#18% રામા overstock.com Q4 and Fiscal Year 2016 Financial Results R6#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. loverstock.com® 2#3Q4 2016 Results - OSTK Total Revenue $526.2 Million (10% increase vs. Q4 2015) Contribution Dollars* $54.2 Million (15% increase vs. Q4 2015) Pre-Tax Income (Loss) $3.9 Million $6.8M Retail** ($3.0M) - Medici** (vs. ($2.0) million in Q4 2015) $0.3M - Retail** ($2.3M) - Medici** Gross Profit Dollars $98.0 Million (18% increase vs. Q4 2015) overstock.com Contribution Margin* 10.3% (vs. 9.8% in Q4 2015) * Non-GAAP Excluding intercompany transactions eliminated in consolidation *** Net Income refers to Net income attributable to stockholders of Overstock.com, Inc. *** Net Income $3.1 Million (vs. $110,000 in Q4 2015) Gross Margin 18.6% (vs. 17.3% in Q4 2015) Tech and G&A Expense $50.0 Million (4% increase vs. Q4 2015) TTM Operating Cash Flow $39.6 Million (vs. $54.5 million in Q4 2015) 3#4Q4 2016 Results - Retail Only (Direct and Partner) * Non-GAAP Revenue $521.5 Million (9% increase vs. Q4 2015) Contribution Dollars* $53.1 Million (16% increase vs. Q4 2015) overstock.com Gross Profit Dollars $96.8 Million (19% increase vs. Q4 2015) Contribution Margin* 10.2% (vs. 9.6% in Q4 2015) Gross Margin 18.6% (vs. 17.1% in Q4 2015) Pre-Tax Income $6.8M (vs. pre-tax income of $0.3M in Q4 2015) 4#5Quarterly Revenue and Growth ($,000) 600,000 500,000 400,000 300,000 200,000 100,000 470,360 18% Q4-14 loverstock.com® Q1-15 Q2-15 Q3-15 Revenue ($) 480,270 Lill 10% 2% Q4-15 Q1-16 Q2-16 Revenue growth (yoy) 526,182 Q3-16 Q4-16 40% 35% 30% 25% 20% 15% 10% 5% 0% 81 5#6Quarterly Gross Profit and Growth ($,000) 110,000 100,000 90,000 80,000 70,000 60,000 50,000 40,000 30,000 20,000 10,000 0 (10,000) 85,380 19% Q4-14 |overstock.com Q1-15 Q2-15 Q3-15 Gross profit ($) 83,109 -3% Q4-15 Q1-16 Q2-16 Gross profit growth(yoy) Q3-16 98,004 18% Q4-16 45% 40% 35% 30% 25% 20% 15% 10% 5% 0% -5% 6#7Quarterly Contribution and Growth* ($,000) 60,000 50,000 40,000 30,000 20,000 10,000 0 (10,000) 49,290 21% Q4-14 Q1-15 loverstock.com Q2-15 Contribution ($) Q3-15 47,226 -4% Q4-15 Q2-16 Contribution growth (yoy) Q1-16 Non-GAAP: Contribution dollars = Gross profit less Sales & Marketing expense plus Club O Rewards and Gift Card breakage. Q3-16 54,185 15% Q4-16 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% 18.2% 10.5% Q4-14 Q1-15 overstock.com® Q2-15 Q3-15 Gross margin 17.3% 9.8% Q4-15 Q1-16 Contribution margin Q2-16 Q3-16 * Non-GAAP: Contribution margin = Gross profit less Sales & Marketing expense plus Club O Rewards and Gift Card breakage as a percentage of revenue. 