Exhibit 10.1


 


January 19, 2021


 


Oyster Enterprises Acquisition Corp.


300 Main Street


Stamford, Connecticut 06901


(212) 888-5500


 


Re: Initial Public Offering


 


Ladies and Gentlemen:


 


This letter (this “Letter Agreement”)
is being delivered to you in accordance with the Underwriting Agreement (the “Underwriting Agreement”) to be
entered into by and between Oyster Enterprises Acquisition Corp., a Delaware corporation (the “Company”), and
Imperial Capital, LLC (“Imperial Capital”), as representative of the several underwriters (the “Underwriters”),
relating to an underwritten initial public offering (the “Public Offering”) of up to 23,000,000 of the Company’s
units (including up to 3,000,000 units that may be purchased to cover over-allotments, if any) (the “Units”),
each comprised of one share of the Company’s Class A common stock, par value $0.0001 per share (the “Common
Stock”) and one-half of one redeemable warrant (each, a “Public Warrant”). Each whole Public Warrant
entitles the holder thereof to purchase one share of Common Stock at a price of $11.50 per share, subject to adjustment as described
in the Prospectus (as defined below). The Units will be sold in the Public Offering pursuant to a registration statement on Form S-1
and prospectus (the “Prospectus”) filed by the Company with the U.S. Securities and Exchange Commission
(the “Commission”) and the Company has applied to have the Units listed on The Nasdaq Capital Market. Certain
capitalized terms used herein are defined in paragraph 11 hereof.


 


In order to induce the Company and the Underwriters
to enter into the Underwriting Agreement and to proceed with the Public Offering and for other good and valuable consideration,
the receipt and sufficiency of which are hereby acknowledged, each of Oyster Enterprises LLC (the “Sponsor”)
and the undersigned individuals, each of whom is a member of the Company’s board of directors or a member of the Company’s
management team (each, an “Insider” and collectively, the “Insiders”), hereby severally (and
not jointly and severally) agrees with the Company as follows:


 


1.            The
Sponsor and each Insider agrees that if the Company seeks stockholder approval of a proposed Business Combination, then in connection
with such proposed Business Combination, it, he or she shall (i) vote any shares of Capital Stock owned by it, him or her
in favor of such proposed Business Combination and (ii) not redeem any shares of Capital Stock owned by it, him or her in
connection with such stockholder approval. If the Company engages in a tender offer in connection with any proposed Business Combination,
the Sponsor and each Insider agrees that it, he or she will not sell or tender any shares of Capital Stock owned by it, him or
her in connection with such tender offer.


 






     


     


    

 


2.            The
Sponsor and each Insider hereby agrees that in the event that the Company fails to consummate a Business Combination within 24 months
from the closing of the Public Offering, or such later period approved by the Company’s stockholders in accordance with the
Company’s amended and restated certificate of incorporation, as may be amended (the “Charter”)(any such
later period that is approved, the “Extension Period”), the Sponsor and each Insider shall take all reasonable
steps to cause the Company to (i) cease all operations except for the purpose of winding up, (ii) as promptly as reasonably
possible but not more than 10 Business Days thereafter, subject to lawfully available funds therefor, redeem 100% of the Common
Stock sold as part of the Units in the Public Offering (the “Offering Shares”), at a per-share price, payable
in cash, equal to the aggregate amount then on deposit in the Trust Account, including interest earned on the funds held in the
Trust Account (net of amounts withdrawn to pay the Company’s taxes (“Permitted Withdrawals”) and up to
$100,000 of interest to pay dissolution expenses), divided by the number of then outstanding Offering Shares, which redemption
will completely extinguish all Public Stockholders’ rights as stockholders of the Company (including the right to receive
further liquidating distributions, if any), subject to applicable law, and (iii) as promptly as reasonably possible following
such redemption, subject to the approval of the Company’s remaining stockholders and the Company’s board of directors,
dissolve and liquidate, subject in each case to the Company’s obligations under Delaware law to provide for claims of creditors
and other requirements of applicable law. The Sponsor and each Insider agrees not to propose any amendment to the Charter (i) to
modify the substance or timing of the Company’s obligation to provide holders of Common Stock the right to have their shares
redeemed or to redeem 100% of the Offering Shares if the Company does not complete a Business Combination within 24 months
from the closing of the Public Offering or (ii) with respect to any other material provision relating to stockholders’
rights or pre-initial Business Combination activity, unless, in each case, the Company provides its Public Stockholders with the
opportunity to redeem their Offering Shares upon approval of any such amendment at a per-share price, payable in cash, equal to
the aggregate amount then on deposit in the Trust Account, including interest earned on the funds held in the Trust Account (net
of Permitted Withdrawals), divided by the number of then outstanding Offering Shares.


