Skyward Specialty Insurance (SKWD) 10-K 28 Mar 23 2022 FY Annual report Financial data

Cover

Cover - USD ($)	12 Months Ended
	Dec. 31, 2022	Mar. 22, 2023	Jun. 30, 2022
Cover [Abstract]
Document Type	10-K
Document Annual Report	true
Document Period End Date	Dec. 31, 2022
Current Fiscal Year End Date	--12-31
Document Transition Report	false
Entity File Number	001-41591
Entity Registrant Name	SKYWARD SPECIALTY INSURANCE GROUP, INC.
Entity Incorporation, State or Country Code	DE
Entity Tax Identification Number	14-1957288
Entity Address, Address Line One	800 Gessner Road
Entity Address, Address Line Two	Suite 600
Entity Address, City or Town	Houston
Entity Address, State or Province	TX
Entity Address, Postal Zip Code	77024-4284
City Area Code	713
Local Phone Number	935-4800
Title of 12(b) Security	Common stock, par value $0.01
Trading Symbol	SKWD
Security Exchange Name	NASDAQ
Entity Well-known Seasoned Issuer	No
Entity Voluntary Filers	No
Entity Current Reporting Status	No
Entity Interactive Data Current	Yes
Entity Filer Category	Non-accelerated Filer
Entity Small Business	false
Entity Emerging Growth Company	true
Entity Ex Transition Period	false
Entity Shell Company	false
Entity Common Stock, Shares Outstanding		37,658,111
Documents Incorporated by Reference	Portions of the Registrant’s Proxy Statement relating to the 2023 annual meeting of stockholders (the “2023 Proxy Statement”), which will be filed within 120 days of December 31, 2022, are incorporated by reference into Part III of this Form 10-K.
Entity Central Index Key	0001519449
Amendment Flag	false
Document Fiscal Year Focus	2022
Document Fiscal Period Focus	FY
Entity Public Float			$ 0

Audit Information

Audit Information	12 Months Ended
	Dec. 31, 2022
Audit Information [Abstract]
Auditor Name	Ernst & Young LLP
Auditor Location	Houston, Texas
Auditor Firm ID	42

Consolidated Balance Sheets

Consolidated Balance Sheets - USD ($)	Dec. 31, 2022	Dec. 31, 2021
Investments:
Fixed maturity securities, available for sale, at fair value (amortized cost of $662,616 and $452,478, respectively)	$ 607,572,000	$ 458,351,000
Fixed maturity securities, held-to-maturity	52,467,000	47,117,000
Equity securities, at fair value	120,169,000	117,971,000
Mortgage loans	51,859,000	29,531,000
Other long-term investments	129,142,000	132,111,000
Short-term investments, at fair value	121,158,000	164,278,000
Total investments	1,082,367,000	949,359,000
Cash and cash equivalents	45,438,000	42,107,000
Restricted cash	79,573,000	65,167,000
Premiums receivable	139,215,000	112,158,000
Reinsurance recoverable, net of premium payables	581,359,000	536,327,000
Ceded unearned premium	157,645,000	137,973,000
Deferred policy acquisition costs	68,938,000	59,456,000
Deferred income taxes	36,188,000	33,663,000
Goodwill and intangible assets, net	89,870,000	91,336,000
Other assets	82,846,000	90,666,000
Total assets	2,363,439,000	2,118,212,000
Liabilities:
Reserves for losses and loss adjustment expenses	1,141,757,000	979,549,000
Unearned premiums	442,509,000	363,288,000
Deferred ceding commission	29,849,000	30,500,000
Reinsurance and premium payables	113,696,000	119,919,000
Funds held for others	36,858,000	29,587,000
Accounts payable and accrued liabilities	48,499,000	40,760,000
Notes payable	50,000,000	50,000,000
Subordinated debt, net of debt issuance costs	78,609,000	78,529,000
Total liabilities	1,941,777,000	1,692,132,000
Stockholders' equity
Series A preferred stock, $0.01 par value; 2,000,000 shares authorized, 1,969,660 and 1,970,124 shares issued and outstanding, respectively	20,000	20,000
Common stock, $0.01 par value, 168,000,000 shares authorized, 16,832,955 and 16,763,069 shares issued, respectively	168,000	168,000
Treasury stock, $0.01 par value, 233,289 and 229,449 shares, respectively	(2,000)	(2,000)
Additional paid-in capital	577,289,000	575,159,000
Stock notes receivable	(6,911,000)	(9,092,000)
Accumulated other comprehensive (loss) income	(43,485,000)	4,640,000
Accumulated deficit	(105,417,000)	(144,813,000)
Total stockholders' equity	421,662,000	426,080,000
Total liabilities and stockholders' equity	$ 2,363,439,000	$ 2,118,212,000

Consolidated Balance Sheets (Pa

Consolidated Balance Sheets (Parenthetical) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Statement of Financial Position [Abstract]
Amortized cost	$ 662,616	$ 452,478
Preferred stock, par value (in USD per share)	$ 0.01	$ 0.01
Preferred stock, shares authorized (in shares)	2,000,000	2,000,000
Preferred stock, shares issued (in shares)	1,969,660	1,970,124
Preferred stock, shares outstanding (in shares)	1,969,660	1,970,124
Common stock, par value (in USD per share)	$ 0.01	$ 0.01
Common stock, shares authorized (in shares)	168,000,000	168,000,000
Common stock, shares issued (in shares)	16,832,955	16,763,069
Treasury stock, par value (in USD per share)	$ 0.01	$ 0.01
Treasury stock (in shares)	233,289	229,449

Consolidated Statements of Oper

Consolidated Statements of Operations and Comprehensive (Loss) Income - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Revenues:
Net earned premiums	$ 615,994	$ 499,823
Commission and fee income	5,199	3,973
Net investment income	36,931	24,646
Net investment (losses) gains	(15,705)	17,107
Net realized gain on sale of business	0	5,077
Other income (loss)	1	(445)
Total revenues	642,420	550,181
Expenses:
Losses and loss adjustment expenses	402,512	354,411
Underwriting, acquisition and insurance expenses	182,171	138,498
Impairment charges	0	2,821
Interest expense	6,407	4,622
Amortization expense	1,547	1,520
Total expenses	592,637	501,872
Income before income taxes	49,783	48,309
Income tax expense	10,387	9,992
Net income attributable to participating securities	18,879	18,507
Net income attributable to common shareholders	20,517	19,810
Comprehensive (loss) income:
Net income	39,396	38,317
Unrealized gains and losses on investments:
Net change in unrealized losses on investments, net of tax	(48,545)	(8,173)
Reclassification adjustment for gains on securities no longer held, net of tax	420	597
Total other comprehensive loss	(48,125)	(7,576)
Comprehensive (loss) income	$ (8,729)	$ 30,741
Per share data:
Basic earnings per share (in dollar per share)	$ 1.24	$ 1.21
Diluted earnings per share (in dollar per share)	$ 1.21	$ 1.18
Weighted-average common shares outstanding
Basic weighted-average common shares (in shares)	16,568,393	16,308,712
Diluted weighted-average common shares (in shares)	32,653,194	32,468,048

Consolidated Statements of Stoc

Consolidated Statements of Stockholders' Equity - USD ($) $ in Thousands	Total	Preferred  Stock	Common Stock	Treasury Stock	Additional Paid-In Capital	Stock Notes Receivable	Accumulated Other Comprehensive Income	Accumulated Deficit
Stockholders' equity beginning balance at Dec. 31, 2020	$ 303,222	$ 0	$ 168	$ (4)	$ 476,482	$ (2,510)	$ 12,216	$ (183,130)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Employee equity transactions	1,309			2	427	880
Net income	38,317							38,317
Other comprehensive loss, net of tax	(7,576)						(7,576)
Reclassification of temporary equity to stockholders’ equity	90,808	20			98,250	(7,462)
Stockholders' equity ending balance at Dec. 31, 2021	426,080	20	168	(2)	575,159	(9,092)	4,640	(144,813)
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Employee equity transactions	4,311				2,130	2,181
Net income	39,396							39,396
Other comprehensive loss, net of tax	(48,125)						(48,125)
Stockholders' equity ending balance at Dec. 31, 2022	$ 421,662	$ 20	$ 168	$ (2)	$ 577,289	$ (6,911)	$ (43,485)	$ (105,417)

Consolidated Statements of Cash

Consolidated Statements of Cash Flows - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Cash flows from operating activities:
Net income	$ 39,396	$ 38,317
Adjustments to reconcile net income to net cash provided by (used in) operating activities:
Net realized losses (gains)	647	(1,856)
Depreciation and amortization expense	4,097	5,603
Stock-based compensation expense	2,287	522
Provision for bad debts	632	79
Unrealized losses on investment in Westaim	15,058	(15,251)
Earnings on illiquid investments	(16,032)	(11,413)
Deferred income tax, net	10,267	9,984
Impairment charges	0	2,821
Net realized gain on sale of business	0	(5,077)
Changes in operating assets and liabilities:
Premiums receivable, net	(27,689)	1,876
Reinsurance recoverables	(45,032)	1,062
Ceded unearned premium	(19,672)	8,548
Deferred policy acquisition costs	(9,482)	(5,975)
Losses and loss adjustment expenses	162,208	124,270
Unearned premiums	79,221	20,772
Deferred ceding commission	(651)	(5,219)
Reinsurance and premium payables	(6,223)	(4,201)
Funds held for others	7,271	2,649
Accounts payable and accrued liabilities	7,583	1,148
Other, net	5,052	6,626
Net cash provided by operating activities	208,938	175,285
Cash flows from investing activities:
Purchase of fixed maturity securities, available for sale	(268,781)	(255,155)
Purchase of illiquid investments	(4,873)	(48,060)
Purchase of equity securities	(53,548)	(60,328)
Purchase of business	0	(10,554)
Investment in direct and indirect loans	(9,767)	(16,079)
Purchase of property and equipment	(2,325)	(2,154)
Sale of other invested asset	210	0
Sale of investment in subsidiary	0	8,188
Sales and maturities of investment securities	95,641	135,289
Distributions from equity method investments	3,211	2,387
Change in short-term investments	43,120	70,207
Payable (receivable) for securities sold	529	(725)
Cash provided by (used in) deposit accounting	3,202	(6,074)
Other, net	0	44
Net cash used in investing activities	(193,381)	(183,014)
Cash flows from financing activities:
Employee share purchases	2,180	1,380
Net cash provided by financing activities	2,180	1,380
Net increase (decrease) in cash and cash equivalents and restricted cash	17,737	(6,349)
Cash and cash equivalents and restricted cash at beginning of year	107,274	113,623
Cash and cash equivalents and restricted cash at end of year	125,011	107,274
Supplemental disclosure of cash flow information:
Cash paid for interest	$ 5,761	$ 4,669

Nature of Operations

Nature of Operations	12 Months Ended
	Dec. 31, 2022
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Nature of Operations	Nature of Operations Skyward Specialty Insurance Group, Inc. (the “Company”), an insurance holding company, is a Delaware corporation that was organized in 2006. It is a specialty insurance company operating in one segment delivering commercial property and casualty products and group accident and health insurance coverages through its underwriting divisions. The Company focuses its business on markets that are underserved, dislocated and/or for which standard insurance coverages are insufficient or inadequate to meet the needs of businesses, including its customers and prospective customers operating in these markets. Its customers typically require highly specialized, customized underwriting solutions and claims capabilities. As such, the Company develops and delivers tailored insurance products and services to address each of the niche markets it serves. The Company’s portfolio of insured risks is highly diversified—it insures customers operating in a wide variety of industries; it distributes through multiple channels; it writes multiple lines of business, including general liability, excess liability, professional liability, commercial automobile liability, commercial automobile physical damage, group accident and health, property, surety and workers’ compensation. Insurance Companies The Company conducts operations principally through its four insurance companies. Houston Specialty Insurance Company (“HSIC”), its largest insurance subsidiary, underwrites multiple lines of insurance on a surplus lines basis in 50 states and the District of Columbia. Imperium Insurance Company (“IIC”), a subsidiary of HSIC, underwrites on an admitted basis in all 50 states and the District of Columbia. Great Midwest Insurance Company (“GMIC”), a subsidiary of IIC underwrites multiple lines of insurance on an admitted basis in all 50 states, the District of Columbia and is a certified surety bond company listed with U.S. Department of the Treasury. Oklahoma Specialty Insurance Company (“OSIC”), a subsidiary of GMIC, is an approved surplus lines company in 47 states. Reinsurance Company Skyward Re is a wholly owned captive reinsurance company domiciled in the Cayman Islands that was incorporated on January 7, 2020. Skyward Re assumes net reserves for certain divisions, related to a retroactive reinsurance contract, from the Company’s insurance companies and retrocedes the net reserves to a third-party reinsurer. Non-insurance Companies Skyward Underwriters Agency, Inc. (“SUA”), a subsidiary of the Company, is a managing general insurance agent and reinsurance broker for property and casualty and accident and health risks in specialty niche markets. Skyward Service Company, also the Company’s subsidiary, provides various administrative services to the Company’s subsidiaries.

Summary of Significant Accounti

Summary of Significant Accounting Policies	12 Months Ended
	Dec. 31, 2022
Accounting Policies [Abstract]
Summary of Significant Accounting Policies	Summary of Significant Accounting Policies Basis of Presentation The Company’s consolidated financial statements have been prepared in accordance with generally accepted accounting principles (“GAAP”) in the United States of America, and include accounts of the Company and its subsidiaries as of and for the years ended December 31, 2022 and 2021. All intercompany transactions and balances have been eliminated in consolidation. Use of Estimates The preparation of consolidated financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosures of contingent assets and liabilities at the date of the consolidated financial statements and the reported amounts of revenue and expenses during the reporting period. Actual results could differ materially from these estimates. Cash and Cash Equivalents Cash and cash equivalents include cash on hand and highly liquid short-term investments. Short-term investments purchased with an original maturity of three months or less are considered to be cash equivalents. The carrying value of the Company’s cash and cash equivalents approximates fair value. Restricted Cash Cash with a legal restriction as to withdrawal or use by the consolidated group is recorded as restricted cash. The carrying value of the Company’s restricted cash approximates fair value. SUA collects premiums from clients, and after deducting commissions and any applicable fees, remits these premiums to the Company’s insurance companies, noted within the Nature of Operations or to third-party insurance companies. SUA holds unremitted insurance premiums in a fiduciary capacity to third-party insurance companies, as restricted cash. The Company is required by state regulations to maintain assets on deposit with certain states and hold cash as collateral for certain reinsurance balances. Cash it holds in a depository account for others, or which is restricted by a state, is recorded as restricted cash. Investments Available for Sale Investments in fixed maturity securities are classified as available for sale and are reported at fair value based on quoted market prices or dealer quotes. Unrealized gains and losses for fixed maturity securities are excluded from net income and reported in stockholders’ equity, net of taxes, as a component of accumulated other comprehensive income (loss). If quoted market prices or dealer quotes are not available, the Company estimates fair value based on recent trading information. Premiums and discounts on mortgage-backed securities are amortized using the retroactive method adjusted for anticipated prepayments and the estimated economic life of the securities. Adjustments related to changes in prepayment assumptions are included in net investment income. Held to maturity Investments in fixed maturity securities where the Company has demonstrated the intent and ability to hold until maturity have been classified as held to maturity and are reported at amortized cost. Other-than-Temporary Impairments The Company evaluates declines in the market value of invested assets below amortized cost, for other-than-temporary impairment losses, on a quarterly basis. Impairment losses for declines in the value of its fixed maturity securities below amortized cost attributable to issuer-specific events are based on all relevant facts and circumstances for each investment and are recognized when appropriate. For all investments with unrealized losses due to market conditions or industry-related events where the Company does not have intent to sell the security and it has the ability to hold the investment for either a period of time sufficient to allow a market recovery or to maturity, declines in value below cost are not assumed to be other-than-temporary. When the Company considers the impairment of the value of an investment to be other-than-temporary, it reports the decrease in value in net income within the Consolidated Statements of Operations and a corresponding reduction in carrying value on the consolidated balance sheet. Equity securities with a readily determinable fair value Equity securities consists of common stock or preferred stock. Mutual funds, including those that invest mostly in debt securities, are classified as equity securities. Investments in equity securities with a readily determinable fair value are carried on the balance sheet at fair value using quoted market prices. Changes in the carrying value of equity securities are included in net investment (losses) gains within the Consolidated Statements of Operations. Mortgage loan s Investments in mortgage loans are classified as held for investment and carried on the balance sheet at cost adjusted for unamortized: premiums, discounts and loan fees. When an amount is determined to be uncollectible, the Company writes off the uncollectible amount in the period it was determined to be uncollectible. Interest on the loans is recognized as interest receivable which the Company includes in other assets on the consolidated balance sheet. Other long-term investments Other long-term investments include investments in equity and equity securities of non-public entities and indirect investments in loans and loan collateral. The Company has equity investments in certain limited partnerships and corporations where it has significant influence but not control. The analysis of entities that are variable interest entities indicated the Company is not the primary beneficiary, and would not have to consolidate these entities. Equity method is used to account for these investments. Under the equity method, initial investment is recorded at cost and is subsequently adjusted based on its proportionate share of distributions and net income or loss of the equity method investee. The difference between the cost of an investment and its proportionate share of the underlying equity in net assets recorded on the investee’s books is a component of investment income. The Company amortizes the difference as an adjustment to its pro-rata share of equity method income over the useful life which is based on the underlying asset. The Company does not have significant influence in its investments in equity securities of non-public entities. When these securities do not have a readily determinable fair value, the Company carries these investments at cost, minus impairment, if any, and changes resulting from observable price changes in orderly transactions for identical or similar investments of the same issuer. Investments in indirect collateralized loans and loan collateral are held through and accounted for as an ownership interest in an unconsolidated subsidiary. The Company’s ownership interests in unconsolidated subsidiaries consists of investments in entities such as partnerships, joint ventures, and special purpose investment vehicles. The Company has significant influence, but not control of these unconsolidated subsidiaries and uses the equity method to account for these investments. Short-Term Investments Short-term investments consist primarily of money market funds and are carried at cost which approximates fair value. Net Investment Income and Net Realized Gains and Losses Net investment income consists of interest, dividends and equity in earnings (losses) of investees net of investment expenses such as investment management expenses. Interest income is recognized on the accrual basis, and dividends as earned at the ex-dividend date. Interest income on mortgage-backed and asset-backed securities is recognized using the effective-yield method based on estimated principal repayments. Included in interest income is the amortization of premium and accretion of discounts on debt securities. Net realized gains and losses on investments are recognized in net income based upon the specific identification method. Reinsurance Reinsurance Accounting In the normal course of business, the Company purchases prospective reinsurance for certain lines of business on a proportional, excess of loss and facultative basis. Proportional reinsurance requires the Company to share the losses and expenses with the reinsurer in exchange for a share of the premiums. Excess of loss reinsurance shares losses, either a proportion of or in its entirety, above a certain dollar threshold, in exchange for a negotiated cost. Facultative reinsurance covers specific risks and/or policies on either a proportional or excess of loss basis. Ceded unearned premium and reinsurance balances recoverable—on paid and unpaid losses and settlement expenses—are reported separately as assets, instead of netting them with the related liabilities, since reinsurance does not relieve the Company of its legal liability to its policyholders. Reinsurance on unpaid losses and settlement expenses represent estimates of the portion of the liabilities recoverable from reinsurers. On the Consolidated Statements of Operations, net earned premium, losses and loss adjustment expenses, net and underwriting, acquisition and insurance expenses are presented net of reinsurance ceded. The Company purchases retroactive reinsurance on certain lines of business in the form of loss portfolio transfers (“LPT”) and adverse development covers. These contracts provide indemnification of losses related to past loss events where the reinsurer shares losses, either a proportion of or in its entirety, depending on certain dollar thresholds. Income generated from retroactive reinsurance contracts is deferred and amortized into net income over the settlement period and losses are charged to net income immediately. Subsequent changes in the measurement of the retroactive reinsurance contract are accounted for under a full retrospective method. Deposit Accounting Certain ceded reinsurance contracts, which management determines do not transfer significant insurance risk, are accounted for using the deposit method of accounting. The evaluation of the transfer of significant insurance risk involves an assessment of both timing risk and underwriting risk. Management may determine that a reinsurance contract does not transfer significant insurance risk if either underwriting risk or timing risk or both are not deemed to have been transferred. For those contracts that transfer only significant timing risk and do not transfer sufficient underwriting risk, a deposit asset is recorded equal to the initial cash outflow under the contract, which will then be offset by cash inflows received from the reinsurers. To the extent cash outflows are expected to differ from expected cash inflows, an accretion rate is established at inception of the contract based on actuarial estimates whereby the deposit accounting asset is increased/decreased to the estimated amount receivable over the contract term. The accretion of the deposit is based on the expected rate of return implied from the estimated cash inflows and outflows under the contract. Periodically, the Company reassesses the estimated ultimate receivable and the related expected rate of return on the deposit asset. The accretion of the deposit asset, including any changes in accretion resulting from changes in estimated cash flows, are reflected as part of investment income in the Company’s results of operations. Several reinsurance contracts require deposit accounting treatment due to not transferring sufficient underwriting risk. There were no reinsurance contracts that require deposit accounting treatment due to not transferring sufficient timing risk. Reinsurance Recoverables Reinsurance does not relieve the Company of its legal liability to its policyholders. The Company continuously monitors the financial condition of its reinsurers. As part of its monitoring efforts, the Company reviews the reinsurers’ annual financial statements. The Company also reviews insurance industry developments that may impact the financial condition of its reinsurers. The Company analyzes the credit risk associated with its reinsurance recoverables by monitoring the financial strength rating of its reinsurers from A.M. Best, a widely recognized rating agency with an exclusive insurance industry focus. It also assesses the adequacy of collateral obtained, where applicable. Should its reinsurers fail to fulfill their obligations, the Company has access to collateral from various reinsurers. The following table presents reinsurance collateral for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Reinsurance collateral $ 253,870 $ 230,908 When the Company’s review indicates the existence of uncollectible amounts from reinsurers, its policy is to charge net income and provide an allowance for estimated unrecoverable amounts. As of December 31, 2022 and 2021, it was determined that no allowance for uncollectible reinsurance recoverables was required. Reinsurance recoverables present potential exposures to individual reinsurers. The following table lists the individual reinsurers which represent 10% or more of the Company’s reinsurance recoverable balances and the respective financial strength rating from A.M. Best at December 31, 2022 and 2021: A.M. Best 2022 2021 Everest Reinsurance Co A+ 28.2 % 28.9 % Randall & Quilter (R&Q Bermuda (SAC) Ltd) Not rated Below 10 % 12.0 % Concentration of Credit Risk Other than reinsurance recoverables, financial instruments that potentially subject us to concentrations of credit risk are primarily cash and cash equivalents, restricted cash, investments and premiums receivable. Cash equivalents and short-term investments include investments in money market funds and securities backed by the U.S. government. Investments are diversified throughout many industries and geographic regions. The Company limits the amount of credit exposure with any one financial institution or issuer and believes no significant concentration of credit risk exists with respect to cash and investments. As of December 31, 2022 and 2021, outstanding premiums receivable are generally diversified due to the large number of entities comprising the Company’s customer base and their dispersion across many different lines of business and geographic regions. Failure by distribution sources to remit premiums could result in premium write-offs and a corresponding loss of income. Deferred Policy Acquisition Costs Policy acquisition costs consist of commissions and premium taxes that vary with and are directly related to the successful production of new or renewal business. The Company defers policy acquisition costs and related ceding commissions and charge or credit them to earnings in proportion with the premium earned over the life of the policy. A premium deficiency is recognized if the sum of expected losses, loss adjustment expenses, and unamortized acquisition costs exceed its related unearned premiums. The Company first recognizes a premium deficiency by charging any unamortized acquisition costs to expense to the extent required to eliminate the deficiency. If its premium deficiency is greater than unamortized acquisition costs, it accrues a liability for the excess deficiency. Anticipated investment income is considered in the determination of premium deficiencies. Management performed an analysis and determined no premium deficiency existed as of December 31, 2022 and 2021. Goodwill and Intangible Assets Goodwill and intangible assets are recorded as a result of a business combination. Goodwill represents the excess of the purchase price over the fair value of the assets acquired and liabilities assumed. The Company reviews its purchase price allocation up to one year subsequent to an acquisition and may make adjustments within the one-year period. The Company amortizes identifiable intangible assets with a finite useful life over the period that the intangible asset is expected to contribute directly or indirectly to its future cash flows; however, it does not amortize indefinite lived intangible assets. The Company evaluates goodwill and identifiable intangible assets for recoverability annually in the fourth quarter or on an interim basis should events or changes in circumstances indicate that a carrying amount may not be recoverable. To test for impairment, a qualitative assessment is performed to determine if it is more likely-than-not that the fair value of a reporting unit is less than its carrying value, including goodwill. This initial assessment includes, among other factors, consideration of: (i) past, current and projected future earnings and equity; (ii) recent trends and market conditions; and (iii) valuation metrics involving similar companies that are publicly traded and acquisitions of similar companies, if available. If the more likely-than-not threshold is met, a quantitative impairment test is performed by comparing the estimated fair value with the carrying value. If the carrying value of the net assets associated with the reporting unit exceeds the fair value of the reporting unit, goodwill is considered impaired and will be determined as the amount by which the reporting unit’s carrying value exceeds its fair value, not to exceed the carrying amount of goodwill. The Company’s reporting unit is at the underwriting division level; this is one level below the consolidated group where the underwriting division represents a business and discrete financial information is available and reviewed regularly by underwriting management. Determining the fair value of its reporting units is subjective in nature and involves the use of significant estimates and assumptions, including projected net cash flows, discount and long-term growth rates. The Company determines the fair value of its reporting units based on an income approach and market approach, whereby the fair value of the reporting unit is derived from the present value of estimated future cash flows associated with the reporting unit. The assumptions about estimated cash flows include factors such as future premiums, loss and LAE expenses, general and administrative expenses and industry trends. The Company considers historical rates and current market conditions when determining the discount and long-term growth rates to use in its analysis. The Company considers other valuation methods if the facts and circumstances indicate these methods provide a more representative approximation of fair value. Changes in these estimates based on evolving economic conditions or business strategies could result in material impairment charges in future periods. The Company bases its fair value estimates on assumptions it believes to be reasonable. Actual results may differ from those estimates. The following table presents goodwill impairment charges for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Goodwill impairment $ — $ 2,821 Goodwill impairment is included under “impairment charges” in the Consolidated Statements of Operations and Comprehensive (Loss) Income. Property and Equipment Property and equipment, which is included in other assets on the consolidated balance sheets, is recorded at cost less accumulated depreciation. Depreciation expense is recognized on a straight-line basis for financial statement purposes over periods ranging from three Leases Right-of-use (ROU) assets are included in other assets and lease liabilities are included in accounts payable and accrued liabilities on the balance sheet. For operating leases, the Company determines if a contract contains a lease at inception and recognizes the operating lease ROU assets and lease liabilities based on the present value of the future minimum lease payments at the commencement date. As the Company does not have the interest rate implicit in its leases, it uses its incremental borrowing rate based on the information available at the commencement date in determining the present value of future payments. Lease agreements may include options to extend or terminate. The options are exercised at the Company’s discretion and are included in operating lease liabilities if it is reasonably certain the option will be exercised. Lease agreements have lease and non-lease components, which are accounted for as a single lease component. Operating lease cost for future minimum lease payments is recognized on a straight-line basis over the lease term. Sublease income is recognized on a straight-line basis over the sublease term. Reserves for losses and loss adjustment expenses Reserves for losses and loss adjustment expenses (“LAE”) represent the Company’s best estimate of the ultimate net cost of all reported and unreported losses that are unpaid as of the balance sheet dates. Its estimated reserves for losses and LAE include the accumulation of estimates for claims reported and unpaid prior to the balance sheet dates, estimates (based on projections of relevant historical data) of increases in claims costs for claims already reported, of claims incurred but not reported, and estimates of expenses for investigating and adjusting all incurred and unpaid claims. The Company estimates its reserves on an undiscounted basis, using individual case-basis valuations, statistical analyses, and various actuarial methods such as: Paid Loss Development — Historical payment patterns for prior claims are used to estimate future payment patterns for claims. These patterns are applied to current payments by policy year to yield an expected ultimate loss. Incurred Loss Development — Historical case loss patterns for past claims are used to estimate future case-incurred amounts for current claims. These patterns are applied to current case losses by policy year to yield an expected ultimate loss. Case Reserve Development — Patterns of historical development in reported losses relative to historical case reserves are determined. These patterns are applied to current case reserves by policy year and the result is combined with paid losses to yield an expected ultimate loss. Expected Loss Ratio — Historical loss ratios, in combination with projections of frequency and severity trends, as well as estimates of price and exposure changes, are analyzed to produce an estimate of the expected loss ratio (“loss pick”) for each policy year. The loss pick is then applied to the earned premium for each year to estimate the expected ultimate losses. Paid and Incurred Bornhuetter/Ferguson (BF) — This approach blends the expected loss ratio method with either the paid or incurred loss development method. In effect, the BF methods produce weighted average indications for each policy year. In most cases, multiple estimation methods will be valid for the particular facts and circumstances of the claim liabilities being evaluated. Each estimation method has its own set of assumption variables and its own advantages and disadvantages, with no single estimation method being better than the others in all situations, and no one set of assumption variables being meaningful for all underwriting divisions. The relative strengths and weaknesses of the particular estimation methods, when applied to a particular group of claims, can also change over time. Therefore, the weight given to each estimation method will likely change by policy year and with each evaluation given the facts and circumstances associated with each underwriting division. The estimates generated by the methods above are based on the Company’s historical information, industry information, and its estimates of future trends in variable factors such as loss severity and loss frequency. Reserves for losses and LAE are subject to uncertainty from various sources, including changes in reporting patterns, claims settlement patterns, judicial decisions, legislation, and economic conditions. Therefore, the Company’s actual loss experience may not conform to the methods used in determining the estimated amounts for such liability at the balance sheet dates. The Company continually monitors, and reviews reserves and adjusts its estimates as necessary as new information becomes available. Reserves for losses and LAE are subject to uncertainty from various sources, including changes in reporting patterns, claims settlement patterns, judicial decisions, legislation, and economic conditions. Therefore, the Company’s actual loss experience may not conform to the assumptions used in determining the estimated amounts for such liability at the balance sheet dates. The Company continually monitors and reviews reserves, and as settlements are made or reserves adjusted, the differences are reported in the current year. Because of the nature of business the Company has historically written, management believes that it has limited exposure to environmental and other toxic tort type claim liabilities. Premiums The Company earns and recognizes property and casualty and surety premiums on a pro-rata basis over the terms of the policies. The Company earns accident and health premiums as billed, based on census data. Gross premiums written are reduced by ceded premiums from proportional, facultative and excess of loss reinsurance costs for prospective reinsurance. Its premiums receivable includes deferred premiums, which represent installment payments the Company is due from insureds under the payment terms of their policies. The following table presents recorded allowance for estimated uncollectible premiums receivable for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Allowance for doubtful accounts $ 629 $ 261 Unearned premiums represent the portion of gross premiums written which is applicable to the unexpired terms of insurance policies or reinsurance contracts in force. Ceded unearned premiums represent the portion of ceded premiums written which is applicable to the unexpired terms of insurance policies or reinsurance contracts in force. These unearned premiums are calculated on a pro-rata basis over the terms of the policies for direct and ceded amounts. Commission and Fee Income SUA commission revenue SUA commission revenue is generated from the placement of insurance policies on reinsurance programs through a reinsurance broker which represents the Company’s single performance obligation. Its transaction price is fixed at contract inception and based on a percentage of premiums placed. The Company recognizes 100% of the transaction price as the associated performance obligation is satisfied at the point in time a policy is placed as it has no constraints on revenue. SUA fee income SUA fee income is generated from the placement of insurance policies with a third-party insurance company. The Company’s single performance obligation consists of the placement of the policy. Its transaction price is variable at contract inception and based on a percentage of premium based on risk factors that vary every month such as employee census data and worker roles. The Company’s estimates its transaction price over the life of the policy using the expected value method and recognizes revenue at the point in time the policy is placed. When there are changes in the estimate of variable consideration, it recognizes those changes in the month they occur. Income Taxes Income tax expense is accrued for the tax effects of transactions reported on the consolidated financial statements, and this provision for income taxes consists of taxes currently due plus deferred taxes resulting from temporary differences between amounts reported for financial statement and income tax purposes. A valuation allowance is established for any deferred tax asset not expected to be realized. Deferred tax assets and liabilities are measured using enacted tax rates expected to apply to taxable income in the years in which temporary differences are expected to be recovered or settled. The effect on deferred tax assets and liabilities from a change in tax rates is recognized in income in the period that includes the enactment date. A liability for uncertain tax positions is recorded where it is more likely-than-not that the tax position will not be sustained upon examination by the appropriate tax authority. Changes in the liability for uncertain tax positions are reflected in income tax expense in the period when a new uncertain tax position arises, judgment changes about the likelihood of an uncertainty, the tax issue is settled, or the statute of limitation expires. Any potential net interest income or expense and penalties related to uncertain tax positions are recorded on the Consolidated Statements of Operations. The Company files a consolidated federal income tax return in the United States and certain other state tax returns. Its admitted insurance subsidiaries pay premium taxes on gross written premiums in lieu of most state income or franchise taxes. Premium tax expense is recognized within underwriting, acquisition and insurance expense on the Consolidated Statement of Operations. Fair Value of Financial Instruments Fair value is estimated for each class of financial instrument based on the framework established in the fair value accounting guidance. This guidance requires an entity to maximize the use of observable inputs and minimize the use of unobservable inputs when measuring fair value. Fair value hierarchy disclosures are based on the quality of inputs used to measure fair value. The hierarchy gives the highest priority to unadjusted quoted prices in active markets for identical assets or liabilities (Level 1 measurements) and the lowest priority to unobservable inputs (Level 3 measurements). As a part of management’s process to determine fair value, the Company utilizes widely recognized, third-party pricing sources to determine the Company’s fair values of financial instruments. The Company has obtained an understanding of the third-party pricing sources’ valuation methodologies and inputs. See Note 6 for further details regarding fair value disclosures. Stock Based Compensation The Company granted common stock to its employees and non-employee directors under the Stock Purchase Program and Equity Incentive Program (the “Legacy Programs”). The Legacy Programs required that employees who receive an award purchase a certain amount of stock, which the Company then matched. The matching share awards were subject to certain vesting requirements. For the purchased portion of the participant’s stock, the participant was required to make a minimum payment toward the purchase commitment, with the remainder of the balance issued as a note receivable to us and recorded as a stock notes receivable within Stockholders’ Equity. Compensation costs are recognized over the applicable vesting period for share-based payments to employees, former employees, and non-employee directors at fair value of the common stock on the grant date. The fair value of the common stock on the grant date was determined using an income approach and market approach. Forfeiture of purchased and awarded shares are recognized as they occur. In December 2020, the Compensation Committee of the Company’s Board of Directors (the “Compensation Committee”) approved a new Long Term Incentive Plan (the “2021 Plan”). The 2021 Plan provides for the granting of restricted stock, restricted stock units, performance share awards, as well as cash-based performance awards, to select employees and non-employee directors of the Company. Under the 2021 Plan, the Compensation Committee ratifies the selection of participants for each year’s grants which are subject to the terms and conditions of the 2021 Plan. The equity awards consist of common share awards with either a market or a performance condition and restricted common stock and common stock units. All awards are subject to a service condition and the accounting policy for each award is presented below. Market condition awards For common share awards with a market and service condition, the Company uses a probability assessment to determine the fair value of these awards on the grant date. It recognizes grant date fair value as compensation costs over the applicable service period of the award. If the market condition is not obtained, previously recognized compensation expense is not reversed. Performance and service condition awards For common share awards with a performance condition and a service condition, the Company calculates a grant date fair value based on the probability weighted assessment of the performance condition and respective award values. It recognizes compensation costs over the service period based on its latest estimate of grant date fair value. If the performance condition is not satisfied, the Company will reverse previously recognized compensati

Recent Accounting Pronouncement

Recent Accounting Pronouncements	12 Months Ended
	Dec. 31, 2022
Accounting Policies [Abstract]
Recent Accounting Pronouncements	Recent Accounting Pronouncements The Company currently qualifies as an “emerging growth company” under the Jumpstart Our Business Startups Act of 2012, or the JOBS Act. Accordingly, the Company is provided the option to adopt new or revised accounting guidance either (i) within the same periods as those otherwise applicable to non-emerging growth companies or (ii) within the same time periods as private companies. The Company may elect to adopt new or revised accounting guidance within the same time period as private companies, unless, as indicated below, management determines it is preferable to take advantage of early adoption provisions offered within the applicable guidance. Recent Accounting Standards Not Yet Adopted In June 2016, the FASB issued ASU 2016-13, Measurement of Credit Losses on Financial Instruments (Topic 326). ASU 2016-13 requires organizations to estimate credit losses on certain types of financial instruments, including receivables and available-for-sale debt securities, by introducing an approach based on expected losses. The expected loss approach will require entities to incorporate considerations of historical information, current information, and reasonable and supportable forecasts. The guidance is effective for fiscal years beginning after December 15, 2022. The Company will adopt this ASU effective January 1, 2023 using the modified retrospective app roach. The Company expects to recognize an increase in the allowance for uncollectible reinsurance of approximately $2.3 million an d an increase, net of tax, in accumulated deficit of approximately $2.3 million.

