#1Oloverstock. Q2 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, the duration of the COVID-19 pandemic and its ultimate impact on our business and results of operations, adverse tax, regulatory or legal developments, and competition, including how such factors will be impacted at such time as the pandemic subsides throughout the country and globally. Other risks and uncertainties include, among others, the inherent risks associated with the businesses that Medici Ventures and tZERO are pursuing, our continually evolving business model, and 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, and difficulties we may have with our search engine optimization results. Other risks and uncertainties include, among others, 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, 2020 which was filed with the SEC on February 26, 2021, our Form 10-Q for the quarter ended March 31, 2021 which was filed with the SEC on May 6, 2021, 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 and Corporate Update 2. Financial Results 3. Business Updates 4. Summary and Q&A 3#4Market Opportunity Has Long-Term Favorability Home furnishings market is large and expanding Shift to online accelerated in 2020 Macroeconomic trends support long-term growth overstock. 1 Source: Online survey conducted by Harris Poll on behalf of Zillow, March 2021. 2 Source: Zillow May 2021-May 2022 Home Value & Sales Forecast, June 2021. 3 Source: Combined data from eMarketer, NRF, NPD, and Earnest transactional data. 1 in 10¹ Americans moved in 2020 5%² 2021 forecasted U.S. home sales growth 16%* 2020 U.S. personal savings rate 7%° 2021 forecasted U.S. GDP growth 4 Source: Federal Reserve Bank of St. Louis. 5 Source: Deloitte - U.S. Economic Forecast, June 2021. 6 Source: International Monetary Fund, July 2021. 1/3³ of home furnishings purchased online in 2020 $151T' 2021 forecasted U.S. net household wealth 5 8%° 2021 forecasted U.S. consumer spending growth 4#5Corporate Update ■ Tax valuation allowance release of $47M Released allowance on certain U.S. federal and state deferred tax assets due to recent actual results and expected future financial performance Closed blockchain fund transaction with Pelion Venture Partners in Q2 Consolidated statements of operations: recorded a $228M gain (net of tax, in discontinued operations) to reflect fair value of assets in Medici Ventures Fund and retained minority equity interest in tZERO Consolidated balance sheets: Medici Ventures Fund and retained minority equity interest in tZERO classified as a $330M asset Consolidated statements of cash flow: funded full $45M capital commitment Overstock named to Parity.org's Best Companies for Women to Advance List 2021 overstock. 5#6overstock. Financial Results 6#7Q2 2021 Financial Results Revenue $794.5 Million +4% vs. Q2'20 +116% vs. Q2'19 Adjusted EBITDA² $44.4 Million -$4.5M / -9% vs. Q2'20 +$46.8M/+1914% vs. Q2'19 overstock. Gross Margin 22.0% -119 bps vs. Q2'20 +228 bps vs. Q2'19 Diluted EPS $1.72 Adjusted Diluted EPS³ $0.73 -$0.38 vs. Q2'20 +$1.10 vs. Q2'19 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 expense in Q2'20 was $49.9M, or 6.5% of revenue. 2 Adjusted EBITDA is a non-GAAP financial measure. See reconciliation in appendix. 3 Excludes the impact of $47M tax valuation allowance release. See reconciliation in appendix. G&A and Tech % of Revenue 6.7% -78 bps vs. Q2'20¹ -738 bps vs. Q2'19 Ending Cash $536.4 Million +$1.7M vs. Q1'21 +$235.7M vs. Q2'20 7#8Revenue Revenue ($M) $800 $700 $600 $500 $400 $300 $200 $100 $367 Q2 '19 overstock. $341 Q3 '19 $364 Q4 '19 +116% $340 Q1 '20 $767 Q2 '20 Note: All figures represent results from continuing operations. $718 Q3 '20 $670 Q4 '20 +4% $660 Q1 '21 $795 Q2 '21 Q2 Dynamics ■ Revenue of $795M - +4% / $28M vs. Q2'20 +116% / $427M vs. Q2'19 8#9Gross Margin Gross Profit ($M) $225 $200 $175 $150 $125 $100 $75 $50 $25 19.7% $72 Q2 '19 overstock. 20.0% $68 Q3 '19 20.7% $75 Q4 '19 21.9% $74 Q1 '20 23.2% $178 Q2 '20 Note: All figures represent results from continuing operations. 