#1Oloverstock.com Q3 2016 Financial Results 799 SV#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 June 30, 2016 which was filed with the Securities and Exchange Commission on August 4, 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. loverstock.com® 2#3Q3 2016 Results - OSTK Total Revenue $441.6 Million (13% increase vs. Q3 2015) Contribution Dollars* $49.2 Million (12% increase vs. Q3 2015) Pre-Tax Income (Loss)*** ($3.9 Million) ($0.9M) - Retail ($3.0M) - Medici (vs. ($2.6) million in Q3 2015) Gross Profit Dollars $79.7 Million (10% increase vs. Q3 2015) overstock.com Contribution Margin* 11.1% (vs. 11.2% in Q3 2015) Net Income (Loss)** ($3.1 Million) (vs. ($2.1) million in Q3 2015) Gross Margin 18.1% (vs. 18.5% in Q3 2015) Tech and G&A Expense*** $50.1 Million (9% increase vs. Q3 2015) TTM Operating Cash Flow $75.5 Million (vs. $44.9 million in Q3 2015) * Non-GAAP ** Net Income (loss) refers to Net income (loss) attributable to stockholders of Overstock.com, Inc. *** Q3 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. 3#4Q3 2016 Results - Retail Only (Direct and Partner) * Non-GAAP Revenue $437.6 Million (12% increase vs. Q3 2015) Contribution Dollars* $47.9 Million (9% increase vs. Q3 2015) overstock.com Gross Profit Dollars $78.4 Million (8% increase vs. Q3 2015) Contribution Margin* 11.0% (vs. 11.3% in Q3 2015) Gross Margin 17.9% (vs. 18.5% in Q3 2015) Pre-Tax Loss of ($0.9M) including $3.9M of impairment related charges (vs. pre-tax income of $0.8M in Q3 2015) 4#5Quarterly Revenue and Growth ($,000) 500,000 450,000 400,000 350,000 300,000 250,000 200,000 150,000 100,000 50,000 352,991 17% Q3-14 loverstock.com® Q4-14 Q1-15 Q2-15 Revenue ($) 391,211 11% Q3-15 Q4-15 Q1-16 Revenue growth (yoy) Q2-16 441,564 13% Q3-16 40% 35% 30% 25% 20% 15% 10% 5% 0% 81 5#6Quarterly Gross Profit and Growth ($,000) 90,000 80,000 70,000 60,000 50,000 40,000 30,000 20,000 10,000 0 (10,000) 67,058 13% Q3-14 loverstock.com® Q4-14 Q1-15 Q2-15 Gross profit ($) 72,451 8% Q3-15 III!! 10% Q4-15 Q1-16 Gross profit growth (yoy) 79,716 Q2-16 Q3-16 45% 40% 35% 30% 25% 20% 15% 10% 5% 0% -5% 6#7Quarterly Contribution and Growth* ($,000) 60,000 50,000 40,000 30,000 20,000 10,000 0 (10,000) 42,086 14% Q3-14 loverstock.com HANI Ul 12% 4% Q4-14 Q1-15 Contribution ($) Q2-15 43,926 Q3-15 Q1-16 Contribution growth (yoy) Q4-15 Non-GAAP: Contribution dollars = Gross profit less Sales & Marketing expense plus Club O Rewards and Gift Card breakage. 49,171 Q2-16 Q3-16 60% 50% 40% 30% 20% 10% 0% -10% 7#8Quarterly Gross Margin and Contribution Margin* 20.0% 18.0% 16.0% 14.0% 12.0% 10.0% 8.0% 6.0% 4.0% 2.0% 0.0% 19.0% 11.9% Q3-14 Q4-14 overstock.com® Q1-15 Q2-15 Gross margin 18.5% 11.2% Q3-15 Q4-15 Contribution margin Q1-16 Q2-16 * Non-GAAP: Contribution margin = Gross profit less Sales & Marketing expense plus Club O Rewards and Gift Card breakage as a percentage of revenue. 