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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.    )

Overstock.com, Inc.

799 W. Coliseum Way

Midvale, Utah 84047

NOTICE OF ANNUAL MEETING OF STOCKHOLDERS
Notice of Annual Meeting of Stockholders

To Be Held at 1:00 p.m. on May 9, 20182019

Dear Fellow Stockholders:

We cordially invite you to attend the 20182019 Annual Meeting of Stockholders of Overstock.com, Inc. (the "Company"“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, 2018. 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.

At the meeting, holders of our common stock, our Blockchain Voting Series A Preferred Stock and our Voting Series B Preferred Stock (collectively, our "Voting Shares"“Voting Shares”) will vote on the following matters:

1.

The election of three Class I directors of the Company to serve terms of three years. The Company's Board of Directors intends to present Patrick M. Byrne, Barclay F. Corbus and Jonathan E. Johnson III for election to the Board; and



2.

The ratification of the appointment of KPMG LLP as the Company's independent registered public accounting firm for the fiscal year ending December 31, 2018.

Stockholders will also consider and act upon any other matter properly coming before the Annual Meeting.

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

Holders of record of shares of our Voting Shares at the close of business on March 12, 20182019 are entitled to vote at the meeting and any postponements or adjournments. To ensure that your vote is recorded promptly,please vote as soon as possible, even if you plan to attend the meeting in person. We encourage you to vote via the Internet or by telephone. If you received a printed set of proxy materials, you also have the option of voting by completing, signing, dating and returning the proxy card that accompanied the printed materials. Submitting your vote 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.

We are mailing 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 for the year ended December 31, 20172018 (the "2017 “2018Form 10-K"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 2017 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 our proxy materials.

		By Order of the Board of Directors,
		Allison H. Abraham Chairwoman of the Board		Patrick Byrne Director & Chief Executive Officer

Midvale, Utah

March 20, 201818, 2019

Important Notice Regarding the Availability of Proxy Materials for the

Annual Meeting of Stockholders to be held on May 9, 20182019

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

ended December 31, 20172018 are available athttp://www.overstock.com/proxy.

Overstock.com, Inc.

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OVERSTOCK.COM, INC.
799 W. Coliseum Way

Midvale, Utah 84047

Proxy Statement

PROXY STATEMENT
ANNUAL MEETING OF STOCKHOLDERS
Annual Meeting of Stockholders

To Be Held at 1:00 p.m. on May 9, 20182019

General

Our Board of Directors (the "Board"“Board”) is soliciting proxies for the 20182019 Annual Meeting of Stockholders of Overstock.com, Inc. ("(“Overstock,"” the "Company," "we"“Company,” “we” or "our"“our”) to 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, 2018.2019. This Proxy Statement contains important information for you to consider when deciding how to vote on the matters before the meeting.

We have elected to provide access to our proxy materials to our stockholders via the Internet. Accordingly, a notice of Internet availability of proxy materials has been mailed to the majority of our stockholders, while other stockholders have instead received paper copies of the proxy materials accessible via the Internet. Stockholders who received the notice of Internet availability of proxy materials have the ability to access the proxy materials athttp://www.overstock.com/proxy or request that a printed set of the proxy materials be sent to them by following the instructions set forth on the notice of Internet availability of proxy materials.

Please visithttp://www.overstock.com/proxy for details on how to instruct us to send future proxy materials to you electronically bye-mail or in printed form by mail. If you choose to receive future proxy materials bye-mail, you will receive ane-mail next year with instructions containing a link to those materials or a link to a special website to access our proxy materials. Your election to receive proxy materials bye-mail or printed form by mail will remain in effect until you terminate it.

Choosing to receive future proxy materials bye-mail will allow us to provide you with the proxy materials you need in a timelier manner and will save us the cost of printing and mailing documents to you.

Our principal offices are located at 799 W. Coliseum Way, Midvale, Utah 84047, and our telephone number is(801) 947-3100.

Record Date and Voting Securities

The Board set March 12, 20182019 as the record date for the meeting. Stockholders who owned shares of our common stock, our Blockchain Voting Series A Preferred Stock and our Voting Series B Preferred Stock (collectively, our "Voting Shares"“Voting Shares”) at the close of business on that date are entitled to attend and vote at the meeting. Each share is entitled to one vote. There were 29,483,99332,733,288 Voting Shares outstanding on the record date. A majority of the outstanding Voting Shares present at the meeting in person or by proxy will constitute a quorum for the transaction of business.

Proxy Materials

Voting materials, which include this Proxy Statement, the proxy card and our Annual Report onForm 10-K for the year ended December 31, 20172018 (the "2017 “2018Form 10-K"10-K”), are first being sent or given to stockholders on or about March 21, 2018.22, 2019.

The date of this Proxy Statement is March 20, 2018.18, 2019.

QUESTIONS AND ANSWERS ABOUT THE ANNUAL MEETING
AND PROCEDURAL MATTERS
Questions and Answers about the Annual Meeting and Procedural Matters

What is the purpose of the Annual Meeting?

At our Annual Meeting, stockholders will act upon the matters outlined in the meeting notice provided with this proxy statement, including:

•

the election of directors; and



•

Questions and Answers about the Annual Meeting and Procedural Matters

If you hold Voting Shares in a retirement or savings plan or other similar plan, you may submit your vote via the Internet or by telephone or by means of the direction on the proxy card. The trustee or administrator of the plan will vote according to your directions and the rules of the plan.

What happens if a nominee is unable to stand for election?

The Nominating and Corporate Governance Committee of the Board of Directors may select a substitute nominee. In that case, if you have submitted your proxy via the Internet or by telephone or completed and returned your proxy card or voting instruction card, the proxy holders will have the discretion to vote your shares for the substitute nominee. They cannot vote for more than threetwo Class III nominees.

Can I vote via the Internet or by telephone?

You may submit your vote via the Internet or by telephone by following the instructions contained in the notice of Internet availability of proxy materials. If you received a printed set of proxy materials, you may submit your vote via the Internet or by telephone by following the instructions contained on the proxy card that accompanied the printed materials.

If you are a registered stockholder, the deadline for submitting your vote by telephone or via the Internet is 11:59 p.m. Eastern Time on May 8, 2018.2019. If you are a participant in the Overstock 401(k) plan, the deadline for submitting your voting directions by telephone or via the Internet is 2:00 a.m.11:59 p.m. Eastern Time on May 3, 2018.2, 2019.

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 the 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 exercised 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. At the meeting, you also may revoke your proxy by submitting a written revocation or a later-dated proxy to the inspector of election. Your attendance at the meeting will not by itself revoke your proxy.

If your shares are held in "street name"“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"“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'syear’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'sstockholder’s election to receive proxy materials by mail ore-mail will remain in effect until the stockholder terminates it.

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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 Annual Meeting and Procedural Matters

What is the voting requirement to approve each of the proposals?

Assuming a quorum is present, the matters to come before the Annual Meeting that are listed in the Notice of Annual Meeting of Stockholders require the votes described below to be approved.

Proposal 1—Election of Directors—Directors shall be elected by a plurality of the votes cast by the holders of Voting Shares. This means that the threetwo nominees receiving the highest numbers of Voting Shares voted "for"“for” their election will be elected as Class III members of the Board of Directors. If any nominee for director fails to receive a greater number of "for"“for” votes than "withheld"“withheld” votes or instructions, our director resignation policy requires the person to tender his or her resignation to the Chairperson of the Board within five business days following certification of the vote. See "The“The Board—Director Resignation Policy."”

With respect to the election of directors, you may vote "for"“for” or "withhold"“withhold” authority to vote for each of the nominees for election. If you "withhold"“withhold” authority to vote with respect to one or more director nominees, your vote will have no effect on the election of such nominees. Brokernon-votes also will have no effect on the election of directors. There is no cumulative voting in the election of directors.

Proposal 2—Ratification of our Audit Committee'sCommittee’s appointment of KPMG LLP as our independent registered public accounting firm—the affirmative vote of the holders of a majority of the shares of Voting Shares present in person or represented by proxy and voting on the matter (which shares voting affirmatively also constitute at least a majority of the required quorum) is required to approve this proposal. You may vote "for," "against,"“for,” “against,” or "abstain"“abstain” on this proposal. Abstentions and brokernon-votes will have no effect on the determination of whether this proposal has received the vote of a majority of the Voting Shares present or represented by proxy and voting at the meeting. However, abstentions and brokernon-votes could prevent the approval of this proposal if the number of affirmative votes, though a majority of the votes represented and cast, does not constitute a majority of the required quorum.

What are BrokerNon-Votes?

