Crowdfunded microlending research implies that both communal and agentic characteristics are valued. These characteristics, however, are often viewed as being at odds with one another due to their association with gender stereotypes. Drawing upon expectancy violation theory and research on gender stereotypes, we theorize that gender-counterstereotypical facial expressions of emotion provide a means for entrepreneurs to project “missing” agentic or communal characteristics. Leveraging computer-aided facial expression analysis to analyze entrepreneur photographs from 43,210 microloan appeals, we show that women benefit from stereotypically masculine facial expressions of anger and disgust, whereas men benefit from stereotypically feminine facial expressions of sadness and happiness.