#1.. .. .. N .. 20 4 .. 34 Ooverstock.com Q1 2017 Financial Results 1799#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, adverse tax, regulatory or legal developments, consumer or regulatory claims regarding the products we offer or sell, the extent to which we owe taxes or are required to collect sales or similar taxes in jurisdictions in which we do not do so, competition, fluctuations in our operating results, any inability to raise capital or borrow funds on acceptable terms, difficulties we may have with our efforts to expand both domestically and internationally, and risks of inventory management and seasonality. Other risks and uncertainties include, among others, risks related to the business our subsidiary Medici Ventures, Inc. is pursuing, our continually evolving business model, and difficulties we may have 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-K for the year ended December 31, 2016 which was filed with the Securities and Exchange Commission on March 3, 2017. The Form 10-K and our subsequent filings with the Securities and Exchange Commission identify important factors that could cause our actual results to differ materially from those contained in or contemplated by our projections, estimates and other forward-looking statements.. loverstock.com® 2#3Q1 2017 Results - OSTK Total Revenue $432.4 Million (5% increase vs. Q1 2016) Contribution Dollars* $50.0 Million (0% decrease vs. Q1 2016) Pre-Tax Income (Loss)*** ($6.6) Million $1.4M Retail** ($8.0M) - Medici** (vs. $22.1 million in Q1 2016) $25.1M - Retail** ($3.0M) - Medici** Gross Profit Dollars $86.9 Million (12% increase vs. Q1 2016) loverstock.com Contribution Margin* 11.6% (vs. 12.1% in Q1 2016) Net Income (Loss)" ($5.9) Million (vs. $13.4M in Q1 2016) * Non-GAAP - see discussion and reconciliation in our earnings press release ** Excluding intercompany transactions eliminated in consolidation *** Q1 2017 pre-tax results include an impairment charge of $4.5M related to a cost method investment **** Net Income refers to Net income attributable to stockholders of Overstock.com, Inc. **** Gross Margin 20.1% (vs. 18.7% in Q1 2016) Tech and G&A Expense $51.6 Million (9% increase vs. Q1 2016) TTM Operating Cash Flow $51.0 Million (vs. $63.1 million in Q1 2016) 3#4Q1 2017 Results - Retail Only (Direct and Partner) Revenue $428.1 Million (4% increase vs. Q1 2016) Contribution Dollars* $49.2 Million (0% increase vs. Q1 2016) Gross Profit Dollars loverstock.com $85.8 Million (13% increase vs. Q1 2016) Contribution Margin* * Non-GAAP - see discussion and reconciliation in our earnings press release ** Q1 2016 results include a litigation settlement received of $19.5M 11.5% (vs. 11.9% in Q1 2016) Gross Margin 20.0% (vs. 18.5% in Q1 2016) Pre-Tax Income $1.4M (vs. $25.1M in Q1 2016)** 4#5Marketing Spend as a % of sales (per Internet Retailer) How digital marketing spend relates to sales for top e-retailers Internet Retailer, Stefany Zaroban, April 5, 2017 How Marketing Spend Relates to Sales for Top Web-Only Merchants Retailer 2014 2015 2016 Amazon.com