 


The Sponsor and each Insider acknowledges
that, with respect to the Founder Shares held by it, him or her, it, he or she has no right, title, interest or claim of any kind
in or to any monies held in the Trust Account as a result of any liquidation of the Company. The Sponsor and each Insider hereby
further waives, with respect to any shares of Capital Stock held by it, him or her, if any, any redemption rights it, he or she
may have in connection with the consummation of a Business Combination, including, without limitation, any such rights available
in the context of a stockholder vote to approve such Business Combination or in the context of a tender offer made by the Company
to purchase shares of Common Stock (although the Sponsor, the Insiders and their respective affiliates shall be entitled to redemption
and liquidation rights with respect to any Offering Shares it or they hold if the Company fails to consummate a Business Combination
within the 24 months from the closing of the Public Offering) or in connection with a stockholder vote to approve an amendment
to the Charter to modify the substance or timing of the Company’s obligation to provide holders of Common Stock the right
to have their shares redeemed or to redeem 100% of the Offering Shares if the Company does not complete a Business Combination
within the 24 months from the closing of the Public Offering or with respect to any other material provision relating to stockholders’
rights or pre-initial Business Combination activity.


 






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3.            During
the period commencing on the effective date of the Underwriting Agreement and ending 180 days after such date, the Sponsor
and each Insider shall not, without the prior written consent of Imperial Capital, (i) sell, offer to sell, contract or agree
to sell, hypothecate, pledge, grant any option to purchase or otherwise dispose of or agree to dispose of, directly or indirectly,
any Units, shares of Capital Stock, Warrants or any securities convertible into, or exercisable, or exchangeable for, shares of
Capital Stock owned by it, him or her, (ii) 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”), and the rules and regulations of the Commission promulgated thereunder, with respect to any Units, shares
of Capital Stock, Warrants or any securities convertible into, or exercisable, or exchangeable for, shares of Capital Stock owned
by it, him or her, (iii) enter into any swap or other arrangement that transfers to another, in whole or in part, any of the
economic consequences of ownership of any Units, shares of Capital Stock, Warrants or any securities convertible into, or exercisable,
or exchangeable for, shares of Capital Stock owned by it, him or her, whether any such transaction is to be settled by delivery
of such securities, in cash or otherwise, or (iv) publicly announce any intention to effect any transaction specified in clause (i),
(ii) or (iii); provided, however, that the foregoing shall not apply to the forfeiture of any Founder Shares
pursuant to their terms or any transfer of Founder Shares to current or future independent directors of the Company (as long as
such current or future independent director is or becomes subject to the terms of this Letter Agreement with respect to such Founder
Shares at the time of such transfer).


 


