Document:

Exhibit
4.1

 

AMENDMENT
TO THE CERTIFICATE OF DESIGNATION OF SERIES B

CONVERTIBLE PREFERRED STOCK OF

GAUCHO GROUP HOLDINGS, INC.

 

PURSUANT
TO SECTION 242 OF THE

DELAWARE GENERAL CORPORATION LAW

 

Gaucho
Group Holdings, Inc., a corporation organized and existing under the General Corporation Law of the State of Delaware (hereinafter
called the “Corporation”), DOES HEREBY CERTIFY:

 

That
pursuant to resolutions adopted by unanimous consent of the Board of Directors of the Corporation, and the resolutions adopted
by the holders of a majority of the issued and outstanding shares of Series B Convertible Preferred Stock, the Certificate of
Designation for the Series B Convertible Preferred Stock, $0.01 par value per share, dated February 21, 2017, as amended on December
3, 2019 and as further amended on January 30, 2020 (the “Certificate of Designation”), is further amended as follows:

 

1.
Section 5(a) of the Certificate of Designation be and it hereby is deleted in its entirety and a new Section 5(a) be inserted
in lieu thereof to read as follows:

 

5.
Conversion Rights; Mandatory Conversion. The
holders of the Series B Convertible Preferred Stock shall have the following rights and obligations with respect to the conversion
of such shares into shares of Common Stock:

 

(a)
Voluntary Conversion. Subject to and in compliance with the provisions of this Section 5, on or before December
31, 2020, the holder of shares of Preferred Stock may elect to convert such shares into fully-paid and non-assessable shares of
Common Stock, except that the Company shall not be required to convert less than 2,500 shares of Series B Convertible Preferred
Stock in the event such holder seeks to convert less than all of such holder’s shares. Holders will be notified of the date
on which the right to voluntarily convert provided for herein shall expire. The number of shares of Common Stock that a holder
of Series B Convertible Preferred Stock shall be entitled to receive upon conversion shall be the product obtained by multiplying
the Series B Applicable Conversion Rate (determined as provided in Section 5(b)) by the number of shares of Series B Convertible
Preferred Stock being converted at any time.

 

2.
Section 6(a) of the Certificate of Designation be and it hereby is deleted in its entirety and a new Section 6(a) be inserted
in lieu thereof to read as follows:

 

6.
Redemption.

 

(a)
Redemption of Preferred Stock. Subject to the provisions of Section 5, and any actions previously taken pursuant thereto,
on December 31, 2020 (the “Redemption Date”), the Corporation shall redeem all then-outstanding shares of Series B
Preferred Stock (“Series B Redemption”) for a price per Share equal to the Liquidation Value for such Share, plus
all unpaid accrued and accumulated dividends on such Share (whether or not declared) (the “Series B Redemption Price,”
for all holders collectively, the “Aggregate Series B Redemption Price”). The Aggregate Series B Redemption Price
shall be payable in immediately available funds to the respective holders of the Series B Preferred Stock within sixty (60) days
following the Redemption Date and the Corporation shall contribute all of its assets to the payment of the Aggregate Series B
Redemption Price, and to no other corporate purpose, except to the extent prohibited by applicable Delaware law.

 

    	 

    	 

    

 

IN
WITNESS WHEREOF, this Amendment to the Certificate of Designation has been executed on behalf of the Corporation by its Chief
Executive Officer, and attested by its Secretary, this 30th day of March, 2020.

 

	 	Gaucho
    Group Holdings, Inc.
	 	 
	 	By:	/s/Scott
    Mathis
	 	Name:
    	Scott
    Mathis
	 	Title:
    	Chief
    Executive Officer

 

	Attest:	 
	 	 
	/s/
    Maria Echevarria	 
	Maria
    Echevarria, Secretary	 

 

    	-2-Exhibit
10.1

 

 

March
29, 2020

 

Mr.
Scott L. Mathis

Gaucho
Group Holdings, Inc.

