#1Ooverstock.com Q4 & FY 2017 Earnings Call tak TAT +#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-K for the year ended December 31, 2017 which was filed with the Securities and Exchange Commission on March 15, 2018. The Form 10-K 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#3overstock.com Strategic Options 3#420% 18% 16% 14% 12% 10% 8% 6% 4% 2% 0% Oct-16 Q4 2017 Branding (TV Spots) Nov-16 Wayfair ~ Dec-16 Jan-17 8:1 Feb-17 Overstock Mar-17 See later slides for source and notes. m Share of Choice % of US shoppers intending to purchase from (retailer) at next home goods purchase Apr-17 May-17 -Wayfair Jun-17 Jul-17 v Aug-17 Sep-17 50,000 -Overstock (50,000) (100,000) (150,000) (200,000) (250,000) (300,000) Oct-17 Nov-17 ■Wayfair Pre-Tax Income Dec-17 8,004 2009 Jan-18 Feb-18 14,248 2010 2011 25% 20% 15% 10% 5% 0% -5% -10% -15% -20% -25% (19,580) (21,005) Mar-17 15,154 2012 Apr-17 Overstock Retail Pre-Tax Income May-17 (15,480) 16,344 2013 Jun-17 10,092 (25,422) (off IF (77,348) (193,767) T Jul-17 13,205 (147,923) Monthly New Customer Growth 2014 Aug-17 2015 Sep-17 32,332 Oct-17 Nov-17 2016 Y Dec-17 (244,128) Jan-18 2017 Feb-18 +#5Tax Impact on 2017 Results in millions $120 $100 $80 $60 $40 $20 $0 Ooverstock.com $59 $25 $14 $12 2017 Net Loss Allowance on DTAS due to retail strategy (will be discussed later) Trump's Tax Cuts and Jobs Act (Federal rate reduction) Retail Medici Net Loss before tax changes 5#62017 Annual Results: OSTK Total Revenue $1.7 Billion (3% decrease vs. 2016) Contribution Dollars* $162.7 Million (19% decrease vs. 2016) Pre-Tax Income (Loss) ($47.7) Million ($25.4M) - Retail** ($22.3M) - Medici** (vs. $20.5 million in 2016) $32.3M Retail** ($11.8M) - Medici** overstock.com Gross Profit Dollars $340.6 Million (3% increase vs. 2016) Contribution Margin* 9.3% (vs. 11.1% in 2016) Net Income (Loss)**** ($109.9) Million ($91.6M) - Retail** ($18.3M) - Medici** (vs. $12.5 million in 2016) $18.5M Retail** ($6.0M) - Medici** Gross Margin 19.5% (vs. 18.4% in 2016) Tech and G&A Expense $206.6 Million (5% increase vs. 2016) TTM Operating Cash Flow ($35.3) Million (vs. $39.6 million in 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. Includes $84M of non-cash tax provision related to tax changes (discussed on prior slide) 6#7Overstock.com Retail overstock.com 7#8Ooverstock.com 8 2017-03-18 2017-03-25 2017-04-01 2017-04-08 2017-04-15 2017-04-22 2017-04-29 2017-05-06 2017-05-13 2017-05-20 2017-05-27 2017-06-03 2017-06-10 2017-06-17 2017-06-24 2017-07-01 2017-07-08 2017-07-15 2017-07-22 2017-07-29 2017-08-05 2017-08-12 2017-08-19 2017-08-26 2017-09-02 2017-09-09 2017-09-16 2017-09-23 2017-09-30 2017-10-07 2017-10-14 2017-10-21 2017-10-28 2017-11-04 2017-11-11 2017-11-18 2017-11-25 2017-12-02 2017-12-09 2017-12-16 2017-12-23 2017-12-30 2018-01-06 2018-01-13 2018-01-20 2018-01-27 2018-02-03 2018-02-10 2018-02-17 2018-02-24 2018-03-04 2018-03-11 -30.00% -20.00% -10.00% 0.00% 10.00% 20.00% 30.00% Weekly New Customer Growth#9Monthly New Customer Growth 25% 20% 15% 10% 5% 0% -5% -10% -15% -20% -25% Mar-17 Apr-17 Ooverstock.com May-17 Jun-17 Jul-17 Aug-17 Sep-17 Oct-17 " Nov-17 Dec-17 Jan-18 Feb-18 9#10Capital Raised in millions $25,000 $1,500 $1,250 $1,000 $750 $500 $250 Amazon overstock.com® Groupon Wayfair Houzz Jet Zulily Gilt Overstock Estimated Capital Raised (includes IPO proceeds, other offerings, and outstanding long term debt, less treasury stock, where info available) Source: Crunchbase.com and Company 10-Qs and 10-Ks (data through 9/30/2017 where available) 10#11GAAP Retail 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 repren T 2012 Wayfair Overstock 2013 Operating Income (Loss) divided by Revenue Source: OSTK, Wayfair, and Amazon 10-Ks Amazon 2014 2015 2016 2017 Overstock figures are Retail only (excluding Medici) Amazon figures exclude AWS (results without AWS not available prior to 2013) 11#12Quarterly Advertising Spend in millions $180 $160 $140 $120 $100 $80 $60 $40 $20 $- $98 $29 $94 $30 Ooverstock.com $101 $32 $116 $45 $118 $34 $124 $40 Source: Overstock and Wayfair 10-Ks and 10-Qs $142 $41 $166 Q1 2016 Q2 2016 Q3 2016 Q4 2016 Q1 2017 Q2 2017 Q3 2017 Q4 2017 Wayfair Overstock $50 Q4 2017 Branding (TV Spots) Wayfair 8:1 Source: Nielsen Ad Intel Overstock 12#13Lower Customer Acquisition Cost in 2017 $70 $60 $50 $40 $30 $20 $10 $0 overstock.com $73 Wayfair $50 Overstock Overstock continues to maintain significant CAC advantage even with deterioration in free organic traffic (discussed in Q3 earnings call). Source: Overstock and Wayfair 10Ks and investor presentations Customer acquisition cost calculated as Total Advertising Spend divided by Implied New Customers. Implied New Customers calculated as (1 - % of orders from Repeat Customers) * Total Orders 13#14Wayfair Comparison: Pre-tax Income (Loss) Wayfair Pre-Tax Income Overstock Retail Pre-Tax Income 50,000 0 (50,000) (100,000) (150,000) (200,000) (250,000) (300,000) 8,004 2009 overstock.com 14,248 2010 (19,580) 2011 15,154 (21,005) 2012 16,344 (15,480) 13,205 2013 10,092 (77,348) MI (147,923) (193,767) 2014 32,332 2015 2016 (25,422) (244,128) 2017 Source: Overstock and Wayfair 10-Ks and 10-Qs 14#15overstock.com® Source: Hitwise, a division of Connexity. 2018 US visit share of shopping websites. -Wayfair -Overstock 15 01/01/2018 01/02/2018 01/03/2018 01/04/2018 01/05/2018 01/06/2018 01/07/2018 01/08/2018 01/09/2018 01/10/2018 01/11/2018 01/12/2018 01/13/2018 01/14/2018 01/15/2018 01/16/2018 01/17/2018 01/18/2018 01/19/2018 01/20/2018 01/21/2018 01/22/2018 01/23/2018 01/24/2018 01/25/2018 01/26/2018 01/27/2018 01/28/2018 01/29/2018 01/30/2018 01/31/2018 02/01/2018 02/02/2018 02/03/2018 02/04/2018 02/05/2018 02/06/2018 02/07/2018 02/08/2018 02/09/2018 02/10/2018 02/11/2018 02/12/2018 02/13/2018 02/14/2018 02/15/2018 02/16/2018 02/17/2018 02/18/2018 02/19/2018 02/20/2018 02/21/2018 02/22/2018 02/23/2018 02/24/2018 02/25/2018 02/26/2018 02/27/2018 02/28/2018 03/01/2018 03/02/2018 03/03/2018 03/04/2018 03/05/2018 03/06/2018 03/07/2018 03/08/2018 03/09/2018 03/10/2018 03/11/2018 03/12/2018 03/13/2018 LA fff 0.90% Competitive Visit Share#16Competitive Customer Preference 20% 18% 16% 14% 12% 10% 8% 6% 4% 2% 0% Oct-16 Nov-16 m Dec-16 Share of Choice % of US shoppers intending to purchase from (retailer) at next home goods purchase Ooverstock.com Jan-17 Feb-17 mm Mar-17 Apr-17 May-17 Jun-17 -Wayfair Jul-17 Overstock M Aug-17 Sep-17 Oct-17 Nov-17 Source: Overstock Weekly Brand Tracker (administered through Qualtrics), 2017-2018. US sample of online shoppers. 3 week rolled averages of ~300 base size per period. Dec-17 Jan-18 Feb-18 16#17GAAP Retail Operating Margin 4.0% 2.0% 0.0% -2.0% -4.0% -6.0% -8.0% -10.0% -12.0% 2009 in millions $25,000 $1,500 $1,250 $1,000 $750 $500 $250 $- 2010 Capital Raised Amazon 2011 ■ Wayfair Groupon Ooverstock.com "T TT™ 2012 Wayfair 2013 ■Overstock Houzz 2014 Jet 2015 Amazon Zulily 2016 Gilt 2017 Overstock Quarterly Advertising Spend in millions $180 $160 $140 $120 $100 $80 $60 $40 $20 $- See prior slides for sources and notes. $98 $29 $94 $30 Q1 2016 Q2 2016 $101 $32 $116 Q3 2016 ■Wayfair $45 $118 $34 Q4 2016 Q1 2017 $124 $40 ■Overstock $142 $41 Q2 2017 Q3 2017 $166 $50 Q4 2017 17#18Competitive Strengths of the Retail Business Price Assortment Convenience Ooverstock.com Low Cost Leader in the Home • Club O Loyalty Program (25% of Revenue in Q4 2017) Financing Options ● ● ● ● ● ● Automated Supplier Platform (Automated Promos, Pricing, SKU Optimization) Expanding Private Label Rapid SKU and Partner Onboarding Site Infrastructure Optimized for Speed Proprietary Search & Personalization Platforms Augmented Reality 18#19Our Proprietary Technology is Recognized Across the Industry EEEE Best 0 0 0 0 OF THE Web COMP COMP COMP COMP COMPUWARE APPLICATION PER PER PER PER PERFORMANCE AWARDS Best of Web Performance Winner BMA overstock.com SILVER AWARD Best Designed Mobile App WMA WEB MARKETING ASSOCIATION Best Shopping App for iOS & The association for customer loyalty Award-winning Customer Care Fuels Customer Retention Android 6x 360 #1 in Operational Excellence in Customer Care #1 Customer Service Optimization VENTANA RESEARCH Operational Leadership Award Gartner HFN HOME FURNISHINGS NEWS HFN's Top 100 Retailers WIRED In-house Recommendation Engine NRF 6 Years of Top Customer Care THE AMERICAN BUSINESS AWARDS™ Customer Care Department of the Year MOBILE ST R AWARDS™ "Best of 2017" Best Shopping or Deals App CUSTOMER HIGHEST SATISFACTION J.D.POWER AND ASSOCIATESS #2 Customer Satisfaction ontent that collapse Featured by Google at the 2017 Chrome Dev Summit Goverstock Fast, interactive pages with AMP .8% increase in conversion .36% increase in revenue Best Overall Customer Service Experience Forbes 2014 AMERICA'S MOST TRUSTWORTHY COMPANIES STELLA SERVICE DENTRE 19#20Club O Memberships (Paid): Major Growth Driver club GOLD Total paid memberships through end of Q4 2017 loverstock.com Jan Feb Mar Apr May Jun Jul Aug Sep 2017 Oct Nov Dec +47% YoY 20#21Partner Onboarding SKU Creation • 6M SKUs (including product options) Suppliers: same-day account creation SKUS: on-site within minutes ● ● 460 2005 540 2006 overstock.com 730 2007 1,250 1,200 || 2008 2009 1,600 2010 2,000 Active Drop Ship Partners 2011 2,100 2012 2,400 2013 3,200 2014 Active Marketplace Partners 3,700 2015 4,100 259 2016 4,100 344 2017 21#22Recent SEO Performance Head Keywords in Top 3 Organic Positions In thousands 18 161412 108 10 6 420 5-Nov 12-Nov 19-Nov 26-Nov 3-Dec Overstock Source: SEO Clarity 10-Dec 17-Dec Ooverstock.com 24-Dec 31-Dec Amazon 7-Jan -Wayfair 14-Jan 28-Jan 21-Jan 4-Feb -Walmart 11-Feb 18-Feb -Target Indexed pages up from 5M to 22M YTD: Visits down 44%, Conversion up 38% Recovery outside of head keywords 25-Feb 4-Mar In millions 25 20 15 10 LO 5 O 5-Nov 0% -5% -10% -15% -20% -25% -30% -35% -40% -45% 12-Nov 19-Nov 5-Nov Source: Google Search Console 3-Dec 26-Nov 12-Nov 19-Nov 10-Dec 3-Dec 26-Nov Indexed Pages 17-Dec 10-Dec 24-Dec 31-Dec 17-Dec 7-Jan Google Organic Search Sales Growth 24-Dec 14-Jan 31-Dec 7-Jan 21-Jan 28-Jan 4-Feb 14-Jan 21-Jan 11-Feb 18-Feb 28-Jan O TIVER THE LEAD THEOD CAFOD BROD LA 4-Mar 11-Feb 25-Feb 22#23Innovations: FinanceHub overstock.com Overstock.com Overstock Cars™ Lending Student Loans Personal Loans Mortgage Loans Auto Loans FinanceHub By Overstock.com Investments Automated Investing Stock Trading More ▼ TM Overstock Pet Adoptions™ Welcome to FinanceHub Your central hub for loans, credit cards, insurance and more. We are here to help take the stress out of funding and securing your dreams. Get Matched with a Lender in Minutes What type of loan are you looking for? Select a loan type Personal Loans TM + What state do you live in? Utah Student Loans + How would you rate your credit Your Credit Health Connect to Partner Log in Mortgage Loans 23 +#24New for Club O Members $1.99 Stock Trades $2.99 for Non-Club O Members Oloverstock.com 24#25Innovations: Automated Investing ("Robo-Advising") overstock.com Overstock.com Overstock Cars™ FinanceHub By Overstock.com Lending Student Loans Personal Loans Mortgage Loans Auto Loans Investments Automated Investing Stock Trading TM Insurance Vehicle Home Business Overstock Pet Adoptions™ Credit Cards Overstock Store Credit Card Club O Rewards MasterCard No Credit Needed Leasing Automated Investing Overstock FinanceHubTM has partnered with tZERO Advisors to help you on your way to long-term financial success. As a leader in automated investing, tZERO Advisors provides access to sophisticated, equity- based investment services, at a low cost. Get Started 480 Log in Investing Basics Investing is a means for individuals to increase their wealth. Investing comes in all styles and flavors, and is as varied as the individuals who invest. It is basically placing your money in an investment vehicle (such as a stock, bond ETF or Mutual Fund, which we will discuss later), instead of letting it sit in a low returning, traditional bank savings account. 