#1Oloverstock Q1 2022 Earnings Call TM NO L#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, 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 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, 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 PRADA PRADA#5Corporate Update Simplifying capital structure Expanded and executed share repurchases ▪ FORWARD Plan Kickoff - April Homecoming ■ overstock. 5#6overstock. Financial Results 6#7Q1 2022 Financial Results Revenue $536.0 Million -19% vs. Q1'21 +58% vs. Q1'20 Adjusted EBITDA Margin¹ 4.0% overstock. -113 bps vs. Q1'21 +593 bps vs. Q1'20 Gross Margin 23.4% +9 bps vs. Q1'21 +151 bps vs. Q1'20 Diluted EPS $0.21 Adjusted Diluted EPS² $0.21 -$0.35 vs. Q1'21 +$0.55 vs. Q1'20 Note: All figures represent results from continuing operations. 1 Adjusted EBITDA Margin is a non-GAAP financial measure. See reconciliation in appendix. 2 Includes immaterial adjustment related to equity method activity. See reconciliation in appendix. G&A and Tech % of Revenue 10.1% +203 bps vs. Q1'21 -568 bps vs. Q1'20 Ending Cash $493.3 Million -2% -$10.1M vs. Q4'21 -8% /-$41.5M vs. Q1'21 7#8Revenue $800 $700 $600 $500 $400 $300 $200 $100 $0 Revenue ($M) $340 Q1 '20 overstock $767 Q2 '20 $718 Q3 '20 $670 +58% Q4 '20 $660 Q1 '21 Note: All figures represent results from continuing operations. $795 Q2 '21 $689 - 19% Q3 '21 $613 Q4 '21 $536 Q1 '22 Q1 Dynamics I Revenue of $536M -19%-$124M vs. Q1'21 +58% / +$196M vs. Q1'20 8#9Gross Margin $225 $200 $175 $150 $125 $100 $75 $50 $25 $0 Gross Margin ($M) 21.9% $74 Q1 '20 overstock 23.2% $178 Q2 '20 3.5% $169 Q3 '20 22.5% $151 Q4 '20 23.3% $154 Q1 '21 Note: All figures represent results from continuing operations. 22.0% $175 Q2 '21 22.7% $157 Q3 '21 22.7% $139 Q4 '21 Gross Margin (%) 23.4% $125 Q1 '22 25% 20% 15% 10% 5% 0% Q1 Dynamics I Gross margin of 23.4% +9 bps vs. Q1'21 +151 bps vs. Q1'20 ▪ Gross margin influenced by: Normalized promotional environment vs. last year Operational efficiencies 9#10G&A and Tech Expense $80 $70 $60 $50 $40 $30 $20 $10 $0 G&A and Tech Expense ($M) 15.8% 1 15.1% $54 1 Q1 '20 overstock. $57 2 7.5%² 6.5% $59 8.2% $54 8.1% $53 8.1% $53 6.7% $52 Q2 '21 7.6% G&A and Tech Exp. as % of Revenue Q3 '21 $52 8.4% $54 Q4 '21 10.1% 18% Q1 '22 16% 14% 12% 10% 8% 6% Q2 '20 Q3 '20 Q4 '20 Q1 '21 Note: All figures represent results from continuing operations. 1 In Q1'20 we recorded $2.5M in special items that benefited G&A expense. Reported G&A and tech expense in Q1'20 was $51.2M or 15.1% of revenue. 2 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. 4% 2% 0% Q1 Dynamics Stable G&A and tech expenses +2% vs. Q1'21 In line with Q1'20 I - G&A and tech expense % of revenue of 10.1% +203 bps vs. Q1'21 -568 bps vs. Q1'20 10#11Adjusted EBITDA $60 $50 $40 $30 $20 $10 $0 ($10) ($20) Adjusted EBITDA ($M) ($40) ($7) ($30) (1.9%) Q1 '20 $49 6.4% Q2 '20 $46 6.4% Q3 '20 $30 4.5% Q4 '20 $34 5.1% Q1 '21 overstock. Note: All figures represent results from continuing operations. $44 5.6% Q2 '21 $36 5.2% Q3 '21 Adjusted EBITDA Margin (%) $27 4.5% Q4 '21 $21 4.0% Q1 '22 10% 8% 6% 4% 2% 0% (2%) (4%) Q1 Dynamics I ■ Adj. EBITDA of $21M -$12M vs. Q1'21 +$28M vs. Q1'20 Adj. EBITDA margin of 4.0% -113 bps vs. Q1'21 +593 bps vs. Q1'20 11#12Active Customers and Order Frequency 12 10 8 6 2 0 Active Customers (LTM) (M) 1.70 5.2 Q1 '20 overstock. 1.62 7.0 1.63 Q2 '20 8.2 1.64 9.2 1.66 9.9 1.69 9.2 Q2 '21 Order per Active Customer (LTM) 1.68 8.7 1.67 Q3 '21 8.1 Q3 '20 Q4 '20 Q1 '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. 