#1O overstock. Q3 2022 Earnings Call R#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 ultimate impact of the COVID- 19 pandemic on our business and results of operations, global conflict including the ongoing 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 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, our Form 10-Q for the quarter ended June 30, 2022 which was filed with the SEC on August 2, 2022 and in our subsequent filings with the SEC. The Form 10-K, Form 10-Qs, 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#4Ooverstock. CEO Remarks **#5Home-only Revenue Trend Stabilized 3-year Look Back ▪ 53% growth vs. 2019 ■ Home-only Revenue ($M) $700 $600 $500 $400 $300 $200 $100 Outpaced TAM expansion ¹ $0 Q3 '19 overstock. Largest Q3's in history Q3 '20 Q3 '21 +53% $460 Q3'22 Home-only Revenue (YoY %) 0% H -5% -10% -15% -20% -25% -30% Revenue Trend YoY ▪ Transitioned to 100% home-only assortment by end of Q2 Sequential stabilization during Q3 -35% -5.3% Q4 '21 " -16.2% Q1 '22 -30.5% Q2 '22 -29.7% Q3'22 1 Source: Insider Intelligence/eMarketer 2019 through 2022 estimates of total U.S. Furniture & Home Furnishings market size as of Jun 2022. 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. 5#6Corporate Update ▪ Review of organizational structure ▪ Launched national brand campaign overstock. our refreshed vision making dream homes come true overstocktober celebration Overstock Making dream homes come true overstock Overstock overstocktober celebration belonging believing becoming 6#7National Brand Campaign Overview Commercial Oloverstock c'mon get comfy... overstock. National Brand Ambassadors Left to Right: Taniya Nayak Farah Merhi Tarek El Moussa · Luke Caldwell · Vanessa Deleon Lizzy Mathis . About 20 million social media followers in aggregate ¹ 1 Total of Instagram, Facebook, Pinterest, YouTube, TikTok, and Twitter. . overs ■ Media Platforms ▪ Social Media ▪ Influencer Partnerships ■ Streaming Video/Audio ▪ Traditional TV our vision making dream homes come true 7#8overstock. Financial Results 8#9Q3 2022 Financial Results Revenue $460.3 Million -33% vs. Q3'21 Adjusted EBITDA Margin¹ 3.2% -202 bps vs. Q3'21 overstock. Gross Margin 23.3% +62 bps vs. Q3'21 Diluted EPS ($0.81) Adjusted Diluted EPS² $0.13 -$0.41 vs. Q3'21 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 tax impact of equity method activity. See reconciliation in appendix. G&A and Tech % of Revenue 10.5% +292 bps vs. Q3'21 Ending Cash $427.5 Million -3%-$15.1M vs. Q2'22 9#10Revenue $800 $700 $600 $500 $400 $300 $200 $100 Revenue ($M) $0 H $718 Q3 '20 overstock. $670 Q4 '20 $660 Q1 '21 $795 Q2 '21 $689 Q3 '21 Note: All figures represent results from continuing operations. $613 Q4 '21 -33% $536 Q1 '22 $528 Q2 '22 $460 Q3 '22 Q3 Dynamics ■ Revenue of $460.3M ■ -33%/-$229M vs. Q3'21 Revenue influenced by: Macro / consumer sentiment Non-home category exit 10#11Gross Margin $225 $200 $175 $150 $125 $100 $75 $50 $25 Gross Margin ($M) $0 H 3.5% $169 Q3 '20 overstock. 22.5% $151 Q4 '20 + 23.3% $154 Q1 '21 22.0% $175 Q2 '21 22.7% $157 Q3 '21 Note: All figures represent results from continuing operations. 