Conifer Holdings, Inc. (Form: 8-K, Received: 12/22/2023 16:01:08)

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

FORM 8-K

CURRENT REPORT

PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

Date of Report (Date of earliest event Reported): December 20, 2023

Conifer Holdings Inc.

(Exact Name of Registrant as Specified in Charter)


Michigan	001-37536	27-1298795
(State or Other Jurisdiction of Incorporation)	(Commission File Number)	(I.R.S. Employer Identification Number)

3001 West Big Beaver Road, Suite 200

Troy, MI 48084

(Address of Principal Executive Offices) (Zip Code)

Registrant's telephone number, including area code: (248) 559-0840

(Former name or former address, if changed since last report)

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions:


☐	Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)
☐	Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)
☐	Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))
☐	Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

Securities registered pursuant to Section 12(b) of the Act:


Title of each class	Trading Symbol(s)	Name of each exchange on which registered
Common Stock, no par value	CNFR	The Nasdaq Stock Market LLC
9.75% Senior Notes due 2028	CNFRZ	The Nasdaq Stock Market LLC

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§240.12b-2 of this chapter)

Emerging growth company ☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐

Item 1.01. Entry Into a Material Definitive Agreement.

On December 20, 2023 (the “Initial Issue Date”), Conifer Holdings, Inc. (the “Company”) sold $6 million of its newly designated Series A Preferred Stock, no par value (the “Series A Preferred Stock”), to Clarkston 91 West LLC (the “Purchaser”), an entity affiliated with Gerald and Jeffrey Hakala, members of the Board of Directors of the Company. The sale of the Series A Preferred Stock was consummated on the Initial Issue Date pursuant to a Securities Purchase Agreement (the “Purchase Agreement”) by and between the Company and the Purchaser.

The Company intends to use the proceeds for working capital and general corporate purposes. The Purchase Agreement contains customary representations and warranties from the Company, on the one hand, and the Purchaser, on the other.

The foregoing description of the Purchase Agreement is a summary and is qualified in its entirety by the terms of Purchase Agreement, which is attached hereto as Exhibit 10.1 and is incorporated herein by reference.

Item 3.02. Unregistered Sales of Equity Securities.

The sale of the Series A Preferred Stock pursuant to the Purchase Agreement has not been registered under the Securities Act of 1933, as amended (the “Securities Act”), in reliance on the exemption from registration provided by Section 4(a)(2) of the Securities Act and certain rules and regulations promulgated thereunder.

The information contained in Items 1.01 and 5.03 of this Current Report on Form 8-K regarding the sale of the Series A Preferred Stock, the Purchase Agreement and the terms of the Series A Preferred Stock is hereby incorporated by reference into this Item 3.02.

Item 3.03. Material Modification to Rights of Security Holders.

The information contained in Item 5.03 of this Current Report on Form 8-K regarding the Certificate of Designation (as defined below) is hereby incorporated by reference into this Item 3.03.

Item 5.02 Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers.

On December 18, 2023, the Company entered into an Employment Agreement with Nicholas J. Petcoff (the “Executive”).

The initial term for the Employment Agreement begins on January 1, 2024 and continues for two years. The Employment Agreement calls for continuing one-year automatic extensions unless the Executive gives written notice of non-extension not less than 30 days prior to the expiration of the term or the Company gives written notice of non-extension prior to the expiration of the term. The Employment Agreements provide for an annual base salary of $425,000, participation in the annual bonus plan, participation in any long-term incentive plan made generally available to senior executive officers of the Company and other fringe benefits and perquisites as are generally made available to the Company’s executives.

If the Executive’s employment is terminated for cause, the Executive will receive the accrued and unpaid portion of base salary. If the Executive’s employment is terminated due to death or permanent disability, the Executive (or his legal representative or beneficiary) will receive the accrued and unpaid portion of base salary and any earned but not yet paid incentive awards for already completed years or award cycles. If the Executive’s employment is terminated without cause or if he terminates his employment for good reason (assuming the change of control provisions below do not apply), the Executive will receive the accrued and unpaid portion of base salary, any earned but not yet paid incentive awards for already completed years or award cycles, plus two times his annual base salary. In addition, any unvested equity awards will immediately vest. If the Executive’s employment is terminated without cause (other than due to death or permanent disability) or he terminates such employment for good reason, in each case within 24 months after a change of control, the Executive will receive the accrued and unpaid portion of base salary, any earned but not yet paid incentive awards for already completed years or award cycles and

2.99 times the sum of (i) his annual base salary and (ii) the greater of his annual target bonus or his average bonus for the prior three years. In addition, any unvested equity awards will immediately vest.

The employment agreements also provide for ongoing confidentiality requirements and for non-competition and non-solicitation provisions for two years after termination of employment.

Item 5.03. Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year.

On December 20, 2023, the Company filed the Certificate of Designation of Series A Preferred Stock (the “Certificate of Designation”) to the Company’s Second Amended and Restated Certificate of Incorporation with the Secretary of State of the State of Michigan, effective as of such date, designating 1,000 shares of Series A Preferred Stock (the “Shares”) out of the authorized but unissued shares of Preferred Stock as “Series A Senior Preferred Stock,” and designating the dividend, preferences, rights, voting power, restrictions, limitations as to dividends and other distributions, qualifications and terms and conditions of redemption of such Shares. A description of the material terms of the Series A Preferred Stock, as contained within the Certificate of Designation, is set forth below:


Issue:		Series A Preferred Stock

Number of Shares Designated		1,000

Ranking, with respect to dividend rights and distribution rights upon the liquidation, winding-up or dissolution of the Company:		The Series A Preferred Stock will rank senior to all of the common stock of the Company.

Maturity:		June 30, 2026 (the “Maturity Date”)

Issue Price per Share:		$6,000

Dividend Rate:		The “Series A Dividend Rate” is equal to the prime rate of Waterford Bank, N.A. (“Waterford Bank”) on the date that is 30 days prior to the applicable Dividend Payment Date (as defined in the Certificate of Designation) plus 200 basis points, provided, however, that if the prime rate determined by Waterford Bank shall ever be less than 8.0% per annum, (the “Floor” as defined in the Certificate of Designation), then the prime rate shall be deemed to be the Floor.

Liquidation Preference:		In the event of any Liquidation Event, after the satisfaction in full of the debts of the Company and the payment of any liquidation preference owed to the holders of shares of capital stock of the Company ranking senior to the Series A Preferred Stock, pari passu with the holders of any Parity Securities (as defined in the Certificate of Designation) by reason of their ownership thereof, but before any distribution or payment out of the assets of the Company shall be made to the holders of Junior Securities (as defined in the Certificate of Designation) by reason of their ownership thereof, an amount in cash per share equal to the Series A Redemption Price (as defined below).

Optional Redemption:		The Company has the right at the end of any fiscal quarter on or after the Initial Issue Date and up to and including the Maturity Date, to redeem, at its option, in whole or in part, the Series A Preferred Shares. Any such optional redemption shall be effected only out of funds legally available for such purpose. The Company may undertake multiple partial redemptions. Any redemption of the Series A Preferred Shares shall occur on a date set by the Company, subject to certain limitations, at an amount per share equal to the applicable Series A Redemption Price (as defined below). The Series A Preferred Shares may be redeemed pro rata (unless otherwise agreed upon in writing by each Holder of Series A Preferred Shares).

Redemption Amount:		The Series A Preferred Shares may be redeemed at a price equal to (i) the Series A Issue Price, plus (ii) the amount that would result in a 20.0%, compounded annually, annualized return to the holder, on the portion of the holder’s shares of Series A Preferred Shares being redeemed, taking into


		account the payment of the Series A Issue Price and the dividends actually received by such holder on the Series A Preferred Shares, calculated at the time of such redemption; provided, that the redemption premium shall not be less than $75,000 (the “Series A Redemption Price”).

Automatic Conversion:		The outstanding Series A Preferred Shares shall only be convertible for shares of the Company’s common stock, no par value (the “Common Stock”), at the Maturity Date. On the Maturity Date, each outstanding share of the Series A Preferred Shares, that has not otherwise been redeemed, shall, without any further action by the holders, automatically be converted into 4,000 shares of Common Stock (equal to the purchase price of $6,000 per each share of Series A Preferred Stock, divided by 1.50), subject to adjustment for reverse and forward stock splits, stock dividends, stock combinations and other similar transactions of the Common Stock that occur after the Initial Issue Date (the “Automatic Conversion”). Upon the Automatic Conversion, the holder shall be deemed to be the holder of record of the Common Stock issuable upon such conversion.

Voting:		The Preferred Stock has no voting rights for directors or otherwise, except as required by law or as contemplated in the Certificate of Designation with respect to protective provisions.

The foregoing description of the Certificate of Designation is a summary and is qualified in its entirety by the Certificate of Designation, which is attached hereto as Exhibit 3.1 and is incorporated herein by reference. In addition, the information set forth above under Item 1.01 is hereby incorporated by reference into this Item 5.03.

Forward-Looking Statements

Certain matters discussed in this Current Report on Form 8-K and other company communications constitute forward-looking statements within the meaning of the federal securities laws. Generally, the use of words such as “expect,” “intend,” “estimate,” “believe,” “anticipate,” “will,” “forecast,” “plan,” “project,” or similar words identify forward-looking statements that we intend to be included within the safe harbor protections provided by the federal securities laws. Forward-looking statements are subject to risks and uncertainties that could cause actual results to differ materially from those expressed or implied by such statements. Such risks and uncertainties include, among others, risks related to: the Company’s use of proceeds from the sale of the Series A Preferred Stock; the Company’s ability to meet the requirement for continued listing on the Nasdaq Global Market under Nasdaq Listing Rules; the Company’s ability to accurately assess the potential losses and loss adjustment expenses under the terms of the insurance policies we underwrite; the Company’s ability to accurately underwrite risks and charge competitive yet profitable rates to our policyholders; the Company’s ability to compete effectively against larger or more well‑established business rivals; the impact on the Company of severe weather conditions and the Company’s ability to obtain reinsurance; the effects of adverse economic factors, including recession, inflation, rising interest rates or lower economic activity; the performance of the Company’s investment portfolio; the Company’s financial flexibility and financial condition; and the various risks described in the “Risk Factors” section and elsewhere in the Company’s Quarterly Report on Form 10-Q for the period ended September 30, 2023 and Annual Report on Form 10-K for the year ended December 31, 2022, and in other filings with the SEC. Such statements are not guarantees of future performance and involve certain risks, uncertainties and assumptions, which are difficult to predict and many of which are beyond our control. Therefore, actual outcomes and results may differ materially from those matters expressed or implied in such forward-looking statements. You should not place undue reliance on any forward-looking statements. The Company undertakes no obligation to update publicly any forward-looking statements for any reason, unless required by law, even if new information becomes available or other events occur in the future.

Item 9.01. Financial Statements and Exhibits.


	(d)	Exhibits.


Exhibit No.		Description
3.1		Certificate of Designation of Series A Preferred Stock
10.1		Purchase Agreement, dated December 20, 2023, by and between Conifer Holdings, Inc. and Clarkston Capital, LLC*
104		Cover Page Interactive Data File (embedded within the Inline XBRL document)

SIGNATURE

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.


