Reuben Cannon - Aug 11, 2022 Form 4 Insider Report for Gaucho Group Holdings, Inc. (VINO)

Role: Director
Signature: /s/ Reuben Cannon
Stock symbol: VINO
Transactions as of: Aug 11, 2022
Transactions value $: $37,500
Form type: 4
Date filed: 8/31/2022, 11:28 AM
Previous filing: Jun 24, 2022
Next filing: Aug 1, 2023

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
holding	VINO	Common Stock						127K	Aug 11, 2022	Direct
holding	VINO	Common Stock						1.96K	Aug 11, 2022	See footnote	F1

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	$37.5K	+46.5K		$0.81	46.5K	Aug 11, 2022	Common Stock	46.5K	$0.81	Direct	F2
transaction	VINO	Warrants	Other	$0	-3.33K	-100%	$0.00^*	0	Aug 19, 2022	Common Stock	3.33K	$6.00	Direct	F4
holding	VINO	Restricted Stock Unit						1.43K	Aug 11, 2022	Common Stock	1.43K	$0.63	Direct	F3
holding	VINO	Stock Option						1K	Aug 11, 2022	Common Stock	1K	$8.09	Direct	F5
holding	VINO	Stock Option						6.67K	Aug 11, 2022	Common Stock	6.67K	$9.08	Direct	F6

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

Explanation of Responses:

Id	Content
F1	Held by Reuben Cannon Productions, controlled by Mr. Cannon.
F2	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.
F3	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.
F4	Warrants expired with no value received.
F5	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.
F6	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.