The occupational influence of life partners on each other’s health and well-being has recently been discussed in the literature. However, research has tended to focus on job demands of dual-employee couples. This study investigates how entrepreneurs whose partner is either in entrepreneurship or in employment experience health and well-being. Specifically, we examine two types of dual-career couples: (i) entrepreneur-employee and (ii) entrepreneur-entrepreneur. Building on crossover theory, which suggests that resources and stressors from one’s work domain can transmit to the family domain and affect one’s partner, we examine how different combinations of a couple’s occupations influence the entrepreneur’s subjective health and well-being. An investigation of more than 6,000 individuals in 39 European countries, with endogeneity controlled for using the instrumental variable approach, reveals that entrepreneurs whose partners are also entrepreneurs have a higher level of health and well-being, in comparison with entrepreneurs partnered with employees. Contingencies are examined, with the crossover effect differing based on entrepreneurial stage, gender, and whether couples are unmarried or in legal marriage/civil partnership.