commercial Lines
Claims Development [Line Items]
Incurred	29,011	29,175	29,045	28,766	28,145	26,367	22,711	19,907	19,709
Total IBNR
Cumulative number of reported claims | Claim	1,754
Cumulative Paid	$ 28,608	28,648	28,389	27,544	25,609	22,446	17,458	13,977	8,715
Accident Year 2014 | Personal Lines
Claims Development [Line Items]
Incurred	18,052	18,097	18,095	18,082	17,929	17,880	17,735	17,471	17,951
Total IBNR	$ 0
Cumulative number of reported claims | Claim	3,737
Cumulative Paid	$ 18,025	18,070	18,068	18,047	17,855	17,746	17,260	16,515	$ 12,819
Accident Year 2015
Claims Development [Line Items]
Incurred	54,541	54,251	53,222	51,736	49,763	46,581	40,078	33,319
Total IBNR	$ 26
Cumulative number of reported claims | Claim	4,513
Cumulative Paid	$ 54,129	52,979	51,123	49,747	45,634	36,393	29,690	18,241
Accident Year 2015 | Commercial Lines
Claims Development [Line Items]
Incurred	39,093	38,824	37,795	36,372	34,478	31,861	26,633	22,442
Total IBNR	$ 26
Cumulative number of reported claims | Claim	2,361
Cumulative Paid	$ 38,685	37,563	35,833	34,497	30,475	22,549	17,817	10,470
Accident Year 2015 | Personal Lines
Claims Development [Line Items]
Incurred	15,448	15,427	15,427	15,364	15,285	14,721	13,445	10,877
Total IBNR	$ 0
Cumulative number of reported claims | Claim	2,152
Cumulative Paid	$ 15,444	15,416	15,290	15,250	15,159	13,844	11,873	$ 7,771
Accident Year 2016
Claims Development [Line Items]
Incurred	64,356	62,627	61,744	59,905	55,389	48,353	44,015
Total IBNR	$ 201
Cumulative number of reported claims | Claim	5,371
Cumulative Paid	$ 62,636	59,096	57,296	53,077	42,227	30,373	17,374
Accident Year 2016 | Commercial Lines
Claims Development [Line Items]
Incurred	48,677	46,993	46,089	44,355	40,440	34,935	32,396
Total IBNR	$ 201
Cumulative number of reported claims | Claim	3,557,000
Cumulative Paid	$ 46,957	43,644	41,945	37,967	27,785	19,135	10,255
Accident Year 2016 | Personal Lines
Claims Development [Line Items]
Incurred	15,679	15,634	15,655	15,550	14,949	13,418	11,619
Total IBNR	$ 0
Cumulative number of reported claims | Claim	1,814
Cumulative Paid	$ 15,679	15,452	15,351	15,110	14,442	11,238	$ 7,119
Accident Year 2017
Claims Development [Line Items]
Incurred	71,606	70,500	66,676	64,242	58,045	58,309
Total IBNR	$ 671
Cumulative number of reported claims | Claim	8,749
Cumulative Paid	$ 67,757	62,014	56,834	48,209	35,964	20,768
Accident Year 2017 | Commercial Lines
Claims Development [Line Items]
Incurred	56,649	55,589	51,883	49,749	44,495	44,251
Total IBNR	$ 671
Cumulative number of reported claims | Claim	5,832
Cumulative Paid	$ 52,800	47,148	42,308	34,205	23,020	12,448
Accident Year 2017 | Personal Lines
Claims Development [Line Items]
Incurred	14,957	14,911	14,793	14,493	13,550	14,058
Total IBNR	$ 0
Cumulative number of reported claims | Claim	2,917
Cumulative Paid	$ 14,957	14,866	14,526	14,004	12,944	$ 8,320
Accident Year 2018
Claims Development [Line Items]
Incurred	66,400	61,643	56,024	48,810	48,517
Total IBNR	$ 1,637
Cumulative number of reported claims | Claim	6,927
Cumulative Paid	$ 56,752	47,819	37,733	25,417	14,671
Accident Year 2018 | Commercial Lines
Claims Development [Line Items]
Incurred	60,102	55,261	49,741	42,432	42,624
Total IBNR	$ 1,637
Cumulative number of reported claims | Claim	6,124
Cumulative Paid	$ 50,508	41,577	31,633	19,799	10,375
Accident Year 2018 | Personal Lines
Claims Development [Line Items]
Incurred	6,298	6,382	6,283	6,378	5,893
Total IBNR	$ 0
Cumulative number of reported claims | Claim	803
Cumulative Paid	$ 6,244	6,242	6,100	5,618	$ 4,296
Accident Year 2019
Claims Development [Line Items]
Incurred	58,125	49,227	44,841	44,385
Total IBNR	$ 4,529
Cumulative number of reported claims | Claim	6,662
Cumulative Paid	$ 42,743	31,650	23,066	12,197
Accident Year 2019 | Commercial Lines
Claims Development [Line Items]
Incurred	55,263	46,329	42,129	41,286
Total IBNR	$ 4,529
Cumulative number of reported claims | Claim	6,320,000
Cumulative Paid	$ 39,893	28,958	20,462	10,078
Accident Year 2019 | Personal Lines
Claims Development [Line Items]
Incurred	2,862	2,898	2,712	3,099
Total IBNR	$ 0
Cumulative number of reported claims | Claim	342
Cumulative Paid	$ 2,850	2,692	2,604	$ 2,119
Accident Year 2020
Claims Development [Line Items]
Incurred	41,829	37,918	36,206
Total IBNR	$ 3,787
Cumulative number of reported claims | Claim	4,196
Cumulative Paid	$ 26,830	19,787	11,524
Accident Year 2020 | Commercial Lines
Claims Development [Line Items]
Incurred	39,193	35,328	33,867
Total IBNR	$ 3,787
Cumulative number of reported claims | Claim	3,830
Cumulative Paid	$ 24,225	17,332	10,217
Accident Year 2020 | Personal Lines
Claims Development [Line Items]
Incurred	2,636	2,590	2,339
Total IBNR	$ 0
Cumulative number of reported claims | Claim	366
Cumulative Paid	$ 2,605	2,455	$ 1,307
Accident Year 2021
Claims Development [Line Items]
Incurred	46,598	44,797
Total IBNR	$ 8,860
Cumulative number of reported claims | Claim	3,441
Cumulative Paid	$ 25,293	15,892
Accident Year 2021 | Commercial Lines
Claims Development [Line Items]
Incurred	42,266	40,388
Total IBNR	$ 8,744
Cumulative number of reported claims | Claim	2,861
Cumulative Paid	$ 21,313	12,870
Accident Year 2021 | Personal Lines
Claims Development [Line Items]
Incurred	4,332	4,409
Total IBNR	$ 116
Cumulative number of reported claims | Claim	580
Cumulative Paid	$ 3,980	$ 3,022
Accident Year 2022
Claims Development [Line Items]
Incurred	51,112
Total IBNR	$ 17,494
Cumulative number of reported claims | Claim	2,617
Cumulative Paid	$ 18,236
Accident Year 2022 | Commercial Lines
Claims Development [Line Items]
Incurred	41,708
Total IBNR	16,067
Cumulative number of reported claims | Claim		1,965
Cumulative Paid	12,839
Accident Year 2022 | Personal Lines
Claims Development [Line Items]
Incurred	9,404
Total IBNR	$ 1,427
Cumulative number of reported claims | Claim	652
Cumulative Paid	$ 5,397

