Document:

Exhibit
10.1

 

EXECUTION
VERSION

 

AMENDMENT
AND EXCHANGE AGREEMENT

 

This
Amendment and Exchange Agreement (the “Agreement”) is entered into as of the 22nd day of September, 2022, by and among
Gaucho Group Holdings, Inc., a Delaware corporation (the “Company”) and the investor signatory hereto (the “Holder”),
with reference to the following facts:

 

A.
Prior to the date hereof, pursuant to that Securities Purchase Agreement, dated as of November 3, 2021, by and between the Company and
the investors (including the Holder, the “Holders”) (as the same has been amended, restated, amended and restated,
supplemented or otherwise modified prior to the date hereof, the “Securities Purchase Agreement”), the Company issued
to the Holders certain senior secured convertible notes (as the same has been amended, restated, amended and restated, supplemented or
otherwise modified prior to the date hereof, each, an “Existing Note” and together with the Securities Purchase Agreement,
the “Existing Note Documents”). Capitalized terms used but not otherwise defined herein shall have the meanings as
set forth in the Securities Purchase Agreement (as amended hereby) or, as the context may require, the Existing Notes.

 

B.
As of the date of this Agreement, the Holder is the holder of such aggregate principal amount of Existing Notes as set forth on the signature
page of the Holder attached hereto and has not assigned, transferred or exchanged any of its Existing Notes.

 

C.
The Company and the Holder desire to amend and waive certain provisions of the Existing Note Documents and exchange (the “Exchange”
or the “Transaction”) $100 in aggregate principal amount of the Existing Note (the “Exchange Note”),
on the basis and subject to the terms and conditions set forth in this Agreement, for a warrant, in the form attached hereto as Exhibit
A (the “New Warrant”), exercisable into such aggregate number of shares of Common Stock of the Company as
set forth on the signature page of the Holder attached hereto (the “New Warrant Shares”, and together with the New
Warrant, collectively, the “New Securities”).

 

D.
The New Warrant and this Agreement and such other documents and certificates related thereto are collectively referred to herein as the
“Exchange Documents”.

 

E.
The Exchange is being made in reliance upon the exemption from registration provided by Section 3(a)(9) of the Securities Act of 1933,
as amended (the “Securities Act”).

 

NOW,
THEREFORE, in consideration of the foregoing premises and the mutual covenants hereinafter contained, the parties hereto agree as follows:

 

1.
Exchange. On the Closing Date (as defined below), subject to the terms and conditions of this Agreement, pursuant to Section
3(a)(9) of the Securities Act, the Holder shall convey, assign and transfer the Exchange Note to the Company in exchange for which the
Company shall issue the New Warrant to the Holder. On the Closing Date, in exchange for the Exchange Note, the Company shall deliver
or cause to be delivered to the Holder (or its designee) the New Warrant at the address for delivery set forth on the signature page
of the Holder attached hereto. Immediately following the delivery of the New Warrant to the Holder (or its designee), the Holder shall
relinquish all rights, title and interest in the Exchange Note (including any claims the Holder may have against the Company related
thereto) and assign the same to the Company, and the Exchange Note shall be deemed canceled.

 

    	 

    	 

    

 

2.
Ratifications; Incorporation of Terms under Transaction Documents.

 

(a)
Ratifications. Except as otherwise expressly provided herein, the Securities Purchase Agreement and each other Transaction Document,
is, and shall continue to be, in full force and effect and is hereby ratified and confirmed in all respects, except that on and after
the date hereof: (i) all references in the Securities Purchase Agreement to “this Agreement”, “hereto”, “hereof”,
“hereunder” or words of like import referring to the Securities Purchase Agreement shall mean the Securities Purchase Agreement
as amended by this Agreement, and (ii) all references in the other Transaction Documents to the “Securities Purchase Agreement”,
“thereto”, “thereof”, “thereunder” or words of like import referring to the Securities Purchase Agreement
shall mean the Securities Purchase Agreement as amended by this Agreement.

 

(b)
Amendments to Securities Purchase Agreement. Effective as of the date hereof, the Securities Purchase Agreement is hereby amended
as follows (and any such agreements, covenants and related provisions therein shall be deemed incorporated by reference herein, mutatis
mutandis, as amended as such):

 

(i)
Section 4(k) of the Agreement is hereby amended and restated in its entirety as follows:

 

(k
) Additional Issuance of Securities. So long as any Buyer beneficially owns any Securities, the
Company will not, without the prior written consent of the Required Holders, issue any Notes (other than to the Buyers as contemplated
hereby) and the Company shall not issue any other securities that would cause a breach or default under the Notes. Unless otherwise agreed
upon in writing by the Buyers, for the period commencing on the date hereof and ending on the date immediately following the 90th
Trading Day after the Applicable Date (provided that such period shall be extended by the number of calendar days during such period
and any extension thereof contemplated by this proviso on which any Registration Statement is not effective or any prospectus contained
therein is not available for use or any Current Public Information Failure exists) (the “Restricted Period”), neither
the Company nor any of its Subsidiaries shall directly or indirectly issue, offer, sell, grant any option or right to purchase, or otherwise
dispose of (or announce any issuance, offer, sale, grant of any option or right to purchase or other disposition of) any equity security
or any equity-linked or related security (including, without limitation, any “equity security” (as that term is defined under
Rule 405 promulgated under the 1933 Act), any Convertible Securities (as defined below), any debt, any preferred stock or any purchase
rights) (any such issuance, offer, sale, grant, disposition or announcement (whether occurring during the Restricted Period or at any
time thereafter) is referred to as a “Subsequent Placement”). Notwithstanding the foregoing, this Section 4(k) shall
not apply in respect of the issuance of (i) shares of Common Stock or standard options to purchase Common Stock to directors, officers,
consultants or employees of the Company in their capacity as such pursuant to an Approved Stock Plan (as defined below), provided that
(1) all such issuances (taking into account the shares of Common Stock issuable upon exercise of such options) after the date hereof
pursuant to this clause (i) do not, in the aggregate, exceed more than 5% of the Common Stock issued and outstanding immediately prior
to the date hereof and (2) the exercise price of any such options is not lowered, none of such options are amended to increase the number
of shares issuable thereunder and none of the terms or conditions of any such options are otherwise materially changed in any manner
that adversely affects any of the Buyers; (ii) shares of Common Stock issued upon the conversion or exercise of Convertible Securities
(other than standard options to purchase Common Stock issued pursuant to an Approved Stock Plan that are covered by clause (i) above)
issued prior to the date hereof, provided that the conversion, exercise or other method of issuance (as the case may be) of any such
Convertible Security is made solely pursuant to the conversion, exercise or other method of issuance (as the case may be) provisions
of such Convertible Security that were in effect on the date immediately prior to the date of this Agreement, the conversion, exercise
or issuance price of any such Convertible Securities (other than standard options to purchase Common Stock issued pursuant to an Approved
Stock Plan that are covered by clause (i) above) is not lowered, none of such Convertible Securities (other than standard options to
purchase Common Stock issued pursuant to an Approved Stock Plan that are covered by clause (i) above) are amended to increase the number
of shares issuable thereunder and none of the terms or conditions of any such Convertible Securities (other than standard options to
purchase Common Stock issued pursuant to an Approved Stock Plan that are covered by clause (i) above) are otherwise materially changed
in any manner that adversely affects any of the Buyers; (iii) shares of Common Stock issued pursuant to that certain Common Stock Purchase
Agreement and Registration Rights Agreement with Tumim Stone Capital dated May 6, 2021 and any subsequent equity line of credit mutually
agreed upon with Tumim Stone Capital (the “Permitted Equity Line”); (iv) 1,414,679 shares of Common Stock issued (or
issuable) pursuant to the GGI Transaction, the HBH Transaction, and the WOW Transaction; (v) 5,454,909 shares of Common Stock and warrants
to purchase 5,454,909 shares of Common Stock pursuant to the terms of those certain notes which converted on August 30, 2022; (vi) shares
of Common Stock and warrants to purchase shares of Common Stock to be issued in connection with a pending private placement of up to
$1,800,000 gross proceeds at a price per share not less than Minimum Price as defined by Nasdaq Rule 5635(d); (vii) any shares of Common
Stock issued or issuable in connection with any bona fide strategic or commercial alliances, acquisitions, mergers, licensing arrangements,
and strategic partnerships, provided, that (x) the primary purpose of such issuance is not to raise capital as reasonably determined,
and (y) the purchaser or acquirer or recipient of the securities in such issuance solely consists of either (I) the actual participants
in such strategic or commercial alliance, strategic or commercial licensing arrangement or strategic or commercial partnership, (II)
the actual owners of such assets or securities acquired in such acquisition or merger or (III) the stockholders, partners, employees,
consultants, officers, directors or members of the foregoing Persons, in each case, which is, itself or through its subsidiaries, an
operating company or an owner of an asset, in a business synergistic with the business of the Company and shall provide to the Company
additional benefits in addition to the investment of funds, and (z) the number or amount of securities issued to such Persons by the
Company shall not be disproportionate to each such Person’s actual participation in (or fair market value of the contribution to)
such strategic or commercial alliance or strategic or commercial partnership or ownership of such assets or securities to be acquired
by the Company, as applicable and (viii) the Conversion Shares, (each of the foregoing in clauses (i) through (viii), collectively the
“Excluded Securities”) and (ix) subject to the Company’s compliance with Section 10 of the Note (including,
without limitation, the issuances of Subsequent Warrants (as defined in the Note) to the Buyers in connection therewith as required thereunder,
if applicable), any bone fide public offering of Common Stock and/or Options of the Company. “Approved Stock Plan”
means any employee benefit plan which has been approved by the board of directors of the Company prior to or subsequent to the date hereof
pursuant to which shares of Common Stock and standard options to purchase Common Stock may be issued to any employee, consultant, officer
or director for services provided to the Company in their capacity as such. 

 

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3.
Limited Waivers.

 

a.
The Holder hereby waives, in part, the Amortizations (as defined in the Existing Notes) required on September 7, 2022 and October 7,
2022, such that (x) only the accrued and unpaid interest on such applicable Amortization Amount with respect to each such Amortization
Date (as defined in the Existing Notes) shall be due and payable on such Amortization Date (for the avoidance of doubt, excluding the
Amortization Amount and Make-Whole Amounts included in each such Amortization Redemption Amount (as defined in the Existing Notes) and
otherwise due and payable on each such Amortization Date (the “Remaining Amortization Amount”), and (y) the Remaining
Amortization Amount for each such Amortization Date shall be allocated among the remaining Amortization Dates, pro rata, increasing the
Amortization Amount (as defined in the Existing Notes) for each such remaining Amortization Dates from such existing Amortization Amount
as set forth on the signature page of the Holder attached hereto to such new Amortization Amount as set forth on the signature page of
the Holder attached hereto.

 

b.
The Holder hereby waives the requirement in Section 4(d) regarding use of proceeds from the sale of the Securities but not with respect
to any other subsequent placement of securities to pay off in full the loan set forth on Schedule 4(d)(i) as of November 9, 2021, subject
to payment in full of the loan on or before October 19, 2022.

 

c.
The Holder hereby waives all breaches which have occurred under the terms of the Existing Note Documents (as the same has been amended,
restated, amended and restated, supplemented or otherwise modified prior to the date hereof) through and including the date of execution
of this Agreement as set forth on Schedule 3(c) of this Agreement.

 

d.
Notwithstanding anything in the Existing Notes or this Agreement to the contrary, including, without limitation, Section 2 of the Existing
Notes, the Company and the Holder hereby acknowledge and agree that, as provided in Section 12 of the Existing Notes, accrued and unpaid
Interest on each Existing Note is due and payable on each Amortization Date.

