Document:

Exhibit 10.5

 

Oyster Enterprises Acquisition Corp.

c/o Alden Global Capital LLC

885 Third Avenue

New York, New York 10022

 

November
16, 2020

 

Oyster Enterprises LLC

c/o Alden Global Capital LLC

885 Third Avenue

New York, New York 10022

 

RE: Securities Subscription
Agreement

 

Ladies and Gentlemen:

 

We are pleased to accept
the offer Oyster Enterprises LLC (the “Subscriber” or “you”) has made to purchase 5,750,000
shares of Class B common stock (the “Shares”), $0.0001 par value per share (the “Class B
Common Stock” and, together with all other classes of common stock of the Company (as defined below), the “Common
Stock”), up to 750,000 Shares of which are subject to complete or partial forfeiture by you if the underwriters of the
initial public offering (“IPO”) of Oyster Enterprises Acquisition Corp., a Delaware corporation (the “Company”),
do not exercise their over-allotment option (the “Over-allotment Option”) in the IPO in full. The terms on which
the Company is willing to sell the Shares to the Subscriber, and the Company and the Subscriber’s agreements regarding the
Shares, are as follows:

 

1.           
Purchase of Shares. For the sum of $25,000 (the “Purchase Price”), which the Company acknowledges
receiving in cash, the Company hereby sells and issues the Shares to the Subscriber, and the Subscriber hereby purchases the Shares
from the Company, subject to the forfeiture provisions of Section 3 below, on the terms and subject to the conditions set
forth in this Securities Subscription Agreement (this “Agreement”).

 

2.           
Representations, Warranties and Agreements.

 

2.1.         
Subscriber’s Representations, Warranties and Agreements. To induce the Company to issue the Shares to the Subscriber,
the Subscriber hereby represents and warrants to the Company and agrees with the Company as follows:

 

2.1.1.     
No Government Recommendation or Approval. The Subscriber understands that no federal or state agency has passed upon
or made any recommendation or endorsement of the offering of the Shares.

 

2.1.2.      No
Conflicts. The execution, delivery and performance of this Agreement and the consummation by the Subscriber of the
transactions contemplated hereby do not violate, conflict with or constitute a default under (i) the formation and
governing documents of the Subscriber, (ii) any agreement, indenture or instrument to which the Subscriber is a party,
(iii) any law, statute, rule or regulation to which the Subscriber is subject, or (iv) any agreement, order,
judgment or decree to which the Subscriber is subject.

 

     

     

    

 

2.1.3.     
Organization and Authority. The Subscriber is a Delaware limited liability company, validly existing and in good
standing under the laws of Delaware and possesses all requisite power and authority necessary to carry out the transactions contemplated
by this Agreement. Upon execution and delivery by you, this Agreement will be a legal, valid and binding agreement of the Subscriber,
enforceable against the Subscriber in accordance with its terms, except as such enforceability may be limited by applicable bankruptcy,
insolvency, fraudulent conveyance or similar laws affecting the enforcement of creditors’ rights generally and subject to
general principles of equity (regardless of whether enforcement is sought in a proceeding at law or in equity).

 

2.1.4.     
Experience, Financial Capability and Suitability. The Subscriber is: (i) sophisticated in financial matters
and is able to evaluate the risks and benefits of the investment in the Shares and (ii) able to bear the economic risk of
its investment in the Shares for an indefinite period of time because the Shares have not been registered under the Securities
Act (as defined below) and therefore cannot be resold unless subsequently registered under the Securities Act or an exemption from
such registration is available. The Subscriber is capable of evaluating the merits and risks of its investment in the Company and
has the capacity to protect its own interests.

 

2.1.5.     
Access to Information; Independent Investigation. Prior to the execution of this Agreement, the Subscriber has had
the opportunity to ask questions of and receive answers from representatives of the Company concerning an investment in the Company,
as well as the finances, operations, business and prospects of the Company, and the opportunity to obtain additional information
to verify the accuracy of all information so obtained. In determining whether to make this investment, the Subscriber has relied
solely on the Subscriber’s own knowledge and understanding of the Company and its business based upon the Subscriber’s
own due diligence investigation and the information furnished pursuant to this paragraph. The Subscriber understands that no person
has been authorized to give any information or to make any representations which were not furnished pursuant to this Section 2
and the Subscriber has not relied on any other representations or information in making its investment decision, whether written
or oral, relating to the Company, its operations or its prospects.

 

2.1.6.     
Accredited Investor. The Subscriber represents that it is an “accredited investor” as such term is defined
in Rule 501(a) of Regulation D under the Securities Act of 1933, as amended (the “Securities Act”) and acknowledges
the sale contemplated hereby is being made in reliance on a private placement exemption under federal and state law.

 

2.1.7.     
Investment Purposes. The Subscriber is purchasing the Shares solely for investment purposes, for the Subscriber’s
own account and not for the account or benefit of any other person, and not with a view towards the distribution or dissemination
thereof that would result in a violation of the Securities Act. The Subscriber did not enter into this Agreement as a result of
any general solicitation or general advertising within the meaning of Rule 502 of Regulation D under the Securities Act.