Goodwill and Intangible Assets

Goodwill and Intangible Assets	12 Months Ended
	Dec. 31, 2022
Goodwill and Intangible Assets Disclosure [Abstract]
Goodwill and Intangible Assets	Goodwill and Intangible Assets Acquisition of Aegis Surety In January 2021, the Company closed on an agreement to purchase the surety business of Aegis Surety Bonds and Insurance Services, LLC (“Aegis”) in exchange for $10.0 million in cash and the disposal of the Company’s Exterminator Pro business. The Aegis acquisition increased the Company’s scale in surety positioning the business line for profitable growth. The implied fair value of the Aegis surety underwriting business was $15.3 million and the Company recognized a gain of $3.5 million on disposal of the assets related to its Exterminator Pro underwriting business. The Company determined that the remaining goodwill of $0.9 million associated with its Exterminator Pro business was fully impaired after the disposal. The Company recorded the assets from Aegis using the acquisition method of accounting. The purchase price was allocated to the identifiable assets based on their estimated fair values on the acquisition date. The final purchase price was an $8.3 million intangible asset for agent relationships with a 15-year useful life and $6.9 million of goodwill. Compass During the second quarter of 2021, the Company elected to exit a book of errors & omissions business generated from its acquisition of Compass Group Partners, LLC (“Compass”). As a result of this decision, the Company determined the fair value of the goodwill and agent relationships was zero, resulting in an impairment of $1.9 million and $0.1 million, respectively. Sale of Boston Indemnity Company During June of 2021, the Company signed a Purchase Agreement with an unrelated third party for the sale of all the issued and outstanding capital stock of Boston Indemnity Company (BIC). The transaction was completed on October 4, 2021. The Company recorded $8.2 million in net proceeds related to the sale and recognized $1.8 million of gain on sale of business. The carrying amount and changes in the balance of goodwill by reporting unit is as follows: ($ in thousands) Accident Surety Energy Other Total Goodwill Gross balance at December 31, 2021 $ 91,577 $ 6,781 $ 10,052 $ 4,031 $ 112,441 Accumulated impairment at December 31, 2021 (44,821) — — (1,886) (46,707) Net balance at December 31, 2022 $ 46,756 $ 6,781 $ 10,052 $ 2,145 $ 65,734 ($ in thousands) Accident Surety Energy Exterminator Other Total Goodwill Gross balance at December 31, 2020 $ 91,577 $ — $ 10,052 $ 11,810 $ 4,681 $ 118,120 Accumulated impairment at December 31, 2020 (44,821) — — (9,248) — (54,069) Additions — 6,956 — — — 6,956 Disposals — (175) — (1,680) (650) (2,505) Impairment — — — (882) (1,886) (2,768) Net balance at December 31, 2021 $ 46,756 $ 6,781 $ 10,052 $ — $ 2,145 $ 65,734 The carrying amount and changes in the balance of other intangible assets are as follows: ($ in thousands) Agent Non-competes Trademarks Licenses Total Other Intangible Assets Gross balance at December 31, 2021 $ 24,558 $ 1,117 $ 999 $ 14,019 $ 40,693 Accumulated amortization at December 31, 2021 (14,421) (670) — — (15,091) Amortization (1,243) (223) — — (1,466) Net balance at December 31, 2022 $ 8,894 $ 224 $ 999 $ 14,019 $ 24,136 ($ in thousands) Agent Non-competes Trademarks Licenses Total Other Intangible Assets Gross balance at December 31, 2020 $ 16,355 $ 1,117 $ 1,122 $ 15,019 $ 33,613 Accumulated amortization at December 31, 2020 (13,203) (447) — — (13,650) Additions 8,300 — — — 8,300 Disposals (45) — (123) (1,000) (1,168) Impairment (52) — — — (52) Amortization (1,218) (223) — — (1,441) Net balance at December 31, 2021 $ 10,137 $ 447 $ 999 $ 14,019 $ 25,602 The Company’s indefinite lived intangible assets relate to insurance licenses and trademarks. Its finite lived intangible assets, which relate to policy renewals, agency relationships, within agent relationships, and non-compete/exclusivity agreements, within non-competes, have a weighted average useful life of approximately 14 years as of December 31, 2022. The Company’s recognized amortization expense for the years ended December 31, 2022 and 2021 is as follows: ($ in thousands) 2022 2021 Amortization expense $ 1,466 $ 1,441 Estimated future net amortization expense of intangible assets for the next five years is as follows: Years Ending December 31, Amount (in thousands) 2023 $ 1,466 2024 1,074 2025 998 2026 553 2027 553

Investments

Investments	12 Months Ended
	Dec. 31, 2022
Investments, Debt and Equity Securities [Abstract]
Investments	Investments The amortized cost and the fair value of the Company’s investments are summarized as follows: ($ in thousands) Gross Gross Gross Fair Value December 31, 2022 Fixed maturity securities, available for sale: U.S. government securities $ 50,416 $ 1 $ (1,876) $ 48,541 Corporate securities and miscellaneous 255,116 767 (20,754) 235,129 Municipal securities 65,836 24 (8,133) 57,727 Residential mortgage-backed securities 134,844 218 (15,206) 119,856 Commercial mortgage-backed securities 40,129 50 (3,684) 36,495 Asset-backed securities 116,275 91 (6,542) 109,824 Total fixed maturity securities, available for sale $ 662,616 $ 1,151 $ (56,195) $ 607,572 Fixed maturity securities, held to maturity: Asset-backed securities $ 52,467 $ — $ (5,696) $ 46,771 Total fixed maturity securities, held to maturity $ 52,467 $ — $ (5,696) $ 46,771 Equity securities: Common stocks $ 50,484 $ 10,015 $ (4,503) $ 55,996 Preferred stocks 11,798 15 (3,042) 8,771 Mutual funds 53,968 3,171 (1,737) 55,402 Total equity securities $ 116,250 $ 13,201 $ (9,282) $ 120,169 ($ in thousands) Gross Gross Gross Fair Value December 31, 2021 Fixed maturity securities, available for sale: U.S. government securities $ 48,816 $ 716 $ (269) $ 49,263 Corporate securities and miscellaneous 151,053 3,698 (588) 154,163 Municipal securities 53,179 3,799 (36) 56,942 Residential mortgage-backed securities 103,758 1,232 (1,255) 103,735 Commercial mortgage-backed securities 14,634 38 (188) 14,484 Asset-backed securities 81,038 226 (1,500) 79,764 Total fixed maturity securities, available for sale $ 452,478 $ 9,709 $ (3,836) $ 458,351 Fixed maturity securities, held to maturity: Asset-backed securities $ 47,117 $ — $ — $ 47,117 Total fixed maturity securities, held to maturity $ 47,117 $ — $ — $ 47,117 Equity securities: Common stocks $ 47,379 $ 13,887 $ (2,841) $ 58,425 Preferred stocks 17,821 349 (4) 18,166 Mutual funds 33,786 7,611 (17) 41,380 Total equity securities $ 98,986 $ 21,847 $ (2,862) $ 117,971 The amortized cost and estimated fair value of fixed maturity securities, available for sale, at December 31, 2022 by contractual maturity are shown below (in thousands). Expected maturities may differ from contractual maturities because borrowers have the right to call or prepay obligations with or without call or prepayment penalties. Also, changing interest rates, tax considerations or other factors may result in portfolio sales prior to maturity. ($ in thousands) Amortized Fair Value Due in less than one year $ 16,474 $ 16,215 Due after one year through five years 203,569 191,576 Due after five years through ten years 102,114 90,631 Due after ten years 49,211 42,975 Mortgage-backed securities 174,973 156,351 Asset-backed securities 116,275 109,824 Total $ 662,616 $ 607,572 The Company’s fixed maturity securities, held to maturity, at December 31, 2022 consist entirely of asset backed securities that are not due at a single maturity date. The following tables summarize gross unrealized losses and the corresponding fair values of investments, aggregated by length of time that individual securities have been in a continuous unrealized loss position: Less than 12 Months 12 Months or More Total ($ in thousands) Fair Value Gross Fair Value Gross Fair Value Gross December 31, 2022 Fixed maturity securities, available-for-sale: U.S. government securities $ 28,966 $ (603) $ 18,577 $ (1,273) $ 47,543 $ (1,876) Corporate securities and miscellaneous 171,506 (16,063) 34,283 (4,691) 205,789 (20,754) Municipal securities 51,701 (7,236) 3,689 (897) 55,390 (8,133) Residential mortgage-backed securities 56,246 (4,152) 52,778 (11,054) 109,024 (15,206) Commercial mortgage-backed securities 25,836 (1,488) 8,583 (2,196) 34,419 (3,684) Asset-backed securities 74,684 (3,351) 25,820 (3,191) 100,504 (6,542) Total fixed maturity securities, available-for-sale 408,939 (32,893) 143,730 (23,302) 552,669 (56,195) Fixed maturity securities, held-to-maturity: Asset-backed securities 46,771 (5,696) — — 46,771 (5,696) Total fixed maturity securities, held-to-maturity 46,771 (5,696) — — 46,771 (5,696) Total $ 455,710 $ (38,589) $ 143,730 $ (23,302) $ 599,440 $ (61,891) Less than 12 Months 12 Months or More Total ($ in thousands) Fair Value Gross Fair Value Gross Fair Value Gross December 31, 2021 Fixed maturity securities, available-for-sale: U.S. government securities $ 19,819 $ (267) $ 108 $ (2) $ 19,927 $ (269) Corporate securities and miscellaneous 47,308 (588) — — 47,308 (588) Municipal securities 4,549 (36) — — 4,549 (36) Residential mortgage-backed securities 72,672 (1,252) 145 (3) 72,817 (1,255) Commercial mortgage-backed securities 12,653 (175) 241 (12) 12,894 (187) Asset-backed securities 34,266 (1,463) 1,256 (38) 35,522 (1,501) Total fixed maturity securities, available-for-sale $ 191,267 $ (3,781) $ 1,750 $ (55) $ 193,017 $ (3,836) As of December 31, 2022, the Company has 111 lots of fixed maturity securities in an unrealized loss position aged over 12 months. The Company does not have the intent to sell, and it is not more likely-than-not it will be required to sell these fixed maturity securities, available for sale, before the securities recover to their amortized cost value. In addition, the Company believes none of the declines in fair values of these fixed maturity securities, available for sale relate to credit losses. The Company believes none of the declines in fair value of these fixed maturity securities, available for sale, were other-than-temporary at December 31, 2022. The Company recognized no other-than-temporary impairment adjustments on fixed maturity securities, available for sale, for the years ended December 31, 2022 and 2021. The components of net realized (losses) gains at December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Gross realized gains Fixed maturity securities, available-for sale $ 313 $ 474 Equity securities 3,865 2,763 Other 36 13 Total 4,214 3,250 Gross realized losses Fixed maturity securities, available-for sale (958) (1,160) Equity securities (3,827) (230) Other (76) (4) Total (4,861) (1,394) Net unrealized (losses) gains on securities still held Equity securities (15,058) 15,251 Net investment (losses) gains $ (15,705) $ 17,107 Proceeds from sales of debt and equity securities at December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Fixed maturity securities, available-for sale $ 13,964 $ 15,142 Equity securities 37,177 37,952 The Company’s net investment income for the years ended December 31, 2022 and 2021 is summarized as follows: ($ in thousands) 2022 2021 Income: Fixed maturity securities, available-for sale $ 18,481 $ 9,931 Fixed maturity securities, held-to-maturity 5,375 4,840 Equity securities 3,579 2,572 Equity method investments 6,015 9,280 Mortgage loans 4,767 1,188 Indirect loans 4,846 1,852 Short-term investments and cash 1,523 141 Other (102) 241 Total investment income 44,484 30,045 Investment expenses (7,553) (5,399) Net investment income $ 36,931 $ 24,646 The change in net unrealized losses on investments, net of deferred income taxes, in other comprehensive loss for the years ended December 31, 2022 and 2021 is as follows: ($ in thousands) 2022 2021 Fixed maturity securities $ (60,918) $ (9,674) Deferred income taxes 12,793 2,098 Other comprehensive loss $ (48,125) $ (7,576) Various state regulations require the Company to maintain cash, investment securities or letters of credit on deposit with the states in a depository account. At December 31, 2022 and 2021, cash and investment securities on deposit had fair values of approximately $60.2 million and $63.2 million, respectively.

Fair Value Measurements

Fair Value Measurements	12 Months Ended
	Dec. 31, 2022
Fair Value Disclosures [Abstract]
Fair ValueMeasurements	Fair Value Measurements The Company’s financial instruments include assets and liabilities carried at fair value, as well as assets and liabilities carried at cost or amortized cost but disclosed at fair value in its consolidated financial statements. In determining fair value, the market approach is generally applied, which uses prices and other relevant data based on market transactions involving identical or comparable assets and liabilities. The Company uses data—primarily provided by third-party investment managers or pricing vendors—to determine the fair value of its investments. Periodic analyses are performed on prices received from third parties to determine whether the prices are reasonable estimates of fair value. The analyses include a review of month-to-month price fluctuations and as needed, a comparison of pricing services’ valuations to other pricing services’ valuations for the identical security. The Company classifies its financial instruments into the following three-level hierarchy: Level 1 — Inputs are unadjusted, quoted prices for identical assets or liabilities in active markets at the measurement date. Level 2 — Inputs are other than quoted prices included in Level 1 that are observable for the asset or liability through corroboration with market data at the measurement date. Level 3 — Unobservable inputs that reflect management’s best estimate of what market participants would use in pricing the asset or liability at the measurement date. The following methods and assumptions were used in estimating the fair value disclosures for financial instruments in the accompanying consolidated financial statements and in these notes: U.S. government securities, mutual funds and common stock The Company uses unadjusted quoted prices for identical instruments in an active exchange to measure fair value which represent Level 1 inputs. Preferred stocks, municipal securities, corporate securities and miscellaneous The Company uses a pricing model that utilizes market-based inputs such as trades in an illiquid market for a particular security or trades in active markets for securities with similar characteristics. The model considers other inputs such as benchmark yields, issuer spreads, security terms and conditions, and other market data. These represent Level 2 fair value inputs. Commercial mortgage-backed securities, residential mortgage-backed securities and asset-backed securities The Company uses a pricing model that utilizes market-based inputs that may include dealer quotes, market spreads, and yield curves. It may evaluate individual tranches in a security by determining cash flows using the security’s terms and conditions, collateral performance, credit information benchmark yields and estimated prepayments. These represent Level 2 fair value inputs. The following table presents the carrying value and estimated fair value of the Company’s financial instruments at December 31, 2022 and 2021: 2022 2021 ($ in thousands) Carrying Fair Carrying Fair Assets Fixed maturity securities, available-for-sale $ 607,572 $ 607,572 $ 458,351 $ 458,351 Fixed maturity securities, held-to-maturity 52,467 46,771 47,117 47,117 Equity securities 120,169 120,169 117,971 117,971 Mortgage loans 51,859 52,842 29,531 29,264 Short-term investments 121,158 121,158 164,278 164,278 Cash and cash equivalents 45,438 45,438 42,107 42,107 Restricted cash 79,573 79,573 65,167 65,167 Liabilities Notes payable $ 50,000 $ 50,000 $ 50,000 $ 50,000 Subordinated debt 78,609 78,728 78,529 83,235 The following table summarizes fair value measurements by level within the fair value hierarchy for assets and liabilities with a disclosed fair value: December 31, 2022 ($ in thousands) Level 1 Level 2 Level 3 Total Assets: Fixed maturity securities, available-for-sale: U.S. government securities $ 48,541 $ — $ — $ 48,541 Corporate securities and miscellaneous — 235,129 — 235,129 Municipal securities — 57,727 — 57,727 Residential mortgage-backed securities — 119,856 — 119,856 Commercial mortgage-backed securities — 36,495 — 36,495 Asset-backed securities — 109,824 — 109,824 Total fixed maturity securities, available-for-sale 48,541 559,031 — 607,572 Fixed maturity securities, held-to-maturity: Asset-backed securities — — 46,771 46,771 Total fixed maturity securities, held-to-maturity — — 46,771 46,771 Common stocks: Consumer discretionary 1,948 — — 1,948 Consumer staples 12,036 — — 12,036 Energy 3,241 — — 3,241 Finance 22,636 — — 22,636 Industrial 9,452 — — 9,452 Information technology 2,284 — — 2,284 Materials 2,820 — — 2,820 Other 1,579 — — 1,579 Total common stocks 55,996 — — 55,996 Preferred stocks: Consumer staples — 117 — 117 Finance — 7,085 — 7,085 Industrial — 1,020 — 1,020 Other — 549 — 549 Total preferred stocks — 8,771 — 8,771 Mutual funds: Fixed income 5,068 — — 5,068 Equity 49,773 — — 49,773 Commodity 561 — — 561 Total mutual funds 55,402 — — 55,402 Total equity securities 111,398 8,771 — 120,169 Mortgage loans — — 52,842 52,842 Short-term investments 121,158 — — 121,158 Total assets measured at fair value $ 281,097 $ 567,802 $ 99,613 $ 948,512 Liabilities: Notes payable $ — $ 50,000 $ — $ 50,000 Subordinated debt — 78,728 — 78,728 December 31, 2021 ($ in thousands) Level 1 Level 2 Level 3 Total Assets: Fixed maturity securities, available-for-sale: U.S. government securities $ 49,263 $ — $ — $ 49,263 Corporate securities and miscellaneous — 154,163 — 154,163 Municipal securities — 56,942 — 56,942 Residential mortgage-backed securities — 103,735 — 103,735 Commercial mortgage-backed securities — 14,484 — 14,484 Asset-backed securities — 79,764 — 79,764 Total fixed maturity securities, available-for-sale 49,263 409,088 — 458,351 Fixed maturity securities, held-to-maturity: Asset-backed securities — — 47,117 47,117 Total fixed maturity securities, held-to-maturity — — 47,117 47,117 Common stocks: Consumer discretionary 2,102 — — 2,102 Consumer staples 13,643 — — 13,643 Energy 2,781 — — 2,781 Finance 24,657 — — 24,657 Industrial 8,806 — — 8,806 Information technology 2,408 — — 2,408 Materials 3,160 — — 3,160 Other 868 — — 868 Total common stocks 58,425 — — 58,425 Preferred stocks: Finance — 17,018 — 17,018 Other — 1,148 — 1,148 Total preferred stocks — 18,166 — 18,166 Mutual funds: Fixed income 5,374 — — 5,374 Equity 35,471 — — 35,471 Commodity 535 — — 535 Total mutual funds 41,380 — — 41,380 Total equity securities 99,805 18,166 — 117,971 Mortgage loans — — 29,264 29,264 Short-term investments 164,278 — — 164,278 Total assets measured at fair value $ 313,346 $ 427,254 $ 76,381 $ 816,981 Liabilities: Notes payable $ — $ 50,000 $ — $ 50,000 Subordinated debt — 83,235 — 83,235 The Company measures certain assets, including investments in indirect loans and loan collateral, equity method investments and other invested assets, at fair value on a nonrecurring basis only when they are deemed to be impaired. In addition to the preceding disclosures on assets and liabilities recorded at fair value in the consolidated balance sheets, the Company is also required to disclose the fair values of certain other financial instruments for which it is practicable to estimate fair value. Estimated fair value amounts, defined as the quoted market price of a financial instrument, have been determined using available market information and other appropriate valuation methodologies. However, considerable judgements are required in developing the estimates of fair value where quoted market prices are not available. Accordingly, these estimates are not necessarily indicative of the amounts that could be realized in a current market exchange. The use of different market assumptions or estimating methodologies may have an effect on the estimated fair value amounts. The following methods and assumptions were used in estimating the fair value disclosures of other financial instruments: Fixed maturity securities, held to maturity: Fixed maturity securities, held to maturity consists of senior and junior notes with target rates of return. As of December 31, 2022, the Company determined the fair value of these instruments using the income approach utilizing inputs that are unobservable (Level 3). Mortgage loans: Mortgage loans have variable interest rates and are collateralized by real property. The Company determines fair value of mortgage loans using the income approach utilizing inputs that are unobservable (Level 3). Notes payable: The carrying value approximates the estimated fair value for notes payable as the notes payable accrue interest at current market rates plus a spread. The Company determines fair value using the income approach utilizing inputs that are available (Level 2). Subordinated debt: Subordinated debt consists of two debt instruments, the Junior Subordinated Interest Debentures, due September 15, 2036, and Unsecured Subordinated Notes, due May 24, 2039. The carrying value of the Junior Subordinated Interest Debentures approximates the estimated fair value as the instrument accrues interest at current market rates plus a spread. Unsecured Subordinated Notes have a fixed interest rate. The Company determines the fair value of these instruments using the income approach utilizing inputs that are observable (Level 2). Other financial instruments qualify as insurance-related products and are specifically exempted from fair value disclosure requirements.

Mortgage Loans

Mortgage Loans	12 Months Ended
	Dec. 31, 2022
Receivables [Abstract]
Mortgage Loans	Mortgage Loans The Company has invested in Separately Managed Accounts (“SMA1” and “SMA2”), managed by Arena Investors, LP (“Arena”), which is affiliated with The Westaim Corporation (“Westaim”) who, through Westaim HIIG LP (a limited partnership controlled by Westaim), is the Company’s largest shareholder. As of December 31, 2022 and 2021, the Company held direct investments in mortgage loans from various creditors through SMA1 and SMA2. The Company’s mortgage loan portfolios are primarily senior loans on real estate across the U.S. The loans earn interest at fixed rates, mature in approximately one The carrying value of the Company’s mortgage loans for the years ended December 31, 2022 and 2021 is as follows: ($ in thousands) 2022 2021 Retail $ 16,516 $ 10,593 Commercial 15,309 6,298 Industrial 6,329 6,314 Multi-family 5,593 3,296 Office 3,197 1,691 Hospitality 4,915 1,339 $ 51,859 $ 29,531 The Company’s gross investment income for the years ended December 31, 2022 and 2021 is as follows: Years Ended December 31, ($ in thousands) 2022 2021 Retail $ 1,255 $ 66 Commercial 1,242 151 Industrial 565 90 Multi-family 909 143 Office 385 64 Land — 451 Hospitality 411 223 $ 4,767 $ 1,188 The uncollectible amounts on loans, on an individual loan basis, are determined based upon consultations and advice from the Company’s specialized investment manager and consideration of any adverse situations that could affect the borrower’s ability to repay, the estimated value of underlying collateral, and other relevant factors. When an amount is determined to be uncollectible, the Company writes off the uncollectible amount in the period it was determined to be uncollectible. The were no write-offs for uncollectible amount for the years ended December 31, 2022 and 2021. As of December 31, 2022 and 2021, approximately $6.4 million and $10.8 million of mortgage loans, respectively, were in the process of foreclosure. The carrying value of the mortgage loans in foreclosure is the lower of cost adjusted for unamortized premiums, discounts, and loan fees or the fair value of the collateral less costs to sell.

Other Long-Term investments

Other Long-Term investments	12 Months Ended
	Dec. 31, 2022
Equity Method Investments and Joint Ventures [Abstract]
Other Long-Term Investments	Other Long-Term Investments Equity Method Investments The Company’s ownership interests in most of its equity method investments range from approximately 3% to less than 50% where the Company has significant influence but not control. The Company owns 100% of the limited partner interests in Universa Black Swan Protection Protocol LIX L.P. (“Universa Black Swan”); however, it does not have the power to direct the activities of Universa Black Swan and the Company does not consolidate the entity. The Company owns investment products issued by Arena Special Opportunities Partners (Feeder) I, LP (“Arena SOP”), managed by Arena, which is affiliated with Westaim. The investment products include senior and junior notes issued by the Arena SOP to raise capital from limited partners to fund purchases of investments. The return on the investments is used to pay interest on the senior and junior notes based on target returns of each class. The senior and junior notes are debt securities classified as held to maturity and presented on the balance sheet within fixed maturity securities, held to maturity. Income in excess of return targets on the senior and junior notes is allocated to the investment in Arena SOP. During the year ended December 31, 2021, the Company invested $1.9 million in Hudson Ventures Fund 2, LP., $5.0 million in Universa Black Swan, and $12.0 million in JVM Multi-Family Premier Fund IV, LLC and $12.0 million in JVM Preferred Equity Fund, LLC, together “JVM Funds LLC”. During the year ended December 31, 2022, the Company entered into an agreement for limited partnership interests in Brewer Lane Ventures Fund II, L.P. During the year ended December 31, 2022, the Company invested $0.2 million in Brewer Lane Ventures Fund II, L.P. and $1.3 million in Hudson Ventures Fund 2, LP. The carrying value of equity method investments at December 31, 2022 and 2021 is as follows: ($ in thousands) 2022 2021 Arena SOP LP units $ 8,734 $ 5,692 Arena Special Opportunities Fund, LP units 44,504 41,763 Brewer Lane Ventures Fund II LP units 200 — Dowling Capital Partners LP units 1,965 2,416 Hudson Ventures Fund 2 LP units 3,551 1,913 JVM Funds LLC units 22,473 24,000 RISCOM 4,037 3,366 Universa Black Swan LP units 1,325 4,354 $ 86,789 $ 83,504 Net investment income from equity method investments at December 31, 2022 and 2021 is summarized as follows: ($ in thousands) 2022 2021 Arena SOP LP units $ 3,042 $ 4,717 Arena Special Opportunities Fund, LP units 3,719 3,729 Dowling Capital Partners LP units 502 438 Hudson Ventures Fund 2 LP units 379 (16) JVM Funds LLC (70) — RISCOM 1,471 1,058 Universa Black Swan LP units (3,028) (646) $ 6,015 $ 9,280 The unfunded commitment of equity method investments at December 31, 2022 and 2021 is as follows: ($ in thousands) 2022 2021 Brewer Lane Ventures Fund II LP units $ 4,800 $ — Dowling Capital Partners LP units 386 368 Hudson Ventures Fund 2 LP units 1,796 3,063 $ 6,982 $ 3,431 The difference between the cost of an investment and its proportionate share of the underlying equity in net assets is allocated to the various assets and liabilities of the equity method investment. The Company amortizes the difference in net assets over the same useful life of a similar asset as the underlying equity method investment. For investment in RISCOM, a similar asset would be agent relationships. The Company amortizes this difference over a 15-year useful life. The following table summarizes the Company’s recorded investment in RISCOM compared to its share of underlying equity for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Investment in RISCOM: Underlying equity $ 2,292 $ 1,378 Difference 1,745 1,988 Recorded investment balance $ 4,037 $ 3,366 The $24.0 million investment in JVM Funds LLC as of December 31, 2021 represented the provisional amount, which reflected an estimate of no difference in the proportionate share of underlying equity in net assets. During the year ended December 31, 2022, the Company adjusted its purchase price allocation and allocated the difference between the cost of JVM Funds LLC and its proportionate share of the underlying equity in net assets to investments in rental properties. The Company amortizes the difference in net assets over the 7-year estimated useful life of the investment in rental properties. The following table summarizes the Company’s recorded investment in JVM Funds LLC compared to its share of underlying equity for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Investment in JVM Funds LLC: Underlying equity $ 21,565 $ 24,000 Difference 908 — Recorded investment balance $ 22,473 $ 24,000 Investment in Bank Holding Companies Beginning 2017 and through 2018, the Company acquired a $2.0 million investment in Captex Bancshares, a Texas bank holding company. The Company’s assessment of its ownership percentage and influence through one of its employees on the Board of Directors of Captex Bankshares indicates the Company does not have significant influence over the investee. The Company carries its investment in Captex Bancshares at cost, less impairment or observable changes in price. The Company reviews these investments for impairment or observable changes in price during each reporting period. There were no impairments or observable changes in price during the years ended December 31, 2022 and 2021. During the first quarter of 2020, the Company acquired a $2.0 million investment in Gulf Capital Bank, a Texas bank holding company. The Company’s assessment of its ownership percentage indicates it does not have significant influence over the investee. During the fourth quarter of 2020, the Company sold approximately $1.8 million of shares to other owners of Gulf Capital Bank at cost. The Company sold its remaining shares of $0.2 million in Gulf Capital Bank at cost during the year ended December 31, 2022. The Company carried its investment in Gulf Capital Bank at cost, less impairment or observable changes in price. Investment in Indirect Loans and Loan Collateral As of December 31, 2022 and 2021, the Company held indirect investments in collateralized loans and loan collateral through SMA1 and SMA2. The carrying value and unfunded commitment of the SMA1 and SMA2 for the years ended December 31, 2022 and 2021 are as follows: 2022 2021 ($ in thousands) Carrying Unfunded Carrying Unfunded SMA1 $ 36,426 $ — $ 33,100 $ — SMA2 2,010 — 10,855 16,563 Investment in indirect loans and loan collateral $ 38,436 $ — $ 43,955 $ 16,563 See Note 11 for common stock acquired from an entity providing the Company’s subordinated debt.

Property and Equipment

Property and Equipment	12 Months Ended
	Dec. 31, 2022
Property, Plant and Equipment [Abstract]
Property and Equipment	Property and Equipment The following table presents the components of property and equipment for the years ended December 31, 2022 and 2021, which are included within other assets on the consolidated balance sheets. ($ in thousands) 2022 2021 Leasehold improvements $ 2,670 $ 2,761 Equipment 7,230 7,477 Software 25,964 23,314 Other 39 39 35,903 33,591 Accumulated depreciation (27,229) (23,964) Total $ 8,674 $ 9,627 The following table presents recorded depreciation expense at December 31, 2022 and 2021: ($ in thousands) 2022 2021 Depreciation expense $ 3,582 $ 3,636

Leases

Leases	12 Months Ended
	Dec. 31, 2022
Leases [Abstract]
Leases	Leases The Company determines if a contract contains a lease at inception and recognizes a right-of-use asset, within other assets, and lease liability, within accounts payable and accrued liabilities, based on the present value of future lease payments. In cases where its leases do not provide an implicit interest rate, the Company uses its incremental borrowing rate based on the information available on the inception date to determine the lease liability. The Company’s leases are primarily for office facilities which have been classified as operating leases. Its leases have remaining lease terms ranging from one year to 7 years, some of which include options to extend the leases. Lease expense for the years ended December 31, 2022 and 2021 was $2.6 million and $2.7 million, respectively. The following tables provide information regarding the Company’s leases for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Operating lease right-of-use assets $ 8,214 $ 10,532 Operating lease liabilities 8,616 10,921 Operating lease weighted-average remaining lease term 5.00 years 5.73 years Operating lease weighted-average discount rate 3.16 % 3.12 % ($ in thousands) 2022 2021 Operating lease expense $ 2,414 $ 2,607 Short-term lease expense 220 127 Total lease expense $ 2,634 $ 2,734 Operating cash outflows from operating leases $ 2,382 $ 2,361 The following table sets forth the future minimum lease payment obligations of the Company’s operating leases at December 31, 2022: ($ in thousands) 2022 2023 $ 2,206 2024 1,996 2025 1,465 2026 1,227 2027 1,116 Thereafter 1,189 Total future minimum operating lease payments $ 9,199 Less imputed interest (583) Total operating lease liability $ 8,616

Subordinated Debt

Subordinated Debt	12 Months Ended
	Dec. 31, 2022
Debt Disclosure [Abstract]
Subordinated Debt	Subordinated Debt The following table summarizes the Company’s subordinated debt for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Junior subordinated interest debentures, due September 15, 2036, payable quarterly Principal $ 59,794 $ 59,794 Less: Debt issuance costs (657) (705) Unsecured subordinated notes, due May 24, 2039, interest payable quarterly Principal 20,000 20,000 Less: Debt issuance costs (528) (560) Subordinated debt, net of debt issuance costs $ 78,609 $ 78,529 In May 2019, the Company entered into an agreement to issue unsecured subordinated notes (the “Notes”) with an aggregate principal amount of $20.0 million. Interest on the Notes is fixed at 7.25% for the first 8 years and fixed at 8.25% thereafter. Early retirement of the debt ahead of 8 year commitment requires all interest payments to be paid in full as well as the return of outstanding principal. Principal is due at maturity on May 24, 2039 and interest is payable quarterly. The Notes have junior priority to all previously issued debt. The Company reports debt related to the Notes in its December 31, 2022 and 2021 consolidated balance sheets, net of debt issuance costs of approximately $0.5 million and $0.6 million, respectively. These deferred financing costs are presented as a direct deduction from the carrying amount of the subordinated debt. On August 2, 2006, Delos Capital Trust n/k/a HIIG Capital Trust I (the “Trust”), a Delaware statutory trust, issued $58.0 million of fixed/floating rate capital securities guaranteed by us. The Trust also issued us $1.8 million of common stock, classified within other long-term investments. The Company has not consolidated the Trust that issued the capital securities, as it does not meet the criteria for consolidation and the Company does not have significant influence over the investee. The Company carries its investment in the common stock of the Trust at cost. There were no impairments or observable changes in price during the year ended December 31, 2022. The sole asset of the Trust consists of Fixed/Floating Rate Junior Subordinated Deferrable Interest Debentures (the “Debentures”) with a principal amount of $59.8 million issued by the Company. The Debentures are an unsecured obligation that are currently redeemable, and have a maturity date of September 15, 2036. Interest on the Debentures is payable quarterly at an annual rate based on the three-month LIBOR (4.77% at December 31, 2022) plus 3.4%. The Company reflects debt related to the Debentures in its December 31, 2022 and 2021 consolidated balance sheets, net of debt issuance costs of approximately $0.7 million and $0.7 million, respectively. These deferred financing costs are presented as a direct deduction from the carrying amount of the subordinated debt. The following table summarizes the Company’s notes payable for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Term loan, due December 31, 2024, interest payable quarterly $ 50,000 $ 50,000 The interest rate on the $50.0 million term loan is the lesser of the one-month LIBOR (4.39% on December 31, 2022) plus the Applicable Margin, which is defined as 1.65%, or the highest lawful rate. Interest-only payments are due and payable on a quarterly basis through December 31, 2024. The principal balance of the $50.0 million term loan is due December 31, 2024. Interest payments on the term loan at December 31, 2022 and 2021 were as follows: ($ in thousands) 2022 2021 Interest payments on term loan $ 1,443 $ 894 The interest rate on the $50.0 million revolving line of credit is the lesser of the prime rate, as published by the Wall Street Journal, or the one-month LIBOR (4.39% on December 31, 2022) plus the Applicable Margin, which is defined as the lesser of 1.65%, or the highest lawful rate. The revolving promissory note includes a fee of 0.25% on the unused portion. Interest-only payments are due and payable on a quarterly basis through December 31, 2024. The entire principal balance of the $50.0 million revolving line of credit is due December 31, 2024. Subject to lender approval, the Company has a right to increase the capacity to $75.0 million. Interest payments on the Company’s revolving line of credit at December 31, 2022 and 2021 were as follows: ($ in thousands) 2022 2021 Interest payments on revolving line of credit $ — $ 127 The indebtedness is collateralized by a perfected first priority security interest in all of the assets of the Company, SUA and the outstanding capital stock of HSIC, which are both subsidiaries of the Company. The Company’s credit agreement includes financial covenants that require the Company maintain minimum surplus and risk-based capital on HSIC, minimum net worth, and a minimum fixed charge coverage ratio as well as other customary covenants and events of default. As of December 31, 2022, the Company was in compliance with all covenants in its credit agreement.

