The development of women’s entrepreneurship has positive implications for societal and economic growth. In this study, we examine the effects of culture and, more specifically, collectivism on women’s businesses. With a mixed-method and multilevel approach, we conducted a quantitative country-level analysis followed by a qualitative study of women entrepreneurs. Our results indicate that collectivism at the in-group level (family and close friends and colleagues) is a particularly important predictor of women’s business ownership. Furthermore, it is a balance of both collectivism and individualism at the in-group level that is most conducive to women’s business ownership. Institutional collectivism (at the societal level) acts as a background condition that influences the way in which in-group collectivism directly affects women’s business ownership. More specifically, when engaging in business development, women are primarily influenced by their in-groups. The freedom to pursue individual goals, combined with support from the in-group, provides the most beneficial environment for women to develop businesses, especially in societal-level cultures at the extreme ends of the collectivism spectrum—highly collectivistic or highly individualistic. A better understanding of these cultural factors should help with designing better business development training programs for women entrepreneurs and properly advising policy makers.