SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

SCHEDULE 13G

Under the Securities Exchange Act of 1934
(Amendment No. )*

Gaucho Group Holdings, Inc. 

(Name of Issuer)

Common Stock, par value $0.01 per share 

(Title of Class of Securities)

36809R404 

(CUSIP Number)

February 6, 2024 

(Date of Event which Requires Filing of this Statement)

Check the appropriate box to designate the rule pursuant to which this Schedule is filed:

☐ Rule 13d-1(b)
☒ Rule 13d-1(c)
☐ Rule 13d-1(d)

^* The remainder of this cover page shall be filled out for a reporting person’s initial filing on this form with respect to the subject class of securities, and for any subsequent amendment containing information which would alter disclosures provided in a prior cover page.

The information required on the remainder of this cover page shall not be deemed to be “filed” for the purpose of Section 18 of the Securities Exchange Act of 1934 (“Act”) or otherwise subject to the liabilities of that section of the Act but shall be subject to all other provisions of the Act (however, see the Notes).  

(1)  As more fully described in Item 4 of this Statement on Schedule 13G (this “Statement”), such shares and percentage do not give full effect to the (i) shares of common stock, par value $0.01 per share (the “Common Stock”), issuable upon full exercise of common stock purchase warrants held by the reporting person (the “Warrants”), which exercise in each case is subject to a 4.99% beneficial ownership blocker, or (ii) Common Stock issuable upon full conversion of a senior secured convertible note (the “Note”) held by the reporting person, which conversion is subject to a 9.99% beneficial ownership blocker.

(1)  As more fully described in Item 4 of this Statement, such shares and percentage do not give full effect to the (i) Common Stock issuable upon full exercise of the Warrants, which exercise in each case is subject to a 4.99% beneficial ownership blocker, or (ii) Common Stock issuable upon full conversion of the Note, which conversion is subject to a 9.99% beneficial ownership blocker.

(1)  As more fully described in Item 4 of this Statement, such shares and percentage do not give full effect to the (i) Common Stock issuable upon full exercise of the Warrants, which exercise in each case is subject to a 4.99% beneficial ownership blocker, or (ii) Common Stock issuable upon full conversion of the Note, which conversion is subject to a 9.99% beneficial ownership blocker.

Item 1(a). Name of Issuer:

Gaucho Group Holdings, Inc. (the “Issuer”).

Item 1(b). Address of Issuer’s Principal Executive Offices:

The Issuer’s principal executive offices are located at 112 NE 41^st Street, Suite 106, Miami, FL 33137.

Item 2(a). Names of Persons Filing:

The foregoing persons are hereinafter sometimes collectively referred to as the “Reporting Persons”. Any disclosures herein with respect to persons other than the Reporting Persons are made on information and belief after making inquiry to the appropriate party.

The Reporting Persons have entered into a Joint Filing Agreement, a copy of which is filed with this Schedule 13G as Exhibit 1, pursuant to which they have agreed to file this Schedule 13G jointly in accordance with the provisions of Rule 13d-1(k) of the Act.

The filing of this Schedule 13G should not be construed in and of itself as an admission by any Reporting Person as to beneficial ownership of the securities reported herein.  

Item 2(b). Address of Principal Business Office or, if none, Residence:

The principal business address of each of the Reporting Persons is 2 Wooster Street, 2^nd Floor, New York, NY 10013.

Item 2(c). Citizenship:

3i is a Delaware limited partnership. 3i Management is a Delaware limited liability company. Mr. Tarlow is a citizen of the United States.

Item 2(d). Title of Class of Securities:

The title of the class of securities to which this statement relates is the Issuer’s common stock, par value $0.01 per share (the “Common Stock”).

Item 2(e). CUSIP Number: 36809R404

Item 3. If This Statement is Filed Pursuant to §§240.13d-1(b) or 240.13d-2(b) or (c), Check Whether the Person Filing is a:

Not applicable.

Item 4. Ownership.