25#26Innovations: Cars overstock.com ill cars by Overstock Available in Salt Lake City, UT Search Cars Near You Find, finance, and know your auto All Makes Model Condition Find Zip Research Search Finance Protect Q Search Listings Near You → 26#27A MEDICI VENTURES overstock.com 27#28Medici Ventures Develops and Advances Blockchain Technology A blockchain is a cryptographically secured, distributed infrastructure, or network, which may be accessed and in some cases maintained by each member of the network. Medici Ventures has a team of ~30 software engineers, developers, and other technologists working on enterprise level software development and deployment. Medici Ventures purchases interests in blockchain-related companies and, as appropriate, follows up by strategically deploying its personnel within these companies. overstock.com 28#29Medici Ventures Has Five Areas of Interest Examples: Personal Identity IdentityMind GLOBAL overstock.com Money & Banking Capital Markets -0-0-0 $ bitt Property & Land FOR SALE DESOTO PROPERTY RIGHTS to tZERO Voting A B с Voatz 29#30Medici Ventures Has Ownership Interests in Startup Companies Pursuing Blockchain Applications overstock.com® to tZERO ripio DESOTO PROPERTY RIGHTS PEERNOVA symbiont IdentityMind bitt S spera SettleMint BITSY factom Voatz 30#31Blockchain Meets Personal Identity & Voting IdentityMind I Digital identity and compliance ▪ Risk management automation GLOBAL overstock.com SettleMint ■ Secure and auditable voting ▪ Document authentication ▪ ICO in process ✔Voatz ■ Platform for secure high-volume remote voting on smartphones and tables Approximately 70,000+ users over the past 18 months (1) (1) As of January 8, 2018; Source: https://www.prnewswire.com/news-releases/voatz-raises-22-million-seed-round-led-by-medici-ventures-300578763.html 31#32Blockchain Meets Property and Land: DeSoto, Inc. DESOTO PROPERTY RIGHTS overstock.com DeSoto intends to build systems using blockchain, social media, artificial intelligence, and mobile apps to help develop more effective records of ownership in developing countries 32#33Blockchain Meets Money bitt overstock.com ■ ■ Bitt, Inc., is a company based in Barbados that operates a digital asset exchange ▪ Bitt is working to develop a blockchain-based payment and banking solution to digitize fiat currencies (currencies declared legal tender by a governmental authority) in cooperation with one or more Caribbean central banks BITSY Bitsy is a startup company building a regulatorily-compliant bridge between the U.S. Dollar and cryptocurrency markets. ripio Digital wallet, payments, and credit lending ■ Bitsy may also offer Overstock customers a way to purchase cryptocurrencies on the Overstock site. 100K+ active users in Latin America (1) PEERNOVA Banking compliance and data immutability S spera SME payments and invoicing systems (1) Source: http://invezz.com/news/crypto/27804-Upcoming-ICO-Ripio-ICO-Makes-Inroads-in-Latin-American-Banking- Other companies in capital markets I Digitized corporate ownership records ▪ Private equity syndication and crowdfunding ■ symbiont Smart contracts for digital securities ■ factom Mortgage loan compliance Digital asset verification 33#34Blockchain Meets Capital Markets to tZERO overstock.com tZERO is Medici's largest blockchain commitment and an 80% owned subsidiary tZERO is a financial technology company focused on the development and commercialization of financial applications of blockchain technologies tZERO is currently involved in the following: Non-Blockchain tZERO owns two registered broker dealers - Speed Route and PRO Securities Speed Route is an electronic, agency-only, FINRA-registered broker dealer that provides connectivity for its customers to U.S. equity exchanges as well as off-exchange sources of liquidity such as dark pools. All of SpeedRoute's customers are registered broker dealers ■ ■ ■ ■ ■ The PRO Securities ATS operates an overnight trading sessions