4.            In
the event of the liquidation of the Trust Account upon the failure of the Company to consummate its initial Business Combination
within the time period set forth in the Charter, the Sponsor (which, for purposes of clarification, shall not extend to any stockholders,
members, managers of the Sponsor or any Insider), solely in its corporate capacity, agrees to indemnify and hold harmless the Company
against any and all loss, liability, claim, damage and expense whatsoever (including, but not limited to, any and all legal or
other expenses reasonably incurred in investigating, preparing or defending against any litigation, whether pending or threatened,
or any claim whatsoever) to which the Company may become subject as a result of any claim by (i) any third party (other than
the Company’s independent registered public accounting firm) for services rendered or products sold to the Company or (ii) any
prospective target business with which the Company has discussed entering into a Business Combination agreement (a “Target”);
provided, however, that such indemnification of the Company by the Sponsor (x) shall apply only to the extent
necessary to ensure that such claims by a third party or a Target do not reduce the amount of funds in the Trust Account to below
the lesser of (i) $10.00 per Offering Share and (ii) the actual amount per Offering Share held in the Trust Account as
of the date of the liquidation of the Trust Account, if less than $10.00 per Offering Share is then held in the Trust Account due
to reductions in the value of the trust assets, in each case, less Permitted Withdrawals, (y) shall not apply to any claims
by a third party or a Target that executed a waiver of any and all rights to the monies held in the Trust Account (whether or not
such waiver is enforceable) and (z) shall not apply to any claims under the Company’s indemnity of the Underwriters
against certain liabilities, including liabilities under the Securities Act of 1933, as amended. The Sponsor shall have the right
to defend against any such claim with counsel of its choice reasonably satisfactory to the Company if, within 15 days following
written receipt of notice of the claim to the Sponsor, the Sponsor notifies the Company in writing that it shall undertake such
defense. For the avoidance of doubt, none of the Company’s officers or directors will indemnify the Company for claims by
third parties, including, without limitation, claims by vendors and prospective target businesses.


 









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5.            To
the extent that the Underwriters do not exercise their over-allotment option to purchase up to an additional 3,000,000 Units within
45 days from the date of the Prospectus (and as further described in the Prospectus), the Sponsor agrees to forfeit, at no
cost, a number of Founder Shares equal to the product of 750,000 multiplied by a fraction, (i) the numerator of which is 3,000,000
minus the number of Units purchased by the Underwriters upon the exercise of their over-allotment option, if any, and (ii) the
denominator of which is 3,000,000.


 


6.            The
Sponsor and each Insider hereby agrees and acknowledges that: (i) the Underwriters and the Company would be irreparably injured
in the event of a breach by the Sponsor or such Insider of its, his or her obligations under paragraphs 1, 2, 3, 4, 5, 7(a), 7(b),
and 9, as applicable, of this Letter Agreement (ii) monetary damages may not be an adequate remedy for such breach and (iii) the
non-breaching party shall be entitled to injunctive relief, in addition to any other remedy that such party may have in law or
in equity, in the event of such breach.


 


7.            (a)     The Sponsor and each Insider agrees that it,
he or she shall not Transfer any Founder Shares (or shares of Common Stock issuable upon conversion thereof) until the
earlier of (A) one year after the completion of the Company’s initial Business Combination and (B) subsequent
to the Company’s initial Business Combination, (x) if the closing price of the Common Stock equals or exceeds
$12.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20
trading days within any 30-trading day period commencing at least 150 days after the completion of the Company’s
initial Business Combination or (y) the date on which the Company completes a liquidation, merger, capital stock
exchange, reorganization or other similar transaction that results in all of the Company’s stockholders having the
right to exchange their shares of common stock for cash, securities or other property (the “Founder Shares Lock-up
Period”).


 


(b)     The
Sponsor and each Insider agrees that it, he or she shall not Transfer any Private Placement Warrants (or shares of Common Stock
issued or issuable upon the exercise of the Private Placement Warrants) until 30 days after the completion of the Company’s
initial Business Combination (the “Private Placement Warrants Lock-up Period,” together with the Founder Shares
Lock-up Period, the “Lock-up Periods”).


 