	Conifer Holdings Inc.

Date: December 22, 2023	By:	/s/ BRIAN J. RONEY
		Brian J. Roney
		President

CERTIFICATE OF DESIGNATION

OF
SERIES A PREFERRED STOCK
OF
CONIFER HOLDINGS, INC.

Pursuant to Section 302(3) of the Michigan Business Corporation Act

Pursuant to Section 302(3) of the Michigan Business Corporation Act (the “MBCA”), Conifer Holdings, Inc., a corporation duly organized and validly existing under the laws of the State of Michigan (the “Corporation”), in accordance with the provisions of Section 302(3) thereof, does hereby submit the following:

WHEREAS, the Second Amended and Restated Articles of Incorporation of the Corporation (as amended, restated, supplemented, or otherwise modified from time to time, the “Articles of Incorporation”) and the MBCA authorize the issuance of 10,000,000 shares of Preferred Stock of the Corporation, issuable from time to time, in one or more series, with such designations and such relative voting, dividend, liquidation and other rights preferences and limitations and authorizes the Board of Directors of the Corporation (the “Board”), subject to the limitations under applicable Michigan law, to fix the rights, powers and duties thereof, without any shareholder vote; and

WHEREAS, it is the desire of the Board to establish and fix the number of shares to be included in a new series of Preferred Stock and the designations, rights, preferences, powers, restrictions, and limitations of the shares of such new series.

NOW, THEREFORE, BE IT RESOLVED, that the Board does hereby provide authority for the Corporation to issue and designate 1,000 shares of the Preferred Stock to be known as “Series A Preferred Stock” (each such share, a “Series A Preferred Share” and collectively, the “Series A Preferred Shares”) and does hereby in this Certificate of Designation (this “Certificate of Designation”) establish and fix and herein state and express the designations, rights, preferences, powers, restrictions, and limitations of such Series A Preferred Shares as follows:

Section 1.         General Matters; Ranking.

2.01 The Corporation may, without notice to or consent of the Holders of the then outstanding Series A Preferred Shares, authorize and issue additional Series A Preferred Stock by filing an amendment to this Certificate of Designation with respect to such additional shares.

2.02 Each Series A Preferred Share shall be identical in all respects to every other Series A Preferred Share. The Series A Preferred Shares, with respect to dividend rights and distribution rights upon the liquidation, winding-up or dissolution of the Corporation, shall rank senior to any Junior Securities.

2.03 The Series A Preferred Shares that are redeemed, converted, or otherwise acquired by the Corporation pursuant to this Certificate of Designation shall be cancelled and shall resume the status of authorized but unissued Preferred Shares of the Corporation, undesignated as to series.

Section 2.         Standard Definitions.

As used herein with respect to the Series A Preferred Shares:

“Bylaws” means the Amended and Restated Bylaws of the Corporation, as they may be amended or restated from time to time.

“Common Stock” means the common stock, no par value, of the Corporation.

“Conversion Shares” means, collectively, the shares of Common Stock issuable upon conversion of the Series A Preferred Shares in accordance with the terms hereof.

“Dividend Payment Date” means the first day of each fiscal quarter following the Initial Issuance Date (January 1, April 1, July 1 and October 1).

“Floor” means a rate of interest equal to 8.0% per annum.

“Fundamental Transaction” means any event pursuant to which (a) the Corporation and its subsidiaries effects (i) any merger of the Corporation with (but not into) another Person, in which shareholders of the Corporation immediately prior to such transaction own less than a majority of the outstanding stock of the surviving entity, or (ii) any merger or consolidation of the Corporation into another Person, (b) the Corporation effects any sale of thirty-five percent (35%) or more, on a consolidated basis, of the Corporation’s and its subsidiaries’ assets, (c) any tender offer or exchange offer approved or authorized by the Corporation’s Board of Directors is completed pursuant to which holders of at least a majority of the outstanding Common Stock tender or exchange their shares for other securities, cash or property, or (d) the Corporation effects any reclassification of the Common Stock or any compulsory share exchange pursuant to which the Common Stock is effectively converted into or exchanged for other securities, cash or property.

“Holder” means each Person in whose name any Series A Preferred Share is registered, who shall be treated by the Corporation as the absolute owner of such share of the Series A Preferred Stock for all purposes under this Certificate of Designation.

“Initial Issue Date” means December 20, 2023, the original issue date of the Series A Preferred Shares.

“Junior Securities” means collectively, the Common Stock and each other class or series of capital stock of the Corporation, now existing or hereafter authorized, classified or reclassified, the terms of which do not expressly provide that such class or series ranks on a parity basis with or senior to the Series A Preferred Stock as to dividend rights and rights on the distribution of assets on any Liquidation Event.

“Liquidation Event” means a liquidation, dissolution or winding up of the Corporation, whether voluntary or involuntary.

“Maturity Date” means June 30, 2026.

“Parity Securities” means any equity security of the Corporation issued after the Initial Issue Date with terms specifically providing that such equity security ranks on a parity with the Series A Preferred Shares with respect to rights to the payment of dividends and/or distributions upon the liquidation, winding-up and dissolution of the Corporation’s affairs, as applicable.

“Person” means any individual, partnership, firm, corporation, limited liability company, business trust, joint stock company, trust, unincorporated association, joint venture, governmental authority or other entity of any kind.

“Preferred Stock” means the preferred stock of the Corporation.

“Premium Amount” means the amount that would result in a 20.0%, compounded annually, annualized return to the Holder, on the portion of the Holder’s shares of Series A Preferred Shares being redeemed, taking into account the payment of the Series A Issue Price and the dividends actually received by such Holder on the Series A Preferred Shares pursuant to Section 3, calculated at the time of such redemption; provided, that the redemption premium shall not be less than $75,000. See Exhibit A for an illustrative example of this calculation.

“Purchase Agreement” means that certain Securities Purchase Agreement dated as of December 20, 2023, which shall be incorporated by reference into this Certificate of Designation.

“Series A Issue Price” means $6,000 per each share of Series A Preferred Stock.

“Series A Preferred Shares” shall have the meaning set forth in the recitals hereto.

“Series A Redemption Price” shall mean for each share of the Series A Preferred Shares, (i) the Series A Issue Price, plus (ii) the Premium Amount.

“Trading Day” means a day on which the principal Trading Market is open for business.

“Trading Market” means any of the following markets or exchanges on which the Common Stock is listed or quoted for trading on the date in question: the NYSE American, the Nasdaq Capital Market, the Nasdaq Global Market, the Nasdaq Global Select Market, the New York Stock Exchange, an OTC market place or the OTCMarkets (or any successors to any of the foregoing).

Section 3.         Dividends.

3.01          General Obligation. The Holders of the Series A Preferred Shares shall be entitled to receive quarterly dividends, payable in cash, on each Dividend Payment Date, out of funds legally available therefor, from the Initial Issue Date and until the Maturity Date, at the annualized rate per share equal to the then-applicable Series A Dividend Rate on each share of Series A Preferred Shares (the “Series A Dividend”).

3.02          Preferential Payments to Holders of Series A Preferred Shares. No dividend shall be declared or paid or set apart for payment on any Junior Securities (other than a dividend payable solely in Junior Securities) unless the Series A Dividend has been or contemporaneously are being paid or declared and set aside for payment on all outstanding Series A Preferred Shares.

3.03          Series A Dividend Rate. The “Series A Dividend Rate” shall mean a rate equal to the prime rate of Waterford Bank, N.A. (“Waterford Bank”) on the date that is 30 days prior to the applicable Dividend Payment Date plus 200 basis points, provided, however, that if the prime rate determined by Waterford Bank shall ever be less than the Floor, then the prime rate shall be deemed to be the Floor.

Section 4.         Liquidation Preference.

4.01          Liquidation Preference. In the event of any Liquidation Event, after the satisfaction in full of the debts of the Corporation and the payment of any liquidation preference owed to the holders of shares of capital stock of the Corporation ranking senior to the Series A Preferred Shares, pari passu with the holders of any Parity Securities by reason of their ownership thereof, but before any distribution or payment out of the assets of the Corporation shall be made to the holders of Junior Securities by reason of their ownership thereof, an amount in cash per share equal to the Series A Redemption Price.

Section 5.         Redemptions.

5.01          Optional Redemption. The Corporation shall solely have the right at the end of any fiscal quarter on or after the Initial Issue Date and up to and including the Maturity Date, to redeem, at its option, in whole or in part, the Series A Preferred Shares. Any such optional redemption shall be effected only out of funds legally available for such purpose. The Corporation may undertake multiple partial redemptions. Any redemption of the Series A Preferred Shares shall occur on a date set by the Corporation, subject to limitations contained in the first sentence of this Section 5.01 (the “Optional Redemption Date”), at an amount per share equal to the applicable Series A Redemption Price. The Series A Preferred Shares may be redeemed pro rata (unless otherwise agreed upon in writing by each Holder of Series A Preferred Shares), pursuant to Section 5.07.

5.02         Maturity Date. On the Maturity Date, any outstanding shares of the Series A Preferred Shares may be redeemed by the Corporation, but only out of funds legally available at an amount per share equal to the Series A Redemption Price, at the Corporation’s option. Any unredeemed Series A Preferred Shares shall be converted into Common Stock as provided in Section 7.

5.03 Redemption upon a Fundamental Transaction. Upon the consummation of a Fundamental Transaction, any outstanding shares of the Series A Preferred Shares shall be redeemed by the Corporation, but only out of funds legally available at an amount per share equal to the Series A Redemption Price.

5.04          Redemption Notice. The Corporation shall give written notice of redemption pursuant to either Section 5.01 or Section 5.02, as applicable (such notice, the “Redemption Notice”) to each Holder of Series A Preferred Shares not less than ten (10) days and not more than sixty (60) days prior to the Optional Redemption Date or the Maturity Date, as applicable. Such Series A Redemption Notice shall state:

(a)

the date upon which the redemption will occur;

(b)

the number of shares of Series A Preferred Stock held by the Holder that the Corporation shall redeem on the Optional Redemption Date or on the Maturity Date, as applicable;

(c)

the Series A Redemption Price (including a detailed calculation of the Series A Redemption Price); and

(d)

that the Holder is to surrender to the Corporation, in the manner and the place reasonably designated by the Corporation, the Holder’s certificates representing the Series A Preferred Shares to be redeemed.

5.05          Surrender of Certificates; Payment. On or before the Maturity Date or the Optional Redemption Date, as applicable, each Holder of outstanding Series A Preferred Shares shall surrender the certificate or certificates representing such shares (or, if such registered Holder alleges that such certificate has been lost, stolen or destroyed, a lost certificate affidavit and agreement (without bond) reasonably acceptable to the Corporation to indemnify the Corporation against any claim that may be made against the Corporation on account of the alleged loss, theft or destruction of such certificate) to the Corporation, in the manner and at the place reasonably designated by the Corporation, and thereupon the Series A Redemption Price for such shares shall be payable to the order of the person whose name appears on such certificate or certificates as the owner thereof. If fewer than all shares represented by any such certificate are not redeemed, the Corporation shall issue a new certificate to the Holder thereof representing the shares not so redeemed.