known as the Blue Ocean Division Recent and Planned Advisory Services tZERO recently purchased 65.8% of the membership units of a registered investment advisor firm, now known as tZERO Advisors ■ ■ ■ ■ PRO Securities is a FINRA-registered broker dealer that owns and operates the PRO Securities ATS, which is regulated by the SEC (1) An ATS is a trading system not regulated as an exchange, but is a licensed venue for matching buy and sell orders tZERO Advisors is offering automated investment advisory services through our website's FinanceHub tZERO recently purchased 81% of VerifyInvestor, LLC, a leading accreditation processing firm tZERO Advisors intends to offer advisory services to companies considering or pursuing security token offerings Blockchain Based Digital Locate Receipts tZERO has developed software - referred to as DLR software - intended to help broker dealer licensees with stock inventory to both load and manage inventory in order to assist short sellers of public securities I DLR software is currently in customer testing by StockCross and has not yet been commercially licensed to any broker dealers Security Token Trading System In 2016 tZERO developed a suite of trading software for use on the registered alternative trading system ("ATS") operated by its subsidiary PRO Securities ■ ■ In December 2016 Overstock completed the first public issuance of a Blockchain security traded under OSTKP, utilizing the PRO Securities ATS tZERO intends to leverage its experience to develop a new trading system (the "Token Trading System") that will be capable of trading tokens or coins issued by companies in security token offerings that are treated as securities for purposes of U.S. securities laws (1) As of the date of this presentation, tZERO is only in the preliminary stages of development of the Token Trading System. The Token Trading System may never be developed and, even if it is developed, may, for a variety of technological, legal and regulatory reasons, never become operational. 34#35tZERO Ecosystem Clients FIX US Exchanges OMSS (Bloomberg, etc.) ↓ Smart Order Routing / Al SpeedRoute overstock.com Risk Mgmt. ATSS / Dark Pools Front-end U.S. Equity Markets tZERO Affiliate SpeedRoute Technology & Software PRO ATS Blue Ocean 24/5 Trading FIX Protocol Security Token Trading Platform To be conducted within SEC regs. Issuance & "Listings" Crypto Exchanges GDAX Gemini Kraken Poloniex Binance Bittrex Bitfinex 35#36Blockchain Meets Capital Markets (Continued) to tZERO overstock.com Additional Interests Siebert Financial Transactions On January 31, 2018, tZERO purchased a 24% interest in StockCross Financial Services, Inc. ("StockCross"), an affiliate of Siebert Financial Corp. ("Siebert"), and approximately 1.2 million shares of Siebert, from 12 individuals for $12 million ■ ■ ■ In a separate transaction, also on January 31, 2018, tZERO purchased 70,000 additional shares of Siebert, and a one percent ownership interest in Kennedy Cabot Acquisition, LLC, the controlling owner of Siebert ("KCA”), from KCA for $1 million tZERO believes that StockCross, a self-clearing brokerage firm, will be an important part of a network of financial firms that tZERO intends to assemble FinanceHub contains a link to access electronic discount US equity trading through Muriel Siebert, a registered broker dealer WPS Prime Letter of Intent On February 6, 2018, tZERO entered into a Letter of Intent (the "WPS LOI") with Weeden Prime Services, LLC ("WPS"), a U.S. registered broker-dealer. The WPS LOI contemplates that tZERO will acquire 51% of the outstanding membership interests of WPS for $11.0 million in cash with a subsequent purchase, prior to the first anniversary of the initial purchase, of an additional 30% of the aggregate membership interests of WPS for an additional $7.0 million in cash. Following the subsequent purchase, tZERO will own 81% of the then-outstanding membership units of WPS. The WPS LOI contemplates that the existing