#1Oloverstock Q1 2021 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 market volatility, the world economy, government regulation, and our supply chain, including supply and demand for the products and services we offer, and the ability of our third-party partners and carriers to provide products and services without interruption and at a reasonable cost. Actual results could also differ materially for a number of reasons, including, but not limited to initiatives to improve or maintain the performance of our business, adverse tax, regulatory or legal developments, competition, and any inability to maintain profitability, continue to generate positive cash flow from operations, raise capital, or borrow funds on acceptable terms, difficulties we may have with our infrastructure, our fulfillment partners or our payment processors, including cyber-attacks or data breaches affecting us or any of them, any inability to protect our intellectual property, and difficulties we may experience with increasing or maintaining our search engine optimization results, converting web traffic to sales, or ensuring we maintain our new customer base. Other risks and uncertainties include, among others, whether our partnership with Pelion Venture Partners will be able to achieve its objectives and the timing for doing such. More information about factors that could potentially affect our financial results are included in our Form 10-K for the year ended December 31, 2020, which was filed with the SEC on February 26, 2021, and in our subsequent filings with the SEC. The Form 10-K 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#4Corporate Update Closed blockchain fund transaction with Pelion Venture Partners on April 23 Announced strategic partnership on January 25 (original goal to close by mid-July) Medici Ventures converted into a limited partnership (the "Fund") overseen by Pelion Medici Ventures de consolidated in financial results - - Regulatory front - no updates Annual shareholder meeting on May 13 Continue to operate well working remote-first overstock. 4#5overstock. Financial Results 5#6Q1 2021 Financial Results Revenue $659.9 Million +94% vs. Q1'20 +82% vs. Q1'19 Adjusted EBITDA² $33.9 Million +$40.4M / +618% vs. Q1'20 +$41.7M/+530% vs. Q1'19 overstock. Gross Margin 23.3% +141bps vs. Q1'20 +342bps vs. Q1'19 Diluted EPS $0.56 +$0.90 vs. Q1'20 +$1.15 vs. Q1'19 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 expense in Q1'20 was $51.2M, or 15.1% of revenue. 2 Adjusted EBITDA is a non-GAAP financial measure. See Reconciliation in Appendix. G&A and Tech % of Revenue 8.1% -771bps vs. Q1'20¹ -783bps vs. Q1'19 Ending Cash $534.8 Million +$39.4M vs. Q4'20 +$438.3M vs. Q4'19 6#7Revenue Revenue ($M) $800 $700 $600 $500 $400 $300 $200 $100 $363 (18%) Q1 '19 overstock. $367 (23%) Q2 '19 + $341 (22%) Q3 '19 $364 (19%) Q4 '19 $340 (6%) Q1 '20 Note: All figures represent results from continuing operations. $767 $718 109% 111% Q2 '20 Q3 '20 $670 84% Q4 '20 YOY Revenue $660 94% Q1 '21 A 120% 100% 80% 60% 40% 20% 0% (20%) (40%) Q1 Dynamics ■ Revenue of $660M +94% / $320M vs. Q1'20 +82% / $297M vs. Q1'19 7#8Gross Margin Gross Profit ($M) $225 $200 $175 $150 $125 $100 $75 $50 $25 19.9% $72 Q1 '19 overstock. 19.7% $72 Q2 '19 20.0% $68 Q3 '19 20.7% $75 Q4 '19 21.9% $74 Q1 '20 Note: All figures represent results from continuing operations. 23.2% $178 Q2 '20 23.5% $169 Q3 '20 22.5% $151 Q4 '20 Gross Margin (%) 23.3% $154 Q1 '21 25% 20% 15% 10% 5% H 0% Q1 Dynamics ■ Gross margin of 23.3% +141bps vs. Q1'20 +342bps vs. Q1'19 ▪ Gross margin benefited by: Continued sales mix into core home furnishings categories Disciplined discounting activities offset by increased acquisition marketing 8#9G&A and Tech Expense G&A and Tech Expense ($M) $80 $70 $60 $50 $40 $30 $20 $10 $- 15.9% $58 Q1 '19 overstock. + 14.1% $52 14.1% $48 14.4% $52 15.8% 1 15.1% $54 $57 7.5%2 6.5% G&A and Tech Exp % of Revenue (%) Q2 '20 $59 8.2% $54 Q3 '20 8.1% $53 Q4 '20 8.1% 18% Q1 '21 16% 14% 12% 10% 8% 6% Q3 '19 Q4 '19 Q2 '19 Q1 '20 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 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 expense in Q2'20 was $49.9M, or 6.5% of revenue. 