Scott L. Mathis - Mar 28, 2022 Form 4 Insider Report for Gaucho Group Holdings, Inc. (VINO)

Role: President, CEO, Chair. & Dir., Director
Signature: /s/ Scott L. Mathis
Stock symbol: VINO
Transactions as of: Mar 28, 2022
Transactions value $: $1,297,480
Form type: 4
Date filed: 6/24/2022, 08:55 PM
Previous filing: Mar 29, 2022
Next filing: Nov 2, 2022

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	VINO	Common Stock	Award	$7.49K	+3.71K	+15.61%	$2.02	27.5K	Mar 28, 2022	Direct	F1
transaction	VINO	Common Stock	Award	$1.13M	+1.81M	+6571.74%	$0.63	1.83M	Jun 24, 2022	Direct	F2
holding	VINO	Common Stock						22.9K	Mar 28, 2022	See Footnote	F3
holding	VINO	Common Stock						1.28M	Mar 28, 2022	See Footnote	F4
holding	VINO	Common Stock						252K	Mar 28, 2022	See Footnote	F5

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	VINO	Restricted Stock Unit	Award	$161K	+258K		$0.63	258K	Jun 24, 2022	Common Stock	258K	$0.63	Direct	F6
holding	VINO	Stock Option						147K	Mar 28, 2022	Common Stock	147K	$5.78	Direct	F7
holding	VINO	Stock Option						30K	Mar 28, 2022	Common Stock	30K	$5.78	Direct	F8
holding	VINO	Stock Option						48.3K	Mar 28, 2022	Common Stock	48.3K	$8.09	Direct	F9
holding	VINO	Stock Option						66.7K	Mar 28, 2022	Common Stock	66.7K	$11.55	Direct	F10
holding	VINO	Stock Option						20K	Mar 28, 2022	Common Stock	20K	$16.50	Direct	F11

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	Inadvertently omitted. Acquired as a result of the share exchange with the minority stockholders of Gaucho Group, Inc.
F2	Acquired in connection with the conversion of outstanding options of Gaucho Group, Inc.
F3	Shares held by Mr. Mathis' 401(k) account.
F4	Shares issued in connection with land purchase to Hollywood Burger Holdings, Inc., of which Mr. Mathis is President and CEO and a controlling owner.
F5	Shares held by The WOW Group, LLC, of which Mr. Mathis is a managing member and of which Mr. Mathis is a controlling member.
F6	Restricted stock units issued pursuant to Gaucho's 2018 Equity Incentive Plan; 128,999 shares vest on 9/18/22 with the remainder vesting on 12/18/22.
F7	Stock options granted pursuant to 2018 Equity Incentive Plan; options to acquire 36,832 shares vest on 7/8/20; thereafter options to acquire 9,208 shares vest every three months in equal installments.
F8	Stock options granted pursuant to 2018 Equity Incentive Plan; options to acquire 7,500 shares vest on 1/31/20; thereafter options to acquire 1,875 shares vest every three months in equal installments.
F9	Stock options granted pursuant to 2018 Equity Incentive Plan; options to acquire 12,084 shares vest on 9/20/19; thereafter options to acquire 3,021 shares vest every three months in equal installments with the last installment of 3,020 vesting on 9/20/22.
F10	Stock options granted pursuant to 2016 Equity Incentive Plan; options to acquire 16,667 shares vest on 2/14/19; thereafter options to acquire 4,167 shares vest every three months.
F11	Stock options granted pursuant to 2016 Equity Incentive Plan; options to acquire 5,000 shares vest on 12/17/18; thereafter options to acquire 1,250 shares vest every three months.