members of WPS shall retain certain minority investor rights, including with respect to representation on the board of managers of WPS (proportionate to ownership) and customary drag-along and tag- along rights and anti-dilution protections. The WPS LOI also contemplates that any time following the first anniversary of the second closing, tZERO may, with 60-days' written notice, acquire all (but not less than all) of the outstanding membership units of WPS not then owned by tZERO at fair market value. tZERO expects the transaction to close during third quarter of 2018, subject to the execution of definitive documentation, any applicable regulatory approvals and customary closing conditions. Other tZERO is also considering additional equity purchases. 36#37Blockchain Meets Capital Markets (Continued) to tZERO overstock.com Security Token Offering On December 18, 2017, tZERO launched a $250 million(¹) offering (the "Security Token Offering" or "STO") of the right to acquire, if issued by tZERO in the future, tZERO Preferred Equity Tokens (the “tZERO Security Token") through a Simple Agreement for Future Equity ("SAFE") The STO is expected to run through May 14, 2018 but may be extended or shortened There can be no assurance that the STO will be successful or that any tZERO Security Token will ever be issued tZERO currently expects to use the net proceeds of the Security Token Offering to: (i) repay amounts payable to Overstock (ii) make further strategic equity purchases (iii) to make investments in the development of the tZERO Security Token and the development of the Token Trading System (iv) develop the functional utility features that tZERO may offer to holders of the tZERO Security Token (v) fund general corporate purposes, which may include capital expenditures, acquisitions, debt repayments, cybersecurity upgrades and short term investments, among other things, and (vi) perform regulatory lobbying activities regarding blockchain technology Overstock may purchase up to $30 million of Tokens in the STO or may elect to receive Tokens in payment of some or all of tZERO's indebtedness to Overstock ■ ■ ■ - - - ■ ■ However, Overstock has not yet made a determination, and there can be no assurance as to whether or not either or both such possibilities will occur As of March 14, 2018, tZERO has received $91.4 million in proceeds, net of withdrawals, from the STO.(²) - € tZERO may increate the amount of the STO to $300 million. This presentation is not an offering to sell, or a solicitation of an offer to buy, tZERO Security Tokens, which are only offered by means of tZERO's Amended, Supplemented and Restated Offering Memorandun, dated March 1, 2018, 37#38overstock.com RAVENCOIN 38#39Retail Strategy overstock.com 39#40overstock.com Strategic Options 40#41Growth Strategy • Grow investment in technology platforms (including Al/ML) ● • Selectively increase branding and digital marketing Add distribution facilities to speed shipping to customer Accelerate private label strategy Expand Club O rewards program to enhance customer loyalty ● ● overstock.com 41#42send questions to [email protected] overstock.com#4320% 18% 16% 14% 12% 10% 8% 6% 4% 2% 0% Oct-16 Q4 2017 Branding (TV Spots) Nov-16 Wayfair ~ Dec-16 Jan-17 8:1 Feb-17 Overstock Mar-17 See prior slides for source and notes. m Share of Choice % of US shoppers intending to purchase from (retailer) at next home goods purchase Apr-17 May-17 -Wayfair Jun-17 Jul-17 v Aug-17 Sep-17 50,000 -Overstock (50,000) (100,000) (150,000) (200,000) (250,000) (300,000) Oct-17 Nov-17 ■Wayfair Pre-Tax Income Dec-17 8,004 2009 Jan-18 Feb-18 14,248 2010 2011 25% 20% 15% 10% 5% 0% -5% -10% -15% -20% -25% (19,580) (21,005) Mar-17 15,154 2012 Apr-17 Overstock Retail Pre-Tax Income May-17 (15,480) 16,344 2013 Jun-17 10,092 (25,422) (off IF (77,348) (193,767) T Jul-17 13,205 (147,923) Monthly New Customer Growth 2014 Aug-17 2015 Sep-17 32,332 Oct-17 Nov-17 2016 Y Dec-17 (244,128) Jan-18 2017 Feb-18 43