135
Fifth Ave., 10th Floor

New
York, NY 10010

 

Re:
Employee Retention Bonus Agreement

 

Dear
Scott:

 

As
I hope you know, Gaucho Group Holdings, Inc. (“GGH” or the “Company”) greatly values the efforts you have
made in the past on behalf of the Company. We consider your continued service and dedication to GGH essential to our future, and
to incentivize you further to remain employed with GGH and to continue doing the great job you have been doing, we are pleased
to offer you a “Retention Bonus.”

 

In
recognition of your continued service with GGH from the date of this letter and for an additional three (3) years thereafter (referred
to as the “Retention Period”), we are offering you a Retention Bonus as described in more detail below and in the
accompanying Schedule A. As you know, GGH’s liquid (cash) assets are deployed for building and developing corporate assets,
so we are offering you the opportunity to obtain ownership of one of the lots owned by the Company at Algodon Wine Estates (“AWE”)
in San Rafael, Mendoza, Argentina.

 

The
specific lot which you will have the opportunity to acquire (your “AWE Lot”) was previously designated, and as you
know you have been building a house on that property with your personal funds.

 

You
will be eligible to receive this Retention Bonus if all of the following eligibility criteria are satisfied:

 

	 	●	Your
    performance has been satisfactory, as determined in the sole discretion of the Company’s Board of Directors, from the
    date of this letter through the end of the Retention Period; and
	 	 	 
	 	●	You
    are actively employed by GGH on the last day of the Retention Period.

 

Notwithstanding
the foregoing, you will be eligible to receive a pro-rata portion of the Retention Bonus if your employment by GGH is terminated
prior to the last day of the Retention Period. This is explained in Schedule A.

Upon
establishing ownership of your AWE Lot at the time the property is deeded to you, the value of that lot (less any amount paid
to acquire the lot, as explained in Schedule A) would be treated as taxable U.S. compensation, and you will be responsible for
all federal and state income tax owed on that compensation. A Form W-2 or 1099 would be issued for the year in which your AWE
Lot is deeded to you.

 

This
letter agreement is intended to comply with, or be exempt from, Section 409A of the Internal Revenue Code of 1986, as amended
(“Section 409A”) and shall be construed and administered in accordance with Section 409A.

 

GAUCHO GROUP HOLDINGS, INC. GROUP (OTCQB:VINO)

135 FIFTH AVENUE, FLOOR 10, NEW YORK, NY 10010

(toll free) 866.960.7700 (main) 212.739.7700
(fax) 212.655.0140 | www.gauchobuenosaires.com

 

    	 

    	 

    

 

This
letter agreement and Schedule A attached hereto contain all of the understandings and representations between GGH and you relating
to the Retention Bonus and supersedes all prior and contemporaneous understandings, discussions, agreements, representations,
and warranties, both written and oral, with respect to the Retention Bonus. This letter agreement may not be amended or modified
unless in writing signed by both you and an authorized representative of the Company’s Board of Directors.

 

This
letter agreement and all related documents, including Schedule A, and all matters arising out of or relating to this letter agreement,
whether sounding in contract, tort, or statute are governed by, and construed in accordance with, the law of the State of New
York, without giving effect to the conflict of laws provisions thereof to the extent such principles or rules would require or
permit the application of the laws of any jurisdiction other than those of the State of New York.

 

Please
sign and date this letter agreement and return the signed copy to the Company’s Chief Financial Officer within fifteen (15)
days of the date of this letter.

 

We
very much look forward to your continued employment with GGH.

 

	 	Very
    truly yours,
	 	 
	 	GAUCHO
    GROUP HOLDINGS, INC.
	 	 
