#1Oloverstock. Q3 2021 Earnings Call#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 difficulties we may have with our fulfillment partners, supply chain, access to products, shipping costs, attraction/retention of employees, search engine optimization results, payment processors, infrastructure, including any cyber-attacks or data breaches affecting us or any of them, 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, 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, our Form 10-Q for the quarter ended June 30, 2021, which was filed with the SEC on August 5, 2021, and in our subsequent filings with the SEC. The Form 10-K, Form 10-Q's, 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#4Macro Trends and Business Model Support Long-Term Favorability Solid Macro Trends 1 in 10¹ Americans moved in 2020 1/3³ of home furnishings purchased online in 2020 6%* 2021 forecasted U.S. GDP growth 5%² 2021 forecasted U.S. home sales growth overstock. 5 8%$ 2021 forecasted U.S. consumer spending growth Distributed Supply Chain (Partner Network) 1 Source: Online survey conducted by Harris Poll on behalf of Zillow, March 2021. 2 Source: Zillow August 2021-August 2022 Home Value & Sales Forecast, September 2021. 3 Source: Combined data from eMarketer, NRF, NPD, and Earnest transactional data. + Asset-light (Drop-Ship Model) 4 Source: International Monetary Fund, October 2021. 5 Source: Deloitte - U.S. Economic Forecast, September 2021. = Long-term Favorability 4#5Corporate Update ■ Announced $100 million stock repurchase program Utah District Court dismissed with prejudice securities class action lawsuit Announced national Charitable Partnership with Mercy Housing overstock. mercy HOUSING 5#6overstock. Financial Results 6#7Q3 2021 Financial Results Revenue $689.4 Million -4% vs. Q3'20 +102% vs. Q3'19 Adjusted EBITDA¹ $36.1 Million -$9.9M / -22% vs. Q3'20 +$40.7M / +882% vs. Q3'19 overstock. Gross Margin 22.7% -78 bps vs. Q3'20 +270 bps vs. Q3'19 Diluted EPS $0.63 Adjusted Diluted EPS² $0.54 -$0.27 vs. Q3'20 +$0.94 vs. Q3'19 Note: All figures represent results from continuing operations. 1 Adjusted EBITDA is a non-GAAP financial measure. See reconciliation in appendix. 2 Excludes the impact of $4.4M tax valuation allowance release. See reconciliation in appendix. G&A and Tech % of Revenue 7.6% -59 bps vs. Q3'20 -653 bps vs. Q3'19 Ending Cash $512.2 Million 7#8Revenue $800 $700 $600 $500 $400 $300 $200 $100 $0 Revenue ($M) $341 Q3 '19 overstock $364- Q4 '19 +102% $340 Q1 '20 $767 Q2 '20 $718 Q3 '20 Note: All figures represent results from continuing operations. $670 Q4 '20 - 4% $660 Q1 '21 $795 Q2 '21 $689 Q3 '21 Q3 Dynamics ■ - Revenue of $689M -4% / -$28M vs. Q3'20 +102% / $349M vs. Q3'19 ~2x pre-pandemic sales run-rate 8#9Gross Margin $225 $200 $175 $150 $125 $100 $75 $50 $25 $0 Gross Margin ($M) 20.0% $68 Q3 '19 overstock 20.7% 21.9% $75 I Q4 '19 $74 Q1 '20 23.2% $178 Q2 '20 23.5% $169 Q3 '20 Note: All figures represent results from continuing operations. 22.5% $151 Q4 '20 23.3% $154 Q1 '21 22.0% $175 Q2 '21 Gross Margin (%) 22.7% $157 Q3 '21 25% 20% 15% 10% 5% 0% Q3 Dynamics ■ Gross margin of 22.7% -78 bps vs. Q3'20 +270 bps vs. Q3'19 ▪ Gross margin impacted by: Normalized promotional and operating environment 9#10G&A and Tech Expense G&A and Tech Expense ($M) $80 $70 $60 $50 $40 $30 $20 $10 $0 14.1% $48 Q3 '19 overstock. 14.4% $52 15.8% 1 15.1% $54 $57 7.5%² 6.5% $59 8.2% Q3 '20 $54 8.1% Q4 '20 $53 8.1% Q1 '21 G&A and Tech Exp. as % of Revenue $53 6.7% Q2 '21 $52 7.6% Q3'21 18% 16% 14% 12% 10% 8% 6% 4% Q4 '19 Q1 '20 Q2 '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. 2% 0% Q3 Dynamics ■ ☐ G&A and tech expense generating operating leverage -11% vs. Q3'20 +9% vs. Q3'19 G&A and tech expense % of revenue of 7.6% -59 bps vs. Q3'20 - -653 bps vs. Q3'19 10#11Adjusted EBITDA $60 $50 $40 $30 $20 $10 $0 ($10) ($20) ($30) ($40) Adjusted EBITDA ($M) ($5) (1.4%) Q3 '19 overstock ($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. $30 4.5% Q4 '20 $34 5.1% Q1 '21 Adjusted EBITDA Margin (%) $44 5.6% Q2 '21 $36 5.2% Q3 '21 10% 8% 6% 4% 2% 0% (2%) (4%) Q3 Dynamics ■ - Adj. EBITDA of $36M -$10M vs. Q3'20 +$41M vs. Q3'19 Adj. EBITDA margin of 5.2% -118 bps vs. Q3'20 +659 bps vs. Q3'19 11#12Active Customers and Order Frequency 12 10 8 6 2 0 Active Customers (LTM) (M) 1.76 5.4 Q3 '19 overstock. 