18.6% 10.3% Q4-16 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 9.9% 46,575 5.0% 4.9% Q4-14 G&A overstock.com Q1-15 Technology Q2-15 Q3-15 10.0% 47,851 5.5% 4.5% Q4-15 G&A and Tech (% of revenue) Q1-16 Q2-16 G&A (% of revenue) Q3-16 9.5% 49,966 5.4% 4.1% Q4-16 -Technology (% of revenue) 12.0% 10.0% 8.0% 6.0% 4.0% 2.0% 0.0% 9#102016 Annual Results - OSTK Total Revenue $1.8 Billion (9% increase vs. 2015) Contribution Dollars* $200.3 Million (8% increase vs. 2015) Pre-Tax Income (Loss) $20.5 Million $32.3M-Retail** ($11.8M) - Medici** (vs. $3.1 million in 2015) $10.1M - Retail** ($7.0M) - Medici** Gross Profit Dollars $331.3 Million (9% increase vs. 2015) loverstock.com Contribution Margin* 11.1% (vs. 11.2% in 2015) * Non-GAAP Excluding intercompany transactions eliminated in consolidation *** Net Income refers to Net income attributable to stockholders of Overstock.com, Inc. *** Net Income $12.5 Million (vs. $2.4 million in 2015) Gross Margin 18.4% (vs. 18.4% in 2015) Tech and G&A Expense $196.1 Million (8% increase vs. 2015) TTM Operating Cash Flow $39.6 Million (vs. $54.5 million in 2015) 10#112016 Annual Results - Retail Only (Direct and Partner) * Non-GAAP Revenue $1.8 Billion (8% increase vs. 2015) Contribution Dollars* $195.8 Million (6% increase vs. 2015) overstock.com Gross Profit Dollars $326.4 Million (8% increase vs. 2015) Contribution Margin* 11.0% (vs. 11.1% in 2015) Gross Margin 18.3% (vs. 18.3% in 2015) Pre-Tax Income $32.3M (vs. pre-tax income of $10.1M in 2015) 11#12Corporate Employees 1,400 1,200 1,000 800 600 400 200 0 1,044 Q4-14 Q1-15 overstock.com® Q2-15 Corporate employees excludes customer service and warehouse staff. Q3-15 ■ Tech 1,137 Q4-15 Non-Tech Q1-16 Q2-16 Q3-16 1,177 Q4-16 12#13Operating and Free Cash Flow (TTM) ($,000) 100,000 80,000 60,000 40,000 20,000 0 (20,000) (40,000) 80,834 39,488 17,811 Q4-14 Q1-15 overstock.com Q2-15 Q3-15 54,516 * * Non-GAAP: Free Cash Flow = Cash Flow from Operations less Expenditures for Fixed Assets. 37,437 (4,997) Q4-15 Q1-16 Q2-16 Q3-16 Cash flow from operations (TTM) Free cash flow* (TTM) Cash paid for new headquarters construction (TTM) 43,744 39,564 (32,717) Q4-16 13#14GAAP TTM Inventory Turns and GMROI 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0.0 41.8 958% Q4-14 Q1-15 overstock.com Q2-15 Q3-15 TTM Inventory turns TTM Inventory Turns = TTM COGS / Average Inventory. TTM GMROI = TTM Gross Margin % * TTM Revenue / Average Inventory 53.3 1200% Q4-15 Q1-16 Q2-16 TTM GMROI Q3-16 69.3 1563% Q4-16 2000% 1800% 1600% 1400% 1200% 1000% 800% 600% 400% 200% 0% 14#15Customer Orders and Average Order Size* (#,000) 4,000 3,500 3,000 2,500 2,000 1,500 1,000 500 3,454 $159 Q4-14 Q1-15 loverstock.com Q2-15 Customer orders Q3-15 3,463 $162 Q4-15 Average Order Size is measured at the time of order, before promotional discounts and shipping revenue. Q1-16 Q2-16 Average order size* Q3-16 3,465 $181 Q4-16 $250 $200 $150 $100 $50 $0 15#16Unique Customers and Cost Per Customer (#,000) 3,000 2,500 2,000 1,500 1,000 500 2,480 $14.96 Q4-14 loverstock.com® Q1-15 Unique customers Q2-15 Q3-15 2,423 $15.83 Q1-16 Q2-16 Marketing $ / unique customers (cost per customer) Q4-15 Q3-16 2,372 $20.40 Q4-16 $40.00 $35.00 $30.00 $25.00 $20.00 $15.00 $10.00 $5.00 16#17Wayfair Comparison - Visits and Ad Spend Total Visits (in millions) 450 400 350 300 250 200 150 100 50 $55 $35 