#1Oloverstock. Q2 2022 Earnings Call TM#2Forward-Looking Statements The information presented herein may contain forward-looking statements within the meaning of the federal securities laws. Such forward- looking statements include all statements other than statements of historical fact, including forecasts of trends, market conditions, and other factors that will impact our results of operations. You should not place undue reliance on any forward-looking statements, which speak only as of the date they were made. We undertake no obligation to update any forward-looking statements as a result of any new information, future developments, or otherwise. Forward-looking statements are inherently difficult to predict. Accordingly, actual results could differ materially for a variety of reasons, including but not limited to, macroeconomic changes, including higher inflation and rising interest rates, and difficulties we may have with our fulfillment partners, supply chain, access to products, shipping costs, competition, attraction/retention of employees, search engine optimization results, and/or payment processors. Other risks and uncertainties include, among others, the duration of the COVID-19 pandemic and its ultimate impact on our business and results of operations, global conflict including the current conflict between Russia and Ukraine and its related geopolitical impacts, problems with our infrastructure, including cyber-attacks or data breaches affecting us, adverse tax, regulatory or legal developments, any further restrictions on the use of "cookies" or other tracking technologies, any negative business impacts associated with our strategy to exit from non-home categories, and whether our partnership with Pelion Venture Partners will be able to achieve. its objectives. More information about factors that could potentially affect our financial results are included in our Form 10-K for the year ended December 31, 2021 which was filed with the SEC on February 25, 2022, our Form 10-Q for the quarter ended March 31, 2022 which was filed with the SEC on May 4, 2022, and in our subsequent filings with the SEC. The Form 10-K, Form 10-Q, and our subsequent filings with the SEC identify important factors that could cause our actual results to differ materially from those contained in or contemplated by our projections, estimates, and other forward-looking statements. overstock. 2#3Agenda overstock. 1. CEO Remarks 2. Financial Results 3. Business Updates 4. Summary and Q&A 3#4overstock. CEO Remarks +#5Q2 Revenue -A 3-year Look Back Revenue ($M) $800 $700 $600 $500 $400 $300 $200 $100 $0 overstock. $367 Q2 '19 2nd largest Q2 in history $767 Q2 '20 Largest Q2 in history $795 Q2 '21 +13% 3-yr CAGR +44% $528 Q2 '22 Note: All figures represent results from continuing operations. 1 Source: Insider Intelligence/eMarketer 2019 through 2022 estimates of total U.S. Furniture & Home Furnishings market size as of Jun 2022. Q2 Dynamics ■ Comparison to 2019 +44% growth Outpaced TAM expansion ¹ - Became profitable - 5#6Corporate Update ■ ■ ■ Executed share repurchases Simplified capital structure Transitioned to 100% home assortment overstock. 6#7overstock. Financial Results 7#8Q2 2022 Financial Results Revenue $528.1 Million -34% vs. Q2'21 Adjusted EBITDA Margin ¹ 3.9% -165 bps vs. Q2'21 overstock. Gross Margin 22.9% +93 bps vs. Q2'21 Diluted EPS $0.12 Adjusted Diluted EPS² $0.19 -$0.54 vs. Q2'21 G&A and Tech % of Revenue 9.8% +310 bps vs. Q2'21 Ending Cash $442.6 Million -10%/-$50.7M vs. Q1'22 Note: All figures represent results from continuing operations. 