CONVERTIBLE DEBT OBLIGATIONS | 14. CONVERTIBLE DEBT OBLIGATIONS Activity related to the Company’s convertible debt obligations is as follows: SCHEDULE OF CONVERTIBLE NOTES GGH Notes Investor Notes October Notes 2023 Note Total Principal Debt Discount net of discount Convertible debt, GGH Notes Investor Notes October Notes 2023 Note Total Principal Debt Discount net of discount Balance at January 1, 2022 $ 6,480,000 $ - $ - $ - $ 6,480,000 $ (751,652 ) $ 5,728,348 Notes issued - 1,727,500 1,431,500 - 3,159,000 - 3,159,000 Note principal exchanged for warrants (900 ) - - - (900 ) (848,531 ) (849,431 ) Debt principal converted to common stock (4,481,191 ) (1,727,500 ) (1,431,500 ) - (7,640,191 ) - (7,640,191 ) Amortization of debt discount - - - - - 1,172,461 1,172,461 Extinguishment loss - - - - - 421,272 421,272 Balance at December 31, 2022 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 - - - - - (392,273 ) (392,273 ) Debt principal converted to common stock (1,335,439 ) - - (3,822,210 ) (5,157,649 ) - (5,157,649 ) Principal repayments (662,470 ) - - (200,071 ) (862,541 ) - (862,541 ) Amortization of debt discount - - - - - 2,633,529 2,633,529 Balance at December 31, 2023 $ - $ - $ - $ 1,595,697 $ 1,595,697 $ (274,795 ) $ 1,320,902 GGH Convertible Notes On November 3, 2021, the Company sold senior secured convertible notes of the Company, in the aggregate original principal amount of $ 6,480,000 6,000,000 7 420.00 4.99% GAUCHO GROUP HOLDINGS, INC. AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS The GGH Notes ranked senior to all outstanding and future indebtedness of the Company and its subsidiaries and were secured by all existing and future assets of the Company, as well as shares of common stock and certain options to purchase common stock of the Company owned by the President and CEO of the Company. Holders of GGH Notes were entitled to certain registration rights, pursuant to a registration rights agreement between the holders of the GGH Notes and the Company, dated November 9, 2021. Upon the issuance of the GGH Notes, the Company recorded a debt discount at issuance in the aggregate amount $ 950,813 480,000 470,813 The GGH Notes included several embedded features that require bifurcation. However, management has determined that the value of these bifurcated derivatives was de minimis as of November 3, 2021 (date of the agreement) and December 31, 2022. Pursuant to the original terms of the GGH Notes, beginning on February 7, 2022, the Company was to make nine monthly payments consisting of principal in the amount of $ 720,000 On February 22, 2022, the Company entered into an exchange agreement (the “Exchange Agreement”) with holders of GGH Notes. Pursuant to the Exchange Agreement, the Company was able to defer monthly principal payments until May 7, 2022 and make six monthly payments in the amount of $ 1,080,000 300 6,250 210.00 731,856 300 On May 2, 2022, the Company entered into a letter agreement with the holders of GGH Notes (the “Letter Agreement #1”). The Letter Agreement #1 provided for the reduction of the conversion price for shares of the Company’s common stock from $ 420.00 162.00 357,498 2,207 162.00 198,096 On May 12, 2022, the Company entered into a conversion agreement with the holders of GGH Notes (the “Letter Agreement #2”) pursuant to which the parties agreed to reduce the Conversion Price to $ 114.00 4.90% 2,105,119 421,272 1,683,847 1,165,099 10,220 114.00 4,968 5,252 GAUCHO GROUP HOLDINGS, INC. AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS The fair value of the modified debt instrument at the extinguishment date was determined to be $ 7,831,248 6,147,401 1,683,847 0.48 61 0 On July 1, 2022, the Company entered into another letter agreement with the holders of GGH Notes (the “Letter Agreement #3”). The Letter Agreement #3 provided for the reduction of the conversion price for shares of the Company’s common stock from $ 114.00 36.00 During the period from July 7 through August 30, 2022, GGH Notes with principal, interest and fees in the amount of $ 3,201,894 88,942 36.00 2,965,222 On September 22, 2022, the Company and the Holders of the GGH Notes entered into another exchange agreement (the “Exchange Agreement #2”) with the Holders in order to amend and waive certain