UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of

the Securities Exchange Act of 1934 (Amendment No.    )No.1)

Filed by the Registrant  ☒

Filed by a Party other than the Registrant  ☐

Check the appropriate box:

Overstock.com, Inc.

(Name of Registrant as Specified In Its Charter)

(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check the appropriate box):

799 W. Coliseum Way

Midvale, Utah 84047

Dear Fellow Stockholders:

On July 30, 2019, the Board of Directors of Overstock.com, Inc. (the “Company”) announced a dividend of the Company’s Digital Voting SeriesA-1 Preferred Stock (the “Dividend”). The issuance of the Dividend is of great importance to the Company’s blockchain strategy. We believe the Dividend will demonstrate the benefits and promise of digitally-enhanced securities on a wide scale while utilizing tZERO’s proprietary technology. In particular, we believe the successful issuance of the Dividend will demonstrate to other issuers and market participants that this technology is scalable and has significant benefits to all market participants. We expect the Dividend will incentivize broker-dealers to participate in and connect with the tZERO platform and the alternative trading system operated by tZERO ATS, LLC (“tZERO ATS”). As tZERO ATS increases liquidity, we believe the value of tZERO will grow.

On February 13, 2020, we are holding a special meeting of stockholders of the Company to approve certain amendments to the Company’s certificates of designation for its preferred stock that would facilitate the Dividend. These changes enable the issuance of the Dividend on a 1:10 basis and allow a broader group of stockholders toholdthe Dividend shares on the day of its distribution, as discussed in the accompanying proxy materials. Because the Dividend, as proposed, would be paid to all holders of common stock, Digital Voting Series A-1 Preferred Stock and Voting Series B Preferred Stock on a 1:10 basis, the Dividend, by itself, would not increase or reduce any stockholder’s proportionate ownership interest in Overstock (other than for holders of fractional shares, who will not receive the Dividend).

The Board of Directors is fully supportive of the Dividend and believes that it will help us achieve our business objectives while delivering value to our stockholders. A positive stockholder vote will help ensure that the Dividend, which we believe is the first of its kind, is issued in a manner designed to achieve maximum success. The vote also gives you the opportunity to voice your view on the innovative potential and benefits of blockchain technology. The Board encourages you to support the Dividend and help the Company achieve its strategic goals with blockchain technology.

The attached Notice of Special Meeting and Proxy Statement describe the formal business to be conducted at the Special Meeting. We encourage you to carefully read these materials, as well as any additional materials provided to you in connection with the Special Meeting.Your vote is important to us: even if you do not plan to attend the meeting in person, we hope your votes will be represented.

Sincerely,

Midvale, Utah [                    ], 2019

799 W. Coliseum Way

Midvale, Utah 84047

Notice of AnnualSpecial Meeting of Stockholders

To Be Held at 1:00 p.m. on May 9, 2019February 13, 2020

Dear Fellow Stockholders:

We cordially invite you to attend the 2019 AnnualNotice is hereby given that a Special Meeting (the “Special Meeting”) of Stockholders of Overstock.com, Inc. (the “Company”). The meeting will be held at the offices of the Company, located at 799 W. Coliseum Way, Midvale, Utah, at 1:00 p.m. Mountain Time on May 9, 2019. If you plan to attend the meeting, please let us know by checking the “Meeting Attendance” box on your proxy card or by notifying our investor relations department by email atir@overstock.com no later than 11:59 Eastern Time on May 8, 2019.

February 13, 2020. At the meeting,Special Meeting, holders of our common stock, par value $0.0001 per share (the “Common Stock”), our BlockchainDigital Voting Series AA-1 Preferred Stock, par value $0.0001 per share (the “SeriesA-1 Preferred Stock”), and our Voting Series B Preferred Stock, (collectively, ourpar value $0.0001 per share (the “Series B Preferred Stock” and, together with the Common Stock and SeriesA-1 Preferred Stock, the “Voting Shares”) will vote on the following matters:

Stockholders will also considerThe Board of Directors has unanimously approved the proposals and act upon any other matter properly coming beforerecommends that our stockholders vote “FOR” the Annual Meeting.SeriesA-1 Preferred Proposal, “FOR” the Series B Preferred Proposal, and, if necessary, “FOR” the Alternative SeriesA-1 Preferred Proposal.

Following the meeting, we will discuss our business and answer appropriate questions.

HoldersThe Board of record of shares of our Voting Shares atDirectors has fixed the close of business on March 12,December 18, 2019 as the record date for the Special Meeting. Only holders of the Voting Shares of record at that time are entitled to notice of, and to vote at, the meeting andSpecial Meeting or at any postponements or adjournments.adjournments thereof. To ensure that your vote is recorded promptly,shares are voted,please votesubmit a proxy as soon as possible,even if you plan to attend the meetingSpecial Meeting in person. We encourage you to votesubmit proxies via the Internet or by telephone. If you received a printed set of proxy materials, youYou also have the option of votingsubmitting a proxy by completing, signing, dating and returning the enclosed proxy card that accompanied the printed materials.card. Submitting your voteproxy via the Internet or by telephone or proxy card will not affect your right to vote in person if you decide to attend the annual meeting.Special Meeting.

More information regarding voting rights and the matters to some of our stockholders a notice of Internet availability of proxy materials instead of a paper copy of this proxy statement and our Annual Report onForm 10-K forbe voted upon is presented in the year ended December 31, 2018 (the “2018Form 10-K”). The notice contains instructions on how to access those documents via the Internet. The notice also contains instructions on how to request a paper copy of our proxy materials, including this proxy statement, our 2018Form 10-K and a form of proxy card or voting instruction card, as applicable. Stockholders who do not receive a notice of Internet availability of proxy materials will receive a paper copy of the proxy materials by mail. We anticipate that this process will minimize the costs of printing and distributing ouraccompanying proxy materials.

Midvale, Utah

March 18, [                    ], 2019

Important Notice Regarding the Availability of Proxy Materials for the

AnnualSpecial Meeting of Stockholders to be held on May 9, 2019February 13, 2020

The Notice of Annual Meeting, Proxy Statement and Annual Report onForm 10-K for the fiscal year

ended December 31, 2018 areis available at [http://www.overstock.com/proxy].

Whether or not you plan to attend the meeting, please votesubmit a proxy via the Internet or by phone or by

completing, signing, dating and returning the accompanying Proxy Cardproxy card in the enclosed self-addressed,

stamped envelope.

Table of Contents

				2019 Special Meeting Proxy Statement | i

Introduction

This Proxy Statement is furnished to the stockholders of Overstock.com, Inc. (“Overstock,” the “Company,” “we” or “our”) in connection with the solicitation of proxies by the Board of Directors (the “Board”) to be voted on at the Special Meeting of Stockholders and at any adjournments or postponements thereof (the “Special Meeting”). Voting materials, which include this Proxy Statement and the proxy card, are first being sent or given to stockholders on or about [                    ], 2019.

Stockholders who owned shares of our common stock, par value $0.0001 per share (the “Common Stock”), our Digital Voting SeriesA-1 Preferred Stock, par value $0.0001 per share (the “SeriesA-1 Preferred Stock”), or our Voting Series B Preferred Stock, par value $0.0001 per share (the “Series B Preferred Stock” and, together with the Common Stock and SeriesA-1 Preferred Stock, the “Voting Shares”), at the close of business on the record date are entitled to attend and vote at the Special Meeting.

The purpose of the Special Meeting is to reallocate our preferred stock so that the Dividend (as defined below) can be paid on a 1:10 basis, amend the voting rights of both the Series A-1 Preferred Stock and the Series B Preferred Stock,

remove transfer restrictions so that the SeriesA-1 Preferred Stock can be held by a wide group of investors, and make certain other changes to the SeriesA-1 Preferred Stock that we and the Board believe would be beneficial to stockholders.

Special Meeting Information

Date and Time: 1:00 p.m. Mountain Time on February 13, 2020

Place: Offices of Overstock, located at 799 W. Coliseum Way, Midvale, Utah

Record Date: December 18, 2019

				Special Meeting Proxy Statement | 1

Introduction / Matters to Be Voted on at the Special Meeting

Matters to Be Voted on at the Special Meeting

2 | Special Meeting Proxy Statement

Introduction /  Background to the Special Meeting of Stockholders

Background to the Special Meeting of Stockholders

Overstock Announces Dividend

On July 30, 2019, Overstock announced that the Board had declared a dividend (the “Dividend”) payable in shares of SeriesA-1 Preferred Stock to holders of record of Common Stock, SeriesA-1 Preferred Stock and Series B Preferred Stock. The Dividend would have been payable at a ratio of 1:10, meaning that one share of SeriesA-1 Preferred Stock would be issued for every ten shares of Common Stock, ten shares of SeriesA-1 Preferred Stock or ten shares of Series B Preferred Stock held by holders of such shares as of the record date.

Purpose of the Dividend

The purpose of the Dividend is to allow all Overstock stockholders to receive and experience (and all market participants to see) the benefits and possibilities of enhancements the blockchain can bring to the conventional uncertificated, book-entry securities market, while preserving the current regulatory regime for that market (just as NASDAQ was the first electronic market without a physical trading floor). The blockchain provides enhanced transparency to the conventional records, allowing investors, broker-dealers and regulators to see a courtesy copy of the records of the transfer agent (which control in all cases) on the publicly available distributed ledger available for convenience.

Overstock Announces Registration of Dividend

The record date and the distribution date for the Dividend were initially set for September 23, 2019 and November 15, 2019, respectively. In view of the feedback the Company received from industry participants, investors and regulators with respect to the Dividend, and in order to provide greater liquidity, on September 18, 2019, Overstock announced that it intended to register the shares of SeriesA-1 Preferred Stock with the Securities and Exchange Commission (“SEC”) to be issued in connection with the Dividend. Upon distribution, the Dividend shares of the Series A-1 Preferred Stock will be freely tradable by non-affiliates. As a result, the Company postponed the previously announced record date and distribution date. On September 24, 2019, the Company filed a registration statement with the SEC on FormS-3 to register the SeriesA-1 Preferred Stock.

Overstock Announces Intention to Seek Stockholder Approval

On October 28, 2019, Overstock announced that it would seek stockholder approval to amend certain provisions of the Company’s certificates of designation to facilitate the issuance of the Dividend by eliminating restrictions on the SeriesA-1 Preferred Stock so the Dividend can be held by a wide group of investors and by reallocating the authorized SeriesA-1 Preferred Stock and Series B Preferred Stock to have sufficient authorized, but unissued, shares of SeriesA-1 Preferred Stock to pay the Dividend on a 1:10 basis.

Next Steps for Dividend Following Special Meeting

If the SeriesA-1 Preferred Proposal is approved, Overstock intends to promptly announce the record and distribution dates for the Dividend. As illustrated in the table below, under the heading “Alternatives and Outcomes Based on Stockholder Vote,” in the event that the SeriesA-1 Preferred Proposal is not approved but the Alternative SeriesA-1 Preferred Proposal is approved, Overstock will not be able to pay the Dividend on a 1:10 basis, and the Board currently anticipates declaring a dividend of the SeriesA-1 Preferred Stock on a 1:20 basis. If the Series B Preferred Proposal is adopted, but neither the SeriesA-1 Preferred Proposal nor the Alternative SeriesA-1 Preferred Proposal is adopted, or if all three Proposals fail Overstock will not be able to issue the Dividend. The Board will need to consider whether these votes represent a rejection of the desirability of the Dividend and may consider available alternative structures to achieve the objectives of the Dividend. These alternative structures would depend on feedback from stockholders and other stakeholders but could include, for example, if there are enough shares of authorized and unissued Preferred Stock undesignated as to series, the issuance of a new series of Preferred Stock as a dividend or

				Special Meeting Proxy Statement | 3

Introduction / Preferred Stock Outstanding and Required for Anticipated Board Actions

the use of depositary shares, with each depositary share representing a fraction of a share of a new series of Preferred Stock. For more information on the proposals to be voted on (the SeriesA-1 Preferred Proposal, the Series B Preferred Proposal and the Alternative SeriesA-1 Preferred Proposal collectively referred to as the “Proposals”), see “Proposals to Be Voted On.”