 

    2

     

    

 

2.1.8.     
 Restrictions on Transfer; Shell Company. The Subscriber understands the Shares are being offered in a transaction
not involving a public offering within the meaning of the Securities Act. Subscriber understands the Shares will be “restricted
securities” as defined in Rule 144(a)(3) under the Securities Act and Subscriber understands that the certificates or
book entries representing the Shares will contain a legend in respect of such restrictions. If in the future the Subscriber decides
to offer, resell, pledge or otherwise transfer the Shares, the Shares may be offered, resold, pledged or otherwise transferred
only in accordance with the provisions of Section 5 hereof. The Subscriber agrees that if any transfer of its Shares or any interest
therein is proposed to be made, as a condition precedent to any such transfer, Subscriber may be required to deliver to the Company
an opinion of counsel satisfactory to the Company. Absent registration or an exemption, the Subscriber agrees not to offer, resell,
pledge or otherwise transfer the Shares. Subscriber further acknowledges that because the Company is a shell company, Rule 144
may not be available to the Subscriber for the resale of the Shares until one year following consummation of the initial business
combination of the Company, despite technical compliance with the certain requirements of Rule 144 and the release or waiver
of any contractual transfer restrictions.

 

2.1.9.     
No Governmental Consents. No governmental, administrative or other third party consents or approvals are required,
necessary or appropriate on the part of Subscriber in connection with the transactions contemplated by this Agreement.

 

2.2.          Company’s Representations, Warranties and Agreements. To induce the Subscriber to purchase the Shares, the
Company hereby represents and warrants to the Subscriber and agrees with the Subscriber as follows:

 

2.2.1.     
Organization and Corporate Power. The Company is a Delaware corporation and is qualified to do business in every
jurisdiction in which the failure to so qualify would reasonably be expected to have a material adverse effect on the financial
condition, operating results or assets of the Company. The Company possesses all requisite corporate power and authority necessary
to carry out the transactions contemplated by this Agreement.

 

2.2.2.     
No Conflicts. The execution, delivery and performance of this Agreement and the consummation by the Company of the
transactions contemplated hereby do not violate, conflict with or constitute a default under (i) the Certificate of Incorporation
or Bylaws of the Company, (ii) any agreement, indenture or instrument to which the Company is a party, (iii) any law,
statute, rule or regulation to which the Company is subject, or (iv) any agreement, order, judgment or decree to which the
Company is subject.

 

2.2.3.     
Title to Securities. Upon issuance in accordance with, and payment pursuant to, the terms hereof, the Shares will
be duly and validly issued, fully paid and nonassessable. Upon issuance in accordance with, and payment pursuant to, the terms
hereof the Subscriber will have or receive good title to the Shares, free and clear of all liens, claims and encumbrances of any
kind, other than (i) transfer restrictions hereunder and under other agreements to which the Shares may be subject which have
been notified to the Subscriber in writing, (ii) transfer restrictions under federal and state securities laws, and (iii) liens,
claims or encumbrances imposed due to the actions of the Subscriber.

 

    3

     

    

 

2.2.4.     
 No Adverse Actions. There are no actions, suits, investigations or proceedings pending, threatened against or affecting
the Company which: (i) seek to restrain, enjoin, prevent the consummation of or otherwise affect the transactions contemplated
by this Agreement or (ii) question the validity or legality of any transactions or seek to recover damages or to obtain other
relief in connection with any transactions.

 

3.           
Forfeiture of Shares.

 

3.1.         
Partial or No Exercise of the Over-allotment Option. In the event the Over-allotment Option is not exercised
in full, the Subscriber acknowledges and agrees that it shall forfeit any and all rights to such number of Shares (which, if the
number of shares of the Company’s Class A common stock included in the Company’s units sold in the IPO (not taking
into account any exercise of the Over-allotment Option)(the “IPO Base”) is 20,000,000 (the “IPO Base
Number”), will be up to an aggregate of 750,000 Shares) (pro rata based upon the percentage of the Over-allotment
Option exercised) such that immediately following such forfeiture, the Subscriber (and any other person or entity owning Class
B Common Stock) will own an aggregate number of Shares (not including Shares issuable upon exercise of any warrants or any Common
Stock purchased by Subscriber in the IPO or in the aftermarket) equal to 20% of the issued and outstanding Common Stock immediately
following the IPO.

 

3.2.         
Reduction in IPO Base Amount. In addition, in the event that the number of shares of the Company’s Class A
common stock included in the Company’s units sold in the IPO is less than the IPO Base Number, the Subscriber acknowledges
and agrees that it shall forfeit any and all rights to such number of Shares such that immediately following such forfeiture, the
Subscriber (and any other person or entity owning Class B Common Stock) will own an aggregate number of Shares (not including Shares
issuable upon exercise of any warrants or any Common Stock purchased by Subscriber in the IPO or in the aftermarket) equal to 20%
of the issued and outstanding Common Stock immediately following the IPO.

 

3.3.        
Termination of Rights as Stockholder. If any of the Shares are forfeited in accordance with this Section 3,
then after such time the Subscriber (or successor in interest), shall no longer have any rights as a holder of such Shares, and
the Company shall take such action as is appropriate to cancel such Shares.

 

4.            Waiver
of Liquidation Distributions; Redemption Rights. With respect to the Shares purchased pursuant to this Agreement, the
Subscriber hereby waives any and all right, title, interest or claim of any kind in or to any distributions by the Company
from the trust account which will be established for the benefit of the Company’s public stockholders and into which
substantially all of the proceeds of the IPO will be deposited (the “Trust Account”), in the event of a
liquidation of the Company upon the Company’s failure to timely complete an initial business combination. For purposes
of clarity, in the event the Subscriber purchases Common Stock in the IPO or in the aftermarket, any additional Common Stock
so purchased shall be eligible to receive any liquidating distributions by the Company. However, in no event will the
Subscriber have the right to redeem any Shares into funds held in the Trust Account upon the successful completion of an
initial business combination.

