This chapter presents a case study of the creation and evolution of a fee-based, multi-company Community of Practice (CoP) for Chief Information Officers (CIOs) in the San Francisco Bay Area over a six-year period. It describes the principles, processes and practices required to form and maintain a trust-based, face-to face, learning organization where members share accumulated knowledge. Additionally, it states some of the individual, collective and Information Technology industry benefits and results that have accrued from member participation in the CIO Community of Practice. The authors hope that the description of this CoP will foster the same sense of excitement for would-be practitioners that they feel.