Stockholders who hold their shares through a broker or other nominee (in "street name"“street name”), must provide specific instructions to their brokers or other nominee as to how to vote their shares, in the manner prescribed by their broker or other nominee. In the absence of instructions, brokers and nominees typically have the discretion to vote such shares on the ratification of the appointment of auditors, but not onnon-routine matters. If a broker or nominee has not received voting instructions from an account holder and does not have discretionary authority to vote shares on a particular item because it is anon-routine matter, a "broker non-vote"“brokernon-vote” occurs.

Which proposals are considered "routine"“routine” or "non-routine"“non-routine”?

Only Proposal 2 (the proposed ratification of our independent registered public accounting firm) is considered a routine matter. A broker or other nominee may generally vote in their discretion on routine matters, and therefore no brokernon-votes are expected in connection with Proposal No. 2. Proposal 1 is considerednon-routine.

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How many shares of Series A Preferred, Series B Preferred and Common StockVoting Shares are outstanding and entitled to vote at the meeting?

At the Record Date, a total of 29,483,99332,733,288 Voting Shares were outstanding and entitled to vote at the meeting, consisting of 126,565 shares of Blockchain Voting Series A Preferred, Stock ("Series A Preferred"), 554,694354,694 shares of Voting Series B Preferred Stock ("(“Series B Preferred"Preferred”), and 28,802,73432,252,029 shares of Common Stock.

Are any shares entitled to a class vote on any of the proposals to be considered at the meeting?

        NoneNo shares of the outstanding sharesany class are entitled to a separate class vote on any of the proposals to be considered atproposals.

				2019 Proxy Statement | 3

Questions and Answers about the meeting. The Series A Preferred, the Series B PreferredAnnual Meeting and the Common Stock will all vote together as a single class on each of the proposals, and each share will be entitled to one vote on each of the proposals.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 by callinge-mailing Overstock Investor Relations at (801) 947-3100ir@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 at www.sec.gov.https://www.sec.gov. You can also get a copy from our website athttp://www.overstock.com/proxyproxy..

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 stock or Series B Preferred in street name. We may reimburse such brokers, banks and nominees for their reasonableout-of- 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, without additional compensation other than reimbursement for reasonableout-of-pocket expenses. We intend to use the services of a proxy solicitation firmGeorgeson 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 2017 2018Form 10-K, these documents are available in digital form for download or review athttp://www.overstock.com/proxy. Alternatively, we will promptly send a copy to you at no charge upon request by mail to

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Overstock.com, Inc., Attention: Investor Relations, 799 W. Coliseum Way, Midvale, Utah 84047, or by callinge-mailing Overstock Investor Relations at (801) 947-3100.ir@overstock.com.

Who can help answer my questions?

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

Important Notice Regarding the Availability of Proxy Materials for the

Annual Meeting of Stockholders to be held on May 9, 2018
2019

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

ended December 31, 20172018 are available athttp://www.overstock.com/proxy.

4 | 2019 Proxy Statement

PROPOSALProposal 2—RATIFICATION OF APPOINTMENT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM
Ratification of Appointment of Independent Registered Public Accounting Firm

Proposed Ratification of Appointment of KPMG LLP

The Audit Committee of the Board of Directors has appointed KPMG LLP as our independent registered public accounting firm to audit our financial statements for the fiscal year ending December 31, 20182019 and audit the effectiveness of our internal control over financial reporting as of December 31, 2018.2019. KPMG LLP has served as our independent registered public accounting firm since December 2009. Although ratification of the Audit Committee'sCommittee’s selection of KPMG LLP is not required under our bylaws or other legal requirements, we are submitting the appointment of KPMG LLP to the stockholders as a matter of good corporate practice. If the stockholders do not ratify the appointment of KPMG LLP, the Audit Committee will reconsider whether or not to retain KPMG LLP. Even if the stockholders ratify the selection of KPMG LLP, the Audit Committee may appoint a different independent registered public accounting firm or replace KPMG LLP with a different independent registered public accounting firm at any time if the Audit Committee determines that it is in the best interests of the Company and the stockholders to do so. Representatives of KPMG LLP are expected to attend the annual meeting to respond to appropriate questions and will have an opportunity to make a statement if they so desire.

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Audit Fees

KPMG LLP was engaged as our independent registered public accounting firm to audit our financial statements for the years ended December 31, 20172018 and 2016,2017, to audit the effectiveness of our internal control over financial reporting as of December 31, 20172018 and 2016,2017, to review our 20172018 and 20162017 interim financial statements, to perform services in connection with our registration statements and SEC comment letter responses, and to perform accounting consultation services. The aggregate audit fees KPMG LLP billed us for professional services were $2,168,000 in 2018 and $1,820,000 in 2017 and $1,770,000 in 2016.2017. All audit fees and other fees werepre-approved by the Audit Committee.

Audit-RelatedAudit-Related Fees

KPMG LLP billed us $32,800 in 2018 and $32,000 in 2017 and $30,000 in 2016 for the audits of our 401(k) employee benefit plan.

Tax Fees

KPMG LLP billed us $44,400 in 2018 and $54,000 in 2017 and $51,272 in 2016 for professional services rendered in connection with tax advice.

All Other Fees

KPMG LLP billed us $2,500 in 20172018 and $2,400$2,500 in 20162017 for a subscription to KPMG Accounting Research Online.

Auditor Independence

The Audit Committee has considered the role of KPMG LLP in providing us with the services described above, and has concluded that those services were compatible with the independence of KPMG LLP from management and from the Company.

Policy on Audit CommitteePre-Approval of Audit and PermissibleNon-Audit Services of Independent Registered Public Accounting Firm

General

General

The Audit Committee has adopted an Audit andNon-Audit ServicesPre-Approval Policy (the "Policy"“Policy”), which sets forth the procedures and the conditions pursuant to which all services to be performed by the independent registered public

6 | 2019 Proxy Statement

Proposal 2

accounting firm are required to bepre-approved. Under the Policy, proposed services either may bepre-approved by agreeing to a framework with descriptions of allowable services with the Audit Committee ("(“general pre-approval"pre-approval”), or require the specificpre-approval of the Audit Committee ("(“specific pre-approval"pre-approval”). Unless a type of service has received generalpre-approval, it requires specificpre-approval by the Audit Committee if it is to be provided by the independent registered public accounting firm.

The Policy describes the Audit, Audit-related, Tax and All Other Services that are subject to the generalpre-approval of the Audit Committee. The Audit Committee annually reviews andpre-approves the services that may be provided by the independent registered public accounting firm that are subject to generalpre-approval. Under the Policy, the Audit Committee may delegate either type ofpre-approval authority to its chairperson or any other member or members. The member to whom such authority is delegated must report, for informational purposes only, anypre-approval decisions to the Audit Committee at its next meeting. The Policy does not delegate the Audit Committee'sCommittee’s responsibilities topre-approve services performed by the independent registered public accounting firm to management.

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Audit Services

The annual audit services engagement scope and terms are subject to the generalpre-approval of the Audit Committee. Audit services include the annual financial statement audit (including required interim reviews performed in accordance with applicable standards) and other procedures required to be performed by the independent registered public accounting firm to be able to form an opinion on our consolidated financial statements. Audit services also include the attestation engagement for the independent registered public accounting firm'sfirm’s audit of the effectiveness of internal control over financial reporting. The Policy provides that the Audit Committee will monitor the audit services engagement throughout the year and will also approve, if necessary, any changes in terms and conditions resulting from changes in audit scope or other items. The Policy provides for Audit Committeepre-approval of specific audit services outside the engagement scope.

Audit-related Services

Audit-related services are assurance and related services that are reasonably related to the performance of the audit or review of our financial statements or that are traditionally performed by the independent registered public accounting firm. Under the Policy, the Audit Committee grants generalpre-approval for audit-related services.

Tax Services

Under the Policy, the Audit Committee may grant generalpre-approval for specific tax compliance, planning and advice services to be provided by the independent registered public accounting firm, that the Audit Committee has reviewed and believes would not impair the independence of the independent registered public accounting firm, and that are consistent with the SEC'sSEC’s rules on auditor independence. Tax services to be performed by our independent registered public accounting firm must be specifically approved by the Audit Committee.

All Other Services

Under the Policy, the Audit Committee may grantpre-approval for specific permissiblenon-audit services classified as All Other Services that it believes are routine and recurring services, would not impair the independence of the independent registered public accounting firm and are consistent with the SEC'sSEC’s rules on auditor independence. Services permissible under applicable rules but not specifically approved in the Policy require further specificpre-approval by the Audit Committee.