	 	By:	/s/Steven
    Moel
	 	 	Steven
    Moel, Director, on behalf of the Board of Directors

 

	AGREED
    TO AND ACCEPTED:	 
	 	 
	/s/Scott
    L. Mathis	 
	SCOTT
    L. MATHIS	 

 

    	 

    	 

    

 

SCHEDULE
A

 

	Employee
    Name:	Scott
    Mathis	 	(the
    “Employee”)
	 	 	 	 
	Retention
    Bonus Grant Date:	March
    29, 2020	 	(the
    “Grant Date”)
	 	 	 	 
	Algodon
        Wine Estates

        Lot
        Number:
	D11	 	(the
    “AWE Lot”)
	 	 	 	 
	AWE
    Lot Fair Market Value:	U.S.
$ 115,000	1	(the
    “Purchase Price”)

 

	Vesting
    Schedule: 	On
    the third anniversary of the Grant Date, which is the end of the Retention Period, Employee shall be fully vested in the AWE
    Lot.
	 	 
	 	If
    employment with Algodon should terminate prior to the end of the Retention Period for any reason, Employee will have the right
    to the following: (a) if employment ends on or after the first anniversary of the Grant Date, Employee can purchase the AWE
    Lot for 67% of the Purchase Price; and (b) if employment ends on or after the second anniversary of the Grant Date, Employee
    can purchase the AWE Lot for 33% of the Purchase Price.
	 	 
	 	Employee
    shall have the right to accept his or her vested interest for 100%, 67% or 33% of the AWE Lot for a period of sixty (60) days
    after the interest in the AWE Lot vests (the “Vesting Date”). Employee can decline to accept the benefit provided
    hereby for any reason.
	 	 
	Deeding
    requirement: 	Before
    ownership of the AWE Lot can be transferred to Employee, the Company must be legally permitted to issue a deed for the property.
    In the event a deed for the AWE Lot is not issuable as of the Vesting Date, Employee’s right to ownership shall be delayed
    without penalty or additional cost until such time as the AWE Lot may be legally deeded. 
	 	 
	 	In
    the unlikely event that the Company cannot for any reason deliver a deed for the AWE Lot within 24 months after the Vesting
    Date (e.g., project abandonment, governmental limitations, Act of God), the Company shall provide to Employee a different
    lot located at AWE that is substantially equivalent in value and which, to the extent practicable, has qualities and attributes
    (such as location and view) which are similar to those of the AWE Lot.
	 	 
	 	In
    light of the foregoing limitations, conditions and potential delays, and to the extent legally permissible, Employee’s
    acceptance of the benefit provided hereunder shall not be deemed to constitute or generate taxable compensation until such
    time that the AWE Lot (or a mutually agreed upon replacement) is deeded to Employee.
	 	 
	Closing
    Fees:	The
    usual and customary closing fees associated with the sale of a lot at AWE shall be allocated between the Company and Employee
    in the same manner as that used in arms’ length transactions with unaffiliated lot purchasers.

 

 

1
Fair Market Value is determined as of Grant Date

 

    	 

    	 

    

 

	Property
        Expenses and

        Real
        Estate Taxes:
	All
    fees and expenses, including maintenance fees generally charged to owners of lots at AWE, and any local real estate taxes,
    shall remain the responsibility of the Company until the date that the deed for the AWE Lot is transferred to Employee.
	 	 
	 	After
    transfer of the Deed, Employee shall be responsible for payment of (a) all maintenance fees charged by AWE, subject to the
    following paragraph, and (b) all property taxes assessed by the local municipalities or other Argentine tax authorities. 
	 	 
	 	Notwithstanding
    the foregoing, for a period of seven (7) years following transfer of the deed, maintenance fees assessed by AWE shall be capped
    at US $100 per month. At the end of the seven year period, the amount of maintenance fees shall be calculated in accordance
    with the Company’s standard policies and practices used to calculate the fees charged to arms’ length lot purchasers,
    subject to a lifetime maximum of $250 per month.
	 	 
	 	The
    $250/month limitation is based on the fact that the Company recognizes that 100% of the construction cost of the house located
    on the AWE Lot and all of its landscaping has been paid for to date entirely by Employee for the benefit of AWE marketing
    efforts, and that the house being built on the AWE Lot has been used as a model home for the benefit of AWE and will continue
    to be used as a model home for AWE. This has allowed AWE to show the home to other prospective buyers, show the quality of
    the construction, induce others to purchase, and help others visualize the “Algodon Lifestyle” and its potential.

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