An incentivized peer-to-peer content and royalty distribution system is disclosed. This system may distribute contents including, without limitation, music files and other playable formats, videos, e-News, eZines, eBooks, software, applications, learning tools, and other types of content. The system allows users to support a product, content or artist not available through traditional distribution systems such as brick-and-mortar retailers, online retailers, and also allows users to market, promote, or solicit other users, buyers and/or promoters to license, buy or use the content they are supporting and to share in the royalties collected from the plurality of purchases occurring within the peer-to-peer, informal distribution chain. Further, the distribution system may reward users who are successful in convincing other users to license or purchase the product or content based at least in part on use and analysis of metadata associated with content transferred within an informal distribution chain.