The following Management's Discussion and Analysis of financial condition and
results of operations should be read in conjunction with the Consolidated
Financial Statements, related notes and other financial information appearing
elsewhere in this Annual Report on Form 10-K, filed with the U. S. Securities
and Exchange Commission ("SEC").

Forward-Looking Statements



Certain statements contained in this Annual Report on Form 10-K, which are not
statements of historical fact, are forward-looking statements within the meaning
of Section 27A of the Securities Act of 1933, as amended, as Section 21E of the
Securities Exchange Act of 1934, as amended. Forward-looking statements give
current expectations or forecasts of future events or our future financial or
operating performance. Words such as "anticipate," "believe," "estimate,"
"expect," "will," "intend," "may," "plan," "seek" and similar terms and phrases,
or the negative thereof, may be used to identify forward-looking statements.

The forward-looking statements contained in this report are based on
management's good-faith belief and reasonable judgment based on current
information. The forward-looking statements are qualified by important factors,
risks and uncertainties, many of which are beyond our control, which could cause
our actual results to differ materially from those in the forward-looking
statements, including those described above in Item 1A Risk Factors and
subsequent reports filed with or furnished to the SEC. Any forward-looking
statement made by us in this report speaks only as of the date hereof or as of
the date specified herein. We undertake no obligation to publicly update any
forward-looking statement, whether as a result of new information, future
developments or otherwise, except as may be required by any applicable laws or
regulations.

Recent Developments

COVID-19

COVID-19 (the "Pandemic") caused significant disruption to public health, the
global economy, financial markets, and commercial, social and community activity
in general. As there has been a significant reduction in reported cases and
correspondingly a reduction in government restrictions, we see reduced risk to
our business. We continue to monitor potential risks the Pandemic may present
including a potential resurgence. Our exposure to the Pandemic is manifold. The
majority of our employees continue to work remotely however strict
"shelter-in-place" or "stay-at-home" orders have been lifted. A significant
portion of our revenues are generated from the hospitality sector within the
U.S. which remains under stress due to the threats of resurgence and resource
shortages that resulted from the Pandemic.

We have continued to provide customer service, process new and renewal business,
handle claims and otherwise manage all operations even though the vast majority
of the staff is working remotely. To date, we have not seen a major disruption
in our business as a result of the Pandemic and currently do not expect to see a
material negative impact to our financial position or results of operations as a
result of the Pandemic.

VSRM Transaction

Prior to October 13, 2022, Sycamore owned 50% of Venture Agency Holdings, Inc.
("Venture") and has accounted for its ownership under the equity method of
accounting. On October 13, 2022, Sycamore purchased the other 50% of Venture
from an individual for $9.7 million. Following this purchase, Sycamore owned
100% of Venture, which was then renamed to VSRM, Inc. ("VSRM"). VRSM and its two
wholly owned subsidiaries, The Roots Insurance Agency, Inc. ("Roots") and Mitzel
Insurance Agency, Inc. ("Mitzel") were incorporated into the Company's
consolidated financial statements as of the date of the acquisition.

The Company recognized Sycamore's purchase of the individual's shares of VSRM as
a step acquisition and revalued all assets and liabilities upon the acquisition
date. This resulted in the recognition of an $8.8 million non-operating gain
reported in the Consolidated Statements of Operations as Gain from VSRM
Transaction in the fourth quarter of 2022. The Company also utilized $12.5
million of federal tax net operating losses carried forward and $14.8 million
state tax net operating losses

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carried forward, for a net-of-tax benefit of $9.4 million. VSRM retained $8.9
million of debt, and $9.4 million of tax liabilities, as well as other smaller
assets and liabilities that did not go with the transaction.

The fair value of the equity interest of VSRM immediately prior to the
acquisition by Sycamore was $10.1 million. The fair value techniques used to
measure the fair value of VSRM included using the carrying value of all current
assets and liabilities as their carrying values approximated their fair values.
Intangible assets were reviewed based on recent valuations performed by third
party valuation experts and the net realized proceeds received upon the sale of
the Security & Alarm Business sold the following day.

On October 14, 2022, VSRM sold all of its security guard and alarm installation
insurance brokerage business (the "Security & Alarm Business") to a third party
insurance brokerage firm for $38.2 million. As part of the transaction, the
individual who previously owned 50% of VSRM transitioned employment to the
buyer, along with a team of approximately eight other employees of VSRM. The
Company recognized this transaction as the sale of a business. Because all
assets and liabilities were just adjusted to fair value from the step
acquisition described above, the basis of the net assets sold equaled the net
proceeds from the sale, thus there was no gain recognized upon the sale of the
Security & Alarm Business.

On December 30, 2022, VSRM contributed its remaining business, including its two
wholly owned subsidiaries (Mitzel and Roots) to a new wholly owned subsidiary,
Sycamore Specialty Underwriters, LLC ("SSU"). The business contributed to SSU
consisted of customer accounts of substantially all of the personal lines
business and a small subset of the commercial lines business underwritten by the
Insurance Company Subsidiaries, and all of the customer accounts VSRM produced
for third-party insurers, other than the security guard and alarm installation
brokerage business previously sold.

On December 31, 2022, Andrew D. Petcoff purchased 50% of SSU from VSRM, Inc. for
$1,000. As a result, SSU and its two wholly owned subsidiaries, Roots and
Mitzel, are no longer consolidated in the Company's consolidated financial
statements as of December 31, 2022, and VSRM's investment in SSU is accounted
for using the equity method. The net assets transferred to SSU had a fair value
of $0 at the time of the contribution. There was no gain or loss recognized upon
the sale of half of SSU to Mr. Petcoff. Included in the net assets transferred
to SSU was a $1.0 million promissory note payable, a liability that was assumed
by SSU. The note payable was an obligation that originated as part of the
Venture Transaction described below, and is payable to CIC.

In order to determine the value of the portion of the business contributed to SSU, the Company obtained a third party valuation based on a weighting of discounted cash flows and earnings before interest, taxes, depreciation and amortization (EBITDA) multiple valuation methods. The valuation included significant estimates and assumptions related to (i) forecasted revenue and EBITDA and (ii) the selection of the EBITDA multiple and discount rate.

Sale of Certain Agency Business



On June 30, 2021, Sycamore sold to Venture Agency Holdings, Inc., a related
party, the customer accounts and other related assets of some of its personal
and commercial lines of business (the "Venture Transaction"). Sycamore will
continue to produce various personal and commercial lines that it did not sell
which is substantially all produced for, and underwritten by, our Insurance
Company Subsidiaries. We recognized an $8.9 million gain on the sale which is
reflected in Other Gains in the Consolidated Statement of Operations. In order
to determine the value of the portion of the business sold, the Company obtained
a third party valuation based on a weighting of discounted cash flows and
earnings before interest, taxes, depreciation and amortization (EBITDA) multiple
valuation methods. The valuation included significant estimates and assumptions
related to (i) forecasted revenue and EBITDA and (ii) the selection of the
EBITDA multiple and discount rate.

The purchase price was $10.0 million of which $1.0 million was paid in cash on
June 30, 2021, and $9.0 million was in the form of two promissory notes (one for
$6.0 million and one for $3.0 million). Both notes require interest-only
quarterly payments at a per annum rate of 7.0%, with a five-year maturity. There
are no prepayment penalties. On December 14, 2021, Venture paid off the $3.0
million note. On October 20, 2022, Venture paid down $5.0 million of the $6.0
million note.

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The remaining $1.0 million promissory note was assumed by SSU as part of the contribution of business to SSU described above.



The assets sold included the customer accounts (mainly agency-related new and
renewal rights) of substantially all of the personal lines business and a small
subset of the commercial lines business underwritten by our Insurance Company
Subsidiaries, and all of the customer accounts Sycamore produced for third-party
insurers. The Venture Transaction included the transition of 21 employees from
Conifer to Venture as well as necessary systems and office functions to operate
the business. Venture did not assume any in-force business or liabilities. The
business transitioned to Venture as it produced new or renewal business
effective July 1, 2021. Our Insurance Company Subsidiaries continued to
underwrite substantially all of the business we sold to Venture that we
underwrote prior to the transaction.

Loss Portfolio Transfer



On November 1, 2022, the Company entered into a loss portfolio transfer ("LPT")
reinsurance agreement with Fleming Reinsurance Ltd ("Fleming Re"). Under the
agreement, Fleming Re will cover an aggregate limit of $66.3 million of paid
losses on $40.8 million of stated net reserves as of June 30, 2022, relating to
accident years 2019 and prior. This covers substantially all of the commercial
liability lines underwritten by the Company. Within the aggregate limit, there
is a $5.5 million loss corridor in which the Company retains losses in excess of
$40.8 million. Fleming Re is then responsible to cover paid losses in excess of
$46.3 million up to $66.3 million. Accordingly, there is $20.0 million of
adverse development cover for accident years 2019 and prior. Under the
agreement, Fleming Re was paid $40.8 million for stated net reserves as of June
30, 2022, plus a one-time risk fee of $5.4 million. Recoverables due to the
Company under this agreement are recorded as reinsurance recoverables. The
agreement is between CIC and WPIC and Fleming Re. As of December 31, 2022, the
Company has recorded losses through the $5.5 million corridor and $644,000 into
the $20.0 million layer.

