Building on the job demands-resources theory, this study aims to investigate the relationships between study resources, personal resources, students’ well-being, and entrepreneurship outcomes. Longitudinal data were collected across three time points. A total of 154 Dutch students completed a questionnaire at the start, middle, and the end of an entrepreneurship program. The results of structural equation modelling demonstrated that study resources, specifically teacher-student relationships and student-student relationships, positively related to study engagement, which, in turn, fostered students’ entrepreneurial intentions. Moreover, student-student relationships related stronger to enhanced study engagement for students with high personal resources (psychological capital). Regarding the negative side of well-being, we found that student-student relationships significantly reduced study exhaustion, and study exhaustion negatively related to students’ entrepreneurship competence. Results confirmed the importance of study resources and personal resources in fostering students’ well-being and entrepreneurship outcomes. The findings contribute to continually improving teaching effectiveness of entrepreneurship programs.