 

    4

     

    

 

5.           
Restrictions on Transfer.

 

5.1.         
Securities Law Restrictions. In addition to any restrictions to be contained in that certain letter agreement (commonly
known as an “Insider Letter”) to be dated as of the closing of the IPO by and among the Subscriber, the Company and
the directors and officers of the Company, the Subscriber agrees not to sell, transfer, pledge, hypothecate or otherwise dispose
of all or any part of the Shares unless, prior thereto (a) a registration statement on the appropriate form under the Securities
Act and applicable state securities laws with respect to the Shares proposed to be transferred shall then be effective or (b) the
Company has received an opinion from counsel reasonably satisfactory to the Company, that such registration is not required because
such transaction is exempt from registration under the Securities Act and the rules promulgated by the Securities and Exchange
Commission thereunder and with all applicable state securities laws.

 

5.2.         
Lock-up. The Subscriber acknowledges that the Shares will be subject to the restrictions and other provisions contained
in the Insider Letter.

 

5.3.          Restrictive Legends. All certificates or book entries representing the Shares shall have endorsed thereon legends
substantially as follows:

 

“THE SECURITIES REPRESENTED
HEREBY HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR ANY STATE SECURITIES LAWS AND NEITHER THE SECURITIES
NOR ANY INTEREST THEREIN MAY BE OFFERED, SOLD, TRANSFERRED, PLEDGED OR OTHERWISE DISPOSED OF EXCEPT PURSUANT TO AN EFFECTIVE REGISTRATION
STATEMENT UNDER SUCH ACT OR SUCH LAWS OR AN EXEMPTION FROM REGISTRATION UNDER SUCH ACT AND SUCH LAWS WHICH, IN THE OPINION OF COUNSEL,
IS AVAILABLE.”

 

“THE SECURITIES REPRESENTED
BY THIS CERTIFICATE ARE SUBJECT TO LOCKUP PROVISIONS AND MAY NOT BE OFFERED, SOLD, TRANSFERRED, PLEDGED OR OTHERWISE DISPOSED DURING
THE TERM OF THE LOCKUP PERIOD.”

 

5.4.          Additional Shares or Substituted Securities. In the event of the declaration of a stock dividend, the declaration
of a special dividend payable in a form other than Common Stock, a spin-off, a stock split, an adjustment in conversion ratio,
a recapitalization or a similar transaction affecting the Company’s outstanding Common Stock without receipt of consideration,
any new, substituted or additional securities or other property which are by reason of such transaction distributed with respect
to any Shares subject to this Section 5 or into which such Shares thereby become convertible shall immediately be subject
to this Section 5 and Section 3. Appropriate adjustments to reflect the distribution of such securities or property shall
be made to the number or class of Shares subject to this Section 5 and Section 3.

 

    5

     

    

 

5.5.          Registration Rights. The Subscriber acknowledges that the Shares are being purchased pursuant to an exemption from
the registration requirements of the Securities Act and will become freely tradable only after certain conditions are met or they
are registered pursuant to a registration rights agreement to be entered into with the Company prior to the closing of the IPO.

 

6.           
Other Agreements.

 

6.1.         
Further Assurances. The Subscriber agrees to execute such further instruments and to take such further action as
may reasonably be necessary to carry out the intent of this Agreement.

 

6.2.         
Notices. All notices, statements or other documents which are required or contemplated by this Agreement shall be
in writing and delivered: (i) personally or sent by first class registered or certified mail, overnight courier service or
facsimile or electronic transmission to the address designated in writing, (ii) by facsimile to the number most recently provided
to such party or such other address or fax number as may be designated in writing by such party or (iii) by electronic mail,
to the electronic mail address most recently provided to such party or such other electronic mail address as may be designated
in writing by such party. Any notice or other communication so transmitted shall be deemed to have been given on the day of delivery,
if delivered personally, on the business day following receipt of written confirmation, if sent by facsimile or electronic transmission,
one (1) business day after delivery to an overnight courier service or five (5) days after mailing if sent by mail.

 

6.3.         
Entire Agreement. This Agreement, together with that certain Insider Letter to be entered into by the Subscriber,
the Company and the Company’s officers and directors, substantially in the form to be filed as an exhibit to the registration
statement for the IPO, embodies the entire agreement and understanding between the Subscriber and the Company with respect to the
subject matter hereof and supersedes all prior oral or written agreements and understandings relating to the subject matter hereof.
No statement, representation, warranty, covenant or agreement of any kind not expressly set forth in this Agreement shall affect,
or be used to interpret, change or restrict, the express terms and provisions of this Agreement.

 

6.4.          Modifications
and Amendments. The terms and provisions of this Agreement may be modified or amended only by written agreement executed by
all parties hereto.

 

6.5.         
Waivers and Consents. The terms and provisions of this Agreement may be waived, or consent for the departure therefrom
granted, only by a written document executed by the party entitled to the benefits of such terms or provisions. No such waiver
or consent shall be deemed to be or shall constitute a waiver or consent with respect to any other terms or provisions of this
Agreement, whether or not similar. Each such waiver or consent shall be effective only in the specific instance and for the purpose
for which it was given, and shall not constitute a continuing waiver or consent.

