#1Ooverstock.com Q3 2017 Earnings Call#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, 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 September 30, 2017 which was filed with the Securities and Exchange Commission on November 8, 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. Ooverstock.com#3GAAP Operating Margin 4.0% 2.0% 0.0% -2.0% -4.0% -6.0% -8.0% -10.0% -12.0% 2009 Ooverstock.com 2010 2011 2012 Overstock Wayfair 2013 Amazon 2014 2015 2016 Operating Income (Loss) divided by Revenue Source: OSTK, Wayfair, and Amazon 10-Ks Overstock figures are Retail only (excluding Medici) Amazon figures exclude AWS (results without AWS not available prior to 2013) 3#4in millions $25,000 $2,500 $2,000 $1,500 $1,000 $500 Amazon overstock.com® Groupon Wayfair Capital Raised Houzz Jet Etsy Zulily Buy.com Gilt One Kings Lane Overstock Estimated Capital Raised (includes IPO proceeds, other offerings, and latest outstanding long term debt, less treasury stock, where info available) Source: Crunchbase.com and Company 10-Qs and 10-Ks 4#5GAAP Operating Margin 4.0% 2.0% 0.0% -2.0% -4.0% -6.0% -8.0% -10.0% -12.0% 2009 2010 Overstock overstock.com 2011 2013 2014 2015 Amazon 2012 -Wayfair 2016 Capital Raised in millions $25,000 $2,500 $2,000 $1,500 $1,000 $500 Amazon Groupon Wayfair Houzz Jet Etsy Zulily Buy.com Gilt One Kings Lane Overstock 5#6Technology Recognition COL COL COL COL COMPUWARE APPLICATION PER PER PER PER PERFORMANCE AWARDS Best OF THE Web Best of Web Performance Winner WMA WEB MARKETING ASSOCIATION Best Shopping App for iOS & Android overstock.com Overstock.com Best Small Business Website 5x BMA SILVER AWARD Best Designed Mobile App WIRED In-house Recommendation Engine overstock. Fast, interactive pages with AMP ● 8% increase in conversion 36% increase in revenue T content that d collapse ser their early Featured by Google at the ing great 2017 Chrome Dev Summit X From overstock.com ces & Punitet Aman 1154M-5166M ALLAN MOOVANK Fidem Q1 6#7McKinsey survey on website user experience Website is easy to use 90 80 70 60 50 40 30 20 10 0 66 Overall overstock.com 80 Amazon 72 Overstock.com 65 64 Walmart Bed Bath and Beyond 62 62 Target Kohls 58 57 Wayfair Lowes 53 Sears 48 45 Hayneedle Home Depot McKinsey&Company 7#8Award-winning Customer Care LOYALTY 360 The association for customer loyalty #1 in Operational Excellence in Customer Care NRF 5-years of Top Customer Care HFN HOME FURNISHINGS NEW S HFN's Top 100 Retailers overstock.com TM CUSTOMER J.D.POWER AND ASSOCIATES SINCE #2 Customer Satisfaction 1968 Ÿ VENTANA RESEARCH Operational Leadership Award Gartner # 1 Customer Service Optimization Forbes 2014 AMERICA'S MOST TRUSTWORTHY COMPANIES STELLA SERVICE Best Overall Customer Service Experience THE AMERICAN BUSINESS AWARDS Customer Care Department of the Year 200 8#9Annual revenue per developer/data scientist $ 5.0M overstock.com 2015 $ 6.1M ■Wayfair Overstock $ 3.4M 2016 $ 7.1M Efficiency Ratio = (Annual Revenue / End of Year Head Count of Developers & Data Scientists) Source: Overstock and Wayfair 10-Ks and Investor Presentations 9#10GAAP Operating Margin 4.0% 2.0% 0.0% -2.0% -4.0% -6.0% -8.0% -10.0% -12.0% 2009 2010 Overstock overstock.com 2011 2013 2014 2015 Amazon 2012 -Wayfair 2016 Capital Raised in millions $25,000 $2,500 $2,000 $1,500 $1,000 $500 Amazon Groupon Wayfair Houzz Jet Etsy Zulily Buy.com Gilt One Kings Lane Overstock 10#11overstock.com Building a Tech Stack for Civilization overstock.com VENTURES A MEDICI 11#12overstock.com Commerce Identity & Voting Capital Markets Capital Money 12#13overstock.com