Preferred Stock Outstanding and Required for Anticipated Board Actions

Overstock currently has a total of 5,000,000 shares of preferred stock, par value $0.0001 per share (the “Preferred Stock”), authorized, with 1,000,000 shares of Preferred Stock authorized for the SeriesA-1 Preferred Stock and 2,000,000 shares of Preferred Stock authorized for the Series B Preferred Stock.

The number of authorized shares Overstock currently has, and that we propose to reallocate in order to pay the Dividend on a 1:10 basis, is illustrated in the table below:

Alternatives and Outcomes Based on Stockholder Vote

The Board’s actions following the Special Meeting are dependent on the outcome of the vote on each Proposal. This is, in part, because each Proposal would have an impact on the authorized shares of SeriesA-1 Preferred Stock and Series B Preferred Stock. The Board’s actions will be dependent on the amount of authorized, but unissued, Preferred Stock available.

4 | Special Meeting Proxy Statement

Introduction / Alternatives and Outcomes Based on Stockholder Vote

These alternatives and the anticipated actions of the Board are illustrated in the table below:

As of December 18, 2019, there were [            ] shares of Common Stock outstanding, [            ] shares of SeriesA-1 Preferred Stock outstanding, and [            ] shares of Series B Preferred Stock outstanding.

For more information about the Special Meeting, see “Questions and Answers about the Special Meeting and Procedural Matters.”

				Special Meeting Proxy Statement | 5

Proposals to Be Voted On:

Proposal 1: SeriesA-1 Preferred Proposal

General

The Board adopted resolutions declaring it advisable to amend the SeriesA-1 Certificate of Designation as set forth below and directing that the proposed action be submitted for consideration by Overstock’s stockholders at a special meeting of stockholders. The description in this Proxy Statement of the proposed amendment of the SeriesA-1 Certificate of Designation is qualified in its entirety by reference to, and should be read in conjunction with, the affected text of the amendment as set forth inAppendix A to this Proxy Statement. The SeriesA-1 Certificate of Designation is proposed to be amended to:

Purpose and Effect of the SeriesA-1 Preferred Proposal

The current SeriesA-1 Certificate of Designation has several restrictions that the SeriesA-1 Preferred Proposal would eliminate in order to facilitate the payment of the Dividend and make other changes to provide the Board the ability to facilitate trading of the SeriesA-1 Preferred Stock.

Increase the Number of Authorized Shares of SeriesA-1 Preferred Stock

First, the SeriesA-1 Preferred Proposal seeks to increase the number of authorized shares of SeriesA-1 Preferred Stock so that there would be a sufficient number of authorized, but unissued, shares of SeriesA-1 Preferred Stock to pay the Dividend on a 1:10 basis as originally proposed. On July 26, 2019, Overstock filed an Amended and Restated SeriesA-1 Certificate of Designation (the “July SeriesA-1 Amendment”) with the Secretary of State of Delaware to increase the number of authorized shares of SeriesA-1 Preferred Stock from 1,000,000 to 4,630,000. However, the SeriesA-1 Certificate of Designation had two conflicting provisions with respect to increasing the authorized number of shares of SeriesA-1 Preferred Stock. As described in more detail below, one provision permitted the Board to unilaterally increase the number of authorized shares of SeriesA-1 Preferred Stock while the other provision required a vote of the holders of the SeriesA-1 Preferred Stock to increase the authorized number of shares of SeriesA-1 Preferred Stock. As a result of this conflict, the July SeriesA-1 Amendment was not properly authorized. A certificate of correction voiding the July SeriesA-1 Amendment was filed with the Secretary of State on [                    ], 2019, and, therefore, Overstock currently only has 1,000,000 authorized shares of SeriesA-1 Preferred Stock, which is insufficient to pay the Dividend on a 1:10 basis. Based on the number of shares of Common Stock, SeriesA-1 Preferred Stock and Series B Preferred Stock outstanding as of December 18, 2019, [                ] shares of authorized SeriesA-1

6 | Special Meeting Proxy Statement

Proposal 1

Preferred Stock would be necessary to distribute the Dividend on a 1:10 basis. The SeriesA-1 Preferred Proposal would increase the number of authorized shares of SeriesA-1 Preferred Stock to 4,630,000, as was originally contemplated in the July SeriesA-1 Amendment.

Increasing the number of authorized shares of SeriesA-1 Preferred Stock to 4,630,000 would provide sufficient authorized shares to pay the Dividend on a 1:10 basis. In order to permit this increase, however, the authorized number of shares of Series B Preferred Stock must be reduced to 370,000. As described in more detail below under “—Proposal 2: Series B Preferred Proposal,” the amendment to the Series B Certificate of Designation approved by the Board to reduce the authorized shares of Series B Preferred Stock from 2,000,000 to 370,000 suffered from a similar conflict with respect to the proper authorization to effect a decrease in the number of Series B Preferred Stock as existed with respect to the increase of the authorized number of SeriesA-1 Preferred Stock. As a result, the SeriesA-1 Preferred Proposal to increase the SeriesA-1 Preferred Stock to 4,630,000 can only be adopted if the Series B Preferred Stock is reduced to 370,000. As a result, the approval of the SeriesA-1 Preferred Proposal is conditioned on the approval of the Series B Preferred Proposal.

Eliminate the Class Vote Requirement in Section 9 to Remove Conflict in SeriesA-1 Certificate of Designation

Second, the SeriesA-1 Preferred Proposal seeks to remove the conflict in the SeriesA-1 Certificate of Designation regarding the ability of the Board to unilaterally increase or decrease the number of authorized shares of the SeriesA-1 Preferred Stock referenced above. Section 2 of the SeriesA-1 Certificate of Designation currently provides that the Board may increase the number of authorized shares of SeriesA-1 Preferred Stock (but not in excess of the total number of authorized shares of Preferred Stock that are undesignated as to series) or decrease the number of authorized shares of SeriesA-1 Preferred Stock (but not below the number of shares of SeriesA-1 Preferred Stock outstanding). Section 9 of the SeriesA-1 Certificate of Designation currently provides that holders of SeriesA-1 Preferred Stock must vote as a class upon any amendment increasing or decreasing the aggregate number of authorized shares of SeriesA-1 Preferred Stock. The SeriesA-1 Preferred Proposal eliminates the stockholder vote requirement in Section 9 of the SeriesA-1 Certificate of Designation, permitting the Board to unilaterally authorize any such increases or decreases in the number of authorized shares, subject to the limitations set forth in Section 2 of the SeriesA-1 Certificate of Designation. As a result, adoption of the Series A-1 Preferred Proposal will result in a loss of this stockholder voting right.

Amend Uncertificated Share Requirement in Section 11

Third, the SeriesA-1 Preferred Proposal seeks to amend Section 11, which requires that the shares of SeriesA-1 Preferred Stock be in uncertificated form. In order for the SeriesA-1 Preferred Stock to be eligible for deposit with The Depository Trust Company (“DTC”), under DTC’s rules, the Company may be required to deliver a physical certificate representing the shares. Accordingly, the SeriesA-1 Preferred Proposal would amend Section 11 to authorize the Board to approve the issuance of physical certificates if requested by DTC.

Amend Transfer Restrictions in Section 12

Fourth, the SeriesA-1 Preferred Proposal seeks to remove restrictions on the ownership and transfer of the SeriesA-1 Preferred Stock in order to facilitate the Dividend.

Section 12(b) of the SeriesA-1 Certificate of Designation requires that all “transfers” of SeriesA-1 Preferred Stock be made through an alternative trading system operated by tZERO ATS, LLC, our majority owned subsidiary and a

				Special Meeting Proxy Statement | 7

Proposal 1

broker-dealer registered with the SEC and a member of the Financial Industry Regulatory Authority (“FINRA”) and Securities Investor Protection Corporation (“SIPC”). Because tZERO ATS, LLC only operates one alternative trading system (“ATS,” and such ATS, the “tZERO ATS”), under the current SeriesA-1 Certificate of Designation all “transfers” of the SeriesA-1 Preferred Stock must be made through tZERO ATS. The SeriesA-1 Preferred Proposal amends Section 12(b) in several important respects.

For more information on the SeriesA-1 Preferred Stock, see “Description of the SeriesA-1 Preferred Stock.”

Outcome of Series B Preferred Proposal and Alternative SeriesA-1 Preferred Proposal on SeriesA-1 Preferred Proposal

The adoption of the SeriesA-1 Preferred Proposal is conditioned on the adoption of the Series B Preferred Proposal. If the SeriesA-1 Preferred Proposal is not approved, the Alternative SeriesA-1 Preferred Proposal will be considered at the Special Meeting.

If Overstock’s stockholders adopt the SeriesA-1 Preferred Proposal, the changes set forth in the SeriesA-1 Preferred Proposal will become effective on the filing of either a Certificate of Amendment to the SeriesA-1 Certificate of Designation or an Amended and Restated SeriesA-1 Certificate of Designation incorporating the amendments set forth in the SeriesA-1 Preferred Proposal with the Secretary of State of the State of Delaware.

Vote Required

The adoption of the SeriesA-1 Preferred Proposal requires:

Recommendation of the Board of Directors

The Board unanimously recommends a vote “FOR” the SeriesA-1 Preferred Proposal.

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Proposal 2: Series B Preferred Proposal

General

The Board adopted resolutions declaring it advisable to amend the Series B Certificate of Designation as set forth below and directing that the proposed action be submitted for consideration by Overstock’s stockholders at a special meeting of stockholders. The description in this Proxy Statement of the proposed amendment of the Series B Certificate of Designation is qualified in its entirety by reference to, and should be read in conjunction with, the affected text of the amendment as set forth inAppendix B to this Proxy Statement. The Series B Certificate of Designation is proposed to be amended to:

If Overstock’s stockholders adopt the Series B Preferred Proposal, the changes set forth in the Series B Preferred Proposal will become effective on the filing of either a Certificate of Amendment to the Series B Certificate of Designation or of an Amended and Restated Series B Certificate of Designation incorporating the amendments set forth in the Series B Preferred Proposal with the Secretary of State of the State of Delaware.

Purpose and Effect of the Series B Preferred Proposal

The current Series B Certificate of Designation must be modified in order to permit the adoption of the SeriesA-1 Preferred Proposal.

Decrease the Number of Authorized Shares of Series B Preferred Stock

First, the Series B Preferred Proposal seeks to decrease the number of authorized shares of Series B Preferred Stock to 370,000 in order to permit the increase in the number of authorized shares of SeriesA-1 Preferred Stock contemplated in the SeriesA-1 Preferred Proposal to 4,630,000. Overstock has 5,000,000 total authorized shares of Preferred Stock, 1,000,000 of which are currently designated as SeriesA-1 Preferred Stock and 2,000,000 of which are currently designated as Series B Preferred Stock. In order to increase the total number of authorized shares of SeriesA-1 Preferred Stock to 4,630,000 pursuant to the SeriesA-1 Preferred Proposal, the number of authorized shares of Series B Preferred Stock must be decreased to 370,000. Because the Series B Preferred Proposal is necessary in order to effect the SeriesA-1 Preferred Proposal, the adoption of the SeriesA-1 Preferred Proposal is conditioned on the adoption of the Series B Preferred Proposal. For more information on the SeriesA-1 Preferred Proposal, see “—Proposal 1: SeriesA-1 Preferred Proposal” above.

