Entrepreneurship research has in recent years examined women entrepreneur’s perceptions and expectations from the entrepreneurial experience (Bird and Brush, 2002; Cliff, 1998; Olson and Currie, 1992). Despite these efforts, there is a lack of agreement on the existence of gender-related differences in psychological and motivational patterns of entrepreneurs. Some authors argue that compared to men, women managers´ definition of success tends to be geared toward more “subjective” criteria, while others contend that these differences do not exist (Catley and Hamilton 1998; Eagly, 1995; Fagenson, 1993; Fisher, 1992; Shane, Kolvereid and Westhead, 1991). This paper brings a nuance to these two extreme perspectives recognizing that males and females entrepreneurs have both similarities and differences that are prompted by specific contextual factors. In particular, using Social Identity Theory (SIT) and insights drawn from the literature on women entrepreneurs, we contend that parenthood, and especially the presence of dependent children, is a powerful driver of change in entrepreneur’s perceptions of success for men and women entrepreneurs, yet those effects are stronger for women. Moreover, we content that the extent to which entrepreneurs will depart from gender-stereotypic attitudes will be moderated by the stage of development of the business.