The Company paid $25.0 million in cash on October 14, 2022, which was netted down for claims paid through September 30, 2022 and $13.6 million of funds withheld. Cash used in the transaction was generated from the existing investment portfolios held by CIC and WPIC.

A.M. Best



On April 21, 2022, A.M. Best downgraded the Company's Long-Term Issuer Credit
Rating (Long-Term ICR) from "bb" (Fair) to "bb-" (Fair), and downgraded the
Company's insurance subsidiaries Financial Strength Rating from "B++" (Good) to
"B+" (Good) and the Long-Term ICR from "bbb" (Good) to "bbb-" (Good). The
outlook assigned to all these ratings by A.M. Best was Stable. We do not believe
the rating changes will have a material effect on our business.

Business Overview



We are an insurance holding company that markets and services our product
offerings through specialty commercial and specialty personal insurance business
lines. Our growth has been significant since our founding in 2009. Currently, we
are authorized to write insurance as an excess and surplus lines carrier in 45
states, including the District of Columbia. We are licensed to write insurance
as an admitted carrier in 42 states, including the District of Columbia, and we
offer our insurance products in all 50 states.

Our revenues are primarily derived from premiums earned from our insurance operations. We also generate other revenues through investment income and other income which mainly consists of: installment fees and policy issuance fees generally related to the policies we write.



Our expenses consist primarily of losses and loss adjustment expenses, agents'
commissions, and other underwriting and administrative expenses. We organize our
operations in three insurance businesses: commercial insurance lines, personal
lines, and agency business. Together, the commercial and personal lines refer to
"underwriting" operations that take insurance risk, and the agency business
refers to non-risk insurance business.

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Through our commercial insurance lines, we offer coverage for both commercial property and commercial liability. We also offer coverage for commercial automobiles and workers' compensation. Our insurance policies are sold to targeted small and mid-sized businesses on a single or multiple-coverage basis.



Through our personal insurance lines, we offer homeowners insurance and dwelling
fire insurance products to individuals in several states. Our specialty
homeowners insurance product line is primarily comprised of low-value dwelling
insurance tailored for owners of lower valued homes, which we offer in Illinois,
Indiana and Texas.

Through our wholesale agency business segment, we offer commercial and personal
lines insurance products for our Insurance Company Subsidiaries as well as
third-party insurers. The wholesale agency business segment provides our agents
with more insurance product options. However, as a result of the sale of certain
agency business on June 30, 2021, going forward, our agency segment will not be
producing any significant amounts of business for third party insurers and will
produce approximately 50% less business for the Insurance Company Subsidiaries.

Critical Accounting Policies and Estimates

General



We identified the accounting estimates below as critical to the understanding of
our financial position and results of operations. Critical accounting estimates
are defined as those estimates that are both important to the portrayal of our
financial condition and results of operations and which require us to exercise
significant judgment. We use significant judgment concerning future results and
developments in applying these critical accounting estimates and in preparing
our consolidated financial statements. These judgments and estimates affect the
reported amounts of assets, liabilities, revenues and expenses and the
disclosure of material contingent assets and liabilities. Actual results may
differ materially from the estimates and assumptions used in preparing the
consolidated financial statements. We evaluate our estimates regularly using
information that we believe to be relevant. See the Consolidated Financial
Statements Note 1 ~ Summary of Significant Accounting Policies, for further
details.

Unpaid Loss and Loss Adjustment Expense Reserves



Our recorded loss and loss adjustment expenses ("LAE") reserves represent
management's best estimate of unpaid loss and LAE at each balance sheet date,
based on information, facts and circumstances known at such time. Our loss and
LAE reserves reflect our estimates at the balance sheet date of:

Case reserves, which are unpaid loss and LAE amounts that have been reported; and

Incurred but not reported ("IBNR") reserves, which are (1) unpaid loss and LAE amounts that have been incurred but not yet reported; and (2) the expected development on case reserves.

We do not discount the loss and LAE reserves for the time value of money.



Case reserves are initially set by our claims personnel. When a claim is
reported to us, our claims department completes a case­basis valuation and
establishes a case reserve for the estimated amount of the probable ultimate
losses and LAE associated with that claim. Our claims department updates their
case­basis valuations upon receipt of additional information and reduces case
reserves as claims are paid. The case reserve is based primarily upon an
evaluation of the following factors:

The type of loss;

The severity of injury or damage;

Our knowledge of the circumstances surrounding the claim;

The jurisdiction of the occurrence;

Policy provisions related to the claim;


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Expenses intended to cover the ultimate cost of settling claims, including investigation and defense of lawsuits resulting from such claims, costs of outside adjusters and experts, and all other expenses which are identified to the case; and

Any other information considered pertinent to estimating the indemnity and expense exposure presented by the claim.



IBNR reserves are determined by subtracting case reserves and paid loss and LAE
from the estimated ultimate loss and LAE. Our actuarial department develops
estimated ultimate loss and LAE on a quarterly basis. Our Reserve Review
Committee (which includes our Chief Executive Officer, President, Chief
Financial Officer, other members of executive management, and key actuarial,
underwriting and claims personnel) meets each quarter to review our actuaries'
estimated ultimate expected loss and LAE.

We use several generally accepted actuarial methods to develop estimated
ultimate loss and LAE estimates by line of business and accident year. This
process relies on the basic assumption that past experience, adjusted for the
effects of current developments and likely trends, is a reasonable basis for
predicting future outcomes. These methods utilize various inputs, including:

•
Written and earned premiums;

•

Paid and reported losses and LAE;

Expected initial loss and LAE ratio, which is the ratio of incurred losses and LAE to earned premiums; and

Expected claim reporting and payout patterns based on our own loss experience and supplemented with insurance industry data where applicable.

The principal standard actuarial methods used by our actuaries for their comprehensive reviews include:


Loss ratio method-This method uses loss and LAE ratios for prior accident years,
adjusted for current trends, to determine an appropriate expected loss and LAE
ratio for a given accident year;


Loss development methods-Loss development methods assume that the losses and LAE
yet to emerge for an accident year are proportional to the paid or reported loss
and LAE amounts observed to­date. The paid loss development method uses losses
and LAE paid to date, while the reported loss development method uses losses and
LAE reported to date;


Bornheutter­Ferguson method-This method is a combination of the loss ratio and
loss development methods, where the loss development factor is given more weight
as an accident year matures; and

Frequency/severity method-This method projects claim counts and average cost per claim on a paid or reported basis for high frequency, low severity products.



Our actuaries give different weights to each of these methods based upon the
amount of historical experience data by line of business and by accident year,
and based on judgment as to what method is believed to result in the most
accurate estimate. The application of each method by line of business and by
accident year may change in the future if it is determined that a different
emphasis for each method would result in more accurate estimates.

Our actuaries also analyze several diagnostic measures by line of business and
accident year, including but not limited to: reported and closed frequency and
severity, claim reporting and claim closing patterns, paid and incurred loss
ratio development, and ratios of paid loss and LAE to incurred loss and LAE.
After the actuarial methods and diagnostic measures have been performed and
analyzed, our actuaries use their judgment and expertise to select an estimated
ultimate loss and LAE by line of business and by accident year.

Our actuaries estimate an IBNR reserve for our unallocated LAE not specifically
identified to a particular claim, namely our internal claims department salaries
and associated general overhead and administrative expenses associated with the
adjustment and processing of claims. These estimates, which are referred to as
unallocated loss adjustment expense

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("ULAE") reserves, are based on internal cost studies and analyses reflecting
the relationship of ULAE paid to actual paid and incurred losses. We select
factors that are applied to case reserves and IBNR reserve estimates in order to
estimate the amount of ULAE reserves applicable to estimated loss reserves at
the balance sheet date.

We allocate the applicable portion of our estimated loss and LAE reserves to
amounts recoverable from reinsurers under reinsurance contracts and report those
amounts separately from our loss and LAE reserves as an asset on our balance
sheet.

The estimation of ultimate liability for losses and LAE is a complex, imprecise
and inherently uncertain process, and therefore involves a considerable degree
of judgment and expertise. Our loss and LAE reserves do not represent an exact
measurement of liability, but are estimates based upon various factors,
including but not limited to:

Actuarial projections of what we, at a given time, expect to be the cost of the ultimate settlement and administration of claims reflecting facts and circumstances then known;

Estimates of future trends in claims severity and frequency;

Assessment of asserted theories of liability; and

Analysis of other factors, such as variables in claims handling procedures, economic factors, and judicial and legislative trends and actions.



Most or all of these factors are not directly or precisely quantifiable,
particularly on a prospective basis, and are subject to a significant degree of
variability over time. In addition, the establishment of loss and LAE reserves
makes no provision for the broadening of coverage by legislative action or
judicial interpretation or for the extraordinary future emergence of new types
of losses not sufficiently represented in our historical experience or which
cannot yet be quantified. As a result, an integral component of our loss and LAE
reserving process is the use of informed subjective estimates and judgments
about our ultimate exposure to losses and LAE. Accordingly, the ultimate
liability may vary significantly from the current estimate. The effects of
change in the estimated loss and LAE reserves are included in the results of
operations in the period in which the estimate is revised.

