Financial Performance - The company reported a net loss of approximately $3.2 million for the three months ended September 30, 2024, compared to a net loss of $2.3 million for the same period in 2023, indicating a worsening financial performance [227]. - For the nine months ended September 30, 2024, the company reported a net loss of approximately $8.6 million, an improvement from a net loss of $10.0 million in the same period of 2023 [240]. - The company incurred net losses of approximately $8.5 million and $10.0 million for the nine months ended September 30, 2024 and 2023, respectively [262]. Revenue and Profit - Revenues from operations decreased by approximately $41,000 or 9%, totaling around $423,000 for the three months ended September 30, 2024, down from $464,000 in 2023 [228]. - Revenues for the nine months ended September 30, 2024, were approximately $1,437,000, reflecting a decrease of about $186,000 or 11% from $1,623,000 in 2023 [242]. - Gross profit for the three months ended September 30, 2024, was approximately $69,000, a decrease of about $74,000 from $143,000 in the same period of 2023 [229]. Expenses - Selling and marketing expenses significantly decreased by approximately $200,000 or 98%, totaling around $5,000 for the three months ended September 30, 2024, compared to $205,000 in 2023 [230]. - Selling and marketing expenses for the nine months ended September 30, 2024, were approximately $228,000, a decrease of about $425,000 or 65% from $653,000 in 2023 [244]. - General and administrative expenses increased by approximately $1,007,000 or 79%, reaching about $2,274,000 for the three months ended September 30, 2024, compared to $1,267,000 in 2023 [231]. - General and administrative expenses increased by approximately $1,959,000 or 41%, totaling approximately $6,694,000 for the nine months ended September 30, 2024, compared to $4,735,000 in 2023 [245]. Interest and Cash Flow - Interest expense decreased by approximately $947,000 or 82%, totaling around $210,000 for the three months ended September 30, 2024, compared to $1,157,000 in 2023 [236]. - Interest income decreased by $151,000 or 90%, amounting to approximately $17,000 for the nine months ended September 30, 2024, down from $168,000 in 2023 [249]. - Interest expense decreased by approximately $2,031,000 or 72%, totaling approximately $794,000 for the nine months ended September 30, 2024, compared to $2,824,000 in 2023 [250]. - Net cash used in operating activities was approximately $6,865,000 for the nine months ended September 30, 2024, compared to $4,984,000 in 2023 [259]. - Net cash provided by financing activities amounted to approximately $6,493,000 for the nine months ended September 30, 2024, compared to $5,529,000 in 2023 [261]. Other Financial Metrics - The company recorded a loss of approximately $566,000 due to the termination of a lease in Miami, Florida, during the three months ended September 30, 2024 [233]. - The company recorded a loss of approximately $566,000 upon the termination of the Miami Lease during the nine months ended September 30, 2024 [248]. - Gains from foreign currency remeasurement decreased by approximately $281,000 or 81%, totaling approximately $66,000 for the nine months ended September 30, 2024 [254]. - The company had a working capital deficiency of approximately $5,000,000 as of September 30, 2024 [256]. - Cash and cash equivalents were approximately $213,000 as of September 30, 2024, down from $428,000 at the end of 2023 [256].