18.1% 11.1% Q3-16 8#9Technology and G&A Expenses $s and % of Revenue ($,000) 70,000 60,000 50,000 40,000 30,000 20,000 10,000 11.1% 39,275 6.3% 4.8% Q3-14 $4.6M overstock.com Q4-14 Q1-15 G&A G&A and Tech (% of revenue) Q2-15 11.7% 45,760 6.4% 5.3% Q3-15 Legal Case Judgments G&A (% of revenue) Q4-15 Q1-16 Q2-16 11.3% 50,056 6.1% 5.3% Q3-16 Technology -Technology (% of revenue) 12.0% 10.0% 8.0% 6.0% 4.0% 2.0% 0.0% 9#10Corporate Employees 1,400 1,200 1,000 800 600 400 200 1,011 III Q3-14 Q4-14 overstock.com® Q1-15 Q2-15 Corporate employees excludes customer service and warehouse staff. 1,087 Q3-15 Q4-15 Q1-16 Q2-16 1,152 Q3-16 10#11Operating and Free Cash Flow* (TTM) ($,000) 90,000 80,000 70,000 60,000 50,000 40,000 30,000 20,000 10,000 (10,000) (20,000) 69,365 32,724 12,788 Q3-14 Q4-14 overstock.com Q1-15 Q2-15 44,930 * Non-GAAP: Free Cash Flow = Cash Flow from Operations less Expenditures for Fixed Assets. 28,346 (7,253) Q3-15 Q4-15 Q1-16 Q2-16 Cash flow from operations (TTM) Free cash flow* (TTM) Cash paid for new headquarters construction (TTM) 75,477 49,999 (37) Q3-16 11#12GAAP TTM Inventory Turns and GMROI 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0.0 44.9 1027% Q3-14 Q4-14 overstock.com Q1-15 Q2-15 TTM Inventory turns TTM Inventory Turns = TTM COGS / Average Inventory. TTM GMROI = TTM Gross Margin % * TTM Revenue / Average Inventory 52.1 1192% Q3-15 Q4-15 Q1-16 TTM GMROI Q2-16 68.9 1516% Q3-16 2000% 1800% 1600% 1400% 1200% 1000% 800% 600% 400% 200% 0% 12#13Unique Customers and Cost Per Customer (#,000) 3,000 2,500 2,000 1,500 1,000 500 1,679 $15.15 Q3-14 loverstock.com® Q4-14 Unique customers Q1-15 Q2-15 1,766 $17.02 Q4-15 Q1-16 Marketing $ / unique customers (cost per customer) Q3-15 Q2-16 1,886 $18.40 Q3-16 $40.00 $35.00 $30.00 $25.00 $20.00 $15.00 $10.00 $5.00 13#14Customer Orders and Average Order Size* (#,000) 4,000 3,500 3,000 2,500 2,000 1,500 1,000 500 2,259 $180 Q3-14 Q4-14 loverstock.com Q1-15 Customer orders Q2-15 2,465 $183 Q3-15 Average Order Size is measured at the time of order, before promotional discounts and shipping revenue. Q4-15 Q1-16 Average order size* Q2-16 2,703 $192 Q3-16 $400 $350 $300 $250 $200 $150 $100 $50 $0 14#15Medici - Emerging Structure. 1 1 I I T 1 1 1 I 1 SPEEDROUTE R4 to tO TECHNOLOGIES PRO SECURITIES to's vision is to increase transparency, reduce settlement time, operational and frictional costs and counterparty risk in securities trading by using distributed ledger technology. OSTK Ownership: 81% loverstock.com® DATA IFX 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 IdentityMind's mission is to construct electronic identities and infuse integrity back into the global market of digital commerce. Investment: $1.2M Ownership: 5.0% 15#16Medici - The March Toward History • October 2014 - Announcement of Medici ● June 2015 - Cryptobond I • August 2015 - Cryptobond II • October 2015 - Announcement of Acquisition of t0.com ● December 2015 - S-3 Declared Effective March 2016 - Computershare as Transfer Agent • April 2016 - Georgeson as Information Agent ● • September 2016 - Keystone as Broker-Dealer October 2016 - ETC as Custodian ● ● ● Now - First Ever Public Blockchain Equity Offering November 10 - Record Date November 15 - Subscription Period Begins - December 6 - Subscription Period Ends loverstock.com 16#17loverstock.com Email all questions to: [email protected] f Follow Us On You Tube 8+ 17