4% 2% -0% Q1 Dynamics ■ ■ G&A and tech expense generating operating leverage -1% vs. Q1'201 -8% vs. Q1'19 G&A and tech expense % of revenue of 8.1% -771bps vs. Q1'20¹ -783bps vs. Q1'19 9#10Adjusted EBITDA Adj. EBITDA ($M) $60 $50 $40 $30 $20 $10 $- $(10) $(20) $(30) $(40) H $(8) (2.2%) Q1 '19 overstock. $(2) (0.7%) Q2 '19 $(5) (1.4%) Q3 '19 $(7) (1.8%) Q4 '19 $(7) (1.9%) Q1 '20 $49 6.4% Q2 '20 $46 6.4% Q3 '20 Note: All figures represent results from continuing operations. Retail Adjusted EBITDA is a non-GAAP financial measure. See Reconciliation in Appendix. + Adj. EBITDA Margin (%) $30 4.5% Q4 '20 $34 5.1% Q1 '21 1 8% 6% 4% 2% 0% (2%) (4%) Q1 Dynamics ■ ■ Adj. EBITDA of $34M +$40M vs. Q1'20 +$42M vs. Q1'19 Adj. EBITDA margin of 5.1% +706bps vs. Q1'20 +730bps vs. Q1'19 10#11Active Customers and Order Frequency Active Customers (M) 12 10 8 6 4 2 1.75 6.2 Q1 '19 overstock. 1.76 5.8 Q2 '19 1.76 5.4 Q3 '19 1.75 5.1 Q4 '19 1.70 5.2 Q1 '20 1.62 7.0 Q2 '20 1.63 8.2 Q3 '20 Orders per Active Customer 1.64 9.2 Q4 '20 1.66 9.9 Q1 '21 2.0 1.5 1.0 0.5 Q1 Dynamics ■ Active customers reached record of 9.9M +92% / +4.8M vs. Q1'20 +60% / +3.7M vs. Q1'19 ■ Order frequency of 1.66 -2% vs. Q1'20 -5% vs. Q1'19 Impacted by influx of new customers Note: Active customers represents the number of customers who made at least one purchase during the prior twelve-month period. 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. 11#12Orders and Average Order Value Orders Delivered (LTM) (M) 20 18 16 14 12 10 8 6 4 2 $155 10.9 Q1 '19 overstock. $166 10.2 Q2 '19 $167 9.6 Q3 '19 $155 8.9 Q4 '19 $156 8.8 Q1 '20 $160 11.3 Q2 '20 $173 13.4 Q3 '20 Average Order Value $168 15.1 Q4 '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. $183 16.5 Q1 '21 $200 $180 $160 $140 $120 $100 $80 $60 $40 $20 $- Q1 Dynamics Orders delivered (LTM) reached record of 16.5M ■ ■ +88% / +7.7M vs. Q1'20 +52% / +5.7M vs. Q1'19 Average order value of $183 +17% vs. Q1'20 +18% vs. Q1'19 Driven by continued sales mix into core home furniture categories - 12#13overstock. Business Updates 13#14Oloverstock TM aber 14#15Top 4 Brand in a Growing Market Top U.S. Home Furnishings Online Brands¹ (ranked by online revenue) 1. Amazon 2. Wayfair 3. Walmart 4. loverstock 5. Target 6. Pottery Barn IKEA Bed Bath & Beyond 1. 8. 9. West Elm 10. Restoration Hardware overstock. 50% 40% 30% 20% 10% 0% 6% 2010 Furniture & Home Furnishings U.S. Online Penetration ² 7% 2011 8% 2012 9% 2013 11% 2014 13% 2015 16% 2016 18% 2017 20% 2018 23% 2019 29% 2020 35% Mar 2021 (est.) 1 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 2020 direct-to-customer online sales. 2 Source: Combined data from eMarketer, NRF, NPD, and Earnest transactional data. 15#16Establishing Unique Market Positioning Dream Homes for All: The space of 'Smart Value' where quality & style costs less Value + overstock. IKEA overstock Amazon Home Goods Expertise Walmart Target Wayfair Bed Bath & Beyond 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 16#17Playing to Our Strengths overstock. Savvy Shoppers overstock Reluctant Refreshers $130B Market¹,2 1 Source: eMarketer-Total U.S. Retail Sales estimates, 2020. 