5.06          Rights Subsequent to Redemption. Any Series A Preferred Shares that are redeemed or otherwise acquired by the Corporation shall be automatically canceled and shall resume the status of authorized but unissued shares of Preferred Stock and shall no longer be designated as Series A Preferred Stock.

5.07          Pro Rata Redemption. In the event that at any time fewer than all of the outstanding shares of Series A Preferred Stock are to be redeemed pursuant to this Section 5, the redemption shall be made pro rata among all Holders of Series A Preferred Stock in proportion to the number of shares of Series A Preferred Stock then held by them, unless otherwise agreed upon by each holder of Series A Preferred Stock.

Section 6.         Voting Rights.

6.01          General. Holders of record of the Series A Preferred Stock, as such, will have no voting rights, except as required herein and by the MBCA. On any matter on which Holders are required to vote pursuant to the MBCA, such Holders will be entitled to one vote per share of Series A Preferred Stock. However, as long as any shares of the Series A Preferred Stock are outstanding, the Corporation shall not, without the affirmative vote of the Holders of a majority of the then outstanding shares of the Series A Preferred Stock, (i) alter, amend or modify the preferences, privileges or rights given to the Series A Preferred Stock, (ii) alter or amend this Certificate of Designation, or (iii) file any certificate of amendment or certificate of designations of preferences, limitations and relative rights of any series of the Series A Preferred Stock, if such action would adversely alter or change the powers, preferences or rights of the Series A Preferred Stock in a manner materially different than the effect of such actions on the Common Stock (regardless, in the case of clause (i), (ii) or (iii), of whether any of the foregoing actions shall be by means of amendment to the Articles of Incorporation of the Corporation or by merger, consolidation or otherwise).

6.02 Procedures for Voting and Consents. The rules and procedures for calling and conducting any meeting of the Holders (including, without limitation, the fixing of a record date in connection therewith), the solicitation and use of proxies at such a meeting, the obtaining of written consents and any other procedural aspect or matter with regard to such a meeting or such consents shall be governed by any rules the Board, in its discretion, may

adopt from time to time, which rules and procedures shall conform to the requirements of the Articles of Incorporation, the Bylaws, and applicable law.

Section 7.         Conversion.

7.01          No Optional Conversion. The outstanding Series A Preferred Shares shall only be convertible for Conversion Shares at the Maturity Date. The Series A Preferred Shares shall not be convertible at the option of the Holder. Shares of the Series A Preferred Stock converted into shares of the Common Stock in accordance with the terms hereof shall resume the status of authorized but unissued shares of Preferred Stock and shall no longer be designated as Series A Preferred Stock.

7.02 Automatic Conversion. On the Maturity Date, each outstanding shares of the Series A Preferred Shares, that has not otherwise been redeemed pursuant to Section 5, shall, without any further action by Holders and whether or not any certificates representing such shares are surrendered to the Corporation, automatically be converted into 4,000 shares of Common Stock (equal to the purchase price of $6,000 divided by 1.50), subject to adjustment for reverse and forward stock splits, stock dividends, stock combinations and other similar transactions of the Common Stock that occur after the Initial Issue Date (the “Automatic Conversion”). Upon the Automatic Conversion, the Holder shall be deemed to be the holder of record of the Common Stock issuable upon such conversion, notwithstanding that any certificates representing such shares of the Series A Preferred Stock shall not have been surrendered at the office of the Corporation or that any such certificates evidencing such Conversion Shares shall not then be actually delivered to such Holder.

7.03 Mechanics of Automatic Conversion.

(a) Delivery of Book-Entry Statement Upon Automatic Conversion. Not later than three (3) Trading Days after the date of the Automatic Conversion, the Corporation shall deliver, or cause to be delivered, to the converting Holder a book-entry statement evidencing the number of Conversion Shares being acquired upon the Automatic Conversion (or, subject to Section 6(c), a stock certificate representing such Conversion Shares upon request of the Holder).

(b) Reservation of Shares Issuable Upon Conversion. The Corporation covenants that it will at all times reserve and keep available out of its authorized and unissued shares of Common Stock for the sole purpose of issuance upon conversion of the Series A Preferred Shares and payment of dividends on the Series A Preferred Shares, each as herein provided, free from preemptive rights or any other actual contingent purchase rights of Persons other than the Holder (and the other Holders of the Series A Preferred Shares), not less than such aggregate number of shares of the Common Stock as shall be issuable upon the conversion of the then outstanding shares of the Series A Preferred Shares. The Corporation covenants that all shares of the Common Stock that shall be so issuable shall, upon issue, be duly authorized, validly issued, fully paid and nonassessable.

(c) Fractional Shares. No fractional shares or scrip representing fractional shares shall be issued upon the conversion of the Series A Preferred Shares. As to any fraction of a share which the Holder would otherwise be entitled to receive upon such conversion, the Corporation shall or round up to the next whole share.

(d) Transfer Taxes and Expenses. The issuance of certificates for shares of the Common Stock on conversion of the Series A Preferred Shares shall be made without charge to any Holder for any documentary stamp or similar taxes that may be payable in respect of the issue or delivery of such certificates, provided that the Corporation shall not be required to pay any tax that may be payable in respect of any transfer involved in the issuance and delivery of any such certificate upon conversion in a name other than that of the Holders of such shares of the Series A Preferred Shares and the Corporation shall not be required to issue or deliver such certificates unless or until the Person or Persons requesting the issuance thereof shall have paid to the Corporation the amount of such tax or shall have established to the satisfaction of the Corporation that such tax has been paid.

(e) Status as Shareholder. Upon the Maturity Date, the Holder’s rights as a holder of such converted Series A Preferred Shares shall cease and terminate, excepting only the right to receive certificates for such shares of Common Stock.

Section 8.         Miscellaneous.

8.01           Book-Entry; Certificates. The Series A Preferred Stock will be issued in book-entry form; provided that, if a Holder requests that such Holder’s shares of the Series A Preferred Stock be issued in certificated form, the Corporation will instead issue a stock certificate to such Holder representing such Holder’s shares of the Series A Preferred Stock. To the extent that any shares of the Series A Preferred Stock are issued in book-entry form, references herein to “certificates” shall instead refer to the book-entry notation relating to such shares.

8.02 Exclusion of Other Rights. Except as may otherwise be required by law, the Series A Preferred Shares shall not have any voting powers, preferences and relative, participating, optional or other special rights, other than those specifically set forth in this Certificate of Designation, inclusive of those voting powers, preferences and relative, participating, option or other special rights set forth in the Purchase Agreement and incorporated herein by reference.

8.03          Registration of Transfer. The Corporation shall keep at its principal office a register for the registration of Series A Preferred Shares. Upon the surrender of any certificate representing Series A Preferred Stock at such place, the Corporation shall, at the request of the record Holder of such certificate, execute and deliver (at the Corporation’s expense) a new certificate or certificates in exchange therefor representing in the aggregate the number of Series A Shares represented by the surrendered certificate. Each such new certificate shall be registered in such name and shall represent such number of Series A Shares as is requested by the holder of the surrendered certificate and shall be substantially identical in form to the surrendered certificate, and dividends shall accrue on the Series A Preferred Shares represented by such new certificate from the date on which dividends have been fully paid on such Series A Preferred Shares represented by the surrendered certificate.

8.04 Record Holders. To the fullest extent permitted by applicable law, the Corporation may deem and treat the Holder of any Series A Preferred Shares as the true and lawful owner thereof for all purposes.

8.05          Notices. The Corporation shall send all notices or communications to Holders of the Series A Preferred Shares pursuant to this Certificate of Designation in writing by first class mail, certified or registered, return receipt requested, or by overnight air courier guaranteeing next day delivery, to the Holders’ respective addresses shown on the register for the Series A Preferred Shares.

8.06          No Preemptive Rights or Sinking Fund. The Holders will not be entitled to any preemptive or similar rights and will not have the benefit of any sinking fund.

8.07          Severability. If any portion of this Certificate of Designation shall be declared void or unenforceable by any court or administrative body of competent jurisdiction, such portion shall be deemed severable from the remainder of this Certificate of Designation, which shall continue in all respects valid and enforceable.

[Signature page follows]

IN WITNESS WHEREOF, the Corporation has caused this Certificate of Designation to be signed by the undersigned this 20th day of December, 2023.


	CONIFER HOLDINGS, INC.

	By:	/s/ Nicholas J. Petcoff


	Name:	Nicholas J. Petcoff
	Title:	Co-Chief Executive Officer

EXHIBIT A

To the CERTIFICATE OF DESIGNATION OF

SERIES A PREFERRED STOCK OF CONIFER HOLDINGS, INC.

Example of the Premium Amount if the Series A Dividend Rate is 10.0%

Dividend Rate 10.0%

Investment made on 12/15/23 $6,000,000


	12/15/23	3/15/24	6/15/24	9/15/24	12/15/24	3/15/25	6/15/25	9/15/25	12/15/25	Total

Years	-	0.25	0.50	0.75	1.00	1.25	1.50	1.75	2.00

Dividend		150,000	150,000	150,000	150,000	150,000	150,000	150,000	150,000	1,200,000

Redemption Premium		144,300	293,800	446,500	602,000	759,000	923,000	1,091,000	1,260,000	1,260,000

Initial investment		6,000,000	6,000,000	6,000,000	6,000,000	6,000,000	6,000,000	6,000,000	6,000,000
		6,144,300	6,293,800	6,446,500	6,602,000	6,759,000	6,923,000	7,091,000	7,260,000
		102%	105%	107%	110%	113%	115%	118%	121%
		0.25	0.50	0.75	1.00	1.25	1.50	1.75	2.00

Compounded Annualized Return on Redemption Premium		10.0%	10.0%	10.0%	10.0%	10.0%	10.0%	10.0%	10.0%
Return on Dividend Rate		10.0%	10.0%	10.0%	10.0%	10.0%	10.0%	10.0%	10.0%
Total Compounded Annualized Return		20.00%	20.00%	20.00%	20.00%	20.00%	20.00%	20.00%	20.00%

SECURITIES PURCHASE AGREEMENT

This Securities Purchase Agreement (this “Agreement”) is dated as of December 20, 2023 by and between Conifer Holdings Inc., a Michigan corporation (the “Company”), and Clarkston 91 West LLC, a Michigan limited liability company (“Purchaser”).

Recitals

Whereas, the Company and Purchaser are executing and delivering this Agreement in reliance upon the exemption from securities registration afforded by Section 4(a)(2) of the Securities Act of 1933, as amended (the “Securities Act”), and Rule 506 of Regulation D (“Regulation D”) as promulgated by the United States Securities and Exchange Commission (the “Commission”) under the Securities Act;

Whereas, the Company desires to issue to Purchaser, upon the terms and conditions stated in this Agreement, 1,000 shares of Series A Preferred Stock, no par value per share (“Series A Preferred Stock”), of the Company, for a purchase price of six million dollars ($6,000,000) (the “Series A Preferred Stock Payment”); and

Whereas, the shares of the Common Stock issuable upon conversion of the Series A Preferred Stock following receipt of the Shareholder Approval are collectively referred to herein as the “Underlying Shares,” and together with the Series A Preferred Stock, the “Securities.”

