#1460380 40360 40 Oloverstock.com Q2 2016 Financial Results#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#3Q2 2016 Results Revenue $418.5 Million (8% increase vs. Q2 2015) Contribution Dollars* $46.9 Million (0% increase vs. Q2 2015) Pre-Tax Income (Loss) ($1.5) million (vs. $3.3 million in Q2 2015) Gross Profit Dollars $76.3 Million (4% increase vs. Q2 2015) overstock.com Contribution Margin* 11.2% (vs. 12.1% in Q2 2015) Net Income (Loss)** ($904,000) (vs. $1.7 million in Q2 2015) * Non-GAAP ** Net Income (loss) refers to Net income (loss) attributable to stockholders of Overstock.com, Inc. Gross Margin 18.2% (vs. 19.0% in Q2 2015) Tech and G&A Expense $48.5 Million (11% increase vs. Q2 2015) TTM Operating Cash Flow $75.4 Million (vs. $62.3 million in Q2 2015) 3#4Quarterly Revenue and Growth ($,000) 500,000 450,000 400,000 350,000 300,000 250,000 200,000 150,000 100,000 50,000 332,545 13% Q2-14 loverstock.com® Q3-14 Q4-14 Q1-15 Revenue ($) 388,013 17% Q2-15 Q3-15 Q4-15 Revenue growth (yoy) Q1-16 418,540 8% Q2-16 40% 35% 30% 25% 20% 15% 10% 5% 0% 4#5Quarterly Gross Profit and Growth ($,000) 90,000 80,000 70,000 60,000 50,000 40,000 30,000 20,000 10,000 0 (10,000) 62,625 8% Q2-14 loverstock.com® Q3-14 Q4-14 Q1-15 Gross profit ($) 73,657 18% Q2-15 Q3-15 Q4-15 Gross profit growth (yoy) Q1-16 76,322 4% Q2-16 45% 40% 35% 30% 25% 20% 15% 10% 5% 0% -5% 81 5#6Quarterly Contribution and Growth* ($,000) 60,000 50,000 40,000 30,000 20,000 10,000 0 (10,000) 39,595 2% Q2-14 Q3-14 loverstock.com IHO 18% Q4-14 Contribution ($) 46,777 Q1-15 Q2-15 Q4-15 Contribution growth (yoy) Q3-15 * Non-GAAP: Contribution dollars = Gross profit less Sales & Marketing expense plus Club O Rewards and Gift Card breakage. Q1-16 46,885 0% Q2-16 60% 50% 40% 30% 20% 10% 0% -10% 6#7Quarterly 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% 18.8% 11.9% Q2-14 Q3-14 loverstock.com Q4-14 Q1-15 Gross margin 19.0% 12.1% Q2-15 Q3-15 Contribution margin Q4-15 Q1-16 * Non-GAAP: Contribution margin = Gross profit less Sales & Marketing expense plus Club O Rewards and Gift Card breakage as a percentage of revenue. 18.2% 11.2% Q2-16 7#8Technology and G&A Expenses $s and % of Revenue ($,000) 70,000 60,000 50,000 40,000 30,000 20,000 10,000 11.2% 37,289 Q2-14 loverstock.com G&A Q3-14 $4.6 M Q4-14 Q1-15 Legal Case Judgments 11.2% 43,488 Q2-15 Q3-15 Technology Q4-15 Q1-16 11.6% 48,478 Q2-16 G&A and Tech (% of revenue) 12.0% 10.0% 8.0% 6.0% 4.0% 2.0% 0.0% 8#9Corporate Employees 1,400 1,200 1,000 800 600 400 200 937 1 Q2-14 Q3-14 overstock.com® Q4-14 Q1-15 Corporate employees excludes customer service and warehouse staff. 1,048 Q2-15 Q3-15 Q4-15 Q1-16 1,130 Q2-16 9#10Operating and Free Cash Flow (TTM) ($,000) 90,000 80,000 70,000 60,000 50,000 40,000 30,000 20,000 10,000 (10,000) (20,000) 50,825 26,975 Q2-14 Q3-14 overstock.com 62,266 Q4-14 Q1-15 Cash flow from operations (TTM) * Non-GAAP: Free Cash Flow = Cash Flow from Operations less Expenditures for Fixed Assets. * Q2-15 16,960 Q4-15 Free cash flow* (TTM) Q3-15 Q1-16 75,401 (7,921) Q2-16 10#11GAAP TTM Inventory Turns and GMROI 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0.0 49.9 1152% Q2-14 Q3-14 overstock.com Q4-14 Q1-15 TTM Inventory turns TTM Inventory Turns TTM COGS / Average Inventory TTM GMROI = TTM Gross Margin % * TTM Revenue / Average Inventory 50.3 1159% Q2-15 Q3-15 Q4-15 TTM GMROI Q1-16 57.3 1269% Q2-16 2000% 1800% 1600% 1400% 1200% 1000% 800% 600% 400% 200% 0% 11#12Unique Customers and Cost Per Customer (#,000) 3,000 2,500 2,000 1,500 1,000 500 1,591 $14.79 Q2-14 loverstock.com® Q3-14 Unique customers Q4-14 Q1-15 1,752 $16.03 Q2-15 Q3-15 Q4-15 Marketing $ / unique customers (cost per customer) Q1-16 1,816 $18.36 Q2-16 $40.00 $35.00 $30.00 $25.00 $20.00 $15.00 $10.00 $5.00 12#13Customer Orders and Average Order Size* (#,000) 4,000 3,500 3,000 2,500 2,000 1,500 1,000 500 2,126 $177 Q2-14 Q3-14 overstock.com Q4-14 Customer orders Q1-15 2,435 $185 Q2-15 Average Order Size is measured at the time of order, before promotional discounts and shipping revenue. Q3-15 Q4-15 Average order size* Q1-16 2,602 $189 Q2-16 $400 $350 $300 $250 $200 $150 $100 $50 $0 13#14RETAIL President: Saum Noursalehi loverstock.com Overstock.com MEDICI President: Jonathan Johnson • te Speed Route Bitt • PeerNova Identity Mind ● ● ● OTHER Peace Coliseum View Marka VIP 14#15loverstock.com Email all questions to: [email protected] f Follow Us On You Tube 8+ 15