Financial Performance - For the three months ended March 31, 2024, the company reported revenues of approximately $587,000, reflecting an increase of approximately $139,000 or 31% compared to $448,000 in the same period of 2023[145] - The gross profit for the three months ended March 31, 2024, was approximately $220,000, an increase of approximately $66,000 from $154,000 in the same period of 2023[146] - Selling and marketing expenses decreased by approximately $139,000 or 59%, totaling approximately $96,000 for the three months ended March 31, 2024, compared to $235,000 in 2023[147] - General and administrative expenses increased by approximately $508,000 or 29%, amounting to approximately $2,265,000 for the three months ended March 31, 2024, compared to $1,757,000 in 2023[148] - The company recorded a net loss of approximately $2.7 million for both the three months ended March 31, 2024, and 2023[144] Cash Flow and Liquidity - Cash on hand as of March 31, 2024, was approximately $255,000, down from $428,000 as of December 31, 2023[156] - The working capital deficiency increased to approximately $6,065,000 as of March 31, 2024, compared to $5,363,000 as of December 31, 2023[156] - Net cash used in operating activities for the three months ended March 31, 2024, was approximately $2,092,000, compared to $2,939,000 in the same period of 2023[158] - For the three months ended March 31, 2024, net cash provided by financing activities was approximately $2,000,000, a decrease from $5,119,000 in the same period of 2023[161] Debt and Financing - The company issued 305,491 shares of common stock at $6.00 per share, raising aggregate gross proceeds of $1,832,934 during the period from January 1, 2024, through April 11, 2024[135] - The company has received multiple Event of Default Redemption Notices demanding immediate payment of principal and interest totaling a minimum of $3,460,510 related to the 2023 Convertible Note[138] - The company issued promissory notes totaling $1,185,000 in May 2024, with $925,000 issued for cash and an interest rate of 8.5% per annum[163] - Approximately $3.4 million in convertible debt is past due and payable upon demand as of March 31, 2024[162] - The company has been primarily funded through equity and debt financings since inception[164] - The company continues to evaluate additional financing opportunities but there is no assurance of obtaining funds on commercially acceptable terms[164] Going Concern - The company believes it may not have sufficient funds to operate for the next twelve months, raising substantial doubt about its ability to continue as a going concern[164] - Additional capital is needed to meet future liquidity needs for operating expenses and capital expenditures, including GGI inventory production and e-commerce platform development[165] Off-Balance Sheet Arrangements - There are no off-balance sheet arrangements reported by the company[166]

Financial Activities - The company raised gross proceeds of $937,146 through the Common Stock Purchase Agreement and issued 151,684 shares of common stock[25]. - The company entered into a promissory note for gross proceeds of $185,000 with an interest rate of 8% per annum, maturing on January 9, 2024[25]. - The company converted $1,571,553 in principal and interest into 83,333 shares of common stock at prices ranging from $14.50 to $24.00 per share[25]. - The company issued 59,100 shares of common stock for gross proceeds of $591,000 and warrants to purchase 14,775 shares at an exercise price of $10.00 per share[25]. - The company raised a total of $405,000 through a private placement at $4.50 per unit, issuing 90,000 shares of common stock and warrants[26]. - The company announced a private placement for gross proceeds of up to $4,000,000 at a price per share not lower than $0.60[28]. - On February 29, 2024, stockholders approved the issuance of shares for a private placement with gross proceeds of up to $7.2 million[29]. - The Company received Event of Default Redemption Notices from 3i demanding immediate payments totaling a minimum of $3,450,711[29]. - The termination of the 2022 ELOC by Tumim Stone Capital LLC has resulted in the loss of access to a line of credit of approximately $43,370,000, impacting the Company's ability to operate[162]. - The Company has generated significant operating losses, with revenues insufficient to cover operating expenses, putting a strain on working capital[164]. Compliance and Regulatory Issues - The company received a deficiency letter from Nasdaq for trading below the minimum $1.00 per share requirement, with a compliance deadline of November 28, 2023[26]. - The company is addressing compliance issues with Nasdaq by filing necessary reports and has received a deficiency letter for late filings[29]. - The company is currently in default under its convertible promissory note with 3i, with a demand for immediate payment of at least $3,460,510 due to failure to convert a portion of the 2023 Note into common stock[161]. - A