SEC Form 4 · accession 0001493152-17-004290

Gaucho Group Holdings, Inc. · VINO

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

Reporting owner

Scott L Mathis

Officer — President, CEO, CHM&DIR · Director · 10% Owner

Period of report

Apr 15, 2016

Accepted (ET)

Apr 21, 2017 · 6:38 pm 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^F1	Apr 19, 2017	P	9,600	$2.50	A	107,999	I	See footnote
Common Stock^F1	Apr 19, 2017	P	12,000	$2.50	A	119,999	I	See footnote
Common Stock^F2	holding	—	—		—	4,660,656	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^F3	$3.85	Apr 15, 2016	J	25,000	D	Apr 15, 2012	Apr 15, 2016	Common Stock	25,000	3,597,547	D
Stock Option^F3,F5	$3.85	Jul 6, 2016	J	422,500	D	—	Jul 6, 2016	Common Stock	422,500	3,597,547	D
Stock Option^F3	$3.85	Apr 15, 2017	J	25,000	D	Apr 15, 2013	Apr 15, 2017	Common Stock	25,000	3,597,547	D
Stock Option^F3	$2.48	holding	—	—	—	Apr 15, 2014	Apr 15, 2018	Common Stock	25,000	3,597,547	D
Stock Option^F3	$2.48	holding	—	—	—	Jun 30, 2013	Jun 30, 2018	Common Stock	1,000,000	3,597,547	D
Stock Option^F3	$2.48	holding	—	—	—	Aug 27, 2015	Aug 27, 2019	Common Stock	150,000	3,597,547	D
Stock Option^F3,F6	$2.48	holding	—	—	—	—	Aug 27, 2019	Common Stock	500,000	3,597,547	D
Stock Option^F3,F7	$2.20	holding	—	—	—	—	Jun 8, 2020	Common Stock	1,459,890	3,597,547	D
Warrant^F8	$2.30	holding	—	—	—	Oct 31, 2012	Oct 31, 2017	Common Stock	85,518	3,597,547	D
Warrant^F8	$2.30	holding	—	—	—	Dec 31, 2012	Dec 31, 2017	Common Stock	18,939	3,597,547	D
Warrant^F8	$2.30	holding	—	—	—	Mar 31, 2013	Mar 31, 2018	Common Stock	22,878	3,597,547	D
Warrant^F8	$2.30	holding	—	—	—	Jun 30, 2013	Jun 30, 2018	Common Stock	2,460	3,597,547	D
Warrant^F8	$2.30	holding	—	—	—	Sep 30, 2013	Sep 30, 2018	Common Stock	27,561	3,597,547	D
Warrant^F8	$2.30	holding	—	—	—	Dec 31, 2013	Dec 31, 2018	Common Stock	36,031	3,597,547	D
Warrant^F8	$2.30	holding	—	—	—	Mar 31, 2014	Mar 31, 2019	Common Stock	59,053	3,597,547	D
Warrant^F8	$2.30	holding	—	—	—	Jun 30, 2014	Jun 30, 2019	Common Stock	58,834	3,597,547	D
Warrant^F8	$2.30	holding	—	—	—	Sep 30, 2014	Sep 30, 2019	Common Stock	31	3,597,547	D
Warrant^F8	$2.30	holding	—	—	—	Dec 30, 2014	Dec 30, 2019	Common Stock	40,364	3,597,547	D
Warrant	$2.00	holding	—	—	—	Dec 30, 2014	Dec 30, 2019	Common Stock	10,800	3,597,547	D
Warrant	$2.00	holding	—	—	—	Mar 31, 2015	Mar 31, 2020	Common Stock	24,600	3,597,547	D
Warrant	$2.00	holding	—	—	—	Jun 30, 2015	Jun 30, 2020	Common Stock	43,589	3,597,547	D
Warrant	$2.00	holding	—	—	—	Sep 30, 2015	Sep 30, 2020	Common Stock	28,481	3,597,547	D
Warrant	$2.00	holding	—	—	—	Dec 31, 2015	Dec 31, 2020	Common Stock	3,518	3,597,547	D

Explanation of responses

F1Shares held by Mr. Mathis' 401(k) account.
F2Shares held by The WOW Group, LLC, of which Mr. Mathis is a managing member and of which Mr. Mathis is a controlling member.
F3Options reflected herein are granted pursuant to Options granted pursuant to AWLD's 2008 Equity Incentive Plan.
F4Expiration of options with no value received.
F5Options to acquire 105,625 vested on July 6, 2012; thereafter options to acquire 26,409 shares vest every three months.
F6Options to acquire 31,250 vest on November 27, 2014; thereafter options to acquire 31,250 shares vest every three months.
F7Options to acquire 364,974 vest on June 8, 2016; thereafter options to acquire 91,243 shares vest every three months.
F8Warrants 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.