#1311 Ooverstock.com Investor Education Session November 2016 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, the results of legal proceedings and claims and the amounts we spend relating to them, the extent to which we owe income taxes, competition, fluctuations in operating results, any inability to raise capital if needed on acceptable terms, our efforts to expand both domestically and internationally, risks of inventory management and seasonality. Other risks and uncertainties include, among others, risks related to new products and services we may offer, and difficulties 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, 2016 which was filed with the Securities and Exchange Commission on November 3, 2016. These and our other subsequent filings with the Securities and Exchange Commission identify important factors that could cause our actual results to differ materially from those contained in our projections, estimates and other forward-looking statements. Overstock.com, Inc. has filed a registration statement (including a prospectus) and a prospectus supplement with the SEC for the offering to which this communication relates. Before you invest, you should read the prospectus in that registration statement and the prospectus supplement Overstock.com, Inc. has filed with the SEC for the securities offered pursuant to the registration statement, and other documents that Overstock.com, Inc. has filed or files in the future with the SEC for more complete information about Overstock.com, Inc. and the offering. You may get these documents for free by visiting EDGAR on the SEC Web site at www.sec.gov. Alternatively, Overstock.com, Inc. will arrange to send you the prospectus if you request it by calling 1-801-947-5409. Ooverstock.com#3Ooverstock.com Retail Business 3#4IPACE Ⓒi INFORMATION Ooverstock.com PRICE ASSORTMENT CONVENIENCE A ★ ENTERTAINMENT#5Assortment, Price & Convenience Assortment SKU Count (excludes BMMG) 6,000,000 5,000,000 4,000,000 3,000,000 2,000,000 1,000,000 Price Ooverstock.com 197,206 2010 251,008 2011 343,593 2012 491,382 2013 683,149 2014 876,611 2015 1,791,890 5,000,000 Current 2017 target Convenience 5#6Wayfair Comparison - Ad Spend / Visit $1.00 $0.90 $0.80 $0.70 $0.60 $0.50 $0.40 $0.30 $0.20 $0.10 $0.00 $0.94 $0.34 Q4 14 $0.88 $0.28 Q1 15 Ad Spend / Visit Note: Ad Spend data source: Overstock and Wayfair 10-Q's; Visit data source: Hitwise overstock.com $0.88 $0.29 Q2 15 $0.84 $0.32 Q3 15 Wayfair Ad Spend/Visit $0.83 $0.32 Q4 15 $0.90 $0.29 Q1 16 Overstock Ad Spend/Visit $0.90 $0.32 Q2 16 $0.84 $0.32 Q3 16 6#7Wayfair Comparison - Daily Market Share Daily Market Share (by visits) 0.6% 0.5% 0.4% 0.3% 0.2% Note: Visit data source: Hitwise wwww overstock.com 12 26 19 Sep Sep Sep 2016 min www.overstock.com www.wayfair.com Daily market share in Shopping and Classifieds, measured by visits, based on US usage. Created: 11/29/2016. © Copyright 1998-2016 Hitwise Pty. Ltd. 03 10 17 24 31 Oct Oct Oct Oct Oct 07 Nov 0.54% Source: Hitwise 0.51% 14 21 28 Nov Nov Nov 2016 7#8Ooverstock.com Blockchain / FinTech 8#9Medici - Emerging Structure SPEEDROUTE R4 to tO TECHNOLOGIES PRO SECURITIES to's platform integrates cryptographically secure distributed ledgers with existing market processes to reduce settlement time and costs, increase transparency, efficiency, and availability for multiple asset classes. OSTK Ownership: 81% DATA IFX Ooverstock.com 1 1 1 1 1 1 T MEDICI VENTURES INC PEER NOVA PeerNova builds immutable systems for large scale commercial applications. Investment: $5M Ownership: 7.5% BITT The Bitt wallet provides a quick, secure and easy way to manage your funds; giving you freedom to do more with your money. Investment: $4M Ownership: 11.4% IDENTITY MIND Identity Mind's mission is to construct electronic identities and infuse integrity back into the global market of digital commerce. Investment: $1.2M Ownership: 5.0% SETTLEMINT Settle Mint seeks to develop blockchain solutions for voting and land titling. Investment: €0.3M Ownership: 30% 9#10to - The March Towards the First Public Blockchain Equity Offering October 2014 - Announcement of Medici • June 2015 - Cryptobond I August 2015 - Cryptobond II • August 2015 - Announcement of SpeedRoute Acquisitions December 2015 S-3 Declared Effective March 2016 Computershare as Transfer Agent for Digital Securities • April 2016 - Georgeson as Information Agent • September 2016 - Keystone as Broker-Dealer October 2016 - ETC as Custodian - - - November/December 2016 - First Public Blockchain Equity Offering November 10 Record Date November 15- Subscription Period Begins December 6 Subscription Period Ends Ooverstock.com 10#11Ooverstock.com Rights Offering 11#12Blockchain Voting Series A Preferred Will trade only on PRO Securities ATS utilizing the t0 platform Investor must open online brokerage account with Keystone - To open a Keystone account, go to https://kccbd.to.com All access to Series A is through a Keystone account Digital "wallets" are created in connection with opening a Keystone account Wallet addresses and entire trading history will be public through to website Same day settlement of trades Restrictions on ownership: - Only U.S. residents meeting the requirements - Shares may be held only in the name of beneficial owner - No "street name" or other nominee accounts Substantially similar to our common stock - Plus a preferential right to an annual dividend of 1.0% of the subscription price Ooverstock.com 12#13Blockchain Voting Series A Preferred (cont.) OSTK may redeem the Series A for three years OSTK may convert Series A into Series B at any time • No minimum subscription Trading may be limited ● ● To exercise subscription rights, see https://www.mydigitalshares.com ● • For help with subscription process, copies of documents and any questions Information Agent: Georgeson at 866-432-2791 or Overstock@ Georgeson.com Read Prospectus Supplement before investing Ooverstock.com 13#14Voting Series B Preferred Traditional (non-digital) shares otherwise identical to the Series A OSTK may redeem the Series B for three years Expected to trade in the OTC market and be quoted on OTCQB ● ● ● ● Not subject to the restrictions on ownership that apply to the Series A No minimum subscription Trading may be limited For help with subscription process, copies of documents and any questions - Information Agent: Georgeson at 866-432-2791 or Overstock@ Georgeson.com Read Prospectus Supplement before investing Ooverstock.com 14#15Secondary Market for Series A Preferred If you do not hold Overstock common shares, but would like to participate in the secondary market for Series A preferred shares, you must open a Keystone brokerage account at https://kccbd.to.com. Secondary trading begins December 16 Ooverstock.com 15#16Ooverstock.com General Corporate Information 16#17Q3 and YTD 2016 Highlights 2016 Highlights revenue growth gross profit growth gross margin operating income pre-tax income ostk retail medici net income Q3 2016 overstock.com 13% 10% 18.1% 18.3% $7.3M $16.7M $25.9M ($9.2M) $9.4M operating cash flow (TTM) $75.5M Q3 and YTD 2016 results include pre-tax charges of $3.9M related to impairment of an international minority investment we hold and bad debt expense for accounts receivable owed to us from this entity. YTD 2016 ($5.0M) ($3.9M) ($0.9M) ($3.0M) ($3.1M) 8% 5% 17#18Quarterly Revenue and Growth ($,000) 500,000 450,000 400,000 350,000 300,000 250,000 200,000 150,000 100,000 50,000 0 352,991 17% Q3-14 Ooverstock.com 391,211 Halil 11% Q4-14 Q1-15 Q2-15 Revenue ($) Q3-15 Q4-15 Q1-16 Revenue growth (yoy) 41,564 Q2-16 13% Q3-16 40% 35% 30% 25% 20% 15% 10% 5% 0% 18#19Operating and Free Cash Flow* (TTM) ($,000) 90,000 80,000 70,000 60,000 50,000 40,000 30,000 20,000 10,000 0 (10,000) (20,000) 69,365 32,724 12,788 Q3-14 Q4-14 Q1-15 overstock.com Q2-15 44,930 28,346 (7,253) Q3-15 * Non-GAAP: Free Cash Flow = Cash Flow from Operations less Expenditures for Fixed Assets. Q4-15 Q1-16 ■Cash flow from operations (TTM) Free cash flow* (TTM) Cash paid for new headquarters construction (TTM) Q2-16 75,477 49,999 (37) Q3-16 19#20Senior Management Name / Position Dr. Patrick Byrne CEO Jonathan Johnson III President, Medici Saum Noursalehi President, Retail Robert Hughes SVP, Finance & Risk Management Vidya Jwala SVP, Demand Fulfillment JP Knab SVP, Demand Creation Carter Lee SVP, Technology Natalie Malaszenko SVP, Marketing Brian Popelka SVP, Customer & People Care Ooverstock.com Years with Overstock 17 14 11 8 0 10 15 1 14 Previous Experience Centricut, LLC; Fechheimer Brothers, Inc. TenFold Corp; Milbank, Tweed, Hadley & McCloy Utah Admin. Office of Courts; Brooks Automation TenFold Corp; Oracle; KPMG Walmart; Tractor Supply Co; Lowe's; Jo-Ann Stores USWF; 1-800 Contacts; Phonex Broadband Hospice of the Valley; Motherboard Discount Center Omni Hotels & Resorts; Hewlett Packard; Petco; Dell Citadel Communications; Disney Corp. 20#21Ooverstock.com Questions? 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