Notes_Payable

Notes Payable	12 Months Ended
	Dec. 31, 2022
Debt Disclosure [Abstract]
Notes Payable	Subordinated Debt The following table summarizes the Company’s subordinated debt for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Junior subordinated interest debentures, due September 15, 2036, payable quarterly Principal $ 59,794 $ 59,794 Less: Debt issuance costs (657) (705) Unsecured subordinated notes, due May 24, 2039, interest payable quarterly Principal 20,000 20,000 Less: Debt issuance costs (528) (560) Subordinated debt, net of debt issuance costs $ 78,609 $ 78,529 In May 2019, the Company entered into an agreement to issue unsecured subordinated notes (the “Notes”) with an aggregate principal amount of $20.0 million. Interest on the Notes is fixed at 7.25% for the first 8 years and fixed at 8.25% thereafter. Early retirement of the debt ahead of 8 year commitment requires all interest payments to be paid in full as well as the return of outstanding principal. Principal is due at maturity on May 24, 2039 and interest is payable quarterly. The Notes have junior priority to all previously issued debt. The Company reports debt related to the Notes in its December 31, 2022 and 2021 consolidated balance sheets, net of debt issuance costs of approximately $0.5 million and $0.6 million, respectively. These deferred financing costs are presented as a direct deduction from the carrying amount of the subordinated debt. On August 2, 2006, Delos Capital Trust n/k/a HIIG Capital Trust I (the “Trust”), a Delaware statutory trust, issued $58.0 million of fixed/floating rate capital securities guaranteed by us. The Trust also issued us $1.8 million of common stock, classified within other long-term investments. The Company has not consolidated the Trust that issued the capital securities, as it does not meet the criteria for consolidation and the Company does not have significant influence over the investee. The Company carries its investment in the common stock of the Trust at cost. There were no impairments or observable changes in price during the year ended December 31, 2022. The sole asset of the Trust consists of Fixed/Floating Rate Junior Subordinated Deferrable Interest Debentures (the “Debentures”) with a principal amount of $59.8 million issued by the Company. The Debentures are an unsecured obligation that are currently redeemable, and have a maturity date of September 15, 2036. Interest on the Debentures is payable quarterly at an annual rate based on the three-month LIBOR (4.77% at December 31, 2022) plus 3.4%. The Company reflects debt related to the Debentures in its December 31, 2022 and 2021 consolidated balance sheets, net of debt issuance costs of approximately $0.7 million and $0.7 million, respectively. These deferred financing costs are presented as a direct deduction from the carrying amount of the subordinated debt. The following table summarizes the Company’s notes payable for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Term loan, due December 31, 2024, interest payable quarterly $ 50,000 $ 50,000 The interest rate on the $50.0 million term loan is the lesser of the one-month LIBOR (4.39% on December 31, 2022) plus the Applicable Margin, which is defined as 1.65%, or the highest lawful rate. Interest-only payments are due and payable on a quarterly basis through December 31, 2024. The principal balance of the $50.0 million term loan is due December 31, 2024. Interest payments on the term loan at December 31, 2022 and 2021 were as follows: ($ in thousands) 2022 2021 Interest payments on term loan $ 1,443 $ 894 The interest rate on the $50.0 million revolving line of credit is the lesser of the prime rate, as published by the Wall Street Journal, or the one-month LIBOR (4.39% on December 31, 2022) plus the Applicable Margin, which is defined as the lesser of 1.65%, or the highest lawful rate. The revolving promissory note includes a fee of 0.25% on the unused portion. Interest-only payments are due and payable on a quarterly basis through December 31, 2024. The entire principal balance of the $50.0 million revolving line of credit is due December 31, 2024. Subject to lender approval, the Company has a right to increase the capacity to $75.0 million. Interest payments on the Company’s revolving line of credit at December 31, 2022 and 2021 were as follows: ($ in thousands) 2022 2021 Interest payments on revolving line of credit $ — $ 127 The indebtedness is collateralized by a perfected first priority security interest in all of the assets of the Company, SUA and the outstanding capital stock of HSIC, which are both subsidiaries of the Company. The Company’s credit agreement includes financial covenants that require the Company maintain minimum surplus and risk-based capital on HSIC, minimum net worth, and a minimum fixed charge coverage ratio as well as other customary covenants and events of default. As of December 31, 2022, the Company was in compliance with all covenants in its credit agreement.

Stockholders_ Equity

Stockholders’ Equity	12 Months Ended
	Dec. 31, 2022
Equity [Abstract]
Stockholders’ Equity	Stockholders’ Equity Conversion feature On April 24, 2020 the Company closed a private preferred share rights offering. Existing holders of common stock were given the right to subscribe for shares, on a pro rata basis, of Series A Convertible Preferred Stock (the “Preferred Shares”) with a face value of $50.00 per share. The Preferred Shares provide the holder the option at any time to convert the Preferred Shares into common stock based on the Option Conversion Rate. The initial Option Conversion rate allowed the holder of the Preferred Shares the right to convert into common stock based on a conversion price equal to $6.96 per common share. In accordance with the terms of the Preferred Shares, the Option Conversion Rate was adjusted upon the completion of the audit of the financial statements as of and for the year ended December 31, 2021. The adjustments to the Option Conversion Rate consisted of adjustments for: (i) the after-tax cost of the loss portfolio transfer, a retroactive reinsurance agreement the Company entered into during the second quarter of 2020 (“LPT”); (ii) the after-tax impact of any co-participation expense related to the LPT; (iii) the development of losses and LAE reserves subject to but in excess of limits on the LPT; and (iv) the after-tax impact of development on losses and LAE reserves not subject to the LPT subsequent to December 31, 2019. As of December 31, 2022 and 2021, the Option Conversion Rate allowed the holder of the Preferred Shares the right to convert into common stock based on a conversion price equal to $6.04 per common share. As of December 31, 2022 and 2021, the Company has the ability to settle in common shares and the Preferred Shares were classified within Stockholders’ Equity. The following table presents Preferred Shares that could be converted to common shares after the final adjustment to the Option Conversion Rate at December 31, 2022: 2022 Preferred shares outstanding 1,969,660 Common shares upon conversion of preferred shares 16,305,113 The Preferred Shares are subject to mandatory conversion upon a defined change of control transaction or the closing of an initial public offering at the Mandatory Conversion Rate. The Mandatory Conversion Rate is similar to the Option Conversion Rate but is adjusted for the after-tax impact of any co-participation expense related to the LPT, the development of losses and LAE reserves in excess of limits on the LPT and the after-tax impact of development on losses and LAE reserves not subject to the LPT on the final day of the last quarter-end prior to when a defined change of control transaction or closing of an initial public offering occurs. As of December 31, 2022 and 2021, the Mandatory Conversion Rate allowed the holder of the Preferred Shares the right to convert into common stock based on a conversion price equal to $6.04 per common share. Preference The Preferred Shares have preference in liquidation over common stock in the amount of the face value of $50.00 per share and any declared but unpaid dividends to related common shares at the applicable conversion rate.

Income Taxes

Income Taxes	12 Months Ended
	Dec. 31, 2022
Income Tax Disclosure [Abstract]
Income Taxes	Income Taxes Income tax (benefit) expense for the years ended December 31, 2022 and 2021 consisted of the following: ($ in thousands) 2022 2021 Current income tax expense $ 120 $ — Deferred tax expense related to temporary differences 10,267 9,992 Total income tax expense $ 10,387 $ 9,992 The Company’s provision for income taxes generally does not deviate substantially from the statutory tax rate. The effective tax rate may vary slightly from the statutory rate due to tax adjustments for tax-exempt income and dividends-received deduction. The differences between income taxes expected at the federal statutory income tax rate of 21% and the reported income tax expense for the years ended December 31, 2022 and 2021 are summarized as follows: 2022 2021 ($ in thousands) Amount Percentage Amount Percentage Income tax expense at federal statutory rate $ 10,454 21.0 % $ 10,145 21.0 % Tax advantaged investments (324) (0.7) (256) (0.5) Other 257 0.6 103 0.2 Total income tax expense $ 10,387 20.9 % $ 9,992 20.7 % The tax effects of temporary differences that give rise to significant portions of the deferred tax assets and deferred tax liabilities at both December 31, 2022 and 2021 are presented below: ($ in thousands) 2022 2021 Deferred tax assets: Net operating losses $ 14,966 $ 28,009 Losses and loss adjustment expenses 10,748 7,782 Unearned premiums 11,959 9,461 Intangibles 607 1,632 Capital loss carryover 1,321 — Unrealized losses on investments 11,563 — Stock options/awards 1,107 627 Other 3,369 1,034 Total deferred tax assets 55,640 48,545 Less valuation allowance (586) (586) Total deferred tax assets after valuation allowance 55,054 47,959 Deferred tax liabilities: Deferred policy acquisition costs 8,209 6,063 Depreciation 1,481 1,459 Investments 7,144 5,507 Unrealized gains on investments — 1,230 Other 2,032 37 Total deferred tax liabilities 18,866 14,296 Deferred income taxes $ 36,188 $ 33,663 The Company made no payment for federal income taxes, during the years ended December 31, 2022 and 2021, which are available for recoupment in the event of future losses. The Company’s federal income tax returns for tax years 2019 to 2021 are subject to examination by the Internal Revenue Service. As of December 31, 2022 and 2021, management does not believe there are any uncertain tax benefits that could be recognized within the next 12 months that would impact the Company’s effective tax rate. The Company classifies all interest and penalties related to tax contingencies as income tax expense. As of December 31, 2022 and 2021, there was no accrued interest recorded as an income tax liability. The Company has federal net operating loss carryforwards of approximately $71.3 million. These net operating losses are set to expire beginning in 2030. The Company is limited on the utilization of $58.6 million of the net operating losses under Internal Revenue Code Section 382 which imposes limitations on a corporation’s ability to utilize tax attributes if the corporation experiences an “ownership change.” The Company experienced an ownership change during 2013. The 382 limitation is expected to result in an expiration of $2.8 million ($0.6 million tax effected) of net operating losses. A valuation allowance has been established against this balance that is expected to expire without utilization. The Company also generated a capital loss carryforward during the year ended December 31, 2022, resulting in a deferred tax asset of approximately $1.3 million. This carryforward will expire in 2027 as the Company expects to utilize this carryforward, no valuation allowance is recorded against this deferred tax asset. The Company provides a valuation allowance against deferred tax assets when it is more likely-than-not that some portion, or all, of deferred tax assets will not be realized. Its deferred tax valuation allowance for the years ended December 31, 2022 and 2021 is as follows: ($ in thousands) 2022 2021 Balance at beginning of year $ 586 $ 586 Balance at end of year $ 586 $ 586

Reserves for Losses and Loss Ad

Reserves for Losses and Loss Adjustment Expenses	12 Months Ended
	Dec. 31, 2022
Insurance [Abstract]
Reserves for Losses and Loss Adjustment Expenses	Reserves for Losses and Loss Adjustment Expenses The Company presents its loss development on a consolidated basis; however, it evaluates net ultimate loss and LAE under three sub-categories: multiline solutions, short tail/monoline specialty lines and exited lines. The Company has chosen to disaggregate its short-duration loss disclosures in this manner as to not obscure useful information by otherwise aggregating items with significantly different characteristics. A description of the factors the Company considered in its disaggregation by sub-category is as follows: Short tail/monoline specialty lines Short tail/monoline specialty lines includes those market niches for which the Company serves with monoline solutions which generally have shorter durations for losses to fully develop. Losses for these lines are generally reported within a short period of time from the date of loss, and in most instances, claims are settled and paid within a relatively short timeframe. Short tail/monoline specialty can be impacted by larger losses which can be more complex due to factors such as difficulty determining actual damages, legal and regulatory impediments potentially extending the period of time it takes to settle and pay claims. Multi-line Solutions Multi-line solutions includes those market niches for which the Company provides multiple products most frequently as an integrated solution. The multi-line solution subcategory is made up predominantly of occurrence liability including general liability, excess liability, and commercial auto. Multi-line solutions have a longer duration for losses to fully develop compared to short-tail/monoline specialty lines. Due to the unique claim characteristics of each product and the longer-tail nature of the multi-line solutions, this introduces more uncertainty as over time the claims can be impacted by changes in regulation, inflation and other unforeseen factors. Exited lines Exited lines includes all underwriting divisions which the Company has placed in run-off and are presented separately from lines that it currently underwrites. The reconciliation of unpaid losses and loss adjustment expenses as reported in the consolidated balance sheets for the years ended December 31, 2022 and 2021 is as follows: ($ in thousands) 2022 2021 Reserves for losses and LAE, beginning of period $ 979,549 $ 856,780 Less: reinsurance recoverable on unpaid claims, beginning of period (381,338) (375,178) Reserves for losses and LAE, beginning of period, net of reinsurance 598,211 481,602 Incurred, net of reinsurance, related to: Current period 393,939 338,348 Prior years 14,385 28,000 Total incurred, net of reinsurance 408,324 366,348 Paid, net of reinsurance, related to: Current period 105,928 77,551 Prior years 194,836 172,188 Total paid 300,764 249,739 Net reserves for losses and LAE, end of period 705,771 598,211 Plus: reinsurance recoverable on unpaid claims, end of period 435,986 381,338 Reserves for losses and LAE, end of period $ 1,141,757 $ 979,549 During the year ended December 31, 2022, the Company’s net incurred losses for accident years 2021 and prior developed adversely by $14.4 million which was related to losses subject to the LPT. Within exited lines, adverse development of $14.5 million was from the 2019 accident year primarily driven by increased frequency and severity in general and professional liability. The remaining $8.4 million of net adverse development was from various other accident years. Within multi-line solutions, favorable development of $10.8 million was from the 2020 through 2021 accident years and was primarily driven by a reduction in frequency of claims in commercial auto and general liability. The remaining $2.3 million of net adverse development was from various other accident years. There was no net development in short tail/monoline specialty lines. During the year ended December 31, 2021, the Company’s net incurred losses and LAE for accident years 2020 and prior developed adversely by $28.0 million driven by $28.8 million of adverse development in exited lines and $4.8 million of adverse development in multi-line solutions, partially offset by $5.6 million of favorable development in short tail lines. Within exited lines, the $28.8 million of adverse development was primarily related to the 2013, 2015, and 2018 accident years and was predominantly driven by increases in both frequency and severity of losses in general liability. Within multi-line solutions, adverse development of $4.8 million was primarily related to the 2016 and 2017 accident years and was driven by increased frequency and severity of claims in commercial auto. Partially offsetting the adverse development was favorable development of $5.6 million within short tail lines, primarily related to the 2019 and 2020 accident years, driven by favorable loss emergence relative to actuarial expectations in property and accident & health. Short Duration Contract Disclosures Losses and LAE reserves represent the Company’s best estimate of the ultimate net cost of all reported and unreported losses that are unpaid as of the balance sheet dates. The Company’s estimated reserves for losses and LAE include the accumulation of estimates for claims reported and unpaid prior to the balance sheet dates, estimates (based on projections of relevant historical data) of increases in claims costs for claims already reported, of claims incurred but not reported, and estimates of expenses for investigating and adjusting all incurred and unpaid claims. In determining the cumulative number of reported claims, the Company measures claim counts by incident. The claim counts include all claims reported, even if the Company does not establish a liability for the claim (i.e. reserve for loss and loss adjustment expenses). Short Tail/Monoline Specialty — includes specialty/monoline business — Global Property, A&H, Surety, Professional Lines underwriting divisions Incurred Losses and ALAE, Net of Reinsurance ($ in thousands) As of December 31, 2022 Years Ended December 31, Reported Claims Accident Year 2018* 2019* 2020* 2021* 2022 IBNR 2018 $ 33,570 $ 33,570 $ 33,570 $ 36,863 $ 34,363 $ 559 858 2019 62,922 48,101 45,301 48,800 230 1,015 2020 66,359 64,859 64,859 6,614 1,258 2021 100,172 100,172 25,018 1,428 2022 123,342 80,974 1,282 Total $ 371,536 Cumulative net paid loss and LAE from the table below (218,145) Net reserves for loss and LAE before 2018 5,512 Total net reserves for loss and LAE $ 158,903 *Data presented for these calendar years is required supplementary information, which is unaudited. Cumulative Paid Losses and ALAE, Net of Reinsurance ($ in thousands) Years Ended December 31, Accident Year 2018* 2019* 2020* 2021* 2022 2018 $ 24,754 $ 31,907 $ 31,323 $ 33,522 $ 33,446 2019 33,714 40,228 41,484 45,031 2020 30,974 56,499 70,684 2021 14,754 49,526 2022 19,458 Total $ 218,145 *Data presented for these calendar years is required supplementary information, which is unaudited. Multi-line Solutions — mid to longer tail lines of business, includes the Company’s industry solutions, programs, captives and transactional E&S underwriting divisions Incurred Losses and ALAE, Net of Reinsurance ($ in thousands) As of December 31, 2022 Accident Years Ended December 31, Reported Claims 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 IBNR 2013 $ 66,517 $ 71,800 $ 64,439 $ 73,382 $ 75,196 $ 74,701 $ 74,987 $ 75,419 $ 69,496 $ 69,515 $ 1,994 3,324 2014 100,355 100,355 115,749 116,970 116,970 117,783 118,995 120,697 120,777 946 4,977 2015 103,191 114,266 117,024 117,024 119,216 121,746 122,839 122,902 2,446 5,364 2016 63,223 62,843 62,843 62,643 69,701 73,200 73,318 1,523 4,691 2017 65,332 65,332 64,260 72,913 78,578 78,762 4,331 5,515 2018 74,476 74,476 73,868 73,868 74,209 10,202 5,041 2019 107,432 106,432 106,432 110,896 1,487 6,021 2020 140,880 140,880 134,124 27,390 5,393 2021 173,568 169,566 60,497 6,486 2022 223,447 105,571 7,330 Total $ 1,177,516 Cumulative net paid loss and LAE from the table below (821,766) Net reserves for loss and LAE before 2013 4,945 Total net reserves for loss and LAE $ 360,695 *Data presented for these calendar years is required supplementary information, which is unaudited. Cumulative Paid Losses and ALAE, Net of Reinsurance ($ in thousands) Years Ended December 31, Accident 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 2013 $ 19,912 $ 40,425 $ 48,673 $ 59,460 $ 67,857 $ 73,511 $ 75,117 $ 75,340 $ 75,030 $ 74,178 2014 32,530 63,699 81,251 96,639 101,984 104,984 105,756 106,214 104,076 2015 44,152 72,137 88,833 99,401 108,291 114,098 117,295 118,166 2016 23,239 42,528 53,352 58,895 60,864 63,893 71,565 2017 23,770 41,945 53,093 64,235 67,243 69,096 2018 26,201 42,568 50,320 64,119 70,080 2019 33,019 59,529 78,803 96,601 2020 33,538 67,216 83,533 2021 39,388 78,923 2022 55,548 Total $ 821,766 *Data presented for these calendar years is required supplementary information, which is unaudited. Exited Lines — all lines in runoff Incurred Losses and ALAE, Net of Reinsurance ($ in thousands) As of December 31, 2022 Years Ended December 31, Reported Claims Accident 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 IBNR 2013 $ 44,791 $ 37,993 $ 44,909 $ 46,437 $ 48,372 $ 48,372 $ 49,850 $ 49,486 $ 53,236 $ 54,130 $ 2,031 2,640 2014 64,186 57,904 62,425 63,729 63,729 68,855 69,920 71,219 71,761 11,475 4,149 2015 61,810 65,063 68,008 70,803 75,187 80,678 83,365 84,058 1,779 4,550 2016 93,526 92,743 91,119 93,324 103,602 104,612 105,852 5,975 4,858 2017 75,919 80,341 82,545 95,119 97,011 98,646 33,630 4,309 2018 73,492 68,125 78,902 90,348 96,685 335 4,864 2019 87,115 90,598 92,118 106,594 2,487 5,549 2020 83,900 86,700 86,700 5,196 4,719 2021 49,957 46,146 33,733 2,265 2022 31,487 9,336 185 Total $ 782,059 Cumulative net paid loss and LAE from the table below (612,456) Net reserves for loss and LAE before 2013 8,890 Total net reserves for loss and LAE $ 178,493 *Data presented for these calendar years is required supplementary information, which is unaudited. Cumulative Paid Losses and ALAE, Net of Reinsurance ($ in thousands) Years Ended December 31, Accident 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 2013 $ 4,763 $ 17,904 $ 36,890 $ 42,995 $ 41,158 $ 44,186 $ 47,101 $ 48,069 $ 48,322 $ 49,605 2014 9,700 30,863 42,141 50,785 49,906 52,450 53,290 53,615 55,737 2015 9,026 41,653 55,610 65,269 73,100 77,981 80,312 81,789 2016 36,592 57,638 70,253 78,070 81,516 85,794 87,966 2017 34,177 52,103 51,985 56,839 63,516 68,434 2018 25,552 60,149 67,262 80,448 90,791 2019 28,636 63,243 66,682 82,878 2020 24,468 54,950 63,468 2021 9,856 15,449 2022 16,339 Total $ 612,456 *Data presented for these calendar years is required supplementary information, which is unaudited. The table below presents the reconciliation of the net incurred and paid claims development to loss reserves in the consolidated balance sheets at December 31, 2022 by sub-category: ($ in thousands) 2022 Net reserves for losses and LAE: Short Tail/Monoline Specialty $ 158,903 Multi-line Solutions 360,695 Exited Lines 178,493 Reserves for losses and LAE, net of reinsurance 698,091 Reinsurance recoverable on unpaid claims: Short Tail/Monoline Specialty 147,435 Multi-line Solutions 252,673 Exited Lines 35,878 Total reinsurance recoverable on unpaid claims 435,986 Unallocated LAE 7,680 Reserves for losses and LAE at end of year $ 1,141,757 The following table presents supplementary information about average historical claims duration as of December 31, 2022, by sub-category is as follows: Average Annual Percentage Payout of Incurred Claims by Age, Net of Reinsurance Years Years 1 2 3 4 5 6 7 8 9 10 Short Tail/Monoline Specialty 56.0 % 24.0 % 10.1 % 6.2 % 2.9 % 0.1 % — % 0.6 % 0.1 % — % Multi-line Solutions 40.7 % 26.1 % 14.9 % 8.1 % 5.1 % 3.6 % 1.2 % — % 0.2 % 0.1 % Exited Lines 43.4 % 26.7 % 12.7 % 8.6 % 4.5 % 1.7 % 1.1 % 0.9 % 0.4 % — %

Premiums

Premiums	12 Months Ended
	Dec. 31, 2022
Insurance [Abstract]
Premiums	Premiums Direct and assumed premiums written by line of business pursuant to statutory accounting guidelines for the years ended December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Property $ 279,384 24.4 % $ 235,686 25.1 % Commercial Auto Liability $ 243,300 21.3 % $ 227,853 24.2 % General Liability $ 140,557 12.3 % $ 116,953 12.4 % Group Accident & Health $ 130,808 11.4 % $ 112,146 11.9 % Professional Liability $ 90,418 7.9 % $ 61,466 6.5 % Excess Liability $ 79,922 7.0 % $ 52,176 5.6 % Surety $ 79,062 6.9 % $ 51,792 5.6 % Workers’ Compensation $ 51,790 4.5 % $ 41,890 4.5 % Commercial Auto Physical Damage $ 48,711 4.3 % $ 39,897 4.2 % Total $ 1,143,952 100.0 % $ 939,859 100.0 % Certain premiums and benefits are assumed from and ceded to other insurance companies under various reinsurance agreements. The reinsurance agreements provide the Company with increased capacity to write larger risks and maintain its exposure to loss within its capital resources. The Company remains obligated for amounts ceded if reinsurers do not meet their obligations. The effects of reinsurance on premiums written and earned at December 31, 2022 and 2021 are as follows: 2022 2021 ($ in thousands) Written Earned Written Earned Direct premiums $ 1,012,239 $ 951,121 $ 842,318 $ 816,837 Assumed premiums 131,713 113,610 97,541 102,352 Ceded premiums (468,409) (448,737) (410,716) (419,366) Net premiums $ 675,543 $ 615,994 $ 529,143 $ 499,823 Ceded losses and LAE incurred $ 311,257 $ 248,360 The components of reinsurance recoverables and ceded unearned premium at December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Unpaid losses and loss adjustment expenses ceded $ 435,986 $ 381,338 Paid losses and loss adjustment expense ceded 107,228 90,761 Loss portfolio transfer 38,145 64,228 Reinsurance recoverables $ 581,359 $ 536,327 Ceded unearned premium $ 157,645 $ 137,973 The Company entered into agreements with several of its reinsurers, whereby the reinsurer established funded trust accounts with the Company as the sole beneficiary. These trust accounts provide the Company additional security to collect claim recoverables under reinsurance contracts; the Company does not carry these on the balance sheet as it will only have custody over these accounts upon the failure of the reinsurer to pay amounts due. At December 31, 2022, the market value of these accounts was approximately $128.0 million. The agreements provide that, as was customary in the past, the reinsurer will continue claim payment reimbursements without disturbing the trust balances. The trust amount will be adjusted periodically, by mutual agreement, based on loss reserve recoverables. During the first quarter of 2020, the Company entered into an LPT retroactive reinsurance agreement. Under the LPT, the Company received reinsurance protection of approximately $127.4 million above the ceded losses and LAE reserves and is subject to co-participations at specified amounts. During the years ended December 31, 2022 and 2021, the Company strengthened reserves for certain divisions covered by the LPT by $14.4 million and $28.0 million, respectively, resulting in an increase in the amount ceded under this agreement. The increase in the amount ceded during the years ended December 31, 2022 and 2021 were partially offset by $5.8 million and $11.9 million, respectively, of recognized gain. The following table presents the impact of the LPT on the consolidated statements of operations for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Strengthening of reserves subject to the LPT $ (14,385) $ (28,000) Reinsurance recoveries under the LPT 5,813 11,937 Pretax net impact of the LPT and strengthening of reserves subject to the LPT $ (8,572) $ (16,063) Certain ceded reinsurance contracts that transfer only significant timing risk and do not transfer sufficient underwriting risk are accounted for using the deposit method of accounting. The Company’s deposit asset was included in other assets on the consolidated balance sheets. The following table presents the Company’s deposit assets for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Deposit asset $ 41,801 $ 45,003

Commission and Fee Income

Commission and Fee Income	12 Months Ended
	Dec. 31, 2022
Revenue from Contract with Customer [Abstract]
Revenue from Contract with Customer	Commission and Fee Income SUA is a managing general insurance agent and reinsurance broker for property and casualty and accident and health risks in specialty niche markets. Commission and fee income is primarily generated from SUA for the placement of insurance policies on either a third-party insurance or reinsurance company. The Company’s disaggregated revenues from contracts with customers for the years ended December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 SUA commission revenue $ 3,224 $ 2,037 SUA fee income 1,597 1,185 Other 378 751 Total commission and fee income $ 5,199 $ 3,973 The Company’s contract assets from commission and fee income for the years ended December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Contract asset $ 1,292 $ 1,209

Underwriting, Acquisition and I

Underwriting, Acquisition and Insurance Expenses	12 Months Ended
	Dec. 31, 2022
Other Income and Expenses [Abstract]
Underwriting, Acquisition and Insurance Expenses	Underwriting, Acquisition and Insurance Expenses The Company’s underwriting, acquisition and insurance expenses at December 31, 2022 and 2021 consisted of the following: ($ in thousands) 2022 2021 Amortization of policy acquisition costs $ 65,695 $ 47,061 Other operating and general expenses 116,476 91,437 Total underwriting, acquisition and insurance expenses $ 182,171 $ 138,498

Reinsurance

Reinsurance	12 Months Ended
	Dec. 31, 2022
Insurance [Abstract]
Reinsurance	Premiums Direct and assumed premiums written by line of business pursuant to statutory accounting guidelines for the years ended December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Property $ 279,384 24.4 % $ 235,686 25.1 % Commercial Auto Liability $ 243,300 21.3 % $ 227,853 24.2 % General Liability $ 140,557 12.3 % $ 116,953 12.4 % Group Accident & Health $ 130,808 11.4 % $ 112,146 11.9 % Professional Liability $ 90,418 7.9 % $ 61,466 6.5 % Excess Liability $ 79,922 7.0 % $ 52,176 5.6 % Surety $ 79,062 6.9 % $ 51,792 5.6 % Workers’ Compensation $ 51,790 4.5 % $ 41,890 4.5 % Commercial Auto Physical Damage $ 48,711 4.3 % $ 39,897 4.2 % Total $ 1,143,952 100.0 % $ 939,859 100.0 % Certain premiums and benefits are assumed from and ceded to other insurance companies under various reinsurance agreements. The reinsurance agreements provide the Company with increased capacity to write larger risks and maintain its exposure to loss within its capital resources. The Company remains obligated for amounts ceded if reinsurers do not meet their obligations. The effects of reinsurance on premiums written and earned at December 31, 2022 and 2021 are as follows: 2022 2021 ($ in thousands) Written Earned Written Earned Direct premiums $ 1,012,239 $ 951,121 $ 842,318 $ 816,837 Assumed premiums 131,713 113,610 97,541 102,352 Ceded premiums (468,409) (448,737) (410,716) (419,366) Net premiums $ 675,543 $ 615,994 $ 529,143 $ 499,823 Ceded losses and LAE incurred $ 311,257 $ 248,360 The components of reinsurance recoverables and ceded unearned premium at December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Unpaid losses and loss adjustment expenses ceded $ 435,986 $ 381,338 Paid losses and loss adjustment expense ceded 107,228 90,761 Loss portfolio transfer 38,145 64,228 Reinsurance recoverables $ 581,359 $ 536,327 Ceded unearned premium $ 157,645 $ 137,973 The Company entered into agreements with several of its reinsurers, whereby the reinsurer established funded trust accounts with the Company as the sole beneficiary. These trust accounts provide the Company additional security to collect claim recoverables under reinsurance contracts; the Company does not carry these on the balance sheet as it will only have custody over these accounts upon the failure of the reinsurer to pay amounts due. At December 31, 2022, the market value of these accounts was approximately $128.0 million. The agreements provide that, as was customary in the past, the reinsurer will continue claim payment reimbursements without disturbing the trust balances. The trust amount will be adjusted periodically, by mutual agreement, based on loss reserve recoverables. During the first quarter of 2020, the Company entered into an LPT retroactive reinsurance agreement. Under the LPT, the Company received reinsurance protection of approximately $127.4 million above the ceded losses and LAE reserves and is subject to co-participations at specified amounts. During the years ended December 31, 2022 and 2021, the Company strengthened reserves for certain divisions covered by the LPT by $14.4 million and $28.0 million, respectively, resulting in an increase in the amount ceded under this agreement. The increase in the amount ceded during the years ended December 31, 2022 and 2021 were partially offset by $5.8 million and $11.9 million, respectively, of recognized gain. The following table presents the impact of the LPT on the consolidated statements of operations for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Strengthening of reserves subject to the LPT $ (14,385) $ (28,000) Reinsurance recoveries under the LPT 5,813 11,937 Pretax net impact of the LPT and strengthening of reserves subject to the LPT $ (8,572) $ (16,063) Certain ceded reinsurance contracts that transfer only significant timing risk and do not transfer sufficient underwriting risk are accounted for using the deposit method of accounting. The Company’s deposit asset was included in other assets on the consolidated balance sheets. The following table presents the Company’s deposit assets for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Deposit asset $ 41,801 $ 45,003

Stock Based Compensation

Stock Based Compensation	12 Months Ended
	Dec. 31, 2022
Share-Based Payment Arrangement [Abstract]
Stock Based Compensation	Stock Based Compensation Legacy Programs The Legacy Programs were active during the year ended December 31, 2021 and allowed key employees to purchase the Company’s common stock at a price based on fair value of the Company at the end of the quarter in which the employee commits to the purchase. The Company then matched all purchases with stock grants. The programs required an initial cash payment of at least 30% of the committed fair value of the purchase with any remaining commitment recorded as a note receivable to the Company which is included in Stockholders’ Equity. Grants awarded vest after two conditions are met (i) the employee has worked for us for three years Under the Legacy Programs, the Company sold 63,374 shares of its common stock during the year ended December 31, 2021. In accordance with the plan, the Company granted a match of 63,374 shares of its common stock during the year ended December 31, 2021. During the year ended December 31, 2021, members of the Board of Directors were awarded 51,889 common shares with a service period of between 0 to 3 years. Under the Legacy Programs, the Company offered employees the option to finance up to 70% of the purchased shares with a stock note receivable. These stock notes receivable are recorded as a reduction to Stockholders’ Equity. The stock notes receivable bear interest at a rate ranging from 0.95% to 2.80%, based on the Internal Revenue Service applicable federal rates. The following table presents common stock notes receivable related to Legacy Programs at both December 31, 2022 and 2021: ($ in thousands) 2022 2021 Common stock notes receivable $ 512 $ 1,630 During the year ended December 31, 2021, several employees who previously received common stock awards under the Legacy Programs notified the Company that they would not be repaying the remaining balance on their stock notes receivable. Under the terms of the Legacy Programs, employees would return their common shares financed by the remaining stock note balance and forfeit the same number of award shares. During the year ended December 31, 2021, 21,314 common shares financed and awarded were returned and forfeited. The return of 10,657 financed shares resulted in the cancellation of $0.8 million in stock notes for the year ended December 31, 2021. Forfeitures of the 10,657 award shares resulted in the reversal of previously recognized stock compensation expense of $0.8 million for the year ended December 31, 2021. Long Term Incentive Plan During the year ended December 31, 2022 and 2021, under the 2021 Plan the Compensation Committee approved 198,842 and 217,395 shares of common stock, respectively. During the year ended December 31, 2022, members of the Board of Directors were awarded 15,196 common shares with a service period of one year. The shares granted to employees and the Board of Directors during the year ended December 31, 2022 and 2021 were valued at approximately $2.6 million and $2.5 million, respectively, based on the grant date fair value. A summary of the equity awards, target payout ranges based on meeting award conditions and authorized target common shares is as follows: Award Requisite Authorized Target Year ended December 31, 2022 Market condition awards 0% — 150% 3 years 28,495 Performance condition awards 0% — 150% 3 years 26,210 Restricted share and stock unit awards N/A 1 to 3 years 144,137 198,842 Year ended December 31, 2021 Market condition awards 0% — 150% 3 years 46,474 Performance condition awards 0% — 150% 3 years 29,501 Restricted stock unit awards N/A 3 years 141,420 217,395 A summary of the status of the Company’s non-vested common stock awards from the Legacy Programs and the 2021 Plan is presented below: Weighted-Average Number of Common Shares Non-vested at January 1, 2022 $ 13.23 375,643 Granted 14.17 198,842 Vested 15.16 (144,042) Forfeited 12.51 (10,547) Non-vested at December 31, 2022 $ 12.55 419,896 Non-vested at January 1, 2021 $ 19.47 84,671 Granted 11.95 332,658 Vested 14.20 (6,514) Forfeited 16.01 (35,172) Non-vested at December 31, 2021 $ 13.23 375,643 As of December 31, 2022 the total unrecognized compensation cost related to non-vested, share-based compensation awards was $2.8 million and the weighted average period over which that cost is expected to be recognized is 1.6 years. Stock-based compensation expense for the years ended December 31, 2022 and 2021 is summarized as follows: ($ in thousands) 2022 2021 Stock-based compensation expense Stock-based compensation expense $ 2,325 $ 1,365 Forfeitures (38) (843) Total $ 2,287 $ 522

Earnings Per Share

Earnings Per Share	12 Months Ended
	Dec. 31, 2022
Earnings Per Share [Abstract]
Earnings Per Share	Earnings Per Share The following table presents a reconciliation of the numerator and denominator of the basic and diluted earnings per share computations contained in the consolidated financial statements for the years ended December 31, 2022 and 2021. ($ in thousands, except for share and per share amounts) 2022 2021 Numerator Net income $ 39,396 $ 38,317 Less: Undistributed income allocated to participating securities (18,879) (18,507) Net income attributable to common shareholders (numerator for basic earnings per share) 20,517 19,810 Add back: Undistributed income allocated to participating securities 18,879 18,507 Net income (numerator for diluted earnings per share under the two-class method) $ 39,396 $ 38,317 Denominator Basic weighted-average common shares 16,568,393 16,308,712 Preferred shares (if converted method) 15,245,533 15,235,568 Contingently issuable instruments (treasury stock method) 519,080 723,146 Market condition awards (contingently issuable) 94,936 67,598 Performance awards (contingently issuable) 39,148 — Restricted stock units (treasury stock method) 186,104 133,024 Diluted weighted-average common share equivalents 32,653,194 32,468,048 Basic earnings per share $ 1.24 $ 1.21 Diluted earnings per share $ 1.21 $ 1.18 The Company’s Preferred Shares participate in dividends and distributions with common stock on an as-converted basis and represent a participating security. Anti-dilutive instruments are excluded from the calculation of diluted weighted-average common share equivalents as they would have an anti-dilutive impact. The following table presents instruments that were excluded from the calculation of diluted weighted-average common share equivalents at both December 31, 2022 and 2021. 2022 2021 Contingently issuable instruments (treasury stock method) 60,576 — The Company’s common and preferred shares financed by stock notes are contingently issuable instruments where the holder must return, all or part of, the shares if the stock notes are not paid off. The following table presents common share equivalents of contingently issuable instruments that were excluded from basic earnings per share in shares for the years ended December 31, 2022 and 2021: 2022 2021 Common shares 22,919 192,609 Preferred shares, if converted 1,059,602 1,235,420 Total 1,082,521 1,428,029 The impact of the contingently issuable instruments on diluted earnings per share was calculated using the treasury stock method and included in the reconciliation of the denominator of the basic and diluted earnings per share computations for the years ended December 31, 2022 and 2021.

