Q1 2021Earnings Call

Forward-Looking Statements

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The information presented herein may contain forward-looking statements within the meaning of the federal securities laws. Such forward-looking statements include all

statements other than statements of historical fact, including forecasts of trends, market conditions, and other factors that will impact our results of operations. You

should not place undue reliance on any forward-looking statements, which speak only as of the date they were made. We undertake no obligation to update any

forward-looking statements as a result of any new information, future developments, or otherwise. Forward-looking statements are inherently difficult to predict.

Accordingly, actual results could differ materially for a variety of reasons, including but not limited to market volatility, the world economy, government regulation, and

our supply chain, including supply and demand for the products and services we offer, and the ability of our third-party partners and carriers to provide products and

services without interruption and at a reasonable cost. Actual results could also differ materially for a number of reasons, including, but not limited to initiatives to

improve or maintain the performance of our business, adverse tax, regulatory or legal developments, competition, and any inability to maintain profitability, continue to

generate positive cash flow from operations, raise capital, or borrow funds on acceptable terms, 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, any inability to protect our intellectual property, and difficulties we may

experience with increasing or maintaining our search engine optimization results, converting web traffic to sales, or ensuring we maintain our new customer base. Other

risks and uncertainties include, among others, whether our partnership with Pelion Venture Partners will be able to achieve its objectives and the timing for doing such.

More information about factors that could potentially affect our financial results are included in our Form 10-K for the year ended December 31, 2020, which was filed

with the SEC on February 26, 2021, and in our subsequent filings with the SEC. The Form 10-K and our subsequent filings with the SEC 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.

Agenda

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1. CEO Remarks

2. Financial Results

3. Business Updates

4. Summary and Q&A

Corporate Update

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▪ Closed blockchain fund transaction with Pelion Venture Partners on April 23

– Announced strategic partnership on January 25 (original goal to close by mid-July)

– Medici Ventures converted into a limited partnership (the “Fund”) overseen by Pelion

– Medici Ventures deconsolidated in financial results

▪ Regulatory front – no updates

▪ Annual shareholder meeting on May 13

▪ Continue to operate well working remote-first

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Financial Results

Q1 2021 Financial Results

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Note: All figures represent results from continuing operations.1 In Q1’20 we recorded $2.5M in special items that benefited G&A expense. Reported G&A expense in Q1’20 was $51.2M, or 15.1% of revenue.2 Adjusted EBITDA is a non-GAAP financial measure. See Reconciliation in Appendix.

$659.9 Million+94% vs. Q1’20

+82% vs. Q1’19

Revenue

23.3%+141bps vs. Q1’20

+342bps vs. Q1’19

Gross Margin

8.1%-771bps vs. Q1’201

-783bps vs. Q1’19

G&A and Tech % of Revenue

$534.8 Million+$39.4M vs. Q4’20

+$438.3M vs. Q4’19

Ending CashAdjusted EBITDA2

$33.9 Million+$40.4M / +618% vs. Q1’20

+$41.7M / +530% vs. Q1’19

Diluted EPS

$0.56+$0.90 vs. Q1’20

+$1.15 vs. Q1’19

Revenue

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$363 $367 $341

$364 $340

$767 $718

$670 $660

(18%)(23%) (22%)

(19%)

(6%)

109% 111%

84%

94%

(40%)

(20%)

0%

20%

40%

60%

80%

100%

120%

$-

$100

$200

$300

$400

$500

$600

$700

$800

Q1 '19 Q2 '19 Q3 '19 Q4 '19 Q1 '20 Q2 '20 Q3 '20 Q4 '20 Q1 '21

Revenue($M)

YoY Revenue∆ Q1 Dynamics

▪ Revenue of $660M

– +94% / $320M vs. Q1’20

– +82% / $297M vs. Q1’19

Note: All figures represent results from continuing operations.