Unpaid Losses and Loss Adjust_6

Unpaid Losses and Loss Adjustment Expenses - Reconciliation of Loss to the Liability for Claims (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020	Dec. 31, 2019
Short-duration Insurance Contracts, Reconciliation of Claims Development to Liability [Line Items]
Unpaid losses and ALAE, net of reinsurance	$ 74,996
Reinsurance recoverables on unpaid losses	82,651	$ 40,344	$ 24,218	$ 22,579
ULAE expense	7,892
Total gross unpaid losses and LAE	165,539	$ 139,085	$ 111,270	$ 107,246
Commercial Lines
Short-duration Insurance Contracts, Reconciliation of Claims Development to Liability [Line Items]
Unpaid losses and ALAE, net of reinsurance	70,509
Reinsurance recoverables on unpaid losses	81,301
Personal Lines
Short-duration Insurance Contracts, Reconciliation of Claims Development to Liability [Line Items]
Unpaid losses and ALAE, net of reinsurance	4,487
Reinsurance recoverables on unpaid losses	$ 1,350

Unpaid Losses and Loss Adjust_7

Unpaid Losses and Loss Adjustment Expenses - Loss Duration (Details)	Dec. 31, 2022
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]
Year 1	35.70%
Year 2	22.80%
Year 3	17.50%
Year 4	9.70%
Year 5	7.70%
Year 6	3.50%
Year 7	1.70%
Year 8	0.80%
Year 9	0.40%
Year 10, and onwards	0.20%
Commercial Lines
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]
Year 1	34.40%
Year 2	23%
Year 3	17.70%
Year 4	10%
Year 5	8%
Year 6	3.60%
Year 7	1.80%
Year 8	0.80%
Year 9	0.40%
Year 10, and onwards	0.30%
Personal Lines
Short-duration Insurance Contracts, Historical Claims Duration [Line Items]
Year 1	69.40%
Year 2	16.60%
Year 3	10.10%
Year 4	2.60%
Year 5	0.90%
Year 6	0.20%
Year 7	0.10%
Year 8	0.10%
Year 9	0%
Year 10, and onwards	0%

