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Overstock.com, Inc.

799 West Coliseum Way

Midvale, Utah 84047

January 10, 2019

VIA EDGAR

Division of Corporation Finance

U.S. Securities and Exchange Commission

100 F Street, NE

Washington, DC 20549-7010

Attn: Mara Ransom, Assistant Director

Re:

 Overstock.com, Inc.
Form 10-K for the Fiscal Year Ended December 31, 2017
Filed March 15, 2018

File No. 000-49799

Ladies and Gentlemen:

Overstock.com, Inc. (the "Company," "we", "us", or "our"), is submitting this letter in response to the written comments of the staff of the Division of Corporation Finance (the "Staff") of the U.S. Securities and Exchange Commission (the "Commission") contained in your letter dated December 26, 2018, with respect to the Company's Form 10-K for the Fiscal Year Ended December 31, 2017 filed with the Commission on March 15, 2018, File No. 000-49799. As used herein, "tZERO" shall refer to tZERO Group, Inc. (formerly tZERO.com, Inc.), which is a majority-owned subsidiary of the Company.

For ease of reference, we have reproduced below in bold-faced type the comments of the Staff contained in that letter followed by the Company's response to each comment in plain type.

Form 10-K For the Fiscal Year ended December 31, 2017

General

1.

 We note your disclosure on page 37 of your Form 10-K that "tZERO expects to develop a new trading platform for the tZERO Security Tokens it plans to issue in connection with its security token offering and for use by other companies that issue tokens treated as securities, but it is only in the preliminary stages of development of the new trading platform," and your disclosure on page 40 that "tZERO is only in the preliminary stages of development of the Token Trading System and may not successfully develop, market and launch any Token Trading System." We also note the disclosure in your Form 10-Q for the period ended June 30, 2018 that "tZERO has recently entered into a joint venture with BOX Digital Market LLC to develop a national securities exchange with regulatory approvals that would enable the exchange to trade security tokens." As of your most recent Form 10-Q for the period ended September 30, 2018, it appeared that the trading platform for tZERO Security Tokens, any token trading system, and the national securities exchange for tokens were in the preliminary stages of development. However, in your Form 8-K filed December 17, your letter to shareholders indicates that "you are wrapping up development of the security token trading platform in the next couple of weeks, and, subject to finalizing regulatory review, plan to unveil it to the world early in the new year." Please tell us the status of any token trading platform or system, including a detailed discussion of the platform's stage of development, any required regulatory approvals or registrations and clarify the date(s) by which you expect any platforms to be operational and for what purpose(s). Please do the same with respect to your plans for the national securities exchange to trade security tokens.

Background

As noted in the Company's Form 10-Q for the period ended September 30, 2018 (the "Third Quarter 10-Q") "[a]n important part of tZERO's strategy is to buy, build, or partner with other entities in order to aggregate all the necessary components to have end-to-end ownership of the first fully regulated security token trading, clearing and settlement platform." (emphasis added). tZERO is pursuing at least two distinct aspects of this strategy:

•

 The "Token Trading System" - the development of a platform to facilitate the private trading by accredited investors of the tZERO Security Tokens and other tokens or coins that are determined to be securities for purposes of U.S. securities laws on the alternative trading system (the "PRO Securities ATS") operated by its subsidiary, PRO Securities, LLC ("PRO Securities"), which is further described under "The PRO Securities ATS Platform" below; and

•

 A broader strategy to develop the first U.S. national securities exchange (the "National Securities Exchange"), which it is pursuing through its joint venture with BOX Digital and which is further described under the caption "The BOX Digital JV" below.

As described below, the Company has provided appropriate updates regarding progress on this security token trading, clearing and settlement platform (including the Token Trading System and the National Securities Exchange) in its filings made under the Securities Exchange Act of 1934 (the "1934 Act") since the filing of the Form 10-K for the fiscal year ended December 31, 2017 (the "2017 10-K"). We note that the Company has not disclosed in any Form 10-Q for any of the three quarters in fiscal year 2018 (following the filing of the 2017 10-K in March 2018) that it is in the "preliminary stages" of developing the Token Trading System. Accordingly, we disagree with the Staff's statement in the comment that "[a]s of your most recent Form 10-Q for the period ended September 30, 2018, it appeared that the trading platform for tZERO Security Tokens, any token trading system, and the national securities exchange for tokens were in the preliminary stages of development." We note that the statement the Staff describes in the Company's Form 8-K filed December 17, 2018 relates to the more limited "Token Trading System" (the PRO Securities ATS platform described below), and not to the fuller strategic goal of developing the National Securities Exchange through the BOX Digital joint venture.