reverse stock split may be implemented to regain compliance with Nasdaq's Bid Price Requirement, pending stockholder approval[154]. - The company is subject to the Inflation Reduction Act of 2022, which may impose a 15% minimum tax on book income for corporations with a 3-year average adjusted book income over $1 billion[172]. Business Strategy and Growth Plans - Gaucho Group Holdings aims to become the LVMH of South America, focusing on scalability and diversification of assets[32]. - The Gaucho – Buenos Aires™ brand is positioned to grow its e-commerce business, emphasizing luxury leather goods and accessories[37]. - The Company plans to introduce new products, including fragrances and a Gaucho Kids clothing line, in the next 18 months[43]. - GGH aims to develop a multi-billion-dollar brand, positioning Gaucho as "the Spirit of Argentina" and leveraging e-commerce for significant scale[80]. - GGH is implementing a growth strategy that includes luxury boutique hotels, high-end fashion, and large land development projects[79]. - The company is pursuing a roll-up strategy to acquire complementary businesses within the luxury sector, aiming to become the LVMH of South America[81]. Market and Economic Conditions - The Argentine economy has experienced a 2.5% decrease in GDP in 2023, with inflation estimated at approximately 135.7% for the same year[177][179]. - The Argentine peso has significantly devalued from about 6.1 pesos per dollar in December 2013 to approximately 276.2 pesos per dollar in February 2024[181]. - The Argentine government has enacted strict foreign exchange controls, limiting the ability of citizens and companies to access U.S. dollars, which has adversely affected purchasing power and could harm business operations[192]. - Argentina's ability to obtain financing from international markets is limited, which may impair its capacity to implement reforms and foster economic growth, adversely affecting the company's operations[196]. - The Argentine economy is susceptible to global market developments, with potential negative impacts from rising interest rates in developed economies affecting borrowing costs and economic growth[213]. Real Estate and Asset Management - Gaucho Group Holdings operates a vineyard and winery, alongside a hotel and resort in Argentina, enhancing its real estate portfolio[31]. - The company has invested in two ALGODON® brand properties: Algodon Mansion, a luxury boutique hotel in Buenos Aires, and Algodon Wine Estates, a winery and golf resort in Mendoza[99]. - Algodon Wine Estates has acquired 4,138 acres of contiguous real estate in Mendoza, Argentina, aimed at developing a vineyard-resort[123]. - The estate's master plan includes a luxury golf and vineyard living community with 610 home sites ranging from 0.2 to 2.8 hectares[124]. - The company is exploring licensing opportunities for its brand in commercial and residential real estate developments, similar to partnerships with luxury brands[84]. Operational Challenges - The Company may not be able to continue as a going concern without obtaining additional sources of capital, which could lead to curtailing operations[168]. - The Company is facing significant cost inflation, particularly in raw materials and supply chain costs, which may adversely affect its business operations[170]. - The company faces challenges in retaining qualified employees in Argentina due to economic instability and labor unrest, which could impact operational efficiency[195]. - There have been nationwide strikes in Argentina due to inadequate wages and benefits amid high inflation, which could lead to further government intervention[215]. - Energy supply restrictions in Argentina could negatively impact the economy, with a lack of investment in gas and electricity supply and transport capacity[216]. Marketing and Brand Development - The company targets upper and upper-middle class millennials in urban areas of the U.S. and Europe, who are willing to spend on "affordable luxury" items[51]. - The U.S.-based e-commerce website aims to deliver Argentine luxury goods globally, leveraging the favorable exchange rate due to the devaluation of the Argentine peso[49]. - Gaucho - Buenos Aires plans to expand its marketing strategy through SEO, social media, and partnerships with influencers to increase brand awareness[56]. - The company has received positive press coverage, including features in Marie Claire Argentina and Vogue Italia, highlighting its potential in the global fashion scene[63]. - The company anticipates opening pop-up shops in major U.S. cities to enhance brand visibility and customer engagement[60].