Gross Margin

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$72 $72$68

$75 $74

$178

$169

$151 $15419.9% 19.7% 20.0%

20.7%

21.9%

23.2% 23.5%

22.5%23.3%

0%

5%

10%

15%

20%

25%

$-

$25

$50

$75

$100

$125

$150

$175

$200

$225

Q1 '19 Q2 '19 Q3 '19 Q4 '19 Q1 '20 Q2 '20 Q3 '20 Q4 '20 Q1 '21

Gross Profit($M)

Gross Margin(%) Q1 Dynamics

▪ Gross margin of 23.3%

– +141bps vs. Q1’20

– +342bps vs. Q1’19

▪ Gross margin benefited by:

– Continued sales mix into core home furnishings categories

– Disciplined discounting activities offset by increased acquisition marketing

Note: All figures represent results from continuing operations.

$58

$52

$48

$52$54

$57$59

$54 $53

15.9%

14.1% 14.1% 14.4%15.1%

6.5%

8.2% 8.1% 8.1%

0%

2%

4%

6%

8%

10%

12%

14%

16%

18%

$-

$10

$20

$30

$40

$50

$60

$70

$80

Q1 '19 Q2 '19 Q3 '19 Q4 '19 Q1 '20 Q2 '20 Q3 '20 Q4 '20 Q1 '21

G&A and Tech Expense($M)

G&A and Tech Exp % of Revenue(%)

G&A and Tech Expense

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Q1 Dynamics

▪ G&A and tech expense generating operating leverage

– -1% vs. Q1’201

– -8% vs. Q1’19

▪ G&A and tech expense % of revenue of 8.1%

– -771bps vs. Q1’201

– -783bps vs. Q1’19

7.5%2

Note: All figures represent results from continuing operations.1 In Q1’20 we recorded $2.5M in special items that benefited G&A expense. Reported G&A expense in Q1’20 was $51.2M, or 15.1% of revenue.2 In Q2’20 we recorded $7.3M in special items that benefited G&A expense. Reported G&A expense in Q2’20 was $49.9M, or 6.5% of revenue.

15.8%1

Adjusted EBITDA

Note: All figures represent results from continuing operations.

Retail Adjusted EBITDA is a non-GAAP financial measure. See Reconciliation in Appendix.

Q1 Dynamics

▪ Adj. EBITDA of $34M

– +$40M vs. Q1’20

– +$42M vs. Q1’19

▪ Adj. EBITDA margin of 5.1%

– +706bps vs. Q1’20

– +730bps vs. Q1’19

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$(8)

$(2)$(5)

$(7) $(7)

$49 $46

$30 $34

(2.2%)

(0.7%)

(1.4%)

(1.8%) (1.9%)

6.4% 6.4%

4.5%

5.1%

(4%)

(2%)

0%

2%

4%

6%

8%

$(40)

$(30)

$(20)

$(10)

$-

$10

$20

$30

$40

$50

$60

Q1 '19 Q2 '19 Q3 '19 Q4 '19 Q1 '20 Q2 '20 Q3 '20 Q4 '20 Q1 '21

Adj. EBITDA($M)

Adj. EBITDA Margin(%)

Active Customers and Order Frequency

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Q1 Dynamics

▪ Active customers reached record of 9.9M

– +92% / +4.8M vs. Q1’20

– +60% / +3.7M vs. Q1’19

▪ Order frequency of 1.66

– -2% vs. Q1’20

– -5% vs. Q1’19

– Impacted by influx of new customers

Note: Active customers represents the number of customers who made at least one purchase during the prior twelve-month period.

Note: Orders per active customer represents the number of orders delivered over a twelve-month period divided by the number of active customers for that same period.

6.2 5.8

5.4 5.1 5.2

7.0

8.2

9.2 9.9

1.75 1.76 1.76 1.75 1.70

1.62 1.63 1.64 1.66

-

0.5

1.0

1.5

2.0

-

2

4

6

8

10

12

Q1 '19 Q2 '19 Q3 '19 Q4 '19 Q1 '20 Q2 '20 Q3 '20 Q4 '20 Q1 '21

Active Customers(M)

Orders per Active Customer

Orders and Average Order Value

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Q1 Dynamics

▪ Orders delivered (LTM) reached record of 16.5M

– +88% / +7.7M vs. Q1’20

– +52% / +5.7M vs. Q1’19

▪ Average order value of $183

– +17% vs. Q1’20

– +18% vs. Q1’19

– Driven by continued sales mix into core home furniture categories

Note: LTM orders delivered represents the total number of orders delivered during the prior twelve-month period.