(c)     Notwithstanding
the provisions set forth in paragraphs 3 and 7(a) and (b), Transfers of the Founder Shares, Private Placement Warrants and
shares of Common Stock issued or issuable upon the exercise or conversion of the Private Placement Warrants or the Founder Shares
and that are held by the Sponsor, any Insider or any of their permitted transferees (that have complied with this paragraph 7(c)),
are permitted (i) to the Company’s officers or directors, any affiliates or family members of any of the Company’s
officers or directors, any members of the Sponsor, or any affiliates of the Sponsor, including to funds affiliated with Alden Global
Capital LLC, and to limited partners of funds affiliated with Alden Global Capital LLC, provided that any such transfers
to limited partners are made on a pro rata basis pursuant to the organizational documents of such funds and internal allocation
policy; (ii) in the case of an individual, by gift to a member of the individual’s immediate family, to a trust, the
beneficiary of which is a member of the individual’s immediate family or an affiliate of such individual, or to a charitable
organization; (iii) in the case of an individual, by virtue of the laws of descent and distribution upon death of the individual;
(iv) in the case of an individual, pursuant to a qualified domestic relations order; (v) by private sales or transfers
made in connection with the consummation of the Company’s initial Business Combination at prices no greater than the price
at which the Founder Shares, Private Placement Warrants or the shares of Common Stock, as the case may be, were originally purchased;
(vi) in the event of the Company’s liquidation prior to the completion of its initial Business Combination; (vii) by
virtue of the laws of the State of Delaware or the Sponsor’s limited liability company agreement upon dissolution of the
Sponsor; (viii) in the event of the Company’s completion of a liquidation, merger, capital stock exchange, reorganization
or other similar transaction which results in all of the Company’s stockholders having the right to exchange their shares
of Capital Stock for cash, securities or other property subsequent to the Company’s completion of its initial Business Combination;
or (ix) to a nominee or custodian of a person or entity to whom a disposition or transfer would be permissible under clauses (i) through
(viii) above; provided, however, that in the case of clauses (i) through (v) and (ix), these
permitted transferees must enter into a written agreement with the Company agreeing to be bound by the transfer restrictions herein
and the other restrictions contained in this Agreement.


 






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8.            The
Sponsor and each Insider represents and warrants that it, he or she has never been suspended or expelled from membership in any
securities or commodities exchange or association or had a securities or commodities license or registration denied, suspended
or revoked. Each Insider’s biographical information furnished to the Company (including any such information included in
the Prospectus) is true and accurate in all respects and does not omit any material information with respect to such Insider’s
background. The Sponsor and each Insider’s questionnaire furnished to the Company and the Underwriters is true and accurate
in all respects. The Sponsor and each Insider represents and warrants that: it, he or she is not subject to or a respondent in
any legal action for, any injunction, cease-and-desist order or order or stipulation to desist or refrain from any act or practice
relating to the offering of securities in any jurisdiction; it, he or she has never been convicted of, or pleaded guilty to, any
crime (i) involving fraud, (ii) relating to any financial transaction or handling of funds of another person or (iii) pertaining
to any dealings in any securities and it, he or she is not currently a defendant in any such criminal proceeding.


 


9.            Except
as disclosed in the Prospectus, neither the Sponsor nor any Insider nor any affiliate of the Sponsor or any Insider shall receive
from the Company any finder’s fee, reimbursement, consulting fee, monies in respect of any repayment of a loan or other compensation
for services rendered to the Company prior to or in connection with the consummation of the Company’s initial Business Combination
(regardless of the type of transaction that it is), other than the following, none of which will be made from the proceeds held
in the Trust Account prior to the completion of the initial Business Combination: repayment of a loan and advances of up to $350,000
made to the Company by the Sponsor to cover expenses related to the organization of the Company and the Public Offering; payment
of a one-time cash bonus of $150,000 to each of Mr. Maz Akram and Mr. Martin Wade, two of the Company’s independent
directors, upon the successful completion of the Company’s initial Business Combination; reimbursement for any out-of-pocket
expenses related to identifying, investigating and consummating the Company’s initial Business Combination; and repayment
of loans, if any, and on such terms as to be determined by the Company from time to time, made by the Sponsor, Alden Global Capital
LLC or certain of the Company’s officers and directors to finance transaction costs in connection with an intended initial
Business Combination, provided, that, if the Company does not consummate an initial Business Combination, a portion of the
working capital held outside the Trust Account may be used by the Company to repay such loaned amounts so long as no proceeds from
the Trust Account are used for such repayment. Up to $1,500,000 of such loans may be convertible into warrants of the post Business
Combination entity at a price of $1.00 per warrant at the option of the lender. Such warrants would be identical to the Private
Placement Warrants, including as to exercise price, exercisability and exercise period.