The PRO Securities ATS Platform

As of the date of this letter, tZERO, along with its affiliate, PRO Securities and its various business partners (all SEC-registered broker-dealers and FINRA members, each of whom licenses tZERO technology and software), is in the final stages of development of a trading environment, or platform, that will enable holders of the tZERO Preferred Equity Tokens ("Tokens") to resell their Tokens in transactions to other accredited investors exempt from registration under the Securities Act of 1933 (the "1933 Act") pursuant to the exemption from registration provided by Section 4(a)(7) of the 1933 Act. This platform is the "Token Trading System" and is not a stand-alone entity or website, but rather is a system that links the various registered entities (including PRO Securities, an introducing broker, and a clearing and custodial broker), as well as the issuer's transfer agent, required to effect trades in Tokens. As a result of the combination of (1) the smart contract design in the Tokens using the licensed tZERO technology, (2) the structure of the platform and (3) the roles of the various participants, all trades by design will satisfy the statutory requirements of Section 4(a)(7), thus effectively enforcing all restrictions related to secondary trading (as required under Regulation D and Regulation S).

tZERO expects the Token Trading System to be operational for trading the Tokens shortly following the expiration of 90-day period following the issuance of the Tokens. On October 12, 2018, tZERO issued the Tokens in settlement of the Simple Agreement for Future Equity ("SAFE") which are subject to a 90-day trading lock-up period in order to comply with Section 4(a)(7)), which expires on January 10, 2019. tZERO ultimately intends to scale the tZERO technology and software to allow the platform to enable holders of other issuers' security tokens or digital assets to be resold in transactions exempt from registration under the 1933 Act.

Initial 10-K disclosure. As noted in the Company's 2017 10-K, tZERO has been working in recent years to leverage its experience and expertise from developing and maintaining a trading platform for the trading of the Company's Series A preferred stock, in order to develop a platform that would also be capable of trading the Tokens and other tokens or coins that are determined to be securities for purposes of U.S. securities laws. This was referred to in the 2017 10-K as the "Token Trading System." The 2017 10-K disclosure noted that the Token Trading System "may be developed as an additional functionality of the PRO Securities ATS, as a functionality of another U.S. alternative trading system or a U.S. exchange that tZERO operates or designates, as a functionality of a non-U.S. trading system or a non-U.S. exchange that tZERO may operate or designate, or any other format, wherever situated." As indicated in the Staff's comment, the 2017 10-K disclosed that at the date of its filing, tZERO was only in the preliminary stages of development of the Token Trading System and that the complex technological considerations and numerous legal and regulatory issues implicated by the system would be likely addressed in consultation with tZERO's broker‑dealer subsidiaries' regulators, in particular FINRA and the SEC.

Subsequent updates. On May 10, 2018, the Company filed a Form 8-K (the "May 10 8-K") announcing the appointment of Saum Noursalehi as Chief Executive Officer of tZERO, concurrently with Mr. Noursalehi's resignation from his position as President, Retail, of the Company and Patrick Byrne's resignation from his position as Chief Executive Officer of tZERO. As noted in the May 10 8-K, this represented a significant investment of resources by the Company in the development of the tZERO platform in order to accelerate the platform's development.

In addition, the Company filed a Form 8-K on May 22, 2018 (the "May 22 8-K"), to furnish a copy of a Supplement dated May 22, 2018 (the "Supplement") to tZERO's Confidential Private Placement Offering Memorandum, as Amended, Supplemented and Restated as of March 1, 2018 (the "Offering Memorandum"). In addition to noting the management changes described above, the Supplement contained an update on the development of the Token Trading System, noting that "[o]ver the last several months, we have achieved significant progress toward tZERO's goal of an operating trading platform for tokens and coins (including the [tZERO Security Tokens]) that are determined to be securities for purposes of the U.S. securities laws." The Supplement set forth further details about the technical aspects of the platform development at that point.