Note: Average order value represents net revenue divided by orders delivered, measured on a quarterly basis.

10.9 10.2

9.6 8.9 8.8

11.3

13.4

15.1

16.5 $155

$166 $167

$155 $156 $160

$173 $168

$183

$-

$20

$40

$60

$80

$100

$120

$140

$160

$180

$200

-

2

4

6

8

10

12

14

16

18

20

Q1 '19 Q2 '19 Q3 '19 Q4 '19 Q1 '20 Q2 '20 Q3 '20 Q4 '20 Q1 '21

Orders Delivered (LTM)(M)

Average Order Value

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Business Updates

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1. Amazon

2. Wayfair

3. Walmart

4.

5. Target

6. Pottery Barn

7. IKEA

8. Bed Bath & Beyond

9. West Elm

10. Restoration Hardware

Top 4 Brand in a Growing Market

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Top U.S. Home Furnishings Online Brands1

(ranked by online revenue)

1 Source: Public, third-party analyses and transactional data based on commonly accepted definition of ‘home furnishings and décor’ category (which includes furniture) and ranked by 2020 direct-to-customer online sales.2 Source: Combined data from eMarketer, NRF, NPD, and Earnest transactional data.

6%7%

8%9%

11%

13%

16%

18%

20%

23%

29%

35%

0%

10%

20%

30%

40%

50%

2010 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 Mar 2021(est.)

Furniture & Home Furnishings U.S. Online Penetration2

Establishing Unique Market Positioning

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IKEA

Dream Homes for All:

The space of ‘Smart Value’

where quality & style costs less

Home Goods Expertise

Department Store Generalist

Style & InspirationValue

Amazon

Walmart

Target

Bed Bath &Beyond

Wayfair West Elm

Pottery BarnRestorationHardware

Source: Based on Overstock Annual Brand Research, 2020. Shown are the top ten U.S. home furnishings online home retailers, as ranked by online revenue.

Playing to Our Strengths

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1 Source: eMarketer–Total U.S. Retail Sales estimates, 2020. 2 Source: Overstock customer segmentation research, 2019.

Note: $325B total market size x 40% customer segments market size = $130B market.

Savvy Shoppers Reluctant Refreshers

▪ Higher propensity to shop at Overstock

▪ Deal-driven and low-hassle

▪ Combined market spend is 40% of total market2

$130B Market1,2

Focused Strategy

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vision

financial goal

dream homes for all making beautiful & comfortable homes accessible by helping customerseasily & confidently find just what they want for less

sustainable, profitable market share growth

target customers savvy shopperprimary segment

values Overstock for helping them feel smart about finding a great dealfrom a compelling selection of stylish & quality home products

secondary segment

reluctant refreshervalues Overstock for helping them easily& confidently find just what they want

2021 initiatives improve product findability grow government market share grow Canada market share improve enterprise platform

enablersOKR-drivenfocus

world-classSEO

data-driven customer relationshipand loyalty building

machine learning andalgorithms innovation

rapid iterationmindset

brand pillars

productfindability

get inspired anywhere,but easily find it at Overstock

smartvalue

quality & style for less

easy delivery+ support

fast, free, & predictable delivery,plus low-hassle returns & support

19Note: Sales reflects GMS (gross merchandise sales), calculated as the amount paid by customers for products (and shipping), measured at the time of order, before coupons and discounts, without reductions for estimated returns.