Our reserves consist entirely of reserves for property and liability losses,
consistent with the coverages provided for in the insurance policies directly
written or assumed by us under reinsurance contracts. Several years may elapse
between the occurrence of an insured loss, the reporting of the loss to us and
our payment of the loss. The level of IBNR reserves in relation to total
reserves depends upon the characteristics of the specific line of business,
particularly related to the speed with which claims are reported and outstanding
claims are paid. Lines of business for which claims are reported slowly will
have a higher percentage of IBNR reserves than lines of business that report and
settle claims more quickly.

The following table shows the ratio of IBNR reserves to total reserves net of reinsurance recoverables as of December 31, 2022 (dollars in thousands):


                                                            Ratio of
                                                            IBNR to
                   Case          IBNR          Total         Total
Line of Business Reserves      Reserves      Reserves       Reserves
Commercial Lines $  36,354     $  41,903     $  78,257           53.5 %
Personal Lines       2,944         1,687         4,631           36.4 %
Total Lines      $  39,298     $  43,590     $  82,888           52.6 %



Included in the reinsurance recoverables were reinsurance recoverables from the
LPT which were $24.4 million of reinsurance recoverables on case reserves and
$1.5 million of reinsurance recoverables on IBNR. All of the reinsurance
recoverables from the LPT are included in commercial lines.

Although we believe that our reserve estimates are reasonable, it is possible
that our actual loss and LAE experience may not conform to our assumptions and
may, in fact, vary significantly from our assumptions. Accordingly, the ultimate
settlement of losses and the related LAE may vary significantly from the
estimates included in our financial statements. We continually review our
estimates and adjust them as we believe appropriate as our experience develops
or new information becomes known to us. Such adjustments are included in current
operations.

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Our loss and LAE reserves do not represent an exact measurement of liability,
but are estimates. The most significant assumptions affecting our IBNR reserve
estimates are the loss development factors applied to paid losses and case
reserves to develop IBNR by line of business and accident year. Although
historical loss development provides us with an indication of future loss
development, it typically varies from year to year. Thus, for each accident year
within each line of business we select one loss development factor out of a
range of historical factors.

We generated a sensitivity analysis of our net reserves which represents
reasonably likely levels of variability in our selected loss development
factors. We believe the most meaningful approach to the sensitivity analysis is
to vary the loss development factors that drive the ultimate loss and LAE
estimates. We applied this approach on an accident year basis, reflecting the
reasonably likely differences in variability by level of maturity of the
underlying loss experience for each accident year. Generally, the most recent
accident years are characterized by more unreported losses and less information
available for settling claims, and have more inherent uncertainty than the
reserve estimates for more mature accident years. Therefore, we used variability
factors of plus or minus 10% for the most recent accident year, 5% for the
preceding accident year, and 2.5% for the second preceding accident year. There
is minimal expected variability for accident years at four or more years'
maturity.

The following table displays ultimate net loss and LAE and net loss and LAE
reserves by accident year for the year ended December 31, 2022. We applied the
sensitivity factors to each accident year amount and have calculated the amount
of potential net loss and LAE reserve change and the impact on 2022 reported
pre-tax income and on net income and shareholders' equity at December 31, 2022.
We believe it is not appropriate to sum the illustrated amounts as it is not
reasonably likely that each accident year's reserve estimate assumptions will
vary simultaneously in the same direction to the full extent of the sensitivity
factor. The shareholders' equity amounts include an income tax rate assumption
of 21%, however due to the net operating losses ("NOL") available to use against
taxable income and the offsetting valuation allowance, there is no difference
between pre-tax income and shareholders' equity in this schedule. The dollar
amounts in the table are in thousands.


                                         As of December 31,
                                                2022                                                     Impact
                                                                          Ultimate
                                                                          Loss and
                                   Net Ultimate       Net Loss and           LAE
                                     Loss and             LAE            Sensitivity            Pre-            Shareholders'
                                     LAE (1)          Reserves (1)         Factor          Tax Income (2)        Equity (2)
Increased Ultimate Losses & LAE
Accident Year 2022                $       57,136     $       36,262              10.0 %    $        (5,714 )   $        (4,514 )
Accident Year 2021                        52,152             22,840               5.0 %             (2,608 )            (2,060 )
Accident Year 2020                        46,128             16,142               2.5 %             (1,153 )              (911 )
Prior to 2020 Accident Years                   -              7,645                 - %                  -                   -

Decreased Ultimate Losses & LAE
Accident Year 2022                        57,136             36,262             (10.0 )%             5,714               4,514
Accident Year 2021                        52,152             22,840              (5.0 )%             2,608               2,060
Accident Year 2020                        46,128             16,142              (2.5 )%             1,153                 911
Prior to 2020 Accident Years                   -              7,645                 - %                  -                   -



(1) Represents amounts as of December 31, 2022.
(2) Represents how pre-tax income and shareholders' equity would change if the
Net Ultimate Loss and LAE were to change by the percentage in the Ultimate Loss
and LAE Sensitivity Factor column.

Investment Valuation and Impairment



We carry debt securities classified as available­for­sale at fair value, and
unrealized gains and losses on such securities, net of any deferred taxes, are
reported as a separate component of accumulated other comprehensive income. Our
equity securities that do not result in consolidation and are not accounted for
under the equity method are measured at fair value and any changes in fair value
are recognized in net income. We carry other equity investments that do not have
a readily

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determinable fair value at cost, less impairment and adjusted for observable
price changes under the measurement alternative provided under GAAP. We review
these investments for impairment during each reporting period. We do not have
any securities classified as trading or held to maturity.

We evaluate our available­for­sale investments regularly to determine whether
there have been declines in value that are other­than­temporary. Our outside
investment managers assist us in this evaluation. When we determine that a
security has experienced an other­than­temporary impairment, the impairment loss
is recognized as a realized investment loss.

We consider a number of factors in assessing whether an impairment is
other­than­temporary, including (1) the amount and percentage that current fair
value is below cost or amortized cost, (2) the length of time that the fair
value has been below cost or amortized cost and (3) recent corporate
developments or other factors that may impact an issuer's near term prospects.
In addition, for debt securities, we consider the credit quality ratings for the
securities, with a special emphasis on securities downgraded to below investment
grade. We also consider our intent to sell available­for­sale debt securities in
an unrealized loss position, and if it is more likely than not that we will be
required to sell these securities before a recovery in fair value to their cost
or amortized cost basis.

Fair values are measured in accordance with ASC 820, Fair Value Measurements.
The guidance establishes a framework for measuring fair value and a three­level
hierarchy based upon the quality of inputs used to measure fair value. The three
levels of the fair value hierarchy are: (1) Level 1: inputs are based on quoted
prices (unadjusted) in active markets for identical assets or liabilities, (2)
Level 2: inputs are other than quoted prices that are observable for the asset
or liabilities, either directly or indirectly, for substantially the full term
of the asset or liability and (3) Level 3: unobservable inputs that are
supported by little or no market activity. The unobservable inputs represent the
Company's best assumption of how market participants would price the assets or
liabilities. The Company also has investment company limited partnership
investments, which are measured at net asset value (NAV). The fair value of
these investments is based on the capital account balances reported by the
investment funds subject to their management review and adjustment. The capital
account balances reflect the fair value of the investment funds.

The fair values of debt and equity securities have been determined using fair
value prices provided by our investment managers, who utilize internationally
recognized independent pricing services. The prices provided by the independent
pricing services are generally based on observable market data in active markets
(e.g., broker quotes and prices observed for comparable securities).

The values for publicly­traded equity securities are generally based on Level 1
inputs which use the market approach valuation technique. The values for debt
securities generally incorporate significant Level 2 inputs. The carrying value
of cash and short­term investments approximate their fair values due to their
short­term maturity.

We review fair value prices provided by our outside investment managers for
reasonableness by comparing the fair values provided by the managers to those
provided by our investment custodian. We also review and monitor changes in
unrealized gains and losses. We obtain an understanding of the methods, models
and inputs used by our investment managers and independent pricing services, and
controls are in place to validate that prices provided represent fair values.
Our control process includes initial and ongoing evaluation of the methodologies
used, a review of specific securities and an assessment for proper
classification within the fair value hierarchy.

Income Taxes



As of December 31, 2022, we have federal and state income tax NOL carryforwards
of $65.6 million and $107.2 million, respectively. Of the NOL carryforwards,
$50.4 million will expire in tax years 2030 through 2042 and $15.2 million will
never expire. Of the federal NOL amount, $7.6 million are subject to limitations
under Section 382 of the Internal Revenue Code. These net NOL carryforwards are
limited in the amount that can be utilized in any one year and may expire before
they are realized. At this time we do not expect that any of the remaining NOL
carryforwards will expire before utilized.