Agreement

NOW, THEREFORE, in consideration of the mutual covenants contained in this Agreement, and for other good and valuable consideration, the receipt and adequacy of which are hereby acknowledged, the Company and Purchaser hereby agree as follows:

ARTICLE I

DEFINITIONS

1.1

Definitions. In addition to the terms defined elsewhere in this Agreement, for all purposes of this Agreement, the following terms shall have the meanings indicated in this Section 1.1:

“Affiliate” means, with respect to any Person, any other Person that, directly or indirectly through one or more intermediaries, Controls, is controlled by or is under common control with such Person, as such terms are used in and construed under Rule 405 under the Securities Act. With respect to Purchaser, any investment fund or managed account that is managed on a discretionary basis by the same investment manager as Purchaser will be deemed to be an Affiliate of Purchaser.

“Board of Directors” means the Board of Directors of the Company.

“Business Day” means any day except Saturday, Sunday, any day which is a federal legal holiday in the United States or any day on which banking institutions in the State of New York are authorized or required by law or other governmental action to close.

“Certificate of Designation” means the Certificate of Designation of Series A Preferred Stock to be filed prior to the Closing by the Company with the Department of Licensing and Regulatory Affairs of the State of Michigan in the form of Exhibit A attached hereto.

“Closing” means the closing of the purchase and sale of the Series A Preferred Stock on the Closing Date pursuant to Section 2.1.

“Closing Date” means the Trading Day when all of the Transaction Documents have been executed and delivered by the applicable parties thereto, and all of the conditions set forth in Sections 2.1, 2.2, 5.1 and 5.2 hereof are satisfied or waived, as the case may be, or such other date as the parties may agree.

“Commission” has the meaning set forth in the Recitals.

“Common Stock” means the common stock, no par value per share, of the Company, and also includes any other class of securities into which the Common Stock may hereafter be reclassified or changed.

“Common Stock Equivalents” means any securities of the Company which would entitle the holder thereof to acquire at any time shares of the Common Stock, including, without limitation, any debt, preferred stock, rights, options, warrants or other instrument that is at any time convertible into or exchangeable for, or otherwise entitles the holder thereof to receive, shares of the Common Stock or other securities that entitle the holder to receive, directly or indirectly, shares of the Common Stock.

“Company Covered Person” means, with respect to the Company as an “issuer” for purposes of Rule 506 promulgated under the Securities Act, any Person listed in the first paragraph of Rule 506(d)(1).

“Company’s Knowledge” means with respect to any statement made to the Company’s Knowledge, that the statement is based upon the actual knowledge of the officers of the Company having responsibility for the matter or matters that are the subject of the statement, after reasonable inquiry.

“Control” (including the terms “controlling”, “controlled by” or “under common control with”) with respect to any Person means the possession, direct or indirect, of the power to direct or cause the direction of the management and policies of such Person, whether through the ownership of voting securities, by contract or otherwise.

“Exchange Act” means the Securities Exchange Act of 1934, as amended, or any successor statute, and the rules and regulations promulgated thereunder.

“Fundamental Transaction” means any event pursuant to which (a) the Company effects (i) any merger of the Company with (but not into) another Person, in which shareholders of the Company immediately prior to such transaction own less than a majority of the outstanding stock of the surviving entity, or (ii) any merger or consolidation of the Company into another Person, (b) the Company effects any sale of all or substantially all of its assets in one or a series of related transactions, (c) any tender offer or exchange offer approved or authorized by the

Company’s Board of Directors is completed pursuant to which holders of at least a majority of the outstanding Common Stock tender or exchange their shares for other securities, cash or property, or (d) the Company effects any reclassification of the Common Stock or any compulsory share exchange pursuant to which the Common Stock is effectively converted into or exchanged for other securities, cash or property (other than as a result of a subdivision or combination of shares of Common Stock covered by Section 6.11 below or as a result of a transaction, the primary purpose of which is to change the jurisdiction of incorporation of the Company).

“GAAP” means U.S. generally accepted accounting principles.

“Insolvent” means, with respect to any Person, (a) the present fair saleable value of such Person’s assets is less than the amount required to pay such Person’s debts as they become due, (b) such Person is unable to pay its debts and liabilities, subordinated, contingent or otherwise, as such debts and liabilities become absolute and matured or (c) such Person has unreasonably small capital with which to conduct the business in which it is engaged as such business is now conducted and is currently proposed to be conducted.

“Lien” means any lien, charge, claim, encumbrance, security interest, right of first refusal, preemptive right or other restrictions of any kind.

“Material Adverse Effect” means a material adverse effect on the results of operations, shareholders’ equity, assets, business or financial condition of the Company and its Subsidiaries taken as a whole, except that any of the following, either alone or in combination, shall not be deemed a Material Adverse Effect: (a) effects caused by changes or circumstances affecting general market conditions in the U.S. or applicable foreign economy or which are generally applicable to the industry in which the Company operates, provided that such effects are not borne disproportionately by the Company, or (b) effects caused by earthquakes, floods, hurricanes, wildfires or other large-scale natural disasters, hostilities, acts of war, sabotage or terrorism or military actions or any escalation or material worsening of any such hostilities, acts of war, sabotage or terrorism or military actions existing as of the date hereof.

“Material Contract” means any contract of the Company or a subsidiary of the Company that has been filed or was required to have been filed as an exhibit to the SEC Reports pursuant to Item 601(b)(4) or Item 601(b)(10) of Regulation S-K.

“Michigan Courts” means the state and federal courts with jurisdiction over Oakland County, Michigan.

“Person” means an individual, corporation, partnership, limited liability company, trust, business trust, association, joint stock company, joint venture, sole proprietorship, unincorporated organization, governmental authority or any other form of entity not specifically listed herein.

“Principal Trading Market” means the Trading Market on which the Common Stock is primarily listed on and quoted for trading, which, as of the date of this Agreement and the Closing Date, shall be the Nasdaq Capital Market.

“Proceeding” means an action, claim, suit, investigation or proceeding (including, without limitation, an investigation or partial proceeding, such as a deposition), whether commenced or threatened, before or by any federal, state, county, local or foreign court, arbitrator, governmental or administrative agency, regulatory authority, stock market, stock exchange or trading facility.

“Required Approvals” has the meaning set forth in Section 3.1(e) hereof.

“Rule 144” means Rule 144 promulgated by the Commission pursuant to the Securities Act, as such Rule may be amended from time to time, or any similar rule or regulation hereafter adopted by the Commission having substantially the same effect as such Rule.

“SEC Report” has the meaning set forth in Section 3.1(h) hereof.

“Series A Purchase Price” means $6,000 per share of Series A Preferred Stock.

“Subsidiary” means any subsidiary of the Company as set forth on Schedule 3.1(a), and shall, where applicable, include any subsidiary of the Company formed or acquired after the date hereof.

“Takeover Laws” shall have the meaning set forth in Section 7(d).

“Trading Day” means (i) a day on which the Common Stock is listed or quoted and traded on its Principal Trading Market (other than the OTCMarkets), or (ii) if the Common Stock is not listed on a Trading Market (other than the OTCMarkets), a day on which the Common Stock is traded in the over-the-counter market, as reported by the OTCMarkets, or (iii) if the Common Stock is not quoted on any Trading Market, a day on which the Common Stock is quoted in the over-the-counter market as reported in the OTCMarkets Pink Open Market (or any similar organization or agency succeeding to its functions of reporting prices); provided, that in the event that the Common Stock is not listed or quoted as set forth in (i), (ii) and (iii) hereof, then Trading Day shall mean a Business Day.

“Trading Market” means whichever of the New York Stock Exchange, the NYSE American, the Nasdaq Global Select Market, the Nasdaq Global Market, the Nasdaq Capital Market or the OTCMarkets on which the Common Stock is listed or quoted for trading on the date in question.

“Transaction Documents” means this Agreement, the schedules and exhibits attached hereto, the Certificate of Designation and any other documents or agreements explicitly contemplated hereunder.

ARTICLE II

PURCHASE AND SALE

2.1

Closing.

(a)

Sale of the Securities. At the Closing, subject to the terms and conditions set forth in this Agreement, the Company shall issue and sell to Purchaser, and Purchaser shall

purchase from the Company 1,000 shares of Series A Preferred Stock for a purchase price equal to six million dollars ($6,000,000).

(b)

Closing. The Closing of the purchase and sale of the Series A Preferred Stock shall take place at the offices of Honigman LLP, 2290 First National Building, 660 Woodward Avenue, Detroit, Michigan 48226-3506 on the Closing Date or at such other location(s) or remotely by facsimile transmission or other electronic means as the parties may mutually agree.

(c)

Deliverables. On the Closing Date, the Company and Purchaser shall deliver the other items set forth in Section 2.2 deliverable at the Closing.

2.2

Closing Deliveries.

(a)

Company Deliverables. On or prior to the Closing, the Company shall issue, deliver or cause to be delivered to Purchaser the following (the “Company Deliverables”):

(i)

for Purchaser, delivery, on the Closing Date, of the Series A Preferred Stock either in certificate or in book entry form;

(ii)

a certificate of the CEO of the Company, in the form attached hereto as Exhibit B, dated as of the Closing Date, (A) certifying the resolutions adopted by the Board of Directors or a duly authorized committee thereof approving the transactions contemplated by this Agreement and the other Transaction Documents and the issuance of the Underlying Shares, (B) certifying the current versions of the articles of incorporation, as amended, and bylaws, as amended, of the Company and (C) certifying as to the signatures and authority of persons signing the Transaction Documents and related documents on behalf of the Company; and

(iii)

evidence from the Department of Licensing and Regulatory Affairs of the State of Michigan that the Certificate of Designation has been filed with the Department of Licensing and Regulatory Affairs of the State of Michigan as of the Closing Date and has become effective as of the Closing Date.

(b)

Purchaser Deliverables. On or prior to the Closing, Purchaser shall deliver or cause to be delivered to the Company the following, with respect to Purchaser (the “Purchaser Deliverables”):

(i)

the Series A Purchase Price payable for the Purchased Series A Preferred Stock, in United States dollars and in immediately available funds by wire transfer to a bank account designated by the Company; and

(ii)

a fully completed and duly executed Accredited Investor Questionnaire in for form attached hereto as Exhibit C.

ARTICLE III

REPRESENTATIONS AND WARRANTIES

3.1

Representations and Warranties of the Company. Except as (i) set forth in the schedules delivered herewith (the “Disclosure Schedules”), which Disclosure Schedules shall be deemed a part hereof and shall qualify any representation made herein to the extent of the disclosure contained in the corresponding section of the Disclosure Schedules, or (ii) disclosed in the SEC Reports, the Company hereby represents and warrants as of the date hereof and the Closing Date (except for the representations and warranties that speak as of a specific date, which shall be made as of such date), to Purchaser:

(a)

Subsidiaries. The Company has no direct or indirect Subsidiaries other than those listed in Schedule 3.1(a) hereto. Except as disclosed in Schedule 3.1(a) hereto, the Company owns, directly or indirectly, all of the capital stock or comparable equity interests of each Subsidiary free and clear of any and all Liens, and all the issued and outstanding shares of capital stock or comparable equity interest of each Subsidiary are validly issued and are fully paid, non-assessable and free of preemptive and similar rights to subscribe for or purchase securities.