In addition to the foregoing, in the Third Quarter 10-Q (filed on November 9, 2018), the Company included a subsection in its MD&A entitled "Recent tZERO Business Developments" in which, in addition to the overall strategy statement noted above, the Company disclosed that tZERO had determined not to move forward with certain previously disclosed relationships related to the platform, but that it began evaluating alternative strategic relationships that may replace one or more roles tZERO expected one of those parties to fulfill during the third quarter, and, while it had identified suitable candidates to perform these roles, tZERO had not yet entered into definitive agreements with those parties. The result of those discussions is the restricted platform described above that enables the private trading of the Tokens in a manner compliant with Section 4(a)(7) described in detail above.

Regulatory Status. Subsequent to the filing of the Third Quarter 10-Q, representatives of tZERO, PRO Securities, as operator of PRO Securities ATS, the introducing broker, the clearing and custodial broker, and tZERO, as issuer, met with FINRA representatives on November 27, 2018 and recently submitted written responses to follow-up inquiries from FINRA following that meeting. Moreover, the introducing broker and the clearing and custodial broker filed their fully disclosed clearing agreement with FINRA and expect to receive approval shortly. The introducing broker will not begin the process of onboarding Token holders and potential Token purchasers until FINRA has approved the clearing agreement.

In addition, on December 14, 2018 PRO Securities filed an amendment to its Form ATS with the Division of Trading and Markets of the SEC to describe the changes to its operations as a result of the implementation of the Token Trading System platform, including the addition of the introducing broker as a subscriber to the PRO Securities ATS. The 20-day advance notice period prior to implementing the changes considered material changes to the operation of the PRO Securities ATS ended on January 3, 2019, with no further comment from the SEC Staff.

Except as described above, no further regulatory approvals or registrations are necessary in order for the above-described trading platform to begin facilitating private resales under Section 4(a)(7).

The BOX Digital JV

As referenced in the Staff's comment, separately from the above-described Section 4(a)(7) Token Trading System, the Supplement filed on May 22, 2018 also set forth a discussion of the proposed joint venture with BOX Digital Markets LLC ("BOX Digital") to form and operate a proposed joint venture to list and publicly trade security tokens for companies that issue, or convert existing stock to, security tokens. Subsequent to that, the Company publicly announced on June 19, and disclosed in its Form 10-Q for the period ended June 30, 2018, that tZERO and BOX Digital had entered into a joint venture for the purpose of developing the National Securities Exchange with regulatory approvals that would enable the National Securities Exchange to trade security tokens. Such trading will occur through a facility of BOX known as TokynX LLC ("TokynX"). As a facility of BOX, TokynX's operations will be subject to applicable requirements in Sections 6 and 19 of the 1934 Act, among other applicable rules and regulations.

Pursuant to the operating agreement for TokynX, tZERO will provide the technology required to create and operate the National Securities Exchange and will manage the ongoing technology implementation, administration, maintenance and support, while BOX will provide executive leadership and regulatory expertise to TokynX. As noted in the Company's prior disclosures, following execution of definitive documentation, the joint venture would seek SEC approval and the joint venture would terminate if regulatory approval is not obtained. The Company has been informed that the TokynX leadership continues to work with the Staff of the Division of Trading and Markets and anticipates regulatory approval in mid-2019.

We note that the Company's next upcoming Form 10-K for fiscal year 2018 will further describe the various components of the overall tZERO platform in a manner consistent with prior disclosures and this comment response. In particular, the Company plans to provide a more detailed update of the business and regulatory status of the Token Trading System (Pro Securities ATS) and the joint venture with BOX Digital, as well as any other relevant updates.

Note 2. Accounting Policies

Noncontrolling interests, page 110

2.

 We note that tZERO launched a security token offering of the right to acquire, if issued in the future, tZERO Preferred Equity Tokens through a Simple Agreement for Future Equity ("SAFE"). Please tell us how you determined that the SAFE qualified as an equity classified financial instrument presented within noncontrolling interest. Also tell us and disclose in future filings the pertinent rights and privileges of the SAFE and, if known, Preferred Equity Tokens and how you determine the profit or loss attributable to the noncontrolling interest. See ASC 505-10-50-3.

The following analysis is based on the terms of the tZERO security token offering (the "Offering") that was launched on December 18, 2017 by which investors purchased the right to acquire Tokens through a SAFE. Please refer to tZERO's Supplement and Offering Memorandum, which as noted above was filed by the Company with its May 22 8-K, for a complete list of terms and conditions.

Applicable Guidance

In performing our analysis of the SAFE instrument, we considered the following authoritative accounting literature from