 

4.
Company Representations and Warranties. As of the date hereof and as of the Closing Date (as defined below):

 

4.1.
Each of the Company and each of its Subsidiaries are entities duly organized and validly existing and in good standing under the laws
of the jurisdiction in which they are formed, and have the requisite power and authority to own their properties and to carry on their
business as now being conducted and as presently proposed to be conducted. Each of the Company and each of its Subsidiaries is duly qualified
as a foreign entity to do business and is in good standing in every jurisdiction in which the character of the properties owned or leased
by it or the nature of the business conducted by it makes such qualification necessary, except to the extent that the failure to be so
qualified or be in good standing would not reasonably be expected to have a Material Adverse Effect (as defined below). As used in this
Agreement, “Material Adverse Effect” means any material adverse effect on (i) the business, properties, assets, liabilities,
operations (including results thereof), condition (financial or otherwise) or prospects of the Company and its Subsidiaries, taken as
a whole, (ii) the transactions contemplated hereby or in any of the other Exchange Documents or any other agreements or instruments to
be entered into in connection herewith or therewith or (iii) the authority or ability of the Company or any of its Subsidiaries to perform
any of their respective obligations under any of the Exchange Documents (as defined below). Other than the Persons set forth on Schedule
3(a) of the Securities Purchase Agreement, the Company has no subsidiaries.

 

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4.2.
Authorization and Binding Obligation. The Company has the requisite power and authority to enter into and perform its obligations
under this Agreement, the New Warrant and each of the other agreements entered into by the parties hereto in connection with the transactions
contemplated by the Exchange Documents and to consummate the Transaction (including, without limitation, the issuance of the New Warrant
in accordance with the terms hereof and thereof). As of the Closing Date, the execution and delivery of the Exchange Documents by the
Company and the consummation by the Company of the transactions contemplated hereby and thereby, including, without limitation, the issuance
of the New Warrant and the reservation for issuance and issuance of the New Warrant Shares issuable upon exercise of the New Warrant
will have been duly authorized by the Company’s Board of Directors (or a duly authorized committee thereof) and no further filing,
consent, or authorization will be required by the Company, its Board of Directors or its stockholders (other than such filings as may
be required by any federal or state securities laws, rules or regulations). This Agreement has been and, as of the Closing Date, the
other Exchange Documents to which the Company is a party will have been, duly executed and delivered by the Company, and constitute or
will constitute, as applicable, the legal, valid and binding obligations of the Company, enforceable against the Company in accordance
with their respective terms, except as such enforceability may be limited by general principles of equity or applicable bankruptcy, insolvency,
reorganization, moratorium, liquidation or similar laws relating to, or affecting generally, the enforcement of applicable creditors’
rights and remedies and except as rights to indemnification and to contribution may be limited by federal or state securities laws.

 

4.3.
No Conflict. The execution, delivery and performance of the Exchange Documents by the Company and the consummation by the Company
of the transactions contemplated hereby and thereby (including, without limitation, the issuance of the New Warrant and reservation for
issuance and issuance of the New Warrant Shares) will not (i) result in a violation of its Certificate of Incorporation or any other
organizational documents of the Company or any of its Subsidiaries, any capital stock of the Company or any of its Subsidiaries or Bylaws
of the Company or any of its Subsidiaries, (ii) conflict with, or constitute a default (or an event which with notice or lapse of time
or both would become a default) under, or give to others any rights of termination, amendment, acceleration or cancellation of, any agreement,
indenture or instrument to which the Company or any of its Subsidiaries is a party, after giving effect to the consent and limited waiver
contained in Section 3 above and the receipt by the Company of the Required Consents (as defined below), or (iii) result in a violation
of any law, rule, regulation, order, judgment or decree (including foreign, federal and state securities laws and regulations and the
rules and regulations of the Nasdaq Capital Markets LLC (the “Principal Market”) and including all applicable federal
laws, rules and regulations) applicable to the Company or any of its Subsidiaries or by which any property or asset of the Company or
any of its Subsidiaries is bound or affected except, in the case of clause (ii) or (iii) above, to the extent such violations that would
not reasonably be expected to have a Material Adverse Effect.

 

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4.4.
No Consents. Except as set forth on Schedule 4.4 (the “Required Consents”), neither the Company nor any Subsidiary
is required to obtain any consent from, authorization or order of, or make any filing or registration with (other than such filings as
may be required by any federal or state securities laws, rules or regulations or any Nasdaq rules), any Governmental Entity or any regulatory
or self-regulatory agency or any other Person in order for it to execute, deliver or perform any of its respective obligations under
or contemplated by the Exchange Documents, in each case, in accordance with the terms hereof or thereof. All consents, authorizations,
orders, filings and registrations which the Company or any Subsidiary is required to obtain pursuant to the preceding sentence have been
or will be obtained or effected on or prior to the Closing Date, and neither the Company nor any of its Subsidiaries are aware of any
facts or circumstances which might prevent the Company or any of its Subsidiaries from obtaining or effecting any of the registration,
application or filings contemplated by the Exchange Documents.

 

4.5.
Securities Law Exemptions. Assuming the accuracy of the representations and warranties of the Holder contained herein, the offer
and issuance by the Company of the New Securities is exempt from registration under the Securities Act pursuant to the exemption provided
by Section 3(a)(9) of the Securities Act thereof.

 

4.6.
Status of Existing Notes; Issuance of New Securities.

 

(a)
The Company has no knowledge that any Existing Note is subject to dispute and to the knowledge of the Company there is no action based
on any Existing Note that is currently pending in any court or other legal venue and to the knowledge of the Company no judgments based
upon any Existing Note have been previously entered in any legal proceeding. The Company has not received any written notice from the
Holder or any other person challenging or disputing any Existing Note, or any portion thereof, and prior to the Exchange, the Company
is unconditionally obligated to pay the entire aggregate principal amount outstanding under the Existing Notes (and any accrued and unpaid
interest thereunder) without defense, counterclaim or offset.

 

(b)
As of the Closing Date, the issuance of the New Warrant will be duly authorized and upon issuance in accordance with the terms of the
Exchange Documents shall be validly issued, fully paid and non-assessable and free from all Liens (as defined in the Existing Notes).
Upon issuance upon exchange, in accordance with the New Warrant, the New Warrant Shares, when issued, will be validly issued, fully paid
and nonassessable and free from all Liens with respect to the issue thereof, with the Holder being entitled to all rights accorded to
a holder of Common Stock. By virtue of Section 3(a)(9) under the Securities Act, the New Warrant will have a Rule 144 holding period
that will be deemed to have commenced as of the Closing Date (as defined in the Securities Purchase Agreement), the date of the original
issuance of the Existing Notes to the Holders. At any time on and after May 9, 2022, assuming (i) the Holder is not an affiliate of the
Company and (ii) at such time of determination the Company has not failed to satisfy the requirements of Rule 144(c)(1), including, without
limitation, the failure to satisfy the current public information requirement under Rule 144(c) (a “Current Public Information
Failure”), (A) the New Warrant shall not be required to bear any restrictive legend and shall be freely transferable by the
Holder pursuant to and in accordance with Rule 144 of the Securities Act (“Rule 144”) and (B) to the extent any applicable
New Warrant Shares are issued pursuant to a “cashless exercise” of the New Warrant, such New Warrant Shares shall not be
required to bear any restrictive legend and shall be freely transferable by the Holder pursuant to and in accordance with Rule 144.

 

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4.7.
Transfer Taxes. On the Closing Date, all share transfer or other taxes (other than income or similar taxes) that are required
to be paid in connection with the issuance of the New Warrant to be issued to the Holder hereunder will be, or will have been, fully
paid or provided for by the Company, and all laws imposing such taxes will be or will have been complied with.

 

4.8.
Conduct of Business; Regulatory Permits. Neither the Company nor any of its Subsidiaries is in material violation of any term
of or in default under its Certificate of Incorporation, any certificate of designation, preferences or rights of any other outstanding
series of preferred stock of the Company or any of its Subsidiaries or Bylaws or their organizational charter, certificate of formation,
memorandum of association, articles of association, Certificate of Incorporation or certificate of incorporation or bylaws, respectively.
Neither the Company nor any of its Subsidiaries is in material violation of any judgment, decree or order or any statute, ordinance,
rule or regulation applicable to the Company or any of its Subsidiaries, and neither the Company nor any of its Subsidiaries will conduct
its business in violation of any of the foregoing, except in all cases for possible violations which would not, individually or in the
aggregate, reasonably be expected to have a Material Adverse Effect. Without limiting the generality of the foregoing, except as set
forth in the SEC Documents, the Company is not in material violation of any of the rules, regulations or requirements of the Principal
Market and has no knowledge of any facts or circumstances that could reasonably lead to delisting or suspension of the Common Stock by
the Principal Market in the foreseeable future. Except as set forth in SEC Documents, during the two years prior to the date hereof,
(i) the Common Stock has been listed or designated for quotation on the Principal Market, (ii) trading in the Common Stock has not been
suspended by the Securities and Exchange Commission (“SEC”) or the Principal Market and (iii) the Company has received
no communication, written or oral, from the SEC or the Principal Market regarding the suspension or delisting of the Common Stock from
the Principal Market. The Company and each of its Subsidiaries possess all certificates, authorizations and permits issued by the appropriate
regulatory authorities necessary to conduct their respective businesses, except where the failure to possess such certificates, authorizations
or permits would not, individually or in the aggregate, reasonably be expected to have a Material Adverse Effect, and neither the Company
nor any such Subsidiary has received any notice of proceedings relating to the revocation or modification of any such certificate, authorization
or permit. There is no agreement, commitment, judgment, injunction, order or decree binding upon the Company or any of its Subsidiaries
or to which the Company or any of its Subsidiaries is a party which has or would reasonably be expected to have the effect of prohibiting
or materially impairing any business practice of the Company or any of its Subsidiaries, any acquisition of property by the Company or
any of its Subsidiaries or the conduct of business by the Company or any of its Subsidiaries as currently conducted other than such effects,
individually or in the aggregate, which have not had and would not reasonably be expected to have a Material Adverse Effect on the Company
or any of its Subsidiaries.

 

4.9.
No Consideration Paid. No consideration, commission or other remuneration has been paid by the Holder to the Company, its Subsidiaries
or any of their agents or affiliates in connection with the Exchange.

 

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4.10.
Disclosure. The Company confirms that neither it nor any other Person acting on its behalf has provided the Holder or its agents
or counsel with any information that constitutes or could reasonably be expected to constitute material, non-public information concerning
the Company or any of its Subsidiaries, other than the existence of the transactions contemplated by this Agreement and the other Exchange
Documents and any matters disclosed in the 8-K Filing (as defined below). The Company understands and confirms that the Holder will rely
on the foregoing representations in effecting transactions in securities of the Company.

 

5.
Holder’s Representations and Warranties. As a material inducement to the Company to enter into this Agreement and consummate
the Exchange, the Holder hereby represents and warrants with and to the Company, as of the date hereof and as of the Closing Date, as
follows:

 

5.1
Reliance on Exemptions. The Holder understands that the New Securities are being offered and exchanged 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 the Holder’s compliance with, the representations, warranties, agreements, acknowledgments
and understandings of the Holder set forth herein and in the other Exchange Documents in order to determine the availability of such
exemptions and the eligibility of the Holder to acquire the New Securities.

 

5.2
No Governmental Review. The Holder 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 New Securities or the fairness or suitability of the investment
in the New Securities nor have such authorities passed upon or endorsed the merits of the offering of the New Securities.

 

5.3
Validity; Enforcement. This Agreement and the other Exchange Documents to which the Holder is a party have been duly and validly
authorized, executed and delivered on behalf of the Holder and shall constitute the legal, valid and binding obligations of the Holder
enforceable against the Holder in accordance with their respective terms, except as such enforceability may be limited by general principles
of equity or to applicable bankruptcy, insolvency, reorganization, moratorium, liquidation and other similar laws relating to, or affecting
generally, the enforcement of applicable creditors’ rights and remedies.

