How can one predict entrepreneurship, an individual’s participation in the founding of a new organization? We propose that the organizational context of an individual either accelerates or retards the likelihood of entrepreneurship, depending on the individual’s role in the organization. The effects of role hinge, we argue, on the founder’s charismatic identity, and the decoupling of this identity from the organization as it ages and grows. Our findings support the proposition that organizational properties that affect the likelihood of becoming an entrepreneur do so in opposite ways for organizational members and founders. We discuss how our theory and results demonstrate the value of a sociological perspective on entrepreneurship.