The information required by this item with respect to each Reporting Person is set forth in Rows 5 through 9 and 11 of the cover page to this Schedule 13G and is incorporated herein by reference for each such Reporting Person. The ownership percentages reported are based on (i) 5,647,763 shares of Common Stock outstanding as reported in the Issuer’s Current Report on Form 8-K, filed with the U.S. Securities and Exchange Commission on February 7, 2024, and (ii) 626,832 shares of Common Stock issuable, in any combination, to 3i upon (x) the full exercise of Common Stock purchase warrants exercisable for up to an aggregate of 350,526 shares of Common Stock (the “Warrants”), which in each case is subject to a 4.99% beneficial ownership blocker, and (y) the full conversion of the senior secured convertible note (the “Note”), which is subject to a 9.99% beneficial ownership blocker (the “Blocker”).

3i holds the Warrants exercisable for up to an aggregate of 350,526 shares of Common Stock and the Note convertible into a number of shares of Common Stock pursuant to, and in accordance with, the conversion price and terms of the Convertible Note, subject to the Blocker. Due to the interaction between the Blocker and the 4.99% beneficial ownership limitation in each Warrant, 3i is prohibited from exercising the Warrants and/or converting the Note into shares of Common Stock if, as a result of such exercise or conversion, respectively, 3i, together with its affiliates and any persons acting as a group together with 3i or any such affiliates, would beneficially own more than 4.99% or 9.99% of the total number of shares of Common Stock then issued and outstanding immediately after giving effect to such exercise or conversion, as applicable.

Consequently, 3i is the beneficial owner of 626,832 shares of Common Stock (the “Shares”). 3i has the power to dispose of and the power to vote the Shares beneficially owned by it, which power may be exercised by 3i Management, the manager and general partner of 3i. Mr. Tarlow, as the manager of 3i Management, has shared power to vote and/or dispose of the Shares beneficially owned by each of 3i and 3i Management. Mr. Tarlow does not directly own the Shares. By reason of the provisions of Rule 13d-3 of the Act, Mr. Tarlow may be deemed to beneficially own the Shares beneficially owned by 3i and 3i Management, and 3i Management may be deemed to beneficially own the Shares beneficially owned by 3i.

Item 5. Ownership of Five Percent or Less of a Class.

If this statement is being filed to report the fact that as of the date hereof the reporting person has ceased to be the beneficial owner of more than five percent of the class of securities, check the following ☐.

Item 6. Ownership of More than Five Percent on Behalf of Another Person.

Not applicable.  

Item 7. Identification and Classification of the Subsidiary Which Acquired the Security Being Reported on By the Parent Holding Company.

Not applicable.

Item 8. Identification and Classification of Members of the Group.

Not applicable.

Item 9. Notice of Dissolution of Group.

Not applicable.

Item 10. Certification.

By signing below each of the Reporting Persons certify that, to the best of each of their knowledge and belief, the securities referred to above were not acquired and are not held for the purpose of or with the effect of changing or influencing the control of the issuer of the securities and were not acquired and are not held in connection with or as a participant in any transaction having that purpose or effect, other than activities solely in connection with a nomination under § 240.14a-11.

After reasonable inquiry and to the best of my knowledge and belief, I certify that the information set forth in this statement is true, complete and correct.

EXHIBIT 1

JOINT FILING AGREEMENT 

PURSUANT TO RULE 13d-1(k)

The undersigned acknowledge and agree that the foregoing statement on Schedule 13G is filed on behalf of each of the undersigned and that all subsequent amendments to this statement on Schedule 13G shall be filed on behalf of each of the undersigned without the necessity of filing additional joint filing agreements. The undersigned acknowledge that each shall be responsible for the timely filing of such amendments, and for the completeness and accuracy of the information concerning him or it contained herein and therein, but shall not be responsible for the completeness and accuracy of the information concerning the others, except to the extent that he or it knows or has reason to believe that such information is inaccurate. The undersigned hereby further agree that this Joint Filing Agreement may be executed in any number of counterparts, each of which when so executed shall be deemed to be an original, but all of which counterparts shall together constitute one and the same instrument.