 

5.4
No Conflicts. The execution, delivery and performance by the Holder of this Agreement and the other Exchange Documents to which
the Holder is a party, and the consummation by the Holder of the transactions contemplated hereby and thereby will not (i) result in
a violation of the organizational documents of the Holder or (ii) conflict with, or constitute a default (or an event which with notice
or lapse of time or both would become a default) under, or give to others any rights of termination, amendment, acceleration or cancellation
of, any agreement, indenture or instrument to which the Holder is a party, or (iii) result in a violation of any law, rule, regulation,
order, judgment or decree (including federal and state securities laws) applicable to the Holder, 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 the Holder to perform its obligations hereunder.

 

5.5
Investment Risk; Sophistication. The Holder is acquiring the New Warrant hereunder in the ordinary course of its business. The
Holder has such knowledge, sophistication, and experience in business and financial matters so as to be capable of evaluation of the
merits and risks of the prospective investment in the New Warrant, and has so evaluated the merits and risk of such investment. The Holder
is an “accredited investor” as defined in Regulation D under the Securities Act.

 

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5.6
Ownership of Exchange Note. The Holder owns the Exchange Note free and clear of any Liens (other than the obligations pursuant
to this Agreement, the Transaction Documents and applicable securities laws) and has the requisite power and authority to enter into
and perform its obligations under this Agreement and each of the other Exchange Documents to which it is a party and to consummate the
Transaction.

 

5.7
Transfer or Resale. The Holder understands that except as provided Section 10 hereof: (i) the New 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 (A) subsequently registered thereunder, (B) the Holder shall have delivered to the Company (if requested by the Company) an opinion
of counsel, in a form reasonably acceptable to the Company, to the effect that such New Securities to be sold, assigned or transferred
may be sold, assigned or transferred pursuant to an exemption from such registration, or (C) the Holder provides the Company with reasonable
assurance that such New Securities can be sold, assigned or transferred pursuant to Rule 144; (ii) any sale of the New Securities made
in reliance on Rule 144 may be made only in accordance with the terms of Rule 144, and further, if Rule 144 is not applicable, any resale
of the New Securities under circumstances in which the seller (or the Person through whom the sale is made) may be deemed to be an underwriter
(as that term is defined in the Securities Act) may require compliance with some other exemption under the Securities Act or the rules
and regulations of the SEC promulgated thereunder; and (iii) neither the Company nor any other Person is under any obligation to register
the New Securities under the Securities Act or any state securities laws or to comply with the terms and conditions of any exemption
thereunder. Notwithstanding the foregoing, the New Securities may be pledged in connection with a bona fide margin account or other loan
or financing arrangement secured by the New Securities and such pledge of New Securities shall not be deemed to be a transfer, sale or
assignment of the New Securities hereunder, and the Holder effecting a pledge of New Securities shall not be required to provide the
Company with any notice thereof or otherwise make any delivery to the Company pursuant to this Agreement or any other Exchange Document,
including, without limitation, this Section 5.7.

 

6.
Closing; Conditions. Subject to the conditions set forth below, the Exchange shall take place at the offices of Kelley Drye &
Warren LLP, 101 Park Avenue, New York, NY 10178, on the Business Day immediately following such date as the Company shall have satisfied
all conditions to closing below, or at such other time and place as the Company and the Holder mutually agree (the “Closing”
and the “Closing Date”).

 

6.1.
Condition’s to Holder’s Obligations. The obligation of the Holder to consummate the Exchange is subject to the fulfillment,
to the Holder’s reasonable satisfaction, prior to or at the Closing, of each of the following conditions (unless waived by the
Holder in writing, prior to the Closing):

 

(a)
Representations and Warranties; Covenants. After giving effect to the consent and limited waiver contained in Section 3, the representations
and warranties of the Company contained in this Agreement shall be true and correct in all material respects (except for those representations
and warranties that are qualified by materiality or Material Adverse Effect, which are accurate in all respects) on the date hereof and
on and as of the Closing Date as if made on and as of such date (except for representations and warranties that speak as of a specific
date, which are accurate in all material respects (except for those representations and warranties that are qualified by materiality
or Material Adverse Effect, which are accurate in all respects) as of such specified date). After giving effect to the consent and limited
waiver contained in Section 3, the Company shall have performed, satisfied and complied in all respects with the covenants, agreements
and conditions required to be performed, satisfied or complied with by the Company at or prior to the Closing Date.

 

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(b)
Issuance of Securities. At the Closing, the Company shall issue the New Warrant to the Holder.

 

(c)
No Actions. No action, proceeding, investigation, regulation or legislation shall have been instituted, threatened or proposed
before any court, governmental agency or authority or legislative body to enjoin, restrain, prohibit or obtain substantial damages in
respect of, this Agreement or the consummation of the transactions contemplated by this Agreement.

 

(d)
Proceedings and Documents. All proceedings in connection with the transactions contemplated hereby and all documents and instruments
incident to such transactions shall be satisfactory in substance and form to the Holder, and the Holder shall have received all such
counterpart originals or certified or other copies of such documents as they may reasonably request.

 

(e)
No Event of Default. After giving effect to the Exchange, no Event of Default (as defined in the Existing Notes) or event that
with the passage of time or giving of notice would constitute an Event of Default shall have occurred and be continuing.

 

(f)
Consents. The Company shall have obtained all governmental, regulatory or third party consents and approvals (or waiver of such
consents or approvals), if any, necessary for the Exchange, including without limitation, those required by the Principal Market, if
any, and the Required Consents.

 

(g)
Listing. The Common Stock (A) shall be designated for quotation or listed (as applicable) on the Principal Market and (B) shall
not have been suspended, as of the Closing Date, by the SEC or the Principal Market from trading on the Principal Market.

 

6.2.
Condition’s to the Company’s Obligations. The obligation of the Company to consummate the Exchange is subject to the
fulfillment, to the Company’s reasonable satisfaction, prior to or at the Closing, of each of the following conditions (unless
waived by the Company in writing, prior to the Closing):

 

(a)
Representations and Warranties. The representations and warranties of the Holder contained in this Agreement shall be true and
correct in all material respects (except for those representations and warranties that are qualified by materiality or material adverse
effect, which are accurate in all respects) on the date hereof and on and as of the Closing Date as if made on and as of such date (except
for representations and warranties that speak as of a specific date, which are accurate in all material respects (except for those representations
and warranties that are qualified by materiality or material adverse effect, which are accurate in all respects) as of such specified
date).

 

    	9 

    	 

    

 

(b)
No Actions. No action, proceeding, investigation, regulation or legislation shall have been instituted, threatened or proposed
before any court, governmental agency or authority or legislative body to enjoin, restrain, prohibit, or obtain substantial damages in
respect of, this Agreement or the consummation of the transactions contemplated by this Agreement.

 

(c)
Proceedings and Documents. All proceedings in connection with the transactions contemplated hereby and all documents and instruments
incident to such transactions shall be satisfactory in substance and form to the Company and the Company shall have received all such
counterpart originals or certified or other copies of such documents as the Company may reasonably request.

 

7.
No Integration. None of the Company, its Subsidiaries, any of their affiliates, or any Person acting on their behalf shall,
directly or indirectly, make any offers or sales of any security (as defined in the Securities Act) or solicit any offers to buy any
security or take any other actions, under circumstances that would require registration of any of the New Warrant Shares under the Securities
Act or cause this offering of the New Warrant Shares to be integrated with such offering or any prior offerings by the Company for purposes
of Regulation D under the Securities Act.

 

8.
Additional New Warrant Covenants.

 

(a)
Reporting Status; Financial Information. Until the date on which the Holder shall have sold all of the New Securities (the
“Reporting Period”), the Company shall timely file all reports required to be filed with the SEC pursuant to the Securities
Act of 1934, as amended (the “1934 Act”), and the Company shall not terminate its status as an issuer required to
file reports under the 1934 Act even if the 1934 Act or the rules and regulations thereunder would no longer require or otherwise permit
such termination. The Company agrees to send the following to each holder of the New Warrant (each, an “Investor”)
during the Reporting Period: (i) unless the following are filed with the SEC through EDGAR and are available to the public through the
EDGAR system, within one (1) Business Day after the filing thereof with the SEC, a copy of its Annual Reports on Form 10-K and Quarterly
Reports on Form 10-Q, any interim reports or any consolidated balance sheets, income statements, stockholders’ equity statements
and/or cash flow statements for any period other than annual, any Current Reports on Form 8-K and any registration statements (other
than on Form S-8) or amendments filed pursuant to the Securities Act, (ii) unless the following are either filed with the SEC through
EDGAR or are otherwise widely disseminated via a recognized news release service (such as PR Newswire), on the same day as the release
thereof, facsimile copies of all press releases issued by the Company or any of its Subsidiaries and (iii) unless the following are filed
with the SEC through EDGAR, copies of any notices and other information made available or given to the stockholders of the Company generally,
contemporaneously with the making available or giving thereof to the stockholders.

 

(b)
Listing. The Company shall maintain the Common Stock’s authorization for quotation on the Principal Market. Neither the
Company nor any of its Subsidiaries shall take any action which would be reasonably expected to result in the delisting or suspension
of the Common Stock on the Principal Market. The Company shall pay all fees and expenses in connection with satisfying its obligations
under this Section 8(b).

 

    	10 

    	 

    

 

(c)
Exercise Procedures. The form of Exercise Notice (as defined in the New Warrant) included in the New Warrant sets forth the totality
of the procedures required of the Investor in order to exercise the New Warrant. No legal opinion or other information or instructions
shall be required of the Investor to exercise the New Warrant. The Company shall honor exercises of the New Warrant and shall deliver
the New Warrant Shares in accordance with the terms, conditions and time periods set forth in the New Warrant. Without limiting the preceding
sentences, no ink-original Exercise Notice shall be required, nor shall any medallion guarantee (or other type of guarantee or notarization)
of any Exercise Notice form be required in order to exercise the New Warrant.

 

(d)
Reservation of Shares. So long as any portion of the New Warrant remains outstanding, the Company shall take all action necessary
to at all times have authorized, and reserved for the purpose of issuance, no less than 100% of the sum of the maximum number of New
Warrant Shares issuable upon exercise of the New Warrant then outstanding (without regard to any limitations on the exercise of the New
Warrant set forth therein) (collectively, the “Required Reserve Amount”); provided that at no time shall the number
of shares of Common Stock reserved pursuant to this Section 8(d) be reduced other than proportionally in connection with any exercise
of the New Warrant. If at any time the number of shares of Common Stock authorized and reserved for issuance by the Company is not sufficient
to meet the Required Reserve Amount, the Company will promptly take all corporate action necessary to authorize and reserve a sufficient
number of shares, including, without limitation, calling a special meeting of stockholders to authorize additional shares to meet the
Company’s obligations pursuant to the Transaction Documents, in the case of an insufficient number of authorized shares, obtain
stockholder approval of an increase in such authorized number of shares, and voting the management shares of the Company in favor of
an increase in the authorized shares of the Company to ensure that the number of authorized shares is sufficient to meet the Required
Reserve Amount.

 

(e)
Pledge of New Securities. Notwithstanding anything to the contrary contained in this Agreement, the Company acknowledges and agrees
that the New Securities may be pledged by an Investor in connection with a bona fide margin agreement or other loan or financing arrangement
that is secured by the New Securities. The pledge of New Securities shall not be deemed to be a transfer, sale or assignment of the New
Securities hereunder, and no Investor effecting a pledge of New Securities shall be required to provide the Company with any notice thereof
or otherwise make any delivery to the Company pursuant to this Agreement or any other Exchange Document, including, without limitation,
Section 5.7 hereof; provided that an Investor and its pledgee shall be required to comply with the provisions of Section 5.7 hereof in
order to effect a sale, transfer or assignment of New Securities to such pledgee. The Company hereby agrees to execute and deliver such
documentation as a pledgee of the New Securities may reasonably request in connection with a pledge of the New Securities to such pledgee
by the Holder.

 

9.
Fees. The Company shall promptly reimburse Kelley Drye & Warren, LLP (counsel to the Holder), on demand, for all reasonable,
documented costs and expenses incurred by it in connection with preparing and delivering this Agreement (including, without limitation,
all reasonable, documented legal fees and disbursements in connection therewith, and due diligence in connection with the transactions
contemplated thereby) in an aggregate amount not to exceed $15,000.