 

6.6.         
Assignment. The rights and obligations under this Agreement may not be assigned by either party hereto without the
prior written consent of the other party.

 

    6

     

    

 

6.7.          Benefit. All statements, representations, warranties, covenants and agreements in this Agreement shall be binding
on the parties hereto and shall inure to the benefit of the respective successors and permitted assigns of each party hereto. Nothing
in this Agreement shall be construed to create any rights or obligations except among the parties hereto, and no person or entity
shall be regarded as a third-party beneficiary of this Agreement.

 

6.8.          Governing
Law. This Agreement and the rights and obligations of the parties hereunder shall be construed in accordance with and governed
by the laws of the State of New York applicable to contracts wholly performed within the borders of such state, without giving
effect to the conflict of law principles thereof. The parties hereto irrevocably submit to the exclusive jurisdiction of any federal
court sitting in the Southern District of New York or any state court located in New York County, State of New York, over any
suit, action or proceeding arising out of or relating to this Agreement. To the fullest extent they may effectively do so under
applicable law, the parties hereto irrevocably waive and agree not to assert, by way of motion, as a defense or otherwise, any
claim that they are not subject to the jurisdiction of any such court, any objection that they may now or hereafter have to the
laying of the venue of any such suit, action or proceeding brought in any such court and any claim that any such suit, action
or proceeding brought in any such court has been brought in an inconvenient forum.

 

6.9.          Severability.
In the event that any court of competent jurisdiction shall determine that any provision, or any portion thereof, contained in
this Agreement shall be unreasonable or unenforceable in any respect, then such provision shall be deemed limited to the extent
that such court deems it reasonable and enforceable, and as so limited shall remain in full force and effect. In the event that
such court shall deem any such provision, or portion thereof, wholly unenforceable, the remaining provisions of this Agreement
shall nevertheless remain in full force and effect.

 

6.10.       
No Waiver of Rights, Powers and Remedies. No failure or delay by a party hereto in exercising any right, power or
remedy under this Agreement, and no course of dealing between the parties hereto, shall operate as a waiver of any such right,
power or remedy of such party. No single or partial exercise of any right, power or remedy under this Agreement by a party hereto,
nor any abandonment or discontinuance of steps to enforce any such right, power or remedy, shall preclude such party from any other
or further exercise thereof or the exercise of any other right, power or remedy hereunder. The election of any remedy by a party
hereto shall not constitute a waiver of the right of such party to pursue other available remedies. No notice to or demand on a
party not expressly required under this Agreement shall entitle the party receiving such notice or demand to any other or further
notice or demand in similar or other circumstances or constitute a waiver of the rights of the party giving such notice or demand
to any other or further action in any circumstances without such notice or demand.

 

6.11.       
Survival of Representations and Warranties. All representations and warranties made by the parties hereto in this
Agreement or in any other agreement, certificate or instrument provided for or contemplated hereby, shall survive the execution
and delivery hereof and any investigations made by or on behalf of the parties.

 

6.12.        No
Broker or Finder. Each of the parties hereto represents and warrants to the other that no broker, finder or other
financial consultant has acted on its behalf in connection with this Agreement or the transactions contemplated hereby in
such a way as to create any liability on the other. Each of the parties hereto agrees to indemnify and hold the other
harmless from any claim or demand for commission or other compensation by any broker, finder, financial consultant or similar
agent claiming to have been employed by or on behalf of such party and to bear the cost of legal expenses incurred in
defending against any such claim.

 

    7

     

    

 

6.13.       
Headings and Captions. The headings and captions of the various sections of this Agreement are for convenience of
reference only and shall in no way modify or affect the meaning or construction of any of the terms or provisions hereof.

 

6.14.       
Counterparts; Electronic Signatures. This Agreement may be executed in counterparts, each of which when so executed
shall be deemed to be an original and all of which when taken together shall constitute one and the same instrument. The words
 “execution,” “signed,” “signature,” and words of like import in this Agreement or in any other
certificate, agreement or document related to this 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.

 

6.15.       
Construction. The words “include,” “includes,” and “including”
will be deemed to be followed by “without limitation.” Pronouns in masculine, feminine, and neuter genders will
be construed to include any other gender, and words in the singular form will be construed to include the plural and vice versa,
unless the context otherwise requires. The words “this Agreement,” “herein,” “hereof,”
 “hereby,” “hereunder,” and words of similar import refer to this Agreement as a whole and
not to any particular section unless expressly so limited. The parties hereto intend that each representation, warranty, and covenant
contained herein will have independent significance. If any party hereto has breached any representation, warranty, or covenant
contained herein in any respect, the fact that there exists another representation, warranty or covenant relating to the same subject
matter (regardless of the relative levels of specificity) which such party hereto has not breached will not detract from or mitigate
the fact that such party hereto is in breach of the first representation, warranty, or covenant.

 

6.16.       
Mutual Drafting. This Agreement is the joint product of the Subscriber and the Company and each provision hereof
has been subject to the mutual consultation, negotiation and agreement such parties and shall not be construed for or against any
party hereto.

 

7.            Voting
and Redemption of Shares. The Subscriber agrees to vote the Shares in favor of an initial business combination that the
Company negotiates and submits for approval to the Company’s stockholders and shall not seek redemption with respect to
the Shares. Additionally, the Subscriber agrees not to redeem any Shares in connection with a redemption or tender offer
presented to the Company’s stockholders in connection with an initial business combination negotiated by the
Company.

 

8.           
Indemnification. Each party shall indemnify (such party, the “Indemnifying Party”) the other party (such
party, the “Indemnified Party”) and its respective officers, employees, and controlling persons to the fullest extent
permitted by law from and against any and all losses, damages, expenses (including reasonable attorneys’ fees and expenses)
or other liabilities resulting from or arising out of such party’s breach of any representation, warranty, covenant or agreement
in this Agreement. The foregoing indemnification rights apply so long as the action or failure to act by the Indemnified Party
does not constitute fraud, bad faith, willful misconduct or gross negligence. Notwithstanding any of the foregoing to the contrary,
indemnification protections will not be construed so as to relieve (or attempt to relieve) any Indemnified Party of any liability
(including liability under federal securities laws which, under certain circumstances, impose liability even on persons that act
in good faith), to the extent (but only to the extent) that such liability may not be waived, modified or limited under applicable
law, but will only be construed so as to effectuate the indemnification protections to the fullest extent permitted by law.

 

[Signature Page Follows]

 

    8

     

    

 

If the foregoing accurately
sets forth our understanding and agreement, please sign the enclosed copy of this Agreement and return it to us.

 

	 	Very truly yours,
	 	 
	 	OYSTER ENTERPRISES ACQUISITION
    CORP.
	 	 
	 	By:	/s/ Michael J. Monticciolo
	 	 	Name: Michael J. Monticciolo
	 	 	Title: Chief Legal Officer, Chief Operating
 Officer and Secretary

 

	Accepted and agreed, this 16th
    day of November, 2020	 
	 	 
	OYSTER ENTERPRISES LLC	 
	 	 
	By: Oyster AG Manager LLC,
    its Manager	 
	 	 
	By:	/s/ Heath B. Freeman	 
	 	Name: Heath B. Freeman	 
	 	Member	 

 

[Signature Page
to Securities Subscription Agreement]Exhibit
10.6

 

PRIVATE PLACEMENT WARRANTS SUBSCRIPTION
AGREEMENT

 

THIS PRIVATE PLACEMENT WARRANTS SUBSCRIPTION
AGREEMENT, dated as of [●], 2021 (as it may be amended from time to time, this “Agreement”), is entered
into by and between Oyster Enterprises Acquisition Corp., a Delaware corporation (the “Company”), and Oyster
Enterprises LLC, a Delaware limited liability company (the “Purchaser”).

 

WHEREAS, the Company intends to consummate
an initial public offering of the Company’s units (the “Public Offering”), each unit consisting of one
share of the Company’s Class A common stock (“Class A Common Stock”), par value $0.0001 per share (each,
a “Share”) and one-half of one redeemable warrant, each whole warrant entitling the holder to purchase one Share
at an exercise price of $11.50 per Share (subject to adjustment), as set forth in the Company’s registration statement on
Form S-1 related to the Public Offering (the “Registration Statement”) filed with the Securities and Exchange
Commission; and

 

WHEREAS, the Purchaser has agreed to purchase
an aggregate of 4,000,000 warrants (or 4,375,000 warrants if the over-allotment option in connection with the Public Offering is
exercised in full) (the “Private Placement Warrants”), each Private Placement Warrant entitling the holder to
purchase one Share at an exercise price of $11.50 per Share (subject to adjustment), during the period commencing on the later of (i) twelve (12)
months from the date of the closing of the Public Offering and (ii) 30 days following the consummation of the Company’s initial
business combination (the “Business Combination”), as such term is defined in the Registration Statement, and
expiring on the fifth anniversary of the consummation of the Business Combination (provided that so long as the Private Placement
Warrants are held by Imperial Capital, LLC, its designees or affiliates, Imperial Capital, LLC, its designees or affiliates will
not be permitted to exercise such Private Placement Warrants after the fifth anniversary of the effective date of the Registration
Statement in accordance with Rule 5110(g)(8)(A) of the Financial Industry Regulatory Authority.

 

NOW THEREFORE, in consideration of the mutual
promises contained in this Agreement and other good and valuable consideration, the receipt and sufficiency of which are hereby
acknowledged, the parties to this Agreement hereby, intending legally to be bound, agree as follows:

 

AGREEMENT

 

Section 1. Authorization, Purchase and
Sale; Terms of the Private Placement Warrants.

 

A. Authorization of the Private
Placement Warrants. The Company has duly authorized the issuance and sale of the Private Placement Warrants to the Purchaser.