▪ Customers shifted to mobile

▪ In Q1, mobile:

– Purchases >50% of total sales

– Unique visits +62% YoY

– Sales +105% YoY

– Conversion +10% YoY

▪ Focus on app adoption in 2021

productfindabilityproductfindability

0%

20%

40%

60%

80%

Q1'19 Q2'19 Q3'19 Q4'19 Q1'20 Q2'20 Q3'20 Q4'20 Q1'21

Sales % by Device

Mobile

Desktop

0%

20%

40%

60%

80%

Q1'19 Q2'19 Q3'19 Q4'19 Q1'20 Q2'20 Q3'20 Q4'20 Q1'21

Orders Delivered % by Device

Mobile

Desktop

20Note: Sales Mix is shown as a percentage of 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.

▪ Demand for home furnishings

continues to increase

– Home furnishings were 93% of sales in Q1

– Highest home furnishings mix in history

▪ Opportunity to increase brand

association with “Home”

– 2X higher purchase intent if shopper

comes to OSTK for “Home”

– Emphasizing Dream Homes for All

productfindabilityproductfindability

91%93%

2015 2016 2017 2018 2019 2020 Q1'19 Q1'20 Q1'21

Sales Mix of Home Furnishings

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▪ Assortment and SKU productivity

continue to increase

– Number of SKUs sold +24% YoY

– Units sold per SKU +36% YoY

productfindabilityproductfindability

Note: Chart reflects home furnishings SKUs only.

-

2

4

6

8

10

12

14

-

25,000

50,000

75,000

100,000

125,000

150,000

175,000

200,000

225,000

Q1'19 Q2'19 Q3'19 Q4'19 Q1'20 Q2'20 Q3'20 Q4'20 Q1'21

Assortment Optimization

SKUs Sold

Units Sold per SKU

221 Source: Bizrate point of sale survey, Q1 2021.

▪ Free shipping is a top purchase driver and key component of Smart Value

– Launched free shipping on all items in 2020

– Customer rating of shipping charges expected to remain at current levels

smartvaluesmartvalue

Q1 '20 Q2 '20 Q3 '20 Q4 '20 Q1 '21

Customer Rating of Shipping Charges1

12% favorable to

competitors

23Note: Overstock prices used to compare to competitor prices include site sale discounts before coupons are applied. Comparisons account for 30-35% of all product page views.

Price comparisons taken during last week of respective month reported.

▪ Savvy Shoppers expect value

– Want to feel like they are getting “best quality for the price”

▪ Progress evident in continued refinement of pricing model

▪ Pricing is another key component of Smart Value

smartvaluesmartvalue

55%

70%

80%

85%

Dec '19 Jul '20 Dec '20 Mar '21

Competitively Priced SKUs

24Note: % orders delivered on-time or early and click to delivery refer to small parcels only.

▪ Delivery speed and on-time accuracy

key drivers of customer conversion and

retention

– For customers, maintained focus on

communicating delivery expectations

during times of operational disruption

– For carriers, managed disruptions

through rigorous planning, estimation

accuracy, and communications

easy delivery+ support

1/5/20 2/5/20 3/5/20 4/5/20 5/5/20 6/5/20 7/5/20 8/5/20 9/5/20 10/5/20 11/5/20 12/5/20 1/5/21 2/5/21 3/5/21

% Orders Delivered On-Time or Early

1/5/20 2/5/20 3/5/20 4/5/20 5/5/20 6/5/20 7/5/20 8/5/20 9/5/20 10/5/20 11/5/20 12/5/20 1/5/21 2/5/21 3/5/21

Click to Delivery (business days)

Texas storms

25Note: Following the national stay-at-home order (Q2’20), not all customers were able to reach customer service agents due to unexpected volume of sales.