 

    	11 

    	 

    

 

10.
Holding Period. For the purposes of Rule 144, the Company acknowledges that the holding period of the New Warrant (and
upon cashless exercise of the New Warrant, the New Warrant Shares) may be tacked onto the holding period of the Exchange Note, and the
Company agrees not to take a position contrary to this Section 10. The Company acknowledges and agrees that from and after May 9, 2022
assuming (a) the Holder is not an affiliate of the Company and (b) at such time of determination no Current Public Information Failure
exists, (i) the New Warrant shall not be required to bear any restrictive legend and shall be freely transferable by the Holder pursuant
to and in accordance with Rule 144 and (ii) to the extent any applicable New Warrant Shares are issued pursuant to a “cashless
exercise” of the New Warrant, such New Warrant Shares shall not be required to bear any restrictive legend and shall be freely
transferable by the Holder pursuant to and in accordance with Rule 144.

 

11.
Register; Transfer Agent Instructions; Legend.

 

(a)
Register. The Company shall maintain at its principal executive offices (or such other office or agency of the Company as it may
designate by notice to each Investor, a register for the New Warrant in which the Company shall record the name and address of the Person
in whose name the New Warrant has been issued (including the name and address of each transferee), and the number of New Warrant Shares
issuable upon exercise of the New Warrant held by such Person. The Company shall keep the register open and available at all times during
business hours for inspection of the Investor or its legal representatives.

 

(b)
Transfer Agent Instructions. The Company shall issue irrevocable instructions to its transfer agent (the “Transfer Agent”)
and any subsequent transfer agent in a form acceptable to the Holder (the “Irrevocable Transfer Agent Instructions”)
to issue certificates or credit shares to the applicable balance accounts at the Depository Trust Company (“DTC”),
registered in the name of the Holder or its respective nominee(s), for the New Warrant Shares in such amounts as specified from time
to time by the Holder to the Company upon the exercise of the New Warrant. The Company represents and warrants that no instruction other
than the Irrevocable Transfer Agent Instructions referred to in this Section 11(b) will be given by the Company to its Transfer Agent
with respect to the New Warrant Shares, and that the New Warrant Shares shall otherwise be freely transferable on the books and records
of the Company, as applicable, to the extent provided in this Agreement and the other Transaction Documents. If the Holder effects a
sale, assignment or transfer of the New Warrant Shares, the Company shall permit the transfer and shall promptly instruct its Transfer
Agent to issue one or more certificates or credit shares to the applicable balance accounts at DTC in such name and in such denominations
as specified by the Holder to effect such sale, transfer or assignment. The Company acknowledges that a breach by it of its obligations
hereunder will cause irreparable harm to the Holder. Accordingly, the Company acknowledges that the remedy at law for a breach of its
obligations under this Section 11(b) will be inadequate and agrees, in the event of a breach or threatened breach by the Company of the
provisions of this Section 11(b) that the Holder shall be entitled, in addition to all other available remedies, to an order and/or injunction
restraining any breach and requiring immediate issuance and transfer, without the necessity of showing economic loss and without any
bond or other security being required. The Company shall cause its counsel to issue each legal opinion referred to in the Irrevocable
Transfer Agent Instructions to the Transfer Agent as follows: (i) upon each exercise of the New Warrant (unless such issuance is covered
by a prior legal opinion previously delivered to the Transfer Agent), and (ii) on each date a registration statement with respect to
the issuance or resale of any of the New Warrant Shares is declared effective by the SEC. Any fees (with respect to the Transfer Agent,
counsel to the Company or otherwise) associated with the issuance of such opinions or the removal of any legends on any of the New Warrant
Shares shall be borne by the Company.

 

    	12 

    	 

    

 

(c)
Legends. The Holder understands that the New Warrant has been issued (or will be issued in the case of the New Warrant Shares)
pursuant to an exemption from registration or qualification under the Securities Act and applicable state securities laws, and except
as set forth below, the New Securities shall bear any legend as required by the “blue sky” laws of any state and a restrictive
legend in substantially the following form (and a stop-transfer order may be placed against transfer of such stock certificates):

 

[NEITHER
THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE EXERCISABLE
HAVE BEEN][THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN] REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, 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 OF 1933, AS AMENDED, OR (B) AN OPINION OF COUNSEL TO
THE HOLDER (IF REQUESTED BY THE COMPANY), IN A FORM REASONABLY ACCEPTABLE TO THE COMPANY, THAT REGISTRATION IS NOT REQUIRED UNDER SAID
ACT OR (II) UNLESS SOLD OR ELIGIBLE TO BE SOLD PURSUANT TO RULE 144 OR RULE 144A UNDER SAID ACT. NOTWITHSTANDING THE FOREGOING, THE SECURITIES
MAY BE PLEDGED IN CONNECTION WITH A BONA FIDE MARGIN ACCOUNT OR OTHER LOAN OR FINANCING ARRANGEMENT SECURED BY THE SECURITIES.

 

(d)
Removal of Legends. Certificates evidencing New Securities shall not be required to contain the legend set forth in Section 11(c)
above or any other legend (i) while a registration statement covering the resale of such New Securities is effective under the Securities
Act, (ii) following any sale of such New Securities pursuant to Rule 144 (assuming neither the transferor nor the transferee is an affiliate
of the Company), (iii) if such New Securities are eligible to be sold, assigned or transferred under Rule 144 (provided that the Holder
provides the Company with reasonable assurances that such New Securities are eligible for sale, assignment or transfer under Rule 144
which shall not include an opinion of Holder’s counsel), (iv) in connection with a sale, assignment or other transfer (other than
under Rule 144), provided that the Holder provides the Company with an opinion of counsel to the Holder, in a generally acceptable form,
to the effect that such sale, assignment or transfer of the New Securities may be made without registration under the applicable requirements
of the Securities Act or (v) if such legend is not required under applicable requirements of the Securities Act (including, without limitation,
controlling judicial interpretations and pronouncements issued by the SEC). If a legend is not required pursuant to the foregoing with
respect to such New Securities, the Company shall no later than two (2) Trading Days (or such earlier date as required pursuant to the
1934 Act or other applicable law, rule or regulation for the settlement of a trade initiated on the date the Holder delivers such legended
certificate representing such New Securities to the Company) following the delivery by the Holder to the Company or the transfer agent
(with notice to the Company) of a legended certificate representing such New Securities (endorsed or with stock powers attached, signatures
guaranteed, and otherwise in form necessary to affect the reissuance and/or transfer, if applicable), together with any other deliveries
from the Holder as may be required above in this Section 11(d), as directed by the Holder, either: (A) provided that the Company’s
transfer agent is participating in the DTC Fast Automated Securities Transfer Program and such New Securities are New Warrant Shares,
credit the aggregate number of shares of Common Stock to which the Holder shall be entitled to the Holder’s or its designee’s
balance account with DTC through its Deposit/Withdrawal at Custodian system or (B) if the Company’s transfer agent is not participating
in the DTC Fast Automated Securities Transfer Program, issue and deliver (via reputable overnight courier) to the Holder, a certificate
representing such New Securities that is free from all restrictive and other legends, registered in the name of the Holder or its designee
(the date by which such credit is so required to be made to the balance account of the Holder’s or the Holder’s nominee with
DTC or such certificate is required to be delivered to the Holder pursuant to the foregoing is referred to herein as the “Share
Delivery Deadline”). The Company shall be responsible for any transfer agent fees or DTC fees with respect to any issuance
of New Securities or the removal of any legends with respect to any New Securities in accordance herewith.

 

    	13 

    	 

    

 

(e)
Failure to Timely Deliver; Buy-In. If the Company fails, for any reason or for no reason, to issue and (i) if the Transfer Agent
is not participating in the DTC Fast Automated Securities Transfer Program, deliver (or cause to be delivered) to the Holder (or its
designee) by the applicable Share Delivery Deadline a certificate for the number of New Warrant Shares submitted for legend removal by
the Holder pursuant to Section 11(d) above to which the Holder is entitled and register such New Warrant Shares on the Company’s
share register or (ii) if the Transfer Agent is participating in the DTC Fast Automated Securities Transfer Program, credit the balance
account of the Holder or the Holder’s designee with DTC for such number of New Warrant Shares submitted for legend removal by the
Holder pursuant to Section 11(d) above to which the Holder is entitled (in each case, a “Delivery Failure”), and if
on or after such Trading Day the Holder purchases (in an open market transaction or otherwise) shares of Common Stock to deliver in satisfaction
of a sale by the Holder of shares of Common Stock submitted for legend removal by the Holder pursuant to Section 11(d) above that the
Holder is entitled to receive from the Company (a “Buy-In”), then the Company shall, within two (2) Trading Days after
the Holder’s request and in the Holder’s discretion, either (i) pay cash to the Holder in an amount equal to the Holder’s
total purchase price (including brokerage commissions and other out-of-pocket expenses, if any, for the shares of Common Stock so purchased)
(the “Buy-In Price”), at which point the Company’s obligation to so deliver such certificate or credit the Holder’s
balance account shall terminate and such shares shall be cancelled, or (ii) promptly honor its obligation to so deliver to the Holder
a certificate or certificates or credit the balance account of the Holder or the Holder’s designee with DTC representing such number
of shares of Common Stock that would have been so delivered if the Company timely complied with its obligations hereunder and pay cash
to the Holder in an amount equal to the excess (if any) of the Buy-In Price over the product of (A) such number of New Warrant Shares
that the Company was required to deliver to the Holder by the Share Delivery Deadline multiplied by (B) the lowest Closing Sale Price
(as defined in the Warrant”) of the Common Stock on any Trading Day during the period commencing on the date of the delivery by
the Holder to the Company of the Holder’s request under this Section 11(e) and ending on the date of such delivery and payment
under this clause (ii). Nothing shall limit the Holder’s right to pursue any other remedies available to it hereunder, at law or
in equity, including, without limitation, a decree of specific performance and/or injunctive relief with respect to the Company’s
failure to timely deliver certificates representing shares of Common Stock (or to electronically deliver such shares of Common Stock)
as required pursuant to the terms hereof. Notwithstanding anything herein to the contrary, with respect to any given Delivery Failure,
this Section 11(e) shall not apply to the Holder to the extent the Company has already paid such amounts in full to the Holder with respect
to such Delivery Failure, as applicable, pursuant to the analogous section of the New Warrant held by the Holder. Additionally, if the
Company fails for any reason to deliver to the Holder the Warrant Shares subject to an Exercise Notice (as defined in the Warrant) by
the Share Delivery Deadline, the Company shall pay to the Holder, in cash, as liquidated damages and not as a penalty, for each $1,000
of Warrant Shares subject to such exercise (based on the Weighted Average Price (as defined in the Warrant) of the Common Stock on the
date of the applicable Notice of Exercise), $10 per Trading Day (increasing to $20 per Trading Day on the fifth (5th) Trading
Day after such liquidated damages begin to accrue) for each Trading Day after such Share Delivery Deadline until such Warrant Shares
are delivered or Holder rescinds such exercise.

 

    	14 

    	 

    

 

(f)
FAST Compliance. While the New Warrant remain outstanding, the Company shall maintain a transfer agent that participates in the
DTC Fast Automated Securities Transfer Program.

 

12.
Blue Sky. The Company shall make all filings and reports relating to the Exchange required under applicable securities
or “Blue Sky” laws of the states of the United States following the date hereof, if any.