 

B. Purchase and Sale of the Private
Placement Warrants. On the date of the consummation of the Public Offering, and concurrently with the consummation thereof,
or on such earlier time and date as may be mutually agreed by the Purchaser and the Company (the “Initial Closing Date”),
the Company shall issue and sell to the Purchaser, and the Purchaser shall purchase from the Company 4,000,000 Private Placement
Warrants at a price of $1.00 per warrant for an aggregate purchase price of $4,000,000 (the “Purchase Price”),
which shall be paid by wire transfer of immediately available funds in accordance with the Company’s wiring instructions.
On the Initial Closing Date, upon payment by the Purchaser of the Purchase Price, the Company, shall either, at its option, deliver
a certificate evidencing the Private Placement Warrants purchased by the Purchaser on such date duly registered in the Purchaser’s
name to the Purchaser, or effect such delivery in book-entry form. On the date of the consummation of the closing of the over-allotment
option in connection with the Public Offering, and concurrently with the consummation thereof, or on such earlier time and date
as may be mutually agreed by the Purchaser and the Company (each such date, an “Over-allotment Closing Date”;
together with the Initial Closing Date, the “Closing Dates” and each, a “Closing Date”),
the Company shall issue and sell to the Purchaser, and the Purchaser shall purchase from the Company, up to an aggregate of 375,000
Private Placement Warrants, in the same proportion as the amount of the over-allotment option that is exercised, at a price of
$1.00 per warrant for an aggregate purchase price of up to $375,000 (if the over-allotment option in connection with the Public
Offering is exercised in full) (the “Over-allotment Purchase Price”), which shall be paid by wire transfer of
immediately available funds in accordance with the Company’s wiring instructions. On the Over-allotment Closing Date, upon
the payment by the Purchaser of the Over-allotment Purchase Price payable by it, the Company shall either, at its option, deliver
a certificate evidencing the Private Placement Warrants purchased by the Purchaser on such date duly registered in the Purchaser’s
name to the Purchaser, or effect such delivery in book-entry form.

 

     

     

    

 

C. Terms of the Private Placement
Warrants.

 

(i) The Private Placement Warrants shall
have the terms set forth in a warrant agreement to be entered into by the Company and a warrant agent, in connection with the Public
Offering (the “Warrant Agreement”).

 

(ii) At or prior to the time of the Initial
Closing Date, the Company and the Purchaser shall enter into a registration rights agreement (the “Registration Rights
Agreement”) pursuant to which the Company will grant certain registration rights to the Purchaser relating to the Private
Placement Warrants and the Shares underlying the Private Placement Warrants.

 

Section 2. Representations and Warranties
of the Company. As a material inducement to the Purchaser to enter into this Agreement and purchase the Private Placement
Warrants, the Company hereby represents and warrants to the Purchaser (which representations and warranties shall survive each
Closing Date) that:

 

A. Organization and Corporate Power.
The Company is a corporation duly incorporated, validly existing and in good standing under the laws of the State of Delaware and
is qualified to do business in every jurisdiction in which the failure to so qualify would reasonably be expected to have a material
adverse effect on the financial condition, operating results or assets of the Company. The Company possesses all requisite corporate
power and authority necessary to carry out the transactions contemplated by this Agreement and the Warrant Agreement.

 

B. Authorization; No Breach.

 

(i) The execution, delivery and performance
of this Agreement and the Private Placement Warrants have been duly authorized and approved by the Company as of each Closing Date.
This Agreement constitutes a valid and binding obligation of the Company, enforceable against the Company in accordance with its
terms, subject to bankruptcy, insolvency, fraudulent conveyance, reorganization, moratorium and other laws of general applicability
relating to or affecting creditors’ rights and to general equitable principles (whether considered in a proceeding in equity
or law) (the “Enforceability Exceptions”). Upon issuance in accordance with, and payment pursuant to, the terms
of the Warrant Agreement and this Agreement, the Private Placement Warrants will constitute valid and binding obligations of the
Company, enforceable against the Company in accordance with their terms, subject to the Enforceability Exceptions.

 

(ii) The execution and delivery by the Company
of this Agreement and the Private Placement Warrants, the issuance and sale of the Private Placement Warrants, the issuance of
the Shares upon exercise of the Private Placement Warrants and the fulfillment of, and compliance with, the respective terms hereof
and thereof by the Company, do not and will not as of each Closing Date (a) (A) conflict with or result in a breach of the terms,
conditions or provisions of, (B) constitute a default under, (C) result in the creation of any lien, security interest, charge
or encumbrance upon the Company’s capital stock or assets under, or (D) result in a violation of, the certificate of incorporation
or the bylaws of the Company (in effect on the date hereof or as may be amended prior to completion of the Public Offering), or
any material law, statute, rule or regulation to which the Company is subject, or any agreement, order, judgment or decree to which
the Company is subject, or (b) require any authorization, consent, approval, exemption, action, notice, declaration or filing,
in each case, by or to any court or administrative or governmental body or agency, except for any filings required after the date
hereof under federal or state securities laws.

 

C. Title to Securities. Upon
issuance in accordance with, and payment pursuant to, the terms hereof and the Warrant Agreement, the Placement Warrants will be
duly and validly issued and the Shares issuable upon exercise of the Private Placement Warrants will be duly and validly issued,
fully paid and nonassessable. On the date of issuance of the Private Placement Warrants, the Shares issuable upon exercise of the
Private Placement Warrants shall have been reserved for issuance. Upon issuance in accordance with, and payment pursuant to, the
terms hereof and the Warrant Agreement, the Purchaser will have good title to the Private Placement Warrants and the Shares issuable
upon exercise of such Private Placement Warrants, free and clear of all liens, claims and encumbrances of any kind, other than
(i) transfer restrictions hereunder and under the other agreements contemplated hereby, (ii) transfer restrictions under federal
and state securities laws, and (iii) liens, claims or encumbrances imposed due to the actions of the Purchaser.

