#1overstock.com Overstock.com, Inc. Q1 2015 Financial Results April 27, 2015 1#2overstock.com Safe 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 difficulties we may encounter as a result of accepting Bitcoin as payment, 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 expectations regarding the benefits and risks of the credit facility we recently entered into for the purpose of, among other things, financing our construction of an office campus to serve as our corporate headquarters, 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 Annual Report on Form 10-K for the year ended December 31, 2014, which was filed with the Securities and Exchange Commission on March 12, 2015. 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. 2#3overstock.com * Q1 2015 Results Revenue - $398.3 million (17% increase vs. Q1 2014) Gross profit dollars - $75.4 million (18% increase vs. Q1 2014) Gross margin - 18.9% (vs. 18.8% in Q1 2014) Contribution dollars* - $47.5 million (17% increase vs. Q1 2014) Contribution margin* - 11.9% (vs. 11.9% in Q1 2014) Tech and G&A expense - $43.6 million (25% increase vs. Q1 2014) Pre-tax income - $4.5 million (vs. $6.6 million in Q1 2014) Net income** - $2.7 million (vs. $4.0 million in Q1 2014) TTM Operating cash flow - $67.4 million (vs. $55.6 million in Q1 2014) Non-GAAP ** Net Income refers to Net Income attributable to stockholders of Overstock.com, Inc. 3#4overstock.com ($,000) 500,000 450,000 400,000 350,000 300,000 250,000 200,000 150,000 100,000 50,000 0 Revenue ($) Revenue growth (yoy) 311,994 19% Q1-13 Q2-13 Quarterly Revenue Growth 341,207 9% Q3-13 Q4-13 Q1-14 Q2-14 Q3-14 Q4-14 398,344 17% Q1-15 50% 45% 40% 35% 30% 25% 20% 15% 10% 5% 0% 4#5($,000) 90,000 80,000 70,000 60,000 50,000 40,000 30,000 20,000 overstock.com 10,000 0 Gross profit ($) Gross profit growth (yoy) 58,936 24% Quarterly Gross Profit Growth 63,996 9% Q1-13 Q2-13 Q3-13 Q4-13 Q1-14 75,437 18% Q2-14 Q3-14 Q4-14 Q1-15 LO 5 60% 50% 40% 30% 20% 10% 0%#6($,000) 50,000 40,000 30,000 20,000 10,000 overstock.com 0 Contribution ($) Contribution growth (yoy) 40,231 Quarterly Contribution & Growth * 22% 40,604 PIL 1% Q1-13 Q2-13 Q3-13 Q4-13 Q1-14 Q2-14 * Contribution dollars = Gross profit less Sales & Marketing expense Q3-14 Q4-14 47,465 50% 17% Q1-15 40% 30% 20% 10% 0% -10% 6#725.0% 20.0% 15.0% 10.0% 5.0% 0.0% overstock.com 18.9% 12.9% 19.7% 13.2% Gross margin Contribution margin 19.6% 18.0% Q1-14 marketing: 6.9% 12.2% 10.2% Quarterly Gross Margin and Contribution Margin* 18.8% 18.8% 11.9% 11.8% * Contribution margin = Gross margin less Sales & Marketing percentage. 19.0% 18.2% Q1-15 marketing: 7.0% 11.8% 10.3% 18.9% 11.9% Q1-13 Q2-13 Q3-13 Q4-13 Q1-14 Q2-14 Q3-14 Q4-14 Q1-15 7#8overstock.com Overstock contribution margin Amazon contribution margin Amazon product contribution margin (excludes service sales) o Wayfair contribution margin 25.0% 20.0% 15.0% 12.9% 10.0% 5.0% 0.0% -5.0% -10.0% -15.0% -20.0% 11.5% O 5.5% -7.2% 13.2% 12.6% 6.0% -7.6% 12.2% 11.7% 5.1% -9.3% 10.7% 10.2% 4.3% Contribution Margin vs. Amazon.com and Wayfair.com* -8.5% 12.7% 11.9% -1.8% -9.8% Q1-13 Q2-13 Q3-13 Q4-13 Q1-14 13.5% 11.8% O 0.2% -9.7% 11.3% 11.8% 0.5% -14.0% 12.6% 10.3% O -3.2% -10.9% 11.9% Q2-14 Q3-14 Q4-14 Q1-15 *Overstock.com Contribution Margin = Gross profit less Sales & Marketing divided by Total net revenue. *Amazon.com Contribution Margin = Total net sales less Cost of Sales, Fulfillment, and Marketing divided by Total net sales. *Amazon.com Product Contribution Margin = Total product sales less Cost of Sales, Fulfillment, and Marketing divided by Total product sales. *Wayfair.com Contribution Margin = Gross profit less Sales & Marketing divided by Total net revenue. 