Inc. Etsy Inc. Wayfair Inc. Groupon Inc. Overstock Inc. Cimpress Shutteryfly Inc. 1-800 Flowers.com Inc. U.S. Auto Parts Network PetMed Express Inc. CafePress.com Source: Internet Retailer analysis of retailer's public filings. https://www.digital 4.7% 19.2% 23.7% 8.4% 7.0% 19.6% 29.4% 28.0% 14.7% 12.4% 26.4% commerce360.com/2017/04/05/digital-marketing-spend-relates-sales-top-e-retailers/ loverstock.com 4.9% 23.7% 14.5% 7.8% 7.3% 32.9% 27.0% 31.6% 14.4% 9.7% 21.5% 5.1% 20.4% 17.7% 12.2% 7.8% 30.3% 23.6% 31.7% 14.2% 7.7% 22.8% 01 5#6Wayfair Comparison - Total Visits Total Visits (in millions) 450 400 350 300 250 200 150 100 50 Q4 14 overstock.com Q1 15 Visit data source: Hitwise, a division of Connexity Total Visits Q2 15 ■Wayfair Total Visits (M) Q3 15 Q4 15 Q1 16 Q2 16 ■Overstock Total Visits (M) Q3 16 Q4 16 6#7Wayfair Comparison - Visits and Ad Spend Total Visits (in millions) 450 400 350 300 250 200 150 100 50 $55 overstock.com $35 Q4 14 $58 $26 Q1 15 Visits and Ad Spend $26 T Q2 15 Ad Spend data source: Overstock and Wayfair 10-Ks and 10-Qs Visit data source: Hitwise, a division of Connexity $62 $71 $28 Q3 15 Wayfair Total Visits (M) -Wayfair Ad Spend ($M) $88 $36 Q4 15 $98 $29 $94 $30 $101 $32 Q1 16 Q2 16 Q3 16 Overstock Total Visits (M) -Overstock Ad Spend ($M) $116 $44 Q4 16 $140 $120 $100 $80 $60 $40 $20 Ad Spend (in millions) 7#8Wayfair 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 $0.88 Q2 15 Ad Spend data source: Overstock and Wayfair 10-Ks and 10-Qs Visit data source: Hitwise, a division of Connexity loverstock.com $0.29 $0.84 $0.32 Q3 15 Wayfair Ad Spend/Visit $0.90 $0.32 Q4 15 $0.90 $0.29 Q1 16 $0.90 $0.32 Q2 16 -Overstock Ad Spend/Visit $0.84 $0.32 Q3 16 $0.88 $0.38 Q4 16 8#9Wayfair Comparison Brand Awareness. Brand Awareness 100% 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% 93% loverstock.com 79% ■Overstock ■Wayfair U.S. Aided Awareness Source: Overstock brand tracker- LRW (Lieberman Research Worldwide), Dec 2016 30% more shoppers associate Overstock with 'lower prices' Equal or better perceptions of 'quality for the price' 9#10Wayfair Comparison Customer Acquisition Cost $80 $70 $60 $50 $40 $30 $20 $10 $0 $38 $68 2016 ■ Overstock ■Wayfair Customer Acquisition Cost = Total Advertising Spend divided by Implied New Customers ((1-% of orders from Repeat Customers) * Total Orders) Source: Overstock and Wayfair 2016 10-Ks and Investor Presentations loverstock.com 10#11Wayfair Comparison - Customer Loyalty 80.0% 70.0% 60.0% 50.0% 40.0% 30.0% 20.0% 62.8% 47.3% 63.3% 48.0% 63.1% 63.0% loverstock.com 47.1% 46.8% 64.0% 50.7% 65.0% 51.6% 64.8% 49.8% 65.3% 50.3% 67.2% Sources: Wayfair Q4 '16 Investor Presentation and Overstock internal data (Home & Garden only) 53.9% Overstock % of Orders from Repeat Customers (Home & Garden) 68.4% 56.6% 68.1% 55.2% 68.8% 54.3% 69.3% 55.4% 70.0% 57.6% 69.7% 2013-Q1 2013-Q2 2013-Q3 2013-Q4 2014-Q1 2014-Q2 2014-Q3 2014-Q4 2015-Q1 2015-Q2 2015-Q3 2015-Q4 2016-Q1 2016-Q2 2016-Q3 2016-Q4 Wayfair % of Orders from Repeat Customers 56.9% 71.0% 58.0% 11#12Wayfair Revenue & Advertising Growth 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% 48% 38% Q4-14 Source: Wayfair 10-Ks and 10-Qs overstock.com 52% 31% Q1-15 66% 45% Q2-15 77% 42% Q3-15 Wayfair Revenue Growth 81% 61% Q4-15 76% 68% Q1-16 60% 53% Q2-16 45% 43% Q3-16 Wayfair Advertising Growth 33% 32% Q4-16 12#13Wayfair Comparison - Contribution Margin 14.0% 12.0% 10.0% 8.0% 6.0% 4.0% 2.0% 0.0% -2.0% -4.0% 10.5% -3.2% Q4-14 12.1% 1.3% Q1-15 12.1% 3.5% Q2-15 11.2% 3.8% Q3-15 9.8% 4.0% Q4-15 Overstock contribution margin 12.1% 2.2% Q1-16 11.2% 2.6% Q2-16 11.1% 2.1% Q3-16 Wayfair contribution margin 10.3% 3.9% Q4-16 Non-GAAP Overstock Contribution Margin = Gross profit less Sales & Marketing plus Club O Rewards and gift card breakage, divided by Total net revenue Wayfair Contribution Margin = Gross profit less Customer service and merchant fees, Advertising, and Merchandising, marketing and sales, divided by Total net revenue Source: Overstock and Wayfair 10-Ks and 10-Qs overstock.com 13#14Wayfair Comparison - Net Revenue per Employee ($,000) $350 $300 $250 $200 $150 $100 $50 $- $271 $174 Q4-14 $251 $167 Q1-15 $232 $172 Q2-15 $216 $183 Q3-15 Net Revenue divided by total number of employees (as of period end) Source: Overstock and Wayfair 10-Ks, 10-Qs, and Earnings Conference Calls loverstock.com $248 $194 Q4-15 Overstock Net Revenue per Employee $228 $162 Q1-16 $239 $146 Q2-16 $261 $154 Q3-16 $298 $175 Q4-16 -Wayfair Net Revenue per Employee 14#15Wayfair Comparison - Net Revenue per Employee ($,000) $1,200 $1,000 $800 $600 $400 $200 $- $869 $588 2013 $881 Net Revenue divided by total number of employees (as of period end) Source: Overstock and Wayfair 10-Ks loverstock.com $561 2014 Overstock Net Revenue per Employee $873 $591 2015 $1,000 $600 2016 -Wayfair Net Revenue per Employee 15#16Wayfair Comparison - Contribution vs. Breakeven ($,000) $300,000 $250,000 $200,000 $150,000 $100,000 $50,000 $- $(50,000) 2012 HI 2013 Overstock Retail Contribution $ 2014 2015 2016 Contribution $ needed to breakeven (pre-tax) ($,000) $300,000 $250,000 $200,000 $150,000 $100,000 $50,000 $- $(50,000) 2012 Wayfair Contribution $ Non-GAAP Overstock Retail Contribution = Gross profit less Sales & Marketing plus Club O Rewards and gift card breakage (retail only) Wayfair Contribution = Gross profit less Customer service and merchant fees, Advertising, and Merchandising, marketing and sales Source: Overstock and Wayfair 10-Ks and 10-Qs loverstock.com 2013 2014 2015 2016 Contribution $ needed to breakeven (pre-tax) 16#17Wayfair Comparison - Days Payable Outstanding (DPO) 45.0 40.0 35.0 30.0 25.0 20.0 15.0 10.0 5.0 35.5 21.3 Q1-15 36.2 21.4 Q2-15 37.9 21.0 Q3-15 38.7 TTM Avg. Accounts Payable divided by TTM Cost of Goods Sold/360 Source: Overstock and Wayfair 10-Ks and 10-Qs loverstock.com 21.5 Q4-15 Overstock DPO 39.7 22.1 Q1-16 40.4 22.3 Q2-16 -Wayfair DPO 41.4 22.9 Q3-16 42.3 21.4 Q4-16 17#18Wayfair Comparison - Accounts Payable % of Cash 120% 100% 80% 60% 40% 20% 0% 62% 36% Q4-14 54% 44% Q1-15 65% 52% Q2-15 80% 59% Q3-15 -Overstock Accounts Payable % of Cash Overstock - Accounts Payable divided by Cash & Cash Equivalents Wayfair - Accounts Payable divided by Cash & Cash Equivalents plus Short Term Investments Source: Overstock and Wayfair 10-Ks and 10-Qs overstock.com 72% 70% Q4-15 81% 62% Q1-16 88% 64% Q2-16 107% 68% Q3-16 -Wayfair Accounts Payable % of Cash 109% 58% Q4-16 18#19Wayfair Comparison - Change in Working Capital ($,000) $350,000 $250,000 $150,000 $50,000 $(50,000) $(150,000) $(250,000) Oct 2014 Wayfair IPO $236,158 $(10,165) 2014 Overstock Change in Working Capital Working Capital = Current Assets less Current Liabilities Source: Overstock and Wayfair 10-Ks loverstock.com® $(25,568) $(158,979) 2015 $21,733 $(175,426) 2016 -Wayfair Change in Working Capital 19#20Wayfair Comparison - Working Capital ($,000) $300,000 $250,000 $200,000 $150,000 $100,000 $50,000 $- $(50,000) $(100,000) $(150,000) $15,260 $254,276 Oct 2014 Wayfair IPO 2014 $(10,308) Working Capital = Current Assets less Current Liabilities Source: Overstock and Wayfair 10-Ks loverstock.com $95,297 2015 $11,425 ■Overstock Working Capital ■Wayfair Working Capital $(80,129) 2016 20#21Wayfair Comparison - Gross Margin 25.0% 20.0% 15.0% 10.0% 5.0% 0.0% 20.3% 18.7% Q1-16 20.1% 18.2% Q2-16 Overstock Gross Margin Non-GAAP Overstock Gross Margin = Gross profit divided by Total net revenue Wayfair Gross Margin = Gross profit less Customer service and merchant fees, divided by Total net revenue Source: Overstock and Wayfair 10-Ks and 10-Qs loverstock.com 19.5% 18.1% Q3-16 -Wayfair Gross Margin 20.5% 18.6% Q4-16 21#22Wayfair Comparison - Pricing Strategy *wayfair A AM AN A M MA ANAK 771 ANAK nh Source: Overstock and Wayfair website screenshots loverstock.com Shell Matte Side Chair by eModern Decor 305 Reviews 9 Questions Answered $269.99 Payments as low as $24/month. Learn More Save $40 on your $250 order with the Wayfair Credit Card. Apply Now AM AM AN AM M AN MMA AD overstock Edgemod Vortex Dining Chair with Walnut Legs (Set of 4) Today: $156.99 At other retaller: $276.80 Save $119.81 (43%) Add Professional Installation Leam More White - $156.99 Quantity: 1 ITEM# 18645083 55 Reviews Delivery Estimate Club O Gold Members Eurn $15.70 | 10% Rewards* Warranty Notifications FREE SHIPPING* Add to Cart Standard Friday, May 5 FREE Included Warranty: 1 year Limited Manufacturer 22 TM#23Wayfair Comparison - Price Paid by Consumer Difference in average price per item paid by consumers (net of discounts) for products sold by both Overstock and Wayfair – weighted by Overstock units sold 0.0% -5.0% -10.0% -15.0% -20.0% -25.0% -30.0% -18.4% overstock.com Q1-16 -19.8% Q2-16 Source: Overstock internal sales data and price scrapes from a 3rd party pricing intelligence tool. -23.8% Q3-16 -% Difference in Average Price Paid by Consumer -21.0% Q4-16 23#24Wayfair Comparison Price Paid by Consumer Difference in average price per item paid by consumers (net of discounts) for products sold by both Overstock and Wayfair - weighted by Wayfair review counts. 