22.7% $139 Q4 '21 23.4% $125 Q1 '22 22.9% $121 Q2 '22 Gross Margin (%) 23.3% $107 Q3 '22 25% 20% 15% 10% 5% -0% Q3 Dynamics ■ Gross margin of 23.3% +62 bps vs. Q3'21 ▪ Gross margin influenced by: Operational efficiencies Offset by higher discounting 11#12G&A and Tech Expense $80 $70 $60 $50 $40 $30 $20 $10 G&A and Tech Expense ($M) $0 H $59 8.2% Q3 '20 overstock. $54 8.1% Q4 '20 + $53 8.1% Q1 '21 $53 6.7% Q2 '21 $52 7.6% Q3 '21 Note: All figures represent results from continuing operations. $52 8.4% Q4 '21 $54 10.1% Q1 '22 G&A and Tech Exp. as % of Revenue $52 9.8% Q2 '22 $48 10.5% Q3 '22 18% 16% 14% 12% 10% 8% 6% 4% 2% -0% Q3 Dynamics G&A and Tech Expense of $48M - -8% vs. Q3'21 ■ - G&A and tech expense % of revenue of 10.5% +292 bps vs. Q3'21 12#13Adjusted EBITDA $60 $50 $40 $30 $20 $10 Adjusted EBITDA ($M) $0 H $46 6.4% Q3 '20 overstock. $30 4.5% Q4 '20 $34 5.1% Q1 '21 $44 5.6% Q2 '21 $36 5.2% Q3 '21 Note: All figures represent results from continuing operations. $27 4.5% Q4 '21 $21 4.0% Q1 '22 Adjusted EBITDA Margin (%) $21 3.9% Q2 '22 $15 3.2% Q3 '22 12% 10% 8% 6% 4% 2% -0% Q3 Dynamics ▪ Adj. EBITDA of $15M - -$21M vs. Q3'21 ■ Adj. EBITDA margin of 3.2% -202 bps vs. Q3'21 13#14Active Customers and Order Frequency 12 10 8 6 2 Active Customers (LTM) (M) 0 H 1.63 8.2 Q3 '20 loverstock. 1.64 9.2 Q4 '20 1.66 9.9 Q1 '21 1.69 9.2 Q2 '21 1.68 8.7 1.67 8.1 Q4 '21 Orders per Active Customer (LTM) 1.67 7.4 Q1 '22 1.65 6.5 Q2'22 1.62 5.8 Q3 '22 Q3 Dynamics ■ Active customers of 5.8 M -33% / -2.9M vs. Q3'21 Macro / consumer sentiment Non-home category exit - Order frequency of 1.62 -4% vs. Q3'21 Improved home association Q3 '21 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. 14#15Orders and Average Order Value Orders Delivered (LTM) (M) 25 20 15 10 5 0 H $173 13.4 Q3 '20 loverstock. $168 15.1 $183 16.5 Q1 '21 $213 15.5 Q2 '21 $214 14.5 Q3 '21 $206 13.5 Q4 '21 $221 Q4 '20 Q1 '22 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. 12.3 Average Order Value $247 10.7 Q2 '22 $243 9.4 Q3'22 $250 $200 $150 $100 $50 $0 Q3 Dynamics Orders delivered (LTM) of 9.4 M - -36%/-5.2M vs. Q3'21 ■ ■ Average order value of $243 +13% vs. Q3'21 Sales mix within home categories 15#16Home-only Active Customers and Revenue Q3 LTM Active Customers Change Reported -33.1% YoY Excluding non-home only¹ customers -29.1% YoY ■ 0% H -5% -10% -15% -20% -25% -30% -35% -40% -12.1% -8.8% Q4 '21 overstock. -25.6% -23.1% Q1 '22 -29.2% -26.1% Q2 '22 -33.1% -29.1% Q3'22 Actual/ Reported Excluding non-home only customers Q3 Revenue Change Reported -33.2% YoY Excluding non-home only¹ customers -29.7% YoY 0% H -5% -10% -15% -20% -25% -30% -35% -40% -8.5% -5.3% Q4 '21 -18.8% -16.2% Q1 '22 -33.5% -30.5% Q2 '22 -33.2% -29.7% Q3'22 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. 16#17Q3 2022 Balance Sheet & Cash Flow Highlights Cash $428 Million -3% -$15M vs. Q2'22 overstock. ‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒ 1 Cash less long-term debt. Long-term Debt $35 Million -2% / -$1 M vs. Q2'22 No significant debt maturity until March 2030 ‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒ Share Repurchases $60 Million 1H 2022 repurchases. No activity in Q3 2022 Significant uses of cash in YTD 2022 ‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒ ‒‒‒‒‒‒‒‒‒‒‒‒‒ tZERO Series B Funding $15 Million Q1 2022 and Q3 2022 investment tranches ‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒ Net Cash Position ¹ $392 Million -3% -$14M vs. Q2'22 ‒‒‒‒‒‒‒‒‒ 17#18overstock. Business Updates CENTRS 18#19Top 4 Brand in a Growing $419B Market¹ Top U.S. Home Furnishings Online Brands² (ranked by online revenue) 1. Amazon 2. Wayfair 3. Walmart 4. Ooverstock. 5. Target 6. Pottery Barn IKEA Bed Bath & Beyond West Elm 1. 8. 9. 10. Restoration Hardware overstock. 