Reinsurance - Narrative (Detail

Reinsurance - Narrative (Details) - USD ($)			3 Months Ended	12 Months Ended			36 Months Ended		48 Months Ended
	Nov. 01, 2022	Jan. 01, 2022	Mar. 31, 2021	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2022	Jun. 30, 2022	Dec. 31, 2019
Effects Of Reinsurance [Line Items]
Reinsurance recoverables on paid losses				$ 6,653,000	$ 1,347,000		$ 6,653,000	$ 1,347,000	$ 6,653,000
Stated net reserves retained				82,888,000	98,741,000	$ 87,052,000	82,888,000	98,741,000	82,888,000		$ 84,667,000
Losses and loss adjustment expenses, net				81,440,000	69,861,000	56,228,000
Reinsurance recoverables on unpaid losses				82,651,000	40,344,000	24,218,000	82,651,000	40,344,000	82,651,000		$ 22,579,000
Prior period				24,284,000	19,432,000	15,594,000
Prepaid reinsurance premiums				16,399,000	8,301,000		16,399,000	8,301,000	16,399,000
Assumed premiums written				42,187,000	34,294,000	28,905,000
Ceded premium written				46,787,000	30,666,000	18,395,000
Ceded premiums earned				38,690,000	24,248,000	17,511,000
Winter Storm Uri
Effects Of Reinsurance [Line Items]
Losses and loss adjustment expenses, net			$ 2,000,000
Ceded premium written					340,000
Ceded premiums earned					340,000
Hurricane
Effects Of Reinsurance [Line Items]
Ceded premium written				1,600,000	86,000	195,000
Ceded premiums earned				1,600,000	86,000	195,000
Accident Year 2019
Effects Of Reinsurance [Line Items]
Prior period				9,600,000
Loss Portfolio Transfer (“LPT”) Reinsurance Agreement
Effects Of Reinsurance [Line Items]
Reinsurance recoverables on paid losses				3,800,000			3,800,000		3,800,000
Reinsurance recoverables on unpaid losses				25,900,000			25,900,000		25,900,000
100% Cede of Commercial Liability Risks In Excess of $400,000
Effects Of Reinsurance [Line Items]
Amount retained (excess of)				340,000	400,000	400,000
Ceded Commercial Property Risks In Excess of $200,000
Effects Of Reinsurance [Line Items]
Amount retained (excess of)				300,000
Ceded Commercial Property Risks In Excess of $400,000
Effects Of Reinsurance [Line Items]
Amount retained (excess of)					200,000
40% Cede of Commercial Liability Risks In Excess of $400,000
Effects Of Reinsurance [Line Items]
Amount retained (excess of)						$ 400,000
Reinsurance retention policy, reinsured percentage						40%
60% Cede of Commercial Liability Risks In Excess of $300,000
Effects Of Reinsurance [Line Items]
Amount retained (excess of)						$ 300,000
Reinsurance retention policy, reinsured percentage						60%
Ceded Homeowners Specific Risks In Excess of $300,000
Effects Of Reinsurance [Line Items]
Amount retained (excess of)				300,000	$ 300,000	$ 300,000
Property Risk | Property, Liability and Casualty Insurance Product Line
Effects Of Reinsurance [Line Items]
Amount retained (excess of)				300,000
Amount reinsured				7,700,000
Liability Risk
Effects Of Reinsurance [Line Items]
Percentage of ceding commission		40%			40%
Workers Compensation and Casualty Clash
Effects Of Reinsurance [Line Items]
Amount retained (excess of)				1,000,000				1,000,000
Amount reinsured				29,000,000				19,000,000
Casualty Clash
Effects Of Reinsurance [Line Items]
Amount retained (excess of)					$ 20,000,000
Reinsurance retention policy, reinsured percentage					87%
Amount reinsured					$ 10,000,000
Commercial Auto Physical Damage Risk
Effects Of Reinsurance [Line Items]
Amount retained (excess of)				400,000
Liability Reinsurance Policy
Effects Of Reinsurance [Line Items]
Amount retained (excess of)									400,000
Amount reinsured									$ 600,000
Property Reinsurance Policy | Homeowners Lines
Effects Of Reinsurance [Line Items]
Amount reinsured							1,700,000
Property Reinsurance Policy | Commercial Lines
Effects Of Reinsurance [Line Items]
Amount retained (excess of)					200,000	300,000
Amount reinsured					7,800,000	7,700,000
Property Reinsurance Policy | Property, Liability and Casualty Insurance Product Line
Effects Of Reinsurance [Line Items]
Amount retained (excess of)				2,000,000	2,000,000	2,000,000
Insured property value				$ 28,000,000	$ 28,000,000	$ 28,000,000
Termination date				Jun. 01, 2023	Jun. 01, 2022	Jun. 01, 2021
Property Reinsurance Policy | Maximum | Homeowners Lines
Effects Of Reinsurance [Line Items]
Amount retained (excess of)							$ 300,000
Multiple Line Reinsurance Policy | Commercial Lines
Effects Of Reinsurance [Line Items]
Amount retained (excess of)								400,000
Amount reinsured								$ 600,000
Quota Share Reinsurance Agreement | Minimum | Commercial Lines
Effects Of Reinsurance [Line Items]
Reinsurance retention policy, reinsured percentage					90%
Quota Share Reinsurance Agreement | Maximum | Commercial Lines
Effects Of Reinsurance [Line Items]
Reinsurance retention policy, reinsured percentage					100%
Quota Share Reinsurance Agreement, Other Arrangements | Maximum | Other insurance product line
Effects Of Reinsurance [Line Items]
Reinsurance retention policy, reinsured percentage				100%
Insurance Fronting Arrangement
Effects Of Reinsurance [Line Items]
Assumed premiums written				$ 42,200,000	$ 34,300,000	$ 28,900,000
Fleming Reinsurance Ltd | Loss Portfolio Transfer (“LPT”) Reinsurance Agreement
Effects Of Reinsurance [Line Items]
Stated net reserves retained										$ 40,800,000
Losses and loss adjustment expenses, net	$ 5,500,000
One-time risk fee retained										5,400,000
Amount reinsured	40,800,000
Fleming Reinsurance Ltd | Loss Portfolio Transfer (“LPT”) Reinsurance Agreement | Accident Year 2019
Effects Of Reinsurance [Line Items]
Reinsurance recoverables on paid losses										66,300,000
Stated net reserves retained										$ 40,800,000
Prior period	20,000,000
Fleming Reinsurance Ltd | Minimum | Loss Portfolio Transfer (“LPT”) Reinsurance Agreement
Effects Of Reinsurance [Line Items]
Reinsurance recoverables on paid losses	46,300,000
Fleming Reinsurance Ltd | Maximum | Loss Portfolio Transfer (“LPT”) Reinsurance Agreement
Effects Of Reinsurance [Line Items]
Reinsurance recoverables on paid losses	$ 66,300,000
Corridor | Agreement between CIC and WPIC and Fleming Re
Effects Of Reinsurance [Line Items]
Losses and loss adjustment expenses, net				5,500,000
Layer | Minimum | Agreement between CIC and WPIC and Fleming Re
Effects Of Reinsurance [Line Items]
Losses and loss adjustment expenses, net				644,000
Layer | Maximum | Agreement between CIC and WPIC and Fleming Re
Effects Of Reinsurance [Line Items]
Losses and loss adjustment expenses, net				$ 20,000,000

