In this chapter, we propose that gendered portrayals of entrepreneurs in mass media contribute to gender differences in entrepreneurship via two well-established, social-psychological mechanisms: self-efficacy and stereotype threat. Our thematic analysis of Entrepreneur magazine covers featuring women or men entrepreneurs shows that, in general, women are underrepresented on covers and, when they are shown, the accompanying textual and visual messaging is rather saturated with gender stereotypes. We urge for an increase in the quantity and quality of women’s representation in the media that is attentive to the role of the media in shaping the types of ventures women establish and operate. The aim is to encourage more women to enter into entrepreneurship with greater entrepreneurial self-efficacy or aspirations that are more ambitious. Media narratives populated with greater numbers of successful women entrepreneurs across a diverse range of business types and across industries beyond those traditionally associated with ‘feminine pastimes’ could lead to positive feelings that increase the wellbeing of women.