40% 30% 20% 10% 0% 6% Furniture & Home Furnishings U.S. Online Penetration ³ 7% 8% 10% 12% 14% 16% 19% 21% 24% 34% 34% 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 33% 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. 19#20Unique Market Positioning Making Dream Homes Come True Smart Value = Quality & Style for less Overstock Customers Smart Value Seekers overstock. Savvy Shoppers Reluctant Refreshers Value Home Goods Expertise Oloverstock. IKEA 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 Inspiration 20#21Brand Pillars: Product Findability overstock. *** JUADAL 299 Sutkart Broadened assortment of on-trend, quality products to meet evolving consumer demand Strategic positioning of branded giftable products to capture holiday market share 21#22Brand Pillars: Smart Value Pricing competency remained stable in an elevated promotional environment Value proposition increasingly resonating with high income customers Labor Day holiday largest sales day of 2022 overstock. = 0 Search... everything ships for free FREEH labor day clearance massive discounts worth celebrating 70off 1000s of items patio furniture starting at $99 Shop Now featuring SAFAVIEH Q!!! X O 22#23Brand Pillars: Easy Delivery & Support 00 overstock. overstock ups+RROADIE A UPS Company Innovation within our asset-light model to deliver best returns experience in the industry Diversification of third-party LTL delivery carriers supporting faster deliveries. Improvement in customer care productivity 23#24Growth 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 24#25Targeted Financial Operating Model 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 ■ ■ S overstock. making dream homes come true Driving sustainable, profitable market share growth 25#26PELION VENTURE PARTNERS Medici Ventures Fund Update overstock. 26#27Medici Ventures Fund Update tZERO overstock. SettleMint GRAIN CHAIN bitt ripio 27#28overstock. Summary and Q&A 3 28#29Q3 2022 Review and Looking Ahead Q3 2022 Review ▪ Home revenue stabilized ▪ Remained profitable 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 ■ ▪ Grow US market share ▪ Deliver profitability ▪ Replicate model in Canada and beyond 29#30overstock. To ask questions: Access registration link on IR website Email: [email protected] Questions? 30#31O overstock. R#32overstock. Appendix 32#33Adjusted EBITDA Reconciliation Income (loss) 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 loverstock. $ $ 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 26,018 $ 5,146 2,305 155 226 193 (187) 33,856 $ (187) $ (187) $ Jun-2021 Three months ended Sep-2021 82,405 $ 4,803 2,802 130 (298) (45,726) 243 44,359 $ 243 243 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 $ Sep-2022 (36,995) 4,130 4,056 (976) 46,283 (2,653) 923 14,768 27 878 18 923 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. 33#34Adjusted Diluted EPS Reconciliation in thousands, except per share data Numerator: Net income (loss) from continuing operations attributable to common stockholders Denominator: Weighted average shares of common stock outstanding-diluted Net income (loss) from continuing operations per share of common stock: Diluted overstock. Diluted EPS $ (36,995) Note: All figures represent results from continuing operations, in thousands, except per share data. 1 Inclusive of estimated tax impact from equity method activity. 45,708 (0.81) Three months ended September 30, 2022 Less: equity method income (loss) ¹ (42,861) 45,708 (0.94) Adjusted Diluted EPS 5,866 45,708 0.13 34