We explore the question of how gender and related stereotypes might influence investors’ perceptions of early-stage ventures using a novel dataset of 185 videos of one-minute pitches in an elevator pitch competition. Drawing from social role theory we test the impact of perceived gender stereotypes, by examining the entrepreneur’s sex, gendered behaviors (masculine vs. feminine), and gender consistency of these behaviors on the pitch evaluations made by investors. We find that sex alone does not prevent success in moving forward in the process. However, gendered expectations do make a difference as women entrepreneurs who present masculine behaviors are more likely to be evaluated positively than those who do not. Interestingly we find women entrepreneurs have stronger communication skills, but rates of women’s entrepreneurial participation remain weaker than men’s. Our findings raise new and important questions for the role of gender perceptions by investors in women’s entrepreneurship and funding outcomes.