A valuation allowance of $21.7 million and $14.6 million has been recorded
against the gross deferred tax assets as of December 31, 2022 and 2021,
respectively, as the Company has recognized a three-year cumulative loss as of
December 31, 2022 which is significant negative evidence to support the lack of
recoverability of those deferred tax assets in accordance

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with ASC 740, Income Taxes. If the $21.7 million valuation allowance as of
December 31, 2022 were reversed in the future, it would increase book value by
$1.77 per share. The net deferred tax assets were zero as of December 31, 2022
and 2021.

If, in the future, we determine we can support the recoverability of a portion
or all of the deferred tax assets under the guidance, the tax benefits relating
to any reversal of the valuation allowance on deferred tax assets will be
accounted for as a reduction of income tax expense and result in an increase in
equity. Changes in tax laws and rates may affect recorded deferred tax assets
and liabilities and our effective tax rate in the future.

Non-GAAP Financial Measures

Adjusted Operating Income (Loss) and Adjusted Operating Income (Loss) Per Share



Adjusted operating income (loss) and adjusted operating income (loss) per share
are non-GAAP measures that represent net income allocable to common shareholders
excluding net realized investment gains and losses, net of tax, change in fair
value of equity securities, net of tax, the gain from VSRM Transaction, net of
tax, the loss portfolio transfer risk fee, net of tax, and other gains and
losses, net of tax. The most directly comparable financial GAAP measures to
adjusted operating income and adjusted operating income per share are net income
and net income per share, respectively. Adjusted operating income and adjusted
operating income per share are intended as supplemental information and are not
meant to replace net income or net income per share. Adjusted operating income
and adjusted operating income per share should be read in conjunction with the
GAAP financial results. Our definition of adjusted operating income may be
different from that used by other companies. The following is a reconciliation
of net income to adjusted operating income (dollars in thousands), as well as
net income per share to adjusted operating income per share:
                                                      For the Years Ended December 31,
                                                    2022            2021            2020
Net income (loss)                               $    (10,681 )   $    (1,094 )   $       595
Less:
Net realized investment gains (losses), net
of tax                                                (1,505 )         2,878           8,126
Change in fair value of equity securities,
net of tax                                               403          (2,020 )           228
Gain from VSRM Transaction, net of tax                 8,810               -               -
Loss portfolio transfer risk fee, net of tax          (5,400 )             -               -
Other gains (losses), net of tax                          59          11,664             260
Adjusted operating income (loss)                $    (13,048 )   $   

(13,616 ) $ (8,019 )



Weighted average common shares, diluted           10,692,090       

9,691,998 9,625,059



Diluted income (loss) per common share:
Net income (loss)                               $      (1.00 )   $     (0.11 )   $      0.06
Less:
Net realized investment gains (losses), net
of tax                                                 (0.14 )          0.30            0.84
Change in fair value of equity securities,
net of tax                                              0.04           (0.21 )          0.02
Gain from VSRM Transaction, net of tax                  0.82               -               -
Loss portfolio transfer risk fee, net of tax           (0.51 )             -               -
Other gains (losses), net of tax                        0.01            1.20            0.03

Adjusted operating income (loss) per share $ (1.22 ) $ (1.40 ) $ (0.83 )





We use adjusted operating income and adjusted operating income per share, in
conjunction with other financial measures, to assess our performance and to
evaluate the results of our business. We believe these measures provide
investors with valuable information relating to our ongoing performance that may
be obscured by the effect of investment gains and losses as a result of our
market risk sensitive instruments, which primarily relate to fixed income
securities that are available-for-sale and not held for trading purposes.
Realized investment gains and losses may vary significantly between periods and
are generally driven by external economic developments, such as capital market
conditions. Accordingly, adjusted operating income excludes the effect of items
that tend to be highly variable from period to period and highlights the results
from our ongoing business operations and the underlying loss or profitability of
our business. We believe that it is useful for investors to evaluate adjusted
operating income and adjusted operating income per share, along with net income
and net income per share, when reviewing and evaluating our performance.

                                       44
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Executive Overview



The Company's gross written premiums increased $5.9 million, or 4.5%, to $138.0
million in 2022, compared to $132.1 million in 2021. This was due to a
substantial increase in gross written premiums in our personal lines of
business, specifically low-value dwelling. This increase was primarily due to
additional exposures and increased rates. Our personal lines gross written
premium increased $6.1 million, or 40.8%, to $21.1 million in 2022, compared to
$15.0 million in 2021.

The Company reported a net loss of $10.7 million, or $1.00 per share, in 2022, compared to a net loss of $1.1 million, or $0.11 per share, in 2021.



Adjusted operating loss, a non-GAAP measure, was $13.0 million, or $1.22 per
share, for the year ended December 31, 2022, compared to an adjusted operating
loss of $13.6 million, or $1.40 per share, for the year ended December 31, 2021.

The 2022 results included an $8.8 million non-operating gain in the fourth
quarter of 2022 from the step acquisition of VSRM and subsequent sale of its
security guard and alarm installation insurance brokerage business to a third
party insurance brokerage firm. The Company also recorded a tax benefit of $9.4
million from the utilization of net operating loss tax carryforwards ("NOLs")
applied against the taxable gain on the transaction. The deferred tax assets
associated with the NOLs had a valuation allowance against it, and thus there
was the recognition of the benefit in the period it was used.

The Company entered into a loss portfolio transfer reinsurance agreement on
November 1, 2022 with Fleming Re in order to reduce its exposure to future
unfavorable development on its reserves. The Company was charged a one-time risk
fee of $5.4 million, which was reflected as a non-operating loss. Fleming Re
will cover an aggregate limit of $66.3 million of paid losses on $40.8 million
of stated net reserves as of June 30, 2022, relating to accident years 2019 and
prior. Within the aggregate limit, there is a $5.5 million loss corridor in
which the Company retains losses in excess of $40.8 million. Fleming Re is then
responsible to cover paid losses in excess of $46.3 million up to $66.3 million.
As of December 31, 2022, the Company has recorded losses through the $5.5
million corridor and $644,000 into the $20.0 million layer.

In the fourth quarter of 2022, the Company incurred $2.0 million of losses and $1.6 million reinsurance reinstatement costs related to Hurricane Ian.



The 2021 results included an $8.9 million gain from the June 30, 2021 Venture
Transaction, and a $2.8 million gain from the forgiveness of the PPP loan. Both
gains are reflected in Other Gains on the Consolidated Statements of Operations.
We also saw continued improvement in our current accident year underwriting
results as our mix of business and other underwriting changes helped to produce
a 2021 accident year combined ratio of 93.3%. These positive results were offset
by $19.4 million of adverse development from prior accident years.

The Company experienced $2.0 million of catastrophe losses, net of reinsurance recoverables, during 2021 from Winter Storm Uri. The Company had $86,000 of reinsurance reinstatement costs relating to Hurricane Irma in 2021.


                                       45
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Results of Operations - 2022 Compared to 2021



The following table summarizes our operating results for the years indicated
(dollars in thousands):

                           Summary Operating Results

                                         Years Ended December 31,
                                          2022               2021        $ Change       % Change
Gross written premiums                $     138,019       $  132,095     $   5,924            4.5 %

Net written premiums                  $      91,232       $  101,429     $ (10,197 )        (10.1 %)

Net earned premiums                   $      96,711       $   98,802     $  (2,091 )         (2.1 %)
Other income                                  2,768            2,671            97            3.6 %
Losses and loss adjustment
expenses, net                                81,440           69,861        11,579           16.6 %
Policy acquisition costs                     22,179           28,451        (6,272 )        (22.0 %)
Operating expenses                           18,789           16,509         2,280           13.8 %
Loss portfolio transfer risk fee              5,400                -         5,400              *
Underwriting gain (loss)                    (28,329 )        (13,348 )     (14,981 )       (112.2 %)
Net investment income                         3,043            1,968         1,075           54.6 %
Net realized investment gains
(losses)                                     (1,505 )          2,878        (4,383 )            *
Change in fair value of equity
securities                                      403           (2,020 )       2,423              *
Gain from VSRM Transaction                    8,810                -         8,810              *
Other gains (losses)                             59           11,664       (11,605 )            *
Interest expense                              2,971            2,852           119            4.2 %
Income (loss) before income taxes           (20,490 )         (1,710 )     (18,780 )            *
Equity earnings in Affiliate, net
of tax                                          368              824          (456 )        (55.3 %)
Income tax expense                           (9,441 )            208        (9,649 )            *
Net income (loss)                     $     (10,681 )     $   (1,094 )   $  (9,587 )            *
Underwriting Ratios:
Loss ratio (1)                                 83.9 %           70.5 %
Expense ratio (2)                              38.4 %           42.4 %
Combined ratio (3)                            122.3 %          112.9 %




(1)
The loss ratio is the ratio, expressed as a percentage, of net losses and loss
adjustment expenses to net earned premiums and other income from underwriting
operations.

(2)

The expense ratio is the ratio, expressed as a percentage, of policy acquisition costs and operating expenses to net earned premiums and other income from underwriting operations.

(3)

The combined ratio is the sum of the loss ratio and the expense ratio. A combined ratio under 100% indicates an underwriting profit. A combined ratio over 100% indicates an underwriting loss.

