#1O overstock. Q1 2023 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, 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, and in our subsequent filings with the SEC. The Form 10-K 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 Outlook 4. Q&A 3#4Oloverstock. CEO Remarks#52023: 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 5#6Home-only Active Customers Above 2019 Levels LTM home-only¹ active customers Home-only active customers above 2019 pre-pandemic levels Pre- Pandemic 4.2 FY '19 overstock. LTM home-only active customers (In Million) 8.0 7.3 FY '20 FY '21 5.1 I FY '22 4.8 Q1'23 LTM home-only¹ active customers - QoQ Change Active customer declines moderating 2,000 1,500 1,000 500 0 -500 -1,000 FY '19 Q1 '20 Change in LTM home-only active customers (In 000s, QoQ change) Q2 '20 Q3 '20 FY '20 Q1 '21 Pandemic comparison begins Q2 '21 Q3 '21 FY '21 Q1 '22 Net customer declines moderating Q2 '22 1 Home-only customers represent customers who have shopped home categories over the last twelve months. Home customers that have also shopped non-home categories have not been excluded. Q3'22 FY '22 -281 Q1'23 CO 6#7Medici Ventures Fund Update Medici Ventures Day - May 31, 2023 tZERO GRAN overstock. CHAIN SettleMint PEERNOVA Recent Updates MEDICI LAND GOVERNANCE FinClusive bitt GRAIN 7#8Corporate Update ▪ New Independent Board member - Joanna Burkey (CISO, HP Inc.) ▪ Annual Shareholder Meeting on May 18 ▪ 'Your Home, Your Treasure' overstock. Sale $231.64 Hopper Studio Sophia Grey Nightstand Sale Starts at $184.49 Middlebrook 25-inch Modern 2-drawer Storage ✰✰✰✰✰ Sale $171.89 Middlebrook Modern Gallery Top Solid Wood ✰✰✰✰✰ Sale $343.79 Middlebrook Modern 2- Drawer USB Nightstand, ✰✰✰✰✰ Starts at $324.49 Middlebrook Solid Wood Modern 1-Drawer $219.99 Avenue Greene Leeds 2 Drawer Nightstand ✰✰✰✰✰ Beautiful Finds for Every Room Starts at $49.99 Watermark Geometric Print Place Mat (Set of 4) ✰✰✰✰✰ your home, your treasure Find the perfect something at the perfect price. Shop Current Sale 8#9Oloverstock. Financial Results TM 9#10Q1 2023 Financial Results Revenue $381.1 Million -29% vs. Q1'22 Adjusted EBITDA Margin ¹ 0.9% -311 bps vs. Q1'22 overstock. Gross Margin 23.5% +18 bps vs. Q1'22 Diluted EPS -$0.23 Adjusted Diluted EPS² -$0.10 -$0.31 vs. Q1'22 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 estimated tax impact from equity method activity. See reconciliation in appendix. G&A and Tech % of Revenue 13.4% +327 bps vs. Q1'22 Expenses -6% / -$3M vs. Q1'22 Ending Cash $374.7 Million +1% +$3.5M vs. Q4'22 10#11Revenue $700 $600 $500 $400 $300 $200 $100 $0 Revenue ($M) $363 Q1 '19 loverstock. $340 Q1 '20 $660 Q1 '21 $536 Q1 '22 Note: All figures represent results from continuing operations. $528 Q2'22 -29% $460 Q3 '22 $405 Q4 '22 $381 Q1 '23 Q1 Dynamics ■ Revenue of $381.1M -29% /-$155M vs. Q1'22 -27% home-only vs. Q1'22 Revenue influenced by: Macro / consumer sentiment Non-home category exit 11#12Gross Margin $225 $200 $175 $150 $125 $100 $75 $50 $25 $0 Gross Margin ($M) 19.9% $72 Q1 '19 loverstock. 21.9% $74 Q1 '20 23.3% $154 Q1 '21 23.4% $125 Q1 '22 Note: All figures represent results from continuing operations. 22.9% $121 Q2 '22 23.3% $107 Q3 '22 22.1% $90 Q4 '22 Gross Margin (%) 23.5% $90 Q1 '23 25% 20% 15% 10% 5% 0% Q1 Dynamics ■ Gross margin of 23.5% +18 bps vs. Q1'22 ▪ Gross margin influenced by: Merchandising actions. Operational efficiencies Higher discounting 12#13G&A and Tech Expense $80 $70 $60 $50 $40 $30 $20 $10 $0 G&A and Tech Expense ($M) 15.9% $58 Q1 '19 overstock. 15.8% 1 15.1% $54 $51 1 $53 8.1% Q1 '21 $54 10.1% Q1 '22 $52 9.8% $48 Q2 '22 10.5% Q3 '22 G&A and Tech Exp. as % of Revenue $47 11.5% Q4 '22 $51 13.4% Q1 '23 20% 18% 16% 14% 12% 10% 8% 6% Q1 '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 and tech expense in Q1'20 was $51.2M or 15.1% of revenue. 4% 2% 0% Q1 Dynamics G&A and Tech Expense of $51M -6% vs. Q1'22 ■ - G&A and Tech Expense % of revenue of 13.4% - 327 bps de-leverage vs. Q1'22 13#14Adjusted EBITDA $50 $40 $30 $20 $10 $0 Adjusted EBITDA ($M) ($10) (2.2%) 5.1% 4.0% $34 $21 li (1.9%) ($7) ($8) Q1 '19 Q1 '20 Q1 '21 Q1 '22 overstock. Note: All figures represent results from continuing operations. 