Financial Performance - For the three months ended September 30, 2023, the company reported a net loss of approximately $2.3 million, compared to a net loss of $4.7 million for the same period in 2022, reflecting an improvement of 51%[167]. - For the nine months ended September 30, 2023, the company reported a net loss of approximately $10.0 million, an improvement from a net loss of $12.3 million for the same period in 2022[179]. - The company incurred net losses of approximately $10.0 million for the nine months ended September 30, 2023, compared to $12.3 million in 2022[199]. Revenue and Profitability - Revenues from operations increased to approximately $464,000 for the three months ended September 30, 2023, up 5% from $441,000 in the same period of 2022, driven by increases in hotel, restaurant, and wine revenues[168]. - Revenues for the nine months ended September 30, 2023, were approximately $1,623,000, reflecting a 28% increase from $1,272,000 in 2022, driven by hotel, restaurant, and wine revenues[180]. - Gross profit for the three months ended September 30, 2023, was approximately $143,000, a significant increase from $7,000 in the same period of 2022, representing a growth of approximately 1943%[169]. - Gross profit for the nine months ended September 30, 2023, was approximately $340,000, a 415% increase from $66,000 in the same period of 2022[181]. Expenses - Selling and marketing expenses rose to approximately $205,000 for the three months ended September 30, 2023, an increase of 88% compared to $109,000 in 2022[170]. - General and administrative expenses decreased by approximately 27% to $1,267,000 for the three months ended September 30, 2023, down from $1,729,000 in 2022[171]. - General and administrative expenses for the nine months ended September 30, 2023, were approximately $4,735,000, a decrease of 12% from $5,403,000 in 2022[184]. - Interest expense surged to approximately $1,157,000 for the three months ended September 30, 2023, representing a 577% increase from $171,000 in the same period of 2022, primarily due to convertible debt issued[174]. - Interest expense increased by approximately $1,201,000 or 74% to $2,824,000 for the nine months ended September 30, 2023, compared to $1,624,000 in 2022, primarily due to a rise in interest and debt discount related to convertible debt issued in February 2023[188]. - Depreciation and amortization expense increased by approximately $149,000 or 83% to $328,000 for the nine months ended September 30, 2023, compared to $179,000 in 2022, due to new asset purchases[185]. Cash Flow and Liquidity - Net cash used in operating activities was approximately $4,984,000 for the nine months ended September 30, 2023, compared to $4,484,000 in 2022, attributed to a net loss of approximately $9,976,000 adjusted for non-cash expenses[195]. - Net cash provided by financing activities increased to approximately $5,529,000 for the nine months ended September 30, 2023, compared to $2,150,000 in 2022, resulting from net proceeds from debt issuance and common stock[198]. - Cash used in investing activities decreased to approximately $630,000 for the nine months ended September 30, 2023, from $1,959,000 in 2022, primarily due to reduced purchases of property and equipment[196]. - As of September 30, 2023, the company had cash of approximately $201,108 and a working capital deficit of approximately $1,128,750[193]. - The company has approximately $1.9 million in convertible debt obligations maturing on February 21, 2024, which raises concerns about future liquidity[199]. - The company plans to raise additional capital to meet future liquidity needs for operating expenses and capital expenditures, including GGI inventory production and e-commerce platform development[201].

[PART I - FINANCIAL INFORMATION](index=3&type=section&id=PART%20I%20-%20FINANCIAL%20INFORMATION) [Financial Statements](index=3&type=section&id=ITEM%201.%20Financial%20Statements) This section presents the unaudited condensed consolidated financial statements, highlighting increased assets, rising liabilities from new convertible debt, and persistent net losses [Condensed Consolidated Balance Sheets](index=3&type=section&id=Condensed%20Consolidated%20Balance%20Sheets) Total assets increased to $19.2 million, while total liabilities surged to $10.9 million due to new convertible debt, resulting in a working capital deficit Condensed Consolidated Balance Sheet Highlights (in thousands) | Balance Sheet Item | June 30, 2023 (unaudited) | December 31, 2022 | | :--- | :--- | :--- | | **Assets** | | | | Total Current Assets | $5,504 | $5,019 | | Total Assets | $19,219 | $18,693 | | **Liabilities & Equity** | | | | Total Current Liabilities | $9,332 | $4,424 | | Total Liabilities | $10,854 | $7,901 | | Total Stockholders' Equity | $8,365 | $10,792 | - Current liabilities more than doubled, driven by **$3.4 million** in current convertible debt obligations and a **$2.1 million** derivative liability, which were not present at year-end 2022[14](index=14&type=chunk) [Condensed Consolidated Statements of Operations](index=5&type=section&id=Condensed%20Consolidated%20Statements%20of%20Operations) Sales increased significantly for both the three and six-month periods, but a substantial derivative liability charge led to persistent net losses Statement of Operations Summary (in thousands, except per share data) | Metric | Q2 2023 | Q2 2022 | Change | H1 2023 | H1 2022 | Change | | :--- | :--- | :--- | :--- | :--- | :--- | :--- | | Sales | $711 | $405 | +75.6% | $1,159 | $831 | +39.5% | | Gross Profit (Loss) | $42 | $(128) | N/A | $197 | $59 | +233.9% | | Loss from Operations | $(1,986) | $(2,439) | -18.6% | $(3,932) | $(4,215) | -6.7% | | Net Loss | $(4,982) | $(5,293) | -5.9% | $(7,677) | $(7,565) | +1.5% | | Net Loss per Share | $(0.80) | $(4.80) | N/A | $(1.41) | $(7.59) | N/A | - A significant non-cash expense of **$2,141,117** related to the change in fair value of a derivative liability was recorded in Q2 2023, heavily impacting the net loss[17](index=17&type=chunk) [Condensed Consolidated Statements of Cash Flows](index=10&type=section&id=Condensed%20Consolidated%20Statements%20of%20Cash%20Flows) Net cash used in operations increased, while financing activities, primarily from convertible debt, significantly boosted cash provided, resulting in a net cash increase Cash Flow Summary for the Six Months Ended June 30 (in thousands) | Cash Flow Activity | 2023 | 2022 | | :--- | :--- | :--- | | Net Cash Used in Operating Activities | $(4,033) | $(2,755) | | Net Cash Used in Investing Activities | $(489) | $(1,720) | | Net Cash Provided by Financing Activities | $5,110 | $458 | | **Net Increase (Decrease) in Cash** | **$510** | **$(3,395)** | - The company's operations were heavily funded by financing activities in the first half of 2023, with **$5.0 million** in proceeds from new convertible debt and over **$1.3 million** from stock sales[32](index=32&type=chunk) [Notes to Financial Statements](index=12&type=section&id=Notes%20to%20Unaudited%20Condensed%20Consolidated%20Financial%20Statements) Notes detail accounting policies, business segments, and financial instruments, including a 'going concern' warning, revenue breakdowns, and convertible debt specifics - The company's financial statements are prepared on a going concern basis, but management has **substantial doubt** about its ability to continue for one year due to recurring net losses, a working capital deficit, and upcoming debt maturities[41](index=41&type=chunk)[42](index=42&type=chunk)[45](index=45&type=chunk) Revenue by Source for the Six Months Ended June 30 (in thousands) | Revenue Source | 2023 | 2022 | | :--- | :--- | :--- | | Real estate sales | $155 | $185 | | Hotel rooms and events | $465 | $283 | | Restaurants | $136 | $58 | | Winemaking | $76 | $60 | | Agricultural | $163 | $181 | | Clothes and accessories | $108 | $11 | | **Total Revenues** | **$1,159** | **$831** | - In February 2023, the company issued a **$5.6 million** senior secured convertible note, and as of June 30, 2023, the company was in **default** on this note, triggering a remeasurement of a derivative liability and a **$2.1 million loss**[92](index=92&type=chunk)[101](index=101&type=chunk) - Subsequent to the quarter's end, on August 11, 2023, the company entered into a **forbearance agreement** with the 2023 Note holder, **waiving the default** and certain payment requirements through December 31, 2023[143](index=143&type=chunk) [Management's Discussion and Analysis (MD&A)](index=32&type=section&id=ITEM%202.%20Management%27s%20Discussion%20and%20Analysis%20of%20Financial%20Condition%20and%20Results%20of%20Operations) Management discusses financial performance, highlighting increased revenues, persistent net losses, and expresses substantial doubt about the company's ability to continue as a going concern - The company's goal is to become recognized as the **'LVMH of South America's leading luxury brands,'** focusing on its e-commerce fashion brand Gaucho – Buenos Aires™ and legacy investments in hospitality and wine[147](index=147&type=chunk)[148](index=148&type=chunk) Results of Operations Comparison (Q2 2023 vs Q2 2022) | Metric | Q2 2023 | Q2 2022 | Change | Reason for Change | | :--- | :--- | :--- | :--- | :--- | | Revenues | $711k | $405k | +76% | Increased tourism, Miami store opening, partially offset by peso devaluation | | Gross Profit (Loss) | $42k | ($128k) | +133% | Profits from real estate lot sales | | G&A Expenses | $1.71M | $1.93M | -11% | Lower compensation and favorable currency impact, offset by higher consulting fees | | Net Loss | ($5.0M) | ($5.3M) | -6% | Improved operations offset by a $2.1M derivative liability charge | - The company has a **working capital deficit of $3.8 million** as of June 30, 2023, a sharp decline from a **working capital surplus of $0.6 million** at the end of 2022[185](index=185&type=chunk) - Management states there is **substantial doubt** about the company's ability to continue as a **going concern**, as it may not have sufficient funds to operate for the next twelve months without raising additional capital[192](index=192&type=chunk) [Quantitative and Qualitative Disclosures About Market Risk](index=39&type=section&id=ITEM%203.