Although cognitive theory has been adopted to explain entrepreneurial risk behavior, the complex interaction between culture and risk perception in stimulating or inhibiting entrepreneurship has yet to be fully explored. Explanations of why some people start businesses and face uncertainty while others choose a “safer” career path have shifted during the years, from personal traits—such as risk propensity—to more cognitive variables—such as risk perception. Although all of these cognitive explanations have received considerable empirical support, none of them focus on cultural differences that may affect, at the individual level, the attractiveness and the perceived riskiness of an entrepreneurial career path. Thus, our study aims to fill this gap in the literature, linking cultural differences and entrepreneurial risk perception. We analyze how perceptions of the culture influence risk perceptions associated with the decision to start a new venture. We assess perceptions of culture along five dimensions: (1) Opportunity seeking; (2) Entrepreneurial traits; (3) Capability beliefs; (4) Responsibility taking; (5) Entrepreneurial motivation; and (6) Entrepreneurial fears. We also assess risk perception in a multidimensional way, using a scale created to measure the perceived risk of missing and sinking the boat (Dickson & Giglierano, 1986).