23.5% $169 Q3 '20 22.5% $151 Q4 '20 23.3% $154 Q1 '21 Gross Margin (%) 22.0% $175 Q2 '21 25% 20% 15% 10% 5% -0% Q2 Dynamics ■ Gross margin of 22.0% -119 bps vs. Q2'20 +228 bps vs. Q2'19 ▪ Gross margin impacted by: Normalized promotional and operating environment 9#10G&A and Tech Expense G&A and Tech Expense ($M) $80 $70 $60 $50 $40 $30 $20 $10 $- 14.1% $52 Q2 '19 overstock. + 14.1% $48 14.4% $52 15.8% 1 15.1% $54 $57 7.5%² 6.5% $59 8.2% G&A and Tech Exp. % of Revenue (%) Q3 '20 $54 8.1% $53 Q4 '20 8.1% $53 Q1 '21 6.7% 18% Q2 '21 16% 14% 12% 10% 8% 6% Q4 '19 Q1 '20 Q3 '19 Q2 '20 Note: All figures represent results from continuing operations. 1 In Q1'20 we recorded $2.5M in a special item 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 $49.9M, or 6.5% of revenue. 4% 2% -0% Q2 Dynamics ■ ■ G&A and tech expense generating operating leverage -7% vs. Q2'20² +3% vs. Q2'19 G&A and tech expense % of revenue of 6.7% -78 bps vs. Q2'20² -738 bps vs. Q2'19 10#11Adjusted EBITDA Adj. EBITDA ($M) $60 $50 $40 $30 $20 $10 $- $(10) $(20) $(30) $(40) $(2) (0.7%) Q2 '19 overstock. $(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. Adjusted EBITDA is a non-GAAP financial measure. See reconciliation in appendix. $30 4.5% Q4 '20 + Adj. EBITDA Margin (%) $34 5.1% Q1 '21 $44 5.6% Q2 '21 1 8% 6% 4% 2% 0% (2%) (4%) Q2 Dynamics ■ ■ Adj. EBITDA of $44M --$5M vs. Q2'20 +$47M vs. Q2'19 Adj. EBITDA margin of 5.6% -79 bps vs. Q2'20 +625 bps vs. Q2'19 11#12Active Customers and Order Frequency Active Customers (M) 12 10 8 6 4 2 1.76 5.8 Q2 '19 overstock. 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 1.64 9.2 Q4 '20 Orders per Active Customer 1.66 9.9 Q1 '21 1.69 9.2 Q2 '21 2.0 1.5 1.0 0.5 Q2 Dynamics ■ Active customers of 9.2M Impacted by significant influx of new customers during peak of pandemic restrictions in Q2'20 +31%/ +2.2M vs. Q2'20 +58% / +3.4M vs. Q2'19 ■ Order frequency of 1.69. Influenced by shift into home categories +4% vs. Q2'20 -4% vs. Q2'19 Note: Active customers represents the number of customers who made at least one purchase during the prior twelve-month period. 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. 12#13Orders and Average Order Value Orders Delivered (LTM) (M) 20 18 16 14 12 10 8 6 4 2 $166 10.2 Q2 '19 overstock. $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 15.1 $168 Q4 '20 Average Order Value 16.5 $183 Q1 '21 Note: LTM orders delivered represents the total number of orders delivered during the prior twelve-month period. Average order value represents net revenue divided by orders delivered, measured on a quarterly basis. $213 15.5 Q2 '21 $250 $200 $150 $100 $50 H$- Q2 Dynamics ■ ■ Orders delivered (LTM) of 15.5M +36% / +4.1M vs. Q2'20 +52% / +5.3M vs. Q2'19 Average order value of $213 Driven by sales mix of home furniture categories +33% vs. Q2'20 +28% vs. Q2'19 13#14overstock. Business Updates 14#15Oloverstock TM 15#16Top 4 Brand in a Growing -$325B 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 33% Jun 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. 16#17Establishing Unique Market Positioning Dream Homes for All: The space of 'Smart Value' where quality & style costs less Value + overstock. IKEA Oloverstock "Smart Value Seekers" Savvy Shoppers Home Goods Expertise Amazon Walmart Reluctant Refreshers 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 17#18Brand Pillars: Product Findability overstock. AA Departments Furniture Rugs Decor Bed & Bath Home Improvement Kitchen Outdoor Jewelry Apparel Kids & Baby overstock.com > 8 January 2021 > > > > > > > 1.0 AA Categories Furniture Rugs Decor Bed & Bath Home Improvement Kitchen Outdoor Lighting overstock.com Kids & Baby More Categories by June 2022 > > > > > > > > > Home vs. Non-Home Customers: 28-day-spend Higher Purchase & Post-purchase NPS Higher Repeat Rate Our focus on Home attracts loyal customers who spend more with us Higher 18#19Brand Pillars: Smart Value Sale Ends in 2 Days See website for details. overstock. % off coupons free shipping on EVERYTHING extra % off* Smart Value = best quality for the price Promotional model is critical to target customers Competitive pricing is foundational to brand Free shipping is a top purchase driver 19#20Brand Pillars: Easy Delivery and Support overstock. Distribution Center