Reinsurance - Effects of Reinsu

Reinsurance - Effects of Reinsurance and Assumption Transactions (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Written premiums:
Direct	$ 95,832	$ 97,801	$ 82,430
Assumed	42,187	34,294	28,905
Ceded	(46,787)	(30,666)	(18,395)
Net written premiums	91,232	101,429	92,940
Earned premiums:
Direct	97,843	91,943	75,130
Assumed	37,558	31,107	31,484
Ceded	(38,690)	(24,248)	(17,511)
Net earned premiums	96,711	98,802	89,103
Loss and loss adjustment expenses:
Direct	73,000	71,021	48,780
Assumed	43,487	25,740	24,429
Ceded	(35,047)	(26,900)	(16,981)
Total net incurred losses and LAE	$ 81,440	$ 69,861	$ 56,228

Debt - Narrative (Details)

Debt - Narrative (Details) - USD ($)			12 Months Ended
	Apr. 24, 2020	Sep. 24, 2018	Dec. 31, 2022
Paycheck Protection Program
Debt Instrument [Line Items]
Debt	$ 2,700,000
Debt instrument, description	The Company received notice from the SBA that the loan was 100% forgiven, including accrued interest, on July 8, 2021. This resulted in a $2.8 million gain that is included in Other Gains on the Consolidated Statement of Operations in 2021
Loan forgiven date	Jul. 08, 2021
Paycheck Protection Program | Other Gains
Debt Instrument [Line Items]
Gain on forgiven loan	$ 2,800,000
Senior Unsecured Notes | Senior Unsecured Notes
Debt Instrument [Line Items]
Face amount of debt		$ 25,300,000	$ 24,400,000
Maturity date		Sep. 30, 2023
Interest rate		6.75%
Number of units repurchased			0
Debt issuance costs			$ 195,000
Line of credit
Debt Instrument [Line Items]
Borrowing capacity			$ 10,000,000
Line of credit | LIBOR
Debt Instrument [Line Items]
Variable interest rate			2.75%
Subordinated notes | Subordinated notes
Debt Instrument [Line Items]
Face amount of debt		$ 10,500,000	$ 10,500,000
Maturity date		Sep. 30, 2038
Interest rate, payment terms			Interest is payable quarterly at the end of March, June, September and December
Call premium percentage		12.50%
Debt issuance costs			$ 810,000
Subordinated notes | Subordinated notes | Debt Instrument, Redemption, Period One
Debt Instrument [Line Items]
Interest rate		7.50%
Call premium		$ 1,100,000
Subordinated notes | Subordinated notes | Debt Instrument, Redemption, Period Two
Debt Instrument [Line Items]
Interest rate		12.50%
Call premium		$ 1,750,000
Subordinated notes | Subordinated notes | Debt Instrument, Redemption, Period Three
Debt Instrument [Line Items]
Call premium		$ 3,050,000

Debt - Outstanding Senior Debt

Debt - Outstanding Senior Debt (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021	Apr. 24, 2020
Debt Instrument [Line Items]
Debt	$ 33,876	$ 33,564
Paycheck Protection Program
Debt Instrument [Line Items]
Debt			$ 2,700
Senior Unsecured Notes
Debt Instrument [Line Items]
Debt	24,186	23,926
Subordinated notes
Debt Instrument [Line Items]
Debt	$ 9,690	$ 9,638