(b)

Organization and Qualification. The Company and each of its Subsidiaries is an entity duly incorporated or otherwise organized, validly existing and in good standing under the laws of the jurisdiction of its incorporation or organization (as applicable), with the requisite corporate (or other applicable) power and authority to own or lease and use its properties and assets and to carry on its business as currently conducted and, in the case of the Company, to enter into and to consummate the transactions contemplated by the Transaction Documents. Neither the Company nor any Subsidiary is in violation or default of any of the provisions of its certificate of incorporation or bylaws or other organizational documents. The Company and each of its Subsidiaries is duly qualified to conduct business and is in good standing as a foreign corporation or other entity in each jurisdiction in which the nature of the business conducted or property owned by it makes such qualification necessary, except where the failure to be so qualified or in good standing, as the case may be, would not have or reasonably be expected to result in a Material Adverse Effect or a material adverse effect on the legality, validity or enforceability of any Transaction Document or the Company’s ability to perform on a timely basis its material obligations under any Transaction Document; and no Proceeding has been instituted, is pending, or, to the Company’s Knowledge, has been threatened in any such jurisdiction revoking, limiting or curtailing or seeking to revoke, limit or curtail such power and authority or qualification.

(c)

Authorization; Enforcement; Validity. The Company has the requisite corporate power and authority to enter into and to consummate the transactions contemplated by each of the Transaction Documents and otherwise to carry out its obligations hereunder and thereunder. The Company’s execution and delivery of each of the Transaction Documents and the consummation by it of the transactions contemplated thereby (including, but not limited to, the sale and delivery of the Securities) have been duly authorized by all necessary corporate action on the part of the Company, and no further corporate action is required by the Company, its Board of Directors or its shareholders in connection therewith other than in connection with the Required Approvals. Each of the Transaction Documents to which the Company is a party has been (or upon delivery will have been) duly executed by the Company and is, or when delivered in accordance with the terms hereof, will constitute the legal, valid and binding obligation of the Company

enforceable against the Company in accordance with its terms, except (i) as such enforceability may be limited by applicable bankruptcy, insolvency, reorganization, moratorium, liquidation or similar laws relating to, or affecting generally the enforcement of, creditors’ rights and remedies or by other equitable principles of general application, (ii) as limited by laws relating to the availability of specific performance, injunctive relief or other equitable remedies and (iii) insofar as indemnification and contribution provisions may be limited by applicable law.

(d)

No Conflicts. The execution, delivery and performance by the Company of the Transaction Documents to which it is a party and the consummation by the Company of the transactions contemplated hereby or thereby (including, without limitation, the issuance of the Securities) do not and will not (i) conflict with or violate any provisions of the Company’s or any Subsidiary’s certificate of incorporation or bylaws, each as amended, or other similar organizational documents of any Subsidiary, (ii) conflict with, or constitute a default (or an event that with notice or lapse of time or both would result in a default) under, result in the creation of any Lien upon any of the properties or assets of the Company or any Subsidiary or give to others any rights of termination, amendment, acceleration or cancellation (with or without notice, lapse of time or both) of, any Material Contract, or (iii) subject to the Required Approvals, conflict with or result in a violation of any law, rule, regulation, order, judgment, injunction, decree or other restriction of any court or governmental authority to which the Company or a Subsidiary is subject (including federal and state securities laws and regulations and the rules and regulations, assuming the correctness of the representations and warranties made by Purchaser herein, of any self-regulatory organization to which the Company or its securities are subject, including all applicable Trading Markets), or by which any property or asset of the Company is bound or affected, except in the case of clauses (ii) and (iii) such as would not, individually or in the aggregate, have or reasonably be expected to result in a Material Adverse Effect or a material adverse effect on the legality, validity or enforceability of any Transaction Document or the Company’s ability to perform on a timely basis its material obligations under any Transaction Document.

(e)

Filings, Consents and Approvals. Neither the Company nor any of its Subsidiaries is required to obtain any consent, waiver, approval, authorization or order of, give any notice to, or make any filing or registration with, any court or other federal, state, local or other governmental authority, holder of outstanding securities of the Company or other Person in connection with the execution, delivery and performance by the Company of the Transaction Documents (including the issuance of the Securities), other than (i) the filing with the Commission of the Registration Statements in accordance with the requirements of the Transaction Documents, (ii) filings required by applicable state securities laws, (iii) the filing of a Notice of Sale of Securities on Form D with the Commission under Regulation D under the Securities Act, (iv) the filing of any requisite notices and/or application(s) to the Principal Trading Market for the issuance and sale of the Securities and the listing of the Underlying Shares for trading or quotation, as the case may be, thereon in the time and manner required thereby, (v) the filings required in accordance with Section 4.6 of this Agreement, (vi) the Shareholder Approval, (vii) the filing of the Certificates of Designation with the Secretary of State of the State of Delaware and (viii) those that have been made or obtained prior to the date of this Agreement (collectively, the “Required Approvals”).

(f)

Issuance of the Shares. The Securities have been duly authorized and, when issued and paid for in accordance with the terms of the Transaction Documents, will be, in the case

of the Shares, duly and validly issued, fully paid and non-assessable and will be free and clear of all Liens, other than restrictions on transfer set forth in Section 4.1 hereof or imposed by applicable securities laws, and shall not be subject to preemptive or similar rights of shareholders. Assuming the accuracy of the representations and warranties of Purchaser in this Agreement, the Securities will be issued in compliance with all applicable federal and state securities laws. No “bad actor” disqualifying event described in Rule 506(d)(1)(i)-(viii) of the Securities Act (a “Disqualification Event”) is applicable to the Company or, to the Company’s knowledge, any Company Covered Person, except for a Disqualification Event as to which Rule 506(d)(2)(ii–iv) or (d)(3), is applicable.

(g)

Capitalization. The capitalization of the Company is as described in its SEC Report on Form 10-Q for the quarter ended September 30, 2023, except for issuances pursuant to this Agreement, stock option exercises, restricted stock unit delivery, issuances pursuant to equity incentive plans described in the SEC Reports or exercises of warrants, or issuances of warrants. The Company has not issued any capital stock since the date of its most recently filed SEC Report. No Person has any right of first refusal, preemptive right, right of participation, or any similar right to participate in the transactions contemplated by the Transaction Documents that have not been effectively waived as of the Closing Date. Except as set described in the SEC Reports or as a result of the purchase and sale of the Securities, there are no outstanding options, warrants, scrip rights to subscribe to, calls or commitments of any character whatsoever relating to, or securities, rights or obligations convertible into or exercisable or exchangeable for, or giving any Person any right to subscribe for or acquire any shares of the Common Stock or other securities, or contracts, commitments, understandings or arrangements by which the Company or any Subsidiary is or may become bound to issue additional shares of the Common Stock or any Common Stock Equivalents. The issuance and sale of the Securities will not obligate the Company to issue shares of the Common Stock or other securities to any Person (other than Purchaser) and will not result in a right of any holder of the Company’s securities to adjust the exercise, conversion, exchange or reset price under any of such securities. All of the outstanding shares of capital stock of the Company are validly issued, fully paid and non-assessable, have been issued in compliance in all material respects with all applicable federal and state securities laws, and none of such outstanding shares was issued in violation of any preemptive rights or similar rights to subscribe for or purchase securities which violation would have or would reasonably be expected to result in a Material Adverse Effect or a material adverse effect on the legality, validity or enforceability of any Transaction Document or the Company’s ability to perform in any material respect on a timely basis its obligations under any Transaction Document. Except as set forth in the SEC Filings, there are no shareholders agreements, voting agreements or other similar agreements with respect to the Company’s capital stock to which the Company is a party or, to the Company’s Knowledge, between or among any of the Company’s shareholders.

(h)

SEC Reports; Disclosure Materials. The Company has filed all reports, schedules, forms, statements and other documents required to be filed by it under the Exchange Act, including pursuant to Section 13(a) or 15(d) thereof, for the 12 months preceding the date hereof (or such shorter period as the Company was required by law or regulation to file such material) (the foregoing materials, including the exhibits thereto and documents incorporated by reference therein and the exhibits thereto and documents incorporated by reference therein, being collectively referred to herein as the “SEC Reports”, and the SEC Reports, together with the Disclosure Schedules, being collectively referred to as the “Disclosure Materials”) on a timely

basis or has received a valid extension of such time of filing and has filed any such SEC Reports prior to the expiration of any such extension, except where the failure to file on a timely basis would not have or reasonably be expected to result in a Material Adverse Effect and would not have or reasonably be expected to result in any limitation or prohibition, or with respect to Rule 144 further delay, on the Company’s ability to register the Underlying Shares for resale on Form S-1 or Purchaser’s ability to use Rule 144 to resell any of the Underlying Shares. As of their respective filing dates, or to the extent corrected by a subsequent amendment, the SEC Reports complied in all material respects with the requirements of the Securities Act and the Exchange Act and the rules and regulations of the Commission promulgated thereunder, and none of the SEC Reports, when filed, contained any untrue statement of a material fact or omitted to state a material fact required to be stated therein or necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading. Each of the Material Contracts to which the Company or any Subsidiary is a party or to which the property or assets of the Company or any of its Subsidiaries are subject has been filed (or incorporated by reference) as an exhibit to the SEC Reports.

(i)

Financial Statements. The consolidated financial statements (including the notes and schedules thereto) of the Company included in the SEC Reports comply in all material respects with applicable accounting requirements and the rules and regulations of the Commission with respect thereto as in effect at the time of filing (or to the extent corrected by a subsequent amendment). Such consolidated financial statements have been prepared in accordance with GAAP applied on a consistent basis during the periods involved, except as may be otherwise specified in such financial statements or the notes or schedules thereto and except that unaudited financial statements may not contain all footnotes required by GAAP, and fairly present in all material respects, for the Company and its consolidated Subsidiaries taken as a whole, their financial position as of the dates thereof and their results of operations and cash flows for the periods then ended, subject, in the case of unaudited financial statements, to normal, immaterial year-end audit adjustments.

(j)

Private Placement. Assuming the accuracy of Purchaser’s representations and warranties set forth in Section 3.3 of this Agreement, no registration under the Securities Act is required for the offer and sale of the Securities by the Company to Purchaser under the Transaction Documents. Subject to obtaining the Required Approvals, the issuance and sale of the Securities hereunder does not contravene the rules and regulations of the Principal Trading Market.

(k)

No General Solicitation. Neither the Company nor, to the Company’s Knowledge, any Person acting on behalf of the Company has offered or sold any of the Securities by any form of general solicitation or general advertising.