provisions of the Existing Note Documents and exchange $ 300 9,092 38.20 102,167 300 On November 30, 2022, the Company and the Holders entered into another exchange agreement (the “Exchange Agreement #3”) with the Holders in order to amend and waive certain provisions of the Existing Note Documents and exchanged $ 300 4,381 24.00 4,381 60.00 15,108 300 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 an aggregate of $ 1,571,553 1,335,439 124,049 112,065 83,333 14.50 24.00 GAUCHO GROUP HOLDINGS, INC. AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 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 Investor Notes During the period from July 13, 2022 through August 30, 2022, the Company issued convertible promissory notes to certain investors (the “Investor Notes”) in the aggregate amount of $ 1,727,500 125,000 20 66.00 At the annual stockholder meeting held on August 30, 2022, the Company obtained the requisite stockholder approval, and the Investor Notes comprised of $ 1,727,500 8,252 45,459 38.20 38.20 GAUCHO GROUP HOLDINGS, INC. AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS October Notes On October 22, 2022, the Board of Directors approved an offering of up to $ 1.5 7 The October Notes were to be mandatorily converted upon the earlier to occur of: (i) the date of execution of a ground lease in connection with the previously announced agreement to develop a project in Las Vegas, Nevada (see Note 1 - Business Organization and Nature of Operations); or (ii) the date the Company obtains stockholder approval to issue shares of the Company’s common stock in accordance with Nasdaq Listing Rule 5635(d) (each, a “Mandatory Conversion Event”). Upon a Mandatory Conversion Event, the October Notes will be converted into units (“Units”), with each Unit consisting of one share of common stock and a one-year warrant for the purchase of one share of common stock, exercisable at $ 60.00 25.20 24.00 On December 19, 2022, at a special meeting of the stockholders of the Company, the stockholders approved, for purposes of complying with Nasdaq Listing Rule 5635(d), the issuance of up to 125,000 19.99 Also on December 19, 2022, October Notes representing a total of $ 1,431,500 13,817 60,223 24.00 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 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 GAUCHO GROUP HOLDINGS, INC. AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 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 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 4.99 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 Upon an event of default on the 2023 Note, the Conversion Price is reduced to the lesser of (a) $ 13.40 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. GAUCHO GROUP HOLDINGS, INC. AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 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 (18%) 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 owed on the 2023 Note, plus any outstanding interest and make-whole amount by each three-month anniversary of the issuance date was 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 Pursuant to the SPA and 2023 Note, on October 5, 2023, the Company and the Holder entered into the first amendment to 2023 Note which amends the 2023 Note and lowers the floor price for conversion of the 2023 Note from $ 2.70 0.40 During the year ended December 31, 2023, the Company made redemption payments in the aggregate amount of $ 246,186 200,071 14,004 32,111 During the year ended December 31, 2023, the Company issued 2,297,005 4,339,195 3,822,210 220,996 13,077 1,767,591 0.48 7.79 1,484,677 13,077 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 year ended December 31, 2023, the Company has recorded $ 2,505,731 GAUCHO GROUP HOLDINGS, INC. AND SUBSIDIARIES NOTES TO CONSOLIDATED FINANCIAL STATEMENTS 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 364,614 Less: fair value of derivative associated with 2023 Note balances converted during the period (1,767,591 ) Balance at December 31, 2023 $ 738,140 Interest Expense on Convertible Debt Obligations The Company incurred total interest expense of approximately $ 3,281,676 1,683,815 Interest expense during the year ended 2023 consisted of (i) $ 648,145 2,633,531 510,851 1,172,461 |