Employee Benefit Plans

Employee Benefit Plans	12 Months Ended
	Dec. 31, 2022
Retirement Benefits [Abstract]
Employee Benefit Plans	Employee Benefit Plans The Company sponsors the 401(k) Plan (the “Plan”). The Plan, available to substantially all its employees, is subject to provisions of the Employee Retirement Income Security Act of 1974. The Company matches employee contributions on a discretionary basis. The following table presents the Company’s expensed matching contributions for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 401(k) matching contributions $ 2,389 $ 2,288

Related Party Transactions

Related Party Transactions	12 Months Ended
	Dec. 31, 2022
Related Party Transactions [Abstract]
Related Party Transactions	Related Party Transactions Westaim In 2014 and continuing through 2015, Westaim HIIG LP acquired a majority of the Company’s common stock. As of December 31, 2022 and 2021, Westaim HIIG LP owns 44.5% and 71.0% of the Company’s common stock, respectively. The changes in Westaim HIIG LP’s ownership percentage were primarily due to transactions between Westaim HIIG LP and its partners. In 2015, the Company purchased 3,076,924 shares of Westaim common stock for $8.4 million. The Company’s investment in Westaim is included in equity securities on the consolidated balance sheets. The unrealized loss on this investment for the years ended December 31, 2022 and 2021 is as follows: ($ in thousands) 2022 2021 Unrealized losses on investment in Westaim $ (2,283) $ (1,971) On April 24, 2020, Westaim HIIG LP affiliates participated in the Company’s preferred share rights offering and purchased $68.6 million of Preferred Shares in exchange for $68.1 million of cash and $0.5 million of stock notes. Within this group, Westaim purchased $44.0 million of Preferred Shares in exchange for $44.0 million of cash. As of December 31, 2022 and 2021, Westaim owns 44.7% of the Company’s preferred stock. Westaim performs consulting and certain other services for the Company pursuant to an agreement (the “Management Services Agreement”). Pursuant to the Management Services Agreement, the Company is required to pay Westaim $0.5 million a year plus expenses. The agreement will be effective until the termination date. The termination date is the earliest of (a) the date on which Westaim HIIG LP owns less than 8% of the number of shares outstanding, (b) the date on which the Company’s initial public offering is consummated, or (c) the date upon which a change in control occurs. Pursuant to the current Management Services Agreement, at December 31, 2022 and 2021, the Company incurred the following expenses related to services provided by Westaim: ($ in thousands) 2022 2021 Management services agreement $ 500 $ 500 RISCOM During 2016, the Company entered into an agency agreement with RISCOM, in which the Company holds a 20% ownership interest, for wholesale brokerage services in addition to the already existing managing general agency agreement between the parties. Net earned premium and gross written commissions related to these agreements at December 31, 2022 and 2021 is summarized as follows: ($ in thousands) 2022 2021 Net earned premium $ 91,051 $ 76,701 Gross written commissions 23,472 21,256 Premiums receivable from RISCOM at December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Premiums receivable $ 9,940 $ 11,334 Reinsurance The Company has reinsurance agreements with Everest Re, an affiliate of Mt. Whitney Securities, LLC, a limited partner of Westaim HIIG LP and holder of Preferred Shares. Reinsurance premiums ceded related to the agreement at December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Reinsurance premiums ceded $ 59,592 $ 101,154 Reinsurance recoverable from Everest Re, net of premium payables for the years ended December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Reinsurance recoverable, net of premium payables $ 177,455 $ 168,847 Arena During the year ended December 31, 2022, the Company began investing in multiple investment products issued by Arena Special Opportunities Partners (Feeder) II, LP (“Arena SOP II”), managed by Arena, which is affiliated with Westaim. The investment products include senior and junior notes issued by the Arena SOP II to raise capital from limited partners to fund purchases of investments. The return on the investments is used to pay interest on the senior and junior notes based on target returns of each class. The senior and junior notes are debt securities classified as held to maturity and presented on the balance sheet within fixed maturity securities, held to maturity. As of December 31, 2022, the Company invested $3.4 million in the senior and junior notes. During the second quarter of 2021, the Company began investing in an asset-backed securities investment account managed by Arena. The asset-backed securities are within fixed maturity securities, available for sale on the consolidated balance sheet. As of December 31, 2022, the Company has no unfunded commitment related to this investment. Other The following table reflects advisory and professional services fees and expense reimbursements paid to various affiliated shareholders and directors during the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Professional fees and reimbursements $ 3,387 $ 3,669 See Notes 7, 8 and 11 for investments involving affiliated companies and additional related party transactions. See Note 13 for related party transactions related to the Company’s preferred share rights offering.

Commitment and Contingencies

Commitment and Contingencies	12 Months Ended
	Dec. 31, 2022
Commitments and Contingencies Disclosure [Abstract]
Commitments and Contingencies	Commitments and Contingencies Litigation The Company is named as a defendant in various legal actions arising from claims made under insurance policies and contracts. Those actions are considered by the Company in estimating the losses and loss adjustment expense reserves. Also, from time to time, the Company is a defendant in various legal actions that relate to bad faith claims, disputes with third parties or that involve alleged errors and omissions. The Company records accruals for these items to the extent the losses are probable and reasonably estimable. Although the ultimate outcome of these matters cannot be determined at this time, based on present information, the availability of insurance coverage and advice received from outside legal counsel, the Company’s management believes the resolution of any such matters will not, individually or in the aggregate, have a material adverse effect on the Company’s Consolidated Balance Sheets, Consolidated Statements of Operations or Consolidated Statements of Cash Flows. During the years ended December 31, 2022 and 2021, the Company recorded no provision for various contingencies. Indemnification In conjunction with the sale of business assets and subsidiaries, the Company has provided indemnifications to certain of the buyers. Certain indemnifications cover typical representations and warranties related to the responsibilities to perform under the sales contracts. The amount of potential exposure covered by the indemnifications is difficult to determine because the indemnifications cover a variety of matters, operations and scenarios. Certain of these indemnifications have no time limit. As of December 31, 2022, the Company does not have reason to believe any such significant claims exist. Contingent Consideration Related to Acquisitions The Company potentially owes earn-out liabilities to former owners of assets and business acquired. No earn-out liabilities existed as of December 31, 2022 and 2021. The following table presents earn-out payments to former owners during the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Earn-out payments to former owners $ — $ 554

Regulatory Matters

Regulatory Matters	12 Months Ended
	Dec. 31, 2022
Insurance [Abstract]
Regulatory Matters	Regulatory Matters A significant amount of the consolidated assets represent assets of the Company’s insurance company subsidiaries, HSIC, IIC, GMIC and OSIC. IIC, OSIC and GMIC are all direct and indirect wholly-owned subsidiaries of HSIC. HSIC is restricted by Texas law as to the amount of dividends it may pay without the approval of regulatory authorities. The maximum amount of dividends which can be paid by HSIC without prior approval is subject to restrictions relating to policyholder surplus, net income, and dividends declared or distributed during the preceding 12 months. As of December 31, 2022, HSIC is not restricted to paying ordinary dividends. HSIC did not declare or pay any dividends during the years ended December 31, 2022 and 2021. Property and casualty insurance companies are subject to certain Risk Based Capital (“RBC”) requirements as specified by the National Association of Insurance Commissioners (“NAIC”). Under those requirements, the amount of capital and surplus maintained by a property and casualty insurance company is to be determined based on the various risk factors related to it. At December 31, 2022 and 2021, the Company’s insurance company subsidiaries met the RBC requirements. The capital and surplus and RBC level of HSIC on a consolidated statutory basis (including IIC, GMIC OSIC, and BIC) for the years ended December 31, 2022 and 2021 were as follows: ($ in thousands) 2022 2021 Statutory capital and surplus $ 408,167 $ 369,583 RBC authorized control level 110,635 84,968

Statutory Accounting Principles

Statutory Accounting Principles	12 Months Ended
	Dec. 31, 2022
Insurance [Abstract]
Statutory Accounting Principles	Statutory Accounting Principles The statutory capital and surplus for the Company’s principal operating subsidiaries for the years ended December 31, 2022 and 2021 was as follows: ($ in thousands) 2022 2021 HSIC $ 408,167 $ 369,583 IIC 272,413 215,508 GMIC 259,311 209,347 OSIC 21,270 21,095 These amounts include ownership interests in affiliated insurance subsidiaries. The statutory net income (loss) for the Company’s principal operating subsidiaries for the years ended December 31, 2022 and 2021 was as follows: ($ in thousands) 2022 2021 HSIC $ 10,860 $ 5,880 IIC 25,394 7,315 GMIC 14,091 (947) BIC — (67) OSIC 173 31 See note 4 for additional information regarding the sale of BIC.

Subsequent Events

Subsequent Events	12 Months Ended
	Dec. 31, 2022
Subsequent Events [Abstract]
Subsequent Events	Subsequent Events Reverse Stock Split On September 23, 2022, the Board of Directors approved a 4-for-1 reverse stock split of the Company’s common stock. The stock split became effective January 3, 2023. All share and per share information included in the accompanying consolidated financial statements and notes to the consolidated financial statements have been retroactively adjusted to reflect the stock split of common stock for all periods presented. 2022 Long-Term Incentive Plan On September 23, 2022, the Board of Directors approved the Company’s 2022 Long-Term Incentive Plan (the “2022 Plan”), which became effective on January 12, 2023. The 2022 Plan stated that 3,200,516 shares of common stock were available for issuance. Employee Stock Purchase Plan On September 23, 2022, the Board of Directors approved the Company’s 2022 Employee Stock Purchase Plan (the “ESPP”), which became effective on January 12, 2023. The ESPP stated that 376,531 shares of common stock were available for sale. New Credit Facility On January 3, 2023, the Company entered into a term sheet with Truist Securities, Inc. (the “Term Sheet”) setting forth expected material terms to refinance its existing credit agreement. The Term Sheet provides a new unsecured credit facility (the “New Credit Facility”), with Truist Securities, Inc. to lead a syndicate of participating banks, which is expected to provide the Company with up to a $150.0 million revolving credit facility and a letter of credit sub-facility of up to $10.0 million. The New Credit Facility is also expected to permit the incurrence of an uncommitted accordion facility up to $50.0 million, subject to certain conditions to be agreed. The Company expects to close on the New Credit Facility in the first quarter of 2023. Initial Public Offering On January 4, 2023, the Company announced the launch of its initial public offering (“IPO”) of its common stock. On January 12, 2023, the Company priced its IPO of 8,952,383 shares of its common stock, with 4,750,000 shares offered by the Company and 4,202,383 shares sold by selling stockholders, at a public price of $15.00 per share. The shares began trading on January 13, 2023 on the Nasdaq Global Select Market under the ticker symbol “SKWD.” The Company completed its IPO on January 18, 2023. The underwriters exercised in full their option to purchase 1,342,857 additional shares of common stock from the selling stockholders, at a price per share of $15.00. The Company’s net proceeds from the IPO were approximately $62.3 million, after deducting underwriting discounts and specific incremental expenses directly attributable to the IPO. Upon the closing of its IPO, the Company filed an amended and restated certificate of incorporation which, among other things, increased the number of authorized shares consisting of 500,000,000 shares of common stock, par value $0.01 per share, and 10,000,000 shares of preferred stock, par value $0.01 per share. The Preferred Shares were subject to mandatory conversion at the Mandatory Conversion Rate upon the closing of an IPO. On January 18, 2023, the 1,969,660 Preferred Shares converted to 16,305,113 shares of common stock.

SCHEDULE I__ SUMMARY OF INVESTM

SCHEDULE I — SUMMARY OF INVESTMENTS — OTHER THAN IN RELATED PARTIES	12 Months Ended
	Dec. 31, 2022
SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Abstract]
SCHEDULE I — SUMMARY OF INVESTMENTS — OTHER THAN IN RELATED PARTIES	SCHEDULE I — SUMMARY OF INVESTMENTS — OTHER THAN IN RELATED PARTIES ($ in thousands) Cost Fair Value Amount on December 31, 2022 Fixed maturity securities, available for sale: U.S. government securities $ 50,416 $ 48,541 $ 48,541 Corporate securities and miscellaneous 255,116 235,129 235,129 Municipal securities 65,836 57,727 57,727 Residential mortgage-backed securities 134,844 119,856 119,856 Commercial mortgage-backed securities 40,129 36,495 36,495 Asset-backed securities 116,275 109,824 109,824 Total fixed maturity securities, available for sale 662,616 607,572 607,572 Fixed maturity securities, held to maturity: Asset-backed securities 52,467 46,771 52,467 Total fixed maturity securities, held to maturity 52,467 46,771 52,467 Equity securities: Common stocks 50,484 55,996 55,996 Preferred stocks 11,798 8,771 8,771 Mutual funds 53,968 55,402 55,402 Total equity securities 116,250 120,169 120,169 Mortgage loans 51,859 52,842 51,859 Short-term investments 121,158 121,158 121,158 Total investments $ 1,004,350 $ 948,512 $ 953,225

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	SCHEDULE II — CONDENSED FINANCIAL INFORMATION OF REGISTRANT BALANCE SHEETS (PARENT COMPANY) December 31, ($ in thousands) 2022 2021 Assets Investments: Investment in subsidiaries $ 503,549 $ 517,326 Short-term investments, at fair value 25 25 Total investments 503,574 517,351 Cash and cash equivalents 8,909 5,849 Restricted cash — 156 Deferred income taxes 19,655 15,182 Goodwill and intangible assets, net 12,641 12,641 Other assets 6,992 4,218 Total assets $ 551,771 $ 555,397 Liabilities and Stockholders’ Equity Liabilities: Accounts payable and accrued liabilities $ 1,500 $ 788 Notes payable 50,000 50,000 Subordinated debt, net of debt issuance costs 78,609 78,529 Total liabilities 130,109 129,317 Stockholders’ Equity: Stockholders’ equity 421,662 426,080 Total liabilities and stockholders’ equity $ 551,771 $ 555,397 SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES SCHEDULE II — CONDENSED STATEMENTS OF OPERATIONS (PARENT COMPANY) December 31, ($ in thousands) 2022 2021 Revenues: Net investment income $ 2,567 $ 2,383 Net investment losses (6) — Total revenues 2,561 2,383 Expenses Interest expense 6,407 4,621 Amortization expense 81 81 Total expenses 6,488 4,702 Loss before income tax expense (3,927) (2,319) Income tax benefit (1,209) (487) Net loss before equity in earnings of subsidiaries (2,718) (1,832) Equity in undistributed earnings of subsidiaries 42,114 40,149 Net income $ 39,396 $ 38,317 SKYWARD SPECIALTY INSURANCE GROUP, INC. AND SUBSIDIARIES SCHEDULE II — CONDENSED STATEMENTS OF CASH FLOWS (PARENT COMPANY) December 31, ($ in thousands) 2022 2021 Cash flows from operating activities: Net income $ 39,396 $ 38,317 Adjustments to reconcile net income to net cash used in operating activities (42,672) (40,447) Net cash provided by operating activities (3,276) (2,130) Cash flows from investing activities: Capital contribution to subsidiaries — (10,000) Distributions from investment in subsidiaries 4,000 4,000 Net cash provided by (used in) investing activities 4,000 (6,000) Cash flows from financing activities: Employee share purchases 2,180 1,380 Net cash provided by financing activities 2,180 1,380 Net increase (decrease) in cash and cash equivalents and restricted cash 2,904 (6,750) Cash and cash equivalents and restricted cash at beginning of year 6,005 12,755 Cash and cash equivalents and restricted cash at end of year $ 8,909 $ 6,005 Supplemental disclosure of cash flow information: Cash paid for interest $ 5,761 $ 4,669

SCHEDULE IV__ REINSURANCE

SCHEDULE IV — REINSURANCE	12 Months Ended
	Dec. 31, 2022
SEC Schedule, 12-17, Insurance Companies, Reinsurance [Abstract]
SCHEDULE IV — REINSURANCE	SCHEDULE IV — REINSURANCE December 31, 2022 2021 ($ in thousands) Accident & Property & Accident & Property & Gross amount $ 130,377 $ 881,862 $ 111,759 $ 730,559 Ceded to other companies (70,291) (398,118) (68,350) (342,366) Assumed from other companies 431 131,282 387 97,154 Net amount $ 60,517 $ 615,026 $ 43,796 $ 485,347 Percentage of amount assumed to net 0.7 % 21.3 % 0.9 % 20.0 %

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	SCHEDULE V — VALUATION AND QUALIFYING ACCOUNTS ($ in thousands) Valuation Allowance for Allowance for Balance at January 1, 2021 $ 586 $ — $ 1,146 Charged to costs and expenses — — 18 Amounts written off — — (903) Balance at December 31, 2021 586 — 261 Charged to costs and expenses — — 584 Amounts written off — — (216) Balance at December 31, 2022 $ 586 $ — $ 629

SCHEDULE VI__ SUPPLEMENTAL INFO

SCHEDULE VI — SUPPLEMENTAL INFORMATION CONCERNING PROPERTY-CASUALTY INSURANCE OPERATIONS	12 Months Ended
	Dec. 31, 2022
SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters [Abstract]
SCHEDULE VI — SUPPLEMENTAL INFORMATION CONCERNING PROPERTY-CASUALTY INSURANCE OPERATIONS	SCHEDULE VI — SUPPLEMENTAL INFORMATION CONCERNING PROPERTY-CASUALTY INSURANCE OPERATIONS December 31, ($ in thousands) 2022 2021 Deferred policy acquisition costs $ 68,938 $ 59,456 Reserve for losses and loss adjustment expenses 1,141,757 979,549 Unearned premiums 442,509 363,288 Net earned premium (1) 615,994 499,823 Net investment income 36,931 24,646 Losses and loss adjustment expenses (current year) (1) 393,939 338,348 Losses and loss adjustment expenses (prior years) (1)(2) 14,385 28,000 Amortization of policy acquisition costs (1) 65,695 47,061 Paid claims and claim adjustment expenses (1) 300,764 249,739 Net premiums written (1) 675,543 529,143 Ceded unearned premium 157,645 137,973 Deferred ceding commission 29,849 30,500 (1) Amount is presented net of reinsurance (2) Amount does not include gain or loss on retroactive reinsurance which is included in losses and loss adjustment expenses presented on the Consolidated Statements of Operations

Summary of Significant Accoun_2

Summary of Significant Accounting Policies (Policies)	12 Months Ended
	Dec. 31, 2022
Accounting Policies [Abstract]
Basis of Presentation	Basis of Presentation The Company’s consolidated financial statements have been prepared in accordance with generally accepted accounting principles (“GAAP”) in the United States of America, and include accounts of the Company and its subsidiaries as of and for the years ended December 31, 2022 and 2021. All intercompany transactions and balances have been eliminated in consolidation.
Use of Estimates	Use of Estimates The preparation of consolidated financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosures of contingent assets and liabilities at the date of the consolidated financial statements and the reported amounts of revenue and expenses during the reporting period. Actual results could differ materially from these estimates.
Cash and Cash Equivalents	Cash and Cash Equivalents Cash and cash equivalents include cash on hand and highly liquid short-term investments. Short-term investments purchased with an original maturity of three months or less are considered to be cash equivalents. The carrying value of the Company’s cash and cash equivalents approximates fair value.
Restricted Cash	Restricted Cash Cash with a legal restriction as to withdrawal or use by the consolidated group is recorded as restricted cash. The carrying value of the Company’s restricted cash approximates fair value. SUA collects premiums from clients, and after deducting commissions and any applicable fees, remits these premiums to the Company’s insurance companies, noted within the Nature of Operations or to third-party insurance companies. SUA holds unremitted insurance premiums in a fiduciary capacity to third-party insurance companies, as restricted cash. The Company is required by state regulations to maintain assets on deposit with certain states and hold cash as collateral for certain reinsurance balances. Cash it holds in a depository account for others, or which is restricted by a state, is recorded as restricted cash.
Investments	Investments Available for Sale Investments in fixed maturity securities are classified as available for sale and are reported at fair value based on quoted market prices or dealer quotes. Unrealized gains and losses for fixed maturity securities are excluded from net income and reported in stockholders’ equity, net of taxes, as a component of accumulated other comprehensive income (loss). If quoted market prices or dealer quotes are not available, the Company estimates fair value based on recent trading information. Premiums and discounts on mortgage-backed securities are amortized using the retroactive method adjusted for anticipated prepayments and the estimated economic life of the securities. Adjustments related to changes in prepayment assumptions are included in net investment income. Held to maturity Investments in fixed maturity securities where the Company has demonstrated the intent and ability to hold until maturity have been classified as held to maturity and are reported at amortized cost. Other-than-Temporary Impairments The Company evaluates declines in the market value of invested assets below amortized cost, for other-than-temporary impairment losses, on a quarterly basis. Impairment losses for declines in the value of its fixed maturity securities below amortized cost attributable to issuer-specific events are based on all relevant facts and circumstances for each investment and are recognized when appropriate. For all investments with unrealized losses due to market conditions or industry-related events where the Company does not have intent to sell the security and it has the ability to hold the investment for either a period of time sufficient to allow a market recovery or to maturity, declines in value below cost are not assumed to be other-than-temporary. When the Company considers the impairment of the value of an investment to be other-than-temporary, it reports the decrease in value in net income within the Consolidated Statements of Operations and a corresponding reduction in carrying value on the consolidated balance sheet. Equity securities with a readily determinable fair value Equity securities consists of common stock or preferred stock. Mutual funds, including those that invest mostly in debt securities, are classified as equity securities. Investments in equity securities with a readily determinable fair value are carried on the balance sheet at fair value using quoted market prices. Changes in the carrying value of equity securities are included in net investment (losses) gains within the Consolidated Statements of Operations. Mortgage loan s Investments in mortgage loans are classified as held for investment and carried on the balance sheet at cost adjusted for unamortized: premiums, discounts and loan fees. When an amount is determined to be uncollectible, the Company writes off the uncollectible amount in the period it was determined to be uncollectible. Interest on the loans is recognized as interest receivable which the Company includes in other assets on the consolidated balance sheet. Other long-term investments Other long-term investments include investments in equity and equity securities of non-public entities and indirect investments in loans and loan collateral. The Company has equity investments in certain limited partnerships and corporations where it has significant influence but not control. The analysis of entities that are variable interest entities indicated the Company is not the primary beneficiary, and would not have to consolidate these entities. Equity method is used to account for these investments. Under the equity method, initial investment is recorded at cost and is subsequently adjusted based on its proportionate share of distributions and net income or loss of the equity method investee. The difference between the cost of an investment and its proportionate share of the underlying equity in net assets recorded on the investee’s books is a component of investment income. The Company amortizes the difference as an adjustment to its pro-rata share of equity method income over the useful life which is based on the underlying asset. The Company does not have significant influence in its investments in equity securities of non-public entities. When these securities do not have a readily determinable fair value, the Company carries these investments at cost, minus impairment, if any, and changes resulting from observable price changes in orderly transactions for identical or similar investments of the same issuer. Investments in indirect collateralized loans and loan collateral are held through and accounted for as an ownership interest in an unconsolidated subsidiary. The Company’s ownership interests in unconsolidated subsidiaries consists of investments in entities such as partnerships, joint ventures, and special purpose investment vehicles. The Company has significant influence, but not control of these unconsolidated subsidiaries and uses the equity method to account for these investments. Short-Term Investments Short-term investments consist primarily of money market funds and are carried at cost which approximates fair value. Net Investment Income and Net Realized Gains and Losses Net investment income consists of interest, dividends and equity in earnings (losses) of investees net of investment expenses such as investment management expenses. Interest income is recognized on the accrual basis, and dividends as earned at the ex-dividend date. Interest income on mortgage-backed and asset-backed securities is recognized using the effective-yield method based on estimated principal repayments. Included in interest income is the amortization of premium and accretion of discounts on debt securities. Net realized gains and losses on investments are recognized in net income based upon the specific identification method.
Reinsurance	Reinsurance Reinsurance Accounting In the normal course of business, the Company purchases prospective reinsurance for certain lines of business on a proportional, excess of loss and facultative basis. Proportional reinsurance requires the Company to share the losses and expenses with the reinsurer in exchange for a share of the premiums. Excess of loss reinsurance shares losses, either a proportion of or in its entirety, above a certain dollar threshold, in exchange for a negotiated cost. Facultative reinsurance covers specific risks and/or policies on either a proportional or excess of loss basis. Ceded unearned premium and reinsurance balances recoverable—on paid and unpaid losses and settlement expenses—are reported separately as assets, instead of netting them with the related liabilities, since reinsurance does not relieve the Company of its legal liability to its policyholders. Reinsurance on unpaid losses and settlement expenses represent estimates of the portion of the liabilities recoverable from reinsurers. On the Consolidated Statements of Operations, net earned premium, losses and loss adjustment expenses, net and underwriting, acquisition and insurance expenses are presented net of reinsurance ceded. The Company purchases retroactive reinsurance on certain lines of business in the form of loss portfolio transfers (“LPT”) and adverse development covers. These contracts provide indemnification of losses related to past loss events where the reinsurer shares losses, either a proportion of or in its entirety, depending on certain dollar thresholds. Income generated from retroactive reinsurance contracts is deferred and amortized into net income over the settlement period and losses are charged to net income immediately. Subsequent changes in the measurement of the retroactive reinsurance contract are accounted for under a full retrospective method. Deposit Accounting Certain ceded reinsurance contracts, which management determines do not transfer significant insurance risk, are accounted for using the deposit method of accounting. The evaluation of the transfer of significant insurance risk involves an assessment of both timing risk and underwriting risk. Management may determine that a reinsurance contract does not transfer significant insurance risk if either underwriting risk or timing risk or both are not deemed to have been transferred. For those contracts that transfer only significant timing risk and do not transfer sufficient underwriting risk, a deposit asset is recorded equal to the initial cash outflow under the contract, which will then be offset by cash inflows received from the reinsurers. To the extent cash outflows are expected to differ from expected cash inflows, an accretion rate is established at inception of the contract based on actuarial estimates whereby the deposit accounting asset is increased/decreased to the estimated amount receivable over the contract term. The accretion of the deposit is based on the expected rate of return implied from the estimated cash inflows and outflows under the contract. Periodically, the Company reassesses the estimated ultimate receivable and the related expected rate of return on the deposit asset. The accretion of the deposit asset, including any changes in accretion resulting from changes in estimated cash flows, are reflected as part of investment income in the Company’s results of operations. Several reinsurance contracts require deposit accounting treatment due to not transferring sufficient underwriting risk. There were no reinsurance contracts that require deposit accounting treatment due to not transferring sufficient timing risk. Reinsurance Recoverables Reinsurance does not relieve the Company of its legal liability to its policyholders. The Company continuously monitors the financial condition of its reinsurers. As part of its monitoring efforts, the Company reviews the reinsurers’ annual financial statements. The Company also reviews insurance industry developments that may impact the financial condition of its reinsurers. The Company analyzes the credit risk associated with its reinsurance recoverables by monitoring the financial strength rating of its reinsurers from A.M. Best, a widely recognized rating agency with an exclusive insurance industry focus. It also assesses the adequacy of collateral obtained, where applicable. Should its reinsurers fail to fulfill their obligations, the Company has access to collateral from various reinsurers. The following table presents reinsurance collateral for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Reinsurance collateral $ 253,870 $ 230,908
Concentration of Credit Risk	Concentration of Credit Risk Other than reinsurance recoverables, financial instruments that potentially subject us to concentrations of credit risk are primarily cash and cash equivalents, restricted cash, investments and premiums receivable. Cash equivalents and short-term investments include investments in money market funds and securities backed by the U.S. government. Investments are diversified throughout many industries and geographic regions. The Company limits the amount of credit exposure with any one financial institution or issuer and believes no significant concentration of credit
Deferred Policy Acquisition Costs	Deferred Policy Acquisition Costs Policy acquisition costs consist of commissions and premium taxes that vary with and are directly related to the successful production of new or renewal business. The Company defers policy acquisition costs and related ceding commissions and charge or credit them to earnings in proportion with the premium earned over the life of the policy. A premium deficiency is recognized if the sum of expected losses, loss adjustment expenses, and unamortized acquisition costs exceed its related unearned premiums. The Company first recognizes a premium deficiency by charging any unamortized acquisition costs to expense to the extent required to eliminate the deficiency. If its premium deficiency is greater than unamortized acquisition costs, it accrues a liability for the excess deficiency. Anticipated investment income is considered in the determination of premium deficiencies. Management performed an analysis and determined no premium deficiency existed as of December 31, 2022 and 2021.
Goodwill and Intangible Assets	Goodwill and Intangible Assets Goodwill and intangible assets are recorded as a result of a business combination. Goodwill represents the excess of the purchase price over the fair value of the assets acquired and liabilities assumed. The Company reviews its purchase price allocation up to one year subsequent to an acquisition and may make adjustments within the one-year period. The Company amortizes identifiable intangible assets with a finite useful life over the period that the intangible asset is expected to contribute directly or indirectly to its future cash flows; however, it does not amortize indefinite lived intangible assets. The Company evaluates goodwill and identifiable intangible assets for recoverability annually in the fourth quarter or on an interim basis should events or changes in circumstances indicate that a carrying amount may not be recoverable. To test for impairment, a qualitative assessment is performed to determine if it is more likely-than-not that the fair value of a reporting unit is less than its carrying value, including goodwill. This initial assessment includes, among other factors, consideration of: (i) past, current and projected future earnings and equity; (ii) recent trends and market conditions; and (iii) valuation metrics involving similar companies that are publicly traded and acquisitions of similar companies, if available. If the more likely-than-not threshold is met, a quantitative impairment test is performed by comparing the estimated fair value with the carrying value. If the carrying value of the net assets associated with the reporting unit exceeds the fair value of the reporting unit, goodwill is considered impaired and will be determined as the amount by which the reporting unit’s carrying value exceeds its fair value, not to exceed the carrying amount of goodwill. The Company’s reporting unit is at the underwriting division level; this is one level below the consolidated group where the underwriting division represents a business and discrete financial information is available and reviewed regularly by underwriting management. Determining the fair value of its reporting units is subjective in nature and involves the use of significant estimates and assumptions, including projected net cash flows, discount and long-term growth rates. The Company determines the fair value of its reporting units based on an income approach and market approach, whereby the fair value of the reporting unit is derived from the present value of estimated future cash flows associated with the reporting unit. The assumptions about estimated cash flows include factors such as future premiums, loss and LAE expenses, general and administrative expenses and industry trends. The Company considers historical rates and current market conditions when determining the discount and long-term growth rates to use in its analysis. The Company considers other valuation methods if the facts and circumstances indicate these methods provide a more representative approximation of fair value. Changes in these estimates based on evolving economic conditions or business strategies could result in material impairment charges in future periods. The Company bases its fair value estimates on assumptions it believes to be reasonable. Actual results may differ from those estimates. The following table presents goodwill impairment charges for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Goodwill impairment $ — $ 2,821 Goodwill impairment is included under “impairment charges” in the Consolidated Statements of Operations and Comprehensive (Loss) Income.
Property and Equipment	Property and Equipment Property and equipment, which is included in other assets on the consolidated balance sheets, is recorded at cost less accumulated depreciation. Depreciation expense is recognized on a straight-line basis for financial statement purposes over periods ranging from three
Leases	Leases Right-of-use (ROU) assets are included in other assets and lease liabilities are included in accounts payable and accrued liabilities on the balance sheet. For operating leases, the Company determines if a contract contains a lease at inception and recognizes the operating lease ROU assets and lease liabilities based on the present value of the future minimum lease payments at the commencement date. As the Company does not have the interest rate implicit in its leases, it uses its incremental borrowing rate based on the information available at the commencement date in determining the present value of future payments. Lease agreements may include options to extend or terminate. The options are exercised at the Company’s discretion and are included in operating lease liabilities if it is reasonably certain the option will be exercised. Lease agreements have lease and non-lease components, which are accounted for as a single lease component. Operating lease cost for future minimum lease payments is recognized on a straight-line basis over the lease term. Sublease income is recognized on a straight-line basis over the sublease term.
Reserves for losses and loss adjustment expenses	Reserves for losses and loss adjustment expenses Reserves for losses and loss adjustment expenses (“LAE”) represent the Company’s best estimate of the ultimate net cost of all reported and unreported losses that are unpaid as of the balance sheet dates. Its estimated reserves for losses and LAE include the accumulation of estimates for claims reported and unpaid prior to the balance sheet dates, estimates (based on projections of relevant historical data) of increases in claims costs for claims already reported, of claims incurred but not reported, and estimates of expenses for investigating and adjusting all incurred and unpaid claims. The Company estimates its reserves on an undiscounted basis, using individual case-basis valuations, statistical analyses, and various actuarial methods such as: Paid Loss Development — Historical payment patterns for prior claims are used to estimate future payment patterns for claims. These patterns are applied to current payments by policy year to yield an expected ultimate loss. Incurred Loss Development — Historical case loss patterns for past claims are used to estimate future case-incurred amounts for current claims. These patterns are applied to current case losses by policy year to yield an expected ultimate loss. Case Reserve Development — Patterns of historical development in reported losses relative to historical case reserves are determined. These patterns are applied to current case reserves by policy year and the result is combined with paid losses to yield an expected ultimate loss. Expected Loss Ratio — Historical loss ratios, in combination with projections of frequency and severity trends, as well as estimates of price and exposure changes, are analyzed to produce an estimate of the expected loss ratio (“loss pick”) for each policy year. The loss pick is then applied to the earned premium for each year to estimate the expected ultimate losses. Paid and Incurred Bornhuetter/Ferguson (BF) — This approach blends the expected loss ratio method with either the paid or incurred loss development method. In effect, the BF methods produce weighted average indications for each policy year. In most cases, multiple estimation methods will be valid for the particular facts and circumstances of the claim liabilities being evaluated. Each estimation method has its own set of assumption variables and its own advantages and disadvantages, with no single estimation method being better than the others in all situations, and no one set of assumption variables being meaningful for all underwriting divisions. The relative strengths and weaknesses of the particular estimation methods, when applied to a particular group of claims, can also change over time. Therefore, the weight given to each estimation method will likely change by policy year and with each evaluation given the facts and circumstances associated with each underwriting division. The estimates generated by the methods above are based on the Company’s historical information, industry information, and its estimates of future trends in variable factors such as loss severity and loss frequency. Reserves for losses and LAE are subject to uncertainty from various sources, including changes in reporting patterns, claims settlement patterns, judicial decisions, legislation, and economic conditions. Therefore, the Company’s actual loss experience may not conform to the methods used in determining the estimated amounts for such liability at the balance sheet dates. The Company continually monitors, and reviews reserves and adjusts its estimates as necessary as new information becomes available. Reserves for losses and LAE are subject to uncertainty from various sources, including changes in reporting patterns, claims settlement patterns, judicial decisions, legislation, and economic conditions. Therefore, the Company’s actual loss experience may not conform to the assumptions used in determining the estimated amounts for such liability at the balance sheet dates. The Company continually monitors and reviews reserves, and as settlements are made or reserves adjusted, the differences are reported in the current year.
Premiums	Premiums The Company earns and recognizes property and casualty and surety premiums on a pro-rata basis over the terms of the policies. The Company earns accident and health premiums as billed, based on census data. Gross premiums written are reduced by ceded premiums from proportional, facultative and excess of loss reinsurance costs for prospective reinsurance. Its premiums receivable includes deferred premiums, which represent installment payments the Company is due from insureds under the payment terms of their policies. The following table presents recorded allowance for estimated uncollectible premiums receivable for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Allowance for doubtful accounts $ 629 $ 261 Unearned premiums represent the portion of gross premiums written which is applicable to the unexpired terms of insurance policies or reinsurance contracts in force. Ceded unearned premiums represent the portion of ceded premiums written which is applicable to the unexpired terms of insurance policies or reinsurance contracts in force. These unearned premiums are calculated on a pro-rata basis over the terms of the policies for direct and ceded amounts.
Commission and Fee Income	Commission and Fee Income SUA commission revenue SUA commission revenue is generated from the placement of insurance policies on reinsurance programs through a reinsurance broker which represents the Company’s single performance obligation. Its transaction price is fixed at contract inception and based on a percentage of premiums placed. The Company recognizes 100% of the transaction price as the associated performance obligation is satisfied at the point in time a policy is placed as it has no constraints on revenue. SUA fee income SUA fee income is generated from the placement of insurance policies with a third-party insurance company. The Company’s single performance obligation consists of the placement of the policy. Its transaction price is variable at contract inception and based on a percentage of premium based on risk factors that vary every month such as employee
Income Taxes	Income Taxes Income tax expense is accrued for the tax effects of transactions reported on the consolidated financial statements, and this provision for income taxes consists of taxes currently due plus deferred taxes resulting from temporary differences between amounts reported for financial statement and income tax purposes. A valuation allowance is established for any deferred tax asset not expected to be realized. Deferred tax assets and liabilities are measured using enacted tax rates expected to apply to taxable income in the years in which temporary differences are expected to be recovered or settled. The effect on deferred tax assets and liabilities from a change in tax rates is recognized in income in the period that includes the enactment date. A liability for uncertain tax positions is recorded where it is more likely-than-not that the tax position will not be sustained upon examination by the appropriate tax authority. Changes in the liability for uncertain tax positions are reflected in income tax expense in the period when a new uncertain tax position arises, judgment changes about the likelihood of an uncertainty, the tax issue is settled, or the statute of limitation expires. Any potential net interest income or expense and penalties related to uncertain tax positions are recorded on the Consolidated Statements of Operations. The Company files a consolidated federal income tax return in the United States and certain other state tax returns. Its admitted insurance subsidiaries pay premium taxes on gross written premiums in lieu of most state income or franchise taxes. Premium tax expense is recognized within underwriting, acquisition and insurance expense on the Consolidated Statement of Operations.
Fair Value of Financial Instruments	Fair Value of Financial Instruments Fair value is estimated for each class of financial instrument based on the framework established in the fair value accounting guidance. This guidance requires an entity to maximize the use of observable inputs and minimize the use of unobservable inputs when measuring fair value. Fair value hierarchy disclosures are based on the quality of inputs used to measure fair value. The hierarchy gives the highest priority to unadjusted quoted prices in active markets for identical assets or liabilities (Level 1 measurements) and the lowest priority to unobservable inputs (Level 3 measurements). As a part of management’s process to determine fair value, the Company utilizes widely recognized, third-party pricing sources to determine the Company’s fair values of financial instruments. The Company has obtained an understanding of the third-party pricing sources’ valuation methodologies and inputs.
Stock Based Compensation	Stock Based Compensation The Company granted common stock to its employees and non-employee directors under the Stock Purchase Program and Equity Incentive Program (the “Legacy Programs”). The Legacy Programs required that employees who receive an award purchase a certain amount of stock, which the Company then matched. The matching share awards were subject to certain vesting requirements. For the purchased portion of the participant’s stock, the participant was required to make a minimum payment toward the purchase commitment, with the remainder of the balance issued as a note receivable to us and recorded as a stock notes receivable within Stockholders’ Equity. Compensation costs are recognized over the applicable vesting period for share-based payments to employees, former employees, and non-employee directors at fair value of the common stock on the grant date. The fair value of the common stock on the grant date was determined using an income approach and market approach. Forfeiture of purchased and awarded shares are recognized as they occur. In December 2020, the Compensation Committee of the Company’s Board of Directors (the “Compensation Committee”) approved a new Long Term Incentive Plan (the “2021 Plan”). The 2021 Plan provides for the granting of restricted stock, restricted stock units, performance share awards, as well as cash-based performance awards, to select employees and non-employee directors of the Company. Under the 2021 Plan, the Compensation Committee ratifies the selection of participants for each year’s grants which are subject to the terms and conditions of the 2021 Plan. The equity awards consist of common share awards with either a market or a performance condition and restricted common stock and common stock units. All awards are subject to a service condition and the accounting policy for each award is presented below. Market condition awards For common share awards with a market and service condition, the Company uses a probability assessment to determine the fair value of these awards on the grant date. It recognizes grant date fair value as compensation costs over the applicable service period of the award. If the market condition is not obtained, previously recognized compensation expense is not reversed. Performance and service condition awards For common share awards with a performance condition and a service condition, the Company calculates a grant date fair value based on the probability weighted assessment of the performance condition and respective award values. It recognizes compensation costs over the service period based on its latest estimate of grant date fair value. If the performance condition is not satisfied, the Company will reverse previously recognized compensation expense. Service condition awards The Company grants restricted common stock units that only have a service condition. It recognizes compensation costs over the service period based on the fair value of common stock on the grant date.
Earnings Per Share	Earnings Per Share Basic earnings per share is calculated using the two-class method. Undistributed earnings are allocated to participating securities based on the extent to which each class may share in earnings as if all the earnings for the period have been distributed. Basic earnings per share is calculated by dividing net income attributable to common shareholders by the weighted-average number of common shares outstanding for the period. Common shares related to its Legacy Programs are excluded from the weighted-average number of common shares outstanding for the period for basic earnings per share when contingencies, such as vesting requirements, exist and have not been satisfied. Contingently issuable common shares and common share equivalents are instruments where the holder must return, all or part of, if specified conditions are not met. These instruments are excluded from basic and diluted earnings per share when the specified conditions are not met presuming the end of the period is the end of the contingency period. Instruments that are convertible into common shares are included in diluted weighted-average common shares outstanding on an if-converted basis based on the legal conversion rate for the respective period, if dilutive. Share-based awards to employees with only service conditions are included as potential common shares, weighted for the portion of the period they are unvested, if dilutive. Share-based awards to employees with performance and service or market conditions are included as potential common shares presuming the end of the period is the end of the contingency period, if dilutive. When inclusion of common share adjustments increases the earnings per share or reduces the loss per share, the effect on earnings is anti-dilutive, and the diluted net earnings or net loss per share is computed excluding these common share equivalents.
Recent Accounting Standards Not Yet Adopted	Recent Accounting Standards Not Yet Adopted In June 2016, the FASB issued ASU 2016-13, Measurement of Credit Losses on Financial Instruments (Topic 326). ASU 2016-13 requires organizations to estimate credit losses on certain types of financial instruments, including receivables and available-for-sale debt securities, by introducing an approach based on expected losses. The expected loss approach will require entities to incorporate considerations of historical information, current information, and reasonable and supportable forecasts. The guidance is effective for fiscal years beginning after December 15, 2022. The Company will adopt this ASU effective January 1, 2023 using the modified retrospective app roach. The Company expects to recognize an increase in the allowance for uncollectible reinsurance of approximately $2.3 million an d an increase, net of tax, in accumulated deficit of approximately $2.3 million.

