#1Oloverstock. Q2 2018 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 significant increases in our marketing expenditures in the first half of 2018 and our subsequent reduction of those expenditures, the results of our ongoing review of strategic initiatives including the possible sale of our e-commerce business, adverse tax, regulatory or legal developments, competition, and any inability to raise capital or borrow funds on acceptable terms. Other risks and uncertainties include, among others, the risks of the businesses Medici Ventures and tZERO are pursuing, including whether tZERO's joint venture with Box Digital Markets, LLC will be able to achieve its objectives, the effects of key business personnel moving from our retail business to our Medici Ventures, Inc. and tZERO businesses, 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-K for the year ended December 31, 2017, our Form 10-Q for the quarter ended March 31, 2018, and our Form 10-Q for the quarter ended June 30, 2018, which were filed with the Securities and Exchange Commission on March 15, 2018, May 8, 2018, and August 9, 2018, respectively, and in our subsequent filings with the Securities and Exchange Commission. The Form 10-K, 10-Q's, 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. 2#3Agenda 1. tZERO 2. Other Medici Ventures 3. Retail 4. Q&A overstock. Val 0#4to tZERO overstock. STO & Strategic Investors STO Closed August 6, 2018 Executed SAFES: $174M ● ● STO: Raised $134M in Aggregate Consideration Term Sheet Agreements with GSR Capital (Hong Kong) $270M at $1.5B Post-money Valuation for tZERO $104.5M (3.1M Shares of OSTK @ $33.72) STO aggregate consideration includes $30 million repayment of intercompany debt between tZERO and Overstock. GSR has signed a repurchase agreement to acquire these tokens.#5tØ tZERO overstock. Market Opportunity: At a 'Tipping Point' in Shift to STOS ● ● The $5.3T global private issuance market is at a tipping point and we expect security tokens to grow at a compound rate of 215% over the next three years. Growth estimates on token issuances have accelerated significantly in 2018. Projected Market Cap of Security Tokens* ....... 2018 2019 2020 $180,000 $160,000 $140,000 $120,000 $100,000 $80,000 $60,000 $40,000 $20,000 2017 *Includes ICOs that should have been security tokens. Sources: CoinMarketCap, coinmarkets.net, icowatchlist.com, company estimates 2021 2022 LO 5#6to tZERO overstock. Market Opportunity: The Migration from Public Markets to Private Offerings Will Benefit Institutions and HNWI 141 IPOS 2652 Private Offerings Billions Raised (by Method) Global, excluding China, 2014 2675 Bonds 3630 Loans Source: Capital Raising in the U.S.: An Analysis of the Market for Unregistered Securities Offerings, 2009-2014, Scott Bauguess, Rachita Gullapalli, and Valadmir Ivanov 9098 Total Data provided as a reference only. 6#7to tZERO overstock. Our Goal Our goal is to leverage our regulatory and technological first mover advantages to be the leading global platform for tokenized assets. 