On July 26, 2019, Overstock filed an Amended and Restated Series B Certificate of Designation (the “July Series B Amendment”) with the Secretary of State of the State of Delaware to decrease the number of authorized shares of Series B Preferred Stock from 2,000,000 to 370,000. However, the Series B Certificate of Designation has the same conflict with respect to increasing or decreasing the authorized number of shares of Series B Preferred Stock as the SeriesA-1 Certificate of Designation. While Section 2 of the Series B Certificate of Designation provides that the Board may unilaterally increase or decrease the authorized shares of Series B Preferred Stock, Section 8 of the Series B Certificate of Designation requires a class vote of holders of the Series B Preferred Stock to increase or decrease the number of authorized shares of Series B Preferred Stock. As a result of this conflict, the July Series B Amendment was not properly authorized. A certificate of correction voiding the July Series B Amendment was filed with the Secretary of State on [                    ] 2019, and, therefore, Overstock currently has 2,000,000 authorized shares of Series B Preferred Stock. The Series B Preferred Proposal would decrease the number of authorized shares of Series B Preferred Stock to 370,000, as was originally contemplated in the July Series B Amendment.

				Special Meeting Proxy Statement | 9

Proposal 2

Eliminate the Class Vote Requirement in Section 8 to Remove Conflict in Series B Certificate of Designation

Second, the Series B Preferred Proposal removes the conflict in the Series B Certificate of Designation regarding the ability of the Board to unilaterally increase or decrease the number of authorized shares of the Series B Preferred Stock referenced above. Section 2 of the Series B Certificate of Designation currently provides that the Board may increase the number of authorized shares of Series B Preferred Stock (but not in excess of the total number of authorized shares of Preferred Stock that are undesignated as to series) or decrease the number of authorized shares of Series B Preferred Stock (but not below the number of shares of Series B Preferred Stock outstanding). Section 8 of the Series B Certificate of Designation provides that holders of Series B Preferred Stock must vote as a class upon any amendment increasing or decreasing the aggregate number of authorized shares of Series B Preferred Stock. The Series B Preferred Proposal eliminates the stockholder vote requirement in Section 8 of the Series B Certificate of Designation for increasing or decreasing the number of authorized shares of Series B Preferred Stock, thereby permitting the Board to unilaterally make these increases or decreases in the number of authorized shares, subject to the limitations set forth in Section 2 of the Series B Certificate of Designation. As a result, adoption of the Series B Preferred Proposal will result in a loss of this stockholder voting right.

Outcome of SeriesA-1 Preferred Proposal and Alternative SeriesA-1 Preferred Proposal on Series B Preferred Proposal

In the event that the Overstock stockholders adopt the Series B Preferred Proposal but do not adopt the SeriesA-1 Preferred Proposal or the Alternative SeriesA-1 Preferred Proposal, Overstock anticipates that it will still file a Certificate of Amendment or an Amended and Restated Series B Certificate of Designation with the Secretary of State of the State of Delaware implementing the Series B Preferred Proposal. The Board would need to evaluate whether this combination of votes by our stockholders represents a rejection of the desirability of a dividend of shares of the SeriesA-1 Preferred Stock and may, depending on stockholder and stakeholder feedback, consider available alternative structures to achieve the objectives of the Dividend. These alternative structures could include, for example, if there is a sufficient number of authorized shares of Preferred Stock undesignated as to series, the issuance of a new series of Preferred Stock as a dividend or the use of depositary shares, with each depositary share representing a fraction of a share of a new series of Preferred Stock.

When the amendments to the Series B Certificate of Designation would become effective:

Vote Required

The adoption of the Series B Preferred Proposal requires:

Recommendation of the Board of Directors

The Board unanimously recommends that the stockholders vote “FOR” the Series B Preferred Proposal.

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Proposal 3: Alternative SeriesA-1 Preferred Proposal

General

The Board adopted resolutions declaring that in the event the SeriesA-1 Preferred Proposal cannot be adopted (either because it does not receive the requisite stockholder votes or because the Series B Preferred Proposal upon which it is conditioned is not adopted) it is advisable to amend the SeriesA-1 Certificate of Designation as set forth below and directing that the proposed action be submitted for consideration by Overstock’s stockholders at a special meeting of stockholders. The description in this Proxy Statement of the proposed amendment of the SeriesA-1 Certificate of Designation is qualified in its entirety by reference to, and should be read in conjunction with, the affected text of the amendment as set forth inAppendix C to this Proxy Statement. The SeriesA-1 Certificate of Designation is proposed to be amended to:

Purpose and Effect of the Alternative SeriesA-1 Preferred Proposal

In the event that the SeriesA-1 Preferred Proposal is not adopted, the Alternative SeriesA-1 Preferred Proposal would result in identical changes to the SeriesA-1 Certificate of Designation as the SeriesA-1 Preferred Proposal except that the number of authorized shares of SeriesA-1 Preferred Stock would only be increased to 3,000,000 instead of 4,630,000, whether or not the Series B Preferred Proposal is adopted. As a result, if the Alternative SeriesA-1 Preferred Proposal is adopted, there will not be sufficient authorized shares of SeriesA-1 Preferred Stock in order to pay the Dividend on a 1:10 basis. If the Alternative SeriesA-1 Preferred Proposal is adopted, whether or not the Series B Preferred Proposal is adopted, the Board currently intends to declare a dividend of shares of SeriesA-1 Preferred Stock on a 1:20 basis. For more information on the Dividend and the SeriesA-1 Preferred Stock, see “Introduction—Background to the Special Meeting of Stockholders” and “Description of the SeriesA-1 Preferred Stock.”

The purpose and effect of the amendments to Sections 9, 11 and 12 of the SeriesA-1 Certificate of Designation are the same as the purpose and effect of the SeriesA-1 Preferred Proposal, see “—Proposal 1: SeriesA-1 Preferred Proposal—Purpose and Effect of the SeriesA-1 Preferred Proposal.” Adoption of the AlternativeSeries A-1 Preferred Proposal will result in a loss of stockholder voting rights with respect to the increase or decrease of authorized shares of Series A-1 Preferred Stock.

Outcome of SeriesA-1 Preferred Proposal and Series B Preferred Proposal on Alternative SeriesA-1 Preferred Proposal

The Alternative SeriesA-1 Preferred Proposal will only be brought for a vote at the Special Meeting in the event that the SeriesA-1 Preferred Proposal cannot be effected, either because it does not receive the requisite stockholder votes or because the Series B Preferred Proposal is not adopted. If the SeriesA-1 Preferred Proposal is not adopted, the Alternative SeriesA-1 Preferred Proposal will be brought for a vote whether or not the Series B Preferred Proposal is adopted.

In the event that the Alternative SeriesA-1 Preferred Proposal and the Series B Preferred Proposal are both adopted, there will be 3,000,000 authorized shares of SeriesA-1 Preferred Stock, 370,000 authorized shares of Series B Preferred Stock and 1,630,000 authorized but undesignated as to series of Preferred Stock. In the event the Alternative SeriesA-1 Preferred Proposal is adopted but the Series B Preferred Proposal is not adopted, there will be 3,000,000 authorized shares of SeriesA-1 Preferred Stock and 2,000,000 authorized shares of Series B Preferred Stock. In either case, the Board would anticipate declaring a dividend of shares of SeriesA-1 Preferred Stock on a 1:20 basis.

If Overstock’s stockholders adopt the Alternative SeriesA-1 Preferred Proposal, the changes set forth in the Alternative SeriesA-1 Preferred Proposal will become effective on the filing of either a Certificate of Amendment to the

				Special Meeting Proxy Statement | 11

Proposal 3

SeriesA-1 Certificate of Designation or an Amended and Restated SeriesA-1 Certificate of Designation incorporating the amendments set forth in the Alternative SeriesA-1 Preferred Proposal with the Secretary of State of the State of Delaware.

Vote Required

The adoption of the Alternative SeriesA-1 Preferred Proposal requires:

Recommendation of the Board of Directors

If voting on the Alternative SeriesA-1 Preferred Proposal is necessary, the Board unanimously recommends that the stockholders vote “FOR” the Alternative SeriesA-1 Preferred Proposal.

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No Appraisal Rights

Under the General Corporation Law of the State of Delaware, our stockholders are not entitled to appraisal rights in connection with any of the Proposals contained in this Proxy Statement.

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Description of the SeriesA-1 Preferred Stock

The following description is a summary of the material terms of our SeriesA-1 Preferred Stock as currently in effect. This summary is subject to, and qualified in its entirety by, the rights, preferences, powers and privileges of the SeriesA-1 Preferred Stock, set forth in the SeriesA-1 Certificate of Designation, which was filed with the SEC as an exhibit to a Current Report on Form8-K on June 27, 2019. See also “Risk Factors” and the other information in this Proxy Statement.

Our Authorized SeriesA-1 Preferred Stock

Under our amended and restated certificate of incorporation, our Board is authorized, without further stockholder action, to issue up to 5,000,000 shares of Preferred Stock, par value $0.0001 per share, in one or more series, with such powers, designations, privileges, preferences and relative, participating, optional and other rights and such qualifications, limitations and restrictions thereof as shall be set forth in the resolutions providing therefor. As of the date hereof, and giving effect to the previously filed certificate of correction filed on [                    ], 2019, 3,000,000 shares of Preferred Stock have been so designated, with 1,000,000 shares having been designated asSeries A-1 Preferred Stock and 2,000,000 shares having been designated as Series B Preferred Stock.

The SeriesA-1 Preferred Stock is fully paid and nonassessable. Holders of SeriesA-1 Preferred Stock have no preemptive or preferential or other rights to purchase or subscribe for any of the Company’s stock, obligations, warrants or other securities.

Rank

Shares of the SeriesA-1 Preferred Stock rank equally with the Series B Preferred Stock, senior to our Common Stock with respect to dividends and equal to our Common Stock with respect to the distribution of our assets upon the liquidation, dissolution and winding up of the Company. In addition, the SeriesA-1 Preferred Stock and the Series B Preferred Stock, with respect to rights upon our liquidation, winding up or dissolution, are structurally subordinated to existing and future indebtedness of our subsidiaries as well as the capital stock of our subsidiaries held by third parties.

As of September 30, 2019, we had liabilities of approximately $231 million, and we may incur significant additional debt in the future. See our Quarterly Report onForm 10-Q for the period ended September 30, 2019, which is incorporated into the Proxy Statement by reference. See “Risk Factors—Risks Relating to the SeriesA-1 Preferred Stock—The SeriesA-1 Preferred Stock and the Series B Preferred Stock will rank junior to all of our and our subsidiaries’ liabilities in the event of a bankruptcy, liquidation or winding up of our or our subsidiaries’ business.”

Dividends

Holders of SeriesA-1 Preferred Stockare entitled to an annual cash dividend equal to $0.16 per share, in preference to any dividend payment to the holders of our Common Stock, out of funds of the Company legally available for payment of dividends and subject to declaration by our Board. However, there is no assurance of any payment of any dividends on the SeriesA-1 Preferred Stock. We have no obligation to pay any dividends to the holders of SeriesA-1 Preferred Stockunless (and only to the extent that) our Board approves and declares dividend payments to the holders of SeriesA-1 Preferred Stockor we pay a dividend to the holders of our Common Stock. Dividends on the SeriesA-1 Preferred Stockare cumulative. If declared, dividends are paid to holders of record on a date selected by our Board in its sole discretion. Dividends not paid accumulate annually on December 15 of each year beginning with December 15, 2019, whether or not the Company has earnings or profits, whether or not there are funds legally available for the payment of dividends and whether or not dividends are declared on the SeriesA-1 Preferred Stock, and are entitled to be paid prior to any dividend to the holders of our Common Stock. Dividends on the SeriesA-1 Preferred Stockand the Series B Preferred Stockare paid equally with one another.