 






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10.          The
Sponsor and each Insider has full right and power, without violating any agreement to which it is bound (including, without limitation,
any non-competition or non-solicitation agreement with any employer or former employer), to enter into this Letter Agreement and,
as applicable, to serve as an officer and/or a director of the Company and hereby consents to being named in the Prospectus as
an officer and/or a director of the Company.


 


11.          As
used herein, (i) “Business Combination” shall mean a merger, capital stock exchange, asset acquisition,
stock purchase, reorganization or similar business combination, involving the Company and one or more businesses; (ii) “Business
Day” shall mean each day that is not a Saturday, Sunday or other day on which banking institutions in The City of New York,
New York, are authorized or required by law to close; (iii) “Capital Stock” shall mean, collectively,
the Common Stock and the Founder Shares; (iv) “Founder Shares” shall mean the 5,750,000 shares of
the Company’s Class B common stock, par value $0.0001 per share (up to 750,000 of which are subject to forfeiture depending
on the extent to which the Underwriters’ over-allotment option is exercised) outstanding immediately prior to the consummation
of the Public Offering; (v) “Initial Stockholders” shall mean the Sponsor and any other person that is
a holder of Founder Shares immediately prior to the Public Offering; (vi) “Private Placement Warrants”
shall mean the warrants to purchase up to 5,950,000 shares of Common Stock of the Company (or 6,550,000 shares of Common Stock
if the Underwriters’ over-allotment option is exercised in full) that the Sponsor and the Underwriters have agreed to purchase
for an aggregate purchase price of $5,950,000 in the aggregate (or $6,550,000 if the Underwriters’ over-allotment option
is exercised in full), or $1.00 per warrant, in a private placement that shall occur simultaneously with the consummation of the
Public Offering; (vii) “Public Stockholders” shall mean the holders of the Offering Shares; (viii) “Trust
Account” shall mean the trust fund into which a portion of the net proceeds of the Public Offering and the sale of the
Private Placement Warrants shall be deposited; (ix) “Transfer” shall mean the (a) sale, assignment,
offer to sell, contract or agreement to sell, hypothecate, pledge, grant of any option to purchase or otherwise dispose of or agreement
to dispose of, directly or indirectly, or establishment or increase of a put equivalent position or liquidation with respect to
or decrease of a call equivalent position within the meaning of Section 16 of the Exchange Act and the rules and regulations
of the Commission promulgated thereunder with respect to, any security, (b) entry into any swap or other arrangement that
transfers to another, in whole or in part, any of the economic consequences of ownership of any security, whether any such transaction
is to be settled by delivery of such securities, in cash or otherwise, or (c) public announcement of any intention to effect
any transaction specified in clause (a) or (b); and (x) “Warrants” shall mean the Public Warrants
and the Private Placement Warrants.


 






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12.          This
Letter Agreement constitutes the entire agreement and understanding of the parties hereto in respect of the subject matter hereof
and supersedes all prior understandings, agreements, or representations by or among the parties hereto, written or oral, to the
extent they relate in any way to the subject matter hereof or the transactions contemplated hereby. This Letter Agreement may not
be changed, amended, modified or waived (other than to correct a typographical error) as to any particular provision, except by
a written instrument executed by all parties hereto.


 


13.          Except
as otherwise provided herein, no party hereto may assign either this Letter Agreement or any of its rights, interests, or obligations
hereunder without the prior written consent of the other parties. Any purported assignment in violation of this paragraph shall
be void and ineffectual and shall not operate to transfer or assign any interest or title to the purported assignee. This Letter
Agreement shall be binding on the Sponsor and each Insider and their respective successors, heirs and assigns and permitted transferees.


 


14.          Nothing
in this Letter Agreement shall be construed to confer upon, or give to, any person or entity other than the parties hereto any
right, remedy or claim under or by reason of this Letter Agreement or of any covenant, condition, stipulation, promise or agreement
hereof. All covenants, conditions, stipulations, promises and agreements contained in this Letter Agreement shall be for the sole
and exclusive benefit of the parties hereto and their successors, heirs, personal representatives and assigns and permitted transferees.