Procedures

Under the Policy, each year the Senior Vice President, Finance and Risk Management (our principal financial and accounting officer)Chief Financial Officer and our independent registered public accounting firm jointly submit to the Audit Committee a schedule of audit, audit-related, tax and othernon-audit services that are subject topre-approval. This schedule provides a description of each type of service that is subject topre-approval and, where possible, provides projected fees (or a range of projected fees) for each service. The Audit Committee reviews and approves the types of services and reviews the projected fees for the next fiscal year. Any changes to the fee amounts

				2019 Proxy Statement | 7

Proposal 2

listed in the schedule are subject to further specific approval of the Audit Committee. The Policy prohibits the independent registered public accounting firm from commencing any project not described in the schedule approved by the Audit Committee until specific approval has been given.

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Recommendation of the Board of Directors

The Board of Directors unanimously recommends that the stockholders vote "FOR"“FOR” Proposal 2—Ratification of the appointment of KPMG LLP as our independent registered public accounting firm for 2018.2019.

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OTHER BUSINESS
Other Business

The Board knows of no other business for consideration at the meeting. If other matters are properly presented at the meeting, or at any adjournment or postponement of the meeting, Messrs. Byrne and Johnsonthe proxy holders will vote, or otherwise act, to the extent they are legally permitted to do so, on your behalf in accordance with instructions from the Board'sBoard or the Nominating and Corporate Governance Committee (or, in the absence of instructions from the Board and the Committee, their) judgment on such matters.

THE BOARD

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Corporate Governance

General

We are committed to strong corporate governance principles. Effective governance protects the long-term interests of our stockholders, promotes public trust in the Company, and strengthens management accountability.

Corporate Social Responsibility

Our approach to corporate social responsibility is based on the foundational belief in the interconnection of our long-term business success and the strength of our communities and world. For nearly 20 years, we have partnered with nonprofit organizations to support our communities, respect the environment, and volunteer our time to those in need. A quote from Dr. Byrne on the wall of our corporate headquarters provides the mantra for our corporate responsibility work, “You do the right thing not because of how it will affect the bottom line. You do the right thing because you are the kind of person who does the right thing.”

Governance

Our commitment to corporate social responsibility is embedded in every level of the Company, and oversight rests with the Board of Directors. We have taken a number of steps to promote gender diversity on our Board and the advancement of women in leadership roles generally. For example, in May 2017, Allison Abraham was appointed as the first chairwoman of the Board, and in December 2017, we announced that we have taken the “ParityPledge” to promote the advancement of women within our organization, which includes, among other things, a commitment to interview at least one female candidate for open executive positions.

Environment

Our technology plays a critical role in transitioning to a more resource-efficient world by addressing the harmful effects of climate change, increasing business resiliency, and improving daily lives. We take environmental stewardship seriously. We strive to ensure environmental and social initiatives that go beyond our direct impact. We recognize the opportunity and importance of implementing measures to reduce our overall impact on the environment. We are eager to continue current initiatives such as recycling, conserving energy, and increasing transportation options. We are also exploring additional opportunities for emission reduction andeco-friendly innovations throughout our supply chain.

Our commitment to promoting environmental stewardship is evidenced in numerous aspects of our corporate operations, from technology development to our workspace, including the following:

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Corporate Governance General
 / Corporate Social Responsibility

Social

We demonstrate our commitment to corporate social responsibility and community involvement through our S.A.V.E program, which focuses on four important societal needs that align with our culture, products, and people: Sourcing Responsibly, Associate Development, Volunteering & Community, and Environmental Stewardship. We have also participated in the Adopt-A-Highway program and work with local law enforcement as it pertains to See Something/Say Something programs and programs associated with fire safety, active shooter, and similar community safety programs. We encourage our employees to contribute to the community by giving each employee eight hours of paid volunteer time off annually. Employees can use this time to serve the community in a number of ways, some of which have included volunteering at homeless shelters and animal shelters, sponsoring a highway cleanup, donating time to philanthropic projects, and serving on boards of various non-profit organizations.

Through Overstock Cares, our philanthropic arm, we have supported hundreds of non-profit organizations with millions of dollars’ worth of in-kind and monetary contributions. Some of these organizations include The Road Home, American Heart Association, Hope Refuge, The Inn Between, Make a Wish, Habitat for Humanity, and Operation Underground Railroad. Overstock Cares also supports three major corporate philanthropic partners: Best Friends Animal Society (BFAS), Special Operations Warrior Foundation (SOWF), and American Red Cross (ARC). We have also provided support to organizations such as these on our website, at checkout, where customers are given the opportunity to donate. One-hundred percent of customer donations made through our website are given directly to our charitable partners. Finally, we donate excess food from our on-site café at our corporate to Wasteless Solutions, a Utah-based organization committed to connecting surplus food with local non-profit organizations to help those in need and reduce food waste.

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The Board

Dash Board

Board Structure

The Board of Directors currently consists of seven members. Each of the nominees for election is a current member of the Board. The remaining fourfive directors are expected to continue to serve their terms as described below. Our directors serve staggered terms. This is accomplished as follows:

•

each director serves a three-year term,



•

The Board / Committees of the Nasdaq director independence standards except for Patrick M. Byrne, who serves as our Chief Executive Officer and in other capacities (see "Information Regarding Director Nominees and Other Directors"); Saum Noursalehi, who serves as our President, Retail, and Jonathan E. Johnson III, who serves as Overstock's President, Medici, and also serves as president of our wholly-owned subsidiary, Medici Ventures and as a member of its Board. In addition, Mr. Johnson has previously served in a number of other executive positions with the Company.Board

In reaching its determinations regarding the independence of the members of the Board, the Board considered the fact that Ms. Abraham'sAbraham’s adult son iswas an employee of the Company and is now an employee of our indirect majority-owned subsidiary tZERO, and determined that Ms. Abraham met the independence requirements. With respect to Mr. Corbus, the Board considered the facts that Mr. Corbus is currently also serving as a directorDirector of our wholly owned

The Board / Board Leadership Structure

Board Leadership Structure

Patrick M. Byrne serves as our principal executive officer and as a member of the Board of Directors. Allison H. Abraham has served as Chairwoman of the Board since 2017. We have not named a lead independent director. At December 31, 2017,2018, the Board consisted of seven directors; four of whom were independent. We believe that our leadership structure is appropriate because the size of the Board and the composition of the Board permit and encourage each member to take an active role in all discussions, and each member does actively participate in all substantive discussions. We believe that our current structure is serving the Company well at this time. Although Dr. Byrne previously served as both Chairman and Chief Executive Officer, the Board separated the roles of Chairman and Chief Executive Officer in 2014 based on its perceptions of the Company'sCompany’s best interests at the time. We do not have any procedures for deciding when to separate or combine these positions.

Board Role in Risk Oversight

The Board has delegated responsibility for oversight of risk management relating to compensation matters to the Compensation Committee. The Board has delegated responsibility for cybersecurity risks, including protection of customer and employee data, proprietary information, and cyber risks, to the Audit Committee and management. The Board has delegated responsibility for financial and other risk management to the Audit Committee, although the full Board remains involved in risk management. The Committees and the Board receive periodic reports from management regarding various aspects of the Company'sCompany’s risk management program. The manner in which the Board and Committees administer the oversight of risk management has not had any effect on the Board'sBoard’s leadership structure.

Director Qualifications

The Nominating and Corporate Governance Committee has developed the Company'sCompany’s Corporate Governance Principles ("Principles"(“Principles”), which have been adopted by the Board. The Principles set forth the Committee'sCommittee’s belief that while there are no specific minimum qualifications the Committee believes must be met by a candidate to be recommended by the Committee, candidates for election to the Board should have the highest professional and personal ethics and values. Candidates should have broad relevant experience, and should be committed to enhancing long-term stockholder value. They should be able and willing to provide insight and practical advice, and they must actively represent the interests of the stockholders. The Committee believes that a variety of types and a balance of knowledge, experience and capabilities among the members of the Board are in the best interests of the stockholders. The Principles set forth the Committee'sCommittee’s belief that diversity of viewpoint, professional experience and other individual qualities and attributes should be considered to the extent that they relate to the contribution a director is expected to make to the Board and the Company. The Committee periodically reviews the Principles, including the portion regarding diversity. The ability of a candidate to make independent analytical inquiries, the ability to understand the Company'sCompany’s business, and the willingness of a candidate to devote adequate attention and time to the duties of the Board, are all relevant to the qualifications of a candidate. The specific experience, qualifications, attributes or skills that led the Committee to the conclusion that each director should be a director in light of our business and structure are described under "Information“Information Regarding Director Nominees and Other Directors,"” below.