Income Taxes - Narrative (Detai

Income Taxes - Narrative (Details) - USD ($)	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020	Oct. 13, 2022
Operating Loss Carryforwards [Line Items]
Current income tax payable		$ 34,000
Current income tax receivable	$ 58,000
Effective income tax rate	21%	21%	21%
Valuation allowance	$ 21,663,000	$ 14,594,000
Domestic Tax Authority | Internal Revenue Service (IRS)
Operating Loss Carryforwards [Line Items]
Net operating loss carryforwards	65,600,000
Net operating loss carryforwards, subject to expiration	50,400,000
Net operating loss carryforwards, not subject to expiration	15,200,000
Net operating loss carryforwards subject to limitations	7,600,000
State Tax Authority
Operating Loss Carryforwards [Line Items]
Net operating loss carryforwards	$ 107,200,000			$ 14,800,000
State Tax Authority | Minimum
Operating Loss Carryforwards [Line Items]
Income tax statute of limitations period	3 years
State Tax Authority | Maximum
Operating Loss Carryforwards [Line Items]
Income tax statute of limitations period	4 years

Income Taxes - Income Tax Expen

Income Taxes - Income Tax Expense (Benefit) (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Income Tax Disclosure [Abstract]
Current tax expense (benefit)	$ (45)	$ 208	$ 6
Deferred tax expense (benefit)	(9,396)	0	0
Total income tax expense (benefit)	$ (9,441)	$ 208	$ 6

Income Taxes - Effective Income

Income Taxes - Effective Income Tax Reconciliation (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Income Tax Disclosure [Abstract]
Income (loss) before income taxes	$ (20,490)	$ (1,710)	$ (238)
Statutory U.S. federal income tax rate	(4,303)	(359)	(50)
State income taxes, net of federal benefit	(5,984)	174	44
Tax‑exempt investment income and dividend received deduction	(22)	(40)	(50)
Nondeductible meals and entertainment	79	33	23
Valuation allowance on deferred tax assets	3,715	676	(205)
Equity-earnings from Affiliate	195	170	88
Net gain from sale of agency assets	(2,848)	0	0
Utilization of state NOLs	(386)	0	0
PPP Loan forgiveness	0	(578)	0
Other	113	132	156
Total income tax expense (benefit)	$ (9,441)	$ 208	$ 6
Effective tax rate	46.10%	(12.20%)	(2.60%)

Income Taxes - Components of De

Income Taxes - Components of Deferred Tax Assets and Liabilities (Details) - USD ($)	Dec. 31, 2022	Dec. 31, 2021
Deferred tax assets:
Discounted unpaid losses and loss adjustment expenses	$ 1,217,000	$ 1,555,000
Unearned premiums	2,324,000	2,561,000
Net operating loss carryforwards	12,152,000	12,544,000
Net unrealized losses on investments	3,687,000	418,000
State net operating loss carryforwards	5,097,000	822,000
Other	403,000	102,000
Gross deferred tax assets	24,880,000	18,002,000
Less valuation allowance	(21,663,000)	(14,594,000)
Total deferred tax assets, net of allowance	3,217,000	3,408,000
Deferred tax liabilities:
Investment basis difference	23,000	15,000
Tax rate change transition discounting	137,000	183,000
Equity investment in Affiliate	691,000	470,000
Net unrealized gains on investments	0	0
Deferred policy acquisition costs	2,161,000	2,576,000
Intangible assets	115,000	115,000
Property and equipment	41,000	47,000
Other	49,000	2,000
Total deferred tax liabilities	3,217,000	$ 3,408,000
Net deferred tax liability	$ 0

Statutory Financial Data, Ris_3

Statutory Financial Data, Risk-Based Capital and Dividend Restrictions - Summary of Statutory Basis Information (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
CIC
Statutory Accounting Practices [Line Items]
Statutory capital and surplus	$ 47,827	$ 50,194	$ 49,271
RBC authorized control level	15,541	15,868	14,221
Statutory net income (loss)	$ (6,846)	$ (9,161)	$ 2,059
RBC %	308%	316%	346%
WPIC
Statutory Accounting Practices [Line Items]
Statutory capital and surplus	$ 20,651	$ 23,603	$ 24,723
RBC authorized control level	5,098	5,331	4,547
Statutory net income (loss)	$ (4,171)	$ (614)	$ 1,024
RBC %	405%	443%	544%

Statutory Financial Data, Ris_4

Statutory Financial Data, Risk-Based Capital and Dividend Restrictions - Narrative (Details)	12 Months Ended
	Dec. 31, 2022
Insurance [Abstract]
Dividend restriction percentage of statutory surplus of preceding year	10%

