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)
06/07/2022

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⁽¹⁾	06/07/2022		A		61,958	A	$0.807	70,374	D
Common Stock⁽¹⁾	06/07/2022		A		46,469	A	$0.807	116,843	D
Common Stock								1,960	I	Seefootnote⁽²⁾

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)
Warrants⁽³⁾	$6							02/19/2021	08/19/2022	Common Stock	3,333		3,333	D
Stock Option	$8.09							⁽⁴⁾	09/20/2023	Common Stock	1,000		1,000	D
Stock Option	$9.08							⁽⁵⁾	09/28/2025	Common Stock	6,667		6,667	D

Explanation of Responses:

1. Acquisition of restricted common stock of the Company as approved by the Compensation Committee and Board of Directors pursuant to the 2018 Equity Incentive Plan for services provided to the Company as a director for 2021 and half of 2022.

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

3. Purchased pursuant to a public offering of Units at a price of $6.00 per Unit, with each Unit consisting of one share of common stock and one common stock purchase warrant; each warrant has an exercise price equal to 100% of the offering price.

4. 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.

5. Options granted pursuant to AWLD'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	06/09/2022
	** 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).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

SEC Form 4: Cannon Reuben was granted 108,427 shares, increasing direct ownership by 1,288% to 116,843 units