1 Adjusted EBITDA Margin is a non-GAAP financial measure. See reconciliation in appendix. 2 Includes adjustment related to non-cash dividend related to preferred share conversion and tax impact of equity method activity. See reconciliation in appendix. 8#9Revenue $800 $700 $600 $500 $400 $300 $200 $100 $0 Revenue ($M) $767 Q2 '20 overstock. $718 Q3 '20 $670 Q4 '20 $660 Q1 '21 $795 Q2 '21 Note: All figures represent results from continuing operations. $689 Q3 '21 $613 Q4 '21 -34% $536 Q1 '22 $528 Q2 '22 Q2 Dynamics ■ Revenue of $528.1M -34%/-$266M vs. Q2'21 Revenue influenced by: Macro / consumer sentiment Non-home category exit 2021 government stimulus 9#10Gross Margin $225 $200 $175 $150 $125 $100 $75 $50 $25 $0 Gross Margin ($M) 23.2% $178 Q2 '20 overstock. 23.5% $169 Q3 '20 22.5% $151 Q4 '20 23.3% $154 Q1 '21 22.0% $175 Q2 '21 Note: All figures represent results from continuing operations. 22.7% $157 Q3 '21 22.7% $139 Q4 '21 23.4% $125 Q1 '22 Gross Margin (%) 22.9% $121 Q2 '22 25% 20% 15% 10% 5% 0% Q2 Dynamics ■ Gross margin of 22.9% +93 bps vs. Q2'21 ▪ Gross margin influenced by: Operational efficiencies Offset by higher discounting 10#11G&A and Tech Expense $80 $70 $60 $50 $40 $30 $20 $10 $0 G&A and Tech Expense ($M) $57¹ 7.5% 6.5% Q2 '20 overstock. $59 8.2% $54 8.1% $53 8.1% $53 6.7% $52 Q2 '21 7.6% $52 Q3 '21 8.4% G&A and Tech Exp. as % of Revenue Q4 '21 $54 10.1% $52 9.8% Q1 '22 18% Q2 '22 16% 14% 12% 10% 8% Q3 '20 Q4 '20 Q1 '21 Note: All figures represent results from continuing operations. 1 In Q2'20 we recorded $7.3M in special items that benefited G&A expense. Reported G&A and tech expense in Q2'20 was $49.9M or 6.5% of revenue. 6% 4% 2% 0% Q2 Dynamics G&A and Tech Expense of $52M -3% vs. Q2'21 ■ ■ G&A and tech expense % of revenue of 9.8% +310 bps vs. Q2'21 11#12Adjusted EBITDA $60 $50 $40 $30 $20 $10 $0 Adjusted EBITDA ($M) $49 6.4% Q2 '20 overstock. $46 6.4% Q3 '20 $30 4.5% Q4 '20 $34 5.1% Q1 '21 $44 5.6% Q2 '21 Note: All figures represent results from continuing operations. $36 5.2% Q3 '21 $27 4.5% Q4 '21 Adjusted EBITDA Margin (%) $21 4.0% Q1 '22 $21 3.9% Q2 '22 12% 10% 8% 6% 4% 2% 0% Q2 Dynamics ■ - Adj. EBITDA of $21M -$24M vs. Q2'21 Adj. EBITDA margin of 3.9% -165 bps vs. Q2'21 12#13Active Customers and Order Frequency 12 10 8 6 2 0 Active Customers (LTM) (M) 1.62 7.0 Q2 '20 overstock. 1.63 8.2 1.64 9.2 1.66 9.9 1.69 9.2 1.68 8.7 Order per Active Customer (LTM) Q3'21 1.67 8.1 1.67 Q4 '21 7.4 Q3 '20 Q1 '21 Q2 '21 Q4 '20 Note: All figures represent results from continuing operations. Note: Orders per active customer represents the number of orders delivered over a twelve-month period divided by the number of active customers for that same period. 1.65 Q1 '22 6.5 Q2 '22 Q2 Dynamics ■ Active customers of 6.5M -29% / -2.7M vs. Q2'21 Macro / consumer sentiment Non-home category exit - Order frequency of 1.65 -2% vs. Q2'21 Improved home association 13#14Orders and Average Order Value 25 20 15 10 01 5 0 Orders Delivered (LTM) (M) $160 11.3 Q2 '20 overstock. $173 13.4 $168 15.1 $183 16.5 $213 15.5 $214 14.5 $206 13.5 Average Order Value $221 12.3 Q4 '20 Q1 '21 Q2 '21 Q3 '21 Q4 '21 Q1 '22 Q3 '20 Note: LTM orders delivered represents the total number of orders delivered during the prior twelve-month period. Note: Average order value represents net revenue divided by orders delivered, measured on a quarterly basis. $247 10.7 Q2 '22 $250 $200 $150 $100 $50 $0 Q2 Dynamics Orders delivered (LTM) of 10.7M -31% -4.8M vs. Q2'21 ■ ■ Average order value of $247 +16% vs. Q2'21 Sales mix within home categories 14#15Home-only Active Customers and Revenue Q2 LTM Active Customers Change Reported -29% YoY Excluding non-home