Shareholders' Equity - Narrativ

Shareholders' Equity - Narrative (Details)		12 Months Ended
	Aug. 10, 2022 USD ($) $ / shares shares	Dec. 31, 2022 USD ($) Vote shares	Dec. 31, 2021 USD ($) shares
Equity Class Of Treasury Stock [Line Items]
Additional paid in capital due to stock repurchase | $		$ 10,000
Cash returned from stock repurchase program | $		$ 14,000
Common stock, shares issued (in shares)		12,215,849	9,707,817
Common stock, shares outstanding (in shares)		12,215,849	9,707,817
Common stock voting rights, number of votes per share | Vote		1
Restricted Stock Units (RSUs)
Equity Class Of Treasury Stock [Line Items]
Shares repurchased (in shares)		1,968	3,886
Shares repurchased | $		$ 4,000	$ 12,000
Common stocks
Equity Class Of Treasury Stock [Line Items]
Common stock, shares issued (in shares)		12,215,849	9,707,817
Common stock, shares outstanding (in shares)		12,215,849	9,707,817
Private placement | Common stocks
Equity Class Of Treasury Stock [Line Items]
Common equity issued | $	$ 5,000,000
Common equity issued (in shares)	2,500,000
Offering price per share (in dollars per share) | $ / shares	$ 2

Accumulated Other Comprehensi_3

Accumulated Other Comprehensive Income (Loss) - Accumulated Other Comprehensive Income (Loss) (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
AOCI Attributable to Parent, Net of Tax [Roll Forward]
Balance at beginning of period	$ 40,503	$ 44,413	$ 42,725
Other comprehensive income (loss)	(16,093)	(3,022)	423
Balance at end of period	18,950	40,503	44,413
Accumulated Other Comprehensive Income (Loss)
AOCI Attributable to Parent, Net of Tax [Roll Forward]
Balance at beginning of period	(2,110)	912	489
Other comprehensive income (loss) before reclassifications	(16,024)	(2,937)
Less: amounts reclassified from accumulated other comprehensive income (loss)	69	85
Other comprehensive income (loss)	(16,093)	(3,022)	423
Balance at end of period	$ (18,203)	$ (2,110)	$ 912

Earnings Per Share - Basic and

Earnings Per Share - Basic and Diluted Income (Loss) Per Common Share (Details) - USD ($) $ / shares in Units, $ in Thousands		12 Months Ended
		Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Earnings Per Share [Abstract]
Net income (loss)		$ (10,681)	$ (1,094)	$ 595
Weighted average common shares outstanding, basic	[1]	10,692,090	9,691,998	9,625,059
Weighted average common shares outstanding, diluted	[1]	10,692,090	9,691,998	9,625,059
Earnings (loss) per share, basic		$ (1)	$ (0.11)	$ 0.06
Earnings (loss) per share, diluted		$ (1)	$ (0.11)	$ 0.06
[1] The non-vested shares of the restricted stock units and stock options were anti-dilutive as of December 31, 2022, 2021, and 2020. Therefore, the non-vested shares are excluded from earnings (loss) per share for the years ended December 31, 2022, 2021, and 2020 .

Stock-based Compensation - Narr

Stock-based Compensation - Narrative (Details) - USD ($)		6 Months Ended	12 Months Ended
	Mar. 08, 2022	Jun. 30, 2020	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020	Dec. 31, 2018	Dec. 31, 2016
Stock Option
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Options issued to purchase shares of common stock	630,000	280,000
Vesting period	5 years	5 years
Strike price	$ 4.53	$ 3.81
Expiration date	Mar. 08, 2032	Jun. 30, 2030
Estimated fair value of options issued to purchase shares of common stock	$ 612,000
Estimated value of options issued to purchase shares of common stock		$ 290,000
Stock options volatility rate	65.04%
Options exercisable term	5 years
Risk free interest rate of options	1.80%
Risk free interest rate term of options	5 years
Market value of stock	$ 2.40
Stock Option | Stock Options Granted on June 30, 2020 [Member]
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense			$ 29,000	$ 52,000	$ 53,000
Share-based compensation expense not yet recognized			$ 132,000
Share-based compensation nonvested shares			153,000
Stock Option | Stock Options Granted on March 8, 2022 [Member]
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense			$ 102,000
Share-based compensation expense not yet recognized			$ 510,000
Share-based compensation nonvested shares			630,000
Restricted Stock Units (RSUs)
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Share-based compensation expense			$ 56,000	$ 166,000	$ 677,000
Share-based compensation expense not yet recognized			$ 17,000
Restricted Stock Units (RSUs) | 2015 Omnibus Incentive Plan
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares granted in period (in shares)						70,000	111,281
Shares granted in period						$ 404,000	$ 909,000
Share-based compensation nonvested shares			9,000

Related Party Transactions - Na

Related Party Transactions - Narrative (Details) $ in Millions	Oct. 13, 2022 USD ($)
Venture
Related Party Transaction [Line Items]
Total consideration	$ 9.7

Employee Benefit Plans (Details

Employee Benefit Plans (Details) - USD ($)	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Retirement Benefits [Abstract]
Minimum employee contribution amount, percentage of gross compensation	1%
Maximum employee contribution amount, percentage of gross compensation	100%
Employee matching contribution, percentage of employee gross compensation	4%
Plan expense	$ 457,000	$ 508,000	$ 508,000