7#8to tZERO overstock. Regulatory Advantage Other jurisdictions looking at US regulations for guidance Our established relationship with US regulators gives us credibility Our regulated exchanges will allow Asian and European brokers to trade in our listed securities November 2014 o tZERO Acquires Interest in Pro Securities April 2015 O ATS Deemed Effective December 2015 OSTK S-3 Went Effective December 2016 Regulated Trading Live on ATS December 2017 C tZERO STO January 2018 StockCross Acquisition June 2018 o BOX Joint Venture 8#9to tZERO overstock. Next Regulatory Step tZERO and BOX presenting updated rulebook for listing Security Tokens to SEC 9#10te tZERO overstock. Acquisition/Partnership Advantage 1. PRO Securities ATS 2. SpeedRoute 3. StockCross 4. BOX Digital JV 10#11to tZERO overstock. tZERO-BOX Digital JV Advantages of Exchange over ATS Setting Listing Standards National Exchange Can Draw Premium Issuers and Institutional Investors Publish Market Data Limited Exchange Licenses 1. 2. 3. 4. 5. Speed to Market 6. Boston Options Exchange Credibility Regulatory Expertise Alternative: 2+ Years, $25M-$75M Expense 11#12to tZERO overstock. Technological Advantage 1. Expertise in Mobile and UX 2. Dream Team (Blockchain + Enterprise Dev) Agile/Lean Software Development 4. Resource Pool from OSTK 12#13to tZERO overstock. Human Capital Saum Built a Dream Team 13#14to tZERO overstock. tZERO Platforms Issuer 1 c Issuer 2 Issuer 3 c 1 Investor 1 Issuer (STO) Platform 2 4 Investor 2 Broker Dealer Platform ↑↓ Crypto Smart Order Router / Exchange 3 Investor 3 Security Token Exchange 14#15to tZERO overstock. Product Roadmap Issuance Security Token Exchange ‒‒‒‒‒‒‒ ‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒ tZERO Token Issuance Broker Dealer Issue Additional Security Tokens Crypto Smart Order Router / Exchange - Reg S Trading of tZERO Token ‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒I Q3 2018 ‒‒‒‒‒‒‒‒‒‒‒‒‒ tZERO Token Trading Platform Support for All Traditional US Equities Additional Security Tokens Listed and Trading ‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒---- - Q4 2018 ----‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒‒ Reg D Trading of tZERO Token (tZERO-BOX JV) Onboarding Additional Clearing Firms Onboarding Additional BD's Smart Order Routing Crypto Exchange ‒‒‒‒‒‒‒‒‒‒‒ Trading Crypto Through tZERO Q1 2019 Q2 2019 15 ----‒‒‒‒‒‒‒‒. II ‒‒‒‒‒‒‒‒‒‒‒‒‒‒I#16|A MEDICI VENTURES D overstock. 16#17Medici Ventures Has Ownership Interests in Startup Companies Pursuing Blockchain Applications bitsy overstock. to tZERO FinClusive SettleMint MEDICI LAND GOVERNANCE spera bitt Voatz PEERNOVA FACTOM™ symbiont ripio NETKI IdentityMind GLOBAL 17#18Bitsy Wallet September Beta Easy to Use • Hold the Keys to Your Currency ● Unique Recovery Process Superior Wallet Due to Unique Architecture overstock. 9:41 bitsy Your assets Ł Home Buy your first Bitcoin. $10, $20, or $500. You're the boss. Bitcoin $1.234 Ethereum $1.234 Litecoin $1.234 Home Wallet Current price (USD) ? Help $1.234 > $1.234 > $1.234 > ✪ Settings 9:41 Graphics shown for illustrative purposes. Price for Bitcoin Payment method Total Bitcoin purchased! Wallet fee Network fee Bitcoin Return Current price (USD) $1.234 $1,234.00/BTC VISA 4111****1111 $0.55 $0.55 $1234.00 Backup Wallet 18#19● ● ● ● MEDICI LAND GOVERNANCE Building digital registration systems using blockchain and other technologies (mobile applications, social media, Al) Goal is to promote economic development and full financial inclusion of individuals Current projects: 1. World Bank: partnership to implement technology in several countries 2. Zambia: MOU with Ministry of Lands to create 50,000 digital titles in 2018 Pursuing projects in Rwanda, Ukraine, India, and Senegal Hernando de Soto overstock. 