This article aims to understand the role of the family in the professional lives of Brazilian female executives who have reached the top levels of management in large companies operating in Brazil, and female entrepreneurs. There are practically no studies in the field of management in Brazil that investigate the possible relationship between professional success and the influence of parents, especially among top executives. This is a qualitative, exploratory study consisting of two comparative case studies, with semi-structured interviews with 25 women entrepreneurs and forty-seven top women executives (CEOs, directors, and superintendents) aged between 30 and 70 years. For the analysis of the data, we used content analysis. We found that while the mothers of the women executives had influenced their success by stressing the importance of studying hard, the mothers of the women entrepreneurs had influenced their careers not only by enforcing to studying, but also through the entrepreneurial experience passed from one generation to the next.