Commitments and Contingencies (

Commitments and Contingencies (Details)	Dec. 31, 2022 USD ($)
Agreement to Design and Implement New Systems
Other Commitments [Line Items]
Minimum monthly payment	$ 30,000

Segment Information - Narrative

Segment Information - Narrative (Details) - Business	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Segment Reporting Information [Line Items]
Number of businesses	3
Gross Written Premiums | Geographic Concentration Risk | Michigan, Florida, Texas and Pennsylvania
Segment Reporting Information [Line Items]
Concentration risk	54.10%	50.60%	49.60%

Segment Information - Summary o

Segment Information - Summary of Net Earned Premiums by Segment (Details) - Net Earned Premium - Operating Segments - Product Concentration	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Segment Reporting Information [Line Items]
Net Earned Premium	100%	100%	100%
Commercial Lines
Segment Reporting Information [Line Items]
Net Earned Premium	84%	89%	92%
Personal Lines
Segment Reporting Information [Line Items]
Net Earned Premium	16%	11%	8%

Segment Information - Informati

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)

Schedule II - Condensed Finan_2

Schedule II - Condensed Financial Information of Registrant - Balance Sheets (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020	Dec. 31, 2019
Assets
Due from Affiliate	$ 1,261	$ 5,784
Other assets	7,862	8,524
Total assets	312,350	290,404
Liabilities:
Debt	33,876	33,564
Total liabilities	293,400	249,901
Shareholders' equity:
Common stock, no par value (100,000,000 shares authorized; 12,215,849 and 9,707,817 issued and outstanding, respectively)	97,913	92,692
Accumulated deficit	(60,760)	(50,079)
Accumulated other comprehensive income (loss)	(18,203)	(2,110)
Total shareholders' equity	18,950	40,503	$ 44,413	$ 42,725
Total liabilities and shareholders' equity	312,350	290,404
Parent Company
Assets
Investment in subsidiaries	56,670	79,511
Cash	9,022	750
Due from subsidiaries	(9,754)	(7,055)
Due from Affiliate	113	220
Other assets	2,434	2,522
Total assets	58,485	75,948
Liabilities:
Debt	33,876	33,564
Other liabilities	5,659	1,881
Total liabilities	39,535	35,445
Shareholders' equity:
Common stock, no par value (100,000,000 shares authorized; 12,215,849 and 9,707,817 issued and outstanding, respectively)	97,913	92,692
Accumulated deficit	(60,760)	(50,079)
Accumulated other comprehensive income (loss)	(18,203)	(2,110)
Total shareholders' equity	18,950	40,503
Total liabilities and shareholders' equity	$ 58,485	$ 75,948

Schedule II - Condensed Finan_3

Schedule II - Condensed Financial Information of Registrant - Balance Sheets Stock Information (Details) - $ / shares	Dec. 31, 2022	Dec. 31, 2021
Condensed Balance Sheet Statements, Captions [Line Items]
Common stock, shares authorized (in shares)	100,000,000	100,000,000
Common stock, shares issued (in shares)	12,215,849	9,707,817
Common stock, shares outstanding (in shares)	12,215,849	9,707,817
Parent Company
Condensed Balance Sheet Statements, Captions [Line Items]
Common stock, par value (in dollars per share)	$ 0	$ 0
Common stock, shares authorized (in shares)	100,000,000	100,000,000
Common stock, shares issued (in shares)	12,215,849	9,707,817
Common stock, shares outstanding (in shares)	12,215,849	9,707,817

Schedule II - Condensed Finan_4

Schedule II - Condensed Financial Information of Registrant - Statements of Comprehensive Income (Loss) (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Revenue and Other Income
Revenue	$ 104,889	$ 115,963	$ 103,488
Other income	2,768	2,671	2,615
Expenses
Operating expenses	18,789	16,509	18,468
Interest expense	2,971	2,852	2,925
Total expenses	125,379	117,673	103,726
Income tax expense (benefit)	(9,441)	208	6
Net income (loss)	(10,681)	(1,094)	595
Other Comprehensive Income
Other comprehensive income (loss)	(16,093)	(3,022)	423
Parent Company
Revenue and Other Income
Revenue	5,170	18,852	13,010
Other income	190	2,900	483
Expenses
Operating expenses	14,365	12,736	14,459
Interest expense	2,816	2,852	2,925
Total expenses	17,181	15,588	17,384
Income (loss) before equity in earnings (losses) of subsidiaries and income tax expense (benefit)	(12,011)	3,264	(4,374)
Income tax expense (benefit)	(4,078)	156	(813)
Income (loss) before equity earnings (losses) of subsidiaries	(7,933)	3,108	(3,561)
Equity earnings (losses) in subsidiaries	(2,748)	(4,202)	4,156
Net income (loss)	(10,681)	(1,094)	595
Other Comprehensive Income
Other comprehensive income (loss)	(16,093)	(3,022)	423
Total Comprehensive income (loss)	(26,774)	(4,116)	1,018
Parent Company | Management fees from subsidiaries
Revenue and Other Income
Revenue	$ 4,980	$ 15,952	$ 12,527