Summary of Significant Accoun_3

Summary of Significant Accounting Policies (Tables)	12 Months Ended
	Dec. 31, 2022
Accounting Policies [Abstract]
Reinsurance Retention	The following table presents reinsurance collateral for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Reinsurance collateral $ 253,870 $ 230,908
Reinsurance Recoverable, Credit Quality Indicator	The following table lists the individual reinsurers which represent 10% or more of the Company’s reinsurance recoverable balances and the respective financial strength rating from A.M. Best at December 31, 2022 and 2021: A.M. Best 2022 2021 Everest Reinsurance Co A+ 28.2 % 28.9 % Randall & Quilter (R&Q Bermuda (SAC) Ltd) Not rated Below 10 % 12.0 %
Schedule of Goodwill	The following table presents goodwill impairment charges for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Goodwill impairment $ — $ 2,821 The carrying amount and changes in the balance of goodwill by reporting unit is as follows: ($ in thousands) Accident Surety Energy Other Total Goodwill Gross balance at December 31, 2021 $ 91,577 $ 6,781 $ 10,052 $ 4,031 $ 112,441 Accumulated impairment at December 31, 2021 (44,821) — — (1,886) (46,707) Net balance at December 31, 2022 $ 46,756 $ 6,781 $ 10,052 $ 2,145 $ 65,734 ($ in thousands) Accident Surety Energy Exterminator Other Total Goodwill Gross balance at December 31, 2020 $ 91,577 $ — $ 10,052 $ 11,810 $ 4,681 $ 118,120 Accumulated impairment at December 31, 2020 (44,821) — — (9,248) — (54,069) Additions — 6,956 — — — 6,956 Disposals — (175) — (1,680) (650) (2,505) Impairment — — — (882) (1,886) (2,768) Net balance at December 31, 2021 $ 46,756 $ 6,781 $ 10,052 $ — $ 2,145 $ 65,734
Premium Receivable, Allowance for Credit Loss	The following table presents recorded allowance for estimated uncollectible premiums receivable for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Allowance for doubtful accounts $ 629 $ 261

Goodwill and Intangible Assets

Goodwill and Intangible Assets (Tables)	12 Months Ended
	Dec. 31, 2022
Goodwill and Intangible Assets Disclosure [Abstract]
Schedule of Goodwill	The following table presents goodwill impairment charges for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Goodwill impairment $ — $ 2,821 The carrying amount and changes in the balance of goodwill by reporting unit is as follows: ($ in thousands) Accident Surety Energy Other Total Goodwill Gross balance at December 31, 2021 $ 91,577 $ 6,781 $ 10,052 $ 4,031 $ 112,441 Accumulated impairment at December 31, 2021 (44,821) — — (1,886) (46,707) Net balance at December 31, 2022 $ 46,756 $ 6,781 $ 10,052 $ 2,145 $ 65,734 ($ in thousands) Accident Surety Energy Exterminator Other Total Goodwill Gross balance at December 31, 2020 $ 91,577 $ — $ 10,052 $ 11,810 $ 4,681 $ 118,120 Accumulated impairment at December 31, 2020 (44,821) — — (9,248) — (54,069) Additions — 6,956 — — — 6,956 Disposals — (175) — (1,680) (650) (2,505) Impairment — — — (882) (1,886) (2,768) Net balance at December 31, 2021 $ 46,756 $ 6,781 $ 10,052 $ — $ 2,145 $ 65,734
Schedule of Intangible Assets and Goodwill	The carrying amount and changes in the balance of other intangible assets are as follows: ($ in thousands) Agent Non-competes Trademarks Licenses Total Other Intangible Assets Gross balance at December 31, 2021 $ 24,558 $ 1,117 $ 999 $ 14,019 $ 40,693 Accumulated amortization at December 31, 2021 (14,421) (670) — — (15,091) Amortization (1,243) (223) — — (1,466) Net balance at December 31, 2022 $ 8,894 $ 224 $ 999 $ 14,019 $ 24,136 ($ in thousands) Agent Non-competes Trademarks Licenses Total Other Intangible Assets Gross balance at December 31, 2020 $ 16,355 $ 1,117 $ 1,122 $ 15,019 $ 33,613 Accumulated amortization at December 31, 2020 (13,203) (447) — — (13,650) Additions 8,300 — — — 8,300 Disposals (45) — (123) (1,000) (1,168) Impairment (52) — — — (52) Amortization (1,218) (223) — — (1,441) Net balance at December 31, 2021 $ 10,137 $ 447 $ 999 $ 14,019 $ 25,602
Finite-Lived Intangible Assets Amortization Expense	The Company’s recognized amortization expense for the years ended December 31, 2022 and 2021 is as follows: ($ in thousands) 2022 2021 Amortization expense $ 1,466 $ 1,441
Schedule of Finite-Lived Intangible Assets, Future Amortization Expense	Estimated future net amortization expense of intangible assets for the next five years is as follows: Years Ending December 31, Amount (in thousands) 2023 $ 1,466 2024 1,074 2025 998 2026 553 2027 553

Investments (Tables)

Investments (Tables)	12 Months Ended
	Dec. 31, 2022
Investments, Debt and Equity Securities [Abstract]
Debt Securities, Trading, and Equity Securities, FV-NI	The amortized cost and the fair value of the Company’s investments are summarized as follows: ($ in thousands) Gross Gross Gross Fair Value December 31, 2022 Fixed maturity securities, available for sale: U.S. government securities $ 50,416 $ 1 $ (1,876) $ 48,541 Corporate securities and miscellaneous 255,116 767 (20,754) 235,129 Municipal securities 65,836 24 (8,133) 57,727 Residential mortgage-backed securities 134,844 218 (15,206) 119,856 Commercial mortgage-backed securities 40,129 50 (3,684) 36,495 Asset-backed securities 116,275 91 (6,542) 109,824 Total fixed maturity securities, available for sale $ 662,616 $ 1,151 $ (56,195) $ 607,572 Fixed maturity securities, held to maturity: Asset-backed securities $ 52,467 $ — $ (5,696) $ 46,771 Total fixed maturity securities, held to maturity $ 52,467 $ — $ (5,696) $ 46,771 Equity securities: Common stocks $ 50,484 $ 10,015 $ (4,503) $ 55,996 Preferred stocks 11,798 15 (3,042) 8,771 Mutual funds 53,968 3,171 (1,737) 55,402 Total equity securities $ 116,250 $ 13,201 $ (9,282) $ 120,169 ($ in thousands) Gross Gross Gross Fair Value December 31, 2021 Fixed maturity securities, available for sale: U.S. government securities $ 48,816 $ 716 $ (269) $ 49,263 Corporate securities and miscellaneous 151,053 3,698 (588) 154,163 Municipal securities 53,179 3,799 (36) 56,942 Residential mortgage-backed securities 103,758 1,232 (1,255) 103,735 Commercial mortgage-backed securities 14,634 38 (188) 14,484 Asset-backed securities 81,038 226 (1,500) 79,764 Total fixed maturity securities, available for sale $ 452,478 $ 9,709 $ (3,836) $ 458,351 Fixed maturity securities, held to maturity: Asset-backed securities $ 47,117 $ — $ — $ 47,117 Total fixed maturity securities, held to maturity $ 47,117 $ — $ — $ 47,117 Equity securities: Common stocks $ 47,379 $ 13,887 $ (2,841) $ 58,425 Preferred stocks 17,821 349 (4) 18,166 Mutual funds 33,786 7,611 (17) 41,380 Total equity securities $ 98,986 $ 21,847 $ (2,862) $ 117,971
Investments Classified by Contractual Maturity Date	The amortized cost and estimated fair value of fixed maturity securities, available for sale, at December 31, 2022 by contractual maturity are shown below (in thousands). Expected maturities may differ from contractual maturities because borrowers have the right to call or prepay obligations with or without call or prepayment penalties. Also, changing interest rates, tax considerations or other factors may result in portfolio sales prior to maturity. ($ in thousands) Amortized Fair Value Due in less than one year $ 16,474 $ 16,215 Due after one year through five years 203,569 191,576 Due after five years through ten years 102,114 90,631 Due after ten years 49,211 42,975 Mortgage-backed securities 174,973 156,351 Asset-backed securities 116,275 109,824 Total $ 662,616 $ 607,572
Debt Securities, Available-for-Sale, Unrealized Loss Position, Fair Value	The following tables summarize gross unrealized losses and the corresponding fair values of investments, aggregated by length of time that individual securities have been in a continuous unrealized loss position: Less than 12 Months 12 Months or More Total ($ in thousands) Fair Value Gross Fair Value Gross Fair Value Gross December 31, 2022 Fixed maturity securities, available-for-sale: U.S. government securities $ 28,966 $ (603) $ 18,577 $ (1,273) $ 47,543 $ (1,876) Corporate securities and miscellaneous 171,506 (16,063) 34,283 (4,691) 205,789 (20,754) Municipal securities 51,701 (7,236) 3,689 (897) 55,390 (8,133) Residential mortgage-backed securities 56,246 (4,152) 52,778 (11,054) 109,024 (15,206) Commercial mortgage-backed securities 25,836 (1,488) 8,583 (2,196) 34,419 (3,684) Asset-backed securities 74,684 (3,351) 25,820 (3,191) 100,504 (6,542) Total fixed maturity securities, available-for-sale 408,939 (32,893) 143,730 (23,302) 552,669 (56,195) Fixed maturity securities, held-to-maturity: Asset-backed securities 46,771 (5,696) — — 46,771 (5,696) Total fixed maturity securities, held-to-maturity 46,771 (5,696) — — 46,771 (5,696) Total $ 455,710 $ (38,589) $ 143,730 $ (23,302) $ 599,440 $ (61,891) Less than 12 Months 12 Months or More Total ($ in thousands) Fair Value Gross Fair Value Gross Fair Value Gross December 31, 2021 Fixed maturity securities, available-for-sale: U.S. government securities $ 19,819 $ (267) $ 108 $ (2) $ 19,927 $ (269) Corporate securities and miscellaneous 47,308 (588) — — 47,308 (588) Municipal securities 4,549 (36) — — 4,549 (36) Residential mortgage-backed securities 72,672 (1,252) 145 (3) 72,817 (1,255) Commercial mortgage-backed securities 12,653 (175) 241 (12) 12,894 (187) Asset-backed securities 34,266 (1,463) 1,256 (38) 35,522 (1,501) Total fixed maturity securities, available-for-sale $ 191,267 $ (3,781) $ 1,750 $ (55) $ 193,017 $ (3,836)
Gain (Loss) on Securities	The components of net realized (losses) gains at December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Gross realized gains Fixed maturity securities, available-for sale $ 313 $ 474 Equity securities 3,865 2,763 Other 36 13 Total 4,214 3,250 Gross realized losses Fixed maturity securities, available-for sale (958) (1,160) Equity securities (3,827) (230) Other (76) (4) Total (4,861) (1,394) Net unrealized (losses) gains on securities still held Equity securities (15,058) 15,251 Net investment (losses) gains $ (15,705) $ 17,107
Investment Income	Proceeds from sales of debt and equity securities at December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Fixed maturity securities, available-for sale $ 13,964 $ 15,142 Equity securities 37,177 37,952 The Company’s net investment income for the years ended December 31, 2022 and 2021 is summarized as follows: ($ in thousands) 2022 2021 Income: Fixed maturity securities, available-for sale $ 18,481 $ 9,931 Fixed maturity securities, held-to-maturity 5,375 4,840 Equity securities 3,579 2,572 Equity method investments 6,015 9,280 Mortgage loans 4,767 1,188 Indirect loans 4,846 1,852 Short-term investments and cash 1,523 141 Other (102) 241 Total investment income 44,484 30,045 Investment expenses (7,553) (5,399) Net investment income $ 36,931 $ 24,646 The Company’s gross investment income for the years ended December 31, 2022 and 2021 is as follows: Years Ended December 31, ($ in thousands) 2022 2021 Retail $ 1,255 $ 66 Commercial 1,242 151 Industrial 565 90 Multi-family 909 143 Office 385 64 Land — 451 Hospitality 411 223 $ 4,767 $ 1,188
Schedule of Accumulated Other Comprehensive Income (Loss)	The change in net unrealized losses on investments, net of deferred income taxes, in other comprehensive loss for the years ended December 31, 2022 and 2021 is as follows: ($ in thousands) 2022 2021 Fixed maturity securities $ (60,918) $ (9,674) Deferred income taxes 12,793 2,098 Other comprehensive loss $ (48,125) $ (7,576)

Fair Value Measurements (Tables

Fair Value Measurements (Tables)	12 Months Ended
	Dec. 31, 2022
Fair Value Disclosures [Abstract]
Fair Value, by Balance Sheet Grouping	The following table presents the carrying value and estimated fair value of the Company’s financial instruments at December 31, 2022 and 2021: 2022 2021 ($ in thousands) Carrying Fair Carrying Fair Assets Fixed maturity securities, available-for-sale $ 607,572 $ 607,572 $ 458,351 $ 458,351 Fixed maturity securities, held-to-maturity 52,467 46,771 47,117 47,117 Equity securities 120,169 120,169 117,971 117,971 Mortgage loans 51,859 52,842 29,531 29,264 Short-term investments 121,158 121,158 164,278 164,278 Cash and cash equivalents 45,438 45,438 42,107 42,107 Restricted cash 79,573 79,573 65,167 65,167 Liabilities Notes payable $ 50,000 $ 50,000 $ 50,000 $ 50,000 Subordinated debt 78,609 78,728 78,529 83,235
Schedule of Fair Value, Assets and Liabilities Measured on Recurring Basis	The following table summarizes fair value measurements by level within the fair value hierarchy for assets and liabilities with a disclosed fair value: December 31, 2022 ($ in thousands) Level 1 Level 2 Level 3 Total Assets: Fixed maturity securities, available-for-sale: U.S. government securities $ 48,541 $ — $ — $ 48,541 Corporate securities and miscellaneous — 235,129 — 235,129 Municipal securities — 57,727 — 57,727 Residential mortgage-backed securities — 119,856 — 119,856 Commercial mortgage-backed securities — 36,495 — 36,495 Asset-backed securities — 109,824 — 109,824 Total fixed maturity securities, available-for-sale 48,541 559,031 — 607,572 Fixed maturity securities, held-to-maturity: Asset-backed securities — — 46,771 46,771 Total fixed maturity securities, held-to-maturity — — 46,771 46,771 Common stocks: Consumer discretionary 1,948 — — 1,948 Consumer staples 12,036 — — 12,036 Energy 3,241 — — 3,241 Finance 22,636 — — 22,636 Industrial 9,452 — — 9,452 Information technology 2,284 — — 2,284 Materials 2,820 — — 2,820 Other 1,579 — — 1,579 Total common stocks 55,996 — — 55,996 Preferred stocks: Consumer staples — 117 — 117 Finance — 7,085 — 7,085 Industrial — 1,020 — 1,020 Other — 549 — 549 Total preferred stocks — 8,771 — 8,771 Mutual funds: Fixed income 5,068 — — 5,068 Equity 49,773 — — 49,773 Commodity 561 — — 561 Total mutual funds 55,402 — — 55,402 Total equity securities 111,398 8,771 — 120,169 Mortgage loans — — 52,842 52,842 Short-term investments 121,158 — — 121,158 Total assets measured at fair value $ 281,097 $ 567,802 $ 99,613 $ 948,512 Liabilities: Notes payable $ — $ 50,000 $ — $ 50,000 Subordinated debt — 78,728 — 78,728 December 31, 2021 ($ in thousands) Level 1 Level 2 Level 3 Total Assets: Fixed maturity securities, available-for-sale: U.S. government securities $ 49,263 $ — $ — $ 49,263 Corporate securities and miscellaneous — 154,163 — 154,163 Municipal securities — 56,942 — 56,942 Residential mortgage-backed securities — 103,735 — 103,735 Commercial mortgage-backed securities — 14,484 — 14,484 Asset-backed securities — 79,764 — 79,764 Total fixed maturity securities, available-for-sale 49,263 409,088 — 458,351 Fixed maturity securities, held-to-maturity: Asset-backed securities — — 47,117 47,117 Total fixed maturity securities, held-to-maturity — — 47,117 47,117 Common stocks: Consumer discretionary 2,102 — — 2,102 Consumer staples 13,643 — — 13,643 Energy 2,781 — — 2,781 Finance 24,657 — — 24,657 Industrial 8,806 — — 8,806 Information technology 2,408 — — 2,408 Materials 3,160 — — 3,160 Other 868 — — 868 Total common stocks 58,425 — — 58,425 Preferred stocks: Finance — 17,018 — 17,018 Other — 1,148 — 1,148 Total preferred stocks — 18,166 — 18,166 Mutual funds: Fixed income 5,374 — — 5,374 Equity 35,471 — — 35,471 Commodity 535 — — 535 Total mutual funds 41,380 — — 41,380 Total equity securities 99,805 18,166 — 117,971 Mortgage loans — — 29,264 29,264 Short-term investments 164,278 — — 164,278 Total assets measured at fair value $ 313,346 $ 427,254 $ 76,381 $ 816,981 Liabilities: Notes payable $ — $ 50,000 $ — $ 50,000 Subordinated debt — 83,235 — 83,235

Mortgage Loans (Tables)

Mortgage Loans (Tables)	12 Months Ended
	Dec. 31, 2022
Receivables [Abstract]
Schedule of Accounts, Notes, Loans and Financing Receivable	The carrying value of the Company’s mortgage loans for the years ended December 31, 2022 and 2021 is as follows: ($ in thousands) 2022 2021 Retail $ 16,516 $ 10,593 Commercial 15,309 6,298 Industrial 6,329 6,314 Multi-family 5,593 3,296 Office 3,197 1,691 Hospitality 4,915 1,339 $ 51,859 $ 29,531
Investment Income	Proceeds from sales of debt and equity securities at December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Fixed maturity securities, available-for sale $ 13,964 $ 15,142 Equity securities 37,177 37,952 The Company’s net investment income for the years ended December 31, 2022 and 2021 is summarized as follows: ($ in thousands) 2022 2021 Income: Fixed maturity securities, available-for sale $ 18,481 $ 9,931 Fixed maturity securities, held-to-maturity 5,375 4,840 Equity securities 3,579 2,572 Equity method investments 6,015 9,280 Mortgage loans 4,767 1,188 Indirect loans 4,846 1,852 Short-term investments and cash 1,523 141 Other (102) 241 Total investment income 44,484 30,045 Investment expenses (7,553) (5,399) Net investment income $ 36,931 $ 24,646 The Company’s gross investment income for the years ended December 31, 2022 and 2021 is as follows: Years Ended December 31, ($ in thousands) 2022 2021 Retail $ 1,255 $ 66 Commercial 1,242 151 Industrial 565 90 Multi-family 909 143 Office 385 64 Land — 451 Hospitality 411 223 $ 4,767 $ 1,188

Other Long-Term Investments (Ta

Other Long-Term Investments (Tables)	12 Months Ended
	Dec. 31, 2022
Equity Method Investments and Joint Ventures [Abstract]
Carrying Value of Equity Method Investments	The carrying value of equity method investments at December 31, 2022 and 2021 is as follows: ($ in thousands) 2022 2021 Arena SOP LP units $ 8,734 $ 5,692 Arena Special Opportunities Fund, LP units 44,504 41,763 Brewer Lane Ventures Fund II LP units 200 — Dowling Capital Partners LP units 1,965 2,416 Hudson Ventures Fund 2 LP units 3,551 1,913 JVM Funds LLC units 22,473 24,000 RISCOM 4,037 3,366 Universa Black Swan LP units 1,325 4,354 $ 86,789 $ 83,504 Net investment income from equity method investments at December 31, 2022 and 2021 is summarized as follows: ($ in thousands) 2022 2021 Arena SOP LP units $ 3,042 $ 4,717 Arena Special Opportunities Fund, LP units 3,719 3,729 Dowling Capital Partners LP units 502 438 Hudson Ventures Fund 2 LP units 379 (16) JVM Funds LLC (70) — RISCOM 1,471 1,058 Universa Black Swan LP units (3,028) (646) $ 6,015 $ 9,280 The unfunded commitment of equity method investments at December 31, 2022 and 2021 is as follows: ($ in thousands) 2022 2021 Brewer Lane Ventures Fund II LP units $ 4,800 $ — Dowling Capital Partners LP units 386 368 Hudson Ventures Fund 2 LP units 1,796 3,063 $ 6,982 $ 3,431 The following table summarizes the Company’s recorded investment in RISCOM compared to its share of underlying equity for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Investment in RISCOM: Underlying equity $ 2,292 $ 1,378 Difference 1,745 1,988 Recorded investment balance $ 4,037 $ 3,366 The following table summarizes the Company’s recorded investment in JVM Funds LLC compared to its share of underlying equity for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Investment in JVM Funds LLC: Underlying equity $ 21,565 $ 24,000 Difference 908 — Recorded investment balance $ 22,473 $ 24,000 As of December 31, 2022 and 2021, the Company held indirect investments in collateralized loans and loan collateral through SMA1 and SMA2. The carrying value and unfunded commitment of the SMA1 and SMA2 for the years ended December 31, 2022 and 2021 are as follows: 2022 2021 ($ in thousands) Carrying Unfunded Carrying Unfunded SMA1 $ 36,426 $ — $ 33,100 $ — SMA2 2,010 — 10,855 16,563 Investment in indirect loans and loan collateral $ 38,436 $ — $ 43,955 $ 16,563

Property and Equipment (Tables)

Property and Equipment (Tables)	12 Months Ended
	Dec. 31, 2022
Property, Plant and Equipment [Abstract]
Property, Plant and Equipment	The following table presents the components of property and equipment for the years ended December 31, 2022 and 2021, which are included within other assets on the consolidated balance sheets. ($ in thousands) 2022 2021 Leasehold improvements $ 2,670 $ 2,761 Equipment 7,230 7,477 Software 25,964 23,314 Other 39 39 35,903 33,591 Accumulated depreciation (27,229) (23,964) Total $ 8,674 $ 9,627 The following table presents recorded depreciation expense at December 31, 2022 and 2021: ($ in thousands) 2022 2021 Depreciation expense $ 3,582 $ 3,636

Leases (Tables)

Leases (Tables)	12 Months Ended
	Dec. 31, 2022
Leases [Abstract]
Lease, Cost	The following tables provide information regarding the Company’s leases for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Operating lease right-of-use assets $ 8,214 $ 10,532 Operating lease liabilities 8,616 10,921 Operating lease weighted-average remaining lease term 5.00 years 5.73 years Operating lease weighted-average discount rate 3.16 % 3.12 % ($ in thousands) 2022 2021 Operating lease expense $ 2,414 $ 2,607 Short-term lease expense 220 127 Total lease expense $ 2,634 $ 2,734 Operating cash outflows from operating leases $ 2,382 $ 2,361
Lessee, Operating Lease, Liability, Maturity	The following table sets forth the future minimum lease payment obligations of the Company’s operating leases at December 31, 2022: ($ in thousands) 2022 2023 $ 2,206 2024 1,996 2025 1,465 2026 1,227 2027 1,116 Thereafter 1,189 Total future minimum operating lease payments $ 9,199 Less imputed interest (583) Total operating lease liability $ 8,616

Subordinated Debt (Tables)

Subordinated Debt (Tables)	12 Months Ended
	Dec. 31, 2022
Debt Disclosure [Abstract]
Summary of Subordinated Debt	The following table summarizes the Company’s subordinated debt for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Junior subordinated interest debentures, due September 15, 2036, payable quarterly Principal $ 59,794 $ 59,794 Less: Debt issuance costs (657) (705) Unsecured subordinated notes, due May 24, 2039, interest payable quarterly Principal 20,000 20,000 Less: Debt issuance costs (528) (560) Subordinated debt, net of debt issuance costs $ 78,609 $ 78,529

Notes_Payable (Tables)

Notes Payable (Tables)	12 Months Ended
	Dec. 31, 2022
Debt Disclosure [Abstract]
Summary of Notes Payable	The following table summarizes the Company’s notes payable for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Term loan, due December 31, 2024, interest payable quarterly $ 50,000 $ 50,000 Interest payments on the term loan at December 31, 2022 and 2021 were as follows: ($ in thousands) 2022 2021 Interest payments on term loan $ 1,443 $ 894 Interest payments on the Company’s revolving line of credit at December 31, 2022 and 2021 were as follows: ($ in thousands) 2022 2021 Interest payments on revolving line of credit $ — $ 127

Stockholders_ Equity (Tables)

Stockholders’ Equity (Tables)	12 Months Ended
	Dec. 31, 2022
Equity [Abstract]
Schedule of Stock by Class	The following table presents Preferred Shares that could be converted to common shares after the final adjustment to the Option Conversion Rate at December 31, 2022: 2022 Preferred shares outstanding 1,969,660 Common shares upon conversion of preferred shares 16,305,113

Income Taxes (Tables)

Income Taxes (Tables)	12 Months Ended
	Dec. 31, 2022
Income Tax Disclosure [Abstract]
Schedule of Components of Income Tax Expense (Benefit)	Income tax (benefit) expense for the years ended December 31, 2022 and 2021 consisted of the following: ($ in thousands) 2022 2021 Current income tax expense $ 120 $ — Deferred tax expense related to temporary differences 10,267 9,992 Total income tax expense $ 10,387 $ 9,992
Schedule of Effective Income Tax Rate Reconciliation	The differences between income taxes expected at the federal statutory income tax rate of 21% and the reported income tax expense for the years ended December 31, 2022 and 2021 are summarized as follows: 2022 2021 ($ in thousands) Amount Percentage Amount Percentage Income tax expense at federal statutory rate $ 10,454 21.0 % $ 10,145 21.0 % Tax advantaged investments (324) (0.7) (256) (0.5) Other 257 0.6 103 0.2 Total income tax expense $ 10,387 20.9 % $ 9,992 20.7 %
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 at both December 31, 2022 and 2021 are presented below: ($ in thousands) 2022 2021 Deferred tax assets: Net operating losses $ 14,966 $ 28,009 Losses and loss adjustment expenses 10,748 7,782 Unearned premiums 11,959 9,461 Intangibles 607 1,632 Capital loss carryover 1,321 — Unrealized losses on investments 11,563 — Stock options/awards 1,107 627 Other 3,369 1,034 Total deferred tax assets 55,640 48,545 Less valuation allowance (586) (586) Total deferred tax assets after valuation allowance 55,054 47,959 Deferred tax liabilities: Deferred policy acquisition costs 8,209 6,063 Depreciation 1,481 1,459 Investments 7,144 5,507 Unrealized gains on investments — 1,230 Other 2,032 37 Total deferred tax liabilities 18,866 14,296 Deferred income taxes $ 36,188 $ 33,663
Summary of Valuation Allowance	The Company provides a valuation allowance against deferred tax assets when it is more likely-than-not that some portion, or all, of deferred tax assets will not be realized. Its deferred tax valuation allowance for the years ended December 31, 2022 and 2021 is as follows: ($ in thousands) 2022 2021 Balance at beginning of year $ 586 $ 586 Balance at end of year $ 586 $ 586

