#1overstock.com® Q1 2018 Earnings Call O#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, 2017 which was filed with the Securities and Exchange Commission on March 15, 2018, and in our subsequent filings with the Securities and Exchange Commission. 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. Ooverstock.com 2#3Agenda 1. tZERO 2. Retail 3. Other Medici Ventures 4. Financial Results 5. Strategic Alternatives 6. Q&A Ooverstock.com O#4to tZERO overstock.com FIX Clients OMSS (Bloomberg, etc.) SpeedRoute SOR / AI Front-end Risk Mgmt. US ATSS / Exchanges Dark Pools Pro Securities ATS U.S. Equity Markets FIX Protocol Security Token Trading Platform Crypto Exchanges Gemini GDAX F Kraken Poloniex Binance Bittrex Bitfinex 4#5to tZERO overstock.com Accelerating tZERO 5#6to tZERO overstock.com Security Token Trading Platform to tZERO BUY BID $19.00 x600 Token TZRO.ST Quantity 100 Limit Price 19.45 ASK $19.50 x9,400 Time In Force Day SELL LAST $19.50 x500 PLACE BUY ORDER Open Orders ORDER ID 1522279173287 Order History ORDER ID 1522281013936 1522280993060 1522280596442 1522280566635 1522280536054 SIDE Buy SIDE Buy Buy Buy Sell Sell See prototype demonstrated at tZERO.com TIF DAY TIF DAY DAY DAY DAY DAY SYMBOL TZRO.ST STATUS Filled Filled Filled Filled Filled PRICE $19.00 SYMBOL AVG $ $17.00 QTY 1,000 TZRO.ST PRICE AVG $ TZRO.ST $20.00 $19.50 500 TZRO.ST $19.50 $19.50 100 TZRO.ST $19.45 $19.45 QTY TZRO.ST $19.45 $19.45 100 $19.45 $19.45 200 100 6#7to tZERO overstock.com Other Updates • Digital Locate Receipts (DLRs) • Security Token Offering (STO) SEC 7#8Oloverstock Retail overstock.com TM FP 8#9Retail Strategy 1. Grow investment in technology platforms (including Al/ML). 2. Selectively increase branding and digital marketing. 3. Add distribution facilities to speed shipping to customer. 4. Accelerate private label strategy 5. Expand Club O rewards program to enhance customer loyalty. overstock.com 9#10Ooverstock.com New customers measured on the date of first order 10 Week Ending -30% 2017-04-09 2017-04-16 2017-04-23 2017-04-30 2017-05-07 2017-05-14 2017-05-21 2017-05-28 2017-06-04 2017-06-11 2017-06-18 2017-06-25 2017-07-02 2017-07-09 2017-07-16 2017-07-23 2017-07-30 2017-08-06 2017-08-13 2017-08-20 2017-08-27 2017-09-03 2017-09-10 2017-09-17 2017-09-24 2017-10-01 2017-10-08 2017-10-15 2017-10-22 2017-10-29 2017-11-05 2017-11-12 2017-11-19 2017-11-26 2017-12-03 2017-12-10 2017-12-17 2017-12-24 2017-12-31 2018-01-07 2018-01-14 2018-01-21 2018-01-28 2018-02-04 2018-02-11 2018-02-18 2018-02-25 2018-03-04 2018-03-11 2018-03-18 2018-03-25 2018-04-01 -20% -10% Easter 30% Weekly New Customer Growth#11Retail Quarterly Revenue and GMV Growth 10% 5% 0% -5% -10% -15% 4.5% 4.5% Q1 '17 Oloverstock.com 3.3% 3.2% Q2 '17 -1.5% -4.0% Q3 '17 Revenue Growth ... GMV Growth -8.5%. -13.3% Q4 '17 5.8% 3.0% Q1 '18 GMV = Gross merchandise volume, calculated as the amount paid by customers for products (and shipping), measured at the time of order, after coupons and discounts, without reductions for estimated returns. 11#12Quarterly Gross Margin of 21.0% 25% 20% 15% 10% 5% 0% 20.0% Q1 '17 Oloverstock.com 19.4% Q2 '17 19.6% Q3 '17 18.7% Q4 '17 21.0% Q1 '18 Gross Margin for Overstock Retail Only 12#13Q1 2018 Results: Retail Revenue $440.0 Million 3% increase vs. Q1 2017 Gross Margin 21.0% vs. 20.0% in Q1 2017 overstock.com $488.7 Million 6% increase vs. Q1 2017 GMV* Contribution Margin** 4.2% vs. 11.5% in Q1 2017 *** = Gross Profit $92.4 Million 8% increase vs. Q1 2017 * GMV Gross merchandise volume, calculated as the amount paid by customers for products (and shipping), measured at the time of order, after coupons and discounts, without reductions for estimated returns. ** Non-GAAP - see discussion and reconciliation in our earnings press release. Excluding intercompany transactions eliminated in consolidation. Pre-Tax Income (Loss)*** ($33.6) Million vs. $1.4 million in Q1 2017 13#14overstock.com MEDICI VENTURES 14#15Medici Ventures Has Ownership Interests in Startup Companies Pursuing Blockchain Applications bitt BITSY ripio to tZERO PEERNOVA SettleMint overstock.com® DESOTO PROPERTY RIGHTS S spera Voatz factom symbiont IdentityMind NEW FinClusive Capital GLOBAL 15#16Q1 Special Items Medici - ($14.5M) Net Impact $11.6M General and Administrative, $2.9M Sales and Marketing Impairment of cryptocurrency holdings ($8.0M) Realized loss on sale of cryptocurrencies ($0.2M) tZERO stock compensation and severance ($6.3M) Retail - $0 Net Impact All General and Administrative • Realized gain on sale of cryptocurrencies $1.8M Impairment of cryptocurrency holdings ($0.8M) Write-off of costs of discontinued equity offering ($1.0M) Oloverstock.com 16#17Q1 2018 Results: OSTK Total Revenue $445.3 Million 3% increase vs. Q1 2017 Pre-Tax Income (Loss) ($54.7) Million ($33.6M) - Retail* ($21.2M) - Medici* vs. ($6.6) million in Q1 2017 $1.4M Retail* ($8.0M) - Medici* overstock.com Gross Profit $93.9 Million 8% increase vs. Q1 2017 Q1 Operating Cash Flow ($10.2) Million vs. ($23.1) million in Q1 2017 * Gross Margin 21.1% vs. 20.1% in Q1 2017 Ending Cash $259.6 Million vs. $203.2 million at Dec. 31, 2017 Excluding intercompany transactions eliminated in consolidation 17#18Strategic Alternatives ● ● Capitalize up from Medici (e.g. tZERO) Recapitalize with Large Capital Partner Who is Willing to Think Big Sell the Retail Business Oloverstock.com 18#19Send questions to [email protected] overstock.com 19