Although IT has been very successful in enabling distributed,collaborative learning and knowledge creation in open-source communities, its promise in other contexts is still an open question. In this paper, the authors describe the deployment of a video-based Web2.0 platform in an executive education context. The platform, which has been developed by the authors, makes extensive use of video,profiling, game dynamics, agents and network visualizations in order to capture the attention and involvement of the learning community members. The goal was to provide executive education participants with an attractive, interactive platform for extending their learning and networking beyond the classroom. This experience has helped identify three main barriers to Web2.0 interorganizational learning and collaboration in executive education: technological barriers, motivational barriers and the inter-organizational aspect itself.