* Percentage change is not meaningful

Premiums



Premiums are earned ratably over the term of the policy, whereas written
premiums are reflected on the effective date of the policy. Almost all
commercial lines and homeowners products have annual policies, under which
premiums are earned evenly over one year. The resulting net earned premiums are
impacted by the gross and ceded written premiums, earned ratably over the terms
of the policies.

                                       46
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Our premiums are presented below for the years ended December 31, 2022 and 2021
(dollars in thousands):

                           Summary of Premium Revenue

                           Years Ended December 31,
                             2022              2021        $ Change       % Change
Gross written premiums
Commercial lines         $     116,868       $ 117,075     $    (207 )         (0.2 %)
Personal lines                  21,151          15,020         6,131           40.8 %
Total                    $     138,019       $ 132,095     $   5,924            4.5 %

Net written premiums
Commercial lines         $      72,318       $  87,307     $ (14,989 )        (17.2 %)
Personal lines                  18,914          14,122         4,792           33.9 %
Total                    $      91,232       $ 101,429     $ (10,197 )        (10.1 %)

Net Earned premiums
Commercial lines         $      80,823       $  87,759     $  (6,936 )         (7.9 %)
Personal lines                  15,888          11,043         4,845           43.9 %
Total                    $      96,711       $  98,802     $  (2,091 )         (2.1 %)



Gross written premiums increased by $5.9 million, or 4.5%, to $138.0 million,
for the year ended December 31, 2022, compared to $132.1 million for the year
ended December 31, 2021. The increase was attributable to an increase in written
premium in our small business and low-value dwelling programs, which was offset
by a decrease in written premium in our hospitality programs. Increases in the
personal lines business was primarily attributable to an increase in policies,
but also due to increases in rates.

Commercial lines gross written premiums decreased $207,000, or 0.2%, to $116.9
million, for the year ended December 31, 2022, compared to $117.1 million for
the year ended December 31, 2021. Gross written premiums for our small business
programs increased by $4.5 million, or 5.3%, to $89.9 million, for the year
ended December 31, 2022, compared to $85.4 million for the year ended December
31, 2021. This increase was offset by our hospitality programs gross written
premiums, which decreased by $4.7 million, or 14.9%, to $27.0 million, for the
year ended December 31, 2022, compared to $31.7 million for the year ended
December 31, 2021.

Personal lines gross written premiums increased $6.1 million, or 40.8%, to $21.1
million, for the year ended December 31, 2022, compared to $15.0 million for the
year ended December 31, 2021. This increase was largely driven by our low-value
dwelling business.

Net written premiums decreased $10.2 million, or 10.1%, to $91.2 million, for
the year ended December 31, 2022, compared to $101.4 million for the year ended
December 31, 2021. The Company entered into new specific loss reinsurance
treaties on December 31, 2021 and January 1, 2022, which included a 40% ceding
commission. This increased ceded written premiums by approximately $11.4 million
in 2022. There was no ceding commission on excess of loss treaties during 2021.
Ceded earned premiums also increased due to the new treaties by $8.9 million.
The increase in ceded earned premiums was offset by the same increase in ceding
commissions, which reduced acquisition costs.

Other Income



Other income consists primarily of fees charged to policyholders by the Company
for services outside of the premium charge, such as installment billings and
policy issuance costs. Other income also includes the interest income from the
$6.0 million and $3.0 million promissory notes relating to the Venture
Transaction. The $3.0 million promissory note was paid down by Venture on
December 14, 2021, and $5.0 million of the $6.0 million promissory note was paid
down by Venture on October 20, 2022. Commission income is also received by the
Company's insurance agency for writing policies for third-party insurance
companies. All of the third-party business was sold to Venture at June 30, 2021.
Accordingly, other income from that business diminished in 2022 as that business
transitioned to Venture.

                                       47
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Other income increased by $97,000, or 3.6%, to $2.8 million for the year ended
December 31, 2022, compared to $2.7 million for the year ended December 31,
2021. Other income relating to installment billings and policy issuance costs
was lower in 2022 because of the Venture Transaction. This was offset by the
interest income received from the $6.0 million promissory note during 2022.

Losses and Loss Adjustment Expenses

The tables below detail our losses and LAE and loss ratios for the years ended December 31, 2022 and 2021 (dollars in thousands).



                                       Commercial      Personal
Year Ended December 31, 2022             Lines           Lines        Total

Accident year net losses and LAE $ 46,884 $ 10,272 $ 57,156 Net (favorable) adverse development 23,878

           406       

24,284

Calendar year net loss and LAE $ 70,762 $ 10,678 $ 81,440



Accident year loss ratio                      57.9 %        64.3 %       58.9 %
Net (favorable) adverse development           29.4 %         2.6 %       25.0 %
Calendar year loss ratio                      87.3 %        66.9 %       83.9 %



                                       Commercial       Personal
Year Ended December 31, 2021             Lines           Lines         Total

Accident year net losses and LAE $ 45,393 $ 5,036 $ 50,429 Net (favorable) adverse development 18,475

            957       

19,432

Calendar year net loss and LAE $ 63,868 $ 5,993 $ 69,861



Accident year loss ratio                      51.6 %         45.0 %       50.9 %
Net (favorable) adverse development           21.0 %          8.6 %       19.6 %
Calendar year loss ratio                      72.6 %         53.6 %       70.5 %



Net losses and LAE increased by $11.5 million, or 16.6%, to $81.4 million for
the year ended December 31, 2022, compared to $69.9 million for the year ended
December 31, 2021. The calendar year loss ratios were 83.9% and 70.5% for the
years ended December 31, 2022 and 2021, respectively.

The Company experienced $24.3 million of adverse development for the year ended
December 31, 2022. Of the $24.3 million of adverse development, $23.9 million
was related to the Company's commercial lines of business, while $406,000 was
related to the Company's personal lines of business. Of the $24.3 million of
adverse development, $1.8 million was related to the 2021 accident year, $4.0
million was related to the 2020 accident year, $9.6 million was related to the
2019 accident year, $5.2 million was related to the 2018 accident year, and $3.7
million was related to 2017 and prior accident years. The adverse development
was mostly related to the Company's commercial liability lines and was driven by
multiple factors including significant social inflation generating higher
severity than historical experience, and longer tail exposure than anticipated,
particularly in certain jurisdictions.

The $19.4 million of adverse development in 2021 consisted of $18.5 million from
commercial lines and $957,000 from personal lines and mostly related to the 2019
and prior accident years.

Expense Ratio

Our expense ratio is a measure of the efficiency and performance of the
commercial and personal lines of business (our risk-bearing underwriting
operations). It is calculated by dividing the sum of policy acquisition costs
and other underwriting expenses by the sum of net earned premiums and other
income of the underwriting business. Costs that cannot be readily identifiable
as a direct cost of a segment or product line remain in Corporate for segment
reporting purposes. The expense ratio excludes wholesale agency and Corporate
expenses.

                                       48
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The table below provides the expense ratio by major component:


                             Years Ended December 31,
                              2022             2021

Commercial Lines
Policy acquisition costs          21.8 %            29.2 %
Operating expenses                16.1 %            13.2 %
Total                             37.9 %            42.4 %

Personal Lines
Policy acquisition costs          28.8 %            29.6 %
Operating expenses                12.2 %            12.1 %
Total                             41.0 %            41.7 %

Total Underwriting
Policy acquisition costs          23.0 %            29.3 %
Operating expenses                15.4 %            13.1 %
Total                             38.4 %            42.4 %



Our expense ratio decreased by 4.0% to 38.4% for the year ended December 31,
2022, as compared to the same period in 2021. The decrease was largely due to a
reduction in policy acquisition costs attributable to $11.4 million of ceding
commission from new excess of loss reinsurance treaties. There were no
commissions on excess of loss treaties in 2021.

Policy acquisition costs are costs we incur to issue policies, which include
commissions, premium taxes, underwriting reports and underwriter compensation
costs. The Company offsets direct commissions with ceded commissions from
reinsurers. The percentage of policy acquisition costs to net earned premiums
and other income decreased by 6.3%, from 29.3% in 2021, to 23.0% in 2022, mostly
due to the new ceding commission mentioned above.

Operating expenses consist primarily of employee compensation, information
technology and occupancy costs, such as rent and utilities. Operating expenses
as a percent of net earned premiums and other income increased by 2.3%, from
13.1% in 2021, to 15.4% in 2022. The new excess of loss reinsurance treaties
with the ceding commission drove net earned premiums lower, resulting in a
slightly higher operating expense ratio.