 

13.
Disclosure of Transaction.

 

(a)
On or before 9:00 a.m., New York time, on the first (1st) Business Day after the date of this Agreement, the Company shall
file a Current Report on Form 8-K describing all the material terms of the transactions contemplated by the Exchange Documents in the
form required by the Exchange Act and attaching this Agreement and the forms of the New Warrant (including all attachments, the “8-K
Filing”). From and after the filing of the 8-K Filing, the Company shall have disclosed all material, non-public information
(if any) provided to the Holder by the Company or any of its Subsidiaries or any of their respective officers, directors, employees or
agents in connection with the transactions contemplated by the Exchange Documents. In addition, effective upon the filing of the 8-K
Filing, the Company acknowledges and agrees that any and all confidentiality or similar obligations under any agreement, whether written
or oral, between the Company, any of its Subsidiaries or any of their respective officers, directors, affiliates, employees or agents,
on the one hand, and the Holder or any of its affiliates, on the other hand, relating to the transactions contemplated by the Exchange
Documents, shall terminate.

 

(b)
Except as may be required by the Securities Purchase Agreement or the New Warrant, the Company shall not, and the Company shall cause
each of its Subsidiaries and each of its and their respective officers, directors, employees and agents not to, provide the Holder with
any material, non-public information regarding the Company or any of its Subsidiaries from and after the date hereof without the express
prior written consent of the Holder (which may be granted or withheld in the Holder’s sole discretion). To the extent that the
Company delivers any material, non-public information to the Holder without the Holder’s consent, other than as required by the
Securities Purchase Agreement or the New Warrant, the Company hereby covenants and agrees that the Holder shall not have any duty of
confidentiality with respect to such material, non-public information. Subject to the foregoing, neither the Company, its Subsidiaries
nor the Holder shall issue any press releases or any other public statements with respect to the transactions contemplated hereby; provided,
however, the Company shall be entitled, without the prior approval of the Holder, to make any press release or other public disclosure
with respect to such transactions (i) in substantial conformity with the 8-K Filing and (ii) as is required by applicable law and regulations.
Notwithstanding anything contained in this Agreement to the contrary and without implication that the contrary would otherwise be true,
the Company expressly acknowledges and agrees that the Holder shall not have (unless expressly agreed to by the Holder after the date
hereof in a written definitive and binding agreement executed by the Company and the Holder), any duty of confidentiality with respect
to any material, non-public information regarding the Company or any of its Subsidiaries.

 

    	15 

    	 

    

 

14.
Termination. If the Transaction is not consummated on or prior to March 1, 2022, the Holder may terminate this Agreement
by written notice to the Company and this Agreement shall thereafter be null and void, ab initio.

 

15.
Independent Nature of Holder’s Obligations and Rights. The obligations of the Holder under this Agreement are several
and not joint with the obligations of any other holder of Existing Notes of the Company (each, an “Other Holder”),
and the Holder shall not be responsible in any way for the performance of the obligations of any Other Holder under any other agreement
by and between the Company and any Other Holder (each, an “Other Agreement”). Nothing contained herein or in any Other
Agreement, and no action taken by the Holder pursuant hereto, shall be deemed to constitute the Holder and Other Holders as a partnership,
an association, a joint venture or any other kind of entity, or create a presumption that the Holder and Other Holders are in any way
acting in concert or as a group with respect to such obligations or the transactions contemplated by this Agreement or any Other Agreement
and the Company acknowledges that, to the best of its knowledge, the Holder and the Other Holders are not acting in concert or as a group
with respect to such obligations or the transactions contemplated by this Agreement or any Other Agreement. The Company and the Holder
confirm that the Holder has independently participated in the negotiation of the transactions contemplated hereby with the advice of
its own counsel and advisors. The Holder shall be entitled to independently protect and enforce its rights, including, without limitation,
the rights arising out of this Agreement, and it shall not be necessary for any Other Holder to be joined as an additional party in any
proceeding for such purpose.

 

16.
Most Favored Nations. The Company hereby represents and warrants as of the date hereof and covenants and agrees that from
the date hereof through the date that the Existing Notes are no longer outstanding (the “MFN Termination Date”) none
of the terms offered to any Other Holder with respect to any Existing Note (including any security subsequently exchanged therefor),
including, without limitation with respect to any consent, release, amendment, settlement, or waiver relating to any exchange of any
such security (each an “Settlement Document”), is or will be more favorable to such Person (other than any reimbursement
of legal fees) than those of the Holder and this Agreement. If, and whenever during the period beginning on the date hereof and ending
on the MFN Termination Date, the Company enters into a Settlement Document, then (i) the Company shall provide notice thereof to the
Holder immediately following the occurrence thereof and (ii) the terms and conditions of this Agreement shall be, without any further
action by the Holder or the Company, automatically amended and modified in an economically and legally equivalent manner such that the
Holder shall receive the benefit of the more favorable terms and/or conditions (as the case may be) set forth in such Settlement Document,
provided that upon written notice to the Company at any time the Holder may elect not to accept the benefit of any such amended or modified
term or condition, in which event the term or condition contained in this Agreement shall apply to the Holder as it was in effect immediately
prior to such amendment or modification as if such amendment or modification never occurred with respect to the Holder. The provisions
of this Section 17 shall apply similarly and equally to each Settlement Document entered into on or prior to the MFN Termination Date.

 

17.
Miscellaneous Provisions. Section 9 of the Securities Purchase Agreement (as amended hereby) is hereby incorporated by
reference herein, mutatis mutandis.

 

[The
remainder of the page is intentionally left blank]

 

    	16 

    	 

    

 

IN
WITNESS WHEREOF, the Holder and the Company have executed this Agreement as of the date first set forth on the first page of this
Agreement.

 

	 	COMPANY:
	 	 	 
	 	GAUCHO
    GROUP HOLDINGS, INC.
	 	 	 
	 	By:	 
	 	Name:	Scott
    L. Mathis
	 	Title:	President
    & CEO

 

    	 

     

    

 

IN
WITNESS WHEREOF, the Holder and the Company have executed this Agreement as of the date first set forth on the first page of this
Agreement.

 

	 	 	HOLDER:
	 	 	 	 
	Principal
    Amount of Existing Note of Holder:	 	[Name]
	 	 	 	 
	$                           	 	By:	       
	 	 	Name:	 
	 	 	Title:	 
	Aggregate
    Number of New Warrant Shares issuable upon exercise of the New Warrant (without regard to any limitations on exercise set forth therein):	 	 	 
	 	 	 	 
	                             	 	 	 
	 	 	 	 
	Existing
    Amortization Amount:	 	 	 
	 	 	 	 
	$                           	 	 	 
	 	 	 	 
	New
    Amortization Amount after giving effect to waivers herein:	 	 	 
	 	 	 	 
	$                           	 	 	 

 

    	 

     

    

 

Schedule
3(c)

 

	1.	Section
    4(c) of the Securities Purchase Agreement—certain SEC filings were not filed on a timely basis.
	 	 
	2.	Section
    4(d) of the Securities Purchase Agreement—see Section 3(b) above.
	 	 
	3.	Section
    4(h) of the Securities Purchase Agreement—non-timely pledge of additional securities of Scott L. Mathis.
	 	 
	4.	Section
    4(k) of the Securities Purchase Agreement—additional issuances of securities.
	 	 
	5.	Section
    4(n) of the Securities Purchase Agreement—issuance of variable securities.
	 	 
	6.	Section
    4(o) of the Securities Purchase Agreement—participation right of Holders upon additional issuances of securities.
	 	 
	7.	Section
    4(p) of the Securities Purchase Agreement—additional issuance of securities dilutive.
	 	 
	8.	Section
    4(z) of the Securities Purchase Agreement—issuance of additional securities and integration.
	 	 
	9.	Section
    3(e) of the Existing Notes—right of Alternate Conversion upon Event of Default (no available registration statement effective
    for more than 10 days).
	 	 
	10.	Section
    4(b) of the Existing Notes—redemption right upon Event of Default.
	 	 
	11.	Section
    7 of the Existing Notes—issuance of additional securities and right of adjustment of Conversion Price.
	 	 
	12.	Section
    10 of the Existing Notes—issuance of additional securities subject to optional redemption.
	 	 
	13.	Section
    15(n) of the Existing Notes—issuance of additional securities.Exhibit
4.1

 

NEITHER
THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS CERTIFICATE NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE CONVERTIBLE
HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED
FOR SALE, SOLD, TRANSFERRED OR ASSIGNED IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR THE SECURITIES UNDER THE SECURITIES
ACT OF 1933, AS AMENDED, OR (B) AN OPINION OF COUNSEL (WHICH COUNSEL SHALL BE SELECTED BY THE HOLDER), IN A GENERALLY ACCEPTABLE FORM,
THAT REGISTRATION IS NOT REQUIRED UNDER SAID ACT. NOTWITHSTANDING THE FOREGOING, THE SECURITIES MAY BE PLEDGED IN CONNECTION WITH A BONA
FIDE MARGIN ACCOUNT OR OTHER LOAN OR FINANCING ARRANGEMENT SECURED BY THE SECURITIES.

 

Principal
Amount: $49,250.00 Issue Date: September 12, 2022 Purchase Price: $49,250.00

 

CONVERTIBLE
PROMISSORY NOTE

 

FOR
VALUE RECEIVED, RAINMAKER WORLDWIDE INC., a Nevada corporation (hereinafter called the “Borrower”), hereby promises
to pay to the order of _____________________________, a Virginia limited liability company, or registered assigns (the “Holder”)
the sum of $49,250.00 together with any interest as set forth herein, on September 12, 2023 (the “Maturity Date”), and to
pay interest on the unpaid principal balance hereof at the rate of ten percent (10%)(the “Interest Rate”) per annum from
the date hereof (the “Issue Date”) until the same becomes due and payable, whether at maturity or upon acceleration or by
prepayment or otherwise. This Note may not be prepaid in whole or in part except as otherwise explicitly set forth herein. Any amount
of principal or interest on this Note which is not paid when due shall bear interest at the rate of twenty two percent (22%) per annum
from the due date thereof until the same is paid (“Default Interest”). Interest shall be computed on the basis of a 365 day
year and the actual number of days elapsed. Interest shall commence accruing on the Issue Date but shall not be payable until the Note
becomes payable (whether at Maturity Date or upon acceleration or by prepayment). All payments due hereunder (to the extent not converted
into common stock, $0.001 par value per share (the “Common Stock”) in accordance with the terms hereof) shall be made in
lawful money of the United States of America. All payments shall be made at such address as the Holder shall hereafter give to the Borrower
by written notice made in accordance with the provisions of this Note. Each capitalized term used herein, and not otherwise defined,
shall have the meaning ascribed thereto in that certain Securities Purchase Agreement dated the date hereof, pursuant to which this Note
was originally issued (the “Purchase Agreement”).

 

This
Note is free from all taxes, liens, claims and encumbrances with respect to the issue thereof and shall not be subject to preemptive
rights or other similar rights of shareholders of the Borrower and will not impose personal liability upon the holder thereof.

 

The
following terms shall apply to this Note:

 

	Principal
    Amount: $49,250.00	Issue
    Date: September 12, 2022
	Purchase
    Price: $49,250.00	 

 

CONVERTIBLE
PROMISSORY NOTE

 

FOR
VALUE RECEIVED, RAINMAKER WORLDWIDE INC., a Nevada corporation (hereinafter called the “Borrower”), hereby promises
to pay to the order of ______________________________, a Virginia limited liability company, or registered assigns (the “Holder”)
the sum of $49,250.00 together with any interest as set forth herein, on September 12, 2023 (the “Maturity Date”), and to
pay interest on the unpaid principal balance hereof at the rate of ten percent (10%)(the “Interest Rate”) per annum from
the date hereof (the “Issue Date”) until the same becomes due and payable, whether at maturity or upon acceleration or by
prepayment or otherwise. This Note may not be prepaid in whole or in part except as otherwise explicitly set forth herein. Any amount
of principal or interest on this Note which is not paid when due shall bear interest at the rate of twenty two percent (22%) per annum
from the due date thereof until the same is paid (“Default Interest”). Interest shall be computed on the basis of a 365 day
year and the actual number of days elapsed. Interest shall commence accruing on the Issue Date but shall not be payable until the Note
becomes payable (whether at Maturity Date or upon acceleration or by prepayment). All payments due hereunder (to the extent not converted
into common stock, $0.001 par value per share (the “Common Stock”) in accordance with the terms hereof) shall be made in
lawful money of the United States of America. All payments shall be made at such address as the Holder shall hereafter give to the Borrower
by written notice made in accordance with the provisions of this Note. Each capitalized term used herein, and not otherwise defined,
shall have the meaning ascribed thereto in that certain Securities Purchase Agreement dated the date hereof, pursuant to which this Note
was originally issued (the “Purchase Agreement”).

