Women entrepreneurs are a driving force in every country in which they operate yet a majority of entrepreneurship research is still focused on male entrepreneurs. In this article, we share the stories of eight successful women entrepreneurs from Japan and China and explore the entrepreneurial processes at play in their businesses. Through a semi-structured interview process, the women shared their start-up motivations, challenges at startup and during growth, and factors that led to their success. Our qualitative analysis revealed the important interplay of gender, institutional factors and culture in the entrepreneurial process. The women’s rich stories revealed how and why their businesses came into being, and how they were able to overcome challenges typical to all entrepreneurs and those specific to women. Our study sheds light on women’s entrepreneurial cognition and behavior in two cultures with traditional gender role expectations