 

D. Valid Issuance. The
total number of shares of all classes of capital stock which the Company has authority to issue is 111,000,000 shares of
common stock (which consist of 100,000,000 shares of Class A Common Stock and 10,000,000 shares of the Company’s Class
B common stock, par value $0.0001 per share (the “Class B Common Stock”)) and 1,000,000 shares of the
Company’s preferred stock, par value $0.0001, per share (the “Preferred Stock”). As of the date
hereof, the Company has issued and outstanding no shares of Class A Common Stock, 5,750,000 shares of Class B Common Stock
(of which up to 750,000 shares are subject to forfeiture as described in the Registration Statement) and no shares of
Preferred Stock. All of the issued shares of capital stock of the Company have been duly authorized, validly issued, and are
fully paid and non-assessable.

 

    2

     

    

 

Section 3. Representations and Warranties
of the Purchaser. As a material inducement to the Company to enter into this Agreement and issue and sell the Private
Placement Warrants to the Purchaser, the Purchaser hereby represents and warrants to the Company (which representations and warranties
shall survive each Closing Date) that:

 

A. Organization and Requisite Authority.
The Purchaser is duly organized, validly existing and in good standing under the laws of the State of Delaware and possesses all
requisite power and authority necessary to carry out the transactions contemplated by this Agreement.

 

B. Authorization; No Breach.

 

(i) This Agreement constitutes a valid and
binding obligation of the Purchaser, enforceable against the Purchaser in accordance with its terms, except subject to the Enforceability
Exceptions.

 

(ii) The execution and delivery by the Purchaser
of this Agreement and the fulfillment of and compliance with the terms hereof by the Purchaser does not and shall not as of each
Closing Date conflict with, violate, or result in a breach by the Purchaser of the terms, conditions or provisions of, or constitute
a default under the charter or bylaws or other organizational documents of the Purchaser, or any agreement, instrument, order,
judgment or decree to which the Purchaser is subject.

 

C. Investment Representations.

 

(i) The Purchaser is acquiring the Private
Placement Warrants and, upon exercise of the Private Placement Warrants, the Shares issuable upon such exercise (the Private Placement
Warrants and such Shares, the “Securities”), for the Purchaser’s own account, for investment purposes
only and not with a view towards, or for resale in connection with, any public sale or distribution thereof.

 

(ii) The Purchaser is an “accredited
investor” as such term is defined in Rule 501(a)(3) of Regulation D under the Securities Act of 1933, as amended (the “Securities
Act”).

 

(iii) The Purchaser understands that the
Securities are being offered and will be sold to it in reliance on specific exemptions from the registration requirements of the
United States federal and state securities laws and that the Company is relying upon the truth and accuracy of, and the Purchaser’s
compliance with, the representations and warranties of the Purchaser set forth herein in order to determine the availability of
such exemptions and the eligibility of the Purchaser to acquire such Securities.

 

(iv) The Purchaser did not enter into this
Agreement as a result of any general solicitation or general advertising within the meaning of Rule 502(c) under the Securities
Act.

 

(v) The Purchaser has been furnished with
all materials relating to the business, finances and operations of the Company and materials relating to the offer and sale of
the Securities which have been requested by the Purchaser. The Purchaser has been afforded the opportunity to ask questions of
the executive officers and directors of the Company. The Purchaser understands that its investment in the Securities involves a
high degree of risk and it has sought such accounting, legal and tax advice as it has considered necessary to make an informed
investment decision with respect to the acquisition of the Securities.

 

(vi) The Purchaser understands that no
United States federal or state agency or any other government or governmental agency has passed on or made any recommendation
or endorsement of the Securities or the fairness or suitability of the investment in the Securities by the Purchaser nor have
such authorities passed upon or endorsed the merits of the offering of the Securities. 

 

    3

     

    

 

(vii) The Purchaser understands that: (a)
the Securities have not been and are not being registered under the Securities Act or any state securities laws, and may not be
offered for sale, sold, assigned or transferred unless (1) subsequently registered thereunder or (2) sold in reliance on an exemption
therefrom; and (b) except as specifically set forth in the Registration Rights Agreement, neither the Company nor any other person
is under any obligation to register the Securities under the Securities Act or any state securities laws or to comply with the
terms and conditions of any exemption thereunder. While such Purchaser understands that Rule 144 under the Securities Act is not
available for the resale of securities initially issued by shell companies (other than business combination related shell companies)
or issuers that have been at any time previously a shell company, such Purchaser understands that Rule 144 includes an exception
to this prohibition if the following conditions are met: (i) the issuer of the securities that was formerly a shell company has
ceased to be a shell company; (ii) the issuer of the securities is subject to the reporting requirements of Section 13 or 15(d)
of the Securities Exchange Act of 1934, as amended (the “Exchange Act”); (iii) the issuer of the securities
has filed all Exchange Act reports and material required to be filed, as applicable, during the preceding 12 months (or such shorter
period that the issuer was required to file such reports and materials), other than Form 8-K reports; and (iv) at least one year
has elapsed from the time that the issuer filed current Form 10 type information with the SEC reflecting its status as an entity
that is not a shell company.

 

(viii) The Purchaser understands the high
degree of risk associated with investments in the securities of companies in the development stage such as the Company, has such
knowledge and experience in financial and business matters to be able to evaluate the merits and risks of an investment in the
Securities and is able to bear the economic risk of an investment in the Securities in the amount contemplated hereunder for an
indefinite period of time. The Purchaser has adequate means of providing for its current financial needs and contingencies and
will have no current or anticipated future needs for liquidity which would be jeopardized by the investment in the Securities.
The Purchaser can afford a complete loss of its investment in the Securities.

