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This paper examines how gender and organizations interact to promote risk-taking. Previous research has examined how organizations are gendered and how organizations normalize professional risk-taking, but how do the mechanisms that gender organizations lead to riskier practices? How do gendered organizations encourage specific kinds of professional risk-taking? To better understand the relationship between gender and risk-taking in the finance industry, I interviewed ten professionals in the hedge fund industry and attended industry events to examine how organizational practices promote professional risk-taking and prevent women’s advancement. My research suggests that within alternative sectors of finance, organizational structures influence how risk is perceived and approached. These same structures lead to the underrepresentation of women in decision-making positions. I argue that these two outcomes are directly related.