3.2

Anti-Takeover Provisions. The Company has taken all actions necessary to render inapplicable to this Agreement and the transactions contemplated hereby, and inapplicable to Purchaser or any Affiliate thereof, the Underlying Shares or the transactions contemplated hereby, any and all “fair price,” “moratorium,” “control share acquisition,” “business combination” and other similar restrictions set forth in statutes or regulations of any state or jurisdiction (collectively, “Takeover Laws”), and no Takeover Law applies or will apply to the Company or any Subsidiary, this Agreement or the transactions contemplated hereby

3.3

Representations and Warranties of Purchaser. Purchaser hereby represents and warrants as of the date hereof and as of the Closing Date to the Company as follows:

(a)

Organization; Authority. Purchaser is an entity duly organized, validly existing and in good standing under the laws of the jurisdiction of its organization with the requisite corporate, limited liability company or partnership power and authority to enter into and to consummate the transactions contemplated by the applicable Transaction Documents and otherwise to carry out its obligations thereunder. The execution and delivery of by Purchaser of the Transaction Documents to which it is a party and performance by Purchaser of the transactions contemplated by the Transaction Documents to which it is a party have been duly authorized by all necessary corporate or, if Purchaser is not a corporation, such partnership, limited liability company or other applicable like action, on the part of Purchaser. Each Transaction Document to which it is a party has been duly executed by Purchaser, and when delivered by Purchaser in accordance with the terms hereof, will constitute the legal, valid and binding obligation of Purchaser, enforceable against it in accordance with its terms, except (i) as such enforceability may be limited by applicable bankruptcy, insolvency, reorganization, moratorium, liquidation or similar laws relating to, or affecting generally the enforcement of, creditors’ rights and remedies or by other equitable principles of general application and (ii) as limited by laws relating to the availability of specific performance, injunctive relief or other equitable remedies.

(b)

No Conflicts. The execution, delivery and performance by Purchaser of this Agreement and the consummation by Purchaser of the transactions contemplated hereby and thereby will not (i) result in a violation of the organizational documents of Purchaser, (ii) conflict with, or constitute a default (or an event which with notice or lapse of time or both would result in a default) under, or give to others any rights of termination, amendment, acceleration or cancellation of, any agreement, indenture or instrument to which Purchaser is a party, or (iii) result in a violation of any law, rule, regulation, order, judgment or decree (including, assuming the correctness of the Company’s representations and warranties contained herein, federal and state securities laws) applicable to Purchaser, except in the case of clauses (ii) and (iii) above, for such conflicts, defaults, rights or violations which would not, individually or in the aggregate, reasonably be expected to have a material adverse effect on the ability of Purchaser to perform its obligations hereunder.

(c)

Investment Intent. Purchaser understands that the Securities are “restricted securities” and have not been registered under the Securities Act or any applicable state securities law and is acquiring the Securities as principal for its own account and not with a view to, or for distributing or reselling such Securities or any part thereof in violation of the Securities Act or any applicable state securities laws, provided, however, that by making the representations herein, Purchaser does not agree to hold any of the Securities for any minimum period of time and reserves the right, subject to the provisions of this Agreement, at all times to sell or otherwise dispose of all or any part of such Securities pursuant to an effective registration statement under the Securities Act or under an exemption from such registration and in compliance with applicable federal and state securities laws. Purchaser is acquiring the Securities hereunder in the ordinary course of its business. Except as contemplated by the Registration Statements to be filed by the Company pursuant to the terms thereof, Purchaser does not presently have any agreement, plan or understanding, directly or indirectly, with any Person to distribute or effect any distribution of any of the Securities to or through any Person; Purchaser is not a registered broker-dealer under Section

15 of the Exchange Act or an entity engaged in a business that would require it to be so registered as a broker-dealer.

(d)

Purchaser Status. At the time Purchaser was offered the Securities, it was, and at the date hereof it is, an “accredited investor” as defined in Rule 501(a) under the Securities Act.

(e)

General Solicitation. Purchaser is not purchasing the Securities as a result of any advertisement, article, notice or other communication regarding the Securities published in any newspaper, magazine or similar media or broadcast over television or radio or presented at any seminar or any other general advertisement.

(f)

Experience of Purchaser. Purchaser, either alone or together with its representatives, has such knowledge, sophistication and experience in business and financial matters so as to be capable of evaluating the merits and risks of the prospective investment in the Securities, and has so evaluated the merits and risks of such investment. Purchaser is able to bear the economic risk of an investment in the Securities and, at the present time, is able to afford a complete loss of such investment.

(g)

Access to Information. Purchaser acknowledges that it has had the opportunity to review the Disclosure Materials and has been afforded the opportunity to ask such questions as it has deemed necessary of, and to receive answers from, representatives of the Company concerning the terms and conditions of the offering of the Securities. Neither such inquiries nor any other investigation conducted by or on behalf of Purchaser or its representatives or counsel shall modify, amend or affect Purchaser’s right to rely on the truth, accuracy and completeness of the Company’s representations and warranties contained in the Transaction Documents.

(h)

Brokers and Finders. No Person will have, as a result of the transactions contemplated by this Agreement, any valid right, interest or claim against or upon the Company or Purchaser for any commission, fee or other compensation pursuant to any agreement, arrangement or understanding entered into by or on behalf of Purchaser.

(i)

Independent Investment Decision. Purchaser has independently evaluated the merits of its decision to enter into the Transaction Documents, and Purchaser confirms that it has not relied on the advice of any other non-affiliated Purchaser’s investment manager and/or legal counsel in making such decision. Purchaser understands that nothing in this Agreement or any other materials presented by or on behalf of the Company to the Purchaser in connection with the purchase of the Securities constitutes legal, tax or investment advice. Purchaser has consulted such legal, tax and investment advisers as it, in its sole discretion, has deemed necessary or appropriate in connection with its purchase of the Securities.

(j)

Reliance on Exemptions. Purchaser understands that the Securities are being offered and sold to it in reliance on specific exemptions from the registration requirements of United States federal and state securities laws and that the Company is relying in part upon the truth and accuracy of, and Purchaser’s compliance with, the representations, warranties, agreements, acknowledgements and understandings of Purchaser set forth herein in order to

determine the availability of such exemptions and the eligibility of Purchaser to acquire the Securities.

The Company and Purchaser acknowledge and agree that no party to this Agreement has made or makes any representations or warranties with respect to the transactions contemplated hereby other than those specifically set forth in this Article III and the Transaction Documents.

ARTICLE IV

OTHER AGREEMENTS OF THE PARTIES

4.1

Transfer Restrictions.

(a)

Compliance with Securities Laws. Notwithstanding any other provision of this Article IV, Purchaser covenants that the Securities acquired by Purchaser pursuant to the Transaction Documents may be disposed of only pursuant to an effective registration statement under, and in compliance with the requirements of, the Securities Act, or pursuant to an available exemption from, or in a transaction not subject to, the registration requirements of the Securities Act, and in compliance with any applicable state and federal securities laws. In connection with any transfer of the Securities other than (i) pursuant to an effective registration statement, (ii) to the Company, (iii) pursuant to Rule 144 (once Rule 144 becomes available for the resale of securities of the Company and provided that Purchaser provides the Company with reasonable assurances (in the form of seller and, if applicable, broker representation letters) that the securities may be sold pursuant to such rule) or (iv) in connection with a bona fide pledge as contemplated in Section 4.1(b), the Company may require the transferor thereof to provide to the Company an opinion of counsel selected by the transferor and reasonably acceptable to the Company, the form and substance of which opinion shall be reasonably satisfactory to the Company, to the effect that such transfer does not require registration of such transferred Securities under the Securities Act. As a condition of transfer, any such transferee in a transaction not referenced in clauses (i)-(iv) above shall agree in writing to be bound by the terms of this Agreement and shall have the rights of Purchaser under this Agreement with respect to such transferred Securities.

(b)

Legends. Book-entry statements or stock certificates evidencing the Securities shall bear any legend as required by the “blue sky” laws of any state and a restrictive legend in substantially the following form, until such time as they are not required under Section 4.1(c):

[NEITHER THESE SECURITIES NOR THE SECURITIES ISSUABLE UPON CONVERSION OF THESE SECURITIES HAVE BEEN REGISTERED] [THESE SECURITIES HAVE NOT BEEN REGISTERED] UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “SECURITIES ACT”), OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED (I) IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR THE SECURITIES UNDER THE SECURITIES ACT OR (B) AN AVAILABLE EXEMPTION FROM, OR IN A TRANSACTION NOT SUBJECT TO, THE REGISTRATION REQUIREMENTS OF THE SECURITIES ACT AND IN ACCORDANCE WITH APPLICABLE STATE SECURITIES LAWS OR BLUE

SKY LAWS AS EVIDENCED BY A LEGAL OPINION OF COUNSEL REASONABLY SATISFACTORY TO THE COMPANY AND ITS TRANSFER AGENT, (II) UNLESS SOLD PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OR (III) UNLESS SOLD TO THE COMPANY.

The Company acknowledges and agrees that Purchaser may from time to time pledge, and/or grant a security interest in, some or all of the legended Securities in connection with applicable securities laws, pursuant to a bona fide margin agreement in compliance with a bona fide margin loan. Such a pledge would not be subject to approval or consent of the Company and no legal opinion of legal counsel to the pledgee, secured party or pledgor shall be required in connection with the pledge, but such legal opinion shall be required in connection with a subsequent transfer or foreclosure following default by Purchaser transferee of the pledge. No notice shall be required of such pledge, but Purchaser’s transferee shall promptly notify the Company of any such subsequent transfer or foreclosure of such legended Securities. Purchaser acknowledges that the Company shall not be responsible for any pledges relating to, or the grant of any security interest in, any of the Securities or for any agreement, understanding or arrangement between Purchaser and its pledgee or secured party. At the appropriate Purchaser’s expense, the Company will execute and deliver such reasonable documentation as a pledgee or secured party of Securities may reasonably request in connection with a pledge or transfer of the Securities, including the preparation and filing of any required prospectus supplement under Rule 424(b)(3) under the Securities Act or other applicable provision of the Securities Act and the regulations promulgated to appropriately amend the list of selling shareholders thereunder. Purchaser acknowledges and agrees that, except as otherwise provided in Section 4.1(c), any Securities subject to a pledge or security interest as contemplated by this Section 4.1(b) shall continue to bear the legend set forth in this Section 4.1(b) and be subject to the restrictions on transfer set forth in Section 4.1(a).

(c)

Removal of Legends. The legend set forth in Section 4.1(b) above shall be removed and the Company shall issue a certificate or book entry statement representing the applicable Securities, without any legend, if (i) such Securities are registered for resale under the Securities Act, (ii) such Securities are sold or transferred pursuant to Rule 144 (if the transferor is not an Affiliate of the Company), or (iii) such Securities are eligible for sale under Rule 144, without the requirement for the Company to be in compliance with the current public information required under Rule 144 as to such securities and without volume or manner-of-sale restrictions.

(d)

Acknowledgement. Purchaser acknowledges its primary responsibilities under the Securities Act and accordingly will not sell or otherwise transfer the Securities or any interest therein without complying with the requirements of the Securities Act and applicable law.

4.2

Reservation of Shares of the Common Stock. The Company shall reserve and keep available at all times during which any of the shares of the Preferred Stock remain outstanding, free of preemptive rights, a sufficient number of shares of the Common Stock for the purpose of enabling the Company to issue the Underlying Shares upon conversion of the shares of the Preferred Stock.