Schedule II - Condensed Finan_5

Schedule II - Condensed Financial Information of Registrant - Statement of Cash Flows (Details) - USD ($)		12 Months Ended
		Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Cash Flows from Operating Activities
Net income (loss)		$ (10,681,000)	$ (1,094,000)	$ 595,000
Adjustments to reconcile net income (loss) to net cash used in operating activities:
Depreciation and amortization		417,000	423,000	437,000
Stock-based compensation expense		(368,000)	(824,000)	(839,000)
Deferred income tax expense		(9,396,000)	0	0
Other (gain) loss		(59,000)	(11,664,000)	(260,000)
Changes in operating assets and liabilities:
Other assets		(138,000)	949,000	908,000
Net cash provided by operating activities		(40,474,000)	5,355,000	2,982,000
Cash Flows From Investing Activities
Contributions to subsidiaries	[1]	(1,947,000)
Purchases of investments		(318,227,000)	(226,794,000)	(391,588,000)
Net cash provided by (used in) investing activities		56,503,000	1,377,000	(7,337,000)
Cash Flows From Financing Activities
Proceeds received from issuance of shares of common stock		5,000,000
Repurchase of common stock		10,000	(12,000)	(36,000)
Net cash provided by (used in) financing activities		2,093,000	(5,012,000)	5,084,000
Net increase (decrease) in cash		18,122,000	1,720,000	729,000
Cash at beginning of period		9,913,000	8,193,000	7,464,000
Cash at end of period		28,035,000	9,913,000	8,193,000
Supplemental Disclosure of Cash Flow Information:
Interest paid		2,979,000	2,883,000	2,586,000
Parent Company
Cash Flows from Operating Activities
Net income (loss)		(10,681,000)	(1,094,000)	595,000
Adjustments to reconcile net income (loss) to net cash used in operating activities:
Depreciation and amortization		436,000	415,000	421,000
Equity in undistributed (income) loss of subsidiaries		2,748,000	4,202,000	(4,156,000)
Stock-based compensation expense		211,000	218,000	706,000
Deferred income tax expense		3,884,000
Other (gain) loss			(2,593,000)	(260,000)
Changes in operating assets and liabilities:
Due from subsidiaries		2,699,000	8,800,000	(852,000)
Due from Affiliate		107,000	(220,000)	214,000
Current income tax recoverable		0	0	539,000
Other assets		62,000	890,000	625,000
Other liabilities		(203,000)	(915,000)	(715,000)
Net cash provided by operating activities		(737,000)	9,703,000	(2,883,000)
Cash Flows From Investing Activities
Contributions to subsidiaries		4,000,000	(5,400,000)	(1,150,000)
Dividends received from subsidiaries		0	0	0
Purchases of investments		0	0	(79,000)
Purchases of property and equipment		0	(20,000)	0
Net cash provided by (used in) investing activities		4,000,000	(5,420,000)	(1,229,000)
Cash Flows From Financing Activities
Proceeds received from issuance of shares of common stock		5,000,000	0	0
Repurchase of common stock		10,000	(12,000)	(36,000)
Borrowings under debt arrangements		5,000,000	3,000,000	5,745,000
Repayment of lines of credit		(5,000,000)	(8,000,000)	(625,000)
Stock and debt issuance costs		0	0	0
Net cash provided by (used in) financing activities		5,010,000	(5,012,000)	5,084,000
Net increase (decrease) in cash		8,273,000	(729,000)	972,000
Cash at beginning of period		749,000	1,478,000	506,000
Cash at end of period		9,022,000	749,000	1,478,000
Supplemental Disclosure of Cash Flow Information:
Interest paid		$ 2,979,000	$ 2,883,000	$ 2,586,000
[1] See Note 2 ~ VSRM Transaction

Schedule II - Condensed Finan_6

Schedule II - Condensed Financial Information of Registrant - Additional Information (Details) - USD ($)	3 Months Ended	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Guarantee of debt
Condensed Cash Flow Statements Captions [Line Items]
Guarantee obligation	$ 10,000,000	$ 10,000,000
Interest rate	4%	4%
Parent Company
Condensed Cash Flow Statements Captions [Line Items]
Dividends received from subsidiaries during period		$ 0	$ 0	$ 0
Non-cash dividend received from subsidiary			$ 6,000,000
Parent Company | Sycamore
Condensed Cash Flow Statements Captions [Line Items]
Dividends received from subsidiaries during period	$ 10,800,000

Schedule V - Valuation and Qu_2

Schedule V - Valuation and Qualifying Accounts (Details) - Valuation for Deferred Tax Assets - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
SEC Schedule, 12-09, Movement in Valuation Allowances and Reserves [Roll Forward]
Balance at Beginning of Period	$ 14,594	$ 13,292	$ 13,572
Charged to Expense	3,715	676	(205)
Decrease to Other Comprehensive Income	3,354	626	(75)
Deductions from Allowance Account	0	0	0
Balance at End of Period	$ 21,663	$ 14,594	$ 13,292