0.0% -5.0% -10.0% -15.0% -20.0% -25.0% -30.0% -9.8% Q1-16 -10.5% Q2-16 -12.4% Source: Overstock internal sales data and review scrapes from a 3rd party pricing intelligence tool. overstock.com Q3-16 -% Difference in Average Price Paid by Consumer -7.5% Q4-16 24#25Wayfair Comparison - Pre-Tax Income (Loss) ($,000) $50,000 $- $(50,000) $(100,000) $(150,000) $(200,000) $(250,000) $15,154 $(21,005) overstock.com 2012 Source: Overstock and Wayfair 10-Ks and 10-Qs $16,344 $(15,480) 2013 $13,205 $(147,923) 2014 Overstock Retail Pre-Tax Income $10,092 $(77,348) 2015 Wayfair Pre-Tax Income $32,332 $(193,767) 2016 25#26Wayfair Summary Total Visits (in millions) 0.0% -5.0% -10.0% -15.0% -20.0% -25.0% -30.0% 450 400 350 300 250 200 150 100 50 90% 80% 70% 60% 50% 40% 30% 20% 10% 0% 48% $55 38% Difference in average price per item paid by consumers (net of discounts) for products sold by both Overstock and Wayfair - weighted by Overstock units sold Q4-14 -18.4% $35 $26 HH Q4 14 Q1 15 Q1-16 $58 52% 31% Q1-15 $62 overstock.com $26 Q2 15 Visits and Ad Spend 66% -19.8% →→→% Difference in Average Price Paid by Consumer Q2-16 45% Q2-15 $71 Wayfair Total Visits (M) -Wayfair Ad Spend ($M) $28 Q3 15 77% 42% Q3-15 --Wayfair Revenue Growth $88 $36 04 15 81% 61% Q4-15 $98 $29 -23.8% Q3-16 Q1 16 76% 68% $94 Q1-16 $30 Q2 16 Overstock Total Visits (M) Overstock Ad Spend ($M) 60% 53% $101 Q2-16 $32 Q3 16 45% 43% Q3-16 -21.0% Q4-16 $116 $44 Q4 16 --Wayfair Advertising Growth 33% 32% $140 $120 $100 $80 $60 $40 $20 Q4-16 $- Ad Spend (in millions) ($,000) $300,000 $250,000 $200,000 $150,000 $100,000 $50,000 $(50,000) 120% 100% 80% 60% 40% 20% $ 0% ($,000) $50,000 $ $(50,000) $(100,000) $(150,000) $(200,000) $(250,000) Wayfair Contribution $ 62% 36% 2012 Q4-14 54% Q1-15 $15,154 44% 2012 $(21,005) 2013 65% 52% Q2-15 →→-Overstock Accounts Payable % of Cash $16,344 80% 2013 59% -Contribution $ needed to breakeven (pre-tax) Q3-15 $(15,480) 2014 72% 70% $13,205 $(147,923) 81% 2014 Overstock Retail Pre-Tax Income 2015 62% Q4-15 Q1-16 Q2-16 88% 64% -Wayfair Accounts Payable % of Cash $10,092 $(77,348) 2016 2015 107% 68% Q3-16 ■Wayfair Pre-Tax Income 109% Q4-16 $32,332 58% $(193,767) 2016 26#27Quarterly Revenue and Growth ($,000) 600,000 500,000 400,000 300,000 200,000 100,000 398,344 17% Q1-15 loverstock.com® Q2-15 Q3-15 Q4-15 Revenue ($) 413,677 4% Q1-16 Q2-16 Q3-16 Revenue growth (yoy) Q4-16 432,435 5% Q1-17 40% 35% 30% 25% 20% 15% 10% 5% 0% 27#28Quarterly Gross Profit and Growth ($,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) 75,437 18% Q1-15 loverstock.com® HU Q2-15 Q3-15 77,307 Q4-15 Gross profit ($) 2% Q1-16 Q2-16 Q3-16 Gross profit growth (yoy) Q4-16 86,907 12% Q1-17 55% 50% 45% 40% 35% 30% 25% 20% 15% 10% 5% 0% -5% 28#29Quarterly Contribution* and Growth. ($,000) 60,000 50,000 40,000 30,000 20,000 10,000 0 (10,000) 48,169 Q1-15 INI JUI 17% 4% Q2-15 loverstock.com Q3-15 Q4-15 50,020 Contribution ($) Q1-16 Q2-16 Q3-16 Contribution growth (yoy) * Non-GAAP - see discussion and reconciliation in our earnings press release Contribution dollars = Gross profit less Sales & Marketing expense plus Club O Rewards and Gift Card breakage. 