Commerce Identity & Voting Capital Markets Capital Money 13#14Blockchain meets money bitt overstock.com ● ● ● Digital fiat currency for central banks Digital wallets Commerce Identity & Voting Capital Markets Capital Money Near-frictionless payments (including remittances) Financial inclusion ("Banking the unbanked") Medici ownership: 11% with options to 34.8% Earliest possible soft launch: December 2017 14#15Blockchain meets money ripio spera PEERNOVA overstock.com • Digital wallet, payments, and credit lending 100K+ active users in Latin America Medici ownership: 2.25% ● SME payments and invoicing systems • Medici ownership: 18% ● ● ● Banking compliance and data immutability Medici ownership: 12% Commerce Identity & Voting Capital Markets Capital Money 15#16overstock.com Commerce Identity & Voting Capital Markets Capital Money 16#17Blockchain meets capital formation factom overstock.com Mortgage loan compliance Digital asset verification Medici ownership: 2.5% ? Commerce Identity & Voting Capital Markets Capital Money 17#18overstock.com Commerce Identity & Voting Capital Markets Capital Money 18#19Blockchain meets capital markets to t ZERO symbiont overstock.com ● ● ● ● ● ● ● ● Instant trade clearance and settlement SEC-compliant Exchange for ICOS Securities Lending: Digital Locate Receipts Medici ownership: 81% Smart contracts for digital securities Digitized corporate ownership records Private equity syndication and crowdfunding Medici ownership: 1% Commerce Identity & Voting Capital Markets Capital Money 19#20Marc Cohodes and Me overstock.com = ►YouTube VIDEO || Search 1:14/7:35 GRANT'S X SLIDES Former enemy turned friend Patrick Byrne Ovenstock.com (Nasdaq OSTK) Marc Cohodes likes OSTK cause 'ITS GOING WAY THE FUQ UP' +1 CC 0 9+ 20#21● DIGITAL LOCATE RECEIPT PLATFORM VENUE FOR TRADING ICO'S overstock.com 21#22J.W. HARBIDGE, CSR JANUARY 25, 2011 JAMES DENGLER EXHIBIT NO. 12 Goldman Sachs overstock.com [U.S. Securities Lending] CONFIDENTIAL January 2009 1 GSE T 01231056 22#23[ CONFIDENTIAL overstock.com U.S. Securities Lending revenues contributed 75% of Americas Prime Brokerage revenues, 70% of Global Securities Lendi revenue and 51% of Global Prime Brokerage revenues 3 GSE T 01231058 REDACTED 23#24SECURITIES LENDING: HOW IT IS SUPPOSED TO WORK Eg PENSION FUND III PRIME BROKER overstock.com See full animation in the earnings call replay on http://investors.overstock.com/ C $20- DJ SHORT SELLE 24#25SECURITIES LENDING: OVER-LOCATING PENSION FUND III Eg |overstock.com PRIME BROKER See full animation in the earnings call replay on http://investors.overstock.com/ 介面 SHORT SELLER $20. $20. SHORT SELLER [$20- 介面 SHORT SELLE 25#26Dr. 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. 26#27NY Teamsters Pension Becomes First To Run Out Of Money As Expert Warns "Pension Tsunami" Is Coming Pensions&Investments Pension funds sue 6 investment banks over securities lending market collusion COURTS BY RICK BAERT AUGUST 17, 2017 12:30 PM UPDATED 3:32 PM 27#28tZERO: Digital Locate Receipts Eg Pension Fund III Prime Broker to $8 $2 DLR See full animation in the earnings call replay on http://investors.overstock.com/ $10 Short seller 28#29tZERO: Digital Locate Receipts Supply Side (last 5 days) 2,000 Traders (Today) $80B - $120B of lendable One dozen brokers currently securities in the process of rollout overstock.com For further information, visit: tZero.com/dlr or tØ.com/dlr 29#30● DIGITAL LOCATE RECEIPT PLATFORM VENUE FOR TRADING ICO'S overstock.com 30#31EXCHANGE MCMXXXIV COMMISSION Investor.gov U.S. SECURITIES AND EXCHANGE COMMISSION