The study aimed to compare entrepreneurial self-efficacy and psychological well-being as well as the relationships between these constructs in Brazilian and Argentinean female entrepreneurs. A total of 404 women participated in a survey during a development program at two universities located on the border. The results point to several similarities, which can promote rapprochement and development, and differences, which, if not managed assertively, can lead to conflicts. The results demonstrate associations between entrepreneurial self-efficacy and psychological well-being, thereby expanding the entrepreneurship literature. This study develops the understanding of motivation in entrepreneurial cognition, redefines entrepreneurial success, boaden the scope of women’s entrepreneurial role in this border region, and identifies elements to promote cooperation between female entrepreneurs in both countries. From a managerial point of view, the research shows the need for managers to be aware of cultural differences in everyday actions and negotiations within these territories.