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OVERSTOCK.COM,   INC. 6350 South 3000 East Salt Lake City, UT 84121 APPENDIX I (Revised as of   October 9, 2015)

Onboarding   Overstock onto PRO Securities ATS Platform Actor /Situs Actions Overstock   Overstock Initial Securities Issuance Overview Overstock executes Securities   Trading Agreement with PRO Securities ATS 2 Broker-Dealer(1) Broker-Dealer   shares customer information with Overstock or Overtsock’s Transfer Agent. The   book entry of trades is derived from the proprietary ledger, publicly   available copies of which can be mathematically proven to be valid copies   using cryptographically-secured distributed ledger technology. The digital   securities register maintained by Overstock and its Transfer Agent consists   of the proprietary customer information and the proprietary ledger***   Overstock takes necessary corporate steps to authorize the issuance of   digital securities Digital securities are sold by Overstock or Overstock’s   underwriter to initial purchasers* These potential purchasers of digital   securities are onboarded by Broker-Dealer** NOTE: This depiction and the   accompanying description are summary in nature and are intended only as an   aid to understanding the processes associated with trading Overstock’s   digital securities. The processes depicted herein may change, depending on   the final terms of license and other agreements that have yet to be   completed. (1) A sole broker-dealer will be licensed to provide access to the   PRO Securities ATS digital securities trading platform. Initially, we expect   that this broker-dealer will be DriveWealth, LLC. *Process by which   securities will be purchased are shown in Slides 5 and 8-13. **As shown in   slide 6. Those institutional and retail customers of Broker-Dealer that are   potential purchasers of digital securities are referred to in this Appendix   as “end-use customers.” ***As set forth in slides 14-16. Institutional /   Retail customers of Broker-Dealer express interest in purchasing digital   securities

Onboarding   Broker-Dealer to PRO Securities ATS Actor /Situs Actions Broker-Dealer   Broker-Dealer enters into all required agreements with PRO Securities ATS   Broker-Dealer enters into license agreement with TØ.com to license the TØ.com   software to create end-use customer portfolio key and wallet Broker-Dealer   performs a test trade 3 NOTE: This depiction and the accompanying description   are summary in nature and are intended only as an aid to understanding the   processes associated with trading Overstock’s digital securities. The   processes depicted herein may change, depending on the final terms of license   and other agreements that have yet to be completed.

1. Broker-Dealer   executes a subscriber agreement that details the relationship and   requirements for Broker-Dealer and its end-use customers to access the PRO   Securities ATS, including Broker-Dealer taking all responsibility for   regulatory compliance for itself and its end-use customers. 2. Broker-Dealer,   via its related OMS, will enter into a FIX certification with PRO Securities   ATS. This certification will be performed via the Internet in the PRO   Securities ATS QA test environment. a. Certification is a one-time process. b.   After successful certification is completed, trading in digital securities   can commence after specific telecom IPs and Ports are given to Broker-Dealer.   3. A test trade will be performed. Onboarding Broker-Dealer to PRO Securities   ATS 4

Performs   KYC/AML checks on underwriter New underwriter account created Creates   portfolio key and wallet Key made available to underwriter for placement of   securities with investors in primary issuance Primary Issuance of Securities   Actor /Situs Actions Broker-Dealer 5 PRO Securities ATS Creates committed key   and wallet NOTE: This depiction and the accompanying description are summary   in nature and are intended only as an aid to understanding the processes   associated with trading Overstock’s digital securities. The processes   depicted herein may change, depending on the final terms of license and other   agreements that have yet to be completed. Initial account data available to   underwriter through Broker-Dealer’s digital securities user interface Engaged   underwriter executes account documentation with Broker-Dealer Overstock Engages   a broker-dealer to act as underwriter of an offering of digital securities   Confirms conditions for primary issuance satisfied Delivers issuance order to   Pro Securities ATS directing delivery to underwriter’s account Credits   underwriter portfolio wallet with initial issuance of digital securities   Initial credit written to the proprietary ledger, thereby settling the   placement to underwriter Transfer Agent Trade data available to Transfer   Agent Overstock confirms to Transfer Agent that all requisite corporate   approvals for issuance of a series of digital securities are in place Sell   Order placed by underwriter (See Slide 10)

