#1Ooverstock. March 2023 Investor Presentation 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, 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, global conflict including the ongoing 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 further restrictions on the use of "cookies" or other tracking technologies, any negative business impacts associated with our evolving business practices including our 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, 2022, which was filed with the SEC on February 24, 2023, and in our subsequent filings with the SEC. The Form 10-K, Form 10-Qs, 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#3Overstock Overview ▪ 20+ years of innovation and technical expertise in e-commerce Disciplined and focused management team Strategically positioned within competitive landscape ■ Total addressable market and online penetration growing ▪ Foundational operational improvements driving stability Nimble, asset-light, drop-ship model ▪ Distributed supply chain with vast partner network ■ ■ overstock. making dream homes come true 3#4Experienced Management Team overstock. Jonathan Johnson III Director & CEO overstock. MEDICI David Nielsen President overstock. Carlisha Robinson Chief Product Officer volusion bmc P Payless SHOESOURCE Adrianne Lee Chief Financial Officer BEST BUY Hertz Carter Lee Chief People Officer overstock. Tushon Robinson Chief Supply Chain Officer Bractlet pitney bowes Angela Hsu Chief Marketing Officer LAMPS PLUS News Corp H. E. Glen Nickle Chief Legal Officer & Corporate Secretary overstock. ICON Joel Weight Chief Technology Officer MEDICI access 4#5Seasoned and Diverse Board of Directors Allison Abraham Chairwoman & Independent Director Village The Newton School. *** BE THE MOTION Robert Shapiro Independent Director SONECON GEORGETOWN UNIVERSITY overstock. Jonathan Johnson III Joseph Tabacco, Jr. Director & CEO Independent Director overstock. MEDICI William Nettles, Jr. Independent Director INVICTUS SUNGEVITY BERMAN IN TABACCO Barbara Messing Independent Director Walmart ROBLOX Barclay Corbus Independent Director Clean Energy WRHAMBRECHT+CO Joanna Burkey Independent Director hp SIEMENS Committees of the Board Audit Committee ▪ Allison Abraham (Chair) ■ Robert Shapiro William Nettles, Jr. Compensation Committee Barclay Corbus (Chair) ▪ Barbara Messing ▪ Joseph Tabacco, Jr. Nominating & Corporate Governance Committee ■ Joseph Tabacco, Jr. (Chair) ▪ Barbara Messing Barclay Corbus 5#6ESG Overview - Goals Accomplished in 2022 옴 diversity & inclusion environmental sustainability Investigate and establish renewable energy options for our Overstock-operated fulfillment centers. Evaluate and participate in the EPA Smartway Programs for Shippers. Create a measurable recyclable packaging material program within our fulfillment centers. Xeriscape 15,000 square feet of grass at our campus to reduce water consumption. overstock. Increase completion of diversity and inclusion training for all management employees. Achieve parity in engagement rates among all employee demographic groups, which reflect the level of enthusiasm and dedication the employees feel towards their jobs. corporate philanthropy Support the needs of hundreds of homes every year through our nonprofit partners. Provide hundreds of volunteer hours in our local communities through our Company Volunteer Time Off (CVTO) Program. human & employee rights Provide information to suppliers on improving performance in human rights. Offer new human rights training for employees. E governance Draft Vendor Code of Conduct. 