Gaucho (VINOQ) Form 4 Gaucho / SCOTT L MATHIS ownership change

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^*

MATHIS SCOTT L

(Last) (First) (Middle)

135 FIFTH AVENUE, FLOOR 10

(Street)

NEW YORK, NY 10010

(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	X	10% Owner
X	Officer (give title below)		Other (specify below)
President, CEO, Chair. & Dir.

3. Date of Earliest Transaction (Month/Day/Year)
03/15/2019

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)
			Code	V	Amount	(A) or (D)	Price
Common Stock(1)	03/15/2019		A		20,000	A	$0.35	558,362	D
Common Stock								204,803	I	See footnote(2)
Series B Preferred Stock(3)								2,100	I	See footnote(2)
Common Stock								3,777,425	I	See footnote(4)

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)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Stock Option	$0.385							(5)	01/31/2024	Common Stock	450,000		450,000	D
Stock Option	$0.539							(6)	09/20/2023	Common Stock	725,000		725,000	D
Stock Option	$0.77							(7)	02/14/2023	Common Stock	1,000,000		1,000,000	D
Stock Option	$1.1							(8)	12/17/2022	Common Stock	300,000		300,000	D
Stock Option(9)	$2.48							08/27/2015	08/27/2019	Common Stock	150,000		150,000	D
Stock Option(9)	$2.48							08/27/2018	08/27/2019	Common Stock	500,000		500,000	D
Stock Option(9)	$2.2							(10)	06/08/2020	Common Stock	1,459,890		1,459,890	D
Warrant	$2.3							03/31/2014	03/31/2019	Common Stock(11)	59,053		59,503	D
Warrant	$2.3							06/30/2014	06/30/2019	Common Stock(11)	58,834		58,834	D
Warrant	$2.3							09/30/2014	09/30/2019	Common Stock(11)	31		31	D
Warrant	$2.3							12/30/2014	12/30/2019	Common Stock(11)	40,364		40,364	D
Warrant	$2							12/30/2014	12/30/2019	Common Stock	10,800		10,800	D
Warrant	$2							03/31/2015	03/31/2020	Common Stock	24,600		24,600	D
Warrant	$2							06/30/2015	06/30/2020	Common Stock	43,589		43,589	D
Warrant	$2							09/30/2015	09/30/2020	Common Stock	28,481		28,481	D
Warrant	$2							12/31/2015	12/31/2020	Common Stock	3,518		3,518	D

Explanation of Responses:

1. Shares purchased by Mr. Mathis in a private placement.

2. Shares held by Mr. Mathis' 401(k) account.

3. Series B Preferred Shares are automatically convertible to Common Shares at a ratio of 1 Preferred Share to 10 Common Shares upon uplisting to national stock exchange or prior thereto at holder's option.

4. Shares held by The WOW Group, LLC, of which Mr. Mathis is a managing member and of which Mr. Mathis is a controlling member.

5. Stock options granted pursuant to 2018 Equity Incentive Plan; options to acquire 112,500 shares vest on 1/31/20; thereafter options to acquire 28,125 shares vest every three months in equal installments.

6. Stock options granted pursuant to 2018 Equity Incentive Plan; options to acquire 181,250 shares vest on 9/20/19; thereafter options to acquire 45,313 shares vest every three months in equal installments with the last installment of 45,307 vesting on 9/20/22.

7. Stock options granted pursuant to 2016 Equity Incentive Plan; options to acquire 250,000 shares vest on 2/14/19; thereafter options to acquire 62,500 shares vest every three months.

8. Stock options granted pursuant to 2016 Equity Incentive Plan; options to acquire 75,000 shares vest on 12/17/18; thereafter options to acquire 18,750 shares vest every three months.

9. Options granted pursuant to AWLD's 2008 Equity Incentive Plan.

10. Options to acquire 364,974 vest on June 8, 2016; thereafter options to acquire 91,243 shares vest every three months.

11. Warrants to purchase Series A Preferred Stock were automatically converted to common stock on July 14, 2014 on a 1:1 basis pursuant to the effectiveness of AWLD's Form 10 filed with the SEC on May 14, 2014.

	/s/Scott L. Mathis	06/05/2019
	** Signature of Reporting Person	Date
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