#1O overstock. 2023 Annual Stockholders Meeting 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, negative global economic consequences of global conflict, including the ongoing tensions between the United States and Russia, the United States and China, and other effects of the ongoing conflict in Ukraine, 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, our Form 10-Q for the quarter ended March 31, 2023, which was filed with the SEC on May 2, 2023, 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. Welcome and Call to Order 2. Forward-Looking Statements 3. Introductions 4. Notice of Meeting; Quorum Notice 5. Proposals 1-5 6. Closing of Polls 7. Preliminary Report of Voting Results 8. Adjournment of Meeting 9. Business Presentation 10. Q&A 3#4Overstock Board of Directors Allison Abraham Chairwoman & Independent Director Barbara Messing Independent Director overstock. Joanna Burkey Independent Director William Nettles Independent Director Barclay Corbus Independent Director Robert Shapiro Independent Director Jonathan Johnson Director & CEO Joseph Tabacco Independent Director 4#5Overstock Executive Team Jonathan Johnson Director & CEO Bret Mitchell Acting Chief Merchandising Officer overstock. David Nielsen President CH CH E. Glen Nickle Chief Legal Officer & Corporate Secretary MUL Angela Hsu Chief Marketing Officer H Carlisha Robinson Chief Product Officer H Adrianne Lee Chief Financial Officer Tushon Robinson Chief Supply Chain Officer Carter Lee Chief People Officer Joel Weight Chief Technol Officer LO 5#6KPMG Eric Denning Independent Auditor Computershare Douglas Ives Inspector of Elections CO 6#7Agenda overstock. 1. Welcome and Call to Order 2. Forward-Looking Statements 3. Introductions 4. Notice of Meeting; Quorum Notice 5. Proposals 1-5 6. Closing of Polls 7. Preliminary Report of Voting Results 8. Adjournment of Meeting 9. Business Presentation 10. Q&A 7#8Oloverstock. Business Presentation TM ww hel AKHLE יוניייי WWW COOK PAR 1914 ADA ADAIHAT 1400-18-01 ATRODEADTECUCHARE hoitamy w ²4, 8#9Corporate Update Simplified equity capital structure ▪ Executed share repurchases ▪ Investment in Medici Ventures portfolio ▪ Launched national brand campaign Upgraded leadership team ■ ■ overstock. [[| 9#10Strong Balance Sheet overstock. Cash $375 Million +1% / +$3M vs. Q4'22 Net Cash Position¹ $341 Million +1%/ +$4M vs. Q4'22 1 Cash less long-term debt. Long-term Debt $34 Million -1%/-$0.3M vs. Q4'22 No significant debt maturity until March 2030 Strategic Use of Cash $10 Million Q1 2023 GrainChain funding round 10#11Key Growth Drivers - Focus for 2023 & Beyond Improve product findability Optimize marketing channels overstock. Improve customer retention Increase brand association with "home" 盒 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 ■ ■ 11#12Targeted 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. 12#13To ask questions: Submit through the live portal questions? 13#14O overstock TM