In addition to its preferential dividend rights, the SeriesA-1 Preferred Stock is also entitled to participate in any dividend paid to the holders of our Common Stock, subject to the limitations set forth in the SeriesA-1 Certificate of

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Description of the SeriesA-1 Preferred Stock

Designation. If the record date for any dividend to the holders of our Common Stock occurs while shares of SeriesA-1 Preferred Stockare outstanding, the holders of SeriesA-1 Preferred Stock outstanding on the record date are entitled to the same amount per share of SeriesA-1 Preferred Stockas is paid per share of Common Stock. For further information on potential restrictions on our payment of dividends, see “Risk Factors—Risks Relating to the SeriesA-1 Preferred Stock—Our obligation to pay dividends on the SeriesA-1 Preferred Stock is limited, and our ability to pay dividends on the SeriesA-1 Preferred Stock may be limited.”

Redemption

The SeriesA-1 Preferred Stockis not subject to redemption at our option.

No Conversion or Exchange Rights; Potential Conversion of SeriesA-1 Preferred

Holders of the SeriesA-1 Preferred Stockdo not have any right to convert their shares into any other security or to exchange their shares for any other security, including our Common Stock. However, the SeriesA-1 Certificate of Designation grants us the right to cause the conversion of the outstanding shares of SeriesA-1 Preferred Stock into shares of Series B Preferred Stock at any time. In any such conversion, each outstanding share of SeriesA-1 Preferred Stock would be converted into one share of Series B Preferred Stock. If there is a dividend arrearage on the SeriesA-1 Preferred Stock and there is not an equal per share dividend arrearage on the Series B Preferred Stock, we will make such dividend payment on the SeriesA-1 Preferred Stock or on the Series B Preferred Stockas may be necessary in order to equalize such per share difference in such dividend arrearages prior to effecting any such conversion. Subject to such per share dividend arrearage equalization, if there is a dividend arrearage on the SeriesA-1 Preferred Stock at the time of any conversion of the SeriesA-1 Preferred Stock into Series B Preferred Stock, the shares of Series B Preferred Stock issued upon the conversion shall be deemed to be subject to the same dividend arrearage as all other then outstanding shares of Series B Preferred Stock.

If we were to cause the conversion of the outstanding shares of SeriesA-1 Preferred Stock into shares of Series B Preferred Stock at a time when the Series B Preferred Stock were trading at a price lower than the trading price of the SeriesA-1 Preferred Stock, holders of the SeriesA-1 Preferred Stock would likely experience an immediate and potentially material decrease in the market value of the SeriesA-1 Preferred Stock shares they hold and of the Series B Preferred Stock shares they would receive upon the conversion. For more information on this risk, see “Risk Factors—Risks Relating to the SeriesA-1 Preferred Stock—We may have the right to convert the outstanding shares of SeriesA-1 Preferred Stock into shares of Series B Preferred Stock at any time.”

If any of the Proposals are adopted and the Board declares a dividend of SeriesA-1 Preferred Stock on a 1:10 or 1:20 basis, there will not be enough authorized shares of Series B Preferred Stock to permit conversion of the SeriesA-1 Preferred Stock into Series B Preferred Stock. The Board could in the future seek stockholder approval to increase the authorized number of shares of Preferred Stock in an amount sufficient to permit conversion of the SeriesA-1 Preferred Stock into Series B Preferred Stock, and then we would have the ability to exercise this conversion right.

No Liquidation Preference

In the event of any liquidation, dissolution or winding up of the Company, any amounts remaining available for distribution to stockholders after payment of all liabilities of the Company will be distributed equally among the holders of Common Stock, the holders of SeriesA-1 Preferred Stock and the holders of Series B Preferred Stock, with each share of SeriesA-1 Preferred Stock and each share of Series B Preferred Stock being treated as though it were a share of our Common Stock. Neither holders of SeriesA-1 Preferred Stock nor holders of Series B Preferred Stock have any preference over the holders of our Common Stock on any liquidation, dissolution or winding up of the Company. The holders of SeriesA-1 Preferred Stock rank equally with the holders of Series B Preferred Stock. See “Risk Factors—Risks Relating to the SeriesA-1 Preferred Stock—The SeriesA-1 Preferred Stock and the Series B Preferred Stock will rank junior to all of our and our subsidiaries’ liabilities in the event of a bankruptcy, liquidation or winding up of our or our subsidiaries’ business.”

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Description of the SeriesA-1 Preferred Stock

Voting Rights

The holders of shares of SeriesA-1 Preferred Stockvote together with the shares of Common Stock and the shares of Series B Preferred Stock(and not as a separate class), except as required by law or the SeriesA-1 Certificate of Designation. Each SeriesA-1 Preferred Stock holder is entitled to one vote for each share of SeriesA-1 Preferred Stock held on the record date for a vote. If an amendment requiring stockholder approval is proposed to our amended and restated certificate of incorporation, the holders of the SeriesA-1 Preferred Stock and the holders of the Series B Preferred Stockvote together with the holders of the Common Stock as a single class, but neither the holders of the SeriesA-1 Preferred Stock nor the holders of the Series B Preferred Stockis entitled to a class vote on the amendment, unless the proposed amendment would adversely affect the special rights, preferences, privileges and voting powers of the SeriesA-1 Preferred Stock or Series B Preferred Stock, respectively, or increase or decrease the aggregate number of authorized shares of SeriesA-1 Preferred Stock or Series B Preferred Stock. For more information on the limited voting rights of the SeriesA-1 Preferred Stock, see “Risk Factors—Risks Relating to the SeriesA-1 Preferred Stock—Voting rights on the SeriesA-1 Preferred Stock generally will be limited to voting together with the holders of the Common Stock and Series B Preferred Stock as a single class, and the holders of the SeriesA-1 Preferred Stock and the holders of the Series B Preferred Stock collectively will have only a small percentage of the voting power on any matter submitted to the holders of the Common Stock and the SeriesA-1 Preferred Stock and Series B Preferred Stock, voting together as a single class”and“Risk Factors—Risks Relating to the SeriesA-1 Preferred Stock—Holders of the SeriesA-1 Preferred Stock will not have any right, as a separate class, to elect any members of our Board of Directors.” The Series A-1 Preferred Proposal and the Alternative Series A-1 Preferred Proposal, if adopted, would result in a loss of the right of holders of shares of Series A-1 Preferred Stock to vote on the increase or decrease of authorized shares of Series A-1 Preferred Stock.

Treatment in Merger

If the Company is party to any merger or consolidation in which Common Stock is changed into or exchanged for stock or other securities of any other person (or the Company) or cash or any other property (or a right to receive the foregoing), the Company will use all commercially reasonable efforts to make provision so that each outstanding share of SeriesA-1 Preferred Stockshall be treated as if such share were an additional outstanding share of Common Stock in connection with any such transaction. No assurance can be given, however, that the Company’s efforts will be successful. Further, the Company could be involved in transactions other than a merger or consolidation, such as a tender offer by the Company or a third party, in which Common Stock might be changed into or exchanged for stock or other securities of another person (or the Company) or cash or any other property (or a right to receive the foregoing) in which the outstanding shares of SeriesA-1 Preferred Stockwould not be treated as if such shares were additional outstanding shares of Common Stock.

Limited Anti-dilution Adjustments; No Price Protection

The SeriesA-1 Preferred Stock will not be adjusted and no additional shares of SeriesA-1 Preferred Stock will be issued solely as a result of any future change to or affecting our Common Stock, except that we will use reasonable efforts to make a corresponding pro rata adjustment to the SeriesA-1 Preferred Stock if we effect any stock dividend, stock split or combination of our Common Stock.

No Sinking Fund

There is no sinking fund for the SeriesA-1 Preferred Stock.

Form and Trading System

The SeriesA-1 Preferred Stock are uncertificated shares of our Preferred Stock. Record ownership of the SeriesA-1 Preferred Stock is reflected on the records of our transfer agent, Computershare Trust Company, N.A. (“Computershare”). Computershare shows the carrying broker-dealers or other custodians (which may include banks

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Description of the SeriesA-1 Preferred Stock

or other depositary institutions) of the underlying Overstock stockholders as the owners of record of the SeriesA-1 Preferred Stock. The records of the carrying broker-dealer or other custodian, in turn, show their Overstock stockholder clients or customers as the beneficial owners of the SeriesA-1 Preferred Stock.

The term “digital” refers to the blockchain technology elements of the SeriesA-1 Preferred Stock that are intended to enhance investor experience through added transparency. The blockchain allows a “courtesy copy” of the records of the SeriesA-1 Preferred Stock maintained by Computershare to be viewable, as a convenience and with no controlling effect, on the publicly available distributed ledger. Computershare’s records, however, govern the record ownership for the SeriesA-1 Preferred Stock in all circumstances.

The user experience for the SeriesA-1 Preferred Stock is not analogous to one involving a virtual currency or any other anonymous bearer digital instrument that tradespeer-to-peer on a distributed ledger because the SeriesA-1 Preferred Stock are conventional uncertificated securities, with traditional books and records kept by a traditionalSEC-regulated transfer agent. Distributed ledger technology does not play a role in the sale, issuance, transfer or custody of the SeriesA-1 Preferred Stock.

The SeriesA-1 Preferred Stock is not listed on any national market or other recognized securities exchange or any automated dealer quotation system or other recognized trading market. The tZERO ATS, which is operated by tZERO ATS, LLC, anSEC-registered broker-dealer and member of FINRA and SIPC, is currently the only venue where the SeriesA-1 Preferred Stock can trade. The SeriesA-1 Preferred Stock is currently trading on the tZERO ATS in limited numbers. Outside of the following limited circumstances, Computershare does not registerpeer-to-peer transfers of record ownership of the SeriesA-1 Preferred Stock, and the only way to effect a sale of the SeriesA-1 Preferred Stock is through an order submitted to the tZERO ATS’ order matching system by anATS-subscribing broker-dealer on behalf of its customer. Computershare may registerpeer-to-peer transfers in its official record only in limited circumstances, such as a transfer from broker-dealer to broker-dealer, with the stockholder’s carrying broker-dealer being reflected as the record holder, or a transfer by a stockholder who is the record holder pursuant to a divorce decree or other transfers from record holders that do not constitute a “sale” for securities laws purposes, such as gifts (and then only following compliance with Computershare’s procedures, including delivery of appropriate documentation). See “Risk Factors—Risks Relating to the SeriesA-1 Preferred Stock—Our SeriesA-1 Preferred Stock may only be sold through the tZERO ATS.”

Stockholders are not required to open an account with a broker-dealer that subscribes to the tZERO ATS in order to receive SeriesA-1 Preferred Stock. In order to sell the SeriesA-1 Preferred Stock, however, you must open an account with anATS-subscribing broker-dealer (which currently only includes Dinosaur Financial Group, LLC (“Dinosaur”), anSEC-registered broker-dealer and member of FINRA and SIPC), or with a broker-dealer that itself maintains an account with anATS-subscribing broker-dealer. Orders may be entered on the tZERO ATS by anATS-subscribing broker-dealer (which currently only includes Dinosaur), or with a broker-dealer that itself maintains an account with anATS-subscribing broker-dealer on behalf of its customers. Orders properly submitted to the tZERO ATS are matched by the tZERO ATS’ order matching system in accordance with its rules, and Electronic Transaction Clearing, Inc. (“ETC”) clears transactions effected on the tZERO ATS by Dinosaur. At this time, trades on the tZERO ATS settle on the trade date; there is notwo-day settlement process.

To give the Board flexibility to address trading or other issues that may arise with respect to the tZERO ATS or Dinosaur or ETC, both the SeriesA-1 Preferred Proposal and the Alternative SeriesA-1 Preferred Proposal would permit the Board to change or add alternative trading systems, trading markets or venues on which the SeriesA-1 Preferred Stock may be sold.

