#1Oloverstock Q4 & FY 2020 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 the effects of the novel coronavirus (COVID-19) and corresponding vaccines on market volatility, the world economy, government regulation, and our supply chain, including supply and demand for the products and services we offer, the ability of our third-party partners and carriers to provide products and services without interruption and at a reasonable cost, and customer comfort levels with purchasing from brick and mortar stores. Actual results could also differ materially for a number of reasons, including, but not limited to initiatives to improve or maintain the performance of our business, adverse tax, regulatory or legal developments, competition, and any inability to maintain profitability, continue to generate positive cash flow from operations, raise capital, or borrow funds on acceptable terms, difficulties we may have with our infrastructure, our fulfillment partners or our payment processors, including cyber-attacks or data breaches affecting us or any of them, any inability to protect our intellectual property, and difficulties we may experience with increasing or maintaining our search engine optimization results, converting web traffic to sales, or ensuring we maintain our new customer base. Other risks and uncertainties include, among others, whether our previously-announced arrangements with Pelion Venture Partners will be consummated, whether our partnership with Pelion will be able to achieve its objectives and the timing for doing such, the inherent risks associated with the businesses that Medici Ventures and tZERO are pursuing, including the effect of COVID-19 on capital markets, trading volatility, investor confidence, and willingness to invest in blockchain technologies, whether tZERO's initiatives with Box Digital Markets, LLC and tZERO Markets, LLC will be able to achieve their objectives and the timing for doing such, and the regulatory, technical, operational, and other obstacles tZERO faces in each of its initiatives. More information about factors that could potentially affect our financial results are included in our Form 10-K for the year ended December 31, 2019, which was filed with the SEC on March 13, 2020, in our Form 10-Q for the quarter ended March 31, 2020, which was filed with SEC on May 7, 2020, in our Form 10-Q for the quarter ended June 30, 2020, which was filed with the SEC on August 6, 2020, in our Form 10-Q for the quarter ended September 30, 2020, which was filed with SEC on November 5, 2020, 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 1. CEO Remarks 2. Financial Results 3. Business Updates 4. Summary and Q&A overstock. 3#4Corporate Update Partnership with Pelion Venture Partners. Limited Partnership Agreement announced in January Cash dividend declared on Series A-1 and Series B preferred shares $0.16 per share paid in December, fourth annual preferred dividend - Regulatory update New subpoena received in January Continue to operate well during COVID-19 pandemic - Working remote-first, monitoring vaccines, stimulus, and supply chain conditions overstock. 4#5Appointment of New CMO Elizabeth Solomon Chief Marketing Officer overstock. Formerly Head of Marketing for Amazon's Global Private Brands portfolio ▪ Extensive marketing leadership experience growing Fortune 100 companies ▪ Proven track record in growing, building, and repositioning brands through multi-channel and integrated marketing strategies I ▪ Previously with Samsung, Walmart, Cadbury, and Nestle ■ Joins team in late March 5#6overstock. Financial Results#7Q4 2020 Financial Results: Overstock.com, Inc. Revenue $684.0 Million +84% vs. Q4'19 Adjusted EBITDA1 $22.9 Million +$41.9M/+221% vs. Q4'19 1 Adjusted EBITDA is a non-GAAP financial measure. overstock. See Reconciliation in Appendix Gross Profit $153.0 Million +100% vs. Q4'19 Diluted EPS $0.26 +$0.99 vs. Q4'19 G&A % of Revenue 4.9% -410bps vs. Q4'19 Ending Cash $516.5 Million +$404.2M vs. Q4'19 7#8FY 2020 Financial Results: Overstock.com, Inc. Gross Merchandise Sales $3.2 Billion +74% vs. FY'19 G&A % of Revenue 5.0% -447bps vs. FY'19 1 Adjusted EBITDA is a non-GAAP financial measure. overstock. See Reconciliation in Appendix Revenue $2.5 Billion +75% vs. FY'19 Adjusted EBITDA1 $88.3 Million +$162M / +220% vs. FY'19 Gross Profit $579.5 Million +98% vs. FY'19 Diluted EPS $1.24 +$4.70 vs. FY'19 8#9Q4 2020 Financial Results: Overstock Retail Revenue $669.7 Million +84% vs. Q4'19 OpEx as % of Revenue 18.5% -563bps vs. Q4'19 1 Adjusted EBITDA is a non-GAAP financial measure. overstock. See Reconciliation in Appendix Gross Margin 22.5% +182bps vs. Q4'19 Adjusted EBITDA1 $34.2 Million +$36.4M vs. Q4'19 Dynamics I ■ ■ I Business model scaled +94% new customer growth YoY Gross margin expanded Structural improvements coupled with unique items Operating leverage generated - Revenue grew by 84% while operating expense grew by 41% Profitability delivered Margin profile remains consistent with long-term targets 9#10FY 2020 Financial Results: Overstock Retail Gross Merchandise Sales $3.2 Billion +74% vs. FY'19 OpEx as % of Revenue 18.3% -483bps vs. FY'19 1 Adjusted EBITDA is a non-GAAP financial measure. overstock. See Reconciliation in Appendix Gross Margin 22.9% +280bps vs. FY'19 Adjusted EBITDA¹ $135.6 Million +$139.3M vs. FY'19 10#11Retail Revenue Revenue ($M) $800 $700 $600 $500 $400 $300 $200 $100 $- F $363 (18%) Q1 '19 overstock. $367 (23%) Q2 '19 $341 (22%) Q3 '19 $364 (19%) Q4 '19 $340 (6%) Q1 '20 $767 109% Q2 '20 $718 111% Q3 '20 YOY Revenue A (%) $670 84% Q4 '20 120% 100% 80% 60% 40% 20% 0% (20%) H (40%) Q4 Dynamics ■ Revenue of $670M +$306M YOY +84% YoY ■ New customer growth +94% YoY ■ New customer repeat rate +6% YoY -2/3 of new customers in target segments 2020 Dynamics Revenue of $2.5B +$1.1B YOY +74% YoY 11#12Retail Gross Margin Gross Profit ($M) $225 $200 $175 $150 $125 $100 $75 $50 $25 $- 19.9% $72 Q1 '19 overstock. 19.7% $72 Q2 '19 20.0% $68 Q3 '19 20.7% $75 Q4 '19 21.9% $74 Q1 '20 23.2% $178 Q2 '20 23.5% $169 Q3 '20 Gross Margin (%) 22.5% $151 Q4 '20 25% 20% 15% 10% 5% H 0% Q4 Dynamics ■ ■ Gross margin of 22.5% +182bps YoY 2020 Dynamics ■ Gross margin impacted by operational efficiencies Gross profit of $571M +$283M YOY Gross margin of 22.9% +280bps YoY 12#13Retail OpEx as % of Revenue Operating Expense ($M) $140 $120 $100 $80 $60 $40 $20 $- H $85 23.5% Q1 '19 overstock. $82 22.2% Q2 '19 $78 22.8% Q3 '19 $88 24.1% Q4 '19 $83 24.4% Q1 '20 $1321 17.2% 1 16.3% Operating Expense % of Revenue (%) Q2 '20 $125 17.5% Q3 '20 $124 18.5% Q4 '20 50% 45% 40% 35% 30% 25% 20% 15% 10% 5% H 0% Q4 Dynamics ■ OpEx +41% YoY vs. net revenue growth of 84% ■ OpEx % of revenue of 18.5% -563bps YoY 2020 Dynamics OpEx of $457M OpEx % of revenue of 18.3% -483bps YoY In Q2 2020 we recorded $7.3M in special items that benefitted Retail operating expense. Reported Retail operating expense in Q2 2020 was $125M, or 16.3% of revenue. 13#14Retail Adjusted EBITDA Adj. EBITDA ($M) $60 $50 $40 $30 $20 $10 $- $(10) $(20) $(2.5) (0.7%) Q1 '19 $1.6 0.4% Q2 '19 $(0.6) (0.2%) Q3 '19 $(2.2) $(1.9) loverstock. See Reconciliation in Appendix (0.6%) Q4 '19 (0.5%) Q1 '20 Retail Adjusted EBITDA is a non-GAAP financial measure. $53.0 6.9% Q2 '20 $50.2 7.0% Q3 '20 Adj. EBITDA Margin (%) $34.2 5.1% Q4 '20 8% 6% 4% 2% 0% (2%) Q4 Dynamics ■ ■ ■ Adj. EBITDA of $34M +$36M YOY 2020 Dynamics ■ Adj. EBITDA margin of 5.1% +572bps YoY Adj. EBITDA of $136M +$139M YOY Adj. EBITDA margin of 5.4% +569bps YoY 14#15overstock. Business Updates 15#16overstock. Oloverstock. Retail TM 16#17Top 5 Brand in a Growing Market Top U.S. Home Furnishings Online Brands ¹ (ranked by online revenue) Amazon 1. 2. Wayfair 3. Walmart 4. Target 5. overstock. 6. Pottery Barn 7. IKEA 8. Bed Bath & Beyond. 9. West Elm 10. Restoration Hardware Overstock growth was 2.3x the U.S. Home Furnishings eCommerce market in Q4 Overstock +75% YoY Home eCommerce² +32% YoY overstock. 50% 40% 30% 20% 10% 0% 6% 2010 Furniture & Home Furnishings U.S. Online Penetration ³ 7% 2011 8% 2012 9% 2013 11% 2014 13% 2015 16% 2016 1 Source: Public and third-party analyses and transactional data based on commonly accepted 'home furnishings and décor' category definitions. 2 Source: Estimate based on MasterCard Spending Pulse and Rakuten Intelligence, Q4 2020. 