 


15.          This
Letter Agreement may be executed in any number of original or facsimile counterparts and each of such counterparts shall for all
purposes be deemed to be an original, and all such counterparts shall together constitute but one and the same instrument. The
words “executed,” “signed,” “signature,” and words of like import in this Letter Agreement
or in any other certificate, agreement or document related to this Letter Agreement shall include images of manually executed signatures
transmitted by facsimile or other electronic format (including, without limitation, “pdf,” “tif” or “jpg”)
and other electronic signatures (including, without limitation, DocuSign and AdobeSign). The use of electronic signatures and electronic
records (including, without limitation, any contract or other record created, generated, sent, communicated, received, or stored
by electronic means) shall be of the same legal effect, validity and enforceability as a manually executed signature or use of
a paper-based record-keeping system to the fullest extent permitted by applicable law, including the Federal Electronic Signatures
in Global and National Commerce Act, the New York State Electronic Signatures and Records Act and any other applicable law, including,
without limitation, any state law based on the Uniform Electronic Transactions Act or the Uniform Commercial Code.


 


16.          This
Letter Agreement shall be deemed severable, and the invalidity or unenforceability of any term or provision hereof shall not affect
the validity or enforceability of this Letter Agreement or of any other term or provision hereof. Furthermore, in lieu of any such
invalid or unenforceable term or provision, the parties hereto intend that there shall be added as a part of this Letter Agreement
a provision as similar in terms to such invalid or unenforceable provision as may be possible and be valid and enforceable.


 






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17.          This
Letter Agreement shall be governed by and construed and enforced in accordance with the laws of the State of New York, without
giving effect to conflicts of law principles that would result in the application of the substantive laws of another jurisdiction.
The parties hereto (i) all agree that any action, proceeding, claim or dispute arising out of, or relating in any way to,
this Letter Agreement shall be brought and enforced in the courts of New York City, in the State of New York, and irrevocably submit
to such jurisdiction and venue, which jurisdiction and venue shall be exclusive and (ii) waive any objection to such exclusive
jurisdiction and venue or that such courts represent an inconvenient forum.


 


18.          Any
notice, consent or request to be given in connection with any of the terms or provisions of this Letter Agreement shall be in writing
and shall be sent by express mail or similar private courier service, by certified mail (return receipt requested), by hand delivery
or facsimile transmission.


 


19.          This
Letter Agreement shall terminate on the earlier of (i) the expiration of the Lock-up Periods or (ii) the liquidation
of the Company; provided, however, that this Letter Agreement shall earlier terminate in the event that the Public
Offering is not consummated by February 28, 2021; provided further that paragraph 4 of this Letter Agreement shall
survive such liquidation.


 


[Signature Page Follows]


 






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	 	Sincerely,
	 	 	 
	 	OYSTER
                                         ENTERPRISES LLC
	 	By:	Oyster AG Manager LLC, its Manager
	 	 	 
	 	By:	/s/ Heath B. Freeman
	 	 	Heath B. Freeman, Member
	 	 	 
	 	 	/s/ Randall D. Smith
	 	 	Randall D. Smith
	 	 	 
	 	 	/s/ Heath B. Freeman
	 	 	Heath B. Freeman
	 	 	 
	 	 	/s/ Joshua P. Kleban
	 	 	Joshua P. Kleban
	 	 	 
	 	 	/s/ Michael J. Monticciolo
	 	 	Michael J. Monticciolo
	 	 	 
	 	 	/s/ Maz Akram
	 	 	Maz Akram
	 	 	 
	 	 	/s/ Martin R. Wade, III
	 	 	Martin R. Wade, III




 


	Acknowledged and Agreed:
	OYSTER ENTERPRISES ACQUISITION CORP.




 


	By:	/s/ Michael J. Monticciolo	 
		Name: Michael J. Monticciolo	 
		Title: Chief Legal Officer, Chief Operating Officer and Secretary	 




 


[Signature
Page to Letter Agreement]