 

Section 4. Conditions of the Purchaser’s
Obligations. The obligations of the Purchaser to purchase and pay for the Private Placement Warrants are subject to the
fulfillment, on or before each Closing Date, of each of the following conditions:

 

A. Representations and Warranties.
The representations and warranties of the Company contained in Section 2 shall be true and correct at and as of such Closing Date
as though then made.

 

B. Performance. The Company
shall have performed and complied with all agreements, obligations and conditions contained in this Agreement that are required
to be performed or complied with by it on or before such Closing Date.

 

C. No Injunction. No litigation,
statute, rule, regulation, executive order, decree, ruling or injunction shall have been enacted, entered, promulgated or endorsed
by or in any court or governmental authority of competent jurisdiction or any self-regulatory organization having authority over
the matters contemplated hereby, which prohibits the consummation of any of the transactions contemplated by this Agreement or
the Warrant Agreement.

 

D. Warrant Agreement and Registration
Rights Agreement. The Company shall have entered into the Warrant Agreement and the Registration Rights Agreement, each on
terms satisfactory to the Purchaser.

  

E. Corporate Consents. The Company
shall have obtained the consent of its Board of Directors authorizing the execution, delivery and performance of this Agreement
and the Warrant Agreement and the issuance and sale of the Private Placement Warrants hereunder.

 

Section 5. Conditions of the Company’s
Obligations. The obligations of the Company to the Purchaser under this Agreement are subject to the fulfillment, on or
before each Closing Date, of each of the following conditions:

 

A. Representations and Warranties.
The representations and warranties of the Purchaser contained in Section 3 shall be true and correct at and as of such Closing
Date as though then made.

 

    4

     

    

 

B. Performance. The Purchaser
shall have performed and complied with all agreements, obligations and conditions contained in this Agreement that are required
to be performed or complied with by the Purchaser on or before such Closing Date.

 

C. Corporate Consents. The Company
shall have obtained the consent of its Board of Directors authorizing the execution, delivery and performance of this Agreement
and the Warrant Agreement and the issuance and sale of the Private Placement Warrants hereunder.

 

D. No Injunction. No litigation,
statute, rule, regulation, executive order, decree, ruling or injunction shall have been enacted, entered, promulgated or endorsed
by or in any court or governmental authority of competent jurisdiction or any self-regulatory organization having authority over
the matters contemplated hereby, which prohibits the consummation of any of the transactions contemplated by this Agreement or
the Warrant Agreement.

 

E. Warrant Agreement. The Company
shall have entered into the Warrant Agreement on terms satisfactory to the Company.

 

Section 6. Survival of Representations
and Warranties. All of the representations and warranties contained herein shall survive each Closing Date.

 

Section 7. Definitions. Terms
used but not otherwise defined in this Agreement shall have the meaning assigned to such terms in the Registration Statement.

 

Section 8. Miscellaneous.

 

A. Successors and Assigns. Except
as otherwise expressly provided herein, all covenants and agreements contained in this Agreement by or on behalf of any of the
parties hereto shall bind and inure to the benefit of the respective successors of the parties hereto whether so expressed or not.
Notwithstanding the foregoing or anything to the contrary herein, the parties may not assign this Agreement without the prior written
consent of the other party hereto, other than assignments by the Purchaser to affiliates thereof (including, without limitation,
one or more of its members).

  

B. Severability. Whenever possible,
each provision of this Agreement shall be interpreted in such manner as to be effective and valid under applicable law, but if
any provision of this Agreement is held to be prohibited by or invalid under applicable law, such provision shall be ineffective
only to the extent of such prohibition or invalidity, without invalidating the remainder of this Agreement.

 

C. Counterparts. This Agreement
may be executed in counterparts, each of which when so executed shall be deemed to be an original and all of which when taken together
shall constitute one and the same instrument. The words “execution,” “signed,” “signature,”
and words of like import in this Agreement or in any other certificate, agreement or document related to this 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.

 

D. Descriptive Headings; Interpretation.
The descriptive headings of this Agreement are inserted for convenience only and do not constitute a substantive part of this Agreement.
The use of the word “including” in this Agreement shall be by way of example rather than by limitation.

 

    5

     

    

 

E. Governing Law. This Agreement
shall be deemed to be a contract made under the laws of the State of New York and for all purposes shall be construed in accordance
with the internal laws of the State of New York without regard to the conflicts of laws principles thereof.

 

F. Amendments. This Agreement
may not be amended, modified or waived as to any particular provision, except by a written instrument executed by all parties hereto.

 

[Signature Page Follows]

 

    6

     

    

 

IN WITNESS WHEREOF, the parties hereto
have executed this Agreement to be effective as of the date first set forth above.

 

	 	COMPANY:
	 	 
	 	OYSTER ENTERPRISES ACQUISITION CORP.
	 	 
	 	
        By:
	
	 	 	Name:

Title:
	 	 	 
	 	PURCHASER:
	 	 
	 	
        OYSTER ENTERPRISES LLC

        By: Oyster AG Manager LLC, its Manager

        

	 	 	 
	 	By:	 
	 	 	Name:

Title:

 

[Signature Page to Private Placement Warrants Subscription
Agreement (Sponsor)]

Source: [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00318-of-00352.parquet"}, [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00318-of-00352.parquet"}]]