Underwriting Results



We measure the performance of our consolidated results, in part, based on our
underwriting gain or loss. The following table provides the underwriting gain or
loss for the years ended December 31, 2022 and 2021 (dollars in thousands):

                            Underwriting Gain (Loss)

                                     Years Ended December 31,
                                       2022              2021         Change
Commercial Lines                   $     (25,845 )     $ (13,229 )   $ (12,616 )
Personal Lines                            (1,248 )           529        (1,777 )
Total Underwriting                       (27,093 )       (12,700 )     (14,393 )
Wholesale Agency                            (554 )          (261 )        (293 )
Corporate                                   (921 )          (757 )        (164 )
Eliminations                                 239             370         

(131 ) Total underwriting income (loss) $ (28,329 ) $ (13,348 ) $ (14,981 )






                                       49
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Investment Income



Net investment income increased by $1.0 million, or 54.6%, to $3.0 million for
the year ended December 31, 2022, compared to $2.0 million for the year ended
December 31, 2021. This increase was due to an increase in interest income in
our debt securities due to higher interest rates in 2022. Average invested
assets during 2022 were $160.1 million compared to $183.0 million for the same
period in 2021. The investment portfolio was comprised of 81.2% debt securities,
3.5% equity securities, and 15.3% short-term investments as of December 31,
2022. The investment portfolio was comprised of 82.5% debt securities, 7.6%
equity securities, and 9.9% short-term investments as of December 31, 2021.

The debt securities portfolio had an average credit quality was AA+ and AA at
December 31, 2022 and 2021, respectively. The portfolio produced a
tax-equivalent book yield of 2.3% and 1.4% for the years ended December 31, 2022
and 2021, respectively. The option adjusted duration of the debt securities
portfolio was 3.5 years and 3.6 years at December 31, 2022 and 2021,
respectively.

Realized Investment Gains (Losses)



Net realized investment losses were $1.5 million during 2022, compared to $2.9
million of investment gains in 2021. The $4.4 million decrease was due to the
Company repositioning its equity portfolio as well as negative overall market
conditions that were experienced during 2022.

Interest Expense



Interest expense was $2.9 million for the years ended December 31, 2022 and
2021. We issued $25.3 million of public senior unsecured notes (the "Notes") in
2018. The Company did not repurchase any of the Notes in 2022 and 2021. Interest
expense includes the amortization of debt issuance costs relating to the Notes
which is $260,000 per annum over the 5-year life of the Notes. The interest
expense relating to the amortization of debt issuance costs for the existing
$10.5 million of the Subordinated Notes is $51,000 per annum over the 20-year
life of the Subordinated Notes.

The Company had a $10.0 million line of credit during 2022 and 2021, which it
drew upon and paid down at various times. This contributed to the interest
expense in 2022 and 2021. The Company had no outstanding balance on its line of
credit on December 31, 2022, as the line of credit agreement matured on December
1, 2022. The line of credit agreement was not renewed with the Lender after it
matured on December 1, 2022.

Income Tax Expense

For the year ended December 31, 2022, the Company reported $6,000 of current
federal income tax expense and $39,000 of current state income tax expense. The
Company reported a deferred tax benefit of $9.4 million and $0 for the years
ended December 31, 2022 and 2021, respectively.

There is a $21.7 million valuation allowance against 100% of the net deferred
tax assets at December 31, 2022, which would increase book value by $1.77 per
share if reversed in the future. The valuation allowance was $14.6 million as of
December 31, 2021. As of December 31, 2022, the Company has net operating loss
carryforwards for federal income tax purposes of $65.6 million, of which $50.4
million expire in tax years 2030 through 2042 and $15.2 million never expire. Of
this amount, $7.6 million are limited in the amount that can be utilized in any
one year and may expire before they are realized under Section 382 of the
Internal Revenue Code. The Company has state net operating loss carryforwards of
$107.2 million, which expire in tax years 2023 through 2042.


                                       50
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Results of Operations - 2021 Compared to 2020

The following table summarizes our operating results for the years indicated (dollars in thousands):



                           Summary Operating Results

                                            Years Ended December 31,
                                             2021               2020         $ Change       % Change
Gross written premiums                   $     132,095       $  111,335     $   20,760           18.6 %

Net written premiums                     $     101,429       $   92,940     $    8,489            9.1 %

Net earned premiums                      $      98,802       $   89,103     $    9,699           10.9 %
Other income                                     2,671            2,615             56            2.1 %
Losses and loss adjustment expenses,
net                                             69,861           56,228         13,633           24.2 %
Policy acquisition costs                        28,451           26,105          2,346            9.0 %
Operating expenses                              16,509           18,468         (1,959 )        (10.6 %)
Underwriting gain (loss)                       (13,348 )         (9,083 )       (4,265 )        (47.0 %)
Net investment income                            1,968            3,156         (1,188 )        (37.6 %)
Net realized investment gains                    2,878            8,126         (5,248 )        (64.6 %)
Change in fair value of equity
securities                                      (2,020 )            228         (2,248 )            *
Other gains (losses)                            11,664              260         11,404              *
Interest expense                                 2,852            2,925            (73 )         (2.5 %)
Income (loss) before income taxes               (1,710 )           (238 )       (1,472 )            *
Equity earnings (losses) in Affiliate,
net of tax                                         824              839            (15 )         (1.8 %)
Income tax expense (benefit)                       208                6            202              *
Net income (loss)                        $      (1,094 )     $      595     $   (1,689 )            *
Underwriting Ratios:
Loss ratio (1)                                    70.5 %           62.8 %
Expense ratio (2)                                 42.4 %           45.6 %
Combined ratio (3)                               112.9 %          108.4 %




(1)
The loss ratio is the ratio, expressed as a percentage, of net losses and loss
adjustment expenses to net earned premiums and other income from underwriting
operations.

(2)

The expense ratio is the ratio, expressed as a percentage, of policy acquisition costs and operating expenses to net earned premiums and other income from underwriting operations.

(3)

The combined ratio is the sum of the loss ratio and the expense ratio. A combined ratio under 100% indicates an underwriting profit. A combined ratio over 100% indicates an underwriting loss.

* Percentage change is not meaningful


                                       51
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Premiums



Premiums are earned ratably over the term of the policy, whereas written
premiums are reflected on the effective date of the policy. Almost all
commercial lines and homeowners products have annual policies, under which
premiums are earned evenly over one year. The resulting net earned premiums are
impacted by the gross and ceded written premiums, earned ratably over the terms
of the policies.

Our premiums are presented below for the years ended December 31, 2021 and 2020
(dollars in thousands):

                           Summary of Premium Revenue

                           Years Ended December 31,
                             2021              2020        $ Change       % Change
Gross written premiums
Commercial lines         $     117,075       $ 102,763     $  14,312           13.9 %
Personal lines                  15,020           8,572         6,448           75.2 %
Total                    $     132,095       $ 111,335     $  20,760           18.6 %

Net written premiums
Commercial lines         $      87,307       $  85,385     $   1,922            2.3 %
Personal lines                  14,122           7,555         6,567           86.9 %
Total                    $     101,429       $  92,940     $   8,489            9.1 %

Net Earned premiums
Commercial lines         $      87,759       $  82,409     $   5,350            6.5 %
Personal lines                  11,043           6,694         4,349           65.0 %
Total                    $      98,802       $  89,103     $   9,699           10.9 %



Gross written premiums increased by $20.8 million, or 18.6%, to $132.1 million
for the year ended December 31, 2021, compared to $111.3 million for the year
ended December 31, 2020. The increase was attributable to an increase in written
premium in our small business and low-value dwelling programs, which was
slightly offset by a decrease in written premium in our hospitality programs.

Commercial lines gross written premiums increased $14.3 million, or 13.9%, to
$117.1 million, for the year ended December 31, 2021, compared to $102.8 million
for the year ended December 31, 2020. Gross written premiums for our small
business programs increased by $20.3 million, or 31.1%, to $85.4 million for the
year ended December 31, 2021, compared to $65.1 million for the year ended
December 31, 2020. This increase was offset by our hospitality programs gross
written premiums, which decreased by $5.9 million, or 15.8%, to $31.7 million
for the year ended December 31, 2021, compared to $37.7 million for the year
ended December 31, 2020.

Personal lines gross written premiums increased $6.4 million, or 75.2%, to $15.0
million for the year ended December 31, 2021, compared to $8.6 million for the
same period in 2020. This increase was largely driven by our low-value dwelling
business.

Net written premiums increased $8.5 million, or 9.1%, to $101.4 million, for the
year ended December 31, 2021, compared to $92.9 million, for the year ended
December 31, 2020. The increase was due to the increase in gross written premium
during 2021. However, this increase was reduced by increased reinsurance rates,
and the Company entering into a new specific loss commercial liability treaty on
December 31, 2021, that included a 40% ceding commission and resulted in an
additional $4.4 million of ceded written premiums at the inception of the
agreement. Ceding commissions increased by $1.8 million as well. Ceded earned
premiums and total acquisition costs were not impacted in 2021 from this new
treaty, after taking into account the change in deferred acquisition costs.
However, going forward, we would expect to see higher ceded earned premiums and
lower acquisition costs as a result of this treaty.

                                       52
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Other Income



Other income consists primarily of fees charged to policyholders by the Company
for services outside of the premium charge, such as installment billings and
policy issuance costs. Other income also includes the interest income from the
$6.0 million and $3.0 million promissory notes relating to the Venture
Transaction. The $3.0 million promissory note was paid down by Venture on
December 14, 2021. Commission income is also received by the Company's insurance
agency for writing policies for third-party insurance companies. All of the
third-party business was sold to Venture at June 30, 2021. Accordingly, other
income from that business will diminish over the next few quarters as it
transitions over to Venture, and will ultimately no longer occur. Other income
increased by $56,000, or 2.1%, to $2.7 million for the year ended December 31,
2021, compared to $2.6 million in 2020. Other income relating to installment
billings and policy issuance costs was lower in the second half of 2021, as the
business that was sold to Venture at June 30, 2021, no longer produces other
income for the Company. This was more than offset by an increase in the interest
income in 2021 of $306,000 from the notes payable.