2 Source: Overstock customer segmentation research, 2019. Note: $325B total market size x 40% customer segments market size = $130B market. Higher propensity to shop at Overstock ▪ Deal-driven and low-hassle ▪ Combined market spend is 40% of total market² 17#18Focused Strategy vision financial goal target customers brand pillars enablers 2021 initiatives overstock. dream homes for all making beautiful & comfortable homes accessible by helping customers easily & confidently find just what they want for less sustainable, profitable market share growth primary segment savvy shopper values Overstock for helping them feel smart about finding a great deal from a compelling selection of stylish & quality home products product find ability get inspired anywhere, but easily find it at Overstock OKR-driven focus world-class SEO smart value quality & style for less secondary segment reluctant refresher values Overstock for helping them easily & confidently find just what they want easy delivery + support data-driven customer relationship. and loyalty building machine learning and algorithms innovation improve product findability grow government market share grow Canada market share improve enterprise platform fast, free, & predictable delivery, plus low-hassle returns & support rapid iteration mindset 18#19product findability ■ Customers shifted to mobile In Q1, mobile: ▪ Purchases >50% of total sales Unique visits +62% YoY - Sales +105% YoY - Conversion +10% YoY ▪ Focus on app adoption in 2021 80% 60% 40% 20% 0% H 80% 60% 40% 20% 0% H Q1'19 Q1'19 Q2'19 Q2'19 Q3'19 Sales % by Device Q3'19 Q4'19 Q1'20 Q4'19 Orders Delivered % by Device Q2'20 Q1'20 Q2'20 Mobile Desktop Q3'20 Mobile Desktop Q3'20 Q4'20 Q4'20 overstock. Note: Sales reflects GMS (gross merchandise sales), calculated as the amount paid by customers for products (and shipping), measured at the time of order, before coupons and discounts, without reductions for estimated returns. Q1'21 Q1'21 1 19#20product findability ▪ Demand for home furnishings continues to increase. ■ - Home furnishings were 93% of sales in Q1 Highest home furnishings mix in history Opportunity to increase brand association with "Home" 2X higher purchase intent if shopper comes to OSTK for "Home" Emphasizing Dream Homes for All overstock. 2015 2016 2017 Sales Mix of Home Furnishings 2018 2019 91% 2020 Q1'19 Q1'20 93% Q1'21 Note: Sales Mix is shown as a percentage of gross merchandise volume, calculated as the amount paid by customers for products (and shipping), measured at the time of order, after coupons and discounts, without reductions for estimated returns. 20#21product findability ▪ Assortment and SKU productivity continue to increase Number of SKUs sold +24% YoY Units sold per SKU +36% YoY overstock. Note: Chart reflects home furnishings SKUs only. Q1'19 SKUs Sold Units Sold per SKU Q2'19 Assortment Optimization Q3'19 Q4'19 Q1'20 Q2'20 Q3'20 Q4'20 Q1'21 21#22smart value ■ Free shipping is a top purchase driver and key component of Smart Value Launched free shipping on all items in 2020 Customer rating of shipping charges expected to remain at current levels overstock. 1 Source: Bizrate point of sale survey, Q1 2021. Q1 '20 Customer Rating of Shipping Charges¹ Q2 '20 Q3 '20 Q4 '20 12% favorable to competitors Q1 '21 22#23smart value ■ ■ Savvy Shoppers expect value Want to feel like they are getting "best quality for the price" - Progress evident in continued refinement of pricing model Pricing is another key component of Smart Value overstock. 55% Dec '19 Competitively Priced SKUs 70% Jul '20 80% Dec '20 85% Mar '21 Note: Overstock prices used to compare to competitor prices include site sale discounts before coupons are applied. Comparisons account for 30-35% of all product page views. Price comparisons taken during last week of respective month reported. 