Transfer Agent and Registrar

Computershare is the transfer agent and registrar, and its affiliate, Computershare Inc., will be the payment and conversion agent for the SeriesA-1 Preferred Stock.

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Description of the Series B Preferred Stock

The following description is a summary of the material terms of our Series B Preferred Stock as currently in effect. This summary is subject to, and qualified in its entirety by, the rights, preferences, powers and privileges of the Series B Preferred Stock, set forth in the Series B Certificate of Designation, which was filed with the SEC as an exhibit to a Current Report onForm 8-K on December 15, 2016. See also “Risk Factors” and the other information in this Proxy Statement.

Our Authorized Series B Preferred Stock

Under our amended and restated certificate of incorporation, our Board is authorized, without further stockholder action, to issue up to 5,000,000 shares of Preferred Stock, par value $0.0001 per share, in one or more series, with such powers, designations, privileges, preferences and relative, participating, optional and other rights and such qualifications, limitations and restrictions thereof as shall be set forth in the resolutions providing therefor. As of the date hereof, and giving effect to the previously filed certificate of correction filed on [                    ], 2019, 3,000,000 shares of Preferred Stock have been so designated, with 1,000,000 shares having been designated asSeries A-1 Preferred Stock and 2,000,000 shares having been designated as Series B Preferred Stock.

The Series B Preferred Stock is fully paid and nonassessable. Holders of Series B Preferred Stock have no preemptive or preferential or other rights to purchase or subscribe for any of the Company’s stock, obligations, warrants or other securities.

Rank

Shares of the Series B Preferred Stock rank equally with the SeriesA-1 Preferred Stock, senior to our Common Stock with respect to dividends and equal to our Common Stock with respect to the distribution of our assets upon the liquidation, dissolution and winding up of the Company. In addition, the SeriesA-1 Preferred Stock and the Series B Preferred Stock, with respect to rights upon our liquidation, winding up or dissolution, are structurally subordinated to existing and future indebtedness of our subsidiaries as well as the capital stock of our subsidiaries held by third parties.

As of September 30, 2019, we had liabilities of approximately $231 million, and we may incur significant additional debt in the future. See our Quarterly Report onForm 10-Q for the period ended September 30, 2019, which is incorporated into the Proxy Statement by reference. See “Risk Factors—Risks Relating to the SeriesA-1 Preferred Stock—The SeriesA-1 Preferred Stock and the Series B Preferred Stock will rank junior to all of our and our subsidiaries’ liabilities in the event of a bankruptcy, liquidation or winding up of our or our subsidiaries’ business.”

Dividends

Holders of Series B Preferred Stock are entitled to an annual cash dividend at the annual rate of 1% multiplied by $15.68, in preference to any dividend payment to the holders of our Common Stock, out of funds of the Company legally available for payment of dividends and subject to declaration by our Board. However, there is no assurance of any payment of any dividends on the Series B Preferred Stock. We have no obligation to pay any dividends to the holders of Series B Preferred Stock unless (and only to the extent that) our Board approves and declares dividend payments to the holders of Series B Preferred Stock or we pay a dividend to the holders of our Common Stock. Dividends on the Series B Preferred Stock are cumulative. If declared, dividends are paid to holders of record on a date selected by our Board in its sole discretion. Dividends not paid accumulate annually on December 15 of each year, whether or not the Company has earnings or profits, whether or not there are funds legally available for the payment of dividends and whether or not dividends are declared on the Series B Preferred Stock, and are entitled to be paid prior to any dividend to the holders of our Common Stock. Dividends on the SeriesA-1 Preferred Stock and the Series B Preferred Stock are paid equally with one another.

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Description of the Series B Preferred Stock

In addition to its preferential dividend rights, the Series B Preferred Stock is also entitled to participate in any dividend paid to the holders of our Common Stock, subject to the limitations set forth in the Series B Certificate of Designation. If the record date for any dividend to the holders of our Common Stock occurs while shares of Series B Preferred Stock are outstanding, the holders of Series B Preferred Stock outstanding on the record date are entitled to the same amount per share of Series B Preferred Stock as is paid per share of Common Stock.

Redemption

The Series B Preferred Stock is not subject to redemption at our option.

No Conversion

Holders of the Series B Preferred Stock do not have any right to convert their shares into any other security or to exchange their shares for any other security, including our Common Stock.

No Liquidation Preference

In the event of any liquidation, dissolution or winding up of the Company, any amounts remaining available for distribution to stockholders after payment of all liabilities of the Company will be distributed equally among the holders of Common Stock, the holders of SeriesA-1 Preferred Stock and the holders of Series B Preferred Stock, with each share of SeriesA-1 Preferred Stock and each share of Series B Preferred Stock being treated as though it were a share of our Common Stock. Neither holders of SeriesA-1 Preferred Stock nor holders of Series B Preferred Stock have any preference over the holders of our Common Stock on any liquidation, dissolution or winding up of the Company. The holders of SeriesA-1 Preferred Stock rank equally with the holders of Series B Preferred Stock. See “Risk Factors—Risks Relating to the SeriesA-1 Preferred Stock—The SeriesA-1 Preferred Stock and the Series B Preferred Stock will rank junior to all of our and our subsidiaries’ liabilities in the event of a bankruptcy, liquidation or winding up of our or our subsidiaries’ business.”

Voting Rights

The holders of shares of Series B Preferred Stock vote together with the shares of Common Stock and the shares ofSeries A-1 Preferred Stock (and not as a separate class), except as required by law or the Series B Certificate of Designation. Each Series B Preferred Stock holder will be entitled to one vote for each share of Series B Preferred Stock held on the record date for a vote. If an amendment requiring stockholder approval is proposed to our amended and restated certificate of incorporation, the holders of the SeriesA-1 Preferred Stock and the holders of the Series B Preferred Stock vote together with the holders of the Common Stock as a single class, but neither the holders of the SeriesA-1 Preferred Stock nor the holders of the Series B Preferred Stock is entitled to a class vote on the amendment, unless the proposed amendment would adversely affect the special rights, preferences, privileges and voting powers of the SeriesA-1 Preferred Stock or Series B Preferred Stock, respectively, or increase or decrease the aggregate number of authorized shares of SeriesA-1 Preferred Stock or Series B Preferred Stock. For more information on the limited voting rights of the Series B Preferred Stock, see “Risk Factors—Risks Relating to the SeriesA-1 Preferred Stock—Voting rights on the SeriesA-1 Preferred Stock generally will be limited to voting together with the holders of the Common Stock and Series B Preferred Stock as a single class, and the holders of the SeriesA-1 Preferred Stock and the holders of the Series B Preferred Stock collectively will have only a small percentage of the voting power on any matter submitted to the holders of the Common Stock and the SeriesA-1 Preferred Stock and Series B Preferred Stock, voting together as a single class.” The Series B Preferred Proposal, if adopted, would result in the loss of the right of holders of shares of Series B Preferred Stock to vote on the increase or decrease of authorized shares of Series B Preferred Stock.

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Description of the Series B Preferred Stock

Treatment in Merger

If the Company is party to any merger or consolidation in which Common Stock is changed into or exchanged for stock or other securities of any other person (or the Company) or cash or any other property (or a right to receive the foregoing), the Company will use all commercially reasonable efforts to make provision so that each outstanding share of Series B Preferred Stock shall be treated as if such share were an additional outstanding share of Common Stock in connection with any such transaction. No assurance can be given, however, that the Company’s efforts will be successful. Further, the Company could be involved in transactions other than a merger or consolidation, such as a tender offer by the Company or a third party, in which Common Stock might be changed into or exchanged for stock or other securities of another person (or the Company) or cash or any other property (or a right to receive the foregoing) in which the outstanding shares of Series B Preferred Stock would not be treated as if such shares were additional outstanding shares of Common Stock.

Limited Anti-dilution Adjustments; No Price Protection

The Series B Preferred Stock will not be adjusted and no additional shares of Series B Preferred Stock will be issued solely as a result of any future change to or affecting our Common Stock, except that we will use reasonable efforts to make a corresponding pro rata adjustment to the Series B Preferred Stock if we effect any stock dividend, stock split or combination of our Common Stock.

No Sinking Fund

There is no sinking fund for the Series B Preferred Stock.

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Risk Factors

The following risk factors relating to the Dividend should be carefully considered, in addition to other information contained in this Proxy Statement, in deciding how to vote on the Proposals. You should consider carefully the risks and uncertainties described below and filings we make with the SEC from time to time, all of which are incorporated by reference in the Proxy Statement.

Risks Relating to the SeriesA-1 Preferred Stock

Our SeriesA-1 Preferred Stock may only be sold through the tZERO ATS.

The SeriesA-1 Certificate of Designation provides that the SeriesA-1 Preferred Stock can be sold only on the tZERO ATS, with the record of beneficial ownership updated and recorded by a stockholder’sATS-subscribing broker-dealer on a book-entry basis. As a result, we expect that sales of the SeriesA-1 Preferred Stock will settle on the trade date. The SeriesA-1 Preferred Stock is not and will not be listed on any national securities exchange or other trading market of any kind. The limitation on trading shares of SeriesA-1 Preferred Stock through the tZERO ATS may adversely affect the liquidity for, and market price of, the shares of SeriesA-1 Preferred Stock. It may at times be very difficult to sell any shares of the SeriesA-1 Preferred Stock.

The SeriesA-1 Preferred Stock may only be sold through a brokerage account established with a broker-dealer that subscribes to the tZERO ATS. Currently, Dinosaur is the only broker-dealer that facilitates trades of any security on the tZERO ATS. Unless and until another broker-dealer subscribes to the tZERO ATS or maintains an account with anATS-subscribing broker-dealer, any holder of SeriesA-1 Preferred Stock that wishes to sell its shares must open an account at Dinosaur. While tZERO ATS, LLC is working to add additional broker-dealer subscribers to tZERO ATS, there is no assurance that any additional subscribers will be added, and Dinosaur could continue to be the onlyATS-subscribing broker-dealer. If Dinosaur for any reason ceases to operate, there would be no broker-dealer to effect sales of the SeriesA-1 Preferred Stock on tZERO ATS. This could prevent all trading in the SeriesA-1 Preferred Stock and would likely materially and adversely affect the trading prices of the SeriesA-1 Preferred Stock. However, both the SeriesA-1 Preferred Proposal and the Alternative SeriesA-1 Preferred Proposal would permit the Board to change or add additional alternative trading systems, trading markets or venues on which the SeriesA-1 Preferred Stock may be sold.

Likewise, ETC is the only broker-dealer that clears transactions effected on the tZERO ATS. If for any reason ETC ceases to clear trades for Dinosaur or refuses to clear trades for any futureATS-subscribing broker-dealers of tZERO ATS and no clearing firm succeeds to ETC, trading in the SeriesA-1 Preferred Stock on the tZERO ATS may be interrupted and such an interruption would likely materially and adversely affect the trading price of the SeriesA-1 Preferred Stock.

The tZERO ATS has had limited volume. Even if a more liquid trading market for the SeriesA-1 Preferred Stock does develop on the tZERO ATS utilizing technology developed by our majority owned subsidiary, tZERO Group, Inc. (“tZERO”), the depth and liquidity of that market and the ability to sell the SeriesA-1 Preferred Stock may nevertheless be limited, which may have a material adverse effect on the liquidity for, and the market price of, the SeriesA-1 Preferred Stock.

