This study identifies combinations of cultural practices and culturally-endorsed leadership ideals that lead to high levels of women’s self-employment. When uncertainty avoidance practices are absent of countries culture, the results suggest that low collectivism at the societal level (i.e., low institutional collectivism) is associated with high collectivism at the in-group level (family, close friends and colleagues) when a high share of women’s self-employment exists. However, this outcome can also be achieved in societies that are characterized by high institutional collectivism and low in-group collectivism, if self-protective leadership ideals are culturally-endorsed. The findings also suggest that the importance of collectivism should be relativized because its presence or absence, either in the form of institutional or in-group collectivism, is not necessary. Women’s entrepreneurship is likely to be high when uncertainty avoidance practices are absent and self-protective leadership ideals are present, showing that this combination of conditions is sufficient to achieve this outcome.