Letter Agreement, dated as of February 8, 2023, by and among Gaucho Group Holdings, Inc. and the subscribers listed therein

Exhibit 10.1

From the Desk of Scott Mathis   Direct: 212 ###-###-#### Fax: 212 ###-###-#### ***@***

February 8, 2023

3i, LP

140 Broadway Floor 38

New York, NY 10005

Nomis Bay, Ltd.

Wessex House 3rd Floor

45 Reid Street

Hamilton, HM 12

Bermuda

BPY Limited

Wessex House 3rd Floor

45 Reid Street

Hamilton, HM 12

Bermuda

Re: Modification to Purchase Agreement

Dear Sirs:

Reference is made to (a) that certain Securities Purchase Agreement dated as of November 3, 2021 (the “Purchase Agreement”) between the Company and the purchasers identified therein, which are the same as the three addressees listed above (collectively, the “Investors”), (b) a series of certain Amendment and Exchange Agreements dated as of February 22, 2022, September 22, 2022 and November 30, 2022 between the Company and the Investors, (c) those certain letter agreements between the Company and the Investors on each of May 2, 2022, May 12, 2022, and July 1, 2022, (d) a series of senior secured convertible notes of the Company issued to the Investors (the “Notes”), (e) and the other transaction documents, as modified from time to time, referred to collectively, as the “Transaction Documents”. Capitalized terms used but not defined herein shall have the meanings given to them in the Purchase Agreement, or if not defined therein, in the Notes, or if not defined therein, in the applicable Transaction Document, in each case as of the date hereof.

This letter agreement (this “Letter Agreement”) confirms our recent discussions about, among other matters, certain modifications to the Purchase Agreement.

GAUCHO GROUP HOLDINGS, INC. GROUP (NASDAQ:VINO)

112 NE 41^ST STREET, SUITE 106, MIAMI, FL 33137

(main) 212 ###-###-#### (fax) 212 ###-###-#### | www.gauchoholdings.com

This Letter Agreement is a Transaction Document and is limited as written. As of the date first written above, each reference in the Purchase Agreement or any other applicable Transaction Document to “this Agreement,” “hereunder,” “hereof,” “herein,” or words of like import, and each reference in the other Transaction Documents to such Purchase Agreement or other Transaction Documents (including, without limitation, by means of words like “thereunder,” “thereof” and words of like import), shall refer to the Purchase Agreement as modified thereby, and this Letter Agreement and the Purchase Agreement shall be read together and construed as a single agreement. The execution, delivery and effectiveness of this Letter Agreement shall not, except as expressly provided herein, (A) waive or modify any right, power or remedy under, or any other provision of, any Transaction Document or (B) commit or otherwise obligate any Purchaser to enter into or consider entering into any other amendment, waiver or modification of any Transaction Document.

All communications and notices hereunder shall be given as provided in the Transaction Documents. This Letter Agreement (a) shall be governed by and construed in accordance with the law of the State of New York, (b) is for the exclusive benefit of the parties hereto and the other Purchasers and beneficiaries of the Purchaser Agreement and, together with the other Transaction Documents, constitutes the entire agreement of such parties, superseding all prior agreements among them, with respect to the subject matter hereof, (c) may be modified, waived or assigned only in writing and only to the extent such modification, waiver or assignment would be permitted under the Transaction Documents (and any attempt to assign this Letter Agreement without such writing shall be null and void), (d) is a negotiated document, entered into freely among the parties upon advice of their own counsel, and it should not be construed against any of its drafters and (e) shall survive the satisfaction or discharge of the amounts owing under the Transaction Documents. The fact that any term or provision of this Letter Agreement is held invalid, illegal or unenforceable as to any person in any situation in any jurisdiction shall not affect the validity, enforceability or legality of the remaining terms or provisions hereof or the validity, enforceability or legality of such offending term or provision in any other situation or jurisdiction or as applied to any person.

This Letter Agreement is expressly conditioned on the following conditions precedent:

Kindly confirm your agreement with the above by signing in the space indicated below and by PDFing a partially executed copy of this letter to the undersigned, and which may be executed in identical counterparts, each of which shall be deemed an original but all of which shall constitute one and the same agreement.

[Signatures follow on next page]

AGREED AND ACCEPTED:

3i, LP

Name: Maier J Tarlow

Title: Manager On Behalf Of The GP

Nomis Bay, Ltd.

Name:

Title:

BPY Limited

Name:

Title: