SEC Form 4 · accession 0001493152-18-008101

Gaucho Group Holdings, Inc. · VINO

Statement of changes in beneficial ownership, as filed. Original on EDGAR ↗

Reporting owner

Scott L Mathis

Officer — President, CEO, Chair. & Dir. · Director · 10% Owner

Period of report

May 29, 2018

Accepted (ET)

Jun 1, 2018 · 6:06 am EDT

Rule 10b5-1 plan

unknown — predates the checkbox

Issuer CIK

0001559998

Table I — non-derivative securities

Security	Date	Code	Shares	Price	A/D	Owned after	D/I	Nature of ownership
Common Stock^F3	May 29, 2018	J	46,122	$0.63	D	3,777,425	I	see footnote
Series B Preferred Stock^F2,F1	holding	—	—		—	2,100	I	see footnote
Common Stock^F1	holding	—	—		—	164,308	I	see footnote
Common Stock	holding	—	—		—	336,545	D

Table II — derivative securities

Security	Conv. / exercise price	Date	Code	Shares	A/D	Exercisable	Expires	Underlying	Underlying shares	Owned after	D/I
Stock Option^F6	$2.48	May 31, 2018	J	1,000,000	D	Jun 30, 2013	Jun 30, 2018	Common Stock	1,000,000	0	D
Stock Option^F4	$0.77	holding	—	—	—	—	Feb 14, 2023	Common Stock	1,000,000	1,000,000	D
Stock Option^F5	$1.10	holding	—	—	—	—	Dec 17, 2022	Common Stock	300,000	300,000	D
Stock Option^F6	$2.48	holding	—	—	—	Aug 27, 2015	Aug 27, 2015	Common Stock	150,000	150,000	D
Stock Option^F6,F7	$2.48	holding	—	—	—	—	Aug 27, 2019	Common Stock	500,000	500,000	D
Stock Option^F6,F8	$2.20	holding	—	—	—	—	Jun 8, 2020	Common Stock	1,459,890	1,459,890	D
Warrant^F9	$2.30	holding	—	—	—	Jun 30, 2013	Jun 30, 2018	Common Stock	2,460	2,460	D
Warrant^F9	$2.30	holding	—	—	—	Sep 30, 2013	Sep 30, 2018	Common Stock	27,561	27,561	D
Warrant^F9	$2.30	holding	—	—	—	Dec 31, 2013	Dec 31, 2018	Common Stock	36,031	36,031	D
Warrant^F9	$2.30	holding	—	—	—	Mar 31, 2014	Mar 31, 2019	Common Stock	59,053	59,053	D
Warrant^F9	$2.30	holding	—	—	—	Jun 30, 2014	Jun 30, 2019	Common Stock	58,834	58,834	D
Warrant^F9	$2.30	holding	—	—	—	Sep 30, 2014	Sep 30, 2019	Common Stock	31	31	D
Warrant^F9	$2.30	holding	—	—	—	Dec 30, 2014	Dec 30, 2019	Common Stock	40,364	40,364	D
Warrant	$2.00	holding	—	—	—	Dec 30, 2014	Dec 30, 2019	Common Stock	10,800	10,800	D
Warrant	$2.00	holding	—	—	—	Mar 31, 2015	Mar 31, 2020	Common Stock	24,600	24,600	D
Warrant	$2.00	holding	—	—	—	Jun 30, 2015	Jun 30, 2020	Common Stock	43,589	45,589	D
Warrant	$2.00	holding	—	—	—	Sep 30, 2015	Sep 30, 2020	Common Stock	28,481	28,481	D
Warrant	$2.00	holding	—	—	—	Dec 31, 2015	Dec 31, 2020	Common Stock	3,518	3,518	D

Explanation of responses

F1Shares held by Mr. Mathis' 401(k) account.
F10Expiration of stock options with no value received.
F2Series 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.
F3Shares held by The WOW Group, LLC, of which Mr. Mathis is a managing member and of which Mr. Mathis is a controlling member. Reflects a transfer of Company shares to certain WOW Group members in redemption of their WOW Group interests.
F4Stock options granted pursuant to 2016 Equity Incentive Plan; options to acquire 250,000 shares vest on 2/14/19; thereafter options to acquire 187,500 shares vest every three months in equal installments.
F5Stock 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 in equal installments.
F6Options granted pursuant to AWLD's 2008 Equity Incentive Plan.
F7Options to acquire 31,250 vest on November 27, 2014; thereafter options to acquire 31,250 shares vest every three months in equal installments.
F8Options to acquire 364,974 vest on June 8, 2016; thereafter options to acquire 91,243 shares vest every three months in equal installments.
F9Warrants 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.