In this paper, we present the lessons learned by bringing in content and content-creators from local community media initiatives into the technological fold of the web. Our work focuses on the Community Radio (CR) ecosystem in India, and through extensive field-studies we develop an in-depth understanding of the operations, strengths and challenges of a CR station. Based on this, we outline the design of a system that combines the content creation processes of a CR station with the mobile web. The system was evaluated with the users of a CR station in Bangalore over a month long deployment. Our key take-away is that the incorporation of a mobile web based delivery system can play a critical role in expanding the reach and consumption of community media in the target communities. Conversely, the relevance of CR content and role of radio jockeys (as trusted members of the community) can be a key driver in adoption of the mobile web in these communities. Together, such a hybrid approach points the way forward for more successful deployments of community media systems, and reveals several interesting HCI issues to be studied further.