6#7ESG Overview - 2023 Goals environmental sustainability 옴 Increase the percent of packing boxes made from recycled materials in our Overstock-operated fulfillment centers. Implement plastic and aluminum recycling programs at our Overstock-operated fulfillment centers. Implement a glass recycling program at our corporate headquarters. overstock. diversity & inclusion Increase the percentage of diverse managers who have a career mentor. corporate philanthropy Support the needs of hundreds of homes. Provide hundreds of volunteer hours in our local communities. human & employee rights Offer new anti-corruption training for employees. E governance Draft a company health and safety policy. 7#8Significant Progress Since Renewed Home-only Retail Focus Revenue vs. 2019 Home-only revenue +52% ¹ 1 Accelerated growth versus broader TAM² Home assortment +63% ³ Profitability vs. 2019 overstock. Operational improvements. enabled consecutive profitability 290 bps gross margin expansion ¹ 480 bps adj. EBITDA margin expansion¹ making dream homes come true™ 2020 to 2022 - Navigated shifting consumer sentiment and spending preferences. 2023 - Focused on key growth drivers to improve topline performance. 1. FY 2022 vs. FY 2019 2. Overstock home-only revenue compared to (a) Census furniture and home furnishings sales, (b) Home-related personal consumption expenditures and (c) eMarketer defined TAM. 3. December 2022 vs. December 2019 8#9Key Growth Drivers - Focus for 2023 & Beyond Increase brand association with "home" À Improve product findability Optimize marketing channels overstock. Improve customer retention overstock. Increase mobile app adoption Increase home assortment Grow Canada Improve category management Expected Outcomes Increase in order frequency ▪ Retain existing customers Acquire new customers ■ ▪ Gain market share Deliver on profitability targets ■ 9#10Notable Progress Made Since 2021 On Medici Ventures Recent Financing Rounds at Higher Valuations bitt GRA overstock. CHAIN SettleMint Additional Direct Investments To Drive Shareholder Value tZERO GRAIN CHAIN 10#11Ooverstock. Business Updates TM T S 11#12Unique Market Positioning Making Dream Homes Come True Smart Value = Quality & Style for less Overstock Customers Smart Value Seekers overstock. Savvy Shoppers Reluctant Refreshers Value ‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒ overstock. IKEA Home Goods Expertise Amazon Walmart 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. Wayfair West Elm Bed Bath & Beyond Pottery Barn Target Department Store Generalist Restoration Hardware Inspiration 12#132023: A Tale of Two Halves for Overstock Industry specific drivers Inflation, interest rates, housing market Inventory rationalization Discounting and promotional environment. ▪ Consumer demand I ▪ Domestic supply chain costs overstock. Overstock specific drivers ▪ Non-home revenue comparison ends Q2 2023 ▪ Newness in assortment ■ Expansion of loyalty efforts Strengthened operational leadership and teams Capitalize on build out of branded giftable assortment 13#14The Strategic Path Forward product findability get inspired anywhere, but easily find it at Overstock overstock. Cuisin smart value quality & style for less Improve website and search experience Increase brand engagement with new and exciting loyalty offerings Accelerate growth in mobile app penetration Enhance customer experience easy delivery + support fast, free, & predictable delivery, plus low-hassle returns & support 14#15Targeted Financial Operating Model ▪ 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 ▪ Positive free cash flow making dream homes come true Driving sustainable, profitable market share growth overstock. 