Q4 14 $58 Visits and Ad Spend Q1 15 $62 $26 Fri $26 Q2 15 $71 Note: Ad Spend data source: Overstock and Wayfair 10-Qs; Visit data source: Hitwise, a division of Connexity overstock.com $28 Q3 15 Wayfair Total Visits (M) -Wayfair Ad Spend ($M) $88 $36 $98 $94 $29 TIT Q4 15 $30 $101 Q2 16 $32 Q1 16 Overstock Total Visits (M) Overstock Ad Spend ($M) Q3 16 1 Q4 16 $120 $100 $80 $60 $40 $20 Ad Spend (in millions) 17#18Wayfair Comparison - Ad Spend / Visit $1.00 $0.90 $0.80 $0.70 $0.60 $0.50 $0.40 $0.30 $0.20 $0.10 $0.94 $0.34 Q4 14 $0.88 $0.28 Q1 15 Ad Spend / Visit Note: Ad Spend data source: Overstock and Wayfair 10-Qs; Visit data source: Hitwise, a division of Connexity overstock.com $0.88 $0.29 Q2 15 $0.84 $0.32 Q3 15 -Wayfair Ad Spend/Visit $0.90 $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 18#19Wayfair Comparison - YoY Visit Growth 80% 70% 60% 50% 40% 30% 20% 10% 0% 67% 8% Q4 15 Note: Visit data source: Hitwise, a division of Connexity overstock.com YoY Visit Growth 65% 8% Q1 16 Wayfair Visit Growth 50% 6% Q2 16 43% 14% Q3 16 •Overstock Visit Growth 35% 8% Q4 16 19#20Wayfair Comparison - Pre-Tax Income (Loss) $60,000 $30,000 $- $(30,000) $(60,000) $(90,000) $(120,000) $(150,000) $(180,000) $15,154 $(21,005) overstock.com 2012 $16,344 Note: Source: Overstock and Wayfair 10-Ks and 10-Qs $(15,480) 2013 $13,205 T $(147,923) 2014 Overstock Retail Pre-Tax Income $10,092 $(77,348) 2015 $25,490 $(149,864) 2016 (thru Q3) Wayfair Pre-Tax Income 20#21I Medici Structure SPEEDROUTE R4 DATA IFX to T ZERO FUSION IQ T ZERO TECHNOLOGIES PRO ATS BLUE OCEAN TECHNOLOGIES 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. PEERNOVA Acquisition (Aug 2015): $30M Other: $10M OSTK Ownership: 81% loverstock.com PeerNova builds immutable systems for large scale commercial applications. Date: Jan 2015 Investment: $5.6M Ownership: 7.5% A MEDICI VENTURES bitt The Bitt wallet provides a quick, secure and easy way to manage your funds; giving you freedom to do more with your money. Date: Apr 2016 Investment: $4M Ownership: 11.4% SettleMint Settle Mint seeks to develop blockchain solutions for voting and land titling. Date: Jan 2017 Investment: €0.3M Ownership: 30% factom Factom seeks to develop blockchain solutions for mortgage compliance and land titling. Date: Dec 2016 Investment: $750K Ownership: 2.5% IdentityMind GLOBAL Digital Identities You Can Trust IdentityMind's mission is to construct electronic identities and infuse integrity back into the global market of digital commerce. Date: Apr 2015 Investment: $1.2M Ownership: 5.0% 21#22to - First Public Blockchain Equity Offering Completed ● ● ● ● ● ● ● ● ● October 2014 - Announcement of Medici June 2015 - Cryptobond I August 2015 - Cryptobond II August 2015 - Announcement of Speed Route 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 December 2016 - First Ever Blockchain Equity Offering Completed! loverstock.com® 22#23loverstock.com Email all questions to: [email protected] f Follow Us On You Tube 8+ 23