This study aims to untangle the role of risk propensity as a predictor of self-employment entry and self-employment survival. More specifically, it examines whether the potentially positive effect of risk propensity on the decision to become self-employed turns curvilinear when it comes to the survival of the business. Building on a longitudinal sample of 4,973 individuals from the German Socio-Economic Panel, we used event history analyses to evaluate the influence of risk propensity on self-employment over a 7-year time period. Results indicated that whereas high levels of risk propensity positively predicted the decision to become self-employed, the relationship between risk propensity and self-employment survival followed an inverted U-shaped curve.