15#16Ooverstock Financial Results TM TUOTT 116#17Q4 2022 Financial Results Revenue $404.9 Million -34% vs. Q4'21 Adjusted EBITDA Margin ¹ 1.6% -286 bps vs. Q4'21 overstock. Gross Margin 22.1% -54 bps vs. Q4'21 Diluted EPS -$0.34 Adjusted Diluted EPS² -$0.04 -$0.40 vs. Q4'21 G&A and Tech % of Revenue 11.5% +309 bps vs. Q4'21 Expenses -10% / -$5M vs. Q4'21 Ending Cash $371.3 Million -13% / -$56.3M vs. Q3'22 Note: All figures represent results from continuing operations. 1 Adjusted EBITDA Margin is a non-GAAP financial measure. See reconciliation in appendix. 2 Includes adjustment related to non-cash dividend related to preferred share conversion and tax impact of equity method activity. See reconciliation in appendix. 17#18Revenue $700 $600 $500 $400 $300 $200 $100 $0 Revenue ($M) $364 Q4 '19 overstock $670 Q4 '20 $613 Q4 '21 $536 Q1 '22 Note: All figures represent results from continuing operations. -34% $528 Q2 '22 $460 Q3 '22 $405 Q4 '22 Q4 Dynamics ■ Revenue of $404.9M -34%/-$208M vs. Q4'21 -30% Home-only vs. Q4'21 Revenue influenced by: Macro / consumer sentiment Non-home category exit 18#19Gross Margin Gross Margin ($M) $225 $200 $175 $150 $125 $100 $75 $50 $25 $0 ●20.7% $75 Q4 '19 22.5% $151 22.7% $139 Q4 '21 23.4% $125 Q4 '20 overstock. Note: All figures represent results from continuing operations. Q1 '22 22.9% $121 Q2 '22 23.3% $107 Q3 '22 Gross Margin (%) 22.1% $90 Q4 '22 25% 20% 15% 10% 5% 0% Q4 Dynamics ■ Gross margin of 22.1% -54 bps vs. Q4'21 ▪ Gross margin influenced by: Higher discounting Higher freight costs Leverage from merchandising actions 19#20G&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. $54 8.1% Q4 '20 $52 8.4% Q4 '21 $54 10.1% Q1 '22 Note: All figures represent results from continuing operations. $52 9.8% Q2 '22 G&A and Tech Exp. as % of Revenue $48 10.5% Q3 '22 $47 11.5% Q4 '22 20% 18% 16% 14% 12% 10% 8% 6% 4% 2% 0% Q4 Dynamics G&A and Tech Expense of $47M - -10% vs. Q4'21 ■ - G&A and tech expense % of revenue of 11.5% - De-leverage of 309 bps vs. Q4'21 20#21Adjusted EBITDA $50 $40 $30 $20 $10 $0 ($10) Adjusted EBITDA ($M) (1.8%) $30 4.5% $27 4.5% $21 4.0% ($7) Q4 '19 Q4 '20 Q4 '21 Q1 '22 loverstock. Note: All figures represent results from continuing operations. $21 3.9% Q2 '22 Adjusted EBITDA Margin (%) $15 3.2% Q3 '22 $7 1.6% Q4 '22 12% 10% 8% 6% 4% 2% 0% (2%) Q4 Dynamics ■ ■ Adj. EBITDA of $7M - -$21M vs. Q4'21 Adj. EBITDA margin of 1.6% -286 bps vs. Q4'21 21#22Active Customers and Order Frequency 12 10 8 6 2 0 Active Customers (LTM) (M) 1.75 5.1 Q4 '19 overstock. 1.64 9.2 1.67 8.1 1.67 7.4 Order per Active Customer (LTM) Q1 '22 1.65 6.5 1.62 Q2 '22 5.8 1.60 Q3 '22 5.2 2.0 Q4 '22 1.5 Q4 '20 Q4 '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. 1.0 0.5 0.0 Q4 Dynamics ■ Active customers of 5.2M -36% / -2.9M vs. Q4'21 - - -31% Home-only vs. Q4'21 Macro / consumer sentiment Non-home category exit Order frequency of 1.60 -4% vs. Q4'21 Home-only strategy 22#23Orders and Average Order Value 25 20 15 10 LO 5 0 Orders Delivered (LTM) (M) $155 8.9 $168 15.1 Q4 '19 $206 13.5 II Q4 '20 $221 12.3 $247 10.7 Average Order Value $243 9.4 Q4 '21 Q1 '22 Q2 '22 Q3 '22 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. $215 8.2 Q4 '22 $250 $200 $150 $100 $50 $0 Q4 Dynamics ▪ Orders delivered (LTM) of 8.2M - -39%/-5.3M vs. Q4'21 ■ Average order value of $215 +4% vs. Q4'21 Sales mix within home categories - 23#24Home-only Active Customers and Revenue Q4 LTM Active Customers Change Reported -36% YoY Excluding non-home only¹ customers -31% YoY ■ 0% -5% -10% -15% -20% -25% -30% -35% -40% -12% -9% Q4 '21 overstock. -23% -26% -26% -29% Q1 '22 Q2 '22 -33% -29% Q3'22 -31% -36% Q4'22 Actual/ Reported Excluding non-home only customers Q4 Revenue Change Reported -34% YoY Excluding non-home only¹ customers -30% YoY 0% -5% -10% -15% -20% -25% -30% -35% -40% -9% -5% Q4 '21 -16% -19% Q1 '22 -31% -34% Q2 '22 -30% -33% Q3'22 -30% -34% Q4'22 Actual/ Reported Excluding non-home only customers Home-only revenue trend stabilized 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. 