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Identification and Evaluation of Nominees for Director

The Nominating and Corporate Governance Committee believes that the current Board composition is serving the stockholders of the Company well. In the future, the Committee may consider additional candidates identified through current members of the Board, professional search firms, stockholders or other persons. Candidates may be evaluated at regular or special meetings of the Board, and may be considered at any point during the year.

Stockholders may propose director candidates for general consideration by the Nominating and Corporate Governance Committee by submitting in proper written form the individual'sindividual’s name, qualifications, and the other information required by the Bylaws as described below in "Other“Other Information—Procedure for Nominating Directors for Election at an Annual Meeting or a Special Meeting"Meeting” to the Secretary of the Company. The Nominating and Corporate Governance Committee will evaluate any candidates recommended by stockholders against the same criteria applicable to the evaluation of candidates proposed by directors or management.

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The Board / Communications with the Board

The Committee has not approved any nominee for inclusion on our proxy card for the 20182019 Annual Meeting other than Patrick M. Byrne, Barclay F. CorbusKirthi Kalyanam and Jonathan E. Johnson III,Joseph J. Tabacco, Jr., each of whom is a current member of the Board. We have not paid a fee to any third party or parties to identify or evaluate or assist in identifying or evaluating potential nominees. The Committee did not receive, by a date not later than the 120th calendar day before the date of the Company'sCompany’s proxy statement released to security holders in connection with the previous year'syear’s annual meeting, a recommended nominee from a security holder that beneficially owned more than 5% of the Company'sCompany’s voting common stock for at least one year as of the date the recommendation was made, or from a group of security holders that beneficially owned, in the aggregate, more than 5% of the Company'sCompany’s voting common stock, with each of the securities used to calculate that ownership held for at least one year as of the date the recommendation was made.

Communications with the Board

The Board has adopted resolutions to provide a formal process by which stockholders may communicate with the Board. The process adopted by the Board permits stockholders to communicate with the Board either in writing, addressed to the Board at the Company'sCompany’s headquarters at 799 W. Coliseum Way, Midvale, Utah 84047, or bye-mail, sent toboardofdirectors@overstock.com. All communications from stockholders regarding matters appropriate for stockholder communications with the Board and delivered as described will be delivered to one or more Board members. The determination whether a communication involves a matter appropriate for stockholder communications with the Board is made by the Chairwoman of the Board or our General Counsel. Stockholders who desire to utilize the procedures described under "Other“Other Information—Procedure for Submitting Stockholder Proposals"Proposals” or "—“—Procedure for Nominating Directors for Election at an Annual Meeting or a Special Meeting"Meeting” should read those sections and the applicable portions of our bylaws and follow the procedures described.

Annual Meeting Attendance

Our policy is that Board members should attend our annual stockholders meetings if reasonably possible. All members of the Board attended the last annual stockholders meeting, which was held in May 2017.2018.

Director Resignation Policy

Our Board has adopted a director resignation policy. The policy applies only to uncontested elections of directors. Under the policy, any incumbent nominee who fails to receive a greater number of "for"“for” votes than "withhold"“withhold” votes or instructions is required to tender his or her resignation to the

The Board / Policies and Procedures Regarding Related Party Transactions

Policies and Procedures Regarding Related Party Transactions

The Board has established a written policy and procedures for the review and approval or ratification of related party transactions. Under the Board'sBoard’s policy, any related party transaction that would be required to be disclosed pursuant to Item 404 ofRegulation S-K is subject to the prior approval of the Audit Committee unless prior approval is not feasible, in which case the transaction is required to be considered at the Audit Committee'sCommittee’s next meeting and, if the Audit Committee determines it to be appropriate, may be ratified at that meeting. In determining whether to approve or ratify a related party transaction, the Audit Committee takes into account, among other factors it deems appropriate, whether the transaction is on terms no less favorable to us than terms generally available from an unrelated person under the same or similar circumstances, and the extent of the related person'sperson’s interest in the transaction. No member of the Audit Committee may participate in any approval or ratification of a related party transaction in which such member is a related person, other than to provide the Audit Committee with all material information regarding the transaction, including information regarding the extent of the member'smember’s interest in the transaction, except that the Audit Committee may allow one or more members to participate in any approval or ratification of a related party transaction or potential related party transaction in which such member(s) is or may be a related person if the Audit Committee determines that doing so is in the best interests of the Company and its stockholders and informs the Board of Directors of any such approval. If a related party transaction will be ongoing, the Audit Committee may establish guidelines or other parameters or conditions relating to our participation in the transaction. The Audit Committee may from time to timepre-approve types or categories of transactions by related persons.

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The Board / Information Regarding Director Nominees and Other Directors

Information Regarding Director Nominees and Other Directors

Set forth below is certain information regarding the nominees for election and all other directors of Overstock whose term of office continues after the 20182019 Annual Meeting.

Class III Directors (andand Nominees for Election for Terms Expiring in 2021)
2022

Name		Age			Position with the Company		Director Since
Patrick M. Byrne			55		Chief Dr. Kirthi Kalyanam Age: 54 Director since: 2015 Committee Memberships: N/A Dr. Kirthi Kalyanam has served as a director of Overstock since February 2015. For more than the last five years, Dr. Kalyanam has worked in academia and in consulting with his primary emphasis in Internet retailing. Dr. Kalyanam is currently the L.J. Skaggs Distinguished Professor and director of the Retail Management Institute at the Leavey School of Business at Santa Clara University. He has previously served as faculty director of the Executive Officer		October 1999MBA program, a visiting professor at the Graduate School of Business at Stanford University, guest faculty in the Stanford Executive MMP program, and senior vice president and chief marketing officer of SpinCircuit Inc., a provider of supply chain integration services to the electronics industry. He received his Ph.D. in business administration from the Krannert School of Management, Purdue University. Dr. Kalyanam’s areas of expertise include Internet Marketing, Retailing, Customer Centric Retailing, Multi-Channel Marketing and Database Marketing. The specific experience, qualifications, attributes or skills that led the Board to conclude that Dr. Kalyanam should serve as a director in light of our business and structure were his extensive expertise in in retailing, Internet and multi-channel marketing and database marketing.
Barclay F. Corbus			50
		Non-Employee Director		March 2007
Jonathan E. Johnson III			52		President, Medici Ventures		May 2013 Joseph J. Tabacco, Jr Age: 70 Director since: 2007 Committee Memberships: Audit, Nominating and Corporate Governance, Compensation Mr. Joseph J. Tabacco, Jr. has served as a director of Overstock since June 2007. For more than the last five years Mr. Tabacco has served as the managing partner of the San Francisco office of Berman Tabacco. A 1974 honors graduate of George Washington University School of Law, Mr. Tabacco litigates antitrust, securities fraud, commercial high tech, and intellectual property matters. Since entering private practice in the early 1980s, Mr. Tabacco has served as trial or lead counsel in numerous antitrust and securities cases and has been involved in all aspects of state and federal litigation. Prior to 1981, Mr. Tabacco served as senior trial attorney for the U.S. Department of Justice, Antitrust Division, and in both the Central District of California and the Southern District of New York.

 Dr. Patrick M. Byrne has served as our Chief Executive Officer (principal executive officer), subject to medical leaves of absence in 2013 and 2016, and as a Director since October 1999, as Chairman of

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the Board from February 2001 through October 2005, and July 2006 through April 2014. Dr. Byrne has also served as the Chief Executive Officer of tZERO, an indirect majority-owned subsidiary of Overstock, since July 2015 and also has served as Co-chairman of the Board of Directors of tZERO since October 2017. Dr. Byrne also serves on the Board of Directors of our wholly-owned subsidiary Medici Ventures, and as Co-Chairman and Chief Executive Officer of our 50%-owned public benefit corporation subsidiary DeSoto Inc. From September 1997 to May 1999, Dr. Byrne served as President and Chief Executive Officer of Fechheimer Brothers, Inc., a manufacturer and distributor of uniforms. From 1995 until its sale in September 1999, Dr. Byrne was Chairman, President and Chief Executive Officer of Centricut, LLC, a manufacturer and distributor of industrial torch parts. From 1994 to the present, Dr. Byrne has served as a Manager of the Haverford Group, an investment company and an affiliate of Overstock. Dr. Byrne has a Bachelor of Arts degree in Chinese studies from Dartmouth College, a Master's Degree from Cambridge University as a Marshall Scholar, and a Ph.D. in philosophy from Stanford University. The specific experience, qualifications, attributes or skills that led the Board to conclude that Dr. Byrne should serve as a director in light of our business and structure were the following. Dr. Byrne has led the Company from revenues of approximately $1.8 million in 1999 to approximately $1.7 billion for the year ended December 31, 2017. He has served as our Chief Executive Officer since 1999 (subject to medical leaves of absence in 2013 and 2016), and has also been directly in charge of marketing, merchandising and other senior executive management functions from time to time. In addition to being the Company's founder, largest stockholder and Chief Executive Officer, Dr. Byrne has led and continues to lead the development of the Company's evolving business model, and he is the Company's chief long-term strategic planner.

