#124 1 overstock.com Q2 2017 799#2Safe Harbor The information presented herein may contain forward-looking statements. Such forward-looking statements include all statements other than statements of historical fact, including forecasts of trends. These forward-looking statements are inherently difficult to predict. Actual results could differ materially for a variety of reasons, including the amount and timing of our capital expenditures, the mix of products we sell, adverse tax, regulatory or legal developments, consumer or regulatory claims regarding the products we offer or sell, the extent to which we owe taxes or are required to collect sales or similar taxes in jurisdictions in which we do not do so, competition, fluctuations in our operating results, the potential effects on our financial results of new accounting standards we will be required to adopt no later than January 1, 2018, relating to revenue recognition, Google and other search engine companies changing their natural search engine algorithms periodically resulting in lower ranking of our products, any inability to raise capital or borrow funds on acceptable terms, difficulties we may have with our efforts to expand both domestically and internationally, and risks of inventory management and seasonality. Other risks and uncertainties include, among others, risks related to the business our subsidiary Medici Ventures, Inc. is pursuing, our continually evolving business model, and 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. More information about factors that could potentially affect our financial results is included in our Form 10-Q for the quarter ended June 30, 2017 which was filed with the Securities and Exchange Commission on August 3, 2017. The Form 10-Q and our subsequent filings with the Securities and Exchange Commission 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.com 2#3Q2 2017 Results - OSTK Total Revenue overstock.com $432.0 Million (3% increase vs. Q2 2016) Contribution Dollars* $41.4 Million (12% decrease vs. Q2 2016) Pre-Tax Income (Loss) ($9.7) Million ($6.4M) - Retail** ($3.3M) - Medici** (vs. ($1.5) million in Q2 2016) $1.4M Retail** ($2.9M) - Medici** * Non-GAAP - see discussion and reconciliation in our earnings press release ** Excluding intercompany transactions eliminated in consolidation *** Net Income refers to Net income attributable to stockholders of Overstock.com, Inc. Gross Profit Dollars $84.2 Million (10% increase vs. Q2 2016) Contribution Margin* 9.6% (vs. 11.2% in Q2 2016) Net Income (Loss)* ($7.5) Million (vs. ($904,000) in Q2 2016) *** Gross Margin 19.5% (vs. 18.2% in Q2 2016) Tech and G&A Expense $50.6 Million (4% increase vs. Q2 2016) TTM Operating Cash Flow $20.1 Million (vs. $75.4 million in Q2 2016) 3#4Q2 2017 Results - Retail Only (Direct and Partner) Revenue overstock.com $428.0 Million (3% increase vs. Q2 2016) Contribution Dollars* $40.4 Million (12% decrease vs. Q2 2016) * Non-GAAP - see discussion and reconciliation in our earnings press release Gross Profit Dollars $82.9 Million (10% increase vs. Q2 2016) Contribution Margin* 9.4% (vs. 11.0% in Q2 2016) Gross Margin 19.4% (vs. 18.1% in Q2 2016) Pre-Tax Income (Loss) ($6.4M) (vs. $1.4M in Q2 2016) 4#5What has really gone on in the Retail business •Google / SEO Email Migration Marketing Tech Migration •Wayfair overstock.com LO 5#6Wayfair Comparison - Visits and Ad Spend Total Visits (in millions) 500 450 400 350 300 250 200 150 100 50 $58 $26 Q1 15 $62 Ad Spend data source: Overstock and Wayfair 10-Ks and 10-Qs Visit data source: Hitwise, a division of Connexity overstock.com $26 Visits and Ad Spend Q2 15 $71 $28 $88 Q3 15 $36 Q4 15 $98 Wayfair Total Visits (M) -Wayfair Ad Spend ($M) $94 $29 FEETFI Q1 16 $30 $101 $32 Q2 16 $116 $44 Q3 16 Overstock Total Visits (M) Overstock Ad Spend ($M) Q4 16 $118 $34 Q1 17 $140 $120 $100 $80 $60 $40 $20 $- Ad Spend (in millions) 6#7Wayfair Comparison - Days Payable Outstanding (DPO) 50.0 45.0 40.0 35.0 30.0 25.0 20.0 15.0 10.0 5.0 35.5 21.3 Q1-15 TTM Avg. Accounts Payable divided by TTM Cost of Goods Sold/360 Source: Overstock and Wayfair 10-Ks and 10-Qs overstock.com 36.2 21.4 Q2-15 37.9 21.0 Q3-15 38.7 21.5 Q4-15 -Overstock DPO 39.7 22.1 Q1-16 40.4 22.3 