#1Oloverstock Q4 & FY 2021 Earnings Call TM OR#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, difficulties we may have with our fulfillment partners, supply chain, access to products, shipping costs, competition, macroeconomic changes, 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, problems with our infrastructure, including cyber-attacks or data breaches affecting us, adverse tax, regulatory or legal developments, 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, our Form 10-Q for the quarter ended September 30, 2021, which was filed with the SEC on November 4, 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 2. Financial Results 3. Business Updates 4. Summary and Q&A 3#42021-Year in Review +11% 2021 revenue growth on top of +74% in 2020 Revenue 2x 2019 run-rate Executed on brand pillars 2 consecutive years¹ of market share gains overstock. 94% home-related sales mix +250bps YoY. +740bps vs. 2019 SKU growth in home categories Increased brand association with home Improved customer metrics. 1 Source: Combined data from e Marketer, NRF, NPD, and Earnest transactional data. Compared to OSTK peer set. 2 Adjusted EBITDA Margin is a non-GAAP financial measure. See reconciliation in appendix. +40bps Adj. EBITDA margin2 expansion vs. 2020. +665bps vs. 2019 Disciplined spending Focused marketing efforts 7 consecutive quarters of profitability#5Business Model Supports Long-Term Favorability Expand Association Right to Win Relative with Home to Competition Large & growing TAM migrating online ¹ On track to reach 100% home-focused sales Driving higher and frequent purchases overstock. Promotional event-driven model Free-shipping top purchase driver Loyal customer base increasing spend 1 Source: eMarketer/ Insider Intelligence penetration and market size estimates as of February 2022. Leverage Unique Supply Chain Distributed and vast partner network Asset-light model lowers margin pressure Flexible fulfillment model#6Corporate Update Announced FORWARD Plan ▪ Paid preferred dividend ▪ Launched ESG site and increased efforts I - Charitable contribution to refugees resettling in Utah Donated home furnishings to support needs for Mercy Housing residents in Utah Committed to our We Are Overstock value to "do good" overstock. 6#7Ooverstock. Financial Results 1303 7#8Q4 2021 Financial Results Revenue $612.7 Million -9% vs. Q4'20 +68% vs. Q4'19 Adjusted EBITDA Margin ¹ 4.5% overstock. 0 bps vs. Q4'20 +630 bps vs. Q4'19 Gross Margin 22.7% +18 bps vs. Q4'20 +200 bps vs. Q4'19 Diluted EPS $0.68 Adjusted Diluted EPS² $0.36 -$0.12 vs. Q4'20 +$0.81 vs. Q4'19 Note: All figures represent results from continuing operations. 1 Adjusted EBITDA Margin is a non-GAAP financial measure. See reconciliation in appendix. 2 Excludes the impact of $2.3M tax valuation allow ance release and $13.3M equity method income. See reconciliation in appendix. G&A and Tech % of Revenue 8.4% +34 bps vs. Q4'20 -592 bps vs. Q4'19 Ending Cash $503.3 Million +2% / +$7.9M vs. 2020 +422%/ +$406.8M vs. 2019 8#9Revenue $800 $700 $600 $500 $400 $300 $200 $100 $0 Revenue ($M) $364 Q4 '19 $340 Q1'20 $767 Q2 '20 $718 +68% Q3'20 $670 Q4 '20 overstock. Note: Allfigures represent results from continuing operations. $660 Q1'21 $795 9% Q2 '21 $689 Q3 '21 $613 Q4 '21 Q4 Dynamics ■ Revenue of $613M -9% / -$57M vs. Q4'20 +68% / $249M vs. Q4'19 FY Dynamics Revenue of $2.8B +11%/ +$0.3B vs. 2020 +92% / +$1.3B vs. 2019 9#10Gross Margin $225 $200 $175 $150 $125 $100 $75 $50 $25 $0 Gross Margin ($M) 20.7% $75 Q4 '19 21.9% $74 Q1'20 23.2% $178 Q2 '20 23.5% $169 Q3'20 22.5% $151 Q4 '20 overstock. Note: Allfigures represent results from continuing operations. 