1.75 5.1 1.70 5.2 1.62 7.0 1.63 8.2 1.64 9.2 Q4 '20 Order per Active Customer (LTM) 1.66 9.9 Q1 '21 1.69 9.2 Q4 '19 Q1 '20 Q2 '20 Q3 '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. Q2 '21 1.68 8.7 Q3 '21 Q3 Dynamics ■ Active customers of 8.7M Impacted by significant influx of new customers during the pandemic +5% / +0.4M vs. Q3'20 +59% / +3.2M vs. Q3'19 ▪ Order frequency of 1.68 Influenced by shift into home categories +3% vs. Q3'20 -5% vs. Q3'19 12#13Orders and Average Order Value 25 20 15 10 LO 5 0 Orders Delivered (LTM) (M) $167 9.6 Q3 '19 $155 8.9 $156 8.8 $160 11.3 $173 13.4 $168 15.1 $183 16.5 Average Order Value $213 15.5 Q1 '20 Q2 '20 Q3 '20 Q4 '20 Q1 '21 Q2 '21 Q4 '19 Note: LTM orders delivered represents the total number of orders delivered during the prior twelve-month period. overstock. Note: Average order value represents net revenue divided by orders delivered, measured on a quarterly basis. $214 14.5 Q3 '21 $250 $200 $150 $100 $50 $0 Q3 Dynamics ■ ■ Orders delivered (LTM) of 14.5M +8% / +1.1M vs. Q3'20 +51%/ +4.9M vs. Q3'19 Average order value of $214 Driven by sales mix of home furniture categories +24% vs. Q3'20 +28% vs. Q3'19 13#14overstock. Business Updates 14#15Oloverstock TM FIXE TAXE 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. 5. Target 6. Pottery Barn IKEA Bed Bath & Beyond 1. loverstock 8. 9. West Elm 10. Restoration Hardware overstock. 50% 40% 30% 20% 10% 0% 6% Furniture & Home Furnishings U.S. Online Penetration ² 7% 8% 9% 11% 13% 16% 18% 20% 23% 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 29% 2020 32% Sep 2022 2023 2021 (est.) (est.) (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 Ooverstock. "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. Our focus on Home attracts loyal customers who spend more with us. vs. 'Non-Home': Higher purchase & post-purchase Net Promoter Score -2.0x Average Order Value -1.5x Higher repeat rate 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. overstock overstock Delivery speed and on-time accuracy drive customer satisfaction and retention Frequent communications and planning enable navigation of supply chain disruptions Large and growing Home 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 A Alerts O Dashboard R Supplier Oasis Opportunity Compass overstock supplier oasis + Products Orders Inbound Shipments Outbound Shipments Returns al Reports https://edge supplieroasis.com/ Channels Tools Manage Users Opportunity Compass FULL CATALOG Not Optimized PARTNER PROGRAMS Search ☐☐☐ PRODUCT CONTENT Perary Optmont 11-piece Fish Tape Combo Drill Set-brown 440 16-piece High Speed Black Code Drill Bit Set-br 173023389 overstock. 16-ploce Titanium Coated High Speed Drill Bit Se 11-piece Fish Tape Combo Drill Set-brown24 A Alerts 16-piece High Speed Black Childe Drill Bit Set-br Supplier Oasis Dashboard Opportunity Compass overstock. supplier oasis Products Orders Inbound Shipments Outbound Shipments Returne Reports https://edge supplieroasis.com/ Channels Tools Manage Users Customer Service Requests 148 Search by Order Number Cancellation Request New Order: 12345676009 Changed my mind SKU 5123456000 PSKU 5123456000 Order: 12345676009 Changed my mind Documentation Request New SKU 5123456000 PSKU 5123456000 Q Late Due 6/12/2 SKU 5123456000 PSKU 5123456000 O Late Due 6/12/2 Alerts O Late Due 6/12/20 Invalid Tracking Number New Order: 12345676009 Changed my mind Cancellation Request Waiting for Partner HIGH TRAFFIC SKUS Dashboard Supplier Oasis Ooverstock. supplier oasis Opportunity Compass R Products Orders Inbound Shipments Outbound Shipments Export Full Catalog Returns Reports https://edge supplieroasis.com/ Channels Tools Manage Users Orders 36 Are you participating in our Back Orders program? Back order functionality allows customers to purchase em emporarily