3 Source: Combined data from eMarketer, NRF, NPD, and Earnest transactional data. 18% 2017 20% 2018 23% 2019 35% Dec 2020 (est.) 17#18Why Overstock Is Outperforming + overstock. +7.5% Purchase intent among U.S. home furnishings shoppers. Yo Y +20% Yo Y Purchase intent among "Savvy Shoppers" Top Improved Brand Drivers: ▪ "Makes me feel like a smart shopper" ■ "Best quality for the price" ▪ "Free shipping" Source: Overstock Annual Brand Research, 2020. Note: purchase intent refers to customers who include Overstock in their purchase consideration set. 18#19Establishing Unique Market Positioning Home Goods Expertise. Dream Homes for All: The space of 'Smart Value' where quality & style costs less Value overstock. IKEA overstock Amazon Walmart 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 19#20Playing to Our Strengths overstock. Savvy Shoppers overstock. Reluctant Refreshers $120B Market1,2 Higher propensity to shop at Overstock ▪ Deal-driven and low-hassle ▪ Combined market spend is 40% of total market² 1 Source: eMarketer-Total U.S. Retail Sales estimates, 2019. 2 Source: Overstock customer segmentation research, 2019. Note: $300B total market size x 40% customer segments market size = $120B market. 20#21Focused Strategy dream homes for all vision financial goal target customers brand pillars enablers 2021 initiatives overstock. making beautiful & comfortable homes accessible by helping customers easily & confidently find just what they want for less sustainable, profitable market share growth primary segment savvy shopper values Overstock for helping them feel smart about finding a great deal from a compelling selection of stylish & quality home products product findability get inspired anywhere, but easily find it at Overstock OKR-driven focus smart value world-class SEO quality & style for less secondary segment reluctant refresher values Overstock for helping them easily & confidently find just what they want easy delivery + support data-driven customer relationship and loyalty building machine learning and algorithms innovation improve product findability grow government market share grow Canada market share improve enterprise platform fast, free, & predictable delivery, plus low-hassle returns & support rapid iteration mindset 21#22product findability ▪ Customers shifting to mobile In Q4, mobile: Purchases ~50% of total sales Unique visits +84% YoY Sales +100% YoY Conversion +8% YoY overstock. 80% 60% 40% 20% 0% H 80% 60% 40% 20% 0% H Q1'19 Q1'19 Q2'19 Q2'19 Q3'19 Sales % by Device Q3'19 Q4'19 Q1'20 Orders Delivered % by Device Q4'19 Q2'20 Q1'20 Mobile Desktop Mobile Desktop Q2'20 Q3'20 Q3'20 Q4'20 Q4'20 Note: Sales reflects GMS (gross merchandise sales), calculated as the amount paid by customers for products (and shipping), measured at the time of order, before coupons and discounts, without reductions for estimated returns. 22#23product findability ▪ Demand for home furnishings continues to increase H Home furnishings sales remained above. 90% in Q4 Highest home furnishings Q4 mix in history Opportunity to increase brand association with "Home" 2X higher purchase intent if shopper comes to OSTK for "Home" Emphasizing Dream Homes for All overstock. Q1 Sales Mix of Home Furnishings Q2 Q3 Q4 90% 83% 82% 80% 77% 73% Note: Sales Mix is shown as a percentage of gross merchandise volume, calculated as the amount paid by customers for products (and shipping), measured at the time of order, after coupons and discounts, without reductions for estimated returns. 2020 2019 -2018 2017 2016 2015 23#24smart value ■ Free shipping is a top purchase driver and key component of Smart Value Launched free shipping on all items in 2020 - Initially in response to COVID Permanently in late 2020 Significant win for our customers - overstock. Q4 '19 Source: Bizrate point of sale survey. Favorability relative to home and garden competitors. Customer Rating of Shipping Charges Q1 '20 Q2 '20 Q3 '20 11% favorable to competitors Q4 '20 24#25smart value ■ ■ Savvy Shoppers expect value Want to feel like they are getting "best quality for the price" Progress evident in continued refinement of pricing model ■ Pricing is another key component of Smart Value 55% overstock. Price comparisons taken during last week of respective month reported. Dec '19 Competitively Priced SKUs. 70% Jul '20 80% Dec '20 Note: Overstock prices used to compare to competitor prices include site sale discounts before coupons are applied. Comparisons account for 30-35% of all product page views. 