4.3

Securities Laws Disclosure; Publicity. On or before 9:00 a.m., Eastern time, on the Business Day immediately following the date hereof, the Company shall issue a press

release (the “Press Release”) reasonably acceptable to Purchaser disclosing all material terms of the transactions contemplated hereby. On or before 5:30 p.m., Eastern time, on the fourth Trading Day immediately following the execution of this Agreement, the Company will file a Current Report on Form 8-K with the Commission describing the terms of the Transaction Documents (and including as exhibits to such Current Report on Form 8-K the material Transaction Documents. Notwithstanding the foregoing, the Company shall not publicly disclose the name of Purchaser, any Affiliate of Purchaser, or any investment adviser of Purchaser, or include the name of Purchaser, any Affiliate of Purchaser or any investment adviser of Purchaser in any press release or filing with the Commission (other than the Registration Statements) or any regulatory agency or Trading Market, without the prior written consent of Purchaser, except (i) as required by federal securities law in connection with (A) the Registration Statements and (B) the filing of final Transaction Documents (including signature pages thereto) with the Commission and (ii) to the extent such disclosure is required by law, request of the staff of the Commission or Trading Market regulations, in which case the Company shall provide Purchaser with prior written notice of such disclosure permitted under this clause (ii).

4.4

Shareholder Rights Plan. No claim will be made or enforced by the Company or, with the consent of the Company, any other Person, that Purchaser is an “Acquiring Person” under any control share acquisition, business combination, poison pill (including any distribution under a rights agreement) or similar anti-takeover plan or arrangement in effect or hereafter adopted by the Company, or that Purchaser could be deemed to trigger the provisions of any such plan or arrangement, in either case solely by virtue of receiving any of the Underlying Shares under the Transaction Documents or under any other written agreement between the Company and Purchaser.

4.5

Use of Proceeds. The Company shall use the net proceeds from the sale of the Purchased Series A Preferred Stock hereunder for working capital and general corporate purposes.

4.6

Form D; Blue Sky. The Company agrees to timely file a Form D with respect to the Securities as required under Regulation D and to provide a copy thereof, promptly upon the written request of Purchaser. The Company, on or before the Closing Date, shall take such action as the Company shall reasonably determine is necessary in order to obtain an exemption for or to qualify the Securities for sale to Purchaser at the Closing pursuant to this Agreement under applicable securities or “Blue Sky” laws of the states of the United States (or to obtain an exemption from such qualification) and shall provide evidence of such actions promptly upon the written request of Purchaser.

4.7

Indemnification of Purchaser.

(a)

Indemnification. Subject to the provisions of this Section 4.7, the Company will indemnify and hold harmless Purchaser and its Affiliates, directors, officers, shareholders, members, partners, managers, employees, representatives, investment advisers and agents (and any other Persons with a functionally equivalent role of a Person holding such titles notwithstanding a lack of such title or any other title), each Person who controls Purchaser (within the meaning of Section 15 of the Securities Act and Section 20 of the Exchange Act), and the directors, officers, shareholders, members, partners, managers, employees, representatives, investment advisers and agents (and any other Persons with a functionally equivalent role of a

Person holding such titles notwithstanding a lack of such title or any other title) of each such controlling Person (each, a “Purchaser Party”), to the fullest extent permitted by applicable law, from and against, and shall pay and reimburse them for, any and all losses, liabilities, obligations, claims, contingencies, damages, costs and expenses (including, without limitation, all judgments, amounts paid in settlements, court costs and reasonable attorneys’ fees and costs of investigation) (collectively, “Losses”), as incurred, that any Purchaser Party may suffer or incur as a result of, based upon, arising out of or otherwise relating to (i) any inaccuracy in or breach of any of the representations or warranties of, or breach or nonfulfillment of any of covenants or agreements made by, the Company in any Company or (ii) any Proceeding instituted against Purchaser in any capacity, or any Purchaser Party, by any Person who is not an Affiliate of Purchaser or other Purchaser Party seeking indemnification, with respect to any of the transactions contemplated by the Transaction Documents (unless, and only to the extent that, such Proceeding is based upon a breach of Purchaser’s representations, warranties or covenants under the Transaction Documents or any other agreement with the Company entered into in connection with the transactions contemplated hereby, or any violations by the Purchaser of state or federal securities laws or any conduct by Purchaser which constitutes fraud, gross negligence or willful misconduct).

(b)

Procedures. Promptly after receipt by any Purchaser Party (the “Indemnified Person”) of notice of any demand, claim or circumstances which would or might give rise to a claim or the commencement of any Proceeding in respect of which indemnity may be sought pursuant to this Section 4.7, such Indemnified Person shall promptly notify the Company in writing and the Company shall assume the defense thereof, including the employment of counsel reasonably satisfactory to such Indemnified Person, and shall assume the payment of all fees and expenses relating to such Proceeding; provided, however, that the failure of any Indemnified Person so to notify the Company shall not relieve the Company of its obligations hereunder except to the extent that the Company is actually and materially prejudiced in the defense of such Proceeding by such failure to notify. Notwithstanding the foregoing, in any such Proceeding, any Indemnified Person shall have the right to retain its own counsel, but the fees and expenses of such counsel shall be at the expense of such Indemnified Person; provided, that such fees and expenses shall be paid by the Company if (i) the Company and the Indemnified Person shall have mutually agreed to the retention of such counsel, (ii) the Company shall have failed promptly to assume the defense of such Proceeding and to employ counsel reasonably satisfactory to such Indemnified Person in such Proceeding or (iii) in the reasonable judgment of counsel to such Indemnified Person, representation of both parties by the same counsel would be inappropriate due to actual or potential differing interests between them. The Company shall not be liable for (i) any settlement by an Indemnified Person of any Proceeding effected without the Company’s prior written consent (which consent shall not be unreasonably withheld, delayed or conditioned) or (ii) fees or costs incurred pursuant to this Section 4.7 to the extent such fees or costs are attributable to the Indemnified Person’s breach of any of the representations, warranties, covenants or agreements made by Purchaser in this Agreement or the other Transaction Documents. Without the prior written consent of the Indemnified Person (which consent shall not be unreasonably withheld, delayed or conditioned), the Company shall not effect any settlement of any pending or threatened Proceeding in respect of which any Indemnified Person is or could have been a party and indemnity could have been sought hereunder by such Indemnified Person, unless such settlement includes an unconditional release of such Indemnified Person from all liability arising out of such Proceeding.

(c)

Payments. Once a Loss is agreed to by the Company or finally adjudicated to be payable to an Indemnified Person pursuant to this Section 4.7, the Company shall satisfy its indemnification obligations to such Indemnified Person within 15 days of such agreement or final adjudication by wire transfer of immediately available funds to such Indemnified Person in accordance with wire transfer instructions to be provided by such Indemnified Person.

ARTICLE V

CONDITIONS PRECEDENT TO CLOSING

5.1

Conditions Precedent to the Obligations of Purchaser to Purchase the Securities. The obligation of Purchaser to acquire the Securities at the Closing is subject to the fulfillment to Purchaser’s satisfaction, on or prior to the Closing Date, of each of the following conditions, any of which may be waived by Purchaser:

(a)

Representations and Warranties. The representations and warranties of the Company contained herein shall be true and correct in all material respects (except for those representations and warranties which are qualified as to materiality, in which case such representations and warranties shall be true and correct in all respects) as of the date when made and as of the Closing Date, as though made on and as of such date, except for such representations and warranties that speak as of a specific date.

(b)

Performance. The Company shall have performed, satisfied and complied in all material respects with all covenants, agreements and conditions required by the Transaction Documents to be performed, satisfied or complied with by it at or prior to the Closing.

(c)

No Injunction. No statute, rule, regulation, executive order, decree, ruling or injunction shall have been enacted, entered, promulgated or endorsed by any court or governmental authority of competent jurisdiction that prohibits the consummation of any of the transactions contemplated by the Transaction Documents.

(d)

Consents. The Company shall have obtained in a timely fashion any and all consents, permits, approvals, registrations, waivers and the Required Approvals that are necessary for consummation of the purchase and sale of the Securities at the Closing, all of which shall be and remain so long as necessary in full force and effect. For the avoidance of doubt, any of the Required Approvals, including without limitation the Shareholder Approval, that are not necessary for the consummation of the purchase and sale of the Securities at the Closing shall not be required by this Section 5.1(d).

(e)

Company Deliverables. The Company shall have delivered the Company Deliverables in accordance with Section 2.2(a).

(f)

Compliance Certificate. The Company shall have delivered to Purchaser a certificate, dated as of the Closing Date and signed by its Chief Executive Officer, certifying to the fulfillment of the conditions specified in Sections 5.1(a), (b) and (e).

5.2

Conditions Precedent to the Obligations of the Company to sell the Securities. The Company’s obligation to sell and issue the Securities at the Closing to Purchaser

is subject to the fulfillment to the satisfaction of the Company on or prior to the Closing Date of the following conditions, any of which may be waived by the Company:

(a)

Representations and Warranties. The representations and warranties made by Purchaser in Section 3.3 hereof shall be true and correct in all material respects (except for those representations and warranties which are qualified as to materiality, in which case such representations and warranties shall be true and correct in all respects) as of the date when made, and as of the Closing Date as though made on and as of such date, except for such representations and warranties that speak as of a specific date.

(b)

Performance. Purchaser shall have performed, satisfied and complied in all material respects with all covenants, agreements and conditions required by the Transaction Documents to be performed, satisfied or complied with by Purchaser at or prior to the Closing Date.

(c)

(d)

Consents. The Company shall have obtained in a timely fashion any and all consents, permits, approvals, registrations, waivers and the Required Approvals that are necessary for consummation of the purchase and sale of the Securities at the Closing, all of which shall be and remain so long as necessary in full force and effect. For the avoidance of doubt, any of the Required Approvals, including, without limitation, the Shareholder Approval, that are not necessary for the consummation of the purchase and sale of the Securities at the Closing shall not be required by this Section 5.2(d).

(e)

Purchaser Deliverables. Purchaser shall have delivered its Purchaser Deliverables in accordance with Section 2.2(b).

ARTICLE VI

MISCELLANEOUS

6.1

Fees and Expenses. The Company and Purchaser shall pay the fees and expenses of their respective advisers, counsel, accountants and other experts, if any, and all other expenses incurred by such party in connection with the negotiation, preparation, execution, delivery and performance of this Agreement. The Company shall pay any transfer agent fees, stamp taxes and other taxes and duties levied in connection with the sale and issuance of the Securities to Purchaser. Purchaser shall be responsible for all other tax liability that may arise as a result of holding or transferring the Securities purchased by it.

6.2

Entire Agreement. The Transaction Documents, together with the exhibits and schedules thereto, and any confidentiality or nondisclosure agreement entered into between Purchaser and the Company prior to the date of this Agreement with respect to the transactions contemplated thereby, contain the entire understanding of the parties with respect to the subject matter hereof and supersede all prior agreements, understandings, discussions and representations, oral or written, with respect to such matters, which the parties acknowledge have been merged into

such documents, exhibits and schedules. At or after the Closing, and without further consideration, the Company and Purchaser will execute and deliver to the other such further documents as may be reasonably requested in order to give practical effect to the intention of the parties under the Transaction Documents.