19#20overstock. Oloverstock. Retail DD M#21Retail Update 1. SEO 2. Course Correction: Minimize Dilution 3. Sales Tax Nexus: New Opportunities 4. Strategic Alternatives overstock. DD M#22SEO Jan-17 Feb-17 Mar-17 Apr-17 May-17 Jun-17 overstock. Jul-17 Google Organic Visits Aug-17 Sep-17 Oct-17 Nov-17 Dec-17 Jan-18 Feb-18 Mar-18 Apr-18 ||| May-18 Jun-18 Jul-18 22#23SEO Google Organic Visits vs. Forecast Without Ranking Drop Jan-17 Feb-17 Mar-17 Apr-17 May-17 Jun-17 Jul-17 Aug-17 Sep-17 Oct-17 Nov-17 Dec-17 Jan-18 Feb-18 Mar-18 overstock. Apr-18 May-18 Jun-18 Jul-18 23#24SEO Keyword Rankings in Top 100 Results Clarity Dashboard (v4.10) Create, edit, and view custom reports. Learn More Competitive Landsc... Competitive Rank > Day: 01/01/17 - 08/08/18 Top 100 Legacy Aug 2017 Google Mobile Keyword Count Imm Jan 01 -www.overstock.com overstock. Feb 21 Apr 13 Source: seoClarity (August 2018) Jun 03 Jul 24 Sep 13 Nov 03 Loun Dec 24 Feb 13 Apr 05 May 26 Options Jul 16 III wwwww 24#25SEO We Believe We Have Arrested the Slide Competitive Rank > Week: 01/01/18 - 01/07/18- 07/30/18 - 08/05/18 Top 100 Legacy Aug 2017 Google Mobile Keyword Count Wk Ended on 01/07 Wk Ended on 02/04 www.overstock.com overstock. Source: seoClarity (August 2018) Wk Ended on 03/04 Wk Ended on 04/01 Wk Ended on 04/29 Wk Ended on 05/27 Wk Ended on 06/24 Wk Ended on 07/22 ||||| 25#26Quarterly Revenue and GMV Growth 15% 10% 5% 0% -5% -10% -15% 3.3% 3.2% overstock. Q2 '17 -1.5% -4.0% Q3 '17 25.1 pts. -8.5%. -13.3% Q4 '17 Revenue Growth 5.8% 3.0% Q1 '18 ... GMV Growth 13.4% 11.8% Q2 '18 Course Correction Q3 '18 Q4 '18 GMV = 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. 26#27Quarterly Average Order Size $250 $200 $150 $100 $50 $0 overstock. $177 $189 ||||| Q2 '16 Q2 '14 $185 $196 Q2 '15 +7% Q2 '17 $210 Q2 '18 Average Order Size is measured at the time of order, before promotional discounts and shipping revenue. 27#28Sales Tax Nexus: New Opportunities 1. Offer Home Services (Design, Branded Delivery, & Repair) 2. Expand Affiliate & Influencer Networks 3. New Optimization Models for Advertising Spend 4. Improve & Expand Third Party Partnership Programs 5. Enhance Customer Rewards & Promotions 6. Access New Talent in More Regions 7. Increase Visibility through Sponsor Events 8. Open Pop-up Shops 9. Partner with Brick & Mortar for Pick-ups/Returns overstock. 28#29Strategic Alternatives ● ● Capitalize up from Medici (e.g. tZERO) Recapitalize with Large Capital Partner Who is Willing to Think Big Sell the Retail Business overstock. 29#30Securities Lawsuit Plaintiffs Drop Securities Class Action Lawsuit Against Overstock.com overstock. 30#31Send questions to [email protected] Ooverstock. ●#32overstock. Appendix#33Q2 2018 Results: OSTK Total Revenue $483.1 Million 12% increase vs. Q2 2017 Pre-Tax Loss ($65.9) Million ($57.4M) - Retail* ($8.6M) - Medici* vs. ($9.7) million in Q2 2017 ($6.4M) - Retail* ($3.3M) - Medici* overstock. Gross Profit $91.7 Million 9% increase vs. Q2 2017 TTM Operating Cash Flow ($59.5) Million vs. $20.3 million TTM 2017 * Gross Margin 19.0% vs. 19.5% in Q2 2017 Ending Cash $152.2 Million vs. $203.2 million at Dec. 31, 2017 Excluding intercompany transactions eliminated in consolidation 33