8#9overstock.com ($,000) 60,000 50,000 40,000 30,000 20,000 10,000 G&A G&A and Tech (% of revenue) 10.7% 33,248 5.8% 4.8% Technology and G&A Expenses $s and % of Revenue Legal Case Judgments G&A (% of revenue) $6.3M 10.2% 34,897 5.7% 4.5% Technology Technology (% of revenue) $4.6M 11.0% 43,621 5.8% 5.2% Q1-13 Q2-13 Q3-13 Q4-13 Q1-14 Q2-14 Q3-14 Q4-14 Q1-15 12.0% 10.0% 8.0% 6.0% 4.0% 2.0% 0.0% 9#10overstock.com ($,000) 75,000 70,000 65,000, 10,000 8,000 6,000 4,000 2,000 * 0 7,697 Q1-13 11 Q2-13 Quarterly Net Income* 3,970 Q3-13 Q4-13 Q1-14 Net Income refers to Net income attributable to stockholders of Overstock.com, Inc. Q4 2013 includes $68.5 million net impact of deferred tax asset valuation release. Q2-14 Q3-14 Q4-14 2,739 Q1-15 10#11overstock.com® ($,000) 90,000 80,000 70,000 60,000 50,000 40,000 30,000 20,000 10,000 0 Cash flow from operations (TTM) ■Free cash flow* (TTM) 48,726 32,302 Operating & Free Cash Flow* (TTM) * Non-GAAP 55,619 37,419 67,424 25,661 Q1-13 Q2-13 Q3-13 Q4-13 Q1-14 Q2-14 Q3-14 Q4-14 Q1-15 11#1260.0 50.0 40.0 30.0 20.0 10.0 0.0 overstock.com 44.6 Inventory turns Inventory turns (direct only) 6.7 GAAP TTM Inventory Turns Q1-13 Q2-13 Q3-13 Q4-13 TTM Inventory Turns: TTM COGS / Average Inventory 45.1 5.5 Q1-14 Q2-14 Q3-14 Q4-14 47.6 4.8 Q1-15 12#13overstock.com 1400% 1200% 1000% 800% 600% 400% 200% 0% * GMROI (TTM) -GMROI (direct only TTM) 997% 78% 1054% 83% Q1-13 Q2-13 Q3-13 Q4-13 GMROI (TTM) = TTM GM% * TTM Revenue / Average Inventory TTM GMROI* Q1-14 Q2-14 Q3-14 1095% 64% Q4-14 Q1-15 13#14overstock.com (#,000) 3,000 2,500 2,000 1,500 1,000 500 0 Unique customers Marketing $ / unique customers (cost per customer) 1,733 Unique Customers & Cost per Customer $10.79 1,774 $13.19 1,901 $14.72 Q1-13 Q2-13 Q3-13 Q4-13 Q1-14 Q2-14 Q3-14 Q4-14 Q1-15 $50.00 $45.00 $40.00 $35.00 $30.00 $25.00 $20.00 $15.00 $10.00 $5.00 $- 14#15overstock.com (#,000) 1,500 1,200 900 600 300 0 854 Q1-13 Q2-13 Q3-13 Q4-13 868 New Customers Q1-14 Q2-14 Q3-14 Q4-14 901 Q1-15 15#16overstock.com Customer Orders & Average Order Size (#,000) 4,000 3,500 3,000 2,500 2,000 1,500 1,000 500 0 B2C customer orders Average order size 2,235 $153 2,352 $165 Q1-13 Q2-13 Q3-13 Q4-13 Q1-14 Q2-14 Q3-14 2,630 $174 Q4-14 Q1-15 $350 $300 $250 $200 $150 $100 $50 $0 16#17$35.00 $30.00 $25.00 $20.00 $15.00 $10.00 $5.00 $0.00 overstock.com $26.37 Gross Profit per Transaction. Q1-13 Q2-13 Q3-13 Q4-13 $27.21 $28.69 Q1-14 Q2-14 Q3-14 Q4-14 Q1-15 17#181,200 1,000 800 600 400 200 0 overstock.com 767 Q1-13 Q2-13 Q3-13 Q4-13 889 Corporate Employees Q1-14 Q2-14 Q3-14 Q4-14 1,002 Q1-15 18#19overstock.com A Farmers Market B - Overstock Fulfillment Services C - Supplier Oasis D - International E - Loyalty F - Medici Key Innovations 19#20overstock.com Questions 20