Reserves for Losses and Loss _2

Reserves for Losses and Loss Adjustment Expenses (Tables)	12 Months Ended
	Dec. 31, 2022
Insurance [Abstract]
Schedule of Liability for Unpaid Claims and Claims Adjustment Expense	The reconciliation of unpaid losses and loss adjustment expenses as reported in the consolidated balance sheets for the years ended December 31, 2022 and 2021 is as follows: ($ in thousands) 2022 2021 Reserves for losses and LAE, beginning of period $ 979,549 $ 856,780 Less: reinsurance recoverable on unpaid claims, beginning of period (381,338) (375,178) Reserves for losses and LAE, beginning of period, net of reinsurance 598,211 481,602 Incurred, net of reinsurance, related to: Current period 393,939 338,348 Prior years 14,385 28,000 Total incurred, net of reinsurance 408,324 366,348 Paid, net of reinsurance, related to: Current period 105,928 77,551 Prior years 194,836 172,188 Total paid 300,764 249,739 Net reserves for losses and LAE, end of period 705,771 598,211 Plus: reinsurance recoverable on unpaid claims, end of period 435,986 381,338 Reserves for losses and LAE, end of period $ 1,141,757 $ 979,549 The following table presents the impact of the LPT on the consolidated statements of operations for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Strengthening of reserves subject to the LPT $ (14,385) $ (28,000) Reinsurance recoveries under the LPT 5,813 11,937 Pretax net impact of the LPT and strengthening of reserves subject to the LPT $ (8,572) $ (16,063)
Schedule of Short-Duration Insurance Contracts	Short Tail/Monoline Specialty — includes specialty/monoline business — Global Property, A&H, Surety, Professional Lines underwriting divisions Incurred Losses and ALAE, Net of Reinsurance ($ in thousands) As of December 31, 2022 Years Ended December 31, Reported Claims Accident Year 2018* 2019* 2020* 2021* 2022 IBNR 2018 $ 33,570 $ 33,570 $ 33,570 $ 36,863 $ 34,363 $ 559 858 2019 62,922 48,101 45,301 48,800 230 1,015 2020 66,359 64,859 64,859 6,614 1,258 2021 100,172 100,172 25,018 1,428 2022 123,342 80,974 1,282 Total $ 371,536 Cumulative net paid loss and LAE from the table below (218,145) Net reserves for loss and LAE before 2018 5,512 Total net reserves for loss and LAE $ 158,903 *Data presented for these calendar years is required supplementary information, which is unaudited. Cumulative Paid Losses and ALAE, Net of Reinsurance ($ in thousands) Years Ended December 31, Accident Year 2018* 2019* 2020* 2021* 2022 2018 $ 24,754 $ 31,907 $ 31,323 $ 33,522 $ 33,446 2019 33,714 40,228 41,484 45,031 2020 30,974 56,499 70,684 2021 14,754 49,526 2022 19,458 Total $ 218,145 *Data presented for these calendar years is required supplementary information, which is unaudited. Multi-line Solutions — mid to longer tail lines of business, includes the Company’s industry solutions, programs, captives and transactional E&S underwriting divisions Incurred Losses and ALAE, Net of Reinsurance ($ in thousands) As of December 31, 2022 Accident Years Ended December 31, Reported Claims 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 IBNR 2013 $ 66,517 $ 71,800 $ 64,439 $ 73,382 $ 75,196 $ 74,701 $ 74,987 $ 75,419 $ 69,496 $ 69,515 $ 1,994 3,324 2014 100,355 100,355 115,749 116,970 116,970 117,783 118,995 120,697 120,777 946 4,977 2015 103,191 114,266 117,024 117,024 119,216 121,746 122,839 122,902 2,446 5,364 2016 63,223 62,843 62,843 62,643 69,701 73,200 73,318 1,523 4,691 2017 65,332 65,332 64,260 72,913 78,578 78,762 4,331 5,515 2018 74,476 74,476 73,868 73,868 74,209 10,202 5,041 2019 107,432 106,432 106,432 110,896 1,487 6,021 2020 140,880 140,880 134,124 27,390 5,393 2021 173,568 169,566 60,497 6,486 2022 223,447 105,571 7,330 Total $ 1,177,516 Cumulative net paid loss and LAE from the table below (821,766) Net reserves for loss and LAE before 2013 4,945 Total net reserves for loss and LAE $ 360,695 *Data presented for these calendar years is required supplementary information, which is unaudited. Cumulative Paid Losses and ALAE, Net of Reinsurance ($ in thousands) Years Ended December 31, Accident 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 2013 $ 19,912 $ 40,425 $ 48,673 $ 59,460 $ 67,857 $ 73,511 $ 75,117 $ 75,340 $ 75,030 $ 74,178 2014 32,530 63,699 81,251 96,639 101,984 104,984 105,756 106,214 104,076 2015 44,152 72,137 88,833 99,401 108,291 114,098 117,295 118,166 2016 23,239 42,528 53,352 58,895 60,864 63,893 71,565 2017 23,770 41,945 53,093 64,235 67,243 69,096 2018 26,201 42,568 50,320 64,119 70,080 2019 33,019 59,529 78,803 96,601 2020 33,538 67,216 83,533 2021 39,388 78,923 2022 55,548 Total $ 821,766 *Data presented for these calendar years is required supplementary information, which is unaudited. Exited Lines — all lines in runoff Incurred Losses and ALAE, Net of Reinsurance ($ in thousands) As of December 31, 2022 Years Ended December 31, Reported Claims Accident 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 IBNR 2013 $ 44,791 $ 37,993 $ 44,909 $ 46,437 $ 48,372 $ 48,372 $ 49,850 $ 49,486 $ 53,236 $ 54,130 $ 2,031 2,640 2014 64,186 57,904 62,425 63,729 63,729 68,855 69,920 71,219 71,761 11,475 4,149 2015 61,810 65,063 68,008 70,803 75,187 80,678 83,365 84,058 1,779 4,550 2016 93,526 92,743 91,119 93,324 103,602 104,612 105,852 5,975 4,858 2017 75,919 80,341 82,545 95,119 97,011 98,646 33,630 4,309 2018 73,492 68,125 78,902 90,348 96,685 335 4,864 2019 87,115 90,598 92,118 106,594 2,487 5,549 2020 83,900 86,700 86,700 5,196 4,719 2021 49,957 46,146 33,733 2,265 2022 31,487 9,336 185 Total $ 782,059 Cumulative net paid loss and LAE from the table below (612,456) Net reserves for loss and LAE before 2013 8,890 Total net reserves for loss and LAE $ 178,493 *Data presented for these calendar years is required supplementary information, which is unaudited. Cumulative Paid Losses and ALAE, Net of Reinsurance ($ in thousands) Years Ended December 31, Accident 2013* 2014* 2015* 2016* 2017* 2018* 2019* 2020* 2021* 2022 2013 $ 4,763 $ 17,904 $ 36,890 $ 42,995 $ 41,158 $ 44,186 $ 47,101 $ 48,069 $ 48,322 $ 49,605 2014 9,700 30,863 42,141 50,785 49,906 52,450 53,290 53,615 55,737 2015 9,026 41,653 55,610 65,269 73,100 77,981 80,312 81,789 2016 36,592 57,638 70,253 78,070 81,516 85,794 87,966 2017 34,177 52,103 51,985 56,839 63,516 68,434 2018 25,552 60,149 67,262 80,448 90,791 2019 28,636 63,243 66,682 82,878 2020 24,468 54,950 63,468 2021 9,856 15,449 2022 16,339 Total $ 612,456 *Data presented for these calendar years is required supplementary information, which is unaudited.
Reconciliation of Claims Development to Liability	The table below presents the reconciliation of the net incurred and paid claims development to loss reserves in the consolidated balance sheets at December 31, 2022 by sub-category: ($ in thousands) 2022 Net reserves for losses and LAE: Short Tail/Monoline Specialty $ 158,903 Multi-line Solutions 360,695 Exited Lines 178,493 Reserves for losses and LAE, net of reinsurance 698,091 Reinsurance recoverable on unpaid claims: Short Tail/Monoline Specialty 147,435 Multi-line Solutions 252,673 Exited Lines 35,878 Total reinsurance recoverable on unpaid claims 435,986 Unallocated LAE 7,680 Reserves for losses and LAE at end of year $ 1,141,757
Schedule of Historical Claims Duration	The following table presents supplementary information about average historical claims duration as of December 31, 2022, by sub-category is as follows: Average Annual Percentage Payout of Incurred Claims by Age, Net of Reinsurance Years Years 1 2 3 4 5 6 7 8 9 10 Short Tail/Monoline Specialty 56.0 % 24.0 % 10.1 % 6.2 % 2.9 % 0.1 % — % 0.6 % 0.1 % — % Multi-line Solutions 40.7 % 26.1 % 14.9 % 8.1 % 5.1 % 3.6 % 1.2 % — % 0.2 % 0.1 % Exited Lines 43.4 % 26.7 % 12.7 % 8.6 % 4.5 % 1.7 % 1.1 % 0.9 % 0.4 % — %

Premiums (Tables)

Premiums (Tables)	12 Months Ended
	Dec. 31, 2022
Insurance [Abstract]
Schedule of Premiums Written	Direct and assumed premiums written by line of business pursuant to statutory accounting guidelines for the years ended December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Property $ 279,384 24.4 % $ 235,686 25.1 % Commercial Auto Liability $ 243,300 21.3 % $ 227,853 24.2 % General Liability $ 140,557 12.3 % $ 116,953 12.4 % Group Accident & Health $ 130,808 11.4 % $ 112,146 11.9 % Professional Liability $ 90,418 7.9 % $ 61,466 6.5 % Excess Liability $ 79,922 7.0 % $ 52,176 5.6 % Surety $ 79,062 6.9 % $ 51,792 5.6 % Workers’ Compensation $ 51,790 4.5 % $ 41,890 4.5 % Commercial Auto Physical Damage $ 48,711 4.3 % $ 39,897 4.2 % Total $ 1,143,952 100.0 % $ 939,859 100.0 % The effects of reinsurance on premiums written and earned at December 31, 2022 and 2021 are as follows: 2022 2021 ($ in thousands) Written Earned Written Earned Direct premiums $ 1,012,239 $ 951,121 $ 842,318 $ 816,837 Assumed premiums 131,713 113,610 97,541 102,352 Ceded premiums (468,409) (448,737) (410,716) (419,366) Net premiums $ 675,543 $ 615,994 $ 529,143 $ 499,823 Ceded losses and LAE incurred $ 311,257 $ 248,360

Commission and Fee Income (Tabl

Commission and Fee Income (Tables)	12 Months Ended
	Dec. 31, 2022
Revenue from Contract with Customer [Abstract]
Disaggregation of Revenue	The Company’s disaggregated revenues from contracts with customers for the years ended December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 SUA commission revenue $ 3,224 $ 2,037 SUA fee income 1,597 1,185 Other 378 751 Total commission and fee income $ 5,199 $ 3,973
Schedule of Contract Asset	The Company’s contract assets from commission and fee income for the years ended December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Contract asset $ 1,292 $ 1,209

Underwriting, Acquisition and_2

Underwriting, Acquisition and Insurance Expenses (Tables)	12 Months Ended
	Dec. 31, 2022
Other Income and Expenses [Abstract]
Schedule of Underwriting, Acquisition and Insurance Expenses	The Company’s underwriting, acquisition and insurance expenses at December 31, 2022 and 2021 consisted of the following: ($ in thousands) 2022 2021 Amortization of policy acquisition costs $ 65,695 $ 47,061 Other operating and general expenses 116,476 91,437 Total underwriting, acquisition and insurance expenses $ 182,171 $ 138,498

Reinsurance (Tables)

Reinsurance (Tables)	12 Months Ended
	Dec. 31, 2022
Insurance [Abstract]
Effects of Reinsurance	Direct and assumed premiums written by line of business pursuant to statutory accounting guidelines for the years ended December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Property $ 279,384 24.4 % $ 235,686 25.1 % Commercial Auto Liability $ 243,300 21.3 % $ 227,853 24.2 % General Liability $ 140,557 12.3 % $ 116,953 12.4 % Group Accident & Health $ 130,808 11.4 % $ 112,146 11.9 % Professional Liability $ 90,418 7.9 % $ 61,466 6.5 % Excess Liability $ 79,922 7.0 % $ 52,176 5.6 % Surety $ 79,062 6.9 % $ 51,792 5.6 % Workers’ Compensation $ 51,790 4.5 % $ 41,890 4.5 % Commercial Auto Physical Damage $ 48,711 4.3 % $ 39,897 4.2 % Total $ 1,143,952 100.0 % $ 939,859 100.0 % The effects of reinsurance on premiums written and earned at December 31, 2022 and 2021 are as follows: 2022 2021 ($ in thousands) Written Earned Written Earned Direct premiums $ 1,012,239 $ 951,121 $ 842,318 $ 816,837 Assumed premiums 131,713 113,610 97,541 102,352 Ceded premiums (468,409) (448,737) (410,716) (419,366) Net premiums $ 675,543 $ 615,994 $ 529,143 $ 499,823 Ceded losses and LAE incurred $ 311,257 $ 248,360
Ceded Credit Risk	The components of reinsurance recoverables and ceded unearned premium at December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Unpaid losses and loss adjustment expenses ceded $ 435,986 $ 381,338 Paid losses and loss adjustment expense ceded 107,228 90,761 Loss portfolio transfer 38,145 64,228 Reinsurance recoverables $ 581,359 $ 536,327 Ceded unearned premium $ 157,645 $ 137,973
Schedule of Liability for Unpaid Claims and Claims Adjustment Expense	The reconciliation of unpaid losses and loss adjustment expenses as reported in the consolidated balance sheets for the years ended December 31, 2022 and 2021 is as follows: ($ in thousands) 2022 2021 Reserves for losses and LAE, beginning of period $ 979,549 $ 856,780 Less: reinsurance recoverable on unpaid claims, beginning of period (381,338) (375,178) Reserves for losses and LAE, beginning of period, net of reinsurance 598,211 481,602 Incurred, net of reinsurance, related to: Current period 393,939 338,348 Prior years 14,385 28,000 Total incurred, net of reinsurance 408,324 366,348 Paid, net of reinsurance, related to: Current period 105,928 77,551 Prior years 194,836 172,188 Total paid 300,764 249,739 Net reserves for losses and LAE, end of period 705,771 598,211 Plus: reinsurance recoverable on unpaid claims, end of period 435,986 381,338 Reserves for losses and LAE, end of period $ 1,141,757 $ 979,549 The following table presents the impact of the LPT on the consolidated statements of operations for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Strengthening of reserves subject to the LPT $ (14,385) $ (28,000) Reinsurance recoveries under the LPT 5,813 11,937 Pretax net impact of the LPT and strengthening of reserves subject to the LPT $ (8,572) $ (16,063)
Schedule of Deposit Assets	The following table presents the Company’s deposit assets for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Deposit asset $ 41,801 $ 45,003

Stock Based Compensation (Table

Stock Based Compensation (Tables)	12 Months Ended
	Dec. 31, 2022
Share-Based Payment Arrangement [Abstract]
Schedule of Common Stock Notes Receivable	The following table presents common stock notes receivable related to Legacy Programs at both December 31, 2022 and 2021: ($ in thousands) 2022 2021 Common stock notes receivable $ 512 $ 1,630
Summary of Equity Awards	A summary of the equity awards, target payout ranges based on meeting award conditions and authorized target common shares is as follows: Award Requisite Authorized Target Year ended December 31, 2022 Market condition awards 0% — 150% 3 years 28,495 Performance condition awards 0% — 150% 3 years 26,210 Restricted share and stock unit awards N/A 1 to 3 years 144,137 198,842 Year ended December 31, 2021 Market condition awards 0% — 150% 3 years 46,474 Performance condition awards 0% — 150% 3 years 29,501 Restricted stock unit awards N/A 3 years 141,420 217,395
Schedule of Nonvested Share Activity	A summary of the status of the Company’s non-vested common stock awards from the Legacy Programs and the 2021 Plan is presented below: Weighted-Average Number of Common Shares Non-vested at January 1, 2022 $ 13.23 375,643 Granted 14.17 198,842 Vested 15.16 (144,042) Forfeited 12.51 (10,547) Non-vested at December 31, 2022 $ 12.55 419,896 Non-vested at January 1, 2021 $ 19.47 84,671 Granted 11.95 332,658 Vested 14.20 (6,514) Forfeited 16.01 (35,172) Non-vested at December 31, 2021 $ 13.23 375,643
Schedule of Share-Based Compensation Expense	Stock-based compensation expense for the years ended December 31, 2022 and 2021 is summarized as follows: ($ in thousands) 2022 2021 Stock-based compensation expense Stock-based compensation expense $ 2,325 $ 1,365 Forfeitures (38) (843) Total $ 2,287 $ 522

Earnings Per Share (Tables)

Earnings Per Share (Tables)	12 Months Ended
	Dec. 31, 2022
Earnings Per Share [Abstract]
Schedule of Earnings Per Share, Basic and Diluted	The following table presents a reconciliation of the numerator and denominator of the basic and diluted earnings per share computations contained in the consolidated financial statements for the years ended December 31, 2022 and 2021. ($ in thousands, except for share and per share amounts) 2022 2021 Numerator Net income $ 39,396 $ 38,317 Less: Undistributed income allocated to participating securities (18,879) (18,507) Net income attributable to common shareholders (numerator for basic earnings per share) 20,517 19,810 Add back: Undistributed income allocated to participating securities 18,879 18,507 Net income (numerator for diluted earnings per share under the two-class method) $ 39,396 $ 38,317 Denominator Basic weighted-average common shares 16,568,393 16,308,712 Preferred shares (if converted method) 15,245,533 15,235,568 Contingently issuable instruments (treasury stock method) 519,080 723,146 Market condition awards (contingently issuable) 94,936 67,598 Performance awards (contingently issuable) 39,148 — Restricted stock units (treasury stock method) 186,104 133,024 Diluted weighted-average common share equivalents 32,653,194 32,468,048 Basic earnings per share $ 1.24 $ 1.21 Diluted earnings per share $ 1.21 $ 1.18
Schedule of Antidilutive Securities Excluded from Computation of Earnings Per Share	The following table presents instruments that were excluded from the calculation of diluted weighted-average common share equivalents at both December 31, 2022 and 2021. 2022 2021 Contingently issuable instruments (treasury stock method) 60,576 — The following table presents common share equivalents of contingently issuable instruments that were excluded from basic earnings per share in shares for the years ended December 31, 2022 and 2021: 2022 2021 Common shares 22,919 192,609 Preferred shares, if converted 1,059,602 1,235,420 Total 1,082,521 1,428,029

Employee Benefit Plans (Tables)

Employee Benefit Plans (Tables)	12 Months Ended
	Dec. 31, 2022
Retirement Benefits [Abstract]
Schedule of Company's Matching Contributions	The following table presents the Company’s expensed matching contributions for the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 401(k) matching contributions $ 2,389 $ 2,288

Related Party Transactions (Tab

Related Party Transactions (Tables)	12 Months Ended
	Dec. 31, 2022
Related Party Transactions [Abstract]
Schedule of Unrealized Gain (Loss) on Investments	The unrealized loss on this investment for the years ended December 31, 2022 and 2021 is as follows: ($ in thousands) 2022 2021 Unrealized losses on investment in Westaim $ (2,283) $ (1,971)
Schedule of Related Party Transactions	Pursuant to the current Management Services Agreement, at December 31, 2022 and 2021, the Company incurred the following expenses related to services provided by Westaim: ($ in thousands) 2022 2021 Management services agreement $ 500 $ 500 Net earned premium and gross written commissions related to these agreements at December 31, 2022 and 2021 is summarized as follows: ($ in thousands) 2022 2021 Net earned premium $ 91,051 $ 76,701 Gross written commissions 23,472 21,256 Premiums receivable from RISCOM at December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Premiums receivable $ 9,940 $ 11,334 Reinsurance The Company has reinsurance agreements with Everest Re, an affiliate of Mt. Whitney Securities, LLC, a limited partner of Westaim HIIG LP and holder of Preferred Shares. Reinsurance premiums ceded related to the agreement at December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Reinsurance premiums ceded $ 59,592 $ 101,154 Reinsurance recoverable from Everest Re, net of premium payables for the years ended December 31, 2022 and 2021 are as follows: ($ in thousands) 2022 2021 Reinsurance recoverable, net of premium payables $ 177,455 $ 168,847 The following table reflects advisory and professional services fees and expense reimbursements paid to various affiliated shareholders and directors during the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Professional fees and reimbursements $ 3,387 $ 3,669

Commitment and Contingencies (T

Commitment and Contingencies (Tables)	12 Months Ended
	Dec. 31, 2022
Commitments and Contingencies Disclosure [Abstract]
Other Commitments	The following table presents earn-out payments to former owners during the years ended December 31, 2022 and 2021: ($ in thousands) 2022 2021 Earn-out payments to former owners $ — $ 554

Regulatory Matters (Tables)

Regulatory Matters (Tables)	12 Months Ended
	Dec. 31, 2022
Insurance [Abstract]
Schedule of Compliance with Regulatory Capital Requirements under Banking Regulations	The capital and surplus and RBC level of HSIC on a consolidated statutory basis (including IIC, GMIC OSIC, and BIC) for the years ended December 31, 2022 and 2021 were as follows: ($ in thousands) 2022 2021 Statutory capital and surplus $ 408,167 $ 369,583 RBC authorized control level 110,635 84,968

Statutory Accounting Principl_2

Statutory Accounting Principles (Tables)	12 Months Ended
	Dec. 31, 2022
Insurance [Abstract]
Statutory Accounting Principles	The statutory capital and surplus for the Company’s principal operating subsidiaries for the years ended December 31, 2022 and 2021 was as follows: ($ in thousands) 2022 2021 HSIC $ 408,167 $ 369,583 IIC 272,413 215,508 GMIC 259,311 209,347 OSIC 21,270 21,095 These amounts include ownership interests in affiliated insurance subsidiaries. The statutory net income (loss) for the Company’s principal operating subsidiaries for the years ended December 31, 2022 and 2021 was as follows: ($ in thousands) 2022 2021 HSIC $ 10,860 $ 5,880 IIC 25,394 7,315 GMIC 14,091 (947) BIC — (67) OSIC 173 31

Nature of Operations (Details)

Nature of Operations (Details)	12 Months Ended
	Dec. 31, 2022 segment
Organization, Consolidation and Presentation of Financial Statements [Abstract]
Number of operating segments	1

Summary of Significant Accoun_4

Summary of Significant Accounting Policies - Reinsurance Retention (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Accounting Policies [Abstract]
Reinsurance collateral	$ 253,870	$ 230,908

Summary of Significant Accoun_5

Summary of Significant Accounting Policies - Reinsurance Recoverable, Credit Quality Indicator (Details) - Reinsurer concentration risk - Reinsurance recoverable including reinsurance premium paid	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Randall & Quilter (R&Q Bermuda (SAC) Ltd)
Concentration Risk [Line Items]
Concentration risk, percentage		12%
A+ | Everest Reinsurance Co
Concentration Risk [Line Items]
Concentration risk, percentage	28.20%	28.90%

Summary of Significant Accoun_6

Summary of Significant Accounting Policies - Goodwill Impairment (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Accounting Policies [Abstract]
Goodwill impairment	$ 0	$ 2,821	$ 2,768

Summary of Significant Accoun_7

Summary of Significant Accounting Policies - Property and Equipment (Details)	12 Months Ended
	Dec. 31, 2022
Minimum
Concentration Risk [Line Items]
Property, plant and equipment, useful life	3 years
Maximum
Concentration Risk [Line Items]
Property, plant and equipment, useful life	7 years

Summary of Significant Accoun_8

Summary of Significant Accounting Policies - Premium Receivable, Allowance for Credit Loss (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Accounting Policies [Abstract]
Allowance for doubtful accounts	$ 629	$ 261

Recent Accounting Pronounceme_2

Recent Accounting Pronouncements (Details) - USD ($) $ in Thousands	Jan. 01, 2023	Dec. 31, 2022	Dec. 31, 2021
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Accumulated deficit		$ (105,417)	$ (144,813)
Subsequent event | Period of adoption, adjustment | Pro forma
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Allowance for uncollectible reinsurance recoverable	$ 2,300
Accumulated deficit	$ 2,300

Goodwill and Intangible Asset_2

Goodwill and Intangible Assets - Narrative (Details) - USD ($) $ in Thousands	1 Months Ended		3 Months Ended	12 Months Ended
	Jun. 30, 2021	Jan. 31, 2021	Jun. 30, 2021	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Finite-Lived Intangible Assets [Line Items]
Purchase of business				$ 0	$ 10,554
Impairment				$ 0	2,821	$ 2,768
Useful life				14 years
Goodwill recognized				$ 65,734	65,734
Impairment					52
Net realized gain on sale of business				0	$ 5,077
Exterminator Pro
Finite-Lived Intangible Assets [Line Items]
Gain on disposition of assets		$ 3,500
Impairment		900
Book of Errors & Omissions Business
Finite-Lived Intangible Assets [Line Items]
Impairment			$ 1,900
Book of Errors & Omissions Business | Agent Relationships
Finite-Lived Intangible Assets [Line Items]
Impairment			$ 100
Boston Indemnity Company
Finite-Lived Intangible Assets [Line Items]
Net proceeds related to sale	$ 8,200
Net realized gain on sale of business	$ 1,800
Aegis Surety
Finite-Lived Intangible Assets [Line Items]
Purchase of business		10,000
Implied fair value of business		$ 15,300
Purchase price for intangible assets				$ 8,300
Useful life				15 years
Goodwill recognized				$ 6,900

Goodwill and Intangible Asset_3

Goodwill and Intangible Assets - Schedule of Goodwill (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Goodwill [Roll Forward]
Goodwill, gross balance		$ 112,441	$ 118,120
Accumulated impairment		(46,707)	(54,069)
Additions			6,956
Disposals			(2,505)
Impairment	$ 0	(2,821)	(2,768)
Goodwill, net balance	65,734	65,734
Accident and Health
Goodwill [Roll Forward]
Goodwill, gross balance		91,577	91,577
Accumulated impairment		(44,821)	(44,821)
Additions			0
Disposals			0
Impairment			0
Goodwill, net balance	46,756	46,756
Surety
Goodwill [Roll Forward]
Goodwill, gross balance		6,781	0
Accumulated impairment		0	0
Additions			6,956
Disposals			(175)
Impairment			0
Goodwill, net balance	6,781	6,781
Energy
Goodwill [Roll Forward]
Goodwill, gross balance		10,052	10,052
Accumulated impairment		0	0
Additions			0
Disposals			0
Impairment			0
Goodwill, net balance	10,052	10,052
Exterminator Pro
Goodwill [Roll Forward]
Goodwill, gross balance			11,810
Accumulated impairment			(9,248)
Additions			0
Disposals			(1,680)
Impairment			(882)
Goodwill, net balance		0
Other
Goodwill [Roll Forward]
Goodwill, gross balance		4,031	4,681
Accumulated impairment		(1,886)	0
Additions			0
Disposals			(650)
Impairment			$ (1,886)
Goodwill, net balance	$ 2,145	$ 2,145

Goodwill and Intangible Asset_4

Goodwill and Intangible Assets - Schedule of Intangible Assets and Goodwill (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Finite-Lived
Accumulated amortization		$ (15,091)	$ (13,650)
Amortization	$ (1,466)	$ (1,441)
Impairment Of Intangible Asset Finite Lived Statement Of Income Or Comprehensive Income Extensible Enumeration Not Disclosed Flag		Impairment
Total
Intangible assets, gross balance		$ 40,693	33,613
Accumulated amortization		(15,091)	(13,650)
Additions		8,300
Disposals		(1,168)
Impairment		(52)
Amortization	(1,466)	(1,441)
Gross intangible assets, ending balance	24,136	25,602
Trademarks
Indefinite-Lived
Beginning balance	999	1,122
Additions		0
Disposals		(123)
Impairment		0
Ending balance	999	999
Licenses
Indefinite-Lived
Beginning balance	14,019	15,019
Additions		0
Disposals		(1,000)
Impairment		0
Ending balance	14,019	14,019
Agent Relationships
Finite-Lived
Gross, beginning balance	24,558	16,355
Accumulated amortization		(14,421)	(13,203)
Additions		8,300
Disposals		(45)
Impairment		(52)
Amortization	(1,243)	(1,218)
Net, ending balance	8,894	10,137
Total
Accumulated amortization		(14,421)	(13,203)
Amortization	(1,243)	(1,218)
Non-competes
Finite-Lived
Gross, beginning balance	1,117	1,117
Accumulated amortization		(670)	(447)
Additions		0
Disposals		0
Impairment		0
Amortization	(223)	(223)
Net, ending balance	224	447
Total
Accumulated amortization		(670)	$ (447)
Amortization	$ (223)	$ (223)

Goodwill and Intangible Asset_5

Goodwill and Intangible Assets - Finite-Lived Intangible Assets Amortization Expense (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Goodwill and Intangible Assets Disclosure [Abstract]
Amortization expense	$ 1,466	$ 1,441

Goodwill and Intangible Asset_6

Goodwill and Intangible Assets - Schedule of Finite-Lived Intangible Assets, Future Amortization Expense (Details) $ in Thousands	Dec. 31, 2022 USD ($)
Years Ending December 31,
2023	$ 1,466
2024	1,074
2025	998
2026	553
2027	$ 553

Investments - Debt Securities,

Investments - Debt Securities, Trading, and Equity Securities, FV-NI (Details) - USD ($)	Dec. 31, 2022	Dec. 31, 2021
Total fixed maturity securities, available for sale
Gross Amortized Cost	$ 662,616,000	$ 452,478,000
Gross Unrealized Gains	1,151,000	9,709,000
Gross Unrealized Losses	(56,195,000)	(3,836,000)
Fixed maturity securities, available-for-sale:	607,572,000	458,351,000
Total fixed maturity securities, held to maturity
Gross Amortized Cost	52,467,000	47,117,000
Gross Unrealized Gains	0	0
Gross Unrealized Losses	(5,696,000)	0
Fixed maturity securities, held-to-maturity:	46,771,000	47,117,000
Total equity securities
Gross Amortized Cost	116,250,000	98,986,000
Gross Unrealized Gains	13,201,000	21,847,000
Gross Unrealized Losses	(9,282,000)	(2,862,000)
Equity securities, at fair value	120,169,000	117,971,000
U.S. government securities
Total fixed maturity securities, available for sale
Gross Amortized Cost	50,416,000	48,816,000
Gross Unrealized Gains	1,000	716,000
Gross Unrealized Losses	(1,876,000)	(269,000)
Fixed maturity securities, available-for-sale:	48,541,000	49,263,000
Corporate securities and miscellaneous
Total fixed maturity securities, available for sale
Gross Amortized Cost	255,116,000	151,053,000
Gross Unrealized Gains	767,000	3,698,000
Gross Unrealized Losses	(20,754,000)	(588,000)
Fixed maturity securities, available-for-sale:	235,129,000	154,163,000
Municipal securities
Total fixed maturity securities, available for sale
Gross Amortized Cost	65,836,000	53,179,000
Gross Unrealized Gains	24,000	3,799,000
Gross Unrealized Losses	(8,133,000)	(36,000)
Fixed maturity securities, available-for-sale:	57,727,000	56,942,000
Residential mortgage-backed securities
Total fixed maturity securities, available for sale
Gross Amortized Cost	134,844,000	103,758,000
Gross Unrealized Gains	218,000	1,232,000
Gross Unrealized Losses	(15,206,000)	(1,255,000)
Fixed maturity securities, available-for-sale:	119,856,000	103,735,000
Commercial mortgage-backed securities
Total fixed maturity securities, available for sale
Gross Amortized Cost	40,129,000	14,634,000
Gross Unrealized Gains	50,000	38,000
Gross Unrealized Losses	(3,684,000)	(188,000)
Fixed maturity securities, available-for-sale:	36,495,000	14,484,000
Asset-backed securities
Total fixed maturity securities, available for sale
Gross Amortized Cost	116,275,000	81,038,000
Gross Unrealized Gains	91,000	226,000
Gross Unrealized Losses	(6,542,000)	(1,500,000)
Fixed maturity securities, available-for-sale:	109,824,000	79,764,000
Total fixed maturity securities, held to maturity
Gross Amortized Cost	52,467,000	47,117,000
Gross Unrealized Gains	0	0
Gross Unrealized Losses	(5,696,000)	0
Fixed maturity securities, held-to-maturity:	46,771,000	47,117,000
Total common stocks
Total equity securities
Gross Amortized Cost	50,484,000	47,379,000
Gross Unrealized Gains	10,015,000	13,887,000
Gross Unrealized Losses	(4,503,000)	(2,841,000)
Equity securities, at fair value	55,996,000	58,425,000
Total preferred stocks
Total equity securities
Gross Amortized Cost	11,798,000	17,821,000
Gross Unrealized Gains	15,000	349,000
Gross Unrealized Losses	(3,042,000)	(4,000)
Equity securities, at fair value	8,771,000	18,166,000
Total mutual funds
Total equity securities
Gross Amortized Cost	53,968,000	33,786,000
Gross Unrealized Gains	3,171,000	7,611,000
Gross Unrealized Losses	(1,737,000)	(17,000)
Equity securities, at fair value	$ 55,402,000	$ 41,380,000

Investments - Investments Class

Investments - Investments Classified by Contractual Maturity Date (Details) - USD ($)	Dec. 31, 2022	Dec. 31, 2021
Amortized Cost
Due in less than one year	$ 16,474,000
Due after one year through five years	203,569,000
Due after five years through ten years	102,114,000
Due after ten years	49,211,000
Gross Amortized Cost	662,616,000	$ 452,478,000
Fair Value
Due in less than one year	16,215,000
Due after one year through five years	191,576,000
Due after five years through ten years	90,631,000
Due after ten years	42,975,000
Fair value total	607,572,000	458,351,000
Mortgage-backed securities
Amortized Cost
Without single maturity date	174,973,000
Fair Value
Without single maturity date	156,351,000
Asset-backed securities
Amortized Cost
Without single maturity date	116,275,000
Gross Amortized Cost	116,275,000	81,038,000
Fair Value
Without single maturity date	109,824,000
Fair value total	$ 109,824,000	$ 79,764,000

Investments - Schedule of Unrea

Investments - Schedule of Unrealized Loss on Investments (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Available for sale, fair value
Less than 12 Months	$ 408,939	$ 191,267
12 Months or More	143,730	1,750
Total	552,669	193,017
Available for sale, gross unrealized losses
Less than 12 Months	(32,893)	(3,781)
12 Months or More	(23,302)	(55)
Total	(56,195)	(3,836)
Held-to-maturity, fair value
Less than 12 Months	46,771
12 Months or More	0
Total	46,771
Held-to-maturity, gross unrealized losses
Less than 12 Months	(5,696)
12 Months or More	0
Total	(5,696)
Available-for-sale and held-to-maturity, fair value
Less than 12 Months	455,710
12 Months or More	143,730
Total	599,440
Available-for-sale and held-to-maturity, gross unrealized losses
Less than 12 Months	(38,589)
12 Months or More	(23,302)
Total	(61,891)
U.S. government securities
Available for sale, fair value
Less than 12 Months	28,966	19,819
12 Months or More	18,577	108
Total	47,543	19,927
Available for sale, gross unrealized losses
Less than 12 Months	(603)	(267)
12 Months or More	(1,273)	(2)
Total	(1,876)	(269)
Corporate securities and miscellaneous
Available for sale, fair value
Less than 12 Months	171,506	47,308
12 Months or More	34,283	0
Total	205,789	47,308
Available for sale, gross unrealized losses
Less than 12 Months	(16,063)	(588)
12 Months or More	(4,691)	0
Total	(20,754)	(588)
Municipal securities
Available for sale, fair value
Less than 12 Months	51,701	4,549
12 Months or More	3,689	0
Total	55,390	4,549
Available for sale, gross unrealized losses
Less than 12 Months	(7,236)	(36)
12 Months or More	(897)	0
Total	(8,133)	(36)
Residential mortgage-backed securities
Available for sale, fair value
Less than 12 Months	56,246	72,672
12 Months or More	52,778	145
Total	109,024	72,817
Available for sale, gross unrealized losses
Less than 12 Months	(4,152)	(1,252)
12 Months or More	(11,054)	(3)
Total	(15,206)	(1,255)
Commercial mortgage-backed securities
Available for sale, fair value
Less than 12 Months	25,836	12,653
12 Months or More	8,583	241
Total	34,419	12,894
Available for sale, gross unrealized losses
Less than 12 Months	(1,488)	(175)
12 Months or More	(2,196)	(12)
Total	(3,684)	(187)
Asset-backed securities
Available for sale, fair value
Less than 12 Months	74,684	34,266
12 Months or More	25,820	1,256
Total	100,504	35,522
Available for sale, gross unrealized losses
Less than 12 Months	(3,351)	(1,463)
12 Months or More	(3,191)	(38)
Total	(6,542)	$ (1,501)
Held-to-maturity, fair value
Less than 12 Months	46,771
12 Months or More	0
Total	46,771
Held-to-maturity, gross unrealized losses
Less than 12 Months	(5,696)
12 Months or More	0
Total	$ (5,696)

Investments - Narrative (Detail

Investments - Narrative (Details) $ in Millions	Dec. 31, 2022 USD ($) position	Dec. 31, 2021 USD ($)
Investments, Debt and Equity Securities [Abstract]
Unrealized loss position aged over 12 months, number of positions | position	111
Cash and securities segregated under federal and other regulations | $	$ 60.2	$ 63.2

Investments - Net Investment Lo

Investments - Net Investment Losses (Gains) (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Gross realized gains
Fixed maturity securities, available-for sale	$ 313	$ 474
Equity securities	3,865	2,763
Other	36	13
Total	4,214	3,250
Gross realized losses
Fixed maturity securities, available-for sale	(958)	(1,160)
Equity securities	(3,827)	(230)
Other	(76)	(4)
Total	(4,861)	(1,394)
Net unrealized (losses) gains on securities still held
Equity securities	(15,058)	15,251
Net investment (losses) gains	$ (15,705)	$ 17,107

Investments - Proceeds from Sal

Investments - Proceeds from Sales (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Investments, Debt and Equity Securities [Abstract]
Fixed maturity securities, available-for sale	$ 13,964	$ 15,142
Equity securities	$ 37,177	$ 37,952

Investments - Net Investment In

Investments - Net Investment Income (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Net Investment Income [Line Items]
Total investment income	$ 44,484	$ 30,045
Investment expenses	(7,553)	(5,399)
Net investment income	36,931	24,646
Fixed maturity securities, available-for sale
Net Investment Income [Line Items]
Total investment income	18,481	9,931
Fixed maturity securities, held-to-maturity
Net Investment Income [Line Items]
Total investment income	5,375	4,840
Equity securities:
Net Investment Income [Line Items]
Total investment income	3,579	2,572
Equity method investments
Net Investment Income [Line Items]
Total investment income	6,015	9,280
Mortgage loans
Net Investment Income [Line Items]
Total investment income	4,767	1,188
Indirect loans
Net Investment Income [Line Items]
Total investment income	4,846	1,852
Short-term investments and cash
Net Investment Income [Line Items]
Total investment income	1,523	141
Other
Net Investment Income [Line Items]
Total investment income	$ (102)	$ 241

Investments - Schedule of Accum

Investments - Schedule of Accumulated Other Comprehensive Income (Loss) (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Investments, Debt and Equity Securities [Abstract]
Fixed maturity securities	$ (60,918)	$ (9,674)
Deferred income taxes	12,793	2,098
Total other comprehensive loss	$ (48,125)	$ (7,576)

Fair Value Measurements - Fair

Fair Value Measurements - Fair Value, by Balance Sheet Grouping (Details) - USD ($)	Dec. 31, 2022	Dec. 31, 2021
Assets
Fixed maturity securities, available-for-sale:	$ 607,572,000	$ 458,351,000
Fixed maturity securities, held-to-maturity:	46,771,000	47,117,000
Equity securities, at fair value	120,169,000	117,971,000
Short-term investments	121,158,000	164,278,000
Liabilities
Notes payable	50,000,000	50,000,000
Subordinated debt	78,728,000	83,235,000
Carrying  Value
Assets
Fixed maturity securities, available-for-sale:	607,572,000	458,351,000
Fixed maturity securities, held-to-maturity:	52,467,000	47,117,000
Equity securities, at fair value	120,169,000	117,971,000
Mortgage loans	51,859,000	29,531,000
Short-term investments	121,158,000	164,278,000
Cash and cash equivalents	45,438,000	42,107,000
Restricted cash	79,573,000	65,167,000
Liabilities
Notes payable	50,000,000	50,000,000
Subordinated debt	78,609,000	78,529,000
Fair  Value
Assets
Fixed maturity securities, available-for-sale:	607,572,000	458,351,000
Fixed maturity securities, held-to-maturity:	46,771,000	47,117,000
Equity securities, at fair value	120,169,000	117,971,000
Mortgage loans	52,842,000	29,264,000
Short-term investments	121,158,000	164,278,000
Cash and cash equivalents	45,438,000	42,107,000
Restricted cash	79,573,000	65,167,000
Liabilities
Notes payable	50,000,000	50,000,000
Subordinated debt	$ 78,728,000	$ 83,235,000

