December 20, 2019

Jonathan E. Johnson
Chief Executive Officer
Overstock.com, Inc.
799 W. Coliseum Way
Midvale, Utah 84047

       Re: Overstock.com, Inc.
           Amendment No. 1 to
           Preliminary Proxy Statement on Schedule 14A
           Filed December 16, 2019
           File No. 000-49799

Dear Mr. Johnson:

       We have reviewed your filing and have the following comments. In some of
our
comments, we may ask you to provide us with information so we may better
understand your
disclosure.

       Please respond to these comments within ten business days by providing
the requested
information or advise us as soon as possible when you will respond. If you do
not believe our
comments apply to your facts and circumstances, please tell us why in your
response.

       After reviewing your response to these comments, we may have additional
comments.

Amendment No. 1 to Preliminary Proxy Statement on Schedule 14A filed December
16, 2019

Background to the Special Meeting of Stockholders, page 3

1.    We note your response to comment 2. With a view to informing
shareholders'
      understanding of the purpose of the Dividend, please provide as
disclosure in your
      filing your explanation as to how the Dividend will "help the Company
achieve its
      strategic goals with blockchain technology."
Overstock Announces Registration of Dividend, page 3

2.    We note your response to comment 4, but your amended disclosure is not
fully responsive
      to our comment. In our view, the company is required to register the
offer and sale of the
      Dividend because it is a disposition of securities for value. As a result
of such
      registration, the shares will be freely transferable in the hands on
non-affiliates, which
      may provide greater liquidity for the shares. If you wish to retain
references to liquidity,
 Jonathan E. Johnson
Overstock.com, Inc.
December 20, 2019
Page 2
         please revise your disclosure to state that registration may result in
greater liquidity. We
         believe it is inaccurate to state that you are registering the shares,
in part, to provide
         greater liquidity, when in fact you are registering the shares because
you are required to
         do so under the federal securities laws.
Alternatives and Outcomes Based on Stockholder Vote, page 5

3.       We note your response to comment 3 and your amended disclosure that
"alternative
         structures could include . . . if there is a sufficient number of
authorized shares of
         Preferred Stock undesignated as to series, the issuance of a new
series of Preferred Stock
         as a dividend or the use of depositary shares, with each depositary
share representing a
         fraction of a share of a new series of Preferred Stock." Please
provide a brief description
         of how these alternatives will "achieve the objectives" of the
Dividend. In this regard, we
         note that your description of these alternatives does not explain how
shareholders
         receiving the alternative securities will receive any benefits related
to digital or blockchain
         enhancements.
Purpose and Effect of the Series A-1 Preferred Proposal, page 6
Purpose and Effect of the Series B Preferred Proposal, page 8

4.       We note your response to comment 5. Assuming that your analysis of
Delaware contract
         interpretation law is correct, please explain how your disclosure that
there is a conflict
         regarding the Board's ability to unilaterally increase or decrease the
number of authorized
         shares under the Certificates of Designation is consistent with your
disclosures that (1) the
         July 2019 amendments to the Certificates of Designation were not
properly authorized and
         (2) adoption of the Proposals will result in a loss of stockholder
voting rights.
         Alternatively, please revise your disclosure to remove references to
such "conflict" and
         make clear that the Certificates of Designation require stockholder
approval to increase or
         decrease the number of authorized shares thereunder.
General

5.     We note your response to comment 8. We are unable to agree with your
view that the
       proposed amendments to eliminate the class vote requirements in the
Certificates of
       Designation are inextricably intertwined with the other proposed
amendments. Based on
       your disclosure, it appears that the Dividend can be issued as
contemplated regardless of
       whether such class vote requirements are eliminated. In addition, we
view such proposed
       elimination of certain preferred stockholder voting rights as material
matters that would
       substantively affect stockholder rights, rather than as immaterial
matters. As such, please
FirstName LastNameJonathan E. Johnson
       unbundle the proposed amendments to eliminate the class vote
requirements in the
Comapany NameOverstock.com, Inc. the other proposals so as to allow
stockholders to vote on
       Certificates of Designation from
       these matters separately.
December 20, 2019 Page 2
FirstName LastName
 Jonathan E. Johnson
FirstName LastNameJonathan E. Johnson
Overstock.com, Inc.
Comapany20, 2019
December NameOverstock.com, Inc.
Page 3
December 20, 2019 Page 3
FirstName LastName
        We remind you that the company and its management are responsible for
the accuracy
and adequacy of their disclosures, notwithstanding any review, comments, action
or absence of
action by the staff.

       You may contact Kat Bagley at 202-551-2545, Valian Afshar at
202-551-8729, Ted Yu
at 202-551-7266 or Mara Ransom at 202-551-3264 if you have questions.



                                                          Sincerely,

                                                          Division of
Corporation Finance
                                                          Office of Trade &
Services
cc:      Robert W. Reeder III