Losses and Loss Adjustment Expenses

The tables below detail our losses and LAE and loss ratios for the years ended December 31, 2021 and 2020 (dollars in thousands).


                                     Commercial       Personal
Year Ended December 31, 2021           Lines           Lines         Total

Accident year net losses and LAE $ 45,393 $ 5,036 $ 50,429 Net (favorable) adverse development 18,475

            957       

19,432

Calendar year net loss and LAE $ 63,868 $ 5,993 $ 69,861



Accident year loss ratio                    51.6 %         45.0 %       50.9 %
Net (favorable) adverse development         21.0 %          8.6 %       19.6 %
Calendar year loss ratio                    72.6 %         53.6 %       70.5 %



                                       Commercial       Personal
Year Ended December 31, 2020             Lines           Lines         Total

Accident year net losses and LAE $ 38,021 $ 2,613 $ 40,634 Net (favorable) adverse development 15,242

            352       

15,594

Calendar year net loss and LAE $ 53,256 $ 2,965 $ 56,228



Accident year loss ratio                      46.0 %         38.2 %       45.4 %
Net (favorable) adverse development           18.4 %          5.1 %       17.4 %
Calendar year loss ratio                      64.4 %         43.3 %       62.8 %



Net losses and LAE increased by $13.6 million, or 24.2% to $69.9 million for the
year ended December 31, 2021, compared to $56.2 million in 2020. The calendar
year loss ratios were 70.5% and 62.8% for the years ended December 31, 2021 and
2020, respectively.

The $19.4 million of adverse development in 2021 consisted of $18.5 million from
commercial lines and $957,000 from personal lines and mostly related to the 2019
and prior accident years.

The $15.6 million of adverse development in 2020 consisted of $15.2 million from
commercial lines and $352,000 from personal lines and mostly related to the 2018
and 2017 accident years.

Expense Ratio

Our expense ratio is a measure of the efficiency and performance of the
commercial and personal lines of business (our risk-bearing underwriting
operations). It is calculated by dividing the sum of policy acquisition costs
and other underwriting expenses by the sum of net earned premiums and other
income of the underwriting business. Costs that cannot be readily identifiable
as a direct cost of a segment or product line remain in Corporate for segment
reporting purposes. The expense ratio excludes wholesale agency and Corporate
expenses.

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The table below provides the expense ratio by major component:



                          Years Ended December 31,
                            2021            2020

Commercial Lines
Policy acquisition costs    29.2%           30.3%
Operating expenses          13.2%           15.3%
Total                       42.4%           45.6%

Personal Lines
Policy acquisition costs    29.6%           29.9%
Operating expenses          12.1%           15.6%
Total                       41.7%           45.5%

Total Underwriting
Policy acquisition costs    29.3%           30.3%
Operating expenses          13.1%           15.3%
Total                       42.4%           45.6%


Our expense ratio decreased by 3.2%, to 42.4% for the year ended December 31, 2021, as compared to the same period in 2020.



Policy acquisition costs are costs we incur to issue policies, which include
commissions, premium taxes, underwriting reports and underwriter compensation
costs. The Company offsets direct commissions with ceded commissions from
reinsurers. The percentage of policy acquisition costs to net earned premiums
and other income decreased by 1.0%, from 30.3% in 2020, to 29.3% in 2021.

Operating expenses consist primarily of employee compensation, information
technology and occupancy costs, such as rent and utilities. Operating expenses
as a percent of net earned premiums and other income was 13.1% and 15.3% for the
years ended December 31, 2021 and 2020, respectively. The lower operating
expense ratio was largely due to the Venture Transaction, where 21 employees
transitioned from Conifer to Venture on June 30, 2021.

Underwriting Results



We measure the performance of our consolidated results, in part, based on our
underwriting gain or loss. The following table provides the underwriting gain or
loss for the years ended December 31, 2021 and 2020 (dollars in thousands):

                            Underwriting Gain (Loss)

                                     Years Ended December 31,
                                       2021              2020         Change
Commercial Lines                   $     (13,229 )     $  (8,307 )   $ (4,922 )
Personal Lines                               529             766         (237 )
Total Underwriting                       (12,700 )        (7,541 )     (5,159 )
Wholesale Agency                            (261 )          (474 )        213
Corporate                                   (757 )        (1,403 )        646
Eliminations                                 370             335           35

Total underwriting income (loss) $ (13,348 ) $ (9,083 ) $ (4,265 )






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Investment Income



Net investment income decreased by $1.2 million, or 37.6%, to $2.0 million for
the year ended December 31, 2021, compared to $3.1 million for the year ended
December 31, 2020. This decrease was due to a decrease in interest income in our
debt securities due to lower interest rates. Average invested assets during 2021
were $183.0 million compared to $176.5 million for the same period in 2020. The
investment portfolio was comprised of 82.5% debt securities, 7.6% equity
securities, and 9.9% short-term investments as of December 31, 2021. The
investment portfolio was comprised of 80.2% debt securities, 7.1% equity
securities and 12.7% short-term investments as of December 31, 2020.

The debt securities portfolio had an average quality was AA and AA+ at December
31, 2021 and 2020, respectively. The portfolio produced a tax-equivalent book
yield of 1.4% and 1.6% for the years ended December 31, 2021 and 2020,
respectively. The option adjusted duration of the debt securities portfolio was
3.6 years at December 31, 2021 and 2020, respectively.

Realized Investment Gains



Net realized investment gains decreased by $5.3 million, or 64.6%, to $2.9
million for the year ended December 31, 2021, as compared to $8.1 million for
the year ended December 31, 2020. The decrease was due to overall market
conditions in 2021 that reduced the Company's ability to sell portions of its
debt and equity securities for realized gains.

Interest Expense



Interest expense was $2.9 million for the years ended December 31, 2021 and
2020. We issued $25.3 million of public senior unsecured notes (the "Notes") in
2018. Proceeds from the Notes were used to pay down $19.5 million of the $30.0
million of subordinated notes that were issued in the third quarter of 2017. The
Company did not repurchase any of the Notes in 2021. The Company repurchased
36,761 units of the Notes in the public market in 2020. Interest expense
includes the amortization of debt issuance costs relating to the Notes which is
$260,000 per annum over the 5-year life of the Notes. The interest expense
relating to the amortization of debt issuance costs for the existing $10.5
million of the Subordinated Notes is $51,000 per annum over the 20-year life of
the Subordinated Notes.

The Company has a $10.0 million line of credit, which it drew upon and paid down
at various times throughout 2021, and which contributed to interest expense. The
Company had no outstanding balance on its line of credit as of December 31,
2021.

Income Tax Expense



For the year ended December 31, 2021, the Company reported $5,000 of current
federal income tax expense and $203,000 of current state income tax expense. The
Company reported a deferred tax benefit of $0 for the years ended December 31,
2021 and 2020, respectively.

There is a $14.6 million valuation allowance against 100% of the net deferred
tax assets at December 31, 2021, which would increase book value by $1.50 per
share if reversed in the future. The valuation allowance was $13.3 million as of
December 31, 2020. As of December 31, 2021, the Company has net operating loss
carryforwards for federal income tax purposes of $59.7 million, of which $49.8
million expire in tax years 2028 through 2041 and $9.9 million never expire. Of
this amount, $12.8 million are limited in the amount that can be utilized in any
one year and may expire before they are realized under Section 382 of the
Internal Revenue Code. The Company has state net operating loss carryforwards of
$17.0 million, which expire in tax years 2022 through 2041.


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Liquidity and Capital Resources

Sources and Uses of Funds



At December 31, 2022, we had $54.0 million in cash, cash equivalents, and
short-term investments. Our principal sources of funds are insurance premiums,
investment income, proceeds from maturity and sale of invested assets and other
income. These funds are primarily used to pay claims, commissions, employee
compensation, taxes and other operating expenses, and service debt.

Management plans to issue new public debt or sell assets that will provide
sufficient cash flow to pay off the senior unsecured notes that are coming due
within the next twelve months. We believe it is probable that we will be able to
issue new public debt or sell assets and repay the senior unsecured notes by
September 30, 2023. We believe that our existing cash, cash equivalents,
short-term investments and investment securities balances will be adequate to
meet our operating liquidity needs and the needs of our subsidiaries on a
short-term and long-term basis. With the expected execution of the senior debt
refinancing, we believe we can meet our capital needs as well over the next
twelve months.

We believe that our existing cash, cash equivalents, short-term investments and
investment securities balances will be adequate to meet our capital and
liquidity needs and the needs of our subsidiaries on a short-term and long-term
basis.

