This empirical study investigates how students' perceptions of risk-taking and coping with uncertainty change while they are exposed to experience-based entrepreneurship education. The aim of the study is twofold. First, the authors set out to identify the dynamics of entrepreneurial thinking among students experiencing risk and uncertainty while conducting their entrepreneurial projects in a team. Second, the role of experiential education in the evolution of students' approach to risk and uncertainty is examined. The article is based on a longitudinal qualitative study conducted between 2009 and 2014 in Namibia. The research team followed 13 young individuals from the beginning of their studies in entrepreneurship until their graduation and the start of their professional careers. The findings pertaining to the dynamics of students' perceptions of risk in entrepreneurial experiences and learning bring a more accurate understanding of the transformative character of entrepreneurial learning as well as offering practical implications for how to conduct entrepreneurship education in a way that is meaningful to learners.