out of stock, or news that have not yet ved at your woune For more nation on eligby Back Ore Sale Cesep Ce Pending Shoe Expedted Orders Action Center Payment Summary Last Payment O looks ke you're all caught up 7-Day WISP $106.536 11 75% Cancellation Request New Late Sellable SKUs Count Refresh Prymer Detals Sales Summary Your To De YOY BER P Opportunity Compass Sales Compass Inventory O Uncompetitive O SALVE UN Content o 2 We provide robust analytics and compelling growth opportunities Yow To Date chết trong t 44% Not Optimized Accrual o Cave Love LDL 28 De FOR 1304 n Proprietary dashboards and analytics software Analytics support growth and business development opportunities Secures assortment and allocations 21#22Growth Drivers overstock. Improve product findability Optimize marketing channels Improve customer retention Increase brand association with "home" A Q Co Increase mobile app adoption 西 Increase home assortment Expand internationally Establish government business 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 24#25Medici Ventures Fund Update tZERO bitt overstock. ▪ Initiated trading of Exodus digital security (EXOD) on tZERO ATS Announced new digital securities planning to trade on tZERO ATS ■ Partnered with Wealth Block ▪ Launched support of eight new crypto assets on tZERO Crypto app ▪ Received FINRA approval to self-clear trades ▪ Announced it is CBDC technology provider to Central Bank of Nigeria ▪ Launched eNaira on October 25 25#26Medici Ventures Fund Update ripio MEDICI LAND GOVERNANCE ✔Voatz overstock. ▪ Raised $50M Series B funding ▪ Medici Ventures Fund increased its ownership percentage ■ Partnered to detect and reduce deed fraud in New York City Supported Michigan Democratic Party virtual convention PELION VENTURE PARTNERS 26#27overstock. Summary and Q&A 27#28Q3 Review and Looking Ahead ■ 10:10 overstock. Search Q Search Overstock Latest Offers Home Free Shipping on EVERYTHING!" labor day Shop Now → Continued focus on Overstock brand association with Home On target with removal of Non-home products from site Increased assortment of home product SKUs and strategic home brands. Outperformed peers in 'Outdoor Furniture' traffic and conversion Successfully executing an event-driven sales strategy Operating in a large and growing market with favorable long-term trends Distributed partner network enables supply chain flexibility throughout Holiday season and beyond Continuing to deliver sustainable, profitable market share growth Furniture Lists Shop By 70off 1000s of items' Notifications Rugs Deals 112/11 00 Departments 28#29Questions? To ask questions: Dial-in: (877) 673-5346 Conference ID: 7265079 Email: [email protected] ■ overstock. 29#30overstock. Appendix 30#31Adjusted 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 Transaction costs Total Special items overstock. $ Sep-2019 (13,448) $ 6,212 3,821 (321) 183 160 (1,221) (4,614) $ (1,221) $ (1,221) $ Dec-2019 (16,740) $ (13,766) $ 6,474 5,569 3,911 2,681 (182) (65) (100) Mar-2020 (6,702) $ 11 287 163 (1,486) (6,541) $ (2,501) $ 1,015 (1,486) $ Three months ended Jun-2020 47,839 $ 5,409 1,952 364 (246) 840 (7,272) 48,886 $ (7,272) $ (7,272) $ Sep-2020 Dec-2020¹ 37,904 $ 5,310 1,568 264 (59) 753 288 46,028 $ 288 288 $ 23,092 $ 5,487 1,640 199 (595) (335) 432 29,920 $ 432 $ 432 $ Mar-2021 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 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 GAAP financial measures. Review our financial statements and publicly-filed reports in their entirety and do not rely on any single financial measure. 30,426 4,383 2,542 139 79 (1,795) 305 36,079 1 253 51 305 31#32Adjusted Diluted EPS Reconciliation overstock. 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 $ $ $ Diluted EPS Note: All figures represent results from continuing operations, in thousands, except per share data. 30,426 182 30,244 2,899 27,345 43,324 0.63 Three months ended September 30, $ $ $ Less: tax valuation allowance release 4,420 4,420 424 3,996 43,324 0.09 $ $ $ Adjusted Diluted EPS 26,006 182 25,824 2,475 23,349 43,324 0.54 32