Mr. Barclay F. Corbus has served as a Director of Overstock since March 2007. He is a member of the Audit Committee and has served on the Nominating and Corporate Governance Committee and Compensation Committee. Mr. Corbus also serves as a member of the Board of Directors of our wholly owned subsidiary Medici Ventures. Mr. Corbus has served as Senior Vice President of Clean Energy Fuels Corp., a provider of vehicular natural gas, with responsibility for strategic development, since September 2007. He served as Co-CEO of WR Hambrecht + Co., an investment banking firm, from July 2004 to September 2007, and prior to that date served in other executive positions with WR Hambrecht + Co. Prior to joining WR Hambrecht + Co. in March 1999, Mr. Corbus was in the investment banking group at Donaldson, Lufkin and Jenrette. Mr. Corbus graduated from Dartmouth College with a Bachelor of Arts Degree in Government and has a Master's Degree of Business Administration in Finance from Columbia Business School. The specific experience, qualifications, attributes or skills that led the Board to conclude that Mr. Corbus should serve as a director in light of our business and structure were his substantial experience in finance, management, and strategic planning, as well as his experience analyzing and evaluating corporate business plans, capital structures and needs, and debt, equity and hybrid financing alternatives resulting from his work for Clean Energy Fuels Corp., WR Hambrecht + Co., and Donaldson, Lufkin and Jenrette.

Mr. Jonathan E. Johnson III joined Overstock in September 2002 and has served as a Director since May 2013. Mr. Johnson currently serves as Overstock's President, Medici, and as the president of Medici Ventures, Inc. He is also on the Board of Directors of Medici Ventures and Medici Ventures' portfolio companies Bitt.com, PeerNova, Voatz, Bitsy and SettleMint. He served as our President from July 2008 to February 2013, as our Acting Chief Executive Officer from February 2013 to April 2013, as Executive Vice Chairman of the Board and Corporate Secretary from April 2013 to April 2014, and Chairman of the Board of Directors May 2014 through May 2017. Prior to his service as our President, Mr. Johnson served as our General Counsel and as our Vice President, Strategic Projects and Legal, and Senior Vice President, Corporate Affairs and Legal. Mr. Johnson previously served on the board of directors of t0.com, Inc. Mr. Johnson holds a Bachelor's Degree in Japanese from Brigham Young University, studied for a year at Osaka University of Foreign Studies in Japan, and received his law degree from the J. Reuben Clark Law School at Brigham Young University. Mr. Johnson serves on the executive committee of the Board of Trustees of the Utah Technology Council, the board of Silicon

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Slopes, the executive committee of the Board of Trustees of the Utah Foundation, the Board of Trustees of the Hale Center Theatre, and the Board of Directors of the National Museum of American Religion. The specific experience, qualifications, attributes or skills that led the Board to conclude that Mr. Johnson should serve as a director in light of our business and structure were his experience as our General Counsel, as our Vice President, Strategic Projects and Legal, as our Senior Vice President, Corporate Affairs, as our President, and as our Acting Chief Executive Officer.

Class II Directors (Terms Expiring in 2019)

Name		Age			Position with the Company		Director Since
Kirthi Kalyanam			53		Non-Employee Director		February 2015
Joseph J. Tabacco, Jr			69		Non-Employee Director		June 20072019 Proxy Statement | 17

Dr. Kirthi KalyanamThe Board has served as/ Information Regarding Director of Overstock since February 2015. He is currently the L.J. Skaggs Distinguished ProfessorNominees and Director of the Retail Management Institute at the Leavey School of Business at Santa Clara University. He has also served as Faculty Director of the Executive MBA program, a visiting Professor at the Graduate School of Business at Stanford University, a guest faculty in the Stanford Executive MMP program, and Senior Vice President and Chief Marketing Officer of SpinCircuit Inc., a provider of supply chain integration services to the electronics industry. He received his Ph.D. in business administration from the Krannert School of Management, Purdue University. His research and expertise are in retailing, Internet and multi-channel marketing, quantitative marketing and the intersection of these areas. Dr. Kalyanam performs consulting services for several companies. Dr. Kalyanam performed consulting services for Overstock in 2015, but has not provided consulting services to us since 2015. The specific experience, qualifications, attributes or skills that led the Board to conclude that Dr. Kalyanam should serve as a director in light of our business and structure were his extensive expertise in in retailing, Internet and multi-channel marketing and quantitative marketing.Other Directors

        Mr. Joseph J. Tabacco, Jr.    has served as a Director of Overstock since June 2007. He is a member of the Audit Committee and the Compensation Committee and is the Chairman of the Nominating and Corporate Governance Committee. For more than the last five years Mr. Tabacco has served as the managing partner of the San Francisco office of Berman Tabacco (formerly Berman DeValerio). A 1974 honors graduate of George Washington University School of Law, Mr. Tabacco litigates antitrust, securities fraud, commercial high tech, and intellectual property matters. Since entering private practice in the early 1980s, Mr. Tabacco has served as trial or lead counsel in numerous antitrust and securities cases and has been involved in all aspects of state and federal litigation. Prior to 1981, Mr. Tabacco served as senior trial attorney for the U.S. Department of Justice, Antitrust Division, and in both the Central District of California and the Southern District of New York. Mr. Tabacco frequently lectures and authors articles on securities and antitrust law issues and is a member of the Advisory Board of the Institute for Consumer Antitrust Studies at Loyola University Chicago School of Law. Mr. Tabacco is also a former teaching fellow of the Attorney General's Advocacy Institute in Washington, D.C., and has served on the faculty of ALI-ABA on programs about U.S.-Canadian business litigation and trial of complex securities cases. The specific experience, qualifications, attributes or skills that led the Board to conclude that Mr. Tabacco should serve as a director in light of our business and structure were his extensive experience as a practicing attorney, litigating in the fields of securities fraud, corporate governance, general business litigation and antitrust litigation, including substantial litigation on behalf of investors, including public pension funds and other institutional investors as well as individual investors, in a wide variety of cases involving publicly traded companies, as well as his familiarity with state and federal competition laws and intellectual property rights.

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Class III Directors (Terms Expiring in 2020)

				Allison H. Abraham Age: 56 Director since: 2002 Committee Memberships: Audit, Nominating and Corporate Governance, Compensation Ms. Allison H. Abraham was appointed chair of Overstock’s Board of Directors in 2017 and has served as a director of Overstock since March 2002. Ms. Abraham is the Founder and, for more than the last five years, has been the President and Director of The Newton School, a private, non-profit K-8 school located in Sterling, Virginia. Ms. Abraham managed her own consulting business from October 2001 to November 2008. Previously, Ms. Abraham served as President and as a director of LifeMinders, Inc. Prior to joining LifeMinders, Ms. Abraham served as Chief Operating Officer of iVillage Inc. and was President, Chief Operating Officer and a Director of Shoppers Express. From 1992 to 1996, Ms. Abraham held several marketing and management positions at Ameritech Corporation. She was employed at American Express Travel Related Services in New York City for four years prior to this time. Ms. Abraham holds a Bachelor of Arts Degree in Economics from Tufts University and a Master’s Degree of Business Administration from the Darden School at the University of Virginia. The specific experience, qualifications, attributes or skills that led the Board to conclude that Ms. Abraham should serve as a director in light of our business and structure were Ms. Abraham’s substantial marketing experience and experience running online marketing companies, including her marketing experience with American Express Travel Related Services, her marketing and management positions with Ameritech Corporation, her experience as Vice President of Sales and Marketing and subsequently as President, Chief Operating Officer and a director of Shoppers Express, her experience as Chief Operating Officer of iVillage Inc. and her experience as President and as a director of LifeMinders, Inc.
				Saum Noursalehi Age: 40 Director since: 2017 Committee Memberships: N/A Mr. Saum Noursalehi has served as a director of Overstock since 2017. He is the Chief Executive Officer of tZERO, our majority-owned subsidiary focusing on the development and commercialization of blockchain-based financial technology. For more than the last five years Mr. Noursalehi has served in various technical and management positions with Overstock and with tZERO. Prior to becoming Chief Executive Officer of tZERO, Mr. Noursalehi served as president of Overstock’s retail business from August 2016 to May 2018. He has been a senior vice president of Overstock since 2013. Before joining Overstock in 2005, Mr. Noursalehi worked as a software engineer at the Utah Administrative Office of the Courts, Brooks Automation, and technology startup Infopia. Mr. Noursalehi received a Bachelor’s Degree in Computer Science from the University of Utah. The specific experience, qualifications, attributes or skills that led the Board to conclude that Mr. Noursalehi should serve as a director in light of our business and structure were his combined deep expertise in our technology and marketing strategy.