3.9% $21 Q2 '22 3.2% $15 Q3 '22 Adjusted EBITDA Margin (%) 1.6% $7 Q4 '22 0.9% $3 Q1 '23 6% 4% 2% 0% (2%) (4%) Q1 Dynamics ■ ■ Adj. EBITDA of $3M - -$18M vs. Q1'22 Adj. EBITDA margin of 0.9% -311 bps vs. Q1'22 14#15Active Customers and Order Frequency 12 10 8 6 2 0 Active Customers (LTM) (M) 1.75 6.2 Q1 '19 overstock. 1.70 5.2 1.66 9.9 1.67 7.4 1.65 6.5 Order per Active Customer (LTM) 1.62 5.8 1.60 5.2 1.57 4.8 2.0 1.5 1.0 0.5 0.0 Q1 '22 Q2 '22 Q3 '22 Q4 '22 Q1 '23 Q1 '20 Q1 '21 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. Q1 Dynamics ■ Active customers of 4.8M -35% / -2.6M vs. Q1'22 - - -29% Home-only vs. Q1'22 Macro / consumer sentiment Non-home category exit Order frequency of 1.57 - -6% vs. Q1'22 Home-only strategy 15#16Orders and Average Order Value Orders Delivered (LTM) (M) 25 20 15 10 LO 5 0 $155 10.9 Q1 '19 loverstock. $156 8.8 $183 16.5 $221 12.3 $247 10.7 $243 9.4 Average Order Value $215 8.2 Q1 '20 Q1 '22 Q2 '22 Q3 '22 Q4 '22 Q1 '21 Note: LTM orders delivered represents the total number of orders delivered during the prior twelve-month period. Note: Average order value represents net revenue divided by orders delivered, measured on a quarterly basis. $220 7.5 Q1 '23 $250 $200 $150 $100 $50 $0 Q1 Dynamics Orders delivered (LTM) of 7.5M - -39% / -4.8M vs. Q1'22 ■ ■ Average order value of $220 Relatively flat vs. Q1'22 16#17Home-only Active Customers and Revenue Q1 LTM Active Customers Change Reported -35% YoY Excluding non-home only¹ customers -29% YoY ■ 0% H -5% -10% -15% -20% -25% -30% -35% -40% -12% -9% -26% -23% overstock. -29% -26% -29% -33% -31% -36% -29% -35% Q4 '21 Q1 '22 Q2 '22 Q3'22 Q4'22 Q1'23 H Actual/ Reported ■ Excluding non-home only customers Q1 Revenue Change Reported -29% YoY Excluding non-home only¹ customers -27% YoY 0% H -5% -10% -15% -20% -25% -30% -35% -40% ""|||||| -16% -30% -31% -9% -5% Q4 '21 -19% Q1 '22 -34% -33% -30% -34% Q2 '22 Q3'22 Q4'22 -27% -29% Q1'23 Actual/ Reported Excluding non-home only customers 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. 17#18Q1 2023 Balance Sheet Highlights overstock. Cash $375 Million +1%/ +$3M vs. Q4'22 Net Cash Position ¹ $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 Grain Chain funding round 18#1919 All 111 20 mill Hi!!! A 450A 1 CULTUR K hitar Ch Wa FOUGHT HIELT FALM 5 SLO VAST THE TM Updates Business Ooverstock.#20Key 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 20#21Business Updates 200 product findability get inspired anywhere, but easily find it at Overstock overstock. smart value quality & style for less Strengthened loyalty offerings with co-brand credit card launch Expanded home product assortment, exceeding internal expectations Improved delivery messaging accuracy and delivery times easy delivery + support fast, free, & predictable delivery, plus low-hassle returns & support 21#22Targeted 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. 22#23Oloverstock. Q&A 23#24overstock. To ask questions: Access registration link on IR website Email: [email protected] Questions? 24#25O overstock TM#26overstock. Appendix 26#27Adjusted EBITDA Reconciliation Net income (loss) 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 loverstock. $ $ 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 Three months ended Mar-2022 32,942 $ 4,232 3,484 132 (12,507) (1,447) 511 27,347 $ 502 9 511 $ 10,123 $ 4,307 4,639 125 114 2,092 53 21,453 $ 53 53 $ Jun-2022 7,147 4,043 4,695 (115) 1,981 2,529 475 20,755 $ 471 $ 4 475 Sep-2022 (36,995) $ 4,130 4,056 (976) 46,283 (2,653) 923 14,768 $ 27 $ 878 18 923 $ Dec-2022 (15,511) $ 4,226 4,928 (1,999) 15,447 (584) 6,507 $ Mar-2023 (10,307) 5,985 5,795 (2,559) 7,389 (2,887) 3,416 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. 27#28Adjusted Diluted EPS Reconciliation in thousands, except per share data Numerator: Net loss attributable to common stockholders Denominator: Weighted average shares of common stock outstanding-diluted Net loss per share of common stock: Diluted overstock. Diluted EPS $ (10,307) S 45,067 Three months ended March 31, 2023 Less: equity method income/(loss) ¹ $ (0.23) $ Note: All figures represent results from continuing operations, in thousands, except per share data. 1 Inclusive of estimated tax impact from equity method activity. (5,609) 45,067 Adjusted Diluted $ (0.13) $ EPS (4,698) 45,067 (0.10) 28