Q2-16 -Wayfair DPO 41.4 22.9 Q3-16 42.3 21.4 Q4-16 43.6 21.7 Q1-17 7#8Wayfair Comparison - Accounts Payable % of Cash 140% 120% 100% 80% 60% 40% 20% 0% 54% 44% Q1-15 65% 52% Q2-15 80% Overstock - Accounts Payable divided by Cash & Cash Equivalents Wayfair - Accounts Payable divided by Cash & Cash Equivalents plus Short Term Investments Source: Overstock and Wayfair 10-Ks and 10-Qs overstock.com 59% Q3-15 72% 70% Q4-15 -Overstock Accounts Payable % of Cash 81% 62% Q1-16 88% 64% Q2-16 107% 68% Q3-16 109% 58% Q4-16 -Wayfair Accounts Payable % of Cash 131% 63% Q1-17 8#9CARS by Overstock.com OCARS by overstock™ overstock.com CORS Research Buy 3.1M Cars Profect 學 ally Finance CAROLICO See what's near you 9#10Why Overstock Cars: Aided Purchase Consideration overstock.com For the following companies, how likely would you be to consider purchasing a car through an online marketplace they created? Overstock.com 5% Amazon.com 9% Google.com 5% eBay.com 6% Source: OSTK Voice of the Consumer Panel - Mark Howard Walmart 4% 10% Extremely Likely 16% 13% 26% 22% 15% Somewhat Likely 23% 26% 18% 27% 26% Neither Likely nor unlikely 21% 17% Somewhat Unlikely 17% 17% 53% 35% 38% Extremely Unlikely 26% 27% 10#11Why Overstock Cars? Customers: BEST Research (Motortrend) • ~4M Cars Available • Better Faceted Search Anonymous Negotiations (currently 40% of dealers) • Lowest Cost for Warranties Financing All Financial Situations - totally online Off Lease Vehicles (in process) • Parts And Maintenance To The Home (Q4) • Cars Can Be Viewed in Virtual Reality ● ● ● ● overstock.com Sellers: - FREE to use FREE traffic, more exposure of inventory 11#12Why Cars by Overstock.com? Revenue Opportunities Around The Entire Ownership Experience Financing, Warranty, Insurance (Q4), Parts (Q4) • Ad Revenue • Attract more Male/Millennial consumers First to Market Entire Ownership Experience Research, Buy, Repair/Maintain, Sell Potential Cross Monetization on Partner Sites ● ● overstock.com 12#13Protection Plan Importance Used car overstock.com New car How important is the Vehicle Protection Plan to your selection of a new or used car? Source: OSTK Voice of the Consumer Panel - Mark Howard Extremely Important 38% 38% I Very Important Moderately Important 23% 23% Slightly Important 24% 21% Not at all Important 6% 7% 9% 10% 13#14Financing & Warranty Bank Rates ➜ 1.99% - 17.99% -Tops out at 23% If Credit Score is Under 500 Excellent Credit -ACH Transfer to Bank Account Good Credit and Lower - Funds Sent To Dealer Finance Providers Warranty Provider: Ally (formerly GMAC) Pays 99.3% of Claims overstock.com 14#15Status Launching in Beta getting Customer Feedback • Live with Research, Finance, Buy, Warranty, and Refinance App With Virtual Reality (coming soon) Getting Off-Lease Vehicles Exploring Strategic Partnerships overstock.com 15#16Blockchain Securities Lending to T ZERO 16#17Dr. Alan Greenspan, October 23, 2008 ALAN GREENSPAN Former Chairman Federal Reserve Board, 1987-2006 Thursday C-SPAN There are additional regulatory changes that this breakdown of the central pillar of competitive markets requires in order to return to stability, particularly in the areas of fraud, settlement and securitization. 17#18Eg Pension Fund III Prime Broker Securities Lending: How It Is Supposed to Work C $20. ↑A Short seller 18#19Eg Pension Fund III Prime Broker Securities Lending: Over-locating 个圆 Short seller $20 $20 Short seller $20- Short seller 19#20Pension Fund [$6 Eg $14 Prime Broker Securities Lending: B.O.Gets 30% Rebate C $20. 與 Short seller 20#21Pension Fund 60¢ Eg $1.40. Prime Broker Securities Lending: Opacity C $2. Prime Broker $20 Short seller 21#22Dr. Alan Greenspan, October 23, 2008 ALAN GREENSPAN Former Chairman Federal Reserve Board, 1987-2006 Thursday C-SPAN There are additional regulatory changes that this breakdown of the central pillar of competitive markets requires in order to return to stability, particularly in the areas of fraud, settlement and securitization. 22#23Eg Pension Fund III Prime Broker t0: Digital Locate Receipts 山 $8 $2 (DLR) •$10. 店 Short seller 23#24For further information visit: tZero.com/dlr or t0.com/dlr 24#25overstock.com Email all questions to: [email protected] Follow Us On f Ⓡ You Tube g+ 25