Device, system, and method of collaborative distribution of digital merchandise. For example, an apparatus for collaborative distribution of Digital Merchandise Items (DMIs) includes: a first computing device having an agent module to receive a command of a first user to purchase a DMI from a second user, to provide information to process a first electronic payment from the first user to the second user, to receive the DMI from a second computing device of the second user, to receive a confirmation that a second electronic payment was made from a third user to the first user, to transfer a copy of the DMI from the first computing device to a third computing device of the third user, to calculate a first portion of the second electronic payment to be maintained by the first user, to calculate a second portion of the second electronic payment to be transferred to the second user, and to provide information to process an electronic payment of the second portion from the first user to the second user.