Chapter 5 explores key aspects of the gendered dichotomy assumed to underlie entrepreneurial endeavour and achievement. Entrepreneurial success is predominantly understood in gendered terms as a consequence of qualities associated with masculinity while women are assumed to play supportive roles in business and enterprise. Even though successful female entrepreneurs are increasingly acknowledged, their ability to perform as business leaders is typically associated with masculine ideals of success, through an accomplishment of female imitations of masculinity. Chapter 4 challenges such persistent dichotomic approaches to gender in entrepreneurship. It is shown on the basis of data drawn from China’s new generation of entrepreneurs that women and men strategically display gender in the company and in the marketplace, in a manner that will maximize growth and profit for their firms. These women and men are not constrained by stereotyped gender ideals but rather utilize existing imagery and norms, and, when necessary, create new ones in doing business. In addition, the involvement of grandparents in supporting their daughters and daughters-in-law who are in business, wholly overlooked in consideration of female entrepreneurs, constitutes a hidden factor in the interplay of constructions of gender, family, and business experienced by female entrepreneurs in China.