 2019 Proxy Statement

	Name18		Age|			Position with the Company		Director Since

The Board / Information Regarding Director Nominees and Other Directors

Class I Directors (Terms Expiring in 2021)

Allison H. Abraham			55		Non-Employee Dr. Patrick M. Byrne Age: 56 Director since: 1999 Committee Memberships: N/A Dr. Patrick M. Byrne has served as our Chief Executive Officer (principal executive officer), and Chairwomanas a director since October 1999, as Chairman of the Board		March 2002 from February 2001 through October 2005, and from July 2006 through April 2014. Dr. Byrne has also served as the chief executive officer and/or a member or chairman orco-chairman of the board of directors of several of our wholly or majority owned subsidiaries at various times during the last five years. From 1994 to the present, Dr. Byrne has served as a Manager of the Haverford Group, an investment company and an affiliate of Overstock. Dr. Byrne controls High Plains Investments LLC, which is our largest stockholder. Dr. Byrne has a Bachelor of Arts degree in Chinese studies from Dartmouth College, a Master’s Degree from Cambridge University as a Marshall Scholar, and a Ph.D. in philosophy from Stanford University. The specific experience, qualifications, attributes or skills that led the Board to conclude that Dr. Byrne should serve as a director in light of our business and structure were the following. Dr. Byrne has led the Company from revenues of approximately $1.8 million in 1999 to approximately $1.8 billion for the year ended December 31, 2018. He has served as our Chief Executive Officer since 1999 (subject to medical leaves of absence in 2013 and 2016), and has also been directly in charge of marketing, merchandising and other senior executive management functions from time to time. Dr. Byrne has led and continues to lead the development of our evolving business model, including the initiation and development of the blockchain-based initiatives being pursued by Medici Ventures and tZERO. Dr. Byrne is our chief long-term strategic planner.
Saum Noursalehi			39
		President, Retail		May 2017
				Barclay F. Corbus Age: 51 Director since: 2007 Committee Memberships: Audit Mr. Barclay F. Corbus has served as a director of Overstock since March 2007. Mr. Corbus assists with overseeing our policies and practices that promote diversity and inclusion, health, safety, environmental, product stewardship and sustainability. Mr. Corbus has served as Senior Vice President of Clean Energy Fuels Corp., a provider of vehicular natural gas, with responsibility for strategic development, since September 2007. He served asCo-CEO of WR Hambrecht + Co., an investment banking firm, from July 2004 to September 2007, and prior to that date served in other executive positions with WR Hambrecht + Co. Prior to joining WR Hambrecht + Co in March 1999, Mr. Corbus was in the investment banking group at Donaldson, Lufkin and Jenrette. Mr. Corbus graduated from Dartmouth College with a Bachelor of Arts Degree in Government and has a Master’s Degree of Business Administration in Finance from Columbia Business School. The specific experience, qualifications, attributes or skills that led the Board to conclude that Mr. Corbus should serve as a director in light of our business and structure were his substantial experience in finance, management, and strategic planning, as well as his experience analyzing and evaluating corporate business plans, capital structures and needs, and debt, equity and hybrid financing alternatives resulting from his work for Clean Energy Fuels Corp., WR Hambrecht + Co., and Donaldson, Lufkin and Jenrette.

				2019 Proxy Statement | 19

Ms. Allison H. AbrahamThe Board has served as a/ Information Regarding Director of Overstock since March 2002Nominees and was appointed Chairwoman in May 2017. She is currently the President and Founder of The Newton School, a private, non-profit elementary and middle school located in Sterling, Virginia. She is a member of the Compensation Committee and Nominating and Corporate Governance Committee and is the Chair of the Audit Committee. Ms. Abraham managed her own consulting business from October 2001 to November 2008. Previously, Ms. Abraham served as President and as a director of LifeMinders, Inc. from May 2000 until October 2001. Prior to joining LifeMinders, Ms. Abraham served as Chief Operating Officer of iVillage Inc. from May 1998 to May 2000. From February 1997 to April 1998, Ms. Abraham was President, Chief Operating Officer and a Director of Shoppers Express. From 1992 to 1996, Ms. Abraham held several marketing and management positions at Ameritech Corporation. She was employed at American Express Travel Related Services in New York City from 1988 to 1992. Ms. Abraham holds a Bachelor of Arts Degree in Economics from Tufts University and a Master's Degree of Business Administration from the Darden School at the University of Virginia. The specific experience, qualifications, attributes or skills that led the Board to conclude that Ms. Abraham should serve as a director in light of our business and structure were Ms. Abraham's substantial marketing experience and experience running online marketing companies, including her marketing experience with American Express Travel Related Services, her marketing and management positions with Ameritech Corporation, her experience as Vice President of Sales and Marketing and subsequently as President, Chief Operating Officer and a director of Shoppers Express, her experience as Chief Operating Officer of iVillage Inc., and her experience as President and as a director of LifeMinders, Inc.Other Directors

 Mr. Saum Noursalehi has served as a Director of Overstock since May 2017 and as our President, Retail since August 2016. He previously served as our chief revenue officer and as a senior vice president. Prior to his appointment as senior vice president in 2013, Mr. Noursalehi served as vice president of OLabs and held roles in website, mobile and search engine optimization. He was responsible for the creation of several core technologies for Overstock, including in-house search and recommendation engines, product sort algorithms, and a vendor application designed to optimize product content. He also spearheaded the implementation of automated email campaigns based on customer behavior. Additionally, he led a full redesign of both the desktop and mobile websites, and oversaw the development of Overstock's mobile apps, which have won five consecutive Mobile Web Awards for Best Retail App from the Web Marketing Association. Mr. Noursalehi joined Overstock in 2005 as a software engineer. Before joining Overstock, Noursalehi worked at the Utah Administrative Office of the Courts, Brooks Automation, and technology startup Infopia. Mr. Noursalehi received a Bachelor's Degree in Computer Science from the University of Utah, has been profiled in publications such as Wired, and was a recipient of the 2015 Utah Business Forty Under 40 award honoring Utah's top up-and-coming professionals. The specific experience, qualifications, attributes or skills that led the Board to conclude that Mr. Noursalehi should serve as a director in light of our business and structure were his combined deep expertise in our technology and marketing strategy.

				Jonathan E. Johnson III Age: 53 Director since: 2013 Committee Memberships: N/A Mr. Jonathan E. Johnson III joined Overstock in September 2002 and has served as a Director since May 2013. Mr. Johnson currently serves as President, Medici Ventures. He is also on the Board of Directors of Medici Ventures and Medici Ventures portfolio companies Bitt.com, Finclusive, GrainChain, PeerNova, and Voatz. He served as our President from July 2008 to February 2013, as our Acting Chief Executive Officer from February 2013 to April 2013, as Executive Vice Chairman of the Board and Corporate Secretary from April 2013 to April 2014, and Chairman of the Board of Directors May 2014 through May 2017. Prior to his service as our President, Mr. Johnson served as our General Counsel and as our Vice President, Strategic Projects and Legal, and Senior Vice President, Corporate Affairs and Legal. Mr. Johnson previously served on the Board of Directors of t0.com, Inc. Mr. Johnson holds a Bachelor’s Degree in Japanese from Brigham Young University, studied for a year at Osaka University of Foreign Studies in Japan, and received his law degree from the J. Reuben Clark Law School at Brigham Young University. Mr. Johnson serves on the executive committee of the Board of Trustees of the Utah Technology Council, the Board of Silicon Slopes, the Board of Trustees of the Libertas Institute, and the Board of Trustees of the Hale Center Theatre. The specific experience, qualifications, attributes or skills that led the Board to conclude that Mr. Johnson should serve as a director in light of our business and structure were his experience as our General Counsel, as our Vice President, Strategic Projects and Legal, as our Senior Vice President, Corporate Affairs, as our President, and as our Acting Chief Executive Officer.