only¹ customers -26% YoY ■ 0% H -5% -10% -15% -20% -25% -30% -35% -40% -8.8% -12.1% Q4 '21 overstock. [I -23.1% -25.6% Q1 '22 -26.1% -29.2% Q2 '22 Actual/ Reported Excluding non-home only customers Q2 Revenue Change Reported -34% YoY Excluding non-home only¹ customers -31% YoY ■ 0% H -5% -10% -15% -20% -25% -30% -35% -40% -8.5% -5.3% Q4 '21 -16.2% -18.8% Q1 '22 -33.5% -30.5% Q2 '22 Actual/ Reported Excluding non-home only customers 1 Non-home only customers represent customers who have only shopped non-home categories over the last twelve months. Home customers who also shopped non-home categories have not been excluded. 15#16Q2 2022 Balance Sheet & Cash Flow Highlights overstock. Cash $443 Million -10%/-$51M vs. Q1'22 Net Cash Position ¹ $406 Million -11% /-$50M vs. Q1'22 1 Cash less long-term debt. Long-term Debt $36 Million -2% -$1 M vs. Q1'22 No significant debt maturity until March 2030 Share Repurchases YTD $60 Million +39% / +$35M vs. Q1'22 Includes FY 2022 repurchases through Q2 2022 16#17overstock. Business Updates m 17#18Top 4 Brand in a Growing $419B Market' Top U.S. Home Furnishings Online Brands² (ranked by online revenue) 1. Amazon 2. Wayfair 3. Walmart 4. 5. Target 6. Pottery Barn IKEA Bed Bath & Beyond West Elm 1. loverstock 8. 9. 10. Restoration Hardware overstock. 40% 30% 20% 10% 0% 6% Furniture & Home Furnishings U.S. Online Penetration ³ 7% 8% 10% 12% 2010 2011 2012 2013 2014 14% 16% 19% 21% 24% 34% 34% 29% 30% 33% 33% Feb-22 Jun-22 2015 2016 2017 2018 2019 2020 2021 2022 (est.) 1 Source: Insider Intelligence/eMarketer 2021 estimate of total U.S. Furniture & Home Furnishings market size as of Jun 2022. 2 Source: Public, third-party analyses and transactional data based on commonly accepted definition of 'home furnishings and décor' category (which includes furniture) and ranked by direct-to-customer online sales. 3 Source: 2010-2023: eMarketer/Insider Intelligence full year estimates as of Jun 2022. 18#19Unique Market Positioning Dream Homes for All: Smart Value = Quality & Style for less Overstock Customers Smart Value Seekers overstock. Savvy Shoppers Reluctant Refreshers Value IKEA Home Goods Expertise Oloverstock. Amazon Walmart Pottery Barn Wayfair West Elm Bed Bath & Beyond Target Department Store Generalist Source: Based on Overstock Annual Brand Research, 2020. Shown are the top ten U.S. home furnishings online home retailers, as ranked by online revenue. Restoration Hardware Style & Inspiration 19#20Brand Pillars: Product Findability overstock. 3 154 Growing breadth and depth of home assortment Serving consumers' evolving home-related needs Home improvement categories outperforming 20#21Brand Pillars: Smart Value Maintained price competitiveness Second largest Memorial Day sales in history App enabled strong customer engagement overstock. 40 21#22Brand Pillars: Easy Delivery & Support overstock. 茶 POR overstock 1 As of year end 2021. Broad and distributed supply chain with vast partner network Increasing allocations from partners helps enhance brand association with home Supporting partners with pricing and cost optimization tools Special promotions to turn partner inventory quickly -3,000¹ Third-party manufacturers, distributors, and other partners ~5,000 Fulfillment centers 22#23Growth Drivers overstock. Improve product findability Optimize marketing channels Improve customer retention Increase brand association with "home" A Q Co Increase mobile app adoption 떡 Increase home assortment Grow Canada 2022 Focus Improve category management 23#24Well-Positioned for Market Share Growth in 2022 and Beyond ▪ Annual revenue outpacing industry ▪ Gross profit