Such end-use   customer executes account documentation with Broker-Dealer Performs KYC/AML   checks on end-use customer New end-use customer account created Creates   portfolio key and wallet Onboarding a New End-Use Customer Actor /Situs   Actions Broker-Dealer 6 PRO Securities ATS Creates committed key and wallet   NOTE: This depiction and the accompanying description are summary in nature   and are intended only as an aid to understanding the processes associated   with trading Overstock’s digital securities. The processes depicted herein   may change, depending on the final terms of license and other agreements that   have yet to be completed. Key made available to end-use customer for future   trading Institutional / Retail customers of Broker-Dealer express interest in   purchasing digital securities

1. A new   end-use customer of Broker-Dealer who wishes to trade Overstock’s digital   securities will complete Broker-Dealer’s applicable customer account   documentation. 2. Broker-Dealer will then perform its procedures for   onboarding new end-use customers, including requisite KYC and AML checks. 3. Assuming   all requirements are met for opening a new end-use customer account, a new   end-use customer account is created. 4. For end-use customers requesting   digital securities trading, two digital wallets are also created: a. Broker-Dealer   creates a unique customer key and “portfolio wallet.” b. PRO Securities ATS   creates a unique account key and “committed wallet.” Onboarding a New End-Use   Customer 7

End-use   customer logs in to Broker-Dealer’s digital securities user interface Create   Order to Buy Overstock Digital Security* Actor/Situs Actions Broker-Dealer   Customer balances and Overstock market data are shown End-use customer enters   buy order directly into Broker-Dealer’s digital securities user interface See   Slide 10 8 *Buy order and sell order processes are substantially similar with   appropriate changes to represent the characteristics of the order. NOTE: This   depiction and the accompanying description are summary in nature and are   intended only as an aid to understanding the processes associated with trading   Overstock’s digital securities. The processes depicted herein may change,   depending on the final terms of license and other agreements that have yet to   be completed. Buy Order placed by end-use customer*

1. End-use   customer logs in to Broker-Dealer’s digital securities user interface.   Permission to log in is subject to Broker-Dealer’s approval. 2. Once logged   in, end-use customer sees current top of book, level one market data with   respect to Overstock (the best bid and best ask price available) and the   contents of the end-use customer’s digital wallet. 3. Only anonymous trading   occurs. End-use customer cannot see its trading counterparts and PRO   Securities ATS does not have access to end-use customer identifying   information. Create Order to Buy Overstock Digital Security 9

Buy Order   (Place Trade) Actor /Situs Actions Broker-Dealer* PRO Securities ATS   Identifies customer’s committed wallet Creates commitment transaction Signs**   commitment transaction Sends execution report to Broker-Dealer’s digital   securities user interface Sufficient balance available? Buy Order Continued   from Slide 8 Demobilizes end-use customer’s available cash by proposed   purchase amount Creates FIX Order message Order pending Moves liability to   committed wallet Creates transaction response Receives a committed   transaction created by TØ software into the PRO Securities ATS matching   engine Crypto and FIX signatures match? Processes order Creates execution   report Order routed to PRO Securities ATS 10 Yes NOTE: This depiction and the   accompanying description are summary in nature and are intended only as an   aid to understanding the processes associated with trading Overstock’s   digital securities. The processes depicted herein may change, depending on   the final terms of license and other agreements that have yet to be   completed. Signs** FIX Order message *Trade is processed through the TØ.com   software accessed by the end-use customer through Broker-Dealer’s digital   securities user interface. **Signs = affixes cryptographically verifiable   proof of identity of the wallet and authority to enter the transaction.   Validates customer wallets and balances Yes

Buy Order   (Place Trade) 1. The TØ.com software checks to ensure that sufficient funds   are available to place the buy order, and demobilizes end-use customer’s   available cash by the proposed purchase amount. 2. The TØ.com software   creates a “committed transaction” (i.e., the buy order) for the end-use   customer’s committed wallet. 3. The TØ.com software places the order into the   PRO Securities ATS matching engine. The PRO Securities ATS acknowledges   receipt of the order back to the end-use customer. If a match does not occur,   the order will remain in the PRO Securities ATS matching engine until   canceled by end-use customer. 11

Matching Actor   /Situs Actions Broker-Dealer PRO Securities ATS Trade data available to   end-use customer through Broker-Dealer’s digital securities user interface   Committed wallet deducted Portfolio wallet receives digital security Initial   match successful? Maps order IDs to committed wallets Gets wallet balances   Sufficient balance available? Execute order* Trade written to the proprietary   ledger, thereby settling transaction 12 NOTE: This depiction and the   accompanying description are summary in nature and are intended only as an   aid to understanding the processes associated with trading Overstock’s   digital securities. The processes depicted herein may change, depending on   the final terms of license and other agreements that have yet to be   completed. *Utilizing the TØ.com software the execution of the transaction is   the settlement. Trade data available to Transfer Agent Yes Yes Buy/sell order   match Transfer Agent