DC Assignment Destination ZIP Delivery speed and on-time accuracy drive customer satisfaction and retention Frequent communications enable navigation of supply chain disruptions Deep partner base enables high inventory and broad assortment -3,000 Third-party manufacturers, distributors, and other partners ~5,000 Fulfillment centers 20#21Brand Pillars: Easy Delivery and Support Our mission is to deliver predictable and efficient customer journeys Aim to resolve issues on first contact Customers prefer self-service options. overstock. "The person that assisted me was brilliant! She was informative, kind, patient with me..." "The agent from the customer care team did a great job understanding and resolving my issue quickly..." WINNER BEST OF STATE UTAH 2021 700 Forbes America's Best Mid-size Employers 2021 LOYALTY 360 The association for customer loyalty 21#22Growth Drivers overstock. Increase brand association with "home" Establish government business Å A Improve Co customer retention Improve product findability Q Optimize marketing channels 西 Increase home assortment Expand internationally Increase mobile app adoption 22#23Well-Positioned for Market Share Growth in 2021 and Beyond ▪ Revenue 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 — overstock. dream homes for all Driving sustainable, profitable market share growth 23#24Medici Ventures Fund C 24#25Medici Ventures Fund Update tZERO: - - Announced digital securities that plan to trade on the tZERO ATS, including American Films (AMFL), EnergyFunders, Liquid Mining Funds, and NYCE Partnered with Wazuzu to bring NFTs to market Launched new tZERO Crypto App (2.0) with higher buy limits and instant settlement Capital raise in process Hosting Q2 update call in August overstock. 25#26overstock. Summary and Q&A 26#27Q2 Review and Looking Ahead ■ Released tax valuation allowance Deconsolidated Medici businesses and recorded gain on adjustment to fair value Executing against our focused strategy Operating in a large and growing market with favorable long-term trends Continuing to deliver sustainable, profitable market share growth overstock. 27#28Questions? To ask questions: Dial-in: (877) 673-5346 Conference ID: 9394705 Email: [email protected] ■ overstock. 28#29overstock. Appendix 29#30Adjusted 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 Severance Transaction costs Total Special items Jun-2019 Sep-2019 GA (13,230) $ (13,448) $ (16,740) $ (13,766) $ 6,127 6,212 6,474 5,569 4,560 3,821 3,911 2,681 (458) (321) (182) 11 419 183 (65) 287 136 160 (100) 163 (1,486) (6,541) $ (2,446) $ $ Three months ended Dec-2019 Mar-2020 Jun-2020 Sep-2020¹ Dec-2020¹ Mar-2021 (1,221) (4,614) $ (1,221) $ (1,221) $ (6,702) $ $ (2,501) $ 1,015 (1,486) $ 47,839 $ 38,050 $ 23,092 $ 26,018 $ 5,409 5,310 5,487 5,146 1,952 1,568 1,640 2,305 364 264 199 155 (246) (59) (595) 226 840 (7,272) 48,886 $ (335) 432 29,920 $ 193 (187) 33,856 $ (7,272) $ (7,272) $ 607 288 46,028 $ 288 288 $ 432 $ loverstock. GAAP financial measures. Review our financial statements and publicly-filed reports in their entirety and do not rely on any single financial measure. Jun-2021 432 $ (187) $ (187) $ 82,405 4,803 2,802 130 (298) (45,726) 243 44,359 Note: All figures represent results from continuing operations, in thousands. 1 Period does not yet reflect certain immaterial income tax reclassifications associated with discontinued operations. No impact to adjusted EBITDA. 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 243 243 30#31Adjusted Diluted EPS Reconciliation Numerator: Income from continuing operations Less: Preferred stock dividends -- accumulated Undistributed income from continuing operations Less: Undistributed income allocated to participating securities Net income from 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. $ SA Three months ended June 30, 2021 Less: tax valuation allowance release Diluted EPS Note: All figures represent results from continuing operations, in thousands, except per share data. 82,405 182 82,223 7,882 74,341 43,314 $ $ 1.72 $ 47,046 47,046 4,510 42,536 43,314 0.99 $ $ CA Adjuste d Diluted EPS 35,359 182 35,177 3,372 31,805 43,314 0.73 31