Moreover,peer-to-peer transfers of the SeriesA-1 Preferred Stock outside of orders submitted to the tZERO ATS byan ATS-subscribing broker-dealer, or with a broker-dealer that itself maintains an account with anATS-subscribingbroker-dealer, on behalf of its customers (“peer-to-peer transfers”), are not permitted, subject to limited circumstances. For clarity, a transfer of Series A-1 Preferred Stock that does not result in a change in beneficial ownership is not apeer-to-peer transfer (for example, a transfer of Series A-1 Preferred Stock by a holder who is a registered holder on Computershare’s share register to a brokerage account would not be restricted or considered a peer-to-peer transfer). Outside of the following limited circumstances, Computershare will not registerpeer-to-peer transfers of record ownership of the SeriesA-1 Preferred Stock, and the only way to effect a sale of the SeriesA-1 Preferred Stock is through an order submitted to the tZERO ATS’ order matching system by anATS-subscribing broker-dealer on behalf of its customer. Computershare may registerpeer-to-peer transfers in its official record only in limited circumstances, such as a transfer from broker-dealer to broker-dealer, with the stockholder’s carrying broker-dealer being reflected as

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Risk Factors

the record holder, or a transfer by a stockholder who is the record holder pursuant to a divorce decree or other transfers from record holders that do not constitute a “sale” for securities laws purposes, such as gifts (and then only following compliance with Computershare’s procedures, including delivery of appropriate documentation). Moreover, the Series A-1 Preferred Proposal and Alternative Series A-1 Preferred Proposal both permit transactions between DTC participants through the facilities of DTC. However, both the SeriesA-1 Preferred Proposal and the Alternative SeriesA-1 Preferred Proposal would permit the Board to exclude additional transactions or classes of transactions from the requirement to make “sales” on the tZERO ATS.

Our obligation to pay dividends on the SeriesA-1 Preferred Stock is limited, and our ability to pay dividends on the SeriesA-1 Preferred Stock may be limited.

Our obligation to pay preferential dividends on the SeriesA-1 Preferred Stock is subject to our Board declaring such dividend payments. Further, although we will be contractually restricted from paying a dividend on the Common Stock unless we have paid preferential cumulative $0.16 per share annual dividends on the SeriesA-1 Preferred Stock and preferential cumulative 1.0% annual dividends on the Series B Preferred Stock, we have never paid a dividend on the Common Stock and we have no intention of doing so. Consequently, our failure to pay preferential dividends on the SeriesA-1 Preferred Stock and on the Series B Preferred Stock might have no legal effect on us at all, although it could adversely affect the liquidity for, and trading prices of, the SeriesA-1 Preferred Stock and of the Series B Preferred Stock. Further, our payment of any dividends will be subject to contractual and legal restrictions and other factors our Board deems relevant. Further, we may elect not to pay dividends on the SeriesA-1 Preferred Stock, the Series B Preferred Stock or both rather than limiting other proposed expenditures, including expenditures that may not be contractually required. Moreover, agreements governing any future indebtedness of ours may further limit our ability to pay dividends on our capital stock, including the SeriesA-1 Preferred Stock and the Series B Preferred Stock. In addition, our ability to pay dividends is limited by applicable law. Although there are no arrearages in cumulative preferred dividends and we declared and paid a cash dividend of $0.16 per share to the holders of our then outstanding preferred stock during 2017, 2018 and 2019, there is no assurance that we will be able or that our Board will decide to do so in 2020 or the future. Any of the foregoing facts or events could have a material adverse effect on the holders of the SeriesA-1 Preferred Stock and the holders of the Series B Preferred Stock and on the liquidity for, and trading prices of, the SeriesA-1 Preferred Stock and the Series B Preferred Stock.

Voting rights on the SeriesA-1 Preferred Stock generally will be limited to voting together with the holders of the Common Stock and Series B Preferred Stock as a single class, and the holders of the SeriesA-1 Preferred Stock and the holders of the Series B Preferred Stock collectively will have only a small percentage of the voting power on any matter submitted to the holders of the Common Stock and the SeriesA-1 Preferred Stock and Series B Preferred Stock, voting together as a single class.

Voting rights of the SeriesA-1 Preferred Stock generally will be limited to voting together with the holders of the Common Stock and Series B Preferred Stock, as a single class. If an amendment requiring stockholder approval is proposed to our amended and restated certificate of incorporation, the holders of the SeriesA-1 Preferred Stock and the holders of the Series B Preferred Stock will vote together with the holders of the Common Stock as a single class, but neither the holders of the SeriesA-1 Preferred Stock nor the holders of the Series B Preferred Stock will be entitled to a class vote on the amendment, unless the proposed amendment would adversely affect the special rights, preferences, privileges and voting powers of the SeriesA-1 Preferred Stock or Series B Preferred Stock, respectively. The Proposals would eliminate the requirement that holders of the SeriesA-1 Preferred Stock and Series B Preferred Stock vote upon amendments to increase or decrease the aggregate number of authorized shares of SeriesA-1 Preferred Stock or Series B Preferred Stock, respectively. These limited voting rights could have a material adverse effect on holders of SeriesA-1 Preferred Stock and holders of Series B Preferred Stock and on the trading prices of the SeriesA-1 Preferred Stock and the Series B Preferred Stock.

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Risk Factors

Holders of the SeriesA-1 Preferred Stock will not have any right, as a separate class, to elect any members of our Board of Directors.

The holders of the SeriesA-1 Preferred Stock will have no right as a separate class to elect any members of our Board under any circumstances, including upon any failure of our Board to declare or pay any dividend on the SeriesA-1 Preferred Stock. Further, the holders of the SeriesA-1 Preferred Stock and the holders of the Series B Preferred Stock, together, also will have no right by themselves to elect any members of our Board under any circumstances. The holders of the SeriesA-1 Preferred Stock and the holders of the Series B Preferred Stock will be entitled only to vote with the holders of the Common Stock as a single class in the election of directors and on any other matter coming before a vote of the holders of the Common Stock. Holders’ lack of such rights could have a material adverse effect on holders of the SeriesA-1 Preferred Stock and the holders of the Series B Preferred Stock and the liquidity for, and trading prices of, the SeriesA-1 Preferred Stock and the Series B Preferred Stock.

Holders of SeriesA-1 Preferred Stock will have no rights with respect to our Common Stock.

Holders of SeriesA-1 Preferred Stock will have no rights with respect to our Common Stock, and no right to convert shares of SeriesA-1 Preferred Stock into shares of Common Stock or to exchange shares of SeriesA-1 Preferred Stock for shares of Common Stock, except that holders of SeriesA-1 Preferred Stock will have the right to vote with the Common Stock on any matter submitted to a vote of the holders of the Common Stock, the right to receive payments upon liquidation equallywith the holders of the Common Stock, and the right to receive dividends in preference to the holders of the Common Stock and to participate in any dividend paid to the holders of our Common Stock, subject to the limitations set forth in the SeriesA-1 Certificate of Designation.

The SeriesA-1 Preferred Stock and the Series B Preferred Stock will rank junior to all of our and our subsidiaries’ liabilities in the event of a bankruptcy, liquidation or winding up of our or our subsidiaries’ business.

In the event of our bankruptcy, liquidation or winding up, our assets will be available to make payments to holders of SeriesA-1 Preferred Stock and to holders of Series B Preferred Stock only after all of our liabilities have been paid, and neither the SeriesA-1 Preferred Stock nor the Series B Preferred Stock will have any preference over the Common Stock in the event of our bankruptcy, liquidation or winding up. In addition, the SeriesA-1 Preferred Stock and Series B Preferred Stock will rank structurally junior to all existing and future liabilities of our subsidiaries. Your rights to participate in the assets of our subsidiaries upon any liquidation or reorganization of any subsidiary will rank junior to the claims of creditors. In the event of our bankruptcy, liquidation or winding up, there may not be sufficient assets remaining, after paying our and our subsidiaries’ liabilities, to pay any amounts to the holders of SeriesA-1 Preferred Stock or Series B Preferred Stock then outstanding. We may incur significant debt or other liabilities in the future, and the SeriesA-1 Preferred Stock and Series B Preferred Stock contain no covenant or restriction on our ability to incur debt or other obligations. Any bankruptcy, liquidation or winding up of our company or any of its wholly or partially owned subsidiaries would have a material adverse effect on the liquidity for, and trading prices of, the SeriesA-1 Preferred Stock.

Moreover, we do not own all of the equity securities of our subsidiaries, including our majority owned subsidiary, tZERO. For example, we have adopted an employee equity incentive plan pursuant to which tZERO has issued, and may continue to issue, shares or other equity interests or awards having the economic effects of equity interests to employees. As a result, following satisfaction of the claims of creditors of those subsidiaries as discussed above, our right to receive distributions as a shareholder with respect to our equity interests in those majority owned subsidiaries will be shared with third party equity holders of tZERO and our other subsidiaries, whether now existing or created in the future, including our employees holding shares of any of them.

The restrictions on the tax reporting of holder’s cost basis in shares of SeriesA-1 Preferred Stock will not allow normal tax planning in the sale of shares of SeriesA-1 Preferred Stock and may result in disadvantageous tax consequences to a seller of SeriesA-1 Preferred Stock.

Only one method of cost basis reporting (thefirst-in,first-out, or “FIFO” method) is available for the SeriesA-1 Preferred Stock. As a result, sellers of SeriesA-1 Preferred Stock may be required to pay more tax on their sales or to

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Risk Factors

pay taxes earlier than if other normal methods of cost basis reporting had been available, which could have an adverse tax effect on sellers of SeriesA-1 Preferred Stock and the market price of the SeriesA-1 Preferred Stock.

The record of ownership of each digital wallet will be available to the general public and it may be possible for members of the public to determine the identity of the record holders of wallets.

Although the record of ownership included in the blockchain is anon-controlling “courtesy copy” of the records maintained by Computershare, it will be made publicly available. The publicly available information will include the digital wallet address of each holder of record transacting in SeriesA-1 Preferred Stock and the entire history of each digital wallet, but it will not include any personal identifiable information. As a result, it may be possible for members of the public to determine the identity of the record holders of certain wallets based on the publicly available information in the blockchain copy, as well as other publicly available information, including any ownership reports required to be filed with the SEC regarding the SeriesA-1 Preferred Stock.

The SeriesA-1 Preferred Stock depends on Computershare as the transfer agent for the SeriesA-1 Preferred Stock.

Computershare serves as the transfer agent for the SeriesA-1 Preferred Stock and ownership of the SeriesA-1 Preferred Stock is based upon the books and records of Computershare. Our agreement with Computershare can be terminated by either party on 60 days’ notice. If Computershare chooses to exercise its termination rights or otherwise ceases to operate as a transfer agent, we would seek to engage a successor transfer agent. In the absence of finding such a successor, Overstock would need to assume the role of transfer agent. While we believe we could successfully assume the role of transfer agent, no assurance can be given that we would be able to do so and if we are unable to do so the trading market for the SeriesA-1 Preferred Stock would be adversely affected and it may be difficult or impossible for Overstock to pay dividends or liquidation preference or provide voting rights to the correct holders of record of the SeriesA-1 Preferred Stock.

The potential application of U.S. laws regarding traditional investment securities to the SeriesA-1 Preferred Stock is unclear.

We believe that the SeriesA-1 Preferred Stock should be treated as any other conventional, uncertificated book-entry security. However, various regulators may disagree with this assertion and conclude that the SeriesA-1 Preferred Stock should not be treated as any other traditional investment security. For example, we believe that the SeriesA-1 Preferred Stock is not a “digital asset security” within the meaning of the July 8, 2019 Joint Staff Statement on Broker-Dealer Custody of Digital Asset Securities (the “July Statement”), and that as a result, broker-dealers will have a good control location consistent with the July Statement. However, federal securities regulatory authorities may disagree with that conclusion and we could be required to take further steps with regulators to establish a good control location. The occurrence of any such issue or dispute could have a material adverse effect on the liquidity for, and market price of, the SeriesA-1 Preferred Stock. In addition, if regulatory authorities take the position that SeriesA-1 Preferred Stock is a “digital asset security,” then broker-dealers may need to submit a Form CMA with FINRA in order to hold the SeriesA-1 Preferred Stock on your behalf, and that could prevent other broker-dealers from becoming subscribers to the tZERO ATS. As a result, holders of the SeriesA-1 Preferred Stock may not be able to open an account with anotherATS-subscribing broker-dealer authorized to facilitate trading of the SeriesA-1 Preferred Stock on the tZERO ATS.