Matching 1. After   an initial match occurs between buy and sell orders, the PRO Securities ATS   maps the identification to each end-use customer’s digital wallets. If there   are multiple sellers at the same price the allocations are based on the   current PRO Securities ATS order priority. 2. The committed wallets of the   buyer and seller are matched. If a match occurs (i.e., matching buy and sell   orders), the trade is executed. 3. The PRO Securities ATS writes the trade to   the proprietary ledger, thereby settling the transaction, and the proprietary   ledger is made available to the end-use customer through Broker-Dealer’s   digital securities user interface and to Transfer Agent. 13

Validation of   Copy of Proprietary Ledger By Distributed Ledger Network Technology Actor   /Situs Actions PRO Securities ATS* Blockchain 14 NOTE: This depiction and the   accompanying description are summary in nature and are intended only as an   aid to understanding the processes associated with trading Overstock’s   digital securities. The processes depicted herein may change, depending on   the final terms of license and other agreements that have yet to be   completed. *Utilizing the TØ.com software. **Anchor: mathematical derivation   of numbers and characters generated from ledger. Transfer Agent Creates   snapshot anchor** Creates proprietary ledger snapshot of securities trade   Trade written to the proprietary ledger Creates de minimis bitcoin   transaction and includes anchor data and submits to blockchain for embedding   Receives proprietary ledger snapshot Mathematical validation using   cryptographically-secured distributed ledger network technology Mathematical   proof that proprietary ledger snapshot matches proprietary ledger maintained   by PRO Securities ATS Miner receives de minimis mining fee Bitcoin   transaction with anchor data is included in suggested block by miners Block   is closed and saved to blockchain Confirms successful anchor Appends bitcoin   transaction to proprietary ledger

1. Following   the consummated digital securities transaction, the executed transaction is   reflected on the proprietary ledger that is maintained by the PRO Securities   ATS. If, for any reason, Bitcoin miners are unavailable to update the Bitcoin   blockchain (i.e., the distributed ledger), the proprietary ledger is not   impacted and will continue to reflect the current state of ownership of   Overstock's digital securities. 2. To commence the ledger distribution and   validation process, the TØ.com software creates a snapshot anchor for a set   of consummated digital securities transactions. 3. PRO Securities ATS   executes a minimal Bitcoin transaction and uses the TØ.com software to embed   the snapshot anchor data within that transaction. Because the snapshot anchor   data is encrypted and the Bitcoin transaction is entirely anonymous, Bitcoin   miners are unaware that they are associated with a digital securities   transaction in any way. Validation of Copy of Proprietary Ledger By   Distributed Ledger Network Technology 15

4. The PRO Securities   ATS Bitcoin transaction containing the snapshot anchor data is confirmed by   Bitcoin miners and added to a suggested block, which is then closed and   permanently and immutably saved to the blockchain. Bitcoin miners receive the   de minimis transaction fee associated with the 5. PRO Securities Bitcoin   transaction. PRO Securities ATS appends the Bitcoin transaction (including   the embedded snapshot anchor data) to the proprietary ledger, which already   reflects the relevant set of consummated digital securities transactions, and   provides an updated copy of the proprietary ledger to 6. Transfer Agent.   Transfer Agent mathematically validates the copy of the proprietary ledger   using cryptographically-secured distributed ledger network technology,   thereby mathematically proving that its copy of the proprietary ledger   matches the proprietary ledger maintained by the PRO Securities ATS.   Validation of Copy of Proprietary Ledger By Distributed Ledger Network   Technology (continued) 16

Update of Share   Register Actor /Situs Actions Transfer Agent Broker-Dealer 17 NOTE: This   depiction and the accompanying description are summary in nature and are   intended only as an aid to understanding the processes associated with   trading Overstock’s digital securities. The processes depicted herein may   change, depending on the final terms of license and other agreements that   have yet to be completed. End-Use Customer Requests end-use customer data   from Broker-Dealer Accesses wallets from its books and records Receives   correspondence from Overstock (e.g., proxy materials) as requested by   Overstock Looks up end-use customers’ private information associated with   applicable wallets Provides end-use customer data Receives end-use customer   data Provides information to Overstock and delivers c