Technology transfer and academia-industry collaboration have emerged as a growth engine for the knowledge-based economy. This study explores how academics at a research university and non-profit research institutions in San Diego have developed their practice and attitude to transfer and commercialize knowledge by drawing on qualitative approach. By tracing academic researchers’ trajectories and experience in transferring technology using 43 in-depth interviews and historical archives, this paper argues that academics learn to be capable of and comfortable with collaborating with industries by participating in companies as senior staff and by interacting with their entrepreneurial colleagues. Learning by doing and interacting helps academics to venture into entrepreneurial activity. Based on these observations, this research suggests that the policy focus should be on individuals and their learning experience.