margin in the 22% range Operating expenses growing at a slower rate than revenue, driving operating leverage Adjusted EBITDA margins in the mid-single digits ■ Free cash flow positive — overstock. dream homes for all Driving sustainable, profitable market share growth 24#25PELION VENTURE PARTNERS Medici Ventures Fund Update 25#26Medici Ventures Fund Update tZERO SettleMint PEERNOVA overstock. bitt riri evernym Votem MEDICI LAND GOVERNANCE Medici Day Tuesday, May 10, 2022 Voatz yuting uued Vinsent Chainstone Labs BANKORUS FinClusive symbiont NETKI တိုင် Vital Chain tZERO bitt 26#27overstock. Summary and Q&A#28Q2 2022 Review and Looking Ahead Q2 2022 Review ■ Remained profitable Repurchased shares Healthy balance sheet overstock. 2 Execute on Brand Pillars Business for the Long Term Strengthen brand association with 'home' Improve customer engagement ▪ Leverage unique fulfillment model ■ ■ Continue to grow US market share ▪ Deliver profitability Replicate model in Canada and beyond ■ 28#29overstock. To ask questions: ▪ access registration link on IR website email: [email protected] questions? 29#30Oloverstock. TM#31overstock. Appendix 31#32Adjusted EBITDA Reconciliation Income from continuing operations Depreciation and amortization Stock-based compensation Interest (income) expense, net Other (income) expense, net Provision (benefit) for income taxes Special items (see table below) Adjusted EBITDA Special items: Special legal charges and other Severance Transaction costs Total Special items overstock. $ $ Jun-2020 47,839 $ 5,409 1,952 364 (246) 840 (7,272) 48,886 $ (7,272) $ (7,272) $ Sep-2020 37,904 $ 5,310 1,568 264 (59) 753 288 46,028 $ 288 288 $ Dec-2020 23,150 $ 5,488 1,640 199 (595) (393) 432 29,921 $ 432 $ 432 $ Mar-2021 Three months ended Jun-2021 26,018 $ 5,146 2,305 155 226 193 (187) 33,856 $ (187) $ (187) $ 82,405 $ 4,803 2,802 130 (298) (45,726) 243 44,359 $ 243 243 $ Sep-2021 30,426 $ 4,383 2,542 139 79 (1,795) 305 36,079 $ 1 $ 253 51 305 $ Dec-2021 32,942 $ 4,232 3,484 132 (12,507) (1,447) 511 27,347 $ 502 9 511 $ Mar-2022 10,123 $ 4,307 4,639 125 114 2,092 53 21,453 $ 53 53 $ Jun-2022 7,147 4,043 4,695 (115) 1,981 2,529 475 20,755 471 4 475 Note: All figures represent results from continuing operations, in thousands. Adjusted EBITDA is a non-GAAP financial measure used in addition to and in conjunction with results presented in accordance with GAAP and should not be relied upon to the exclusion of GAAP financial measures. Review our financial statements and publicly-filed reports in their entirety and do not rely on any single financial measure. 32#33Adjusted Diluted EPS Reconciliation in thousands, except per share data Numerator: Income from continuing operations Less: Preferred stock dividends accumulated Undistributed income from continuing operations Less: undistributed earnings allocated to participating securities Net income form continuing operations attributable to common stockholders Denominator: Weighted average shares of common stock outstanding-diluted Net income from continuing operations per share of common stock: Diluted overstock. $ Diluted EPS 7,147 1,697 5,450 410 5,040 43,159 0.12 $ Note: All figures represent results from continuing operations, in thousands, except per share data. 1 Non-cash dividend related to preferred share conversion. 2 Inclusive of tax impact from equity method activity. Three months ended June 30, 2022 Less: non-cash preferred stock dividend ¹ 1,697 (1,697) (128) (1,569) 43,159 (0.03) Less: equity method income (loss)² $ (1,793) (1,793) (135) (1,658) 43,159 (0.04) Adjusted Diluted EPS 8,940 8,940 673 8,267 43,159 0.19 33