CONVERTIBLE DEBT OBLIGATIONS | 10. CONVERTIBLE DEBT OBLIGATIONS Amounts owed pursuant to the Company’s convertible debt obligations are as follows: SCHEDULE OF CONVERTIBLE NOTES GGH 2023 Total Debt Convertible debt, Balance at January 1, 2023 $ 1,997,909 $ - $ 1,997,909 $ (6,450 ) $ 1,991,459 Notes issued - 5,617,978 5,617,978 (2,509,601 ) 3,108,377 Warrant modification in connection with Letter Agreement - - - (392,273 ) (392,273 ) Debt principal converted to common stock: (1,335,439 ) (1,082,771 ) (2,418,210 ) - (2,418,210 ) Principal repayments (662,470 ) (200,071 ) (862,541 ) - (862,541 ) Amortization of debt discount - - - 2,104,384 2,104,384 Balance at September 30, 2023 - 4,335,136 4,335,136 (803,940 ) 3,531,196 Less: current portion of convertible debt - 1,893,019 1,893,019 (351,057 ) 1,541,962 Equals: convertible debt, non-current $ - $ 2,442,117 $ 2,442,117 $ (452,883 ) $ 1,989,234 GGH Convertible Notes On February 2, 2023, the Company and the holders of the remaining GGH Notes entered into a fourth letter agreement (“Letter Agreement #4). Pursuant to Letter Agreement #4, the parties agreed to reduce the conversion price of the GGH Notes to the lower of: (i) the closing sale price on the trading day immediately preceding the conversion date; and (ii) the average closing sale price of the common stock for the five trading days immediately preceding the conversion date. Between February 3 and February 15, 2023, the holders elected to convert $ 1,571,553 1,335,439 124,049 112,065 83,333 14.50 24.00 On February 8, 2023, the Company and the holders of the remaining GGH Notes entered into a fifth letter agreement (“Letter Agreement #5). Pursuant to Letter Agreement #5, the parties agreed to extend the maturity date of the notes from February 9, 2023 to February 28, 2023. On February 20, 2023, the Company entered into another exchange agreement (the “Exchange Agreement #4”) with the remaining holders of the GGH Notes, pursuant to which warrants for the purchase up to an aggregate of 15,000 1.00 134,779 662,470 On February 21, 2023, the Company redeemed the remaining GGH Notes for $ 905,428 662,470 118,909 124,049 GAUCHO GROUP HOLDINGS, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS 2023 Convertible Note On February 21, 2023, the Company entered into a securities purchase agreement (the “SPA”) with an institutional investor, (the “Investor”) pursuant to which the Company received proceeds of $ 5,000,000 5,617,978 337,710 13.40 5 The Company incurred financing costs of $ 321,803 218,187 103,616 Upon the issuance of the 2023 Note, the Company recorded a debt discount at issuance in the aggregate amount $ 2,509,601 617,978 218,187 63,502 1,609,935 Pursuant to the SPA, the exercise price of certain warrants for the purchase of 6,250 210.00 4,381 60.00 10.00 63,502 The 2023 Note is convertible into shares of common stock of the Company at a conversion price equal to the lower of (i) $ 13.40 13.40 2.70 2.70 The 2023 Note matures on the first anniversary of the issuance date (the “Maturity Date”) and bears interest at a rate of 7 The 2023 Note is redeemable at the Company’s election, so long as the Company is not in default, at the greater of (a) 115 500,000 GAUCHO GROUP HOLDINGS, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS Upon an event of default on the 2023 Note, the Conversion Price is reduced to the lesser of (a) $13.40 (subject to adjustment as described above); (b) 80% of the volume-weighted average price on the day preceding receipt of the conversion notice; or (c) 80% of the average of the three lowest volume-weighted average prices over the fifteen trading days which precede receipt of the conversion notice, subject to a floor price of $ 2.70 The Event of Default Conversion Price represents a redemption feature, which was bifurcated from the debt host and recorded as a derivative liability. As of the date of issuance of the 2023 Note, management had estimated that the probability of an event of default was negligible; accordingly, the fair value of the derivative liability was de minimis at the date of issuance. Pursuant to the terms of the 2023 Note, the Company must pay, convert or redeem one quarter of the initial principal, plus any outstanding interest and make-whole amount by each three-month anniversary of the issuance date. On May 21, 2023, an Event of Default occurred with respect to the 2023 Note as a result of not making the required quarterly payment due on that date (the “May 2023 Default Event”). On August 11, 2023, the Company and the Investor entered into a letter agreement pursuant to which, among other things: (i) the Investor agreed to forbear from issuing an Event of Default Notice and Event of Default Redemption Notice; (ii) the requirement in the 2023 Note to pay interest monthly in cash is waived for payments due August 1, 2023 through December 31, 2023; (iii) the application of the default interest rate on the 2023 Note is waived for the period from May 21, 2023 through December 31, 2023, (iv) the requirement for the Company to prepay, redeem, or convert one quarter the initial principal owe on the 2023 Note, plus any outstanding interest and make-whole amount by each three-month anniversary of the issuance date.is waived through December 31, 2023; (v) the Company adjusted the exercise price of the 2023 Note Warrant from $ 13.40 4.50 4.50 392,273 During the second quarter of 2023, the Company made redemption payments in the aggregate amount of $ 246,186 200,070 14,005 32,094 During the nine months ended September 30, 2023, the Company issued 314,790 1,250,267 1,082,771 78,951 13,077 262,300 2.70 7.79 186,832 GAUCHO GROUP HOLDINGS, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS Derivative Liability The Event of Default Conversion Price represents a redemption feature, which was bifurcated from the 2023 Note host and recorded as a derivative liability. During the three and nine months ended September 30, 2023, the Company has recorded $ 95,727 2,236,844 The following table sets forth a summary of the changes in the fair value of the derivative liability that are measured at fair value on a recurring basis: SUMMARY OF THE CHANGES IN THE FAIR VALUE OF DERIVATIVE LIABILITIES Balance at January 1, 2023 $ - Fair value of derivative liability upon issuance of 2023 Notes - Add: change in fair value of derivative liability upon May 2023 Default Event 2,141,117 Add: fair value of derivative associated with convertible interest accrued during the period 95,727 Change in fair value of derivatives for the nine months ended September 20, 2023 2,236,844 Less: fair value of derivative associated with 2023 Note balances converted during the period (262,300 ) Balance at September 30, 2023 1,974,544 Less: current portion of derivative liability 846,424 Equals: derivative liability, non-current portion $ 1,128,120 Interest Expense on Convertible Debt Obligations The Company incurred total interest expense of approximately $ 1,118,849 123,000 2,671,922 1,533,000 Interest expense during the three months ended September 30, 2023 and 2022 consists of (i) approximately $ 93,496 105,000 7 1,025,353 17,000 Interest expense during the nine months ended September 30, 2023 and 2022 consists of (i) approximately $ 449,149 455,000 7 118,389 0 2,104,384 1,079,000 GAUCHO GROUP HOLDINGS, INC. AND SUBSIDIARIES NOTES TO CONDENSED CONSOLIDATED FINANCIAL STATEMENTS |