%20Quantitative%20and%20Qualitative%20Disclosures%20About%20Market%20Risk) As a smaller reporting company, Gaucho Group Holdings, Inc. is not required to provide market risk disclosures - The company has **opted out** of providing disclosures about market risk, as permitted for a **'smaller reporting company'**[200](index=200&type=chunk) [Controls and Procedures](index=39&type=section&id=ITEM%204.%20Controls%20and%20Procedures) Management concluded that disclosure controls and procedures were ineffective due to a lack of segregation of duties and insufficient testing - The Principal Executive Officer and Principal Financial Officer concluded that disclosure controls and procedures were **not effective** as of June 30, 2023[201](index=201&type=chunk) - The ineffectiveness is attributed to a **lack of segregation of duties** due to the company's small size and **insufficient testing** of control effectiveness[201](index=201&type=chunk) [PART II - OTHER INFORMATION](index=41&type=section&id=PART%20II%20-%20OTHER%20INFORMATION) [Legal Proceedings](index=41&type=section&id=ITEM%201.%20Legal%20Proceedings) The company is not currently involved in any litigation expected to have a material adverse effect on its financial condition or operations - The company is **not involved** in any litigation expected to have a **material adverse effect**[207](index=207&type=chunk) [Risk Factors](index=41&type=section&id=ITEM%201A.%20Risk%20Factors) Significant risks include potential Nasdaq delisting, default on a convertible note, and the risk of total loss for the LVH Las Vegas project investment - The company received a **deficiency notice** from Nasdaq on June 1, 2023, for its stock trading **below the $1.00 minimum bid price** requirement and has until November 28, 2023, to regain compliance[210](index=210&type=chunk) - The company is **in default** on its 2023 convertible note for failure to meet a payment/conversion milestone, though a **forbearance agreement** is in place until December 31, 2023[215](index=215&type=chunk) - The company's **$7.0 million investment is at risk** in the LVH Las Vegas project, as LVH will be **liquidated** if a ground lease is not executed by December 29, 2023, which could result in the **loss of the entire investment**[216](index=216&type=chunk)[217](index=217&type=chunk) [Unregistered Sales of Equity Securities and Use of Proceeds](index=43&type=section&id=ITEM%202.%20Unregistered%20Sales%20of%20Equity%20Securities%20and%20Use%20of%20Proceeds) In Q2 2023, the company issued **458,768 shares** under an Equity Line of Credit, raising **$316,953** through unregistered offerings - In Q2 2023, the company issued **458,768 shares** for gross proceeds of **$316,953** via its equity line of credit with Tumim Capital[219](index=219&type=chunk) [Defaults Upon Senior Securities](index=43&type=section&id=ITEM%203.%20Defaults%20Upon%20Senior%20Securities) The company **defaulted** on its 2023 senior secured convertible note, but a **forbearance agreement** was reached, deferring action until December 31, 2023 - The company **defaulted** on its 2023 convertible note as of May 21, 2023[220](index=220&type=chunk) - A **forbearance agreement** was reached with the noteholder on August 11, 2023, **preventing an event of default** notice through December 31, 2023[220](index=220&type=chunk) [Mine Safety Disclosures](index=43&type=section&id=ITEM%204.%20Mine%20Safety%20Disclosures) This item is not applicable to the company - Not applicable[221](index=221&type=chunk) [Other Information](index=43&type=section&id=ITEM%205.%20Other%20Information) This section details corporate actions including shareholder approval for a reverse stock split, an extended LVH ground lease deadline, and a forbearance agreement with warrant price adjustment - The company is seeking shareholder approval for a **reverse stock split** (from 1-for-2 up to 1-for-10) to **regain compliance with Nasdaq's minimum bid price rule**[223](index=223&type=chunk) - The deadline for the LVH Holdings LLC project to execute a ground lease was **extended** from June 30, 2023, to December 29, 2023[225](index=225&type=chunk) - As part of the August 11, 2023 **forbearance agreement**, the exercise price of the warrant associated with the 2023 Note was **reduced from $1.34 to $0.45**[231](index=231&type=chunk) [Exhibits](index=45&type=section&id=ITEM%206.%20Exhibits) This section lists all exhibits filed with the Form 10-Q, including various agreements, certifications, and interactive data files - Lists all exhibits filed with the report, including underwriting agreements, incentive plans, debt agreements, and officer certifications[235](index=235&type=chunk)

As filed with the Securities and Exchange Commission on May 22, 2023 Registration No. 333-271761 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 1 to FORM S-1 Delaware 6552 52-2158952 (State or other jurisdiction of incorporation or organization) (Primary Standard Industrial Classification Code Number) (I.R.S. Employer Identification No.) 112 NE 41st Street, Suite 106, Miami, Florida 33137 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Gaucho Group Holdings, In ...

