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

Role: President, CEO, Chair. & Dir., Director
Signature: /s/ Scott L. Mathis
Issuer symbol: N/A
Transactions as of: 28 Mar 2022
Net transactions value: +$1,297,480
Form type: 4
Filing time: 24 Jun 2022, 20:55:39 UTC
Previous filing: 29 Mar 2022
Next filing: 02 Nov 2022
SEC: View on sec.gov

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	VINO	Common Stock	Award	$7,494	+3,710	+16%	$2.02	27,481	28 Mar 2022	Direct	F1
transaction	VINO	Common Stock	Award	$1,128,738	+1,805,980	+6572%	$0.6250	1,833,461	24 Jun 2022	Direct	F2
holding	VINO	Common Stock						22,867	28 Mar 2022	See Footnote	F3
holding	VINO	Common Stock						1,283,423	28 Mar 2022	See Footnote	F4
holding	VINO	Common Stock						251,829	28 Mar 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	$161,248	+257,997		$0.6250	257,997	24 Jun 2022	Common Stock	257,997	$0.6250	Direct	F6
holding	VINO	Stock Option						147,326	28 Mar 2022	Common Stock	147,326	$5.78	Direct	F7
holding	VINO	Stock Option						30,000	28 Mar 2022	Common Stock	30,000	$5.78	Direct	F8
holding	VINO	Stock Option						48,334	28 Mar 2022	Common Stock	48,334	$8.09	Direct	F9
holding	VINO	Stock Option						66,667	28 Mar 2022	Common Stock	66,667	$11.55	Direct	F10
holding	VINO	Stock Option						20,000	28 Mar 2022	Common Stock	20,000	$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.