▪ Contact volume as a percentage of

orders decreased 29% vs. Q1’19

▪ Automation and self-service

capabilities improve customer

retention and reduce costs

– Continue to enhance and augment

self-service functionality

easy delivery+ support

Q1'19 Q2 '19 Q3 '19 Q4 '19 Q1 '20 Q2 '20 Q3 '20 Q4 '20 Q1 '21

Self Service Cases as % of Total

Q1'19 Q2 '19 Q3 '19 Q4 '19 Q1 '20 Q2 '20 Q3 '20 Q4 '20 Q1 '21

CS Contacts as % of Orders

2021 Strategic Initiatives

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Improve onsite search and taxonomy1

2

4

3

Expand into Canada

Establish government business

Improve the enterprise platform

Well Positioned for Market Share Growth – in 2021 and Beyond

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▪ Revenue growth outpacing industry

▪ Gross profit margin in the 22% range

▪ Operating expenses growing slower than revenue,

driving operating leverage

▪ Adjusted EBITDA margins in the mid-single digits

▪ Free cash flow positive

dreamhomesfor all

Driving sustainable, profitable market share growth

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Medici VenturesFund

Summary of Medici Ventures Fund Transaction

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Deal Type Partnership between Overstock and Pelion Venture Partners

General Partner A Pelion Venture Partners entity

Limited Partner Overstock

Partnership Term 8 years

Capital Commitment $45 million (with Overstock option to increase by $30 million)

Fee Structure Annual fees of $2.5 million, combined with success fees paid

according to performance

Timing Announced on January 25; closed on April 23

Deal RationaleMaximize shareholder value through partnering with a highly

experienced venture firm

Medici Ventures Fund Update

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▪ Bitt launched DCash, the world’s first central bank digital currency, on March 31

▪ tZERO:

– Launched strategic capital raise

– Hosting Q1 update call in May

▪ GrainChain selected by SAP for its global startup accelerator program on April 14

▪ Voatz closed first tranche of $10M capital raise on April 20

▪ PeerNova closed first tranche of $25M capital raise on April 22

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Summary and Q&A

Q1 Review and Looking Ahead

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▪ Closed Pelion transaction and deconsolidated Medici Ventures’ businesses

▪ Execute against our 2021 initiatives

▪ Increase Overstock brand association with “Home”

▪ Cement competitive positioning

▪ Improve mobile app adoption

▪ Continue to deliver profitable market share growth

Questions?To ask questions:

▪ Dial-in: (877) 673-5346Conference ID: 5898642

▪ Email: ir@overstock.com

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Appendix

Adjusted EBITDA Reconciliation

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Note: All figures represent results from continuing operations.

1 Special legal charges include amounts associated with the resolution for and adjustments to various legal contingencies and legal fees associated with pursuing our strategic alternatives.

Adjusted EBITDA is a non-GAAP financial measure used in addition to and in conjunction with results presented in accordance with GAAP and should not be relied upon to the exclusion of

GAAP financial measures. Review our financial statements and publicly-filed reports in their entirety and do not rely on any single financial measure.

Mar-2019 Jun-2019 Sep-2019 Dec-2019 Mar-2020 Jun-2020 Sep-2020 Dec-2020 Mar-2021

Income (loss) from continuing operations $ (19,490) $ (13,230) $ (13,448) $ (16,740) $ (13,766) $ 48,174 $ 38,050 $ 23,092 $ 26,018

Depreciation and amortization 5,266 6,127 6,212 6,474 5,569 5,410 5,310 5,487 5,146

Stock-based compensation 3,868 4,560 3,821 3,911 2,681 1,952 1,568 1,640 2,305

Interest (income) expense, net (240) (458) (321) (182) 11 364 264 199 155

Other (income) expense, net 105 419 183 (65) 287 (246) (59) (595) 226

Provision (benefit) for income taxes 864 136 160 (100) 163 505 607 (335) 193

Special items (see table below) 1,757 - (1,221) - (1,486) (7,272) 288 432 (187)

Adjusted EBITDA $ (7,870) $ (2,446) $ (4,614) $ (6,702) $ (6,541) $ 48,887 $ 46,028 $ 29,920 $ 33,856

Special items:

Special legal charges1 $ - $ - $ (1,221) $ - $ (2,501) $ (7,272) $ - $ 432 $ (187)

Severance 1,757 - - - 1,015 - 288 - -

Total Special items $ 1,757 $ - $ (1,221) $ - $ (1,486) $ (7,272) $ 288 $ 432 $ (187)

Three months ended