We conduct our business operations primarily through our Insurance Company
Subsidiaries. Our ability to service debt, and pay administrative expenses is
primarily reliant upon our intercompany service fees paid by the Insurance
Company Subsidiaries to the holding company for management, administrative, and
information technology services provided to the Insurance Company Subsidiaries
by the Parent Company. Secondarily, the Parent Company may receive dividends
from the Insurance Company Subsidiaries; however, this is not the primary means
in which the holding company supports its funding as state insurance laws
restrict the ability of our Insurance Company Subsidiaries to declare dividends
to the Parent Company. Generally, the limitations are based on the greater of
statutory net income for the preceding year or 10% of statutory surplus at the
end of the preceding year. No dividends were paid from our Insurance Company
Subsidiaries in 2022, 2021 or 2020.

We contributed $6.8 million, $11.4 million and $1.2 million to our Insurance
Company Subsidiaries in 2022, 2021 and 2020, respectively. We believe that the
current statutory surplus levels and the funds available at the holding company
level will provide the necessary statutory capital to support our premium volume
growth over the next twelve months.

We are aware that our outstanding debt securities are currently trading at a
discount to their face amount. In order to reduce future cash interest payments,
as well as future amounts due at maturity or upon redemption, we may, from time
to time, purchase such debt for cash, in exchange for common stock, or for a
combination of cash and common stock, in open market or privately negotiated
transactions. We will evaluate any such transactions in light of then-existing
market conditions, taking into account our current liquidity and prospects for
future access to capital. The amounts involved in such transactions,
individually or in the aggregate, may be material.

Cash Flows

Operating Activities. Cash used by operating activities for the year ended December 31, 2022 was $40.5 million compared to cash provided by operating activities of $5.4 million for the same period in 2021. The $45.9 million decrease was primarily due to a $45.2 million increase in paid losses and $8.0 million decrease in premiums collected, net of reinsurance premiums. This decrease was offset by a $6.9 million decrease in the amount of acquisition costs paid during 2022 compared to 2021.



Cash provided by operating activities for the year ended December 31, 2021 was
$5.4 million, compared to $3.0 million for the same period in 2020. The $2.4
million increase was primarily due to a $12.4 million increase in premiums
collected, net of reinsurance premiums. This increase was offset by a $6.6
million increase in paid claims, a $2.7 million increase in acquisition costs
paid, and a $1.4 million decrease in investment income received.

Investing Activities. Cash provided by investing activities for the year ended
December 31, 2022 was $56.5 million compared to $1.4 million in 2021. The $55.1
million increase in cash provided by investing activities over the prior year
was

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driven by $34.3 million increase in net proceeds from sale of investments in
2022, compared to the same period in 2021. The Company also experienced an
increase of $32.8 million from its sale of agency business in 2022, compared to
the same period in 2021.

Cash provided by investing activities for the year ended December 31, 2021 was
$1.4 million. Cash used in investing activities was $7.3 million in 2020. The
$8.7 million increase in cash provided by investing activities over the prior
year was driven by a reduction in the purchases of investments in 2021, compared
to the same period in 2020. There was a significant repositioning of the
Company's portfolio during the year ended 2020 from the COVID-19 pandemic, which
caused an increase in the purchase of investments.

Financing Activities. Cash provided by financing activities for the years ended
December 31, 2022, was $2.1 million compared to $5.0 million of cash used by
financing activities for years ended December 31, 2021. The $7.1 million
increase was largely attributed to the Company raising $5.0 million through the
issuance of additional common stock in August 2022.

Cash used by financing activities for the years ended December 31, 2021, was
$5.0 million compared to $5.1 million of cash provided by financing activities
for years ended December 31, 2020. The $10.1 million decrease in cash provided
by financing activities was mostly due to the Company paying down $8.0 million
on its line of credit during 2021. The Company's borrowings under debt
arrangements were also $2.7 million less in 2021 compared to 2020.

Outstanding Debt



On April 24, 2020, the Company received a $2.7 million PPP loan from the line of
credit Lender pursuant to the Paycheck Protection Program of the CARES Act
administered by the SBA. The Company received notice from the SBA that the loan
was 100% forgiven, including accrued interest, on July 8, 2021. This resulted in
a $2.8 million gain that is included in Other Gains on the Consolidated
Statement of Operations.

In 2018, the Company issued $25.3 million of Notes. The Notes bear an interest
rate of 6.75% annum, payable quarterly at the end of March, June, September and
December and mature on September 30, 2023. Proceeds from the Notes were used to
pay down $19.5 million of the $30.0 million of subordinated notes that were
issued in the third quarter of 2017. The Company did not repurchase any of the
Notes during 2022 and 2021. The Company repurchased 36,761 units of the Notes in
the public market during 2020 with a face value of $919,000. The Notes were
repurchased at a discount to face value, which resulted in a $260,000 gain on
extinguishment in 2020. This gain is reflected in the Consolidated Statement of
Operations as Other gains.

The Company also has outstanding $10.5 million of Subordinated Notes maturing on
September 30, 2038. The Subordinated Notes bear an interest rate of 7.5% per
annum until September 30, 2023, and 12.5% thereafter, and allow for four
quarterly interest payment deferrals. Interest is payable quarterly at the end
of March, June, September and December. Beginning September 30, 2021, the
Company may redeem the Subordinated Notes, in whole or in part, for a call
premium of $1.1 million. The call premium escalates each quarter to ultimately
$1.75 million on September 30, 2023, then steps up to $3.05 million on December
31, 2023, and increases quarterly at a 12.5% per annum rate thereafter.

The carrying value of the Notes and Subordinated Notes are offset by $1.0 million of debt issuance costs that will be amortized through interest expense over the life of the loans. Refer to Note 9 ~ Debt of the Notes to the Consolidated Financial Statements, for additional information regarding our outstanding debt.



The Company maintained a $10.0 million line of credit with a national bank (the
"Lender") that matured on December 1, 2022. The line of credit was not renewed
after it matured. The line of credit contained interest at the London Interbank
rate ("LIBOR") plus 2.75% per annum, payable monthly.

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Contractual Obligations and Commitments

The following table is a summary of our contractual obligations and commitments as of December 31, 2022 (dollars in thousands):



                                                               Payments due by period
                                                  Less than          One to            Three to         More than
                                    Total         one year         three years        five years        five years
Senior unsecured notes            $  24,381      $    24,381      $           -      $          -      $          -
Interest on senior unsecured
notes                                 1,234            1,234                  -                 -                 -
Subordinated notes                   10,500                -                  -                 -            10,500
Interest on subordinated notes       20,606              919              2,625             2,625            14,437
Lease obligations                     1,634              328                505               432               369
Unpaid loss and loss
adjustment expense (1)              165,539           59,010             66,646            28,890            10,993
Purchase Obligations (2)              1,380              360                720               300                 -
Total                             $ 225,274      $    86,232      $      70,496      $     32,247      $     36,299



(1)
The estimated unpaid loss and loss adjustment expense payments were made using
estimates based on historical payment patterns. However, future payments may be
different than historical payment patterns.

(2)


Includes estimated future payments under the software license agreement relating
to our policy issuance system. This agreement requires minimum monthly payments
of $30,000, and is variable with premium volume. The future payment assumptions
are based on the minimum monthly payments. The software license agreement
expires on November 1, 2026.

Regulatory and Rating Issues



The NAIC has a RBC formula to be applied to all property and casualty insurance
companies. The formula measures required capital and surplus based on an
insurance company's products and investment portfolio and is used as a tool to
evaluate the capital adequacy of regulated companies. The RBC formula is used by
state insurance regulators to monitor trends in statutory capital and surplus
for the purpose of initiating regulatory action. In general, an insurance
company must submit a calculation of its RBC formula to the insurance department
of its state of domicile as of the end of the previous calendar year. These laws
require increasing degrees of regulatory oversight and intervention as an
insurance company's RBC declines.

At December 31, 2022, all of our Insurance Company Subsidiaries were in excess of any minimum threshold at which corrective action would be required.



Insurance operations are subject to various leverage tests (e.g.,
premium-to-statutory surplus ratios), which are evaluated by regulators and
rating agencies. As of December 31, 2022, on a trailing twelve-month statutory
combined basis, the gross written and net written premium leverage ratios were
2.3 to 1.0 and 1.5 to 1.0, respectively.

The NAIC's IRIS was developed to assist state insurance departments in executing
their statutory mandates to oversee the financial condition of insurance
companies operating in their respective states. IRIS identifies thirteen
industry ratios and specifies "usual values" for each ratio. State insurance
regulators review the IRIS ratio results to determine if an insurer is in need
of further regulatory scrutiny or action. While the ratios, individually and
collectively, are useful tools for identifying companies that may be
experiencing financial difficulty, they are only a guide for regulators and
should not be considered an absolute indicator of a Company's financial
condition. While inquiries from regulators are not uncommon, our Insurance
Company Subsidiaries have not experienced any regulatory actions due to their
IRIS ratio results or otherwise.

Recently Issued Accounting Pronouncements



Refer to Note 1 ~ Summary of Significant Accounting Policies: Recently Issued
Accounting Guidance of the Notes to the Consolidated Financial Statements for
detailed information.

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