49,960 Q4-16 0% Q1-17 60% 50% 40% 30% 20% 10% 0% -10% 29#30Quarterly Gross Margin and Contribution Margin* 25.0% 20.0% 15.0% 10.0% 5.0% 0.0% 18.9% 12.1% Q1-15 Q2-15 Q3-15 Q4-15 Gross margin 18.7% 12.1% Q1-16 Q2-16 Q3-16 Contribution margin Non-GAAP - see discussion and reconciliation in our earnings press release Contribution margin = Gross profit less Sales & Marketing expense plus Club O Rewards and Gift Card breakage as a percentage of revenue. overstock.com Q4-16 20.1% 11.6% Q1-17 30#31Technology and G&A Expenses $s and % of Revenue ($,000) 80,000 70,000 60,000 50,000 40,000 30,000 20,000 10,000 11.0% 43,621 5.8% 5.2% Q1-15 G&A overstock.com Q2-15 Technology Q3-15 Q4-15 11.5% 47,558 6.2% 5.3% Q1-16 G&A and Tech (% of revenue) Q2-16 Q3-16 G&A (% of revenue) Q4-16 11.9% 51,602 6.7% 5.2% Q1-17 12.0% 10.0% 8.0% 6.0% 4.0% 2.0% 0.0% -Technology (% of revenue) 31#32Corporate Employees 1,400 1,200 1,000 800 600 400 200 0 1,002 Q1-15 Q2-15 loverstock.com Q3-15 Corporate employees excludes customer service and warehouse staff. Q4-15 1,143 Q1-16 Non-Tech Q2-16 Tech Q3-16 Q4-16 1,152 Q1-17 32#33Operating and Free Cash Flow (TTM) ($,000) 100,000 80,000 60,000 40,000 20,000 0 (20,000) (40,000) 67,424 25,661 20,988 Q1-15 Q2-15 Q3-15 Q4-15 Cash flow from operations (TTM) * Non-GAAP - see discussion and reconciliation in our earnings press release Free Cash Flow = Cash Flow from Operations less Expenditures for Fixed Assets. loverstock.com * 63,102 47,580 (9,391) Q1-16 Free cash flow* (TTM) Q2-16 Q3-16 Q4-16 50,970 31,022 (13,063) Q1-17 Cash paid for new headquarters construction (TTM) 33#34GAAP TTM Inventory Turns and GMROI 80.0 70.0 60.0 50.0 40.0 30.0 20.0 10.0 0.0 47.6 1095% Q1-15 Q2-15 overstock.com® Q3-15 Q4-15 TTM Inventory turns TTM Inventory Turns = TTM COGS / Average Inventory TTM GMROI = TTM Gross Margin % * TTM Revenue / Average Inventory 55.5 1244% Q1-16 Q2-16 Q3-16 TTM GMROI Q4-16 71.9 1659% Q1-17 2000% 1800% 1600% 1400% 1200% 1000% 800% 600% 400% 200% 0% 34#35Customer Orders and Average Order Size* (#,000) 4,000 3,500 3,000 2,500 2,000 1,500 1,000 500 2,630 $174 Q1-15 Q2-15 overstock.com Q3-15 Q4-15 Customer orders 2,675 $177 Q1-16 Average Order Size is measured at the time of order, before promotional discounts and shipping revenue. Q2-16 Q3-16 Average order size* Q4-16 2,606 $195 Q1-17 $300 $250 $200 $150 $100 $50 $0 35#36Unique Customers and Cost Per Customer (#,000) 3,000 2,500 2,000 1,500 1,000 500 1,901 $14.72 Q1-15 loverstock.com® Q2-15 Q3-15 Unique customers Q4-15 1,894 $16.61 Q1-16 Q2-16 Q3-16 Q4-16 Marketing $ / unique customers (cost per customer) 1,811 $20.78 Q1-17 $40.00 $35.00 $30.00 $25.00 $20.00 $15.00 $10.00 $5.00 36#37MEDICI VENTURES to T ZERO IMM PEERNOVA E A O A bitt OF MEDICI VENTURES ripio SettleMint Q factom IdentityMind GLOBAL Digital Identities You Can Trust#38Overstock.com Ticker Symbols Common Shares - NASDAQ: OSTK Series A Preferred - Medici Ventures' to platform: OSTKP Series B Preferred - OTCQB: OSTBP loverstock.com® 38#39loverstock.com Email all questions to: [email protected] f Follow Us On You Tube 8+ 39