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COMPENSATION DISCUSSION AND ANALYSIS
Executive Compensation

Introduction
Compensation Discussion and Analysis

Introduction

The Compensation Committee administers our executive compensation program. The Compensation Committee, which consists entirely of independent directors, is responsible for reviewing and approving our compensation policies, for reviewing and approving all forms of compensation for our executive officers, including our named executive officers identified in the Summary Compensation Table below (the "Named“Named Executive Officers"Officers”), for administering our incentive compensation programs, for approving and overseeing the administration of our employee benefits programs other than medical benefits programs, and for providing insight and guidance to management with respect to employee compensation and retention generally. Following is a discussion of the objectives and implementation of our executive compensation programs.

The Compensation Committee operates under a charter adopted by the Board of Directors. The Compensation Committee periodically reviews the adequacy of its charter and recommends changes to the Board for approval as it considers appropriate. The Compensation Committee meets at scheduled times during the year and also acts from time to time by written consent. The Compensation Committee reports on its activities and makes recommendations at meetings of the Board. The Compensation Committee reviews comparative executive compensation information from other public companies, approves executive salaries, approves awards under incentive/bonus plans, and administers the Company'sCompany’s 2005 Equity Incentive Plan. The Compensation Committee periodically reviews comparative executive compensation information from other public companies. Additionally, from time to time, the Compensation Committee reviews other human resource issues, including qualified andnon-qualified benefits and management performance appraisals and succession planning. During 2017,2018, our Chief Executive Officer (Dr. Byrne) (our "CEO"“CEO”), our President, Retail, our President, Medici Ventures, our Senior Vice President, Finance and Risk Management, our Senior Vice President, People and Customer Care, our Senior Vice President, Technology and People Care,Chief Financial Officers and other executive officers made recommendations and participated in compensation discussions concerning executive officers. The Compensation Committee does not have the power to delegate any of its authority to any other person. Our CEO does not participate in any Compensation Committee deliberations regarding his compensation, but, as he has done for the last fewseveral years, informed the Committee prior to its deliberations that he would not accept any bonus payment and would not accept a salary of more than approximately $100,000.

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Executive Compensation / Compensation Discussion and Analysis

2018 Individual Bonus Payments.In 2018 our Named Executive Officers except Messrs. Noursalehi and Johnson, whose salaries were increased from $350,000 to $400,000 and $321,500 to $350,000, respectively, because of the Compensation Committee's subjective views of their value to the Company.

        2017 Bonus Payments.    None of the Named Executive Officers werenot eligible to participate in the Overstock 2017any bonus plan. In January 2018 we paid Mr. Hughes received a $15,000cash bonus of $5,769, an amount equal to one week of pay, for his work related to 2017tZERO, and an award for his individual efforts10 years of service to the Company of a $250 gift card and performance, and in January 2018 Medici Ventures paida $1,000 cash payment with a taxgross-up payment of $529. Mr. JohnsonRaghavan received a bonus of $33,760, paid in bitcoin, as part$15,000 for having completed one year of a bonus pool.service.

2005 Equity Incentive Plan.    We use the grant of awards under our 2005 Equity Incentive Plan to provide long-term incentive compensation opportunities to our key employees, including the Named Executive Officers. The plan was most recently reapproved by the stockholders in 2017. It provides for the grant of equity-based awards, including qualified and non-qualified stock options to purchase shares of our common stock. Options granted under the plan were granted at a per share exercise price which was not less than 100% of the fair market value of the underlying shares on the date that the option was granted. Accordingly, options granted under the plan had no intrinsic value unless the market price of

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our common stock increased after the date of grant. We have not granted any options since 2008 and none remain outstanding.

        The plan also provides for the grant of restricted stock awards and other types ofrestricted stock unit awards. The plan is designed to provide incentive compensation that aligns management'smanagement’s financial interests with those of our stockholders and encourages management ownership of our common stock. Beginning in

Since 2008 the Compensation Committee has approved annual grantsonly type of RSUsaward we have granted under the plan.2005 Equity Incentive Plan has been restricted stock units (“RSUs”). The Compensation Committee determines the number of RSUs to be granted to key employees, including Named Executive Officers, based on a recommendation of management including the active participation during 20172018 of the CEO, by determining the aggregate amount the Compensation Committee considers appropriate for the entire group and allocating the awards on the basis of management'smanagement’s recommendation and the Compensation Committee'sCommittee’s subjective views of the relative ability of key employees or groups of key employees to make positive contributions to the Company. WeThe Compensation Committee generally makemakes equity grants to key employees, including Named Executive Officers, annually at a regularly scheduled Compensation Committee meeting typically held in late January or early February of each year. In 2017, we2018, the Compensation Committee made these regular equity grants in early February.on January 26, 2018. In addition, the Compensation Committee approved an RSU grant on May 8, 2018, to our new Chief Financial Officer, Mr. Iverson, who was hired on April 2, 2018. We have not otherwise adopted any specific policy regarding the amount or timing of any stock-based compensation for employees under the plan,2005 Equity Incentive Plan, although the aggregate amount of the equity grants to employees in recent years has generally been a number of shares approximately equal to1-2% of the number of shares outstanding, and the annual grant typically occurs during the first half of the year. We have never backdated or repriced options or any other equity award. The aggregate grant date fair value of equity-based awards is set forth in the Summary Compensation Table. Information concerning the number of options and RSUs held by each Named Executive Officer as of December 31, 20172018, under the 2005 Equity Incentive Plan is set forth in the Outstanding Equity Awards at FiscalYear-End Table. The annual RSU grants to our Named Executive Officers arehave historically been the most significant incentive compensation arrangement we utilize. As described below, Medici Ventures and tZERO have also begun utilizing equity incentive plans.

Medici Option Plan.    In July 2017 our wholly-owned subsidiary Medici Ventures, Inc. adopted the Medici Option Plan, which provides for the grant with respect to Medici Ventures common stock of non-qualified stock options. During 2018 the only Named Executive Officer to receive an award under this plan was Dr. Byrne, who received a non-qualified stock option with a grant date fair value of $25,593 to acquire up to 300 shares of Medici Ventures common stock.

tZERO Group, Inc. 2017 Equity Incentive Plan.

In December 2017, our indirect majority-owned subsidiary tZERO adopted an equity incentive plan which provides for the grant with respect to tZERO common stock of non-qualified stock options, restricted stock and RSUs (“tZERO Plan”). During 2018, tZERO granted non-qualified stock options to the following Named Executive Officers:

Mr. Noursalehi received an option with a grant date fair value of $1,610,868 to acquire up to 2,000,000 shares of tZERO common stock.

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Executive Compensation / Compensation Discussion and Analysis

401(k) Plan.    We maintain a 401(k) plan, in which Named Executive Officers may participate. During 20172018 we made 100% matching contributions on the first 6% of eligible compensation deferred by employees. Such matching amounts vested immediately. We did not make any profit sharing contributions in 2017.2018. The amounts of the matching contributions to our Named Executive Officers are included in the "All“All Other Compensation"Compensation” column of the Summary Compensation Table. Participation in the 401(k) plan is available to employees on anon-discriminatory basis.

Health and Welfare Benefits.    We provide health, life and disability insurance and other employee benefits programs to our employees, including our Named Executive Officers. We also provide supplemental disability insurance for our senior management team members, including the Named Executive Officers. Except for the supplemental disability insurance, our employee benefits plans are provided on anon-discriminatory basis. The amounts of the supplemental disability insurance premium payments we make for the benefit of our Named Executive Officers are included in the "All“All Other Compensation"Compensation” column of the Summary Compensation Table.

Nonqualified Deferred Compensation Plan.    We have a nonqualified deferred compensation plan for senior management (the "Deferred“Deferred Compensation Plan"Plan”). The Deferred Compensation Plan, which is described in more detail below, allows participants to defer receipt of compensation otherwise payable to them under our existing compensation plans, and also permits us to make discretionary contributions to participants'participants’ accounts. We have never made any discretionary contributions to participants'participants’ accounts. At December 31, 20172018 none of our Named Executive Officers had any funds inamounts deferred under the Deferred Compensation Plan.

Company Cafeteria.    We operate a subsidized cafeteria in our corporate headquarters. The cafeteria is open to all employees on anon-discretionary basis. We track purchases by each employee in order to compute imputed income for each employee, including Named Executive Officers.

Service Awards.    We pay service awards to all employees, including Named Executive Officers, for reaching certain milestones for their years of service. Although these awards are primarily ceremonial, we believe that loyalty to the Company and length of service deserve recognition. We therefore provide the following employee service awards:

Executive Officers to receive a bonus related to 2017 were Mr. Hughes, who received a $15,000 bonus for individual effortsCompensation / Compensation Discussion and performance, and Mr. Johnson, who received a bonus as a participant in a Medici Ventures bonus pool.Analysis

January 2018 grants the Compensation Committee considered the substantial increase in the price of the Company’s common stock during 2017 and January 2018, as well as the historical volatility of the price of the Company’s common stock, and determined that it was in the Company’s best interest to keep the aggregate amount of the grants reasonably consistent with prior years.

