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I have years of professional experience with online collaboration, including the design, testing and administration of enterprise groupware software.
Some of the books I associate strongly with Wikipedia and my personal motivations of potentially contributing to and improving it include The Innovator's Dilemma by Clayton Christensen, The Road Ahead by Bill Gates, and The Wisdom of Crowds by James Surowiecki, in particular. The Road Ahead describes how, at one time, physically heavy, bulky volumes of books, distributed to American society by door-to-door salesmen through very high prices, allowed common families to invest in their own education, but as time went on, cheaper alternatives began to emerge, until the release of Microsoft Encarta which was not only less expensive, but also offered richer content of multi-media (incl. video and sound), distributed on CD-ROM via retail channels. This progression basically followed Clayton Christensen's disruption model. Then came along Wikipedia, even cheaper (free!) and bigger and better (potentially at least, in just about any respect). The Wisdom of Crowds helped make sense of how regular folk provided such innovation.