23#24■ easy delivery + support Delivery speed and on-time accuracy key drivers of customer conversion and retention - For customers, maintained focus on communicating delivery expectations during times of operational disruption - For carriers, managed disruptions through rigorous planning, estimation accuracy, and communications overstock. ✓ % Orders Delivered On-Time or Early + + + + + 1/5/20 2/5/20 3/5/20 4/5/20 5/5/20 6/5/20 7/5/20 8/5/20 9/5/20 10/5/20 11/5/20 12/5/20 1/5/21 2/5/21 3/5/21 Note: % orders delivered on-time or early and click to delivery refer to small parcels only. w Click to Delivery (business days) Texas storms un ㅏ + + + 1/5/20 2/5/20 3/5/20 4/5/20 5/5/20 6/5/20 7/5/20 8/5/20 9/5/20 10/5/20 11/5/20 12/5/20 1/5/21 2/5/21 3/5/21 24#25easy delivery + support ■ Contact volume as a percentage of orders decreased 29% vs. Q1'19 ▪ Automation and self-service capabilities improve customer retention and reduce costs - Continue to enhance and augment self-service functionality overstock. Q1'19 Q1'19 + + Q2 '19 Q2 '19 + Q3 '19 CS Contacts as % of Orders Q3 '19 + Q4 '19 29% decrease + Q4 '19 Q1 '20 4.4x increase Self Service Cases as % of Total Q2 '20 Q1 '20 Q2 '20 + Note: Following the national stay-at-home order (Q2'20), not all customers were able to reach customer service agents due to unexpected volume of sales. Q3 '20 + Q3 '20 Q4 '20 Q4 '20 + Q1 '21 Q1 '21 1 25#262021 Strategic Initiatives 1 Improve onsite search and taxonomy 2 3 4 overstock. Expand into Canada Establish government business Improve the enterprise platform 26#27Well Positioned for Market Share Growth in 2021 and Beyond ▪ Revenue growth outpacing industry ▪ Gross profit margin in the 22% range Operating expenses growing slower 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. 27#28Medici Ventures Fund 28#29Summary of Medici Ventures Fund Transaction overstock. Deal Type General Partner Limited Partner Partnership Term Capital Commitment Fee Structure Timing Deal Rationale Partnership between Overstock and Pelion Venture Partners A Pelion Venture Partners entity Overstock 8 years $45 million (with Overstock option to increase by $30 million) Annual fees of $2.5 million, combined with success fees paid. according to performance Announced on January 25; closed on April 23 Maximize shareholder value through partnering with a highly experienced venture firm 29#30Medici Ventures Fund Update Bitt launched DCash, the world's first central bank digital currency, on March 31 tZERO: Launched strategic capital raise Hosting Q1 update call in May Grain Chain selected by SAP for its global startup accelerator program on April 14 Voatz closed first tranche of $10M capital raise on April 20 PeerNova closed first tranche of $25M capital raise on April 22 - overstock. 30#31overstock. Summary and Q&A 31#32Q1 Review and Looking Ahead ■ Closed Pelion transaction and deconsolidated Medici Ventures' businesses Execute against our 2021 initiatives Increase Overstock brand association with "Home" Cement competitive positioning Improve mobile app adoption. Continue to deliver profitable market share growth overstock. 32#33Questions? To ask questions: Dial-in: (877) 673-5346 Conference ID: 5898642 Email: [email protected] ■ overstock. 33#34overstock. Appendix 34#35Adjusted 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 ¹ Severance Total Special items overstock. SA Mar-2019 Jun-2019 Sep-2019 (19,490) $ (13,230) $ (13,448) $ 5,266 6,127 6,212 3,868 4,560 3,821 (240) (458) (321) 105 419 183 864 136 160 (1,221) (4,614) $ 1,757 (7,870) $ 1,757 1,757 $ (2,446) $ Dec-2019 (1,221) $ Three months ended Mar-2020 (1,221) $ (16,740) $ (13,766) $ 6,474 5,569 3,911 2,681 (182) 11 (65) 287 (100) 163 (1,486) (6,541) $ (6,702) $ $ Jun-2020 (2,501) $ 1,015 (1,486) $ 48,174 5,410 1,952 364 (246) 505 (7,272) 48,887 Sep-2020 $ (7,272) $ (7,272) $ Dec-2020 (59) 607 288 46,028 38,050 $ 23,092 $ 5,310 5,487 1,568 1,640 264 199 (595) (335) 432 29,920 $ 288 288 $ 432 $ Mar-2021 432 $ Note: All figures represent results from continuing operations. 1 Special legal charges include amounts associated with the resolution for and adjustments to various legal contingencies and legal fees associated with pursuing our strategic alternatives. 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. 26,018 5,146 2,305 155 226 193 (187) 33,856 (187) (187) 35