Lock-Up Agreement


 


December 10, 2021


 


Star Equity Holdings, Inc.


53 Forest Ave, Suite 101


Old Greenwich, CT 06870


 


		Re:	Securities Purchase Agreement, dated as of December 10, 2021 (the “Purchase Agreement”),
between Star Equity Holdings, Inc. (the “Company”) and the purchaser signatory thereto (the “Purchaser”)



 


Ladies and Gentlemen:


 


Defined terms not otherwise defined in this letter
agreement (the “Letter Agreement”) shall have the meanings set forth in the Purchase Agreement. Pursuant to Section
2.2(a) of the Purchase Agreement and in satisfaction of a condition of the Company’s obligations under the Purchase Agreement, the
undersigned irrevocably agrees with the Company that, from the date hereof until six (6) months following the date hereof (such period,
the “Restriction Period”), the undersigned will not offer, sell, contract to sell, hypothecate, specifically pledge
or otherwise dispose of (or enter into any transaction which is designed to result in the disposition (whether by actual disposition or
effective economic disposition due to cash settlement or otherwise) by the undersigned or any Affiliate of the undersigned or any person
in privity with the undersigned or any Affiliate of the undersigned), directly or indirectly, or establish or increase a put equivalent
position or liquidate or decrease a call equivalent position within the meaning of Section 16 of the Securities Exchange Act of 1934,
as amended (the “Exchange Act”), with respect to, any shares of common stock of the Company, $0.0001 par value per
share (the “Common Stock”), or securities convertible, exchangeable or exercisable into, Common Stock of the Company
beneficially owned, held or hereafter acquired by the undersigned (the “Securities”). Beneficial ownership shall be
calculated in accordance with Section 13(d) of the Exchange Act. [In order to enforce this covenant, the Company shall impose irrevocable
stop-transfer instructions preventing the transfer agent of the Company from effecting any actions in violation of this Letter Agreement.]
1


 


Notwithstanding the foregoing, and subject to
the conditions below, the undersigned may transfer the Securities provided that (1) the Company receives a signed lock-up letter
agreement (in the form of this Letter Agreement) for the balance of the Restriction Period from each donee, trustee, distributee, or transferee,
as the case may be, prior to such transfer, (2) any such transfer shall not involve a disposition for value, (3) such transfer
is not required to be reported with the Securities and Exchange Commission in accordance with the Exchange Act and no report of such transfer
shall be made voluntarily, and (4) neither the undersigned nor any donee, trustee, distributee or transferee, as the case may be,
otherwise voluntarily effects any public filing or report regarding such transfers, with respect to transfer:


 


__________________________


1
Acceptable if shares remain unregistered. If shares registered, TA ability to execute to be confirmed.






     


     


    

 


	 	i)	as a bona fide gift or gifts;


 


	 	ii)	to any immediate family member or to any trust for the direct or indirect benefit of the undersigned or the immediate family of the undersigned (for purposes of this Letter Agreement, “immediate family” shall mean any relationship by blood, marriage or adoption, not more remote than first cousin);


 


	 	iii)	to any corporation, partnership, limited liability company, or other business entity all of the equity holders of which consist of the undersigned and/or the immediate family of the undersigned;


 


	 	iv)	if the undersigned is a corporation, partnership, limited liability company, trust or other business entity (a) to another corporation, partnership, limited liability company, trust or other business entity that is an Affiliate of the undersigned or (b) in the form of a distribution to limited partners, limited liability company members or stockholders of the undersigned;


 


	 	v)	if the undersigned is a trust, to the beneficiary of such trust; or


 


	 	vi)	by will, other testamentary document or intestate succession to the legal representative, heir, beneficiary or a member of the immediate family of the undersigned.