Financial Performance - For the three months ended March 31, 2023, the company reported a net loss of approximately $2.7 million, compared to a net loss of $2.3 million for the same period in 2022 [142]. - Revenues from operations increased by approximately $22,000 or 5%, totaling approximately $448,000 for Q1 2023, driven by increases in hotel, restaurant, and wine revenues [143]. - Gross profit decreased by approximately $33,000 or 18%, amounting to approximately $154,000 for Q1 2023 [144]. - Cost of sales increased by approximately $55,000 or 23%, reaching approximately $293,000 for Q1 2023, primarily due to higher hotel, restaurant, and wine costs [145]. - Selling and marketing expenses rose by approximately $63,000 or 37%, totaling approximately $235,000 for Q1 2023, mainly due to advertising and marketing for new retail space [146]. - General and administrative expenses increased by approximately $12,000 or 1%, amounting to approximately $1,757,000 for Q1 2023 [147]. Cash Flow and Liquidity - Cash as of March 31, 2023, was approximately $2.39 million, a significant increase from $300,185 as of December 31, 2022 [156]. - Net cash used in operating activities for Q1 2023 was approximately $2.94 million, compared to $2.10 million for Q1 2022 [158]. - As of March 31, 2023, the Company had cash of approximately $2,390,000 and working capital of $361,000 [162]. - The Company used cash in operating activities of approximately $2,939,000 during the three months ended March 31, 2023, compared to $2,099,000 in the prior year [162]. - The Company funded its operations with $5,000,000 from convertible debt financing, approximately $441,000 from equity line of credit draws, and $591,000 from common stock sales during the three months ended March 31, 2023 [162]. - The Company believes it may not have sufficient funds to operate for the next twelve months, raising substantial doubt about its ability to continue as a going concern [163]. - Additional capital will be needed to meet future liquidity needs for operating expenses and capital expenditures, including GGI inventory production and e-commerce platform development [164]. Accounting Policies and Derivatives - The Company has no off-balance sheet arrangements [165]. - There are no material changes in critical accounting policies from the previous annual report [167]. - The Company has adopted a sequencing policy for the reclassification of contracts from equity to assets or liabilities under ASC 815 [169]. - Derivative instruments are evaluated at the end of each reporting period, with changes in fair value reported in the consolidated statements of operations [170].

As filed with the Securities and Exchange Commission on May 9, 2023 Registration No. __________ UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Gaucho Group Holdings, Inc. Delaware 6552 52-2158952 (State or other jurisdiction of incorporation or organization) (Primary Standard Industrial Classification Code Number) (I.R.S. Employer Identification No.) 112 NE 41st Street, Suite 106, Miami, Florida 33137 (Address, includi ...

As filed with the Securities and Exchange Commission on April 17, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Gaucho Group Holdings, Inc. Delaware 6552 52-2158952 (State or other jurisdiction of incorporation or organization) (Primary Standard Industrial Classification Code Number) Registration No. __________ (I.R.S. Employer Identification No.) 112 NE 41st Street, Suite 106, Miami, Florida 33137 (Address, incl ...