24#25FY 2022 Financial Results Revenue $1.9 Billion -30% vs. FY'21 Adjusted EBITDA Margin ¹ 3.3% -185 bps vs. FY'21 overstock. Gross Margin 23.0% +34 bps vs. FY'21 Diluted EPS -$0.83 Adjusted Diluted EPS² $0.52 -$1.67 vs. FY'21 G&A and Tech % of Revenue 10.4% +278 bps vs. FY'21 Expenses -5% / -$10M vs. FY'21 Ending Cash $371.3 Million -13%-$56.3M vs. Q3'22 -26%/-$132.1 M vs. Q4'21 Note: All figures represent results from continuing operations. 1 Adjusted EBITDA Margin is a non-GAAP financial measure. See reconciliation in appendix. 2 Includes adjustment related to non-cash dividend related to preferred share conversion and tax impact of equity method activity. See reconciliation in appendix. 25#26Strong Balance Sheet Cash $371 Million -13%-$56M vs. Q3'22 overstock. ‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒ 1 Cash less long-term debt. Long-term Debt $34 Million -3% / -$1 M vs. Q3'22 No significant debt maturity until March 2030 ‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒ Share Repurchases $80 Million 1H 2022 $60M. Q4 2022 $20M ------ ------ ‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒ Strategic use of cash in FY 2022 tZERO Series B Funding $15 Million Q1 2022 and Q3 2022 investment tranches ‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒ ‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒ Net Cash Position ¹ $337 Million -14% / -$55M vs. Q3'22 ‒‒‒‒‒‒‒‒‒ 26#27PELION VENTURE PARTNERS Medici Ventures Fund Update 27#28Summary of 2021 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 28#29Medici Ventures Fund Portfolio Companies Identity/ Social MINDS NETKI evernym* FACTOM PROTOCOL overstock. * Exited Titling/ Smart Contracts Vis MEDICI LAND GOVERNANCE SettleMint Vital Chain Banking & Currency bitt spera ripio PEERNOVA FinClusive Capital Markets MI tZERO symbiont W WATCH DOG CAPITAL BANKORUS Supply Chain GRAN CHAIN Vinsent Voting ✔Voatz Votem 29#30Ooverstock TM#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 and other Severance Transaction costs Total Special items overstock. $ Dec-2020 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 Three months ended Dec-2021 30,426 $ 4,383 2,542 139 79 (1,795) 305 36,079 $ 1 $ 253 51 305 $ 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 $ Jun-2022 7,147 $ (36,995) $ 4,043 4,130 4,695 4,056 (115) (976) 1,981 2,529 475 20,755 $ 46,283 (2,653) 923 14,768 $ 471 $ Sep-2022 4 475 $ 27 $ 878 18 923 $ Dec-2022 (15,511) 4,226 4,928 (1,999) 15,447 (584) 6,507 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. 32#33Adjusted Diluted EPS Reconciliation in thousands, except per share data Numerator: Net loss from continuing operations attributable to common stockholders Denominator: Weighted average shares of common stock outstanding-diluted Net loss from continuing operations per share of common stock: Diluted overstock. $ SA Diluted EPS Note: All figures represent results from continuing operations, in thousands, except per share data. 1 Inclusive of estimated tax impact from equity method activity. (15,511) 45,420 (0.34) Three months ended December 31, 2022 Less: equity method income/(loss) ¹ (13,559) 45,420 (0.30) djusted Diluted EPS (1,952) 45,420 (0.04) 33