The Compensation Committee sometimes approves individual bonus payments as rewards for extraordinary efforts. The bonus payments to our NEOs during 2018 are described above under “2018 Bonus Payments.”

We provide the 401(k) plan, the health and welfare benefits and the Company cafeteria to help make our overall compensation packages and work environment more attractive to all our employees, including our Named Executive Officers.

Risks of Our Compensation Policies and Practices.    We periodically analyze and evaluate risks arising from our compensation policies and practices, and have concluded that our compensation policies and practices are not reasonably likely to have a material adverse effect on us.

Nonqualified Deferred Compensation Plan

We have a nonqualified deferred compensation plan for senior management (the "Deferred“Deferred Compensation Plan"Plan”). The Deferred Compensation Plan allows participants to defer receipt of compensation otherwise payable to them under our existing compensation plans, and also permits us to make discretionary contributions to participants'participants’ accounts. Participants are permitted to select from a limited number of investment alternatives available under the Plan. Under the terms of the Deferred Compensation Plan, eligible members of senior management, including the Named Executive Officers, may defer receipt of their compensation, including up to 50% of their salaries and up to 90% of their bonuses. We may, though we have no obligation to, make discretionary contributions on behalf of a participant in the Deferred Compensation Plan, in such form and amount as we deem appropriate. To

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date, we have not made any contributions to the Deferred Compensation Plan on behalf of any Named Executive Officer. We have never paid any above-market or preferential earnings on any compensation deferred under the Deferred Compensation Plan. At December 31, 20172018 none of our Named Executive Officers had any funds in the Deferred Compensation Plan.

Executive Compensation Action Taken AfterYear-End

The Compensation Committee did not take any action relating to 20172018 compensation of any Named Executive Officer after December 31, 2017, except to approve the $15,000 bonus to Mr. Hughes and the $33,760 bonus to Mr. Johnson. In early 20182018.

On February 13, 2019, the Compensation Committee met to set 20182019 salaries for our Named Executive Officers and made RSU grants as shown below. Thegrants.The Compensation Committee didhas not approveapproved any 20182019 bonus plan forin which our Named Executive Officers.

Name and Title		2018 Salary			Restricted Stock Unit Grant(1)
Patrick M. Byrne		$	100,000			0
Robert P. Hughes		$	300,000			20,000
Saum Noursalehi		$	500,000			30,000
Vidya Jwala		$	400,000			15,000
Jonathan E. Johnson III		$	350,000			5,000

---

(1)

Restricted stock unit grants are made pursuantOfficers would be eligible to the Company's 2005 Equity Incentive Plan and will vest in three equal annual increments after the January 26, 2018 grant date. Figures shownparticipate. Below are the number of units/shares.

2019 salaries and RSU grants provided to our Names Executive Officers.

Name		2019 Salary				Restricted Stock Unit Grant (1)
Patrick M. Byrne (2)		$	100,000			0
Gregory J. Iverson		$	400,000			20,000
Robert P. Hughes		$	200,000			0
Saum Noursalehi		$	1,000,000			0
Amit Goyal		$	400,000			0
John Paul Knab		$	400,000			20,000
Vikram Raghavan (3)		$	—			—

(1)	Restricted stock unit grants are made pursuant to the Company’s 2005 Equity Incentive Plan and will vest in three equal annual increments after the February 13, 2019 grant date. Figures shown are the number of units/shares.

(2)	Dr. Byrne also received a non-qualified stock option on February 13, 2019 with a grant date fair value of $86,840 to acquire up to 1,000 shares of Medici Ventures common stock.

(3)	Mr. Raghavan resigned on September 15, 2018, at which time he forfeited his unvested equity awards.

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Executive Compensation / Compensation Discussion and Analysis

Timing of Equity Awards

        WeThe Compensation Committee did not grant any stock options under the 2005 Equity Incentive Plan to any of our Named Executive Officers during 2017.2018. We do not have any program, plan or practice to time option grants, RSU awards or any other equity awards to our Named Executive Officers or to any other employee in coordination with the release of materialnon-public information. The Company'sCompany’s Board of Directors and Board committees, including the Compensation Committee, normally schedule their regular meetings at least a year in advance. Meetings of the Compensation Committee are generally held in connection with the regularly scheduled Board meetings. The meetings are scheduled in an effort to meet a number of different timing objectives, including the review of financial results and the review of press releases and filings containing financial results. The Compensation Committee may approve equity awards shortly before or after the public release of financial results or other material information, because the Compensation Committee holds its meetings in connection with the Board meetings, not because of a program, plan or practice to time option grants or other equity awards. We also do not set the grant date of any equity awards to new executives in coordination with the release of materialnon-public information, and we have not timed, and do not plan to time, the release of materialnon-public information for the purpose of affecting the value of executive compensation.

During 2018, Medici Ventures granted non-qualified stock options under the Medici Option Plan to certain of its employees and directors, including Dr. Byrne. The discussion in the paragraph above regarding the timing of meetings and other logistics regarding the 2005 Equity Incentive Plan is also generally applicable to the activities of the Medici Ventures Board relating to the Medici Option Plan.

During 2018, tZERO granted non-qualified stock options under the tZERO Plan to certain of its employees and directors, including Mr. Noursalehi, Mr. Goyal and Mr. Raghavan. Mr. Raghavan forfeited his unvested equity awards when he resigned from tZERO on or about September 15, 2018. The discussion in the second preceding paragraph above regarding the timing of meetings and other logistics regarding the 2005 Equity Incentive Plan is also generally applicable to the activities of the tZERO Board relating to the tZERO Plan.

Severance and Change of Control Arrangements

None of our executive officers has any contractual right to any severance or change of control payments under any employment or severance agreement although we do sometimes make severance payments. payments on a case-by-case basis.

Our executive officers hold RSUs issued under our 2005 Equity Incentive Plan, and the vesting of such awards may be accelerated, under certain circumstances, upon or in connection with a change of control of the Company or upon the termination of the employment of the holder within a period of time after a change of control has occurred. The 2005 Equity Incentive Plan provides that if a merger or change of control (as defined in the plan) occurs, outstanding awards will be assumed by the successor or an equivalent award will be substituted, or the award will vest and the participant will

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have the right to exercise the award. The 2005 Equity Incentive Plan also provides that the Board has the power to modify any outstanding awards at any time, by accelerating vesting or otherwise.

In addition, as described above, our Deferred Compensation Plan allows participants to defer receipt of compensation otherwise payable to them under our existing compensation plans, and permits us to make discretionary contributions to participants'participants’ accounts. Participants are fully vested in all amounts deferred and any earnings or losses on those deferrals at all times. Upon termination of service due to retirement, disability or death, a participant becomes fully vested in any additional amounts, including any discretionary contributions we make, credited to his or her account. To date, we have not made any contributions to the Deferred Compensation Plan on behalf of any Named Executive Officer, and at December 31, 20172018 none of our Named Executive Officers had any funds in the Deferred Compensation Plan.

Certain of our executive officers hold options granted under the Medici Option Plan, and the vesting and exercisability of such options may be accelerated in connection with a change of control (as defined in the Medici Option Plan) or otherwise.

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Executive Compensation / Compensation Discussion and Analysis

Certain of our executive officers hold options or other awards granted under the tZERO Plan. The tZERO Plan provides that in the event of a change of control (as defined in the tZERO Plan),the administrator shall accelerate, vest or cause the restrictions to lapse with respect to all awards outstanding under the plan prior to the change in control.

Security Ownership Requirements

We do not have any policy requiring our Named Executive Officers or directors to own any specified amount of our common stock. OurAt March 12, 2019 our CEO beneficially ownsowned approximately 23.0%14.4% of our common stock.

Hedging Policy

We have a policy prohibiting directors, officers and other employees and members of their immediate families from engaging in short sales of our stock or otherwise engaging in any transaction intended to hedge against or profit from any decrease in the market value of our securities.

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Executive Compensation / Compensation Committee Report

COMPENSATION COMMITTEE REPORT
Compensation Committee Report

The Compensation Committee has reviewed the Compensation Discussion and Analysis and discussed it with management. Based on its review and discussions with management, the Compensation Committee recommended to our Board of Directors that the Compensation Discussion and Analysis be included in the Company's 2018Company’s 2019 proxy statement and in the Company'sCompany’s Annual Report onForm 10-K for the year ended December 31, 2017.2018.

Joseph J. Tabacco, Jr. (Chair)

Allison H. Abraham

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