Academic entrepreneurship, where faculty members spin out of the university into startups, represents a growing phenomenon with significant but underexplored psychological implications. While entrepreneurial activities allow academics to commercialize research and contribute to societal innovation, this shift often involves navigating complex dual roles. Balancing the academic obligations with the demands of entrepreneurship poses unique challenges that can significantly impact their well-being. Despite the growing body of research on entrepreneurship and well-being, the specific experiences of academic entrepreneurs remain unexplored. This study investigates how entrepreneurial endeavors impact academic entrepreneurs’ well-being through semi-structured interviews and longitudinal diaries. Findings reveal that academic entrepreneurs’ journeys typically begin with intrinsic or extrinsic triggers. Intrinsically motivated individuals exhibit excitement and optimism, while those entering due to external factors often face hesitation and self-doubt, particularly when lacking business-related skills. As academics progress in their journey, they face the complexities of balancing academic and entrepreneurial responsibilities, which can lead to stress and role conflicts. Strong interpersonal dynamics, such as trust and familiarity with collaborators, and institutional support, including mentorship and resources, play a critical role in mitigating these tensions. Those who engage in identity work—integrating their academic and entrepreneurial roles—report greater resilience and satisfaction. This study contributes to understanding well-being in academic entrepreneurship, adding to the broader entrepreneurship and identity literature by emphasizing the psychological effects of having a hybrid role. By exploring the opportunities and challenges inherent in balancing academic and entrepreneurial demands, this research aims at providing actionable insights for universities and policymakers.