This paper presents a longitudinal study of the course ‘High-tech Entrepreneurship and New Media’. The course design is based on socio-cultural theories of learning and considers the role of social capital in entrepreneurial networks. By integrating student teams into the communities of practice of local start-ups, we offer learning opportunities to students, companies, and academia. The student teams are connected to each other and to their supervisors in academia and practice through a community-system. Moreover, the course is accompanied by a series of lectures and group discussions. In this paper we want to present our experiences and to reflect upon the design changes between the first and the second instance of the course. The evaluation of the course showed that the work on real-world problems and the collaboration in teams together with partners from start-up companies were evaluated as very positive, although design