THE PROBLEM About Us INVESTOR BULLETIN: INITIAL COIN OFFERINGS 1 07/25/2017 Developers, businesses, and individuals increasingly are using initial coin offerings, also called ICOS sales, to raise capital. These activities may provide fair and lawful investment opportunities. Howe technologies and financial products, such as those associated with ICOS, can be used improperly to investors with the promise of high returns in a new investment space. The SEC's Office of Investor E and Advocacy is issuing this Investor Bulletin to make investors aware of potential risks of particip "Virtual coins or tokens that are offered or sold may be securities..." - Investor Bulletin, July 25, 2017 overstock.com "...any entity or person engaging in the activities of an exchange must register as a national securities exchange or operate pursuant to an exemption from such registration." - DAO Report, July 25, 2017 Source: https://www.investor.gov/additional-resources/news-alerts/alerts-bulletins/investor-bulletin-initial-coin-offerings 31#32● An approved venue (ATS) That can trade blockchain instruments • And is SEC Compliant. ● THE SOLUTION: overstock.com to ICO VENUE 32#33Types of Instrument "Fiat" currency Cryptocurrency Utility token Security token Ooverstock.com Taxonomy of Money Example Dollars, Yen, Euro Bitcoin, Ethereum Civic, Status DAO, tZERO Description "Money" created by fiat of a government Digital asset using cryptography Units of services that can be purchased. Can trade on our ATS (or image of it) Tradeable on tZERO ATS 33#34overstock.com Commerce Identity & Voting Capital Markets Capital Money 34#35Blockchain meets identity and voting 00000000 IdentityMind 000 5000 SettleMint overstock.com TM GLOBAL ● ● Digital identity and compliance Risk management automation Medici ownership: 5% • Secure and auditable voting • Document authentication • Just launched ICO for loT ● Medici ownership: 33% ● Commerce Identity & Voting Capital Markets Capital Money 35#36to bitt tZERO A MEDICI VENTURES overstock.com SettleMint PEERNOVA IdentityMind GLOBAL ripio factom symbiont S spera 36#37overstock.com Commerce Identity & Voting Capital Markets Capital Money 37#38Overstock.com Commerce overstock.com Commerce Identity & Voting Capital Markets Capital Money 38#39Q3 2017 Results: Overstock Total Revenue $424.0 Million (4% decrease vs. Q3 2016) Contribution Dollars* $39.2 Million (20% decrease vs. Q3 2016) Pre-Tax Income (Loss) ($6.5) Million ($2.9M) - Retail** ($3.7M) - Medici** (vs. ($3.9) million in Q3 2016) ($0.9M) - Retail** ($3.0M) - Medici** overstock.com Gross Profit Dollars $83.7 Million (5% increase vs. Q3 2016) Contribution Margin* 9.2% (vs. 11.1% in Q3 2016) Net Income (Loss)*** ($786,000) $1.1M - Retail** ($1.9M) - Medici** (vs. ($3.1) million in Q3 2016) ($1.7M) - Retail** ($1.4M) - Medici** Gross Margin 19.7% (vs. 18.1% in Q3 2016) Tech and G&A Expense $50.4 Million (1% increase vs. Q3 2016) TTM Operating Cash Flow ($7.7) Million (vs. $75.5 million in Q3 2016) * 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. 