1.67 Q4 '21 7.4 Q1 '22 Q1 Dynamics ▪ Active customers of 7.4M -26%/-2.5M vs. Q1'21 +43% / +2.2M vs. Q1'20 Influx of pandemic customers Non-home category exit - Order frequency of 1.67 +0.4% vs. Q1'21 -2% vs. Q1'20 Improved home association - 12#13Orders and Average Order Value 25 20 15 10 5 0 Orders Delivered (LTM) (M) $156 8.8 Q1 '20 overstock. $160 11.3 $173 13.4 $168 15.1 $183 16.5 $213 15.5 $214 14.5 Average Order Value $206 13.5 Q2 '20 Q3 '20 Q4 '20 Q1 '21 Q2 '21 Q3 '21 Q4 '21 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. $221 Q1 '22 $250 $200 $150 $100 $50 $0 Q1 Dynamics Orders delivered (LTM) of 12.3M -25%/-4.2M vs. Q1'21 +41%/ +3.6M vs. Q1'20 I ■ Average order value of $221 +21% vs. Q1'21 +41% vs. Q1'20 Sales mix of home categories - 13#14Home-only Active Customers and Revenue Q1 LTM Active Customers Change Reported -26% YoY Excluding non-home only¹ customers -23% YoY ■ 0% -5% -10% -15% -20% -25% -30% overstock. -12% -9% Q4 '21 -26% -23% Q1 '22 Actual/ Reported Excluding non-home only customers Q1 Revenue Change Reported -19% YoY Excluding non-home only¹ customers -16% YoY 0% -5% -10% -15% -20% -25% -30% -9% -5% Q4 '21 -19% -16% Q1 '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. 14#15Balance Sheet Highlights overstock. Cash $493 Million -2% / -$10M vs. Q4'21 1 Cash less long-term debt. Net Cash Position¹ $456 Million -2% / -$9M vs. Q4'21 Long-term Debt $37 Million -2% / -$1 M vs. Q4'21 No significant debt maturity until March 2030 15#16loverstock. Business Updates WETE Super 2 124 16#17Top 4 Brand in a Growing -$390B Market' Top U.S. Home Furnishings Online Brands² (ranked by online revenue) 1. Amazon 2. Wayfair 3. Walmart 4. Oloverstock. 5. Target 6. Pottery Barn IKEA Bed Bath & Beyond 1. 8. 9. West Elm 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% 29% 30% 33% 35% 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023 (est.) (est.) 1 Source: Insider Intelligence/eMarketer 2021 estimate of total U.S. Furniture & Home Furnishings market size. 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 Feb 2022. 17#18Unique 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 Wayfair Bed Bath & Beyond Target Pottery Barn West Elm 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 18#19Brand Pillars: Product Findability Furniture Rugs Decor Mattress SKU growth + improvement in customer experience = market share gains overstock. mattressen mattresses club' rewards Reinforces home-focused strategy Outdoor Shower Cu futon mattresses extra firm mattresses bed in a box mattresses twin mattresses cooling mattresses queen mattresses blow up mattresses mattresses queen full mattresses Outdoor Sofas Bar Stools overstock. LUCID Com Collection 10 Mass ***** (14118 Sectionals 8 ♡ W Account Lists Notifications Cart Dough by ***** (1 Sumber Solutions 12 nch Gel Memory Foam ***** Computer Desks Line Essentials ***** (14) Linenspa Essentials 10 Memory Foam Hybrid. ***** (119) Office Chairs Rugs ure Check Out Sales & Deals overstock. Mattresses Furniture Rugs Decor Bed & Bath Home Improvement Kitchen Outdoor Jewelry mattresses Memory Foam Mattresses Innerspring Mattresses Mattress in a Box Mattress Sets Adjustable Beds New Arrivals Shop All Mattresses on Sale D 10 SPRING BLACK FRIDAY SHOP NOW EXTRA 20% OFF SELECT MATTRESSES Shop By Size 8 ♡ Account Lists Lighting 0 Nonfications Kids & Baby More 10 Ideas Check Out Sales & Deals 19#20Brand Pillars: Smart Value App downloads +54% QOQ on top of record Q4 +80% Mobile app highest conversion platform Stronger repeat rates among app shoppers loverstock. 