Acquisitions and Investments - The company acquired 100% of Hollywood Burger Argentina S.R.L. for 106,952 shares of common stock[22] - The company completed the acquisition of the domain name Gaucho.com for $34,999 and 1,250 shares of common stock[22] - The company is pursuing a roll-up strategy to acquire complementary businesses in high-end fashion and luxury products, leveraging its Nasdaq listing for potential acquisitions[82] - The company has invested in two key properties: Algodon Mansion in Buenos Aires and Algodon Wine Estates in Mendoza, focusing on luxury hospitality and wine production[100] - Algodon Wine Estates has acquired a total of 4,138 acres of contiguous real estate in Mendoza, Argentina, aimed at developing a vineyard-resort and attracting investment for luxury residential homes[126] Financial Performance and Market Strategy - The company issued 1,666,667 shares pursuant to the 2021 Securities Purchase Agreement to comply with Nasdaq Exchange Cap rules[24] - The company entered into a Securities Purchase Agreement for senior secured convertible notes totaling $5,617,978, receiving $5,000,000 in proceeds after an 11% original issue discount[25] - The company has generated significant operating losses, which have strained working capital and delayed profitability expectations[163] - The company may not be able to generate sufficient cash flows from operations to satisfy its debt service requirements, impacting its ability to refinance or obtain future financing[165] - The company anticipates utilizing digital marketing strategies, including SEO and social media campaigns, to enhance brand awareness and drive sales[54] Product Development and Brand Expansion - The company debuted its home goods line, Gaucho Casa, on April 14, 2022, expanding its product offerings[23] - In Q1 2022, Gaucho launched its home and living décor collection, Gaucho Casa, which features luxury textiles and home accessories[39] - The company plans to introduce new products, including fragrances and a Gaucho Kids clothing line, within the next 18 months[39] - Gaucho Casa, a home & living décor brand, is positioned to challenge traditional lifestyle collections with luxury textiles and home accessories, emphasizing eco-friendly materials[87][88] - The company envisions launching a designer baby and kids' clothing collection, aiming to cater to parents who appreciate luxury and creativity in children's fashion[91] Market Presence and Target Audience - Gaucho – Buenos Aires targets upper and upper-middle class millennials in urban areas of the U.S. and Europe, capitalizing on their willingness to spend on "affordable luxury" items[49] - The brand aims to fill the void left by international fashion chains in Argentina, positioning itself as a leading fashion and leather accessories brand from South America[45] - The company is expanding its market presence through popup shops in major U.S. cities, enhancing brand awareness and customer engagement[93] - Gaucho – Buenos Aires plans to explore both online and brick-and-mortar retail opportunities, including partnerships with high-end boutiques[56] - The e-commerce platform Gaucho – Buenos Aires is designed to process and fulfill orders internationally, aiming for significant scale and value addition[33] Economic and Operational Challenges - The company has faced significant cost inflation, particularly in raw materials and supply chain costs, exacerbated by geopolitical events such as the 2022 Russian invasion of Ukraine[160] - The Argentine economy has experienced high inflation, with an estimated inflation rate of approximately 95% for 2022 and a forecasted increase to about 60% in 2023[180] - Labor unrest and high inflation have created challenges in retaining qualified employees, impacting the company's operational efficiency in Argentina[197] - The Argentine banking system's stability is uncertain, with potential liquidity issues arising from adverse economic developments and depositor confidence crises[210] - The Argentine government may implement measures such as expropriation, nationalization, and new taxation policies, which could adversely affect the economy and the company's business[214] Hospitality and Real Estate Performance - The occupancy level at Algodon Mansion increased from 29% in 2021 to 50% in 2022, representing a 72% increase, attributed to the reopening of international borders post-COVID[102] - The average daily rate (ADR) at Algodon Mansion rose from USD 234 in 2021 to USD 261 in 2022, a 12% increase, while in ARS, it increased by 51% due to peso devaluation[105] - Revenue per available room (RevPAR) at Algodon Mansion surged from USD 69 in 2021 to USD 130 in 2022, an 88% increase, with a 156% increase in ARS[106] - Algodon Wine Estates experienced a decrease in occupancy from 56% in 2021 to 41% in 2022, a 27% decline, due to reduced subsidies from Argentina's Ministry of Tourism[111] - The company is currently marketing portions of the property for luxury residential homes, with a master plan featuring 610 home sites ranging from 0.2 to 2.8 hectares[128] Regulatory and Compliance Issues - The Company received a deficiency letter from Nasdaq on July 14, 2022, indicating that its common stock was trading below the minimum $1.00 per share requirement for continued inclusion[153] - A reverse stock split was executed on November 4, 2022, at a ratio of 1 share for every 12 shares previously issued[154] - The Company regained compliance with Nasdaq's minimum bid price requirements on November 21, 2022[155] - The Company is subject to the Inflation Reduction Act of 2022, which includes a 15% minimum tax on corporations with a 3-year average adjusted book income over $1 billion[162] - The ongoing COVID-19 pandemic has caused significant delays in product development and fulfillment, leading to reduced web traffic and sales[173]