39#40Q3 2017 Results: Retail Only Revenue $420.1 Million (4% decrease vs. Q3 2016) Contribution Dollars* $38.1 Million (20% decrease vs. Q3 2016) overstock.com Gross Profit Dollars $82.4 Million (5% increase vs. Q3 2016) Contribution Margin* 9.1% (vs. 11.0% in Q3 2016) * Gross Margin 19.6% (vs. 17.9% in Q3 2016) Pre-Tax Income (Loss) ($2.9M) (vs. ($942,000) in Q3 2016) Non-GAAP - see discussion and reconciliation in our earnings press release 40#41Clubo Paid memberships up 30% YoY New paid signups Jan-17 Feb-17 Mar-17 overstock.com Apr-17 May-17 Jun-17 Jul-17 Aug-17 Sep-17 1 Oct-17 Club O will be even more rewarding for members in 2018 41#42New Email System Doubled Email Growth Rate in Q3 Email Order Growth Rate Q2 Ooverstock.com Q3 Automated campaigns at all time highs in daily orders New system allows for faster campaign development, tuning, and improvement Personalization improvements expected to yield significant email gains 42#4332% YoY Order Growth for Other Large Channels: Affiliates, Paid Keywords, PLA, Facebook, & Pinterest overstock.com 31.6% Q3 2017 43#44SEO Rankings vs. Customer Experience 7000 0009 5000 4000 3000 2000 1000 0 Google Organic Rankings Benchmark: April 1, 2017-September 30, 2017 4/1/17 4/8/17 4/15/17 4/22/17 4/29/17 5/6/17 5/13/17 5/20/17 5/27/17 www.overstock.com 6/3/17 6/10/17 6/17/17 6/24/17 7/1/17 7/8/17 7/15/17 www.amazon.com 7/22/17 7/29/17 8/5/17 8/12/17 8/19/17 www.walmart.com Source: Top three rankings based on 20k top tracked keywords, SEO Clarity, 2017 overstock.com® 8/26/17 www.target.com 9/2/17 9/9/17 9/16/17 9/23/17 9/30/17 Overall Satisfaction (1-10 scale) 9.25 9.20 9.15 9.10 9.05 9.00 8.95 8.90 8.85 8.80 December 2016 January 2017 Customer Experience Satisfaction Overstock February 2017 March 2017 April 2017 May 2017 June 2017 July 2017 Home Furnishing eCommerce Competitors Source: Bizrate Insights, Point of Sale Experience Survey, OSTK vs. 17 key Home Furnishing competitors August 2017 44 September 2017#452016 Wayfair Comparison Customer Acquisition Cost $70 $60 $50 $40 $30 $20 $10 $0 $38 overstock.com $68 Overstock ■Wayfair Implied New Customers (1) Customer Acquisition Cost (2) Overstock has significant growth potential at much lower acquisition costs. Overstock Wayfair 3,570 6,040 $38 $68 (1) Calculated as (1-% of orders from Repeat Customers) * Total Orders (2) Calculated as Total Advertising Spend divided by Implied New Customers Source: Overstock and Wayfair 10-Ks and Investor Presentations 45#46Likely Marketing Outcomes 1. Absent SEO improvement, profitable growth returns in May. 2. Mother of all site experience updates in December/January. 3. ClubO is meaningful (>25% of sales) and (finally) soaring. 4. New Marketing Paradigm Project New paid ClubO signups overstock.com Jan-17 Feb-17 Mar-17 Apr-17 May-17 Jun-17 Jul-17 Aug-17 Sep-17 Oct-17 46#47Overstock.com Cars by overstock™ CARFAX Autotrader 4 TRUECar cars.com edmunds CarGurus Ooverstock.com Average Monthly Visits 32.1K 14.4M 26.7M 9.8M 21.1M 24M 52.2M Total Vehicles 1.4M* 2M 4.2M 874k Used Unknown New 4.7M Unknown Unknown Research X Reviews X New Cars for Sale X Used Cars for Sale Online Financing X > XXX X Vehicle VSP's (Warranties) History × × X X X × X X × × Used Vehicle Values X X Cars by Overstock average monthly visits from Google AdWords. Competitor monthly visits from SimilarWeb. Feature comparison list compiled 10/26/2017. *3M-4M cars will be listed by Q1 of 2018 47#48GAAP Operating Margin 3.0% -2.0% -7.0% -12.0% n 2009 2010 2011 2012 2013 2014 2015 2016 Overstock -Wayfair Amazon ● $25,000 Ooverstock.com $2,500 $2,000 $1,500 Tu $1,000 $500 Amazon Groupon Wayfair Houzz Capital Raised Jet Etsy STRATEGIC OPTIONS UNDER CONSIDERATION 1. Solve someone else's problem Brick-and-mortar: technology, logistics, return logistics, marketing, site speed, etc. Other high-traffic websites 2. Recapitalize with large capital partner who is willing to think big 3. Capitalize up from Medici (e.g., tØ) Zulily We have engaged Guggenheim Partners (Andy Taussig) Buy.com Gilt One Kings Lane Overstock 48#49send questions to [email protected] overstock.com