Research suggests that the risk and uncertainty associated with entrepreneurial activity deters entry and contributes to the high rates of new business failure. In this study,we examine how the ability to reduce these factors by means of hybrid entrepreneurship—the process of starting a business while retaining a “day job” in an existing organization—influences entrepreneurial entry and survival. Integrating insights from real options theory with logic from the individual differences literature, we hypothesize and find that individuals who are risk averse and have low core self-evaluation are more likely to enter hybrid entrepreneurship relative to full-time self-employment.In turn, we argue and find that hybrid entrepreneurs who subsequently enter full-time self-employment (i.e., quit their day job) have much higher rates of survival relative to individuals who enter full-time self-employment directly from paid employment. Adding support to our theory that the survival advantage is driven by a learning effect that takes place during hybrid entrepreneurship, we find that the decrease in exit hazard is stronger for individuals with prior entrepreneurial experience. Taken together, our findings suggest that individual characteristics may play a greater role in determining the process of how (rather than if) entrepreneurial entry occurs, and that the process of how entrepreneurial entry transpires has important implications for new business survival.