SEC FORM 4

SEC FORM 4 SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

1. Name and Address of Reporting Person^*

Cannon Reuben

(Last)

(First)

(Middle)

280 S. BEVERLY DRIVE #208

(Street)

BEVERLY HILLS,

90212

(City)

(State)

(Zip)

2. Issuer Name and Ticker or Trading Symbol
Gaucho Group Holdings, Inc. [ VINO ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director	10% Owner
	Officer (give title below)	Other (specify below)

3. Date of Earliest Transaction (Month/Day/Year)
08/11/2022

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Common Stock								126,876	D
Common Stock								1,960	I	See footnote⁽¹⁾

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
Restricted Stock Unit	$0.807	08/11/2022		A		46,469		⁽²⁾	12/31/2022	Common Stock	46,469	$0.807	46,469	D
Restricted Stock Unit	$0.625							⁽³⁾	12/18/2023	Common Stock	1,433		1,433	D
Warrants⁽⁴⁾	$6	08/19/2022		J			3,333	02/19/2021	08/19/2022	Common Stock	3,333	$0	0	D
Stock Option	$8.09							⁽⁵⁾	09/20/2023	Common Stock	1,000		1,000	D
Stock Option	$9.08							⁽⁶⁾	09/28/2025	Common Stock	6,667		6,667	D

Explanation of Responses:

1. Held by Reuben Cannon Productions, controlled by Mr. Cannon.

2. Restricted stock units issued pursuant to Gaucho's 2018 Equity Incentive Plan; shares vest on the earlier of 12/31/22 or pro rata to termination of service as a director.

3. Restricted stock units issued pursuant to Gaucho's 2018 Equity Incentive Plan; 717 shares vest on 9/18/22 with the remainder vesting on 12/18/22.

4. Warrants expired with no value received.

5. Options granted pursuant to 2018 Equity Incentive Plan; options to acquire 250 shares vest on 9/20/19; options to acquire 63 shares vest on 12/20/19; thereafter options to acquire 62 shares vest every three months.

6. Options granted pursuant to Gaucho's 2018 Equity Incentive Plan; options to acquire 1,667 shares vest on 9/28/21; thereafter options to acquire 417 shares vest every three months.

	/s/ Reuben Cannon	08/31/2022
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
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