25#26easy delivery + support ■ ■ 'Shipageddon' was less impactful due to rigorous carrier planning in Q4 Delivery speed and on-time accuracy key drivers of customer satisfaction overstock. 1/5/20 2/5/20 3/5/20 % Orders Delivered On-Time or Early Note: % orders delivered on-time or early refers to small parcels only. + + + 4/5/20 5/5/20 6/5/20 7/5/20 8/5/20 9/5/20 10/5/20 11/5/20 12/5/20 Click to Delivery (business days) H + + 1/12/20 2/12/20 3/12/20 4/12/20 5/12/20 6/12/20 7/12/20 8/12/20 9/12/20 10/12/20 11/12/20 12/12/20 26#27easy delivery + support ■ Contact volume as a percentage of orders decreased 23% YoY ■ Automation and self-service enhancements improve customer satisfaction and reduce costs Continued focus on automated delivery communications overstock. II Q4 '19 CS Contacts as % of Orders Q4 '19 Q1 '20 23% decrease 3.0x increase Q1 '20 Q2 '20 Self Service Cases as % of Total Q3 '20 Q2 '20 HI Q3 '20 Q4 '20 Note: Following the national stay-at-home order (Q2 '20), not all customers were able to reach customer service agents due to unexpected volume of sales. Q4 '20 27#282021 Strategic Initiatives 1 Improve onsite search and taxonomy 2 Expand into Canada 3 4 overstock. Establish government business Improve the enterprise platform 28#29Well Positioned for Market Share Growth in 2021 and Beyond. Revenue growth outpacing industry Driven by technology, customer focus, and drop-ship model ▪ Maintain normalized gross profit margins 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 29#30overstock. Overstock & Pelion Venture Partners Transaction 30#31Summary of Deal Terms overstock. Deal Type General Partner Limited Partner Partnership Term Capital Commitment Fee Structure Anticipated Closing 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 3-6 months, pending regulatory approvals Maximize shareholder value through partnering with a highly experienced venture firm. 31#32Overview of Pelion Venture Partners overstock. PELION VENTURE PARTNERS Experienced Investors Over 90 years of combined investment experience, currently on Fund VII Proven Tech Investing Strategy Expertise in and focus on early-stage tech investing: Seed and Series A+ Skilled Operators Experienced operators with deep knowledge and networks that enable growth Please note that this information does not constitute a solicitation for investment. Trusted Advisors Reputation of being trusted and active board members Fundraising Track Record Utah and SoCal local advantage with strong network in the Bay and coast-to-coast reach Culture of Innovation Investing in new technologies that disrupt industries 32#33overstock. Summary and Q&A#342020 Year in Review ▪ Notable changes to the executive team (Chief Financial/Product/Tech Officers) Appointments to the board (3 independent directors) Execution of focused, strategic Retail initiatives GSA proof-of-concept pilot award Opportunistic equity capital raise (~$200M) Strategic partnership with Pelion Venture Partners Record sales and profitability ■ overstock. 34#35Questions? To ask questions: Dial-in: (877) 673-5346 Conference ID: 9437865 Email: [email protected] overstock.#36overstock. Appendix#37Adjusted EBITDA Reconciliation. overstock. Net loss Depreciation and amortization Stock-based compensation Interest income, net Other (income) expense, net Provision (benefit) for income taxes Special items (see table below) Adjusted EBITDA Segment Adjusted EBITDA Retail tZERO MVI Other Adjusted EBITDA Special items: Special legal charges¹ Severance Impairments on intangible assets Total Special items Dec-2019 (29,660) 7,998 4,606 (262) (1,547) (94) (18,959) $ (2,194) (10,628) (2,695) (3,442) (18,959) Mar-2020 $ Three months ended Jun-2020 (19,565) 7,569 3,268 (72) (6,683) 176 (1,103) (16,410) (1,865) (8,250) (2,498) (3,797) (16,410) (2,501) 1,398 $ $ 34,381 7,548 2,465 (26) 4,171 517 (7,272) 41,784 53,011 (7,052) (2,085) (2,090) 41,784 (7,272) (1,103) $ (7,272) Sep-2020 21,226 7,592 2,623 177 7,526 620 288 $ 40,052 $ 50,249 (5,675) (2,470) (2,052) 40,052 288 288 Dec-2020 $ 10,129 8,107 4,574 159 (186) (324) 433 22,892 $ $ 34,247 (5,800) (2,653) (2,902) 22,892 433 433 1 Special legal charges include amounts associated with the resolution for and adjustments to various legal contingencies and legal fees associated with pursuing our strategic alternatives. 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. 37