Fair Value Measurements - Sched

Fair Value Measurements - Schedule of Fair Value, Assets and Liabilities Measured on Recurring Basis (Details) - USD ($)	Dec. 31, 2022	Dec. 31, 2021
Assets
Fixed maturity securities, available-for-sale:	$ 607,572,000	$ 458,351,000
Fixed maturity securities, held-to-maturity:	46,771,000	47,117,000
Equity securities, at fair value	120,169,000	117,971,000
Mortgage loans	52,842,000	29,264,000
Short-term investments	121,158,000	164,278,000
Total assets measured at fair value	948,512,000	816,981,000
Liabilities:
Notes payable	50,000,000	50,000,000
Subordinated debt	78,728,000	83,235,000
U.S. government securities
Assets
Fixed maturity securities, available-for-sale:	48,541,000	49,263,000
Corporate securities and miscellaneous
Assets
Fixed maturity securities, available-for-sale:	235,129,000	154,163,000
Municipal securities
Assets
Fixed maturity securities, available-for-sale:	57,727,000	56,942,000
Residential mortgage-backed securities
Assets
Fixed maturity securities, available-for-sale:	119,856,000	103,735,000
Commercial mortgage-backed securities
Assets
Fixed maturity securities, available-for-sale:	36,495,000	14,484,000
Asset-backed securities
Assets
Fixed maturity securities, available-for-sale:	109,824,000	79,764,000
Fixed maturity securities, held-to-maturity:	46,771,000	47,117,000
Total common stocks
Assets
Equity securities, at fair value	55,996,000	58,425,000
Total common stocks | Consumer discretionary
Assets
Equity securities, at fair value	1,948,000	2,102,000
Total common stocks | Consumer staples
Assets
Equity securities, at fair value	12,036,000	13,643,000
Total common stocks | Energy
Assets
Equity securities, at fair value	3,241,000	2,781,000
Total common stocks | Finance
Assets
Equity securities, at fair value	22,636,000	24,657,000
Total common stocks | Industrial
Assets
Equity securities, at fair value	9,452,000	8,806,000
Total common stocks | Information technology
Assets
Equity securities, at fair value	2,284,000	2,408,000
Total common stocks | Materials
Assets
Equity securities, at fair value	2,820,000	3,160,000
Total common stocks | Other
Assets
Equity securities, at fair value	1,579,000	868,000
Total preferred stocks
Assets
Equity securities, at fair value	8,771,000	18,166,000
Total preferred stocks | Consumer staples
Assets
Equity securities, at fair value	117,000
Total preferred stocks | Finance
Assets
Equity securities, at fair value	7,085,000	17,018,000
Total preferred stocks | Industrial
Assets
Equity securities, at fair value	1,020,000
Total preferred stocks | Other
Assets
Equity securities, at fair value	549,000	1,148,000
Total mutual funds
Assets
Equity securities, at fair value	55,402,000	41,380,000
Total mutual funds | Fixed income
Assets
Equity securities, at fair value	5,068,000	5,374,000
Total mutual funds | Equity
Assets
Equity securities, at fair value	49,773,000	35,471,000
Total mutual funds | Commodity
Assets
Equity securities, at fair value	561,000	535,000
Fair Value, Inputs, Level 1
Assets
Fixed maturity securities, available-for-sale:	48,541,000	49,263,000
Fixed maturity securities, held-to-maturity:	0	0
Equity securities, at fair value	111,398,000	99,805,000
Mortgage loans	0	0
Short-term investments	121,158,000	164,278,000
Total assets measured at fair value	281,097,000	313,346,000
Liabilities:
Notes payable	0	0
Subordinated debt	0	0
Fair Value, Inputs, Level 1 | U.S. government securities
Assets
Fixed maturity securities, available-for-sale:	48,541,000	49,263,000
Fair Value, Inputs, Level 1 | Corporate securities and miscellaneous
Assets
Fixed maturity securities, available-for-sale:	0	0
Fair Value, Inputs, Level 1 | Municipal securities
Assets
Fixed maturity securities, available-for-sale:	0	0
Fair Value, Inputs, Level 1 | Residential mortgage-backed securities
Assets
Fixed maturity securities, available-for-sale:	0	0
Fair Value, Inputs, Level 1 | Commercial mortgage-backed securities
Assets
Fixed maturity securities, available-for-sale:	0	0
Fair Value, Inputs, Level 1 | Asset-backed securities
Assets
Fixed maturity securities, available-for-sale:	0	0
Fixed maturity securities, held-to-maturity:	0	0
Fair Value, Inputs, Level 1 | Total common stocks
Assets
Equity securities, at fair value	55,996,000	58,425,000
Fair Value, Inputs, Level 1 | Total common stocks | Consumer discretionary
Assets
Equity securities, at fair value	1,948,000	2,102,000
Fair Value, Inputs, Level 1 | Total common stocks | Consumer staples
Assets
Equity securities, at fair value	12,036,000	13,643,000
Fair Value, Inputs, Level 1 | Total common stocks | Energy
Assets
Equity securities, at fair value	3,241,000	2,781,000
Fair Value, Inputs, Level 1 | Total common stocks | Finance
Assets
Equity securities, at fair value	22,636,000	24,657,000
Fair Value, Inputs, Level 1 | Total common stocks | Industrial
Assets
Equity securities, at fair value	9,452,000	8,806,000
Fair Value, Inputs, Level 1 | Total common stocks | Information technology
Assets
Equity securities, at fair value	2,284,000	2,408,000
Fair Value, Inputs, Level 1 | Total common stocks | Materials
Assets
Equity securities, at fair value	2,820,000	3,160,000
Fair Value, Inputs, Level 1 | Total common stocks | Other
Assets
Equity securities, at fair value	1,579,000	868,000
Fair Value, Inputs, Level 1 | Total preferred stocks
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 1 | Total preferred stocks | Consumer staples
Assets
Equity securities, at fair value	0
Fair Value, Inputs, Level 1 | Total preferred stocks | Finance
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 1 | Total preferred stocks | Industrial
Assets
Equity securities, at fair value	0
Fair Value, Inputs, Level 1 | Total preferred stocks | Other
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 1 | Total mutual funds
Assets
Equity securities, at fair value	55,402,000	41,380,000
Fair Value, Inputs, Level 1 | Total mutual funds | Fixed income
Assets
Equity securities, at fair value	5,068,000	5,374,000
Fair Value, Inputs, Level 1 | Total mutual funds | Equity
Assets
Equity securities, at fair value	49,773,000	35,471,000
Fair Value, Inputs, Level 1 | Total mutual funds | Commodity
Assets
Equity securities, at fair value	561,000	535,000
Fair Value, Inputs, Level 2
Assets
Fixed maturity securities, available-for-sale:	559,031,000	409,088,000
Fixed maturity securities, held-to-maturity:	0	0
Equity securities, at fair value	8,771,000	18,166,000
Mortgage loans	0	0
Short-term investments	0	0
Total assets measured at fair value	567,802,000	427,254,000
Liabilities:
Notes payable	50,000,000	50,000,000
Subordinated debt	78,728,000	83,235,000
Fair Value, Inputs, Level 2 | U.S. government securities
Assets
Fixed maturity securities, available-for-sale:	0	0
Fair Value, Inputs, Level 2 | Corporate securities and miscellaneous
Assets
Fixed maturity securities, available-for-sale:	235,129,000	154,163,000
Fair Value, Inputs, Level 2 | Municipal securities
Assets
Fixed maturity securities, available-for-sale:	57,727,000	56,942,000
Fair Value, Inputs, Level 2 | Residential mortgage-backed securities
Assets
Fixed maturity securities, available-for-sale:	119,856,000	103,735,000
Fair Value, Inputs, Level 2 | Commercial mortgage-backed securities
Assets
Fixed maturity securities, available-for-sale:	36,495,000	14,484,000
Fair Value, Inputs, Level 2 | Asset-backed securities
Assets
Fixed maturity securities, available-for-sale:	109,824,000	79,764,000
Fixed maturity securities, held-to-maturity:	0	0
Fair Value, Inputs, Level 2 | Total common stocks
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 2 | Total common stocks | Consumer discretionary
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 2 | Total common stocks | Consumer staples
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 2 | Total common stocks | Energy
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 2 | Total common stocks | Finance
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 2 | Total common stocks | Industrial
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 2 | Total common stocks | Information technology
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 2 | Total common stocks | Materials
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 2 | Total common stocks | Other
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 2 | Total preferred stocks
Assets
Equity securities, at fair value	8,771,000	18,166,000
Fair Value, Inputs, Level 2 | Total preferred stocks | Consumer staples
Assets
Equity securities, at fair value	117,000
Fair Value, Inputs, Level 2 | Total preferred stocks | Finance
Assets
Equity securities, at fair value	7,085,000	17,018,000
Fair Value, Inputs, Level 2 | Total preferred stocks | Industrial
Assets
Equity securities, at fair value	1,020,000
Fair Value, Inputs, Level 2 | Total preferred stocks | Other
Assets
Equity securities, at fair value	549,000	1,148,000
Fair Value, Inputs, Level 2 | Total mutual funds
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 2 | Total mutual funds | Fixed income
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 2 | Total mutual funds | Equity
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 2 | Total mutual funds | Commodity
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 3
Assets
Fixed maturity securities, available-for-sale:	0	0
Fixed maturity securities, held-to-maturity:	46,771,000	47,117,000
Equity securities, at fair value	0	0
Mortgage loans	52,842,000	29,264,000
Short-term investments	0	0
Total assets measured at fair value	99,613,000	76,381,000
Liabilities:
Notes payable	0	0
Subordinated debt	0	0
Fair Value, Inputs, Level 3 | U.S. government securities
Assets
Fixed maturity securities, available-for-sale:	0	0
Fair Value, Inputs, Level 3 | Corporate securities and miscellaneous
Assets
Fixed maturity securities, available-for-sale:	0	0
Fair Value, Inputs, Level 3 | Municipal securities
Assets
Fixed maturity securities, available-for-sale:	0	0
Fair Value, Inputs, Level 3 | Residential mortgage-backed securities
Assets
Fixed maturity securities, available-for-sale:	0	0
Fair Value, Inputs, Level 3 | Commercial mortgage-backed securities
Assets
Fixed maturity securities, available-for-sale:	0	0
Fair Value, Inputs, Level 3 | Asset-backed securities
Assets
Fixed maturity securities, available-for-sale:	0	0
Fixed maturity securities, held-to-maturity:	46,771,000	47,117,000
Fair Value, Inputs, Level 3 | Total common stocks
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 3 | Total common stocks | Consumer discretionary
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 3 | Total common stocks | Consumer staples
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 3 | Total common stocks | Energy
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 3 | Total common stocks | Finance
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 3 | Total common stocks | Industrial
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 3 | Total common stocks | Information technology
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 3 | Total common stocks | Materials
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 3 | Total common stocks | Other
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 3 | Total preferred stocks
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 3 | Total preferred stocks | Consumer staples
Assets
Equity securities, at fair value	0
Fair Value, Inputs, Level 3 | Total preferred stocks | Finance
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 3 | Total preferred stocks | Industrial
Assets
Equity securities, at fair value	0
Fair Value, Inputs, Level 3 | Total preferred stocks | Other
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 3 | Total mutual funds
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 3 | Total mutual funds | Fixed income
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 3 | Total mutual funds | Equity
Assets
Equity securities, at fair value	0	0
Fair Value, Inputs, Level 3 | Total mutual funds | Commodity
Assets
Equity securities, at fair value	$ 0	$ 0

Mortgage Loans - Narrative (Det

Mortgage Loans - Narrative (Details) - USD ($) $ in Millions	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Accounts, Notes, Loans and Financing Receivable [Line Items]
Mortgage loans in foreclosure	$ 6.4	$ 10.8
Minimum
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans held-for-investment, term	1 year
Percentage of property appraisal value	40%
Maximum
Accounts, Notes, Loans and Financing Receivable [Line Items]
Loans held-for-investment, term	2 years
Percentage of property appraisal value	90%

Mortgage Loans - Portfolios (De

Mortgage Loans - Portfolios (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Accounts, Notes, Loans and Financing Receivable [Line Items]
Mortgage loans	$ 51,859	$ 29,531
Mortgage loans
Accounts, Notes, Loans and Financing Receivable [Line Items]
Total investment income	4,767	1,188
Retail
Accounts, Notes, Loans and Financing Receivable [Line Items]
Mortgage loans	16,516	10,593
Retail | Mortgage loans
Accounts, Notes, Loans and Financing Receivable [Line Items]
Total investment income	1,255	66
Commercial
Accounts, Notes, Loans and Financing Receivable [Line Items]
Mortgage loans	15,309	6,298
Commercial | Mortgage loans
Accounts, Notes, Loans and Financing Receivable [Line Items]
Total investment income	1,242	151
Industrial
Accounts, Notes, Loans and Financing Receivable [Line Items]
Mortgage loans	6,329	6,314
Industrial | Mortgage loans
Accounts, Notes, Loans and Financing Receivable [Line Items]
Total investment income	565	90
Multi-family
Accounts, Notes, Loans and Financing Receivable [Line Items]
Mortgage loans	5,593	3,296
Multi-family | Mortgage loans
Accounts, Notes, Loans and Financing Receivable [Line Items]
Total investment income	909	143
Office
Accounts, Notes, Loans and Financing Receivable [Line Items]
Mortgage loans	3,197	1,691
Office | Mortgage loans
Accounts, Notes, Loans and Financing Receivable [Line Items]
Total investment income	385	64
Land | Mortgage loans
Accounts, Notes, Loans and Financing Receivable [Line Items]
Total investment income	0	451
Hospitality
Accounts, Notes, Loans and Financing Receivable [Line Items]
Mortgage loans	4,915	1,339
Hospitality | Mortgage loans
Accounts, Notes, Loans and Financing Receivable [Line Items]
Total investment income	$ 411	$ 223

Other Long-Term Investments - N

Other Long-Term Investments - Narrative (Details) - USD ($) $ in Thousands	3 Months Ended		12 Months Ended
	Dec. 31, 2020	Mar. 31, 2020	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2018
Schedule of Equity Method Investments [Line Items]
Payment to acquire equity method investment			$ 9,767	$ 16,079
Universa Black Swan
Schedule of Equity Method Investments [Line Items]
Equity method investments ownership percentage			100%
Payment to acquire equity method investment				5,000
Hudson Ventures Fund 2 LP units
Schedule of Equity Method Investments [Line Items]
Payment to acquire equity method investment			$ 1,300	1,900
JVM Multi-Family Premier Fund IV
Schedule of Equity Method Investments [Line Items]
Payment to acquire equity method investment				12,000
JVM Preferred Equity Fund, LLC
Schedule of Equity Method Investments [Line Items]
Payment to acquire equity method investment				$ 12,000
Brewer Lane Ventures Fund II LP units
Schedule of Equity Method Investments [Line Items]
Payment to acquire equity method investment			$ 200
JVM Funds LLC units
Schedule of Equity Method Investments [Line Items]
Useful life			7 years
RISCOM
Schedule of Equity Method Investments [Line Items]
Useful life			15 years
Captex Bancshares | Investment in Bank Holding Company
Schedule of Equity Method Investments [Line Items]
Payment to acquire equity method investment					$ 2,000
Gulf Capital Bank | Investment in Bank Holding Company
Schedule of Equity Method Investments [Line Items]
Payment to acquire equity method investment		$ 2,000
Proceeds from sale of equity method investment	$ 1,800		$ 200

Other Long-Term Investments - C

Other Long-Term Investments - Carrying Value of Equity Method Investments (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Schedule of Equity Method Investments [Line Items]
Recorded investment balance	$ 86,789	$ 83,504
Arena SOP LP units
Schedule of Equity Method Investments [Line Items]
Recorded investment balance	8,734	5,692
Arena Special Opportunities Fund, LP units
Schedule of Equity Method Investments [Line Items]
Recorded investment balance	44,504	41,763
Brewer Lane Ventures Fund II LP units
Schedule of Equity Method Investments [Line Items]
Recorded investment balance	200	0
Dowling Capital Partners LP units
Schedule of Equity Method Investments [Line Items]
Recorded investment balance	1,965	2,416
Hudson Ventures Fund 2 LP units
Schedule of Equity Method Investments [Line Items]
Recorded investment balance	3,551	1,913
JVM Funds LLC units
Schedule of Equity Method Investments [Line Items]
Recorded investment balance	22,473	24,000
RISCOM
Schedule of Equity Method Investments [Line Items]
Recorded investment balance	4,037	3,366
Universa Black Swan LP units
Schedule of Equity Method Investments [Line Items]
Recorded investment balance	$ 1,325	$ 4,354

Other Long-Term Investments -_2

Other Long-Term Investments - Net Investment Income (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Schedule of Equity Method Investments [Line Items]
Net investment income	$ 36,931	$ 24,646
Equity Method Investment, Nonconsolidated Investee or Group of Investees
Schedule of Equity Method Investments [Line Items]
Net investment income	6,015	9,280
Arena SOP LP units | Equity Method Investment, Nonconsolidated Investee or Group of Investees
Schedule of Equity Method Investments [Line Items]
Net investment income	3,042	4,717
Arena Special Opportunities Fund, LP units | Equity Method Investment, Nonconsolidated Investee or Group of Investees
Schedule of Equity Method Investments [Line Items]
Net investment income	3,719	3,729
Dowling Capital Partners LP units | Equity Method Investment, Nonconsolidated Investee or Group of Investees
Schedule of Equity Method Investments [Line Items]
Net investment income	502	438
Hudson Ventures Fund 2 LP units | Equity Method Investment, Nonconsolidated Investee or Group of Investees
Schedule of Equity Method Investments [Line Items]
Net investment income	379	(16)
JVM Funds LLC units | Equity Method Investment, Nonconsolidated Investee or Group of Investees
Schedule of Equity Method Investments [Line Items]
Net investment income	(70)	0
RISCOM | Equity Method Investment, Nonconsolidated Investee or Group of Investees
Schedule of Equity Method Investments [Line Items]
Net investment income	1,471	1,058
Universa Black Swan LP units | Equity Method Investment, Nonconsolidated Investee or Group of Investees
Schedule of Equity Method Investments [Line Items]
Net investment income	$ (3,028)	$ (646)

Other Long-Term Investments - U

Other Long-Term Investments - Unfunded Commitment of Equity Method Investments (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Schedule of Equity Method Investments [Line Items]
Unfunded Commitment	$ 6,982	$ 3,431
Brewer Lane Ventures Fund II LP units
Schedule of Equity Method Investments [Line Items]
Unfunded Commitment	4,800	0
Dowling Capital Partners LP units
Schedule of Equity Method Investments [Line Items]
Unfunded Commitment	386	368
Hudson Ventures Fund 2 LP units
Schedule of Equity Method Investments [Line Items]
Unfunded Commitment	$ 1,796	$ 3,063

Other Long-Term Investments - I

Other Long-Term Investments - Investment in RISCOM (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Equity Method Investment, Difference Between Carrying Amount and Underlying Equity [Abstract]
Recorded investment balance	$ 86,789	$ 83,504
RISCOM
Equity Method Investment, Difference Between Carrying Amount and Underlying Equity [Abstract]
Underlying equity	2,292	1,378
Difference	1,745	1,988
Recorded investment balance	$ 4,037	$ 3,366

Other Long-Term Investments -_3

Other Long-Term Investments - Investment in JVN Funds (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Schedule of Equity Method Investments [Line Items]
Recorded investment balance	$ 86,789	$ 83,504
JVM Funds LLC units
Schedule of Equity Method Investments [Line Items]
Underlying equity	21,565	24,000
Difference	908	0
Recorded investment balance	$ 22,473	$ 24,000

Other Long-Term Investments - S

Other Long-Term Investments - Schedule of Indirect Investments (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Schedule of Equity Method Investments [Line Items]
Carrying Value	$ 86,789	$ 83,504
Unfunded Commitment	6,982	3,431
Investment in indirect loans and loan collateral
Schedule of Equity Method Investments [Line Items]
Carrying Value	38,436	43,955
Unfunded Commitment	0	16,563
Investment in indirect loans and loan collateral | SMA1
Schedule of Equity Method Investments [Line Items]
Carrying Value	36,426	33,100
Unfunded Commitment	0	0
Investment in indirect loans and loan collateral | SMA2
Schedule of Equity Method Investments [Line Items]
Carrying Value	2,010	10,855
Unfunded Commitment	$ 0	$ 16,563

Property and Equipment - Proper

Property and Equipment - Property, Plant and Equipment (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Property, Plant and Equipment [Line Items]
Property, equipment and other, gross	$ 35,903	$ 33,591
Accumulated depreciation	(27,229)	(23,964)
Total	8,674	9,627
Leasehold improvements
Property, Plant and Equipment [Line Items]
Property, equipment and other, gross	2,670	2,761
Equipment
Property, Plant and Equipment [Line Items]
Property, equipment and other, gross	7,230	7,477
Software
Property, Plant and Equipment [Line Items]
Property, equipment and other, gross	25,964	23,314
Other
Property, Plant and Equipment [Line Items]
Property, equipment and other, gross	$ 39	$ 39

Property and Equipment - Deprec

Property and Equipment - Depreciation (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Property, Plant and Equipment [Abstract]
Depreciation expense	$ 3,582	$ 3,636

Leases - Narrative (Details)

Leases - Narrative (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Lessee, Lease, Description [Line Items]
Total lease expense	$ 2,634	$ 2,734
Operating lease expense	$ 2,414	$ 2,607
Minimum
Lessee, Lease, Description [Line Items]
Remaining lease term	1 year
Maximum
Lessee, Lease, Description [Line Items]
Remaining lease term	7 years

Leases - Lease, Cost (Details)

Leases - Lease, Cost (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Leases [Abstract]
Operating lease right-of-use assets	$ 8,214	$ 10,532
Operating lease liabilities	$ 8,616	$ 10,921
Operating lease weighted-average remaining lease term	5 years	5 years 8 months 23 days
Operating lease weighted-average discount rate	3.16%	3.12%
Operating lease, liability, statement of financial position	Accounts payable and accrued liabilities	Accounts payable and accrued liabilities
Operating Lease, Right-of-Use Asset, Statement of Financial Position [Extensible Enumeration]	Other assets	Other assets

Leases - Cash Flow Information

Leases - Cash Flow Information (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Leases [Abstract]
Operating lease expense	$ 2,414	$ 2,607
Short-term lease expense	220	127
Total lease expense	2,634	2,734
Operating cash outflows from operating leases	$ 2,382	$ 2,361

Leases - Lessee, Operating Leas

Leases - Lessee, Operating Lease, Liability, Maturity (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Lessee, Operating Lease, Liability, to be Paid [Abstract]
2023	$ 2,206
2024	1,996
2025	1,465
2026	1,227
2027	1,116
Thereafter	1,189
Total future minimum operating lease payments	9,199
Less imputed interest	(583)
Operating lease liabilities	$ 8,616	$ 10,921

Subordinated Debt - Summary of

Subordinated Debt - Summary of Subordinated Debt (Details) - Subordinated Debt - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Debt Instrument [Line Items]
Subordinated debt, net of debt issuance costs	$ 78,609	$ 78,529
Junior Subordinated Notes Due 2036
Debt Instrument [Line Items]
Principal	59,794	59,794
Less: Debt issuance costs	(657)	(705)
Subordinate Debt Due 2039
Debt Instrument [Line Items]
Principal	20,000	20,000
Less: Debt issuance costs	$ (528)	$ (560)

Subordinated Debt - Narrative (

Subordinated Debt - Narrative (Details) - Subordinated Debt - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	May 31, 2019	Aug. 02, 2006
Subordinate Debt Due 2039
Debt Instrument [Line Items]
Face amount			$ 20,000
Debt term			8 years
Less: Debt issuance costs	$ 528	$ 560
Subordinate Debt Due 2039 | Debt Interest Rate, First 8 Years
Debt Instrument [Line Items]
Stated interest rate			7.25%
Debt term			8 years
Subordinate Debt Due 2039 | Debt Interest Rate, After Year 8
Debt Instrument [Line Items]
Stated interest rate			8.25%
Junior Subordinated Notes Due 2036, Capital Securities
Debt Instrument [Line Items]
Face amount				$ 58,000
Junior Subordinated Notes Due 2036, Common Stock
Debt Instrument [Line Items]
Face amount				$ 1,800
Junior Subordinated Notes Due 2036
Debt Instrument [Line Items]
Face amount	$ 59,800
Stated interest rate	4.77%
Less: Debt issuance costs	$ 657	$ 705
Junior Subordinated Notes Due 2036 | London Interbank Offered Rate (LIBOR)
Debt Instrument [Line Items]
Basis spread on variable rate	3.40%

Notes_Payable - Summary of Note

Notes Payable - Summary of Notes Payable (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Term Loan, due December 2024 | Secured Debt
Debt Instrument [Line Items]
Long-term debt	$ 50,000	$ 50,000

Notes_Payable - Narrative (Deta

Notes Payable - Narrative (Details)	12 Months Ended
	Dec. 31, 2022 USD ($)
Term Loan, due December 2024 | Secured Debt
Debt Instrument [Line Items]
Face amount	$ 50,000,000
Term Loan, due December 2024 | Secured Debt | London Interbank Offered Rate (LIBOR)
Debt Instrument [Line Items]
Basis spread on variable rate	4.39%
Term Loan, due December 2024 | Secured Debt | Applicable Margin Rate
Debt Instrument [Line Items]
Basis spread on variable rate	1.65%
Revolving Line of Credit, due December 2024 | Line of Credit | Revolving Credit Facility
Debt Instrument [Line Items]
Maximum borrowing capacity	$ 50,000,000
Unused capacity, commitment fee percentage	0.25%
Accordion feature, increase limit	$ 75,000,000
Revolving Line of Credit, due December 2024 | Line of Credit | London Interbank Offered Rate (LIBOR) | Revolving Credit Facility
Debt Instrument [Line Items]
Basis spread on variable rate	4.39%
Revolving Line of Credit, due December 2024 | Line of Credit | Applicable Margin Rate | Revolving Credit Facility
Debt Instrument [Line Items]
Basis spread on variable rate	1.65%

Notes_Payable - Schedule of Deb

Notes Payable - Schedule of Debt Interest Payment (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Debt Disclosure [Abstract]
Interest payments on term loan	$ 1,443	$ 894
Interest payments on revolving line of credit	$ 0	$ 127

Stockholders_ Equity - Narrativ

Stockholders’ Equity - Narrative (Details) - $ / shares	Dec. 31, 2022	Dec. 31, 2021	Apr. 24, 2020
Equity [Abstract]
Preferred stock, redemption price (in dollars per share)			$ 50
Preferred stock, convertible, conversion price (in dollars per share)	$ 6.04	$ 6.04	6.96
Preferred stock, liquidation preference (in dollars per share)			$ 50

Stockholders_ Equity - Schedule

Stockholders’ Equity - Schedule of Stock by Class (Details) - shares	Dec. 31, 2022	Dec. 31, 2021
Equity [Abstract]
Preferred stock, shares outstanding (in shares)	1,969,660	1,970,124
Common shares upon conversion of preferred shares (in shares)	16,305,113

Income Taxes - Schedule of Comp

Income Taxes - Schedule of Components of Income Tax Expense (Benefit) (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Income Tax Disclosure [Abstract]
Current income tax expense	$ 120	$ 0
Deferred tax expense related to temporary differences	10,267	9,992
Total income tax expense	$ 10,387	$ 9,992

Income Taxes - Schedule of Effe

Income Taxes - Schedule of Effective Income Tax Rate Reconciliation (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Amount
Income tax expense at federal statutory rate	$ 10,454	$ 10,145
Tax advantaged investments	(324)	(256)
Other	257	103
Total income tax expense	$ 10,387	$ 9,992
Percentage
Income tax expense at federal statutory rate	21%	21%
Tax advantaged investments	(0.70%)	(0.50%)
Other	0.60%	0.20%
Total income tax expense	20.90%	20.70%

Income Taxes - Schedule of Defe

Income Taxes - Schedule of Deferred Tax Assets and Liabilities (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Deferred tax assets:
Net operating losses	$ 14,966	$ 28,009
Losses and loss adjustment expenses	10,748	7,782
Unearned premiums	11,959	9,461
Intangibles	607	1,632
Capital loss carryfoward	1,321	0
Unrealized losses on investments	11,563	0
Stock options/awards	1,107	627
Other	3,369	1,034
Total deferred tax assets	55,640	48,545
Less valuation allowance	586	586	$ 586
Total deferred tax assets after valuation allowance	55,054	47,959
Deferred tax liabilities:
Deferred policy acquisition costs	8,209	6,063
Depreciation	1,481	1,459
Investments	7,144	5,507
Unrealized gains on investments	0	1,230
Other	2,032	37
Total deferred tax liabilities	18,866	14,296
Deferred income taxes	$ 36,188	$ 33,663

Income Taxes - Narrative (Detai

Income Taxes - Narrative (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Income Tax Disclosure [Abstract]
Operating loss carryforwards	$ 71,300
Operating loss carryforwards, limitations on use, amount	58,600
Deferred tax subject to expiration	2,800
Deferred tax effected by expiration	600
Capital loss carryfoward	$ 1,321	$ 0

Income Taxes - Summary of Valua

Income Taxes - Summary of Valuation Allowance (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Deferred Tax Assets, Valuation Allowance [Abstract]
Balance at beginning of year	$ 586	$ 586
Balance at end of year	$ 586	$ 586

Reserves for Losses and Loss _3

Reserves for Losses and Loss Adjustment Expenses - Schedule of Liability for Unpaid Claims and Claims Adjustment Expense (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Reserves for losses and LAE, beginning of period	$ 979,549	$ 856,780
Less: reinsurance recoverable on unpaid claims, beginning of period	(381,338)	(375,178)
Reserves for losses and LAE, beginning of period, net of reinsurance	598,211	481,602
Incurred, net of reinsurance, related to:
Current period	393,939	338,348
Prior years	14,385	28,000
Total incurred, net of reinsurance	408,324	366,348
Paid, net of reinsurance, related to:
Current period	105,928	77,551
Prior years	194,836	172,188
Total paid	300,764	249,739
Net reserves for losses and LAE, end of period	705,771	598,211
Plus: reinsurance recoverable on unpaid claims, end of period	435,986	381,338
Reserves for losses and LAE, end of period	$ 1,141,757	$ 979,549

Reserves for Losses and Loss _4

Reserves for Losses and Loss Adjustment Expenses - Narrative (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Liability for Claims and Claims Adjustment Expense [Line Items]
Reserves for losses and LAE, increase (decrease)	$ 14,400
Prior year claims incurred, unfavorable (favorable) development	14,385	$ 28,000
Exited Lines
Liability for Claims and Claims Adjustment Expense [Line Items]
Reserves for losses and LAE, increase (decrease)	14,500
Prior year claims incurred, unfavorable (favorable) development		28,800
Multi-line Solutions
Liability for Claims and Claims Adjustment Expense [Line Items]
Reserves for losses and LAE, increase (decrease)	(10,800)
Prior year claims incurred, unfavorable (favorable) development		4,800
Liability for unpaid claims and claims adjustment	2,300	8,400
Short Tail/Monoline Specialty
Liability for Claims and Claims Adjustment Expense [Line Items]
Reserves for losses and LAE, increase (decrease)	$ 0
Prior year claims incurred, unfavorable (favorable) development		$ (5,600)