23.3% $154 Q1'21 22.0% $175 Q2 '21 22.7% $157 Q3 '21 Gross Margin (%) 22.7% $139 Q4 '21 25% 20% 15% 10% 5% 0% Q4 Dynamics ▪ Gross margin of 22.7% +18 bps vs. Q4'20 - +200 bps vs. Q4'19 Gross margin influenced by: - ■ FY Dynamics ■ Gross margin of 22.6% -28 bps vs. 2020 +257 bps vs. 2019 Normalized promotional and operating environment vs. 2020 Operational efficiencies Gross margin influenced by: - Normalized promotional and operating environment vs. 2020 10#11G&A and Tech Expense $80 $70 $60 $50 $40 $30 $20 $10 $0 G&A and Tech Expense ($M) 14.4% $52 Q4 '19 overstock. 15.8%1 15.1% $54 $57 7.5%² 6.5% $59 8.2% $54 8.1% $53 8.1% Q1'21 $53 6.7% Q2 '21 G&A and Tech Exp. as % of Revenue $52 7.6% Q3 '21 $52 8.4% Q4'21 18% 16% 14% 12% 10% 8% 6% Q1'20 Q2 '20 Q3'20 Q4 '20 Note: Allfigures represent results from continuing operations. 1 In Q1'20 we recorded $2.5Min special items that benefited G&A expense. Reported G&A and tech expense in Q1'20 w as $51.2Mor 15.1% of revenue. 2 In Q2'20 we recorded $7.3Min special items that benefited G&A expense. Reported G&A and tech expense in Q2'20 w as $49.9Mor 6.5% of revenue. 4% 2% 0% Q4 Dynamics Stable G&A and tech expenses -5% vs. Q4'20 In line with Q4'19 ■ ■ - ■ G&A and tech expense % of revenue of 8.4% FY Dynamics Stable G&A and tech expenses -2% vs. 2020 In line with 2019 +34 bps vs. Q4'20 -592 bps vs. Q4'19 G&A and tech expense % of revenue of 7.6% -94 bps vs. 2020 -698 bps vs. 2019 11#12Adjusted EBITDA $60 $50 $40 $30 $20 $10 $0 ($10) ($20) ($30) ($40) Adjusted EBITDA ($M) ($7) (1.8%) ($7) (1.9%) $49 6.4% Q2'20 $46 6.4% Q3'20 $30 4.5% Q4 '19 Q1'20 overstock. Note: All figures represent results from continuing operations. Q4 '20 $34 5.1% Q1'21 $44 5.6% Q2 '21 Adjusted EBITDA Margin (%) $36 5.2% Q3 '21 $27 4.5% Q4'21 10% 8% 6% 4% 2% 0% (2%) (4%) Q4 Dynamics ▪ Adj. EBITDA of $27M -$3M vs. Q4'20 +$34M vs. Q4'19 Adj. EBITDA margin of 4.5% 0 bps vs. Q4'20 +630 bps vs. Q4'19 FY Dynamics Adj. EBITDA of $142M +$23M vs. 2020 +$163M vs. 2019 Adj. EBITDA margin of 5.1% +40 bps vs. 2020 +665 bps vs. 2019 12#13Active Customers and Order Frequency 12 10 8 6 2 0 Active Customers (LTM) (M) 1.75 5.1 Q4 '19 overstock. 1.70 5.2 1.62 7.0 1.63 8.2 1.64 9.2 1.66 9.9 Order per Active Customer (LTM) 1.69 9.2 1.68 8.7 1.67 8.1 Q3'20 Q4 '20 Q1'21 Q2 '21 Q3'21 Q4 '21 Q1'20 Q2 '20 Note: Active customers represents the total number of unique customers who have made at least one purchase during the prior tw elve-month period. Note: Orders per active customer represents the number of orders delivered over a tw elve-month period divided by the number of active customers for that same period. Q4 Dynamics ▪ Active customers of 8.1 M Impacted by significant influx of new customers during the pandemic ■ Exit of non-home categories during holiday/gifting period -12% -1.1M vs. Q4'20 +58% / +3.0M vs. Q4'19 Order frequency of 1.67 Improved association with home +2% vs. Q4'20 -4% vs. Q4'19 13#14Orders and Average Order Value 25 20 15 10 5 0 Orders Delivered (LTM) (M) $155 8.9 Q4 '19 overstock. $156 8.8 $160 11.3 $173 13.4 $168 15.1 $183 16.5 Average Order Value (AOV) $213 15.5 $214 14.5 Q2'20 Q3 '20 Q4 '20 Q1'21 Q2 '21 Q3'21 Q1'20 Note: LTM orders delivered represents the total number of orders delivered during the prior tw elve-month period. Note: Average order value represents net revenue divided by orders delivered, measured on a quarterly basis. $206 13.5 Q4 '21 $250 $200 $150 $100 $50 $0 Q4 Dynamics ■ Orders delivered (LTM) of 13.5M I -10% / -1.6M vs. Q4'20 +51%/ +4.6M vs. Q4'19 Average order value of $206 Driven by sales mix of home furniture categories +23% vs. Q4'20 +33% vs. Q4'19 - 14#15FY 2021 Financial Results Revenue $2,756.4 Million +11% vs. FY '20 +92% vs. FY'19 Adjusted EBITDA Margin ¹ 5.1% overstock. +40 bps vs. FY'20 +665 bps vs. FY'19 Gross Margin 22.6% -28 bps vs. FY'20 +257 bps vs. FY'19 Diluted EPS $3.57 Adjusted Diluted EPS² $2.19 +$0.07 vs. FY '20 +$4.00 vs. FY'19 Note: All figures represent results from continuing operations. 1 Adjusted EBITDA Margin is a non-GAAP financial measure. See reconciliation in appendix. 2 Excludes the impact of $53.8M tax valuation allow ance release and $13.3M equity method income. See reconciliation in appendix. G&A and Tech % of Revenue 7.6% -94 bps vs. FY'20 -698 bps vs. FY'19 Ending Cash $503.3 Million +2% / +$7.9M vs. 2020 +422%/ +$406.8M vs. 2019 15#16Ooverstock. JU Business Updates www O 16#17Top 4 Brand in a Growing ~$390B Market² Top U.S. Home Furnishings Online Brands¹ (ranked by online revenue) 1. Amazon 2. Wayfair 3. Walmart 4. Ooverstock. 5. Target 6. Pottery Barn IKEA Bed Bath & Beyond. 1. 9. West Elm 10. Restoration Hardware overstock. 40% 30% 20% 10% 0% 6% Furniture & Home Furnishings U.S. Online Penetration ² 7% 8% 10% 12% 14% 16% 19% 21% 24% 29% 30% 2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 33% 35% 2022 2023 (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: eMarketer/ Insider Intelligence penetration and market size estimates as of February 2022. 17#18Establishing 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. Show n 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 Click-Thru rate improvement = Higher engagement for h overstock. Speck N Out Cushions & P b pat Price $57.9 Save Sale $52.19 Spancing trip2 Wat Continued progress on search accuracy = Better relevancy outdoor patio outdoor patio furniture outdoor patio set outdoor patio rugs outdoor patio cushions outdoor patio chairs outdoor patio rug outdoor patio outdoor patio furniture covers outdoor patio sets outdoor patio furniture set sunbrella X Q Bradenton Sofa with Navy Cushions (73) Deals Try Clu Palm Harb Wicker Sta Chairs - Se Lad Focus on home and broad assortment = Higher spend O www Lacid 19#20Brand Pillars: Smart Value Record Cyber 5 sales Targeted mobile app campaigns Mobile app highest conversion platform Stronger repeat rates among app shoppers overstock. Latest Offers overstock.com Free Shipping on EVERYTHING!" 20off your order! Shop By We've Cooked Up a 20% off* Coupon Just for You! Enjoy your coziest holiday season yet! Dig into this season's exclusive savings by shopping the Overstock app. Your offer has been saved in your notification center. TODAY Only, Activate 20% off Limited Time Deals Never miss a deal with our app! Get App Limited-Time Deals Club O membership at highest level Loyal customers spend more club My Rewards club Earn on this Order: Available to Apply: O New loyalty program perks, same great benefits you love! Learn More About Points $3.07 (307 pts) $15.03 (1,503 pts) 20#21Brand Pillars: Easy Delivery & Support 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 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 떡 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 - overstock. dream