 


In addition, notwithstanding the foregoing, this
Letter Agreement shall not restrict the delivery of Common Stock to the undersigned upon (i) exercise of any options granted under any
equity incentive plan of the Company; provided that any Common Stock or Securities acquired in connection with any such exercise will
be subject to the restrictions set forth in this Letter Agreement, or (ii) the exercise of warrants; provided that such Common Stock delivered
to the undersigned in connection with such exercise are subject to the restrictions set forth in this Letter Agreement. Furthermore, this
Letter Agreement shall not restrict the ability of the undersigned to effect sales of Common Stock or Securities pursuant to that certain
Rule 10b5-1 Sale Trading Plan dated June 10, 2021 between the undersigned and Clear Street LLC.


 


Furthermore, the undersigned may enter into any
new plan established in compliance with Rule 10b5-1 of the Exchange Act; provided that no sales of Common Stock are made pursuant to such
plan during the Restriction Period.


 


The undersigned acknowledges that the execution,
delivery and performance of this Letter Agreement is a material inducement to the Purchaser to complete the transactions contemplated
by the Purchase Agreement and the Company shall be entitled to specific performance of the undersigned’s obligations hereunder.
The undersigned hereby represents that the undersigned has the power and authority to execute, deliver and perform this Letter Agreement,
that the undersigned has received adequate consideration therefor and that the undersigned will indirectly benefit from the closing of
the transactions contemplated by the Purchase Agreement.


 






    2 


     


    

 


This Letter Agreement may not be amended or otherwise
modified in any respect without the written consent of each of the Company and the undersigned. This Letter Agreement shall be construed
and enforced in accordance with the internal laws of the State of New York, without giving effect to any laws, rules or provisions thereof
that would cause the application of the laws, rules or provisions of any jurisdiction other than those of the State of New York. The undersigned
hereby irrevocably submits to the exclusive jurisdiction of the United States District Court sitting in the Southern District of New York
and the courts of the State of New York located in Manhattan, for the purposes of any suit, action or proceeding arising out of or relating
to this Letter Agreement, and hereby waives, and agrees not to assert in any such suit, action or proceeding, any claim that (i) it is
not personally subject to the jurisdiction of such court, (ii) the suit, action or proceeding is brought in an inconvenient forum, or
(iii) the venue of the suit, action or proceeding is improper. The undersigned hereby irrevocably waives personal service of process and
consents to process being served in any such suit, action or proceeding by receiving a copy thereof sent to the Company at the address
in effect for notices to it under the Purchase Agreement and agrees that such service shall constitute good and sufficient service of
process and notice thereof. The undersigned hereby waives any right to a trial by jury. Nothing contained herein shall be deemed to limit
in any way any right to serve process in any manner permitted by law. The undersigned agrees and understands that this Letter Agreement
does not intend to create any relationship between the undersigned and the Purchaser and that the Purchaser is not entitled to cast any
votes on the matters herein contemplated and that no issuance or sale of the Securities is created or intended by virtue of this Letter
Agreement.


 


This Letter Agreement shall be binding on successors
and assigns of the undersigned with respect to the Securities and any such successor or assign shall enter into a similar agreement for
the benefit of the Purchaser.


 


*** SIGNATURE PAGE FOLLOWS***


 






    3 


     


    

 


This Letter Agreement may be executed in two or
more counterparts, all of which when taken together may be considered one and the same agreement.


 


 


	/s/ Jeffrey E. Eberwein	 
	Jeffrey E. Eberwein	 



 


Address for Notice:


 


E-mail: jeff.eberwein@starequity.com


 


 


 


By signing below, the Company
agrees to enforce the restrictions on transfer set forth in this Letter Agreement.


 


STAR EQUITY HOLDINGS, INC. 


 


 


	By:	/s/ David Noble	 
	Name:	David Noble	 
	Title:	Chief Financial Officer	 



 


 


Address for Notice:


53 Forest Ave, Suite 101


Old Greenwich, CT 06870


 


E-mail: legal@starequity.com


 


[SIGNATURE PAGE TO STAR EQUITY HOLDINGS, INC.
LOCK-UP LETTER AGREEMENT]


 


4