 

This
Note is free from all taxes, liens, claims and encumbrances with respect to the issue thereof and shall not be subject to preemptive
rights or other similar rights of shareholders of the Borrower and will not impose personal liability upon the holder thereof.

 

The
following terms shall apply to this Note:

 

    	 

     

    

 

ARTICLE
I. CONVERSION RIGHTS

 

1.1
 Conversion Right. The Holder shall have the right from time to time, and at any time during the period beginning on the date which
is one hundred eighty (180) days following the date of this Note and ending on the later of: (i) the Maturity Date and (ii) the date
of payment of the Default Amount (as defined in Article III)(the “Conversion Period”), each in respect of the remaining outstanding
amount of this Note to convert all or any part of the outstanding and unpaid amount of this Note into fully paid and non-assessable shares
of Common Stock, as such Common Stock exists on the Issue Date, or any shares of capital stock or other securities of the Borrower into
which such Common Stock shall hereafter be changed or reclassified at the conversion price (the “Conversion Price”) determined
as provided herein (a “Conversion”); provided, however, that in no event shall the Holder be entitled to convert
any portion of this Note in excess of that portion of this Note upon conversion of which the sum of (1) the number of shares of Common
Stock beneficially owned by the Holder and its affiliates (other than shares of Common Stock which may be deemed beneficially owned through
the ownership of the unconverted portion of the Notes or the unexercised or unconverted portion of any other security of the Borrower
subject to a limitation on conversion or exercise analogous to the limitations contained herein) and (2) the number of shares of Common
Stock issuable upon the conversion of the portion of this Note with respect to which the determination of this proviso is being made,
would result in beneficial ownership by the Holder and its affiliates of more than 4.99% of the outstanding shares of Common Stock. For
purposes of the proviso to the immediately preceding sentence, beneficial ownership shall be determined in accordance with Section 13(d)
of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and Regulations 13D-G thereunder, except as otherwise
provided in clause (1) of such proviso. The beneficial ownership limitations on conversion as set forth in the section may NOT be
waived by the Holder. The number of shares of Common Stock to be issued upon each conversion of this Note shall be determined by
dividing the Conversion Amount (as defined below) by the applicable Conversion Price then in effect on the date specified in the notice
of conversion, in the form attached hereto as Exhibit A (the “Notice of Conversion”), delivered to the Borrower by the Holder
in accordance with Section 1.4 below; provided that the Notice of Conversion is submitted by facsimile or e-mail (or by other means resulting
in, or reasonably expected to result in, notice) to the Borrower before 6:00 p.m., New York, New York time on such conversion date (the
“Conversion Date”); however, if the Notice of Conversion is sent after 6:00pm, New York, New York time the Conversion Date
shall be the next business day. The term “Conversion Amount” means, with respect to any conversion of this Note, the sum
of (1) the principal amount of this Note to be converted in such conversion plus (2) at the Holder’s option, accrued and
unpaid interest, if any, on such principal amount at the interest rates provided in this Note to the Conversion Date, plus (3)
at the Holder’s option, Default Interest, if any, on the amounts referred to in the immediately preceding clauses (1) and/or (2)
plus (4) at the Holder’s option, any amounts owed to the Holder pursuant to Sections 1.4 hereof.

 

1.2
Conversion Price. The Conversion Price shall equal the Variable Conversion Price (as defined herein)(subject to equitable adjustments
for stock splits, stock dividends or rights offerings by the Borrower relating to the Borrower’s securities or the securities of
any subsidiary of the Borrower, combinations, recapitalization, reclassifications, extraordinary distributions and similar events). The
“Variable Conversion Price” shall mean 65% multiplied by the Market Price (as defined herein) (representing a discount rate
of 35%). “Market Price” means the lowest Trading Price (as defined below) for the Common Stock during the ten (10) Trading
Day period ending on the latest complete Trading Day prior to the Conversion Date. “Trading Price” means, for any security
as of any date, the closing bid price on the OTCQB, OTCQX, Pink Sheets electronic quotation system or applicable trading market (the
“OTC”) as reported by a reliable reporting service (“Reporting Service”) designated by the Holder (i.e. Bloomberg)
or, if the OTC is not the principal trading market for such security, the closing bid price of such security on the principal securities
exchange or trading market where such security is listed or traded or, if no closing bid price of such security is available in any of
the foregoing manners, the average of the closing bid prices of any market makers for such security that are listed in the “pink
sheets”. If the Trading Price cannot be calculated for such security on such date in the manner provided above, the Trading Price
shall be the fair market value as mutually determined by the Borrower and the holders of a majority in interest of the Notes being converted
for which the calculation of the Trading Price is required in order to determine the Conversion Price of such Notes. “Trading Day”
shall mean any day on which the Common Stock is tradable for any period on the OTC, or on the principal securities exchange or other
securities market on which the Common Stock is then being traded.

 

    	 

     

    

 

1.3
Authorized Shares. The Borrower covenants that during the period the conversion right exists, the Borrower will reserve from its
authorized and unissued Common Stock a sufficient number of shares, free from preemptive rights, to provide for the issuance of Common
Stock upon the full conversion of this Note issued pursuant to the Purchase Agreement. The Borrower is required at all times to have
authorized and reserved five times the number of shares that would be issuable upon full conversion of the Note (assuming that the 4.99%
limitation set forth in Section 1.1 is not in effect)(based on the respective Conversion Price of the Note (as defined in Section 1.2)
in effect from time to time, initially 42,094,017 shares)(the “Reserved Amount”). The Reserved Amount shall be increased
(or decreased with the written consent of the Holder) from time to time in accordance with the Borrower’s obligations hereunder.
The Borrower represents that upon issuance, such shares will be duly and validly issued, fully paid and non-assessable. In addition,
if the Borrower shall issue any securities or make any change to its capital structure which would change the number of shares of Common
Stock into which the Notes shall be convertible at the then current Conversion Price, the Borrower shall at the same time make proper
provision so that thereafter there shall be a sufficient number of shares of Common Stock authorized and reserved, free from preemptive
rights, for conversion of the outstanding Note. The Borrower (i) acknowledges that it has irrevocably instructed its transfer agent to
issue certificates for the Common Stock issuable upon conversion of this Note, and (ii) agrees that its issuance of this Note shall constitute
full authority to its officers and agents who are charged with the duty of executing stock certificates to execute and issue the necessary
certificates for shares of Common Stock in accordance with the terms and conditions of this Note.

 

If,
at any time the Borrower does not maintain the Reserved Amount it will be considered an Event of Default under Section 3.2 of the Note.

 

1.4
Method of Conversion.

 

(a)
Mechanics of Conversion. As set forth in Section 1.1 hereof, from time to time, and at any time during the period beginning on
the date which is one hundred eighty (180) days following the date of this Note and ending on the later of: (i) the Maturity Date and
(ii) the date of payment of the Default Amount, this Note may be converted by the Holder in whole or in part at any time from time to
time after the Issue Date, by (A) submitting to the Borrower a Notice of Conversion (by facsimile, e-mail or other reasonable means of
communication dispatched on the Conversion Date prior to 6:00 p.m., New York, New York time) and (B) subject to Section 1.4(b), surrendering
this Note at the principal office of the Borrower (upon payment in full of any amounts owed hereunder).

 

(b)
Surrender of Note Upon Conversion. Notwithstanding anything to the contrary set forth herein, upon conversion of this Note in
accordance with the terms hereof, the Holder shall not be required to physically surrender this Note to the Borrower unless the entire
unpaid principal amount of this Note is so converted. The Holder and the Borrower shall maintain records showing the principal amount
so converted and the dates of such conversions or shall use such other method, reasonably satisfactory to the Holder and the Borrower,
so as not to require physical surrender of this Note upon each such conversion.

 

(c)
Delivery of Common Stock Upon Conversion. Upon receipt by the Borrower from the Holder of a facsimile transmission or e-mail (or
other reasonable means of communication) of a Notice of Conversion meeting the requirements for conversion as provided in this Section
1.4, the Borrower shall issue and deliver or cause to be issued and delivered to or upon the order of the Holder certificates for the
Common Stock issuable upon such conversion within three (3) business days after such receipt (the “Deadline”) (and, solely
in the case of conversion of the entire unpaid principal amount hereof, surrender of this Note) in accordance with the terms hereof and
the Purchase Agreement. Upon receipt by the Borrower of a Notice of Conversion, the Holder shall be deemed to be the holder of record
of the Common Stock issuable upon such conversion, the outstanding principal amount and the amount of accrued and unpaid interest on
this Note shall be reduced to reflect such conversion, and, unless the Borrower defaults on its obligations hereunder, all rights with
respect to the portion of this Note being so converted shall forthwith terminate except the right to receive the Common Stock or other
securities, cash or other assets, as herein provided, on such conversion. If the Holder shall have given a Notice of Conversion as provided
herein, the Borrower’s obligation to issue and deliver the certificates for Common Stock shall be absolute and unconditional, irrespective
of the absence of any action by the Holder to enforce the same, any waiver or consent with respect to any provision thereof, the recovery
of any judgment against any person or any action to enforce the same, any failure or delay in the enforcement of any other obligation
of the Borrower to the holder of record, or any setoff, counterclaim, recoupment, limitation or termination, or any breach or alleged
breach by the Holder of any obligation to the Borrower, and irrespective of any other circumstance which might otherwise limit such obligation
of the Borrower to the Holder in connection with such conversion.

 

(d)
Delivery of Common Stock by Electronic Transfer. In lieu of delivering physical certificates representing the Common Stock issuable
upon conversion, provided the Borrower is participating in the Depository Trust Company (“DTC”) Fast Automated Securities
Transfer (“FAST”) program, upon request of the Holder and its compliance with the provisions set forth herein, the Borrower
shall use its best efforts to cause its transfer agent to electronically transmit the Common Stock issuable upon conversion to the Holder
by crediting the account of Holder’s Prime Broker with DTC through its Deposit Withdrawal Agent Commission (“DWAC”)
system.

 

    	 

     

    

 

(e)
Failure to Deliver Common Stock Prior to Deadline. Without in any way limiting the Holder’s right to pursue other remedies,
including actual damages and/or equitable relief, the parties agree that if delivery of the Common Stock issuable upon conversion of
this Note is not delivered by the Deadline due to the intentional, willful and purposeful action and/or inaction of the Borrower, the
Borrower shall pay to the Holder $2,000 per day in cash, for each day beyond the Deadline that the Borrower fails to deliver such Common
Stock (the “Fail to Deliver Fee”); provided; however that the Fail to Deliver Fee shall not be due if the failure is a result
of a third party (i.e., transfer agent; and not the result of any failure to pay such transfer agent) despite the best efforts of the
Borrower to effect delivery of such Common Stock. Such cash amount shall be paid to Holder by the fifth day of the month following the
month in which it has accrued or, at the option of the Holder (by written notice to the Borrower by the first day of the month following
the month in which it has accrued), shall be added to the principal amount of this Note, in which event interest shall accrue thereon
in accordance with the terms of this Note and such additional principal amount shall be convertible into Common Stock in accordance with
the terms of this Note. The Borrower agrees that the right to convert is a valuable right to the Holder. The damages resulting from a
failure, attempt to frustrate, interference with such conversion right are difficult if not impossible to qualify. Accordingly, the parties
acknowledge that the liquidated damages provision contained in this Section 1.4(e) are justified.