If we elect to repurchase the SeriesA-1 Preferred Stock on the tZERO ATS, it could have a material adverse effect on the liquidity in, and trading prices of, the SeriesA-1 Preferred Stock.

We do not currently intend to repurchase any of the SeriesA-1 Preferred Stockon the tZERO ATS after they are issued. However, we could do so, subject to applicable regulations regarding issuer repurchases of their capital stock. If we do so, we would do so only at prices lower than the prices at which we are entitled to redeem the shares. If we

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Risk Factors

repurchase shares of SeriesA-1 Preferred Stock, the trading market for the SeriesA-1 Preferred Stockcould become less liquid, which would likely cause the trading prices of the SeriesA-1 Preferred Stockto decrease, which would give us an economic incentive to repurchase additional shares. The occurrence of the foregoing could have a material adverse effect on the liquidity in, and trading prices of, the SeriesA-1 Preferred Stock. There are no restrictions on our repurchase of shares of SeriesA-1 Preferred Stockwhile there is any arrearage in the payment of dividends.

We may have the right to convert the outstanding shares of SeriesA-1 Preferred Stock into shares of Series B Preferred Stock at any time.

Pursuant to the SeriesA-1 Certificate of Designation, we have the right to convert the SeriesA-1 Preferred Stock into Series B Preferred Stock at any time, and the terms of the Series B Preferred Stock may be amended at any time without the consent of the holders of the SeriesA-1 Preferred Stock. Currently, we may exercise this conversion right. However, if any of the Proposals are adopted and the Board declares a dividend of SeriesA-1 Preferred Stock on a 1:10 or 1:20 basis, there will not be enough authorized shares of Series B Preferred Stock to permit conversion of the SeriesA-1 Preferred Stock into Series B Preferred Stock. After any of the Proposals are adopted, the Board could seek stockholder approval to increase the authorized number of shares of Preferred Stock in an amount sufficient to permit conversion of the SeriesA-1 Preferred Stock into Series B Preferred Stock, and then we would have the ability to exercise this conversion right. Any such conversion and any such amendment of the Series B Preferred Stock could have a material adverse effect on the trading price of the SeriesA-1 Preferred Stock. If we were to do so at a time when the Series B Preferred Stock were trading at a price lower than the trading price of the SeriesA-1 Preferred Stock, holders of SeriesA-1 Preferred Stock would likely experience an immediate and potentially material decrease in the market value of the SeriesA-1 Preferred Stock they hold and of the Series B Preferred Stock they would receive upon the conversion. Moreover, the existence of this conversion right could have a negative impact on the liquidity for, and market value of, our SeriesA-1 Preferred Stock.

Risk Relating to the tZERO ATS and tZERO

tZERO ATS, LLC and tZERO are involved in ongoing discussions with regulatory authorities.

tZERO ATS, LLC and tZERO have been and remain involved in ongoing oral and written communications with, and have received subpoenas from, regulatory authorities in connection with ongoing examinations, inquiries, or investigations. Any failure of tZERO ATS, LLC, tZERO ATS, or tZERO to satisfy FINRA, the SEC, or any other regulatory authority could result in trading halts on tZERO ATS and fines and penalties being imposed. Any such trading halt will adversely affect the trading market for the SeriesA-1 Preferred Stock and may prevent the sale of SeriesA-1 Preferred Stock until the failure is rectified.

Technology on which tZERO ATS relies for its operations may not function properly.

The technology on which tZERO ATS relies may not function properly because of internal problems or as a result of cyber-attacks or external security breaches. Any such malfunction may adversely affect the ability of holders to execute trades of the SeriesA-1 Preferred Stock on tZERO ATS. Moreover, since trading in the SeriesA-1 Preferred Stock has been limited, the tZERO ATS platform may not function properly in cases of increased trading volume. If the technology used by tZERO ATS does not work as anticipated, trading of the SeriesA-1 Preferred Stock could be limited or even suspended. However, both the SeriesA-1 Preferred Proposal and the Alternative SeriesA-1 Preferred Proposal would permit the Board to change or add alternative trading systems, trading markets or venues on which the SeriesA-1 Preferred Stock may be sold.

The technology on which the tZERO ATS depends has been developed by our indirectly held majority-owned subsidiary, tZERO, and is licensed to its wholly-owned subsidiary, tZERO ATS, LLC, and the SeriesA-1 Preferred Stock depends on both tZERO and tZERO ATS, LLC, neither of which has substantial resources.

tZERO is an indirectly held majority-owned subsidiary of ours and owns 100% of the equity interest in tZERO ATS, LLC. tZERO licenses the technology to tZERO ATS, LLC, and tZERO ATS, LLC uses tZERO technology to

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Risk Factors

operate the tZERO ATS. tZERO is a growth-stage company, and neither tZERO nor tZERO ATS, LLC has substantial resources. If any one or more of the Company, tZERO or tZERO ATS, LLC were unable to fund its operations in the future, or if any one or more of them were to become the subject of a bankruptcy or other insolvency proceeding, tZERO ATS, LLC might be unable to continue to operate the tZERO ATS, and the SeriesA-1 Preferred Stock could be materially adversely affected. In any such event, or if the tZERO ATS or tZERO technology were to be unable to operate as intended for any reason, holders of our capital stock, including the SeriesA-1 Preferred Stock, could lose their ability to trade our SeriesA-1 Preferred Stock, which would have a material adverse effect on the market value of that stock, and may have a material adverse effect on the liquidity for, and the price of, our Common Stock.

Transactions involving the SeriesA-1 Preferred Stock may not be properly reflected in the digital wallet.

A significant feature of the SeriesA-1 Preferred Stock is that, while the records of Computershare (as our transfer agent) govern record ownership of the SeriesA-1 Preferred Stock, for all record holders on the transfer agent’s controlling records there is a digital wallet which is shown as anon-controlling digital “courtesy copy” on the blockchain. Following Computershare’s approval of any change in record ownership, the digital wallets on the blockchain are updated to match Computershare’s conventional books and records. To the extent that Computershare’s records and the duplicative records on the blockchain get out of sync, there could be a delay while we correct any such errors, and such errors may cause investors confusion with respect to their record holdings of the SeriesA-1 Preferred Stock, which could adversely affect the liquidity for, and market value of, the SeriesA-1 Preferred Stock.

The potential application of U.S. laws regarding virtual currencies and money transmission to tZERO ATS, LLC’s use of the Ethereum blockchain is unclear.

The tZERO technology used by the tZERO ATS uses the Ethereum blockchain for the blockchain’snon-controlling “courtesy copy” records maintained by Computershare. Although tZERO’s wholly owned subsidiary, Bitsy, Inc, maintains certain licenses in connection with virtual currency applications, none of the parties involved in the operation of the tZERO ATS using tZERO technology is licensed under the virtual currency or money transmission regulations of any state in the United States or registered with the U.S. Department of the Treasury Financial Crimes Enforcement Network (“FinCEN”). If any regulatory authority were to assert that additional licensing or registration was required by tZERO ATS, LLC or tZERO, it could affect the operations or viability of either of them, and could adversely affect the availability of the tZERO ATS as a trading venue for the SeriesA-1 Preferred Stock. This in turn would have a material adverse effect on the liquidity of the SeriesA-1 Preferred Stock and the holders’ ability to trade such securities. In addition, because tZERO ATS, LLC is a wholly-owned subsidiary of tZERO, any negative impact on the value of the tZERO ATS or tZERO technology could have an adverse impact on the value of Overstock, which would cause our stock price to decrease.

Although the SeriesA-1 Preferred Stock has characteristics similar to those of our Common Stock, the differences may adversely affect the trading prices of the SeriesA-1 Preferred Stock.

Each share of SeriesA-1 Preferred Stock is intended to have voting and dividend rights and rights upon liquidation substantially similar to those of one share of our Common Stock, except that the SeriesA-1 Preferred Stock will have a dividend preference over the Common Stock, the SeriesA-1 Preferred Stock will be limited to trading on the tZERO ATS, and we will have the right to convert the SeriesA-1 Preferred Stock into Series B Preferred Stock. These provisions may have a material adverse effect on the liquidity for, and trading price of, the SeriesA-1 Preferred Stock.

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Share Ownership of Management, Directors, Nominees and 5% Stockholders

The following table sets forth information regarding the beneficial ownership of our Common Stock,Series A-1 Preferred Stock and Series B Preferred Stock as of December 18, 2019 (except as otherwise noted below) by the following individuals or groups:

The table is based upon information supplied by officers, directors, and principal stockholders and Schedules 13D and 13G filed with the SEC. Except as otherwise indicated below or in the referenced filings, and subject to applicable community property laws, to our knowledge the persons named in the table have sole voting and investment power with respect to all shares of Common Stock,Series A-1 Preferred Stock and Series B Preferred Stock held by them. Applicable percentages are based on [        ] shares of Common Stock, [        ] shares ofSeries A-1 Preferred Stock, and [        ] shares of Series B Preferred Stock outstanding as of December 18, 2019, except as otherwise indicated below, and as adjusted as required by rules promulgated by the SEC. To our knowledge, the only holder of 5% or more of the outstanding shares of ourSeries A-1 Preferred Stock is [    ]. [To our knowledge, at December 18, 2019, none of the persons or entities described above was the beneficial owner of any shares of our Voting Series B Preferred Stock.] Amounts based on Schedule 13G filings are as of December 31, 2018 unless otherwise noted.

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Share Ownership of Management, Directors, Nominees and 5% Stockholders

The Company is not aware of any arrangements, including any pledge by any person of securities of the Company, the operation of which may at a subsequent date result in a change in control of the Company.

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Cautionary Statement Regarding Forward-Looking Statements

This Proxy Statement and other documents referenced herein contain certain statements that constitute “forward-looking statements” within the meaning of Section 27A of the Securities Act and Section 21E of the Securities Exchange Act of 1934, as amended (the “Exchange Act”). The words “anticipate,” “expect,” “believe,” “goal,” “plan,” “intend,” “estimate,” “may,” “will,” and similar expressions and variations thereof are intended to identify forward-looking statements, but are not the exclusive means of identifying such statements. Those statements appear in this Proxy Statement and the documents referenced herein and include statements regarding the intent, belief or current expectations of the Company and management that are subject to known and unknown risks, uncertainties and assumptions and other factors that could cause actual results and the timing of certain events to differ materially from future results expressed in or implied by such forward-looking statements. Factors that could cause or contribute to such differences include, but are not limited to, those discussed in the section titled “Risk Factors” beginning on page 21 of this Proxy Statement.

This Proxy Statement also contains statements that are based on the Board’s and management’s current expectations and beliefs, including statements about the actions to be taken by the Board in response to the stockholder vote, the Dividend and its benefits, the manner in which any dividend of the SeriesA-1 Preferred Stock will be effected, the timing of any dividend of the SeriesA-1 Preferred Stock, the registration of the SeriesA-1 Preferred Stock to be issued in a dividend, the expected trading market for the SeriesA-1 Preferred Stock, the actions anticipated to be taken by market participants in connection with the Dividend and trading of the SeriesA-1 Preferred Stock and the trading capabilities of the tZERO ATS.

