Item 2.03 Creation of a Direct Financial Obligation or Obligation Under an Off-Balance Sheet Arrangement of a Registrant.

The information set forth in Section 3.02 of this Current Report on Form 8-K regarding the Convertible Promissory Note Offering is incorporated by reference into Section 2.03 of this Current Report on Form 8-K.

Section 3.02 Issuance of Unregistered titles

On October 4, 2022the board of directors of Gaucho Group Holdings, Inc. (the “Company”) has approved an offering of a series of 7% convertible promissory notes to accredited investors (the “Notes”) for a maximum amount of up to $689,000
(including principal and interest). The Notes mature one year from the date of issue, unless otherwise converted. Principal and accrued interest on the Notes will be converted into units (“Units”) consisting of one common share and one warrant to purchase one common share (the “Warrants”) at a conversion price equal to lesser of: (one) $0.21; and (b) the three-day volume-weighted average closing price (“VWAP”) of the common shares of the Company from the date that is two days prior to the mandatory conversion date (as defined below). ). The Notes will be compulsorily convertible on the earliest of the following dates (the “Mandatory Conversion Date”): (i) the date of execution of such ground lease to be executed pursuant to the previously announced agreement to develop a project in Las Vegas, Nevada, provided that such conversion will not result in the issuance of more than 6,563,389 common shares of the Company (including common shares issuable upon conversion of the warrants); and (b) the date on which the Company obtains shareholder approval to issue more than 6,563,389 common shares of the Company pursuant to Nasdaq Listing Rule 5635(d). The warrants may be exercised at the price of
$0.50 per share and have a duration of one year. The Company will receive a supplement $1,640,476 assuming the conversion of the Investor’s Notes at a price of $0.21 per Unit and the exercise of all Warrants.

From October 6, 2022the Company had issued convertible promissory notes in an aggregate principal amount of $92,000.

For this sale of securities, there will be no general solicitation and no commission will be paid, all purchasers must be accredited investors, and the Company is relying on the exemption from registration available under Section 4(a)(2) and/or Rule 506(b) of Regulation D promulgated under the Securities Act with respect to transactions by an issuer not involving a public offering.

Item 9.01 Financial statements and supporting documents.

(d) Exhibits

4.1     Form of Convertible Promissory Note
4.2     Form of Warrant
104   Cover Page Interactive Data File (embedded within the Inline XBRL document)

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