A life of passion is a life well lived – this widely held notion constantly motivates us to pursue work we are passionate about. Work is a major essential life domain and interest in many people’s lives and so is family; however, engagement in one influence and is influenced by participation in the other. At work, passion is a highly desired but under-researched characteristic. While work passion offers benefits such as positive emotion experiences, improved job performance and feelings of flow at work, in case of imbalance, it can also elicit negative feelings, lead to rigid tenacity, and obstruct the pursuit of a fulfilling life. Drawing on job demands-resources theory and conservation of resources theory, our study offers understanding of the underlying mechanisms connecting work passion to the work-family interface among entrepreneurs, by considering the roles of psychological capital and self-regulation failure in interactions beyond the workplace. The study also explores how certain cultural dimensions such as activity orientation, specific-diffuse, individualism-collectivism, and masculinity-femininity contribute to the work passion – work-family interface relationship. By utilizing structural equation modelling and analyzing responses from 329 entrepreneurs in India and 270 entrepreneurs in Germany, the findings suggest that harmonious work passion is linked to work-family enrichment, whereas obsessive work passion is linked to work-family conflict. Furthermore, the findings highlight that psychological capital and self-regulation failure have varying impacts on work passion and work-family outcomes among entrepreneurs in India and Germany. Our study includes research and practical implications for academicians and practitioners, as well as agenda for future research.