 

1.5
 Concerning the Shares. The shares of Common Stock issuable upon conversion of this Note may not be sold or transferred unless:
(i) such shares are sold pursuant to an effective registration statement under the Act or (ii) the Borrower or its transfer agent shall
have been furnished with an opinion of counsel (which opinion shall be in form, substance and scope customary for opinions of counsel
in comparable transactions) to the effect that the shares to be sold or transferred may be sold or transferred pursuant to an exemption
from such registration (such as Rule 144 or a successor rule) (“Rule 144”); or (iii) such shares are transferred to an “affiliate”
(as defined in Rule 144) of the Borrower who agrees to sell or otherwise transfer the shares only in accordance with this Section 1.5
and who is an Accredited Investor (as defined in the Purchase Agreement).

 

Any
restrictive legend on certificates representing shares of Common Stock issuable upon conversion of this Note shall be removed and the
Borrower shall issue to the Holder a new certificate therefore free of any transfer legend if the Borrower or its transfer agent shall
have received an opinion of counsel from Holder’s counsel, in form, substance and scope customary for opinions of counsel in comparable
transactions, to the effect that (i) a public sale or transfer of such Common Stock may be made without registration under the Act, which
opinion shall be accepted by the Company so that the sale or transfer is effected; or (ii) in the case of the Common Stock issuable upon
conversion of this Note, such security is registered for sale by the Holder under an effective registration statement filed under the
Act; or otherwise may be sold pursuant to an exemption from registration. In the event that the Company does not reasonably accept the
opinion of counsel provided by the Holder with respect to the transfer of Securities pursuant to an exemption from registration (such
as Rule 144), at the Deadline, it will be considered an Event of Default pursuant to Section 3.2 of the Note.

 

1.6
Effect of Certain Events.

 

(a)
Effect of Merger, Consolidation, Etc. At the option of the Holder, the sale, conveyance or disposition of all or substantially
all of the assets of the Borrower, the effectuation by the Borrower of a transaction or series of related transactions in which more
than 50% of the voting power of the Borrower is disposed of, or the consolidation, merger or other business combination of the Borrower
with or into any other Person (as defined below) or Persons when the Borrower is not the survivor shall be deemed to be an Event of Default
(as defined in Article III) pursuant to which the Borrower shall be required to pay to the Holder upon the consummation of and as a condition
to such transaction an amount equal to the Default Amount (as defined in Article III). “Person” shall mean any individual,
corporation, limited liability company, partnership, association, trust or other entity or organization.

 

(b)
Adjustment Due to Merger, Consolidation, Etc. If, at any time when this Note is issued and outstanding and prior to conversion
of all of the Note, there shall be any merger, consolidation, exchange of shares, recapitalization, reorganization, or other similar
event, as a result of which shares of Common Stock of the Borrower shall be changed into the same or a different number of shares of
another class or classes of stock or securities of the Borrower or another entity, or in case of any sale or conveyance of all or substantially
all of the assets of the Borrower other than in connection with a plan of complete liquidation of the Borrower, then the Holder of this
Note shall thereafter have the right to receive upon conversion of this Note, upon the basis and upon the terms and conditions specified
herein and in lieu of the shares of Common Stock immediately theretofore issuable upon conversion, such stock, securities or assets which
the Holder would have been entitled to receive in such transaction had this Note been converted in full immediately prior to such transaction
(without regard to any limitations on conversion set forth herein), and in any such case appropriate provisions shall be made with respect
to the rights and interests of the Holder of this Note to the end that the provisions hereof (including, without limitation, provisions
for adjustment of the Conversion Price and of the number of shares issuable upon conversion of the Note) shall thereafter be applicable,
as nearly as may be practicable in relation to any securities or assets thereafter deliverable upon the conversion hereof. The Borrower
shall not affect any transaction described in this Section 1.6(b) unless (a) it first gives, to the extent practicable, ten (10) days
prior written notice (but in any event at least five (5) days prior written notice) of the record date of the special meeting of shareholders
to approve, or if there is no such record date, the consummation of, such merger, consolidation, exchange of shares, recapitalization,
reorganization or other similar event or sale of assets (during which time the Holder shall be entitled to convert this Note) and (b)
the resulting successor or acquiring entity (if not the Borrower) assumes by written instrument the obligations of this Note. The above
provisions shall similarly apply to successive consolidations, mergers, sales, transfers or share exchanges.

 

    	 

     

    

 

(c)
Adjustment Due to Distribution. If the Borrower shall declare or make any distribution of its assets (or rights to acquire its
assets) to holders of Common Stock as a dividend, stock repurchase, by way of return of capital or otherwise (including any dividend
or distribution to the Borrower’s shareholders in cash or shares (or rights to acquire shares) of capital stock of a subsidiary
(i.e., a spin-off)) (a “Distribution”), then the Holder of this Note shall be entitled, upon any conversion of this Note
after the date of record for determining shareholders entitled to such Distribution, to receive the amount of such assets which would
have been payable to the Holder with respect to the shares of Common Stock issuable upon such conversion had such Holder been the holder
of such shares of Common Stock on the record date for the determination of shareholders entitled to such Distribution.

 

1.7
Prepayment. Notwithstanding anything to the contrary contained in this Note, at any time during the periods set forth on the table
immediately following this paragraph (the “Prepayment Periods”) or as otherwise agreed to between the Borrower and the Holder,
the Borrower shall have the right, exercisable on not more than three (3) Trading Days prior written notice to the Holder of the Note
to prepay the outstanding Note (principal and accrued interest), in full, in accordance with this Section 1.7. Any notice of prepayment
hereunder (an “Optional Prepayment Notice”) shall be delivered to the Holder of the Note at its registered addresses and
shall state: (1) that the Borrower is exercising its right to prepay the Note, and (2) the date of prepayment which shall be not more
than three

(3)
Trading Days from the date of the Optional Prepayment Notice. On the date fixed for prepayment (the “Optional Prepayment Date”),
the Borrower shall make payment of the Optional Prepayment Amount (as defined below) to Holder, or upon the direction of the Holder as
specified by the Holder in a writing to the Borrower (which shall direction to be sent to Borrower by the Holder at least one (1) business
day prior to the Optional Prepayment Date). If the Borrower exercises its right to prepay the Note, the Borrower shall make payment to
the Holder of an amount in cash equal to the percentage (“Prepayment Percentage”) as set forth in the table immediately following
this paragraph opposite the applicable Prepayment Period, multiplied by the sum of: (w) the then outstanding principal amount of this
Note plus (x) accrued and unpaid interest on the unpaid principal amount of this Note to the Optional Prepayment Date plus
(y) Default Interest, if any, on the amounts referred to in clauses (w) and (x) plus (z) any amounts owed to the Holder pursuant
to Section 1.4 hereof (the “Optional Prepayment Amount”).

 

	Prepayment
    Period	 	Prepayment
    Percentage
	1.
    The period beginning on the Issue Date and ending on

    the
    date which is sixty (60) days following the Issue Date.
	 	115%
	2.
    The period beginning on the date which is sixty-one

    (61)
    days from the Issue Date and ending one hundred twenty

    (120)
    days following the Issue Date.
	 	120%
	3. The period beginning on the date which iss one hundred 
 twenty-one (121) days from the Issue Date and ending one

                                                                                hundred eighty (180) days following the Issue Date.
	 	125%

 

    	 

     

    

 

After
the expiration of the Prepayment Periods set forth above, the Borrower may submit an Optional Prepayment Notice to the Holder. Upon receipt
by the Holder of the Optional Prepayment Notice post Prepayment Periods, the prepayment shall be subject to the Holder’s and the
Borrower’s agreement with respect to the applicable Prepayment Percentage.

 

Notwithstanding
anything contained herein to the contrary, the Holder’s conversion rights herein shall not be affected in any way until the Note
is fully paid (funds received by the Holder) pursuant to an Optional Prepayment Notice.

 

ARTICLE
II. CERTAIN COVENANTS

 

2.1
Sale of Assets. So long as the Borrower shall have any obligation under this Note, the Borrower shall not, without the Holder’s
written consent, sell, lease or otherwise dispose of any significant portion of its assets outside the ordinary course of business. Any
consent to the disposition of any assets may be conditioned on a specified use of the proceeds of disposition.

 

ARTICLE
III. EVENTS OF DEFAULT

 

If
any of the following events of default (each, an “Event of Default”) shall occur:

 

3.1
Failure to Pay Principal and Interest. The Borrower fails to pay the principal hereof or interest thereon when due on this Note,
whether at maturity or upon acceleration and such breach continues for a period of five (5) days after written notice from the Holder.

 

3.2
Conversion and the Shares. The Borrower fails to issue shares of Common Stock to the Holder (or announces or threatens in writing
that it will not honor its obligation to do so) upon exercise by the Holder of the conversion rights of the Holder in accordance with
the terms of this Note, fails to transfer or cause its transfer agent to transfer (issue) (electronically or in certificated form) any
certificate for shares of Common Stock issued to the Holder upon conversion of or otherwise pursuant to this Note as and when required
by this Note, the Borrower directs its transfer agent not to transfer or delays, impairs, and/or hinders its transfer agent in transferring
(or issuing) (electronically or in certificated form) any certificate for shares of Common Stock to be issued to the Holder upon conversion
of or otherwise pursuant to this Note as and when required by this Note, or fails to remove (or directs its transfer agent not to remove
or impairs, delays, and/or hinders its transfer agent from removing) any restrictive legend (or to withdraw any stop transfer instructions
in respect thereof) on any certificate for any shares of Common Stock issued to the Holder upon conversion of or otherwise pursuant to
this Note as and when required by this Note (or makes any written announcement, statement or threat that it does not intend to honor
the obligations described in this paragraph) and any such failure shall continue uncured (or any written announcement, statement or threat
not to honor its obligations shall not be rescinded in writing) for three (3) business days after the Holder shall have delivered a Notice
of Conversion. It is an obligation of the Borrower to remain current in its obligations to its transfer agent. It shall be an event of
default of this Note, if a conversion of this Note is delayed, hindered or frustrated due to a balance owed by the Borrower to its transfer
agent. If at the option of the Holder, the Holder advances any funds to the Borrower’s transfer agent in order to process a conversion,
such advanced funds shall be paid by the Borrower to the Holder within forty-eight (48) hours of a demand from the Holder.

 

3.3
Breach of Covenants. The Borrower breaches any material covenant or other material term or condition contained in this Note and
any collateral documents including but not limited to the Purchase Agreement and such breach continues for a period of twenty (20) days
after written notice thereof to the Borrower from the Holder.

 

3.4
Breach of Representations and Warranties. Any representation or warranty of the Borrower made herein or in any agreement, statement
or certificate given in writing pursuant hereto or in connection herewith (including, without limitation, the Purchase Agreement), shall
be false or misleading in any material respect when made and the breach of which has (or with the passage of time will have) a material
adverse effect on the rights of the Holder with respect to this Note or the Purchase Agreement.

 

3.5
Receiver or Trustee. The Borrower or any subsidiary of the Borrower shall make an assignment for the benefit of creditors or apply
for or consent to the appointment of a receiver or trustee for it or for a substantial part of its property or business, or such a receiver
or trustee shall otherwise be appointed.

 

    	 

     

    

 

3.6
Bankruptcy. Bankruptcy, insolvency, reorganization or liquidation proceedings or other proceedings, voluntary or involuntary,
for relief under any bankruptcy law or any law for the relief of debtors shall be instituted by or against the Borrower or any subsidiary
of the Borrower.

 

3.7
Delisting of Common Stock. The Borrower shall fail to maintain the listing of the Common Stock on at least one of the OTC (which
specifically includes the quotation platforms maintained by the OTC Markets Group) or an equivalent replacement exchange, the Nasdaq
National Market, the Nasdaq SmallCap Market, the New York Stock Exchange, or the American Stock Exchange.

 

3.8
Failure to Comply with the Exchange Act. The Borrower shall fail to comply with the reporting requirements of the Exchange Act;
and/or the Borrower shall cease to be subject to the reporting requirements of the Exchange Act (the filing of a Form 15 with the SEC
is an immediate Event of Default). During the period beginning on the date of this Note and ending ten (10) days prior to the Conversion
Period, the Borrower shall have ten (10) days to cure a breach for failure to comply with the reporting requirements of the Exchange
Act.