5:03 *** Q Search Overstock Latest Offers 20off Free Shipping on EVERYTHING! OW Shop By Today Only: 20% off in the App! Take a monumental 20% off your order for in-app purchases! It's a Presidents Day sale so exclusive, we're surprised you don't need security clearance. Dismiss Your offer has been saved in your notification center. Limited Time Deals Shop & Save! for 8 Acquiring new 'home' customers at higher AOV Smart Value proposition resonating Average Order Value ¹ (1Q22 LTM/ All transactions) Average +11% New customers 1 Weighted average order value based on total gross merchandise sales and total orders. Average represents all Overstock transactions over the last twelve months through March 31, 2022. New customers represents transactions tied to new customers acquired over the last twelve months through March 31, 2022. 20#21Brand Pillars: Easy Delivery & Support ERY RY ON OG DELIVERY 2-8 DAY 2-M HAY 1 30 2-Y Daily EO overstock. B ILIER 1 As of year end 2021. KEBELFE annual WT HES E 5 AR ZAM PWY UN MELRY E DELIVERY 2AM VERY 55 X 55 S www BAURE CARGO Broad and distributed supply chain with vast partner network Focus on profitability appreciated by partners - existing and new Frequent communications and planning supports partner profitability Increasing allocations from partners helps enhance brand association with home ~3,000¹ Third-party manufacturers, distributors, and other partners ~5,000¹ Fulfillment centers 21#22Growth Drivers overstock. Improve product find ability Optimize marketing channels Improve customer retention Increase brand association with "home" A Q Co Increase mobile app adoption F Increase home assortment Grow Canada 2022 Focus Improve category management 22#23Well-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 dream homes for all Driving sustainable, profitable market share growth overstock. 23#24PELION VENTURE PARTNERS Medici Ventures Fund Update 24#25Medici Ventures Fund Update tZERO bitt GRAIN ripio spera PELION VENTURE PARTNERS overstock. W WATCH DOG CAPITAL Medici Ventures Fund Day: Being hosted by Pelion on May 10 25#26overstock. Summary and Q&A DEY 26#27Q1 2022 Review and Looking Ahead Q1 2022 Review ▪ Held market share ▪ Maintained profitability Healthy balance sheet overstock. E ? 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 27#28overstock. To ask questions: Dial-in: (877) 673-5346 Conference ID: 7170114 ▪ Email: [email protected] ■ questions? 28#29Oloverstock TM L 29#30overstock. Appendix 30#31Adjusted EBITDA Reconciliation Income (loss) from continuing operations Depreciation and amortization Stock-based compensation Interest expense, net Other (income) expense, net Provision (benefit) for income taxes Special items (see table below) Adjusted EBITDA Special items: Special legal charges Severance Transaction costs Total Special items overstock. $ Mar-2020 (13,766) $ 5,569 2,681 11 287 163 (1,486) (6,541) $ (2,501) $ 1,015 (1,486) $ 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 Three months ended Mar-2021 23,150 $ 5,488 1,640 199 (595) (393) 432 29,921 $ 432 $ 432 $ 26,018 $ 5,146 2,305 155 226 193 (187) 33,856 $ (187) $ (187) $ Jun-2021 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 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. 31#32Adjusted 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 10,123 182 9,941 952 8,989 43,282 0.21 Note: All figures represent results from continuing operations, in thousands, except per share data. 1 Inclusive of tax impact from equity method activity. Three months ended March 31, 2022 Less: equity method income/(loss) ¹ $ $ $ $ 32 32 3 29 43,282 Adjusted Diluted $ $ $ 0.00 $ EPS 10,091 182 9,909 949 8,960 43,282 0.21 32