6.3

Notices. Any and all notices or other communications or deliveries required or permitted to be provided hereunder shall be in writing and delivered personally, by email, by facsimile or sent by a nationally recognized overnight courier service. Any notice or other communications or deliveries hereunder shall be deemed given and effective on the earliest of (a) the date of transmission, if such notice or communication is delivered via email to the email address set forth in this Section 6.3, (b) the date of transmission, if such notice or communication is delivered via facsimile (provided the sender receives a machine-generated confirmation of successful transmission) at the facsimile number set forth in this Section 6.3 prior to 5:30 p.m. (Eastern time) on any Trading Day, (c) the next Trading Day after the date of transmission, if such notice or communication is delivered via facsimile at the facsimile number set forth in this Section 6.3 on a day that is not a Trading Day or later than 5:30 p.m. Eastern time) on any Trading Day, (d) the Trading Day following the date of mailing, if sent by U.S. nationally recognized overnight courier service with next day delivery specified or (e) upon actual receipt by the party to whom such notice is required to be given. The address for such notices and communications shall be as follows:

If to the Company: Conifer Holdings Inc.

3001 West Big Beaver Road

Troy, Michigan 48084

Telephone No.: (248) 559-0840

Attention: Chief Executive Officer

Email: npetcoff@cnfrh.com

With a copy to (which shall not constitute notice):

Honigman LLP

2290 First National Building

660 Woodward Avenue

Detroit, Michigan 48226-3506

Telephone No.: 269.337.7702

Attention: Donald J. Kunz, Esq.

Email: dkunz@honigman.com

If to Purchaser: Clarkston 91 West LLC

303 E 3rd Street #110

Rochester, Michigan 48307

Attn.:

Telephone:

With a copy to (which shall not constitute notice):

Kerr Russell

500 Woodward Avenue, Suite 2500

Detroit, Michigan 48226

Telephone no.: 313.961.0200

Attention: John D. Gatti

Email: jgatti@kerr-russell.com

6.4

Amendments; Waivers; No Additional Consideration. No provision of this Agreement may be waived, modified, supplemented or amended except in a written instrument signed, in the case of an amendment, by the Company and Purchaser, in the case of a waiver, by the party against whom enforcement of any such waived provision is sought. No waiver of any default with respect to any provision, condition or requirement of this Agreement shall be deemed to be a continuing waiver in the future or a waiver of any subsequent default or a waiver of any other provision, condition or requirement hereof, nor shall any delay or omission of any party to exercise any right hereunder in any manner impair the exercise of any such right. Any amendment effected in accordance with this Section 6.4 shall be binding upon Purchaser and the Company.

6.5

Construction. The headings herein are for convenience only, do not constitute a part of this Agreement and shall not be deemed to limit or affect any of the provisions hereof. The language used in this Agreement will be deemed to be the language chosen by the parties to express their mutual intent, and no rules of strict construction will be applied against any party. This Agreement shall be construed as if drafted jointly by the parties, and no presumption or burden of proof shall arise favoring or disfavoring any party by virtue of the authorship of any provisions of this Agreement or any of the Transaction Documents.

6.6

Successors and Assigns. The provisions of this Agreement shall inure to the benefit of and be binding upon the parties and their successors and permitted assigns. This Agreement, or any rights or obligations hereunder, may not be assigned by the Company without the written consent of Purchaser except to a successor in the event of a Fundamental Transaction. Purchaser may assign its rights hereunder in whole or in part to any Person to whom Purchaser assigns or transfers any Underlying Shares in compliance with the Transaction Documents and applicable law (including in connection with a bona fide margin account or other loan or financing arrangement secured by such Underlying Shares), provided that such transferee shall agree in writing to be bound, with respect to the transferred Underlying Shares, by the terms and conditions of this Agreement that apply to Purchaser.

6.7

No Third-Party Beneficiaries. This Agreement is intended for the benefit of the parties hereto and their respective successors and permitted assigns and is not for the benefit of, nor may any provision hereof be enforced by, any other Person.

6.8

Survival. Subject to applicable statute of limitations, the representations, warranties agreements and covenants contained herein shall survive the Closing and the delivery of the Securities and any confidentiality or nondisclosure obligations set forth in any agreement entered into between the Company and Purchaser prior to the date of this Agreement with respect

to the transactions contemplated by the Transaction Documents shall survive according to the terms of such agreement(s).

6.9

Execution. This Agreement may be executed in two or more counterparts, all of which when taken together shall be considered one and the same agreement and shall become effective when counterparts have been signed by each party and delivered to the other party, it being understood that both parties need not sign the same counterpart. In the event that any signature is delivered by facsimile transmission, or by e-mail delivery of a “.pdf” format data file, such signature shall create a valid and binding obligation of the party executing (or on whose behalf such signature is executed) with the same force and effect as if such facsimile signature page were an original thereof.

6.10

Severability. If any provision of this Agreement is held to be invalid or unenforceable in any respect, the validity and enforceability of the remaining terms and provisions of this Agreement shall not in any way be affected or impaired thereby and the parties will attempt to agree upon a valid and enforceable provision that is a reasonable substitute therefor, and upon so agreeing, shall incorporate such substitute provision in this Agreement.

6.11

Replacement of the Securities. If any certificate or instrument evidencing any of the Securities is mutilated, lost, stolen or destroyed, the Company shall issue or cause to be issued in exchange and substitution for and upon cancellation thereof, or in lieu of and substitution therefor, a new certificate or instrument, but only upon receipt of evidence reasonably satisfactory to the Company of such loss, theft or destruction and the execution by the holder thereof of a customary lost certificate affidavit of that fact and an agreement to indemnify and hold harmless the Company for any losses in connection therewith. The applicants for a new certificate or instrument under such circumstances shall also pay any reasonable third-party costs associated with the issuance of such replacement Securities. If a replacement certificate or instrument evidencing any of the Securities is requested due to a mutilation thereof, the Company may require delivery of such mutilated certificate or instrument as a condition precedent to any issuance of a replacement.

6.12

Remedies. In addition to being entitled to exercise all rights provided herein or granted by law, including recovery of damages, Purchaser and the Company will be entitled to specific performance under the Transaction Documents. The parties agree that monetary damages may not be adequate compensation for any loss incurred by reason of any breach of obligations described in the foregoing sentence and hereby agree to waive in any action for specific performance of any such obligation (other than in connection with any action for a temporary restraining order) the defense that a remedy at law would be adequate.

6.13

Governing Law. All questions concerning the construction, validity, enforcement and interpretation of this Agreement shall be governed by and construed and enforced in accordance with the internal laws of the State of Michigan, without regard to the principles of conflicts of law thereof. Each party agrees that all Proceedings concerning the interpretations, enforcement and defense of the transactions contemplated by this Agreement and any other Transaction Documents (whether brought against a party hereto or its respective Affiliates, employees or agents) shall be commenced exclusively in the Michigan Courts. Each party hereto hereby irrevocably submits to the exclusive jurisdiction of the Michigan Courts for the

adjudication of any dispute hereunder or in connection herewith or with any transaction contemplated hereby or discussed herein (including with respect to the enforcement of any of the Transaction Documents), and hereby irrevocably waives, and agrees not to assert in any Proceeding, any claim that it is not personally subject to the jurisdiction of any such Michigan Court, or that such Proceeding has been commenced in an improper or inconvenient forum. Each party hereto hereby irrevocably waives personal service of process and consents to process being served in any such Proceeding by mailing a copy thereof via registered or certified mail or overnight delivery (with evidence of delivery) to such party at the address in effect for notices to it under this Agreement and agrees that such service shall constitute good and sufficient service of process and notice thereof. Nothing contained herein shall be deemed to limit in any way any right to serve process in any manner permitted by law. EACH PARTY HERETO HEREBY IRREVOCABLY WAIVES, TO THE FULLEST EXTENT PERMITTED BY APPLICABLE LAW, ANY AND ALL RIGHT TO TRIAL BY JURY IN ANY LEGAL PROCEEDING ARISING OUT OF OR RELATING TO THIS AGREEMENT OR THE TRANSACTIONS CONTEMPLATED HEREBY.

Signatures on the Following Page

In Witness Whereof, the parties hereto have caused this Securities Purchase Agreement to be duly executed by their respective authorized signatories as of the date first indicated above.


Conifer Holdings Inc. By: /s/ Nicholas J. Petcoff Name: Nicholas J. Petcoff Title: Co-Chief Executive Officer

	Clarkston 91 West LLC By: /s/ Salvatore F. Gianino Name: Salvatore F. Gianino Title: Manager

Signature Page to

Securities Purchase Agreement

Exhibit A

Conifer Holdings Inc.

Certificate of Designation of

Series A Preferred Stock

Exhibit A

Exhibit B

CONIFER HOLDINGS INC.
CEO CERTIFICATE

December 20, 2023

Reference is made to that certain Securities Purchase Agreement, dated as of December 20, 2023 (the “Purchase Agreement”), by and amongst Conifer Holdings Inc., a Delaware corporation (the “Company”), and each purchaser identified on the signature pages thereto (the “Purchasers”). This CEO’s Certificate (this “Certificate”) is being delivered pursuant to Section 2.2(a)(ii) of the Purchase Agreement. Capitalized terms used but not defined herein shall have the respective meanings set forth in the Purchase Agreement.

I, Nicholas J. Petcoff, Co-Chief Executive Officer of the Company, do hereby certify, solely in my capacity as Co-Chief Executive Officer of the Company, that:

1. Each individual whose name, titles and signature appear below is a duly elected or appointed, qualified and acting representative of the Company holding the title set forth opposite his name below, and that the signature set forth opposite each individual’s name is the genuine signature of that individual; each such individual is authorized to sign on behalf of the Company as of the date of the execution of this Certificate and was so authorized on the date of execution of the Transaction Documents and related documents.


Name	Title	Signature
Harold J. Meloche	Chief Financial Officer	/s/ Harold J. Meloche
Brian J. Roney	President	/s/ Brian J. Roney

2. Attached hereto as Exhibit A is a true, correct, complete and current copy of the resolutions of the Board of Directors of the Company (the “Board”) or the Transaction Committee of the Board (the “Transaction Committee”), as applicable, approving the transactions contemplated by the Purchase Agreement and the other Transaction Documents and the issuance of the Securities, which resolutions were duly adopted by the Board or the Transaction Committee, as applicable, and none of such resolutions has been amended, modified or repealed in any respect, and all of such resolutions are in full force and effect on the date hereof.

3. Attached hereto as Exhibit B is a true, correct, complete and current copy of the Amended and Restated Certificate of Incorporation of the Company, as amended to date, including the Certificates of Designation, and the same has not been subsequently amended.

4. Attached hereto as Exhibit C is a true, correct, complete and current copy of the Bylaws of the Company and the same have not been subsequently amended.

Exhibit B

In Witness Whereof, the undersigned has executed and delivered this certificate for and on behalf of Conifer Holdings Inc. as of the date first set forth above.

Conifer Holdings Inc.

By: /s/ Nicholas J. Petcoff

Name: Nicholas J. Petcoff

Title: Co-Chief Executive Officer

Exhibit B

Exhibit C

ACCREDITED INVESTOR QUESTIONNAIRE

Exhibit C

Schedule 3.1(a)

Subsidiaries of Conifer Holdings Inc.


Subsidiary	State of Formation
Conifer Insurance Company	Michigan
Red Cedar Insurance Company	District of Columbia
Conifer Insurance Services	Michigan
White Pine Insurance Company	Michigan
Sycamore Specialty Underwriters, LLC (50% ownership)	Michigan

Schedule 3.1(a)