Reserves for Losses and Loss _5

Reserves for Losses and Loss Adjustment Expenses - Schedule of Short-Duration Insurance Contracts (Details) $ in Thousands	Dec. 31, 2022 USD ($) claim	Dec. 31, 2021 USD ($)	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]
Total net reserves for loss and LAE	$ 698,091
Short Tail/Monoline Specialty
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	371,536
Cumulative net paid loss and LAE from the table below	(218,145)
Net reserves for loss and LAE before 2018	5,512
Total net reserves for loss and LAE	158,903
Cumulative net paid loss and LAE	218,145
Multi-line Solutions
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	1,177,516
Cumulative net paid loss and LAE from the table below	(821,766)
Net reserves for loss and LAE before 2018	4,945
Total net reserves for loss and LAE	360,695
Cumulative net paid loss and LAE	821,766
Exited Lines
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	782,059
Cumulative net paid loss and LAE from the table below	(612,456)
Net reserves for loss and LAE before 2018	8,890
Total net reserves for loss and LAE	178,493
Cumulative net paid loss and LAE	612,456
Accident Year 2013 | Multi-line Solutions
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	69,515	$ 69,496	$ 75,419	$ 74,987	$ 74,701	$ 75,196	$ 73,382	$ 64,439	$ 71,800	$ 66,517
Cumulative net paid loss and LAE from the table below	(74,178)	(75,030)	(75,340)	(75,117)	(73,511)	(67,857)	(59,460)	(48,673)	(40,425)	(19,912)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 1,994
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	3,324
Cumulative net paid loss and LAE	$ 74,178	75,030	75,340	75,117	73,511	67,857	59,460	48,673	40,425	19,912
Accident Year 2013 | Exited Lines
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	54,130	53,236	49,486	49,850	48,372	48,372	46,437	44,909	37,993	44,791
Cumulative net paid loss and LAE from the table below	(49,605)	(48,322)	(48,069)	(47,101)	(44,186)	(41,158)	(42,995)	(36,890)	(17,904)	(4,763)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 2,031
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	2,640
Cumulative net paid loss and LAE	$ 49,605	48,322	48,069	47,101	44,186	41,158	42,995	36,890	17,904	$ 4,763
Accident Year 2014 | Multi-line Solutions
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	120,777	120,697	118,995	117,783	116,970	116,970	115,749	100,355	100,355
Cumulative net paid loss and LAE from the table below	(104,076)	(106,214)	(105,756)	(104,984)	(101,984)	(96,639)	(81,251)	(63,699)	(32,530)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 946
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	4,977
Cumulative net paid loss and LAE	$ 104,076	106,214	105,756	104,984	101,984	96,639	81,251	63,699	32,530
Accident Year 2014 | Exited Lines
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	71,761	71,219	69,920	68,855	63,729	63,729	62,425	57,904	64,186
Cumulative net paid loss and LAE from the table below	(55,737)	(53,615)	(53,290)	(52,450)	(49,906)	(50,785)	(42,141)	(30,863)	(9,700)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 11,475
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	4,149
Cumulative net paid loss and LAE	$ 55,737	53,615	53,290	52,450	49,906	50,785	42,141	30,863	$ 9,700
Accident Year 2015 | Multi-line Solutions
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	122,902	122,839	121,746	119,216	117,024	117,024	114,266	103,191
Cumulative net paid loss and LAE from the table below	(118,166)	(117,295)	(114,098)	(108,291)	(99,401)	(88,833)	(72,137)	(44,152)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 2,446
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	5,364
Cumulative net paid loss and LAE	$ 118,166	117,295	114,098	108,291	99,401	88,833	72,137	44,152
Accident Year 2015 | Exited Lines
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	84,058	83,365	80,678	75,187	70,803	68,008	65,063	61,810
Cumulative net paid loss and LAE from the table below	(81,789)	(80,312)	(77,981)	(73,100)	(65,269)	(55,610)	(41,653)	(9,026)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 1,779
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	4,550
Cumulative net paid loss and LAE	$ 81,789	80,312	77,981	73,100	65,269	55,610	41,653	$ 9,026
Accident Year 2016 | Multi-line Solutions
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	73,318	73,200	69,701	62,643	62,843	62,843	63,223
Cumulative net paid loss and LAE from the table below	(71,565)	(63,893)	(60,864)	(58,895)	(53,352)	(42,528)	(23,239)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 1,523
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	4,691
Cumulative net paid loss and LAE	$ 71,565	63,893	60,864	58,895	53,352	42,528	23,239
Accident Year 2016 | Exited Lines
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	105,852	104,612	103,602	93,324	91,119	92,743	93,526
Cumulative net paid loss and LAE from the table below	(87,966)	(85,794)	(81,516)	(78,070)	(70,253)	(57,638)	(36,592)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 5,975
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	4,858
Cumulative net paid loss and LAE	$ 87,966	85,794	81,516	78,070	70,253	57,638	$ 36,592
Accident Year 2017 | Multi-line Solutions
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	78,762	78,578	72,913	64,260	65,332	65,332
Cumulative net paid loss and LAE from the table below	(69,096)	(67,243)	(64,235)	(53,093)	(41,945)	(23,770)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 4,331
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	5,515
Cumulative net paid loss and LAE	$ 69,096	67,243	64,235	53,093	41,945	23,770
Accident Year 2017 | Exited Lines
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	98,646	97,011	95,119	82,545	80,341	75,919
Cumulative net paid loss and LAE from the table below	(68,434)	(63,516)	(56,839)	(51,985)	(52,103)	(34,177)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 33,630
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	4,309
Cumulative net paid loss and LAE	$ 68,434	63,516	56,839	51,985	52,103	$ 34,177
Accident Year 2018 | Short Tail/Monoline Specialty
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	34,363	36,863	33,570	33,570	33,570
Cumulative net paid loss and LAE from the table below	(33,446)	(33,522)	(31,323)	(31,907)	(24,754)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 559
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	858
Cumulative net paid loss and LAE	$ 33,446	33,522	31,323	31,907	24,754
Accident Year 2018 | Multi-line Solutions
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	74,209	73,868	73,868	74,476	74,476
Cumulative net paid loss and LAE from the table below	(70,080)	(64,119)	(50,320)	(42,568)	(26,201)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 10,202
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	5,041
Cumulative net paid loss and LAE	$ 70,080	64,119	50,320	42,568	26,201
Accident Year 2018 | Exited Lines
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	96,685	90,348	78,902	68,125	73,492
Cumulative net paid loss and LAE from the table below	(90,791)	(80,448)	(67,262)	(60,149)	(25,552)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 335
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	4,864
Cumulative net paid loss and LAE	$ 90,791	80,448	67,262	60,149	$ 25,552
Accident Year 2019 | Short Tail/Monoline Specialty
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	48,800	45,301	48,101	62,922
Cumulative net paid loss and LAE from the table below	(45,031)	(41,484)	(40,228)	(33,714)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 230
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	1,015
Cumulative net paid loss and LAE	$ 45,031	41,484	40,228	33,714
Accident Year 2019 | Multi-line Solutions
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	110,896	106,432	106,432	107,432
Cumulative net paid loss and LAE from the table below	(96,601)	(78,803)	(59,529)	(33,019)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 1,487
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	6,021
Cumulative net paid loss and LAE	$ 96,601	78,803	59,529	33,019
Accident Year 2019 | Exited Lines
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	106,594	92,118	90,598	87,115
Cumulative net paid loss and LAE from the table below	(82,878)	(66,682)	(63,243)	(28,636)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 2,487
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	5,549
Cumulative net paid loss and LAE	$ 82,878	66,682	63,243	$ 28,636
Accident Year 2020 | Short Tail/Monoline Specialty
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	64,859	64,859	66,359
Cumulative net paid loss and LAE from the table below	(70,684)	(56,499)	(30,974)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 6,614
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	1,258
Cumulative net paid loss and LAE	$ 70,684	56,499	30,974
Accident Year 2020 | Multi-line Solutions
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	134,124	140,880	140,880
Cumulative net paid loss and LAE from the table below	(83,533)	(67,216)	(33,538)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 27,390
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	5,393
Cumulative net paid loss and LAE	$ 83,533	67,216	33,538
Accident Year 2020 | Exited Lines
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	86,700	86,700	83,900
Cumulative net paid loss and LAE from the table below	(63,468)	(54,950)	(24,468)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 5,196
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	4,719
Cumulative net paid loss and LAE	$ 63,468	54,950	$ 24,468
Accident Year 2021 | Short Tail/Monoline Specialty
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	100,172	100,172
Cumulative net paid loss and LAE from the table below	(49,526)	(14,754)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 25,018
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	1,428
Cumulative net paid loss and LAE	$ 49,526	14,754
Accident Year 2021 | Multi-line Solutions
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	169,566	173,568
Cumulative net paid loss and LAE from the table below	(78,923)	(39,388)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 60,497
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	6,486
Cumulative net paid loss and LAE	$ 78,923	39,388
Accident Year 2021 | Exited Lines
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	46,146	49,957
Cumulative net paid loss and LAE from the table below	(15,449)	(9,856)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 33,733
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	2,265
Cumulative net paid loss and LAE	$ 15,449	$ 9,856
Accident Year 2022 | Short Tail/Monoline Specialty
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	123,342
Cumulative net paid loss and LAE from the table below	(19,458)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 80,974
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	1,282
Cumulative net paid loss and LAE	$ 19,458
Accident Year 2022 | Multi-line Solutions
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	223,447
Cumulative net paid loss and LAE from the table below	(55,548)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 105,571
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	7,330
Cumulative net paid loss and LAE	$ 55,548
Accident Year 2022 | Exited Lines
Claims Development [Line Items]
Incurred losses and ALAE, net of reinsurance	31,487
Cumulative net paid loss and LAE from the table below	(16,339)
Short-Duration Insurance Contracts, Incurred but Not Reported (IBNR) Claims Liability, Net	$ 9,336
Short-Duration Insurance Contract, Cumulative Number of Reported Claims | claim	185
Cumulative net paid loss and LAE	$ 16,339

Reserves for Losses and Loss _6

Reserves for Losses and Loss Adjustment Expenses - Reconciliation of Claims Development to Liability (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Short-Duration Insurance Contracts, Reconciliation of Claims Development to Liability [Line Items]
Reserves for losses and LAE, net of reinsurance	$ 698,091
Total reinsurance recoverable on unpaid claims	435,986	$ 381,338	$ 375,178
Unallocated LAE	7,680
Reserves for losses and loss adjustment expenses	1,141,757	$ 979,549	$ 856,780
Short Tail/Monoline Specialty
Short-Duration Insurance Contracts, Reconciliation of Claims Development to Liability [Line Items]
Reserves for losses and LAE, net of reinsurance	158,903
Total reinsurance recoverable on unpaid claims	147,435
Multi-line Solutions
Short-Duration Insurance Contracts, Reconciliation of Claims Development to Liability [Line Items]
Reserves for losses and LAE, net of reinsurance	360,695
Total reinsurance recoverable on unpaid claims	252,673
Exited Lines
Short-Duration Insurance Contracts, Reconciliation of Claims Development to Liability [Line Items]
Reserves for losses and LAE, net of reinsurance	178,493
Total reinsurance recoverable on unpaid claims	$ 35,878

Reserves for Losses and Loss _7

Reserves for Losses and Loss Adjustment Expenses - Schedule of Historical Claims Duration (Details)	Dec. 31, 2022
Short Tail/Monoline Specialty
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]
Year 1	56%
Year 2	24%
Year 3	10.10%
Year 4	6.20%
Year 5	2.90%
Year 6	0.10%
Year 7	0%
Year 8	0.60%
Year 9	0.10%
Year 10	0%
Multi-line Solutions
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]
Year 1	40.70%
Year 2	26.10%
Year 3	14.90%
Year 4	8.10%
Year 5	5.10%
Year 6	3.60%
Year 7	1.20%
Year 8	0%
Year 9	0.20%
Year 10	0.10%
Exited Lines
Short-Duration Insurance Contracts, Historical Claims Duration [Line Items]
Year 1	43.40%
Year 2	26.70%
Year 3	12.70%
Year 4	8.60%
Year 5	4.50%
Year 6	1.70%
Year 7	1.10%
Year 8	0.90%
Year 9	0.40%
Year 10	0%

Premiums - Schedule of Premiums

Premiums - Schedule of Premiums Written (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Effects of Reinsurance [Line Items]
Direct and assumed premiums written	$ 1,143,952	$ 939,859
Direct and assumed premiums, business line benchmark | Product concentration risk
Effects of Reinsurance [Line Items]
Concentration risk, percentage	100%	100%
Property
Effects of Reinsurance [Line Items]
Direct and assumed premiums written	$ 279,384	$ 235,686
Property | Direct and assumed premiums, business line benchmark | Product concentration risk
Effects of Reinsurance [Line Items]
Concentration risk, percentage	24.40%	25.10%
Commercial Auto Liability
Effects of Reinsurance [Line Items]
Direct and assumed premiums written	$ 243,300	$ 227,853
Commercial Auto Liability | Direct and assumed premiums, business line benchmark | Product concentration risk
Effects of Reinsurance [Line Items]
Concentration risk, percentage	21.30%	24.20%
General Liability
Effects of Reinsurance [Line Items]
Direct and assumed premiums written	$ 140,557	$ 116,953
General Liability | Direct and assumed premiums, business line benchmark | Product concentration risk
Effects of Reinsurance [Line Items]
Concentration risk, percentage	12.30%	12.40%
Group Accident & Health
Effects of Reinsurance [Line Items]
Direct and assumed premiums written	$ 130,808	$ 112,146
Group Accident & Health | Direct and assumed premiums, business line benchmark | Product concentration risk
Effects of Reinsurance [Line Items]
Concentration risk, percentage	11.40%	11.90%
Professional Liability
Effects of Reinsurance [Line Items]
Direct and assumed premiums written	$ 90,418	$ 61,466
Professional Liability | Direct and assumed premiums, business line benchmark | Product concentration risk
Effects of Reinsurance [Line Items]
Concentration risk, percentage	7.90%	6.50%
Excess Liability
Effects of Reinsurance [Line Items]
Direct and assumed premiums written	$ 79,922	$ 52,176
Excess Liability | Direct and assumed premiums, business line benchmark | Product concentration risk
Effects of Reinsurance [Line Items]
Concentration risk, percentage	7%	5.60%
Surety
Effects of Reinsurance [Line Items]
Direct and assumed premiums written	$ 79,062	$ 51,792
Surety | Direct and assumed premiums, business line benchmark | Product concentration risk
Effects of Reinsurance [Line Items]
Concentration risk, percentage	6.90%	5.60%
Workers’ Compensation
Effects of Reinsurance [Line Items]
Direct and assumed premiums written	$ 51,790	$ 41,890
Workers’ Compensation | Direct and assumed premiums, business line benchmark | Product concentration risk
Effects of Reinsurance [Line Items]
Concentration risk, percentage	4.50%	4.50%
Commercial Auto Physical Damage
Effects of Reinsurance [Line Items]
Direct and assumed premiums written	$ 48,711	$ 39,897
Commercial Auto Physical Damage | Direct and assumed premiums, business line benchmark | Product concentration risk
Effects of Reinsurance [Line Items]
Concentration risk, percentage	4.30%	4.20%

Commission and Fee Income (Deta

Commission and Fee Income (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Disaggregation of Revenue [Line Items]
Total commission and fee income	$ 5,199	$ 3,973
SUA commission revenue
Disaggregation of Revenue [Line Items]
Total commission and fee income	3,224	2,037
SUA fee income
Disaggregation of Revenue [Line Items]
Total commission and fee income	1,597	1,185
Other
Disaggregation of Revenue [Line Items]
Total commission and fee income	$ 378	$ 751

Commission and Fee Income - Con

Commission and Fee Income - Contract Asset (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Revenue from Contract with Customer [Abstract]
Contract asset	$ 1,292	$ 1,209

Underwriting, Acquisition and_3

Underwriting, Acquisition and Insurance Expenses (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Other Income and Expenses [Abstract]
Amortization of policy acquisition costs	$ 65,695	$ 47,061
Other operating and general expenses	116,476	91,437
Total underwriting, acquisition and insurance expenses	$ 182,171	$ 138,498

Reinsurance - Schedule of Premi

Reinsurance - Schedule of Premiums Written and Earned (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Written
Direct premiums	$ 1,012,239	$ 842,318
Assumed premiums	131,713	97,541
Ceded premiums	(468,409)	(410,716)
Net premiums	675,543	529,143
Earned
Direct premiums	951,121	816,837
Assumed premiums	113,610	102,352
Ceded premiums	(448,737)	(419,366)
Net earned premium	615,994	499,823
Ceded losses and LAE incurred	$ 311,257	$ 248,360

Reinsurance - Reinsurance Recov

Reinsurance - Reinsurance Recoverables and Ceded Premiums (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Insurance [Abstract]
Total reinsurance recoverable on unpaid claims	$ 435,986	$ 381,338	$ 375,178
Paid losses and loss adjustment expense ceded	107,228	90,761
Loss portfolio transfer	38,145	64,228
Reinsurance recoverables	581,359	536,327
Ceded unearned premium	$ 157,645	$ 137,973

Reinsurance - Narrative (Detail

Reinsurance - Narrative (Details) - USD ($) $ in Thousands	3 Months Ended	12 Months Ended
	Mar. 31, 2020	Dec. 31, 2022	Dec. 31, 2021
Insurance [Abstract]
Market value of trust funds		$ 128,000
Liability for claims and claims adjustment expense, loss portfolio transfer	$ 127,400
Strengthening of reserves subject to the LPT		14,385	$ 28,000
Reinsurance recoveries under the LPT		$ 5,813	$ 11,937

Reinsurance - Impact of LPT (De

Reinsurance - Impact of LPT (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Effects of Reinsurance [Line Items]
Strengthening of reserves subject to the LPT	$ (14,385)	$ (28,000)
Reinsurance recoveries under the LPT	5,813	11,937
Losses and loss adjustment expenses	$ (8,572)	(16,063)
Loss Portfolio transfer
Effects of Reinsurance [Line Items]
Strengthening of reserves subject to the LPT		$ (28,000)

Reinsurance - Deposit Assets (D

Reinsurance - Deposit Assets (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Insurance [Abstract]
Deposit asset	$ 41,801	$ 45,003

Stock Based Compensation - Narr

Stock Based Compensation - Narrative (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Forfeitures	$ 38	$ 843
Granted (in shares)	198,842	332,658
Unrecognized compensation cost	$ 2,800
Unrecognized compensation cost, recognition period	1 year 7 months 6 days
Legacy Programs
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Purchase price of common stock, percent		30%
Requisite service period		3 years
Sale of stock, number of shares issued (in shares)		63,374
Shares issued in period (in shares)		63,374
Maximum finance option	70%
Shares forfeited (in shares)		21,314
Stock notes receivable, stock awards returned (in shares)		10,657
Stock notes receivable, stock awards returned		$ 800
Stock notes receivable, stock awards forfeited (in shares)		10,657
Forfeitures		$ 800
Legacy Programs | Minimum
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Requisite service period		0 years
Stock notes receivable interest, percent	0.95%
Legacy Programs | Maximum
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Requisite service period		3 years
Stock notes receivable interest, percent	2.80%
Legacy Programs | Director
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Shares issued in period (in shares)		51,889
Long Term Incentive Plan
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Authorized target common shares (in shares)	198,842	217,395
Shares granted, value	$ 2,600	$ 2,500
Long Term Incentive Plan | Director
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Requisite service period	1 year
Granted (in shares)	15,196

Stock Based Compensation - Sche

Stock Based Compensation - Schedule of Common Stock Notes Receivable (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Legacy Programs
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Common stock notes receivable	$ 512	$ 1,630

Stock Based Compensation - Summ

Stock Based Compensation - Summary of Equity Awards (Details) - Long Term Incentive Plan - shares	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Authorized target common shares (in shares)	198,842	217,395
Market condition awards
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Requisite Service Period	3 years	3 years
Authorized target common shares (in shares)	28,495	46,474
Market condition awards | Minimum
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Award Payout Range	0%	0%
Market condition awards | Maximum
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Award Payout Range	150%	150%
Performance condition awards
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Requisite Service Period	3 years	3 years
Authorized target common shares (in shares)	26,210	29,501
Performance condition awards | Minimum
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Award Payout Range	0%	0%
Performance condition awards | Maximum
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Award Payout Range	150%	150%
Restricted share and stock unit awards
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Requisite Service Period		3 years
Authorized target common shares (in shares)	144,137	141,420
Restricted share and stock unit awards | Minimum
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Requisite Service Period	1 year
Restricted share and stock unit awards | Maximum
Share-Based Compensation Arrangement by Share-Based Payment Award [Line Items]
Requisite Service Period	3 years

Stock Based Compensation - Sc_2

Stock Based Compensation - Schedule of Nonvested Share Activity (Details) - $ / shares	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Weighted-Average Grant-Date Fair Value
Non-vested, beginning period (in dollars per share)	$ 13.23	$ 19.47
Granted (in dollars per share)	14.17	11.95
Vested (in dollars per share)	15.16	14.20
Forfeited (in dollars per share)	12.51	16.01
Non-vested, ending period (in dollars per share)	$ 12.55	$ 13.23
Number of Common Shares
Non-vested, beginning period (in shares)	375,643	84,671
Granted (in shares)	198,842	332,658
Vested (in shares)	(144,042)	(6,514)
Forfeited (in shares)	(10,547)	(35,172)
Non-vested, ending period (in shares)	419,896	375,643

Stock Based Compensation - Sc_3

Stock Based Compensation - Schedule of Share-Based Compensation Expense (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Share-Based Payment Arrangement [Abstract]
Stock-based compensation expense	$ 2,325	$ 1,365
Forfeitures	38	843
Total	$ 2,287	$ 522

Earnings Per Share - Schedule o

Earnings Per Share - Schedule of Earnings Per Share, Basic and Diluted (Details) - USD ($) $ / shares in Units, $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Numerator
Net income	$ 39,396	$ 38,317
Less: Undistributed income allocated to participating securities	(18,879)	(18,507)
Net income attributable to common shareholders	20,517	19,810
Add back: Undistributed income allocated to participating securities	18,879	18,507
Net income (numerator for diluted earnings per share under the two-class method)	$ 39,396	$ 38,317
Denominator
Basic weighted-average common shares (in shares)	16,568,393	16,308,712
Preferred shares (if converted method) (in shares)	15,245,533	15,235,568
Contingently issuable instruments (treasury stock method) (in shares)	519,080	723,146
Market condition awards (contingently issuable) (in shares)	94,936	67,598
Performance awards (contingently issuable) (in shares)	39,148	0
Restricted stock units (treasury stock method) (in shares)	186,104	133,024
Diluted weighted-average common share equivalents (in shares)	32,653,194	32,468,048
Basic earnings per share (in dollar per share)	$ 1.24	$ 1.21
Diluted earnings per share (in dollar per share)	$ 1.21	$ 1.18

Earnings Per Share - Schedule_2

Earnings Per Share - Schedule of Antidilutive Securities Excluded from Computation of Earnings Per Share (Details) - shares	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Contingently issuable instruments (treasury stock method)
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities (in shares)	60,576	0

Earnings Per Share - Schedule_3

Earnings Per Share - Schedule of Earnings Per Share, Excluded from Basic Earnings (Details) - shares	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Contingently issuable instruments
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities (in shares)	1,082,521	1,428,029
Common shares
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities (in shares)	22,919	192,609
Preferred shares, if converted
Antidilutive Securities Excluded from Computation of Earnings Per Share [Line Items]
Antidilutive securities (in shares)	1,059,602	1,235,420

Employee Benefit Plans (Details

Employee Benefit Plans (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Retirement Benefits [Abstract]
401(k) matching contributions	$ 2,389	$ 2,288

Related Party Transactions - We

Related Party Transactions - Westaim Transactions (Details) - USD ($) $ in Thousands		12 Months Ended
	Apr. 24, 2020	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2015
Related Party Transaction [Line Items]
Unrealized losses on investment in Westaim		$ (15,058)	$ 15,251
Skyward Specialty Insurance Group | Westaim HIIG LP
Related Party Transaction [Line Items]
Ownership interest		44.50%	71%
Principal Owner | Purchase Of Common Stock | Westaim
Related Party Transaction [Line Items]
Related party transaction, shares				3,076,924
Related party transaction, consideration received				$ 8,400
Affiliated entity | Westaim HIIG LP Affiliates
Related Party Transaction [Line Items]
Sale of stock, consideration	$ 68,600
Cash proceeds from sale of preferred stock	68,100
Sale of stock, stock note receivable	500
Affiliated entity | Management services agreement | Westaim
Related Party Transaction [Line Items]
Expenses from related party transactions			$ 500
Limited partner | Skyward Specialty Insurance Group | Westaim
Related Party Transaction [Line Items]
Ownership interest		44.70%	44.70%
Limited partner | Westaim
Related Party Transaction [Line Items]
Sale of stock, consideration	44,000
Unrealized losses on investment in Westaim		$ (2,283)	$ (1,971)
Cash proceeds from sale of preferred stock	$ 44,000
Limited partner | Management services agreement | Westaim HIIG LP
Related Party Transaction [Line Items]
Ownership interest threshold (less than)		8%
Limited partner | Management services agreement | Westaim
Related Party Transaction [Line Items]
Transaction amount during the period		$ 500
Expenses from related party transactions		$ 500

Related Party Transactions - RI

Related Party Transactions - RISCOM Transactions (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2016
Related Party Transaction [Line Items]
Net earned premium	$ 615,994	$ 499,823
Premiums receivable	139,215	112,158
Affiliated entity | Agency agreement | RISCOM
Related Party Transaction [Line Items]
Agreement, ownership interest			20%
Net earned premium	91,051	76,701
Gross written commissions	23,472	21,256
Premiums receivable	$ 9,940	$ 11,334

Related Party Transactions - Re

Related Party Transactions - Resinsurance Transactions (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Related Party Transaction [Line Items]
Reinsurance premiums ceded	$ 448,737	$ 419,366
Reinsurance recoverable, net of premium payables	581,359	536,327
Everest Reinsurance Co | Reinsurance agreement | Affiliated entity
Related Party Transaction [Line Items]
Reinsurance premiums ceded	59,592	101,154
Reinsurance recoverable, net of premium payables	$ 177,455	$ 168,847

Related Party Transactions - Ar

Related Party Transactions - Arena Transactions (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Related Party Transaction [Line Items]
Fixed maturity securities, held-to-maturity:	$ 46,771	$ 47,117
Affiliated entity | Arena SOP II
Related Party Transaction [Line Items]
Fixed maturity securities, held-to-maturity:	$ 3,400

Related Party Transactions - Ot

Related Party Transactions - Other Transactions (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Professional fees and reimbursements | Affiliated entity
Related Party Transaction [Line Items]
Expenses from related party transactions	$ 3,387	$ 3,669

Commitment and Contingencies -

Commitment and Contingencies - Narrative (Details) - USD ($)	Dec. 31, 2022	Dec. 31, 2021
Commitments and Contingencies Disclosure [Abstract]
Loss contingency accrual	$ 0	$ 0

Commitment and Contingencies _2

Commitment and Contingencies - Earn-out (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Commitments and Contingencies Disclosure [Abstract]
Earn-out payments to former owners	$ 0	$ 554

Regulatory Matters (Details)

Regulatory Matters (Details) - HSIC - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
Statutory Accounting Practices [Line Items]
Statutory capital and surplus	$ 408,167	$ 369,583
RBC authorized control level	$ 110,635	$ 84,968

Statutory Accounting Principl_3

Statutory Accounting Principles - Statutory Capital and Surplus (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021
HSIC
Statutory Accounting Practices [Line Items]
Statutory capital and surplus	$ 408,167	$ 369,583
IIC
Statutory Accounting Practices [Line Items]
Statutory capital and surplus	272,413	215,508
GMIC
Statutory Accounting Practices [Line Items]
Statutory capital and surplus	259,311	209,347
OSIC
Statutory Accounting Practices [Line Items]
Statutory capital and surplus	$ 21,270	$ 21,095

Statutory Accounting Principl_4

Statutory Accounting Principles - Statutory Net Income (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
HSIC
Statutory Accounting Practices [Line Items]
Statutory net income (loss)	$ 10,860	$ 5,880
IIC
Statutory Accounting Practices [Line Items]
Statutory net income (loss)	25,394	7,315
GMIC
Statutory Accounting Practices [Line Items]
Statutory net income (loss)	14,091	(947)
BIC
Statutory Accounting Practices [Line Items]
Statutory net income (loss)	0	(67)
OSIC
Statutory Accounting Practices [Line Items]
Statutory net income (loss)	$ 173	$ 31

Subsequent Events (Details)

Subsequent Events (Details)	Jan. 18, 2023 USD ($) $ / shares shares	Jan. 13, 2023 $ / shares shares	Jan. 03, 2023 USD ($)	Jan. 12, 2023 shares	Dec. 31, 2022 $ / shares shares	Dec. 31, 2021 $ / shares shares
Subsequent Event [Line Items]
Common stock, shares authorized (in shares)					168,000,000	168,000,000
Common stock, par value (in USD per share) | $ / shares					$ 0.01	$ 0.01
Preferred stock, shares authorized (in shares)					2,000,000	2,000,000
Preferred stock, par value (in USD per share) | $ / shares					$ 0.01	$ 0.01
Preferred stock, shares outstanding (in shares)					1,969,660	1,970,124
Common shares upon conversion of preferred shares (in shares)					16,305,113
Subsequent event
Subsequent Event [Line Items]
Equity conversion ratio			4
Common stock, shares authorized (in shares)	500,000,000
Common stock, par value (in USD per share) | $ / shares	$ 0.01
Preferred stock, shares authorized (in shares)	10,000,000
Preferred stock, par value (in USD per share) | $ / shares	$ 0.01
Preferred stock, shares outstanding (in shares)	1,969,660
Common shares upon conversion of preferred shares (in shares)	16,305,113
Subsequent event | IPO
Subsequent Event [Line Items]
Sale of stock, number of shares issued (in shares)		8,952,383
Sale of stock, price per share (usd per share) | $ / shares		$ 15
Subsequent event | IPO | Skyward Specialty Insurance Group
Subsequent Event [Line Items]
Sale of stock, number of shares issued (in shares)		4,750,000
Subsequent event | IPO | Selling Stockholders
Subsequent Event [Line Items]
Sale of stock, number of shares issued (in shares)		4,202,383
Subsequent event | Over-Allotment Option
Subsequent Event [Line Items]
Sale of stock, number of shares issued (in shares)	1,342,857
Sale of stock, price per share (usd per share) | $ / shares	$ 15
Sale of stock, consideration | $	$ 62,300,000
Subsequent event | Line of Credit
Subsequent Event [Line Items]
Accordion feature, increase limit | $			$ 50,000,000
Subsequent event | Revolving Credit Facility | Line of Credit
Subsequent Event [Line Items]
Maximum borrowing capacity | $			150,000,000
Subsequent event | Letter of Credit | Line of Credit
Subsequent Event [Line Items]
Maximum borrowing capacity | $			$ 10,000,000
Subsequent event | 2022 Long-Term Incentive Plan
Subsequent Event [Line Items]
Common stock, reserved for future issuance (in shares)				3,200,516
Subsequent event | 2022 Employee Stock Purchase Plan
Subsequent Event [Line Items]
Authorized target common shares (in shares)				376,531

SEC Schedule, Article 12-15, Su

SEC Schedule, Article 12-15, Summary of Investments - Other than Investments in Related Parties (Details) $ in Thousands	Dec. 31, 2022 USD ($)
SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]
Cost	$ 1,004,350
Fair Value	948,512
Amount on Balance Sheet	953,225
Fixed maturity securities, available for sale:
SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]
Cost	662,616
Fair Value	607,572
Amount on Balance Sheet	607,572
Fixed maturity securities, available for sale: | U.S. government securities
SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]
Cost	50,416
Fair Value	48,541
Amount on Balance Sheet	48,541
Fixed maturity securities, available for sale: | Corporate securities and miscellaneous
SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]
Cost	255,116
Fair Value	235,129
Amount on Balance Sheet	235,129
Fixed maturity securities, available for sale: | Municipal securities
SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]
Cost	65,836
Fair Value	57,727
Amount on Balance Sheet	57,727
Fixed maturity securities, available for sale: | Residential mortgage-backed securities
SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]
Cost	134,844
Fair Value	119,856
Amount on Balance Sheet	119,856
Fixed maturity securities, available for sale: | Commercial mortgage-backed securities
SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]
Cost	40,129
Fair Value	36,495
Amount on Balance Sheet	36,495
Fixed maturity securities, available for sale: | Asset-backed securities
SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]
Cost	116,275
Fair Value	109,824
Amount on Balance Sheet	109,824
Fixed maturity securities, held to maturity:
SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]
Cost	52,467
Fair Value	46,771
Amount on Balance Sheet	52,467
Fixed maturity securities, held to maturity: | Asset-backed securities
SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]
Cost	52,467
Fair Value	46,771
Amount on Balance Sheet	52,467
Equity securities:
SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]
Cost	116,250
Fair Value	120,169
Amount on Balance Sheet	120,169
Equity securities: | Common stocks
SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]
Cost	50,484
Fair Value	55,996
Amount on Balance Sheet	55,996
Equity securities: | Preferred stocks
SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]
Cost	11,798
Fair Value	8,771
Amount on Balance Sheet	8,771
Equity securities: | Mutual funds
SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]
Cost	53,968
Fair Value	55,402
Amount on Balance Sheet	55,402
Mortgage loans
SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]
Cost	51,859
Fair Value	52,842
Amount on Balance Sheet	51,859
Short-term investments
SEC Schedule, 12-15, Insurance Companies, Summary of Investments, Other than Investments in Related Parties [Line Items]
Cost	121,158
Fair Value	121,158
Amount on Balance Sheet	$ 121,158

SCHEDULE II__ CONDENSED FINAN_2

SCHEDULE II — CONDENSED FINANCIAL INFORMATION OF REGISTRANT - Condensed Balance Sheet (Details) - USD ($) $ in Thousands	Dec. 31, 2022	Dec. 31, 2021	Dec. 31, 2020
Investments:
Short-term investments, at fair value	$ 121,158	$ 164,278
Total investments	1,082,367	949,359
Cash and cash equivalents	45,438	42,107
Restricted cash	79,573	65,167
Deferred income taxes	36,188	33,663
Goodwill and intangible assets, net	89,870	91,336
Other assets	82,846	90,666
Total assets	2,363,439	2,118,212
Liabilities:
Accounts payable and accrued liabilities	48,499	40,760
Notes payable	50,000	50,000
Subordinated debt, net of debt issuance costs	78,609	78,529
Total liabilities	1,941,777	1,692,132
Stockholders’ Equity:
Stockholders’ equity	421,662	426,080	$ 303,222
Total liabilities and stockholders' equity	2,363,439	2,118,212
Parent Company
Investments:
Investment in subsidiaries	503,549	517,326
Short-term investments, at fair value	25	25
Total investments	503,574	517,351
Cash and cash equivalents	8,909	5,849
Restricted cash	0	156
Deferred income taxes	19,655	15,182
Goodwill and intangible assets, net	12,641	12,641
Other assets	6,992	4,218
Total assets	551,771	555,397
Liabilities:
Accounts payable and accrued liabilities	1,500	788
Notes payable	50,000	50,000
Subordinated debt, net of debt issuance costs	78,609	78,529
Total liabilities	130,109	129,317
Stockholders’ Equity:
Stockholders’ equity	421,662	426,080
Total liabilities and stockholders' equity	$ 551,771	$ 555,397

SCHEDULE II__ CONDENSED FINAN_3

SCHEDULE II — CONDENSED FINANCIAL INFORMATION OF REGISTRANT - Condensed Statement of Operations (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Revenues:
Net investment income	$ 36,931	$ 24,646
Net investment (losses) gains	(15,705)	17,107
Total revenues	642,420	550,181
Expenses:
Interest expense	6,407	4,622
Amortization	1,547	1,520
Total expenses	592,637	501,872
Income tax benefit	10,387	9,992
Net income attributable to common shareholders	20,517	19,810
Net income attributable to participating securities	18,879	18,507
Net income	39,396	38,317
Parent Company
Revenues:
Net investment income	2,567	2,383
Net investment (losses) gains	(6)	0
Total revenues	2,561	2,383
Expenses:
Interest expense	6,407	4,621
Amortization	81	81
Total expenses	6,488	4,702
Loss before income tax expense	(3,927)	(2,319)
Income tax benefit	(1,209)	(487)
Net income attributable to common shareholders	(2,718)	(1,832)
Net income attributable to participating securities	42,114	40,149
Net income	$ 39,396	$ 38,317

SCHEDULE II__ CONDENSED FINAN_4

SCHEDULE II — CONDENSED FINANCIAL INFORMATION OF REGISTRANT - Condensed Statement of Cash Flows (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Cash flows from operating activities:
Net income	$ 39,396	$ 38,317
Net cash provided by operating activities	208,938	175,285
Cash flows from investing activities:
Net cash used in investing activities	(193,381)	(183,014)
Cash flows from financing activities:
Employee share purchases	2,180	1,380
Net cash provided by financing activities	2,180	1,380
Net increase (decrease) in cash and cash equivalents and restricted cash	17,737	(6,349)
Cash and cash equivalents and restricted cash at beginning of year	107,274	113,623
Cash and cash equivalents and restricted cash at end of year	125,011	107,274
Supplemental disclosure of cash flow information:
Cash paid for interest	5,761	4,669
Parent Company
Cash flows from operating activities:
Net income	39,396	38,317
Adjustments to reconcile net income to net cash used in operating activities	(42,672)	(40,447)
Net cash provided by operating activities	(3,276)	(2,130)
Cash flows from investing activities:
Capital contribution to subsidiaries	0	(10,000)
Distributions from investment in subsidiaries	4,000	4,000
Net cash used in investing activities	4,000	(6,000)
Cash flows from financing activities:
Employee share purchases	2,180	1,380
Net cash provided by financing activities	2,180	1,380
Net increase (decrease) in cash and cash equivalents and restricted cash	2,904	(6,750)
Cash and cash equivalents and restricted cash at beginning of year	6,005	12,755
Cash and cash equivalents and restricted cash at end of year	8,909	6,005
Supplemental disclosure of cash flow information:
Cash paid for interest	$ 5,761	$ 4,669

SCHEDULE IV__ REINSURANCE (Deta

SCHEDULE IV — REINSURANCE (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
SEC Schedule, 12-17, Insurance Companies, Reinsurance [Line Items]
Direct premiums	$ 951,121	$ 816,837
Reinsurance premiums ceded	(448,737)	(419,366)
Assumed premiums	113,610	102,352
Net earned premium	615,994	499,823
Accident & Health
SEC Schedule, 12-17, Insurance Companies, Reinsurance [Line Items]
Direct premiums	130,377	111,759
Reinsurance premiums ceded	(70,291)	(68,350)
Assumed premiums	431	387
Net earned premium	$ 60,517	$ 43,796
Percentage of amount assumed to net	0.70%	0.90%
Property & Casualty
SEC Schedule, 12-17, Insurance Companies, Reinsurance [Line Items]
Direct premiums	$ 881,862	$ 730,559
Reinsurance premiums ceded	(398,118)	(342,366)
Assumed premiums	131,282	97,154
Net earned premium	$ 615,026	$ 485,347
Percentage of amount assumed to net	21.30%	20%

SCHEDULE V__ VALUATION AND QU_2

SCHEDULE V — VALUATION AND QUALIFYING ACCOUNTS (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
Valuation Allowance For Deferred Tax Assets
SEC Schedule, 12-09, Movement in Valuation Allowances and Reserves [Roll Forward]
Balance at beginning of year	$ 586	$ 586
Charged to costs and expenses	0	0
Amounts written off	0	0
Balance at end of year	586	586
Allowance for Uncollectible Reinsurance Recoverable
SEC Schedule, 12-09, Movement in Valuation Allowances and Reserves [Roll Forward]
Balance at beginning of year	0	0
Charged to costs and expenses	0	0
Amounts written off	0	0
Balance at end of year	0	0
Allowance for Uncollectible Premiums Receivable
SEC Schedule, 12-09, Movement in Valuation Allowances and Reserves [Roll Forward]
Balance at beginning of year	261	1,146
Charged to costs and expenses	584	18
Amounts written off	(216)	(903)
Balance at end of year	$ 629	$ 261

SCHEDULE VI__ SUPPLEMENTAL IN_2

SCHEDULE VI — SUPPLEMENTAL INFORMATION CONCERNING PROPERTY-CASUALTY INSURANCE OPERATIONS (Details) - USD ($) $ in Thousands	12 Months Ended
	Dec. 31, 2022	Dec. 31, 2021
SEC Schedule, 12-18, Supplemental Information, Property-Casualty Insurance Underwriters [Abstract]
Deferred policy acquisition costs	$ 68,938	$ 59,456
Reserve for losses and loss adjustment expenses	1,141,757	979,549
Unearned premiums	442,509	363,288
Net earned premium	615,994	499,823
Net investment income	36,931	24,646
Losses and loss adjustment expenses (current year)	393,939	338,348
Losses and loss adjustment expenses (prior years)	14,385	28,000
Amortization of policy acquisition costs	65,695	47,061
Paid claims and claim adjustment expenses	300,764	249,739
Net premiums written	675,543	529,143
Ceded unearned premium	157,645	137,973
Deferred ceding commission	$ 29,849	$ 30,500