Because forward-looking statements are inherently subject to risks and uncertainties, some of which cannot be predicted or quantified, you should not rely upon forward-looking statements as predictions of future events. The events and circumstances reflected in the forward-looking statements may not be achieved or occur or may not occur within the anticipated time frame and actual results could differ materially from those projected in the forward-looking statements. Except as required by applicable law, we do not plan to publicly update or revise any forward-looking statements contained herein, whether as a result of any new information, future events or otherwise.

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Questions and Answers about the Annual

Special Meeting and Procedural Matters

What is the purpose of the AnnualSpecial Meeting?

At our AnnualThe Special Meeting is being held to obtain stockholder approval to amend certain provisions of the Company’s certificates of designation to facilitate the payment of the Dividend by eliminating current restrictions on the SeriesA-1 Preferred Stock and to reallocate the number of authorized shares of Preferred Stock among series. As described more fully in this Proxy Statement, stockholders will act upon the matters outlined in the meeting notice provided with this proxy statement, including:following matters:

If adopted, these proposals will allow the SeriesA-1 Preferred Stock to be held by a wide group of investors. In addition, if adopted, the Proposals will reallocate the authorized Preferred Stock among series to increase the number of authorized shares of SeriesA-1 Preferred Stock to permit the Company to pay the Dividend on a 1:10 basis, as originally contemplated. Adoption of the Proposals would also result in a loss of stockholder voting rights on the increase or decrease of authorized shares of Series A-1 Preferred Stock or Series B Preferred Stock.

What is the Dividend?

On July 30, 2019, Overstock announced that the Board had declared the Dividend payable in shares of SeriesA-1 Preferred Stock to holders of record of Common Stock, SeriesA-1 Preferred Stock and Series B Preferred Stock. The Dividend would have been payable at a ratio of 1:10, meaning that one share of SeriesA-1 Preferred Stock would be issued for every ten shares of Common Stock, ten shares of SeriesA-1 Preferred Stock or ten shares of Series B Preferred Stock held by holders of such shares as of the record date.

The record date and the distribution date for the Dividend were initially set for September 23, 2019 and November 15, 2019, respectively. In view of the feedback the Company received from industry participants, investors and regulators with respect to the Dividend, and in order to provide greater liquidity, on September 18, 2019, Overstock announced that it intended to register the shares of SeriesA-1 Preferred Stock with the SEC to be issued in connection with the Dividend. Upon distribution, the Dividend shares of Series A-1 Preferred Stock will be freely tradable by non-affiliates. As a result, the Company postponed the previously announced record date and distribution date. On September 24, 2019, the Company filed a registration statement with the SEC on FormS-3 to register the SeriesA-1 Preferred Stock.

On October 28, 2019, Overstock announced that it would seek stockholder approval to amend certain provisions of the Company’s certificates of designation to facilitate the payment of the Dividend by eliminating restrictions on the SeriesA-1 Preferred Stock so the Dividend can be held by a wide group of investors and by reallocating the authorized Preferred Stock among series to pay the Dividend on a 1:10 basis.

If the SeriesA-1 Preferred Proposal is adopted, Overstock intends to promptly announce the record and distribution dates for the Dividend. As set forth in the table above under “Introduction—Matters to Be Voted on at the Special Meeting,” in the event that the SeriesA-1 Preferred Proposal is not adopted but the Alternative SeriesA-1 Preferred Proposal is adopted, Overstock will not be able to pay the Dividend on a 1:10 basis, and the Board currently anticipates declaring a dividend of the SeriesA-1 Preferred Stock on a 1:20 basis. In either case, cash will be paid in lieu of issuing any fractional shares based on the average of the last sales prices for the Series A-1 Preferred Stock as reported on tZERO ATS for the five days on which the Series A-1 Preferred Stock trades regular way on the tZERO ATS immediately preceding the distribution date for the Dividend. If the Series B Preferred Proposal is adopted, but neither the SeriesA-1 Preferred Proposal nor the Alternative SeriesA-1 Preferred Proposal is adopted, Overstock will not be able to issue the Dividend. The Board will need to consider whether these votes represent a rejection of the

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Questions and Answers about the Special Meeting and Procedural Matters

desirability of the Dividend. If all three Proposals fail, the Board will need to consider whether this vote represents a rejection by our Audit Committee’s appointmentstockholders of KPMG LLPthe desirability of the Dividend and may, depending on stockholder and stakeholder feedback, consider available alternative structures to achieve the objectives of the Dividend. These alternative structures could include, for example, if there is a sufficient number of authorized shares of Preferred Stock undesignated as our independent registered public accounting firm for 2019.to series, the issuance of a new series of Preferred Stock as a dividend or the use of depositary shares, with each depositary share representing a fraction of a share of a new series of Preferred Stock. For more information on the Proposals to be voted on, see “Proposals to Be Voted On.”

Questions and Answers about the Special Meeting and Procedural Matters

What is a quorum?

The presence in person or by proxy of the holders of a majority of the Voting Shares and a majority of the Series A-1 Preferred Stock outstanding on the Record Daterecord date will be necessary to constitute a quorum for Proposals 1 and 3 to be voted upon at the AnnualSpecial Meeting. A quorum isThe presence in person or by proxy of the holders of a majority of the Voting Shares and a majority of the Series B Preferred Stock outstanding on the record date will be necessary to transact businessconstitute a quorum for Proposal 2 to be voted upon at the meeting.Special Meeting. The relevant quorum must be present in order to take action with respect to such Proposal at the Special Meeting. Voting Shares represented by proxies that reflect abstentions or “brokernon-votes” (i.e., shares held by a broker or nominee that are represented at the meeting, but with respect to which such broker or nominee is not empowered to vote on a particular proposal) will be counted as present and entitled to vote for purposes of determining the presence of a quorum. The inspector of election will tabulate the proxies and votes cast prior to the meeting and at the meeting to determine whether a quorum is present.

How do I vote?

You may submit your voteproxy to have your shares voted via the Internet, by telephone, or in person at the annual meeting. If you received printed proxy materials, you also have the option ofby submitting your proxy card by mail or attendingyou may vote in person at the meeting and delivering the proxy card.Special Meeting. The designated proxies will vote according to your instructions; however, if you are a registered stockholder and you return an executed proxy card without specific instructions on how to vote, the proxies will vote:

“FOR”FOR” the election ofSeriesA-1 Preferred Proposal;

“FOR” the nominated directors in proposal 1;Series B Preferred Proposal; and, if necessary,

“FOR”FOR” the ratification of KPMG LLP as our independent registered public accounting firm in proposal 2.Alternative SeriesA-1 Preferred Proposal.

If you are a “street name” stockholder and you do not return instructions on how to vote to your broker, your shares will not be voted except on proposal 2.voted. The voting of shares held by “street name” stockholders is further discussed below. Additionally, in order to vote at the meeting, you will need to obtain a signed proxy from the broker or nominee that holds your shares, because the broker or nominee is the legal, registered owner of the shares. If you have the broker’s proxy, you may vote by ballot or you may complete and deliver another proxy card in person at the meeting.

				2019 Proxy Statement | 1

Questions and Answers about the Special Meeting and Procedural Matters

Can I change my vote or revoke my proxy?

Subject to the deadlines set forth in the paragraph above, you may change your vote at any time before theFebruary 12, 2020 by resubmitting your proxy is exercised byre-submitting your vote via the Internet or by telephone.

If you are a registered stockholder and have delivered a proxy, you may revoke your proxy at any time before the proxy is exercisedyour shares are voted by filing with our corporate Secretary a written notice of revocation at our Company headquarters at the address shown on the first page of this proxy statement.Proxy Statement. The revocation must be received prior to the time your shares are voted. At the meeting, you also may revoke your proxy by submitting a written revocation or a later-dated proxy to the inspector of election.election or by voting in person. Your attendance at the meeting will not by itself revoke your proxy.

If your shares are held in “street name” or you are a participant in the Overstock 401(k) plan, please contact your broker, nominee, trustee or administrator to determine whether you will be able to revoke or change your vote.

Why did I receive a notice of Internet availability of proxy materials instead of a full set of the proxy materials?

The rules of the U.S. Securities and Exchange Commission (the “SEC”) allow companies to furnish their proxy materials via the Internet. Accordingly, we sent some of our stockholders a notice of Internet availability of proxy materials for this year’s annual meeting of stockholders. Other stockholders were instead sent paper copies of the proxy materials accessible via the Internet. Instructions on how to access the proxy materials via the Internet or to request a paper copy can be found in the notice of Internet availability of proxy materials. In addition, stockholders may request proxy materials in printed form, by mail or electronically bye-mail on an ongoing basis by submitting a request to us athttp://www.overstock.com/proxy. A stockholder’s election to receive proxy materials by mail ore-mail will remain in effect until the stockholder terminates it.

Can I vote my shares by filling out and returning the notice of Internet availability of proxy materials?

No, but the notice of Internet availability of proxy materials provides instructions on how to vote your shares.

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Questions and Answers about the AnnualSpecial Meeting and Procedural Matters

How many votes are required to approve other matters that may come before the stockholders at the meeting?

The affirmative vote of the holders of a majority of the Voting Shares represented and voting at the meeting (which shares voting affirmatively also constitute at least a majority of the required quorum) will be required to approve any other matters that may properly come before the meeting, unless a different vote is required by law, by our Certificate of Incorporation or by our bylaws.

Is my vote kept confidential?

Proxies, ballots and voting tabulations identifying stockholders are kept confidential and will not be disclosed except as may be necessary to meet legal requirements.

Where do I find the voting results of the meeting?

We will announce preliminary voting results at the meeting, and will file aForm 8-K with the SEC reporting the results within four business days after the date of the meeting. You can get a copy of thatForm 8-K bye-mailing Overstock Investor Relations at ir@overstock.com or by calling the SEC at(800) SEC-0330 for the location of the nearest public reference room, or through the EDGAR system athttps://www.sec.gov. You can also get a copy from our website at [http://www.overstock.com/proxy.proxy].

Who pays for the proxy solicitation process?

We will pay the costs of soliciting proxies, including the cost of preparing, posting and mailing proxy materials. In addition to soliciting stockholders by mail, we will request brokers, banks and other nominees to solicit their customers who hold shares of Overstock common stockCommon Stock, SeriesA-1 Preferred Stock or Series B Preferred Stock in street name. We may reimburse such brokers, banks and nominees for their reasonableout-of-out-of-pocket pocket expenses. We may also use the services of our officers, directors and employees to solicit proxies, personally or by telephone, mail, facsimile or email,e-mail, without additional compensation other than reimbursement for reasonableout-of-pocket expenses. We intend to use the services of Georgeson Inc. in connection with the meeting and anticipate that the costs of such services will be approximately $9,500$[        ] plus reimbursement for reasonableout-of-pocket expenses.

How can I get an additional copy of the proxy materials?

If you would like an additional copy of this proxy statement or our 2018Form 10-K,Proxy Statement, these documents are available in digital form for download or review at [http://www.overstock.com/proxy]. Alternatively, we will promptly send a copy to you at no charge upon request by mail to Overstock.com, Inc., Attention: Investor Relations, 799 W. Coliseum Way, Midvale, Utah 84047, or bye-mailing Overstock Investor Relations at ir@overstock.com.

Who can help answer my questions?

If you have questions about voting or the proposalsProposals described in this Proxy Statement, please call Georgeson Inc., our proxy solicitor, toll-free at (866)432-2791.

Important Notice Regarding the Availability of Proxy Materials for the

AnnualSpecial Meeting of Stockholders to be held on May 9, 2019February 13, 2020

The Notice of AnnualSpecial Meeting and Proxy Statement and Annual Report onForm 10-K for the fiscal year

ended December 31, 2018 are available athttp: [http://www.overstock.com/proxyproxy]..

4 | 2019 Proxy Statement