 

3.9
Liquidation. Any dissolution, liquidation, or winding up of Borrower or any substantial portion of its business.

 

3.10
Cessation of Operations. Any cessation of operations by Borrower or Borrower admits it is otherwise generally unable to pay its
debts as such debts become due, provided, however, that any disclosure of the Borrower’s ability to continue as a “going
concern” shall not be an admission that the Borrower cannot pay its debts as they become due.

 

3.11
Financial Statement Restatement. The restatement of any financial statements filed by the Borrower with the SEC at any time after
180 days after the Issuance Date for any date or period until this Note is no longer outstanding, if the result of such restatement would,
by comparison to the un-restated financial statement, have constituted a material adverse effect on the rights of the Holder with respect
to this Note or the Purchase Agreement.

3.12
 Replacement of Transfer Agent. In the event that the Borrower proposes to replace its transfer agent, the Borrower fails to provide,
prior to the effective date of such replacement, a fully executed Irrevocable Transfer Agent Instructions in a form as initially delivered
pursuant to the Purchase Agreement (including but not limited to the provision to irrevocably reserve shares of Common Stock in the Reserved
Amount) signed by the successor transfer agent to Borrower and the Borrower.

 

3.13
Cross-Default. Notwithstanding anything to the contrary contained in this Note or the other related or companion documents, a
breach or default by the Borrower of any covenant or other term or condition contained in any of the Other Agreements, after the passage
of all applicable notice and cure or grace periods, shall, at the option of the Holder, be considered a default under this Note and the
Other Agreements, in which event the Holder shall be entitled (but in no event required) to apply all rights and remedies of the Holder
under the terms of this Note and the Other Agreements by reason of a default under said Other Agreement or hereunder. “Other Agreements”
means, collectively, all agreements and instruments between, among or by: (1) the Borrower, and, or for the benefit of, (2) the Holder
and any affiliate of the Holder, including, without limitation, promissory notes; provided, however, the term “Other Agreements”
shall not include the related or companion documents to this Note. Each of the loan transactions will be cross-defaulted with each other
loan transaction and with all other existing and future debt of Borrower to the Holder.

 

Upon
the occurrence and during the continuation of any Event of Default specified in Section 3.1 (solely with respect to failure to pay the
principal hereof or interest thereon when due at the Maturity Date), the Note shall become immediately due and payable and the Borrower
shall pay to the Holder, in full satisfaction of its obligations hereunder, an amount equal to the Default Amount (as defined herein).
UPON THE OCCURRENCE AND DURING THE CONTINUATION OF ANY EVENT OF DEFAULT SPECIFIED IN SECTION 3.2, THE NOTE SHALL BECOME IMMEDIATELY DUE
AND PAYABLE AND THE BORROWER SHALL PAY TO THE HOLDER, IN FULL SATISFACTION OF ITS OBLIGATIONS HEREUNDER, AN AMOUNT EQUAL TO: (Y) THE
DEFAULT AMOUNT (AS DEFINED HEREIN); MULTIPLIED BY (Z) TWO (2). Upon the occurrence and during the continuation of any Event of Default
specified in Sections 3.1 (solely with respect to failure to pay the principal hereof or interest thereon when due on this Note upon
a Trading Market Prepayment Event pursuant to Section 1.7 or upon acceleration), 3.3, 3.4, 3.7, 3.8, 3.10, 3.11, 3.12, 3.13, and/or 3.14
exercisable through the delivery of written notice to the Borrower by such Holders (the “Default Notice”), and upon the occurrence
of an Event of Default specified the remaining sections of Articles III (other than failure to pay the principal hereof or interest thereon
at the Maturity Date specified in Section 3,1 hereof), the Note shall become immediately due and payable and the Borrower shall pay to
the Holder, in full satisfaction of its obligations hereunder, an amount equal to 150% times the sum of (w) the then outstanding
principal amount of this Note plus (x) accrued and unpaid interest on the unpaid principal amount of this Note to the date of
payment (the “Mandatory Prepayment Date”) plus (y) Default Interest, if any, on the amounts referred to in clauses
(w) and/or (x) plus (z) any amounts owed to the Holder pursuant to Sections 1.3 and 1.4(g) hereof (the then outstanding principal
amount of this Note to the date of payment plus the amounts referred to in clauses (x), (y) and (z) shall collectively be known
as the “Default Amount”) and all other amounts payable hereunder shall immediately become due and payable, all without demand,
presentment or notice, all of which hereby are expressly waived, together with all costs, including, without limitation, legal fees and
expenses, of collection, and the Holder shall be entitled to exercise all other rights and remedies available at law or in equity.

 

    	 

     

    

 

If
the Borrower fails to pay the Default Amount within five (5) business days of written notice that such amount is due and payable, then
the Holder shall have the right at any time, so long as the Borrower remains in default (and so long and to the extent that there are
sufficient authorized shares), to require the Borrower, upon written notice, to immediately issue, in lieu of the Default Amount, the
number of shares of Common Stock of the Borrower equal to the Default Amount divided by the Conversion Price then in effect.

 

ARTICLE
IV. MISCELLANEOUS

 

4.1
Failure or Indulgence Not Waiver. No failure or delay on the part of the Holder in the exercise of any power, right or privilege
hereunder shall operate as a waiver thereof, nor shall any single or partial exercise of any such power, right or privilege preclude
other or further exercise thereof or of any other right, power or privileges. All rights and remedies existing hereunder are cumulative
to, and not exclusive of, any rights or remedies otherwise available.

 

4.2
Notices. All notices, demands, requests, consents, approvals, and other communications required or permitted hereunder shall be
in writing and, unless otherwise specified herein, shall be (i) personally served, (ii) deposited in the mail, registered or certified,
return receipt requested, postage prepaid, (iii) delivered by reputable air courier service with charges prepaid, or (iv) transmitted
by hand delivery, telegram, facsimile or email, addressed as set forth below or to such other address as such party shall have specified
most recently by written notice. Any notice or other communication required or permitted to be given hereunder shall be deemed effective
(a) upon hand delivery or delivery by facsimile, with accurate confirmation generated by the transmitting facsimile machine, at the address
or number designated below (if delivered on a business day during normal business hours where such notice is to be received), or the
first business day following such delivery (if delivered other than on a business day during normal business hours where such notice
is to be received) or (b) on the second business day following the date of mailing by express courier service, fully prepaid, addressed
to such address, or upon actual receipt of such mailing, whichever shall first occur. The addresses for such communications shall be:

 

If
to the Borrower, to:

 

RAINMAKER
WORLDWIDE INC.

271
Brock Street

Peterborough,
Ontario, Canada K9H 2P8

Attn:
Michael O’Connor, Chief Executive Officer

 

If
to the Holder:

 

4.3
Amendments. This Note and any provision hereof may only be amended by an instrument in writing signed by the Borrower and the
Holder. The term “Note” and all reference thereto, as used throughout this instrument, shall mean this instrument (and the
other Notes issued pursuant to the Purchase Agreement) as originally executed, or if later amended or supplemented, then as so amended
or supplemented.

 

4.4
Assignability. This Note shall be binding upon the Borrower and its successors and assigns and shall inure to be the benefit of
the Holder and its successors and assigns. Each transferee of this Note must be an “accredited investor” (as defined in Rule
501(a) of the Securities and Exchange Commission). Notwithstanding anything in this Note to the contrary, this Note may be pledged as
collateral in connection with a bona fide margin account or other lending arrangement; and may be assigned by the Holder without
the consent of the Borrower.

 

    	 

     

    

 

4.5
Cost of Collection. If default is made in the payment of this Note, the Borrower shall pay the Holder hereof costs of collection,
including reasonable attorneys’ fees.

 

4.6
Governing Law. This Note shall be governed by and construed in accordance with the laws of the Commonwealth of Virginia without
regard to principles of conflicts of laws. Any action brought by either party against the other concerning the transactions contemplated
by this Note shall be brought only in the Circuit Court of Fairfax County, Virginia or in the Alexandria Division of the United States
District Court for the Eastern District of Virginia. The parties to this Note hereby irrevocably waive any objection to jurisdiction
and venue of any action instituted hereunder and shall not assert any objection or defense based on lack of jurisdiction or venue or
based upon forum non conveniens. The Borrower and Holder waive trial by jury. The Holder shall be entitled to recover from the
Borrower its reasonable attorney’s fees and costs incurred in connection with or related to any Event of Default by the Company,
as defined in Article III hereof. In the event that any provision of this Note or any other agreement delivered in connection herewith
is invalid or unenforceable under any applicable statute or rule of law, then such provision shall be deemed inoperative to the extent
that it may conflict therewith and shall be deemed modified to conform with such statute or rule of law. Any such provision which may
prove invalid or unenforceable under any law shall not affect the validity or enforceability of any other provision hereof or any agreement
delivered in connection herewith. Each party hereby irrevocably waives personal service of process and consents to process being served
in any suit, action or proceeding in connection with this Note, any agreement or any other document delivered in connection with this
Note 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 Note 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 other manner permitted
by law.

 

4.7
Purchase Agreement. By its acceptance of this Note, each party agrees to be bound by the applicable terms of the Purchase Agreement.

 

4.8
Remedies. The Borrower acknowledges that a breach by it of its obligations hereunder will cause irreparable harm to the Holder,
by vitiating the intent and purpose of the transaction contemplated hereby. Accordingly, the Borrower acknowledges that the remedy at
law for a breach of its obligations under this Note will be inadequate and agrees, in the event of a breach or threatened breach by the
Borrower of the provisions of this Note, that the Holder shall be entitled, in addition to all other available remedies at law or in
equity, and in addition to the penalties assessable herein, to an injunction or injunctions restraining, preventing or curing any breach
of this Note and to enforce specifically the terms and provisions thereof, without the necessity of showing economic loss and without
any bond or other security being required.

 

 

IN
WITNESS WHEREOF, Borrower has caused this Note to be signed in its name by its duly authorized officer this on September 12, 2022

 

	RAINMAKER
    WORLDWIDE INC.	 
	 	 
	By:
    	 	 
	 	Michael
    O’Connor	 
	 	Chief
    Executive Officer	 

 

    	 

     

    

 

EXHIBIT
A — NOTICE OF CONVERSION

 

The
undersigned hereby elects to convert $ principal amount of the Note (defined below) into that number of shares of Common Stock to be
issued pursuant to the conversion of the Note (“Common Stock”) as set forth below, of RAINMAKER WORLDWIDE INC., a Nevada
corporation (the “Borrower”) according to the conditions of the convertible note of the Borrower dated as of September 12,
2022 (the “Note”), as of the date written below. No fee will be charged to the Holder for any conversion, except for transfer
taxes, if any.

 

Box
Checked as to applicable instructions:

 

	 	[  ]	The
    Borrower shall electronically transmit the Common Stock issuable pursuant to this Notice of Conversion to the account of the undersigned
    or its nominee with DTC through its Deposit Withdrawal Agent At Custodian (“DWAC Transfer”).
	 	 	 
	 	 	Name
    of DTC Prime Broker:
	 	 	Account
    Number:
	 	 	 
	 	[  ]	The
    undersigned hereby requests that the Borrower issue a certificate or certificates for the number of shares of Common Stock set forth
    below (which numbers are based on the Holder’s calculation attached hereto) in the name(s) specified immediately below or,
    if additional space is necessary, on an attachment hereto:

 

	 	Date
    of conversion:	 	 
	 	Applicable
    Conversion Price:	$	 
	 	Number
    of shares of common stock to be issued pursuant to conversion of the Notes:	 	 
	 	Amount
    of Principal Balance due remaining	 	 
	 	under
    the Note after this conversion:	 	 

 

	 	By:	 	 
	 	Name:	 	 
	 	Title:	 	 
	 	Date:

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