Gender research in management has surged in the last decades. Although most studies have taken a traditional status-based view in which men have universal advantages over women in terms of leadership and entrepreneurial activity, we argue that such advantages may reverse under certain contexts. Leveraging role congruity theory, we designed a 2 × 2 × 2 between-subjects experiment to examine the conditional effects of early-stage startup investors’ gender stereotypes on their funding decisions. After testing 226 early-stage investors’ responses, we find that investors can exhibit bias toward men as well as women entrepreneurs when making funding decisions. Specifically, investors are more likely to favor sex-trait congruent entrepreneurs (i.e., agentic men and communal women) than incongruent ones, and such effects are stronger when the entrepreneur targets the male market than the female market.