homes for all Driving sustainable, profitable market share growth 23#24PELION VENTURE PARTNERS Medici Ventures Fund Update 24#25Medici Ventures Fund Update tZERO overstock. David Goone appointed new CEO ▪ Chief Strategy Officer of Intercontinental Exchange (NYSE: ICE) ▪ Starts in March 2022 Completed funding round ▪ Led by ICE, owner of New York Stock Exchange ▪ Medici Ventures Fund and OSTK participated in round Other key updates ▪ Launched clearance and settlement support for securities transactions ▪ Boston Security Token Exchange (BSTX) JV approved by SEC ▪ 18 crypto assets trading on crypto app as of December 2021 Legacy regulatory matters resolved - tZERO ATS and Speed Route ■ 25#26Medici Ventures Fund Update bitt MEDICI LAND GOVERNANCE overstock. PELION VENTURE PARTNERS ✔Voatz Medici Ventures Fund Day: To be hosted by Pelion on May 10 26#27Ooverstock. Summary and Q&A bot 27#282021 Review and Looking Ahead 2021 Review +11% Revenue growth on top of +74% in 2020. 2 consecutive years¹ of market share gains +40bps Adj. EBITDA margin² expansion vs. 2020. +665bps vs. 2019 overstock. Execute on Brand Pillars E Strengthen brand association with home Improve customer engagement Leverage unique fulfillment model 1 Source: Combined data from eMarketer, NRF, NPD, and Earnest transactional data. Compared to OSTK peer set. 2 Adjusted EBITDA Margin is a non-GAAP financial measure. See reconciliation in appendix. Business For the Long Term Continue to grow US market share Deliver profitability Replicate model in Canada and beyond 28#29overstock. To ask questions: Dial-in: (877) 673-5346 Conference ID: 3659278 ▪ Email: [email protected] I questions? 29#30Oloverstock TM overstock.#31overstock. Appendix 31#32Adjusted 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 $ $ Dec-2019 (16,740) $ 6,474 3,911 (182) (65) (100) (6,702) $ 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 Three months ended Dec-2020 37,904 $ 5,310 1,568 264 (59) 753 288 46,028 $ 288 288 $ 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 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 Note: All figures represent results from continuing operations, in thousands. GAAP entirety do rely on any single financial measure. overstock. At financial measures. Review our financial statements and publicly-filed repous in the with first to presented in accordance with GAAP and should not be relied upon to the exclusion of 32#33Adjusted Diluted EPS Reconciliation in thousands, except per share data Numerator: Income from continuing operations Less: Preferred stock dividends accumulated Denominator: Weighted average shares of common stock outstanding-diluted Undistributed income from continuing operations Less: undistributed earnings allocated to participating securities Net income form continuing operations attributable to common stockholde $ Net income from continuing operations per share of common stock: Diluted $ overstock. $ $ Diluted EPS 32,942 182 32,760 3,140 29,620 43,370 Less: tax valuation 1 release ¹ $ $ $ 0.68 $ Three months ended December 31, 2021 Note: All figures represent results from continuing operations, in thousands, exceptper share data. 1 Inclusive of deferred tax im pact from equity method income. 2 Inclusive of current tax impact from equity method expense. 2,341 2,341 224 2,117 43,370 0.05 Less: equity method income² $ $ $ 13,310 13,310 1,392 11,918 43,370 0.27 Adjusted Diluted $ $ $ $ EPS 17,291 182 17,109 1,524 15,585 43,370 0.36 33