In this paper we draw on the political philosophy of Isaiah Berlin and Charles Taylor to develop a political theory of entrepreneurial capitalism. Specifically, we introduce the construct of “entrepreneurial imaginaries” as collective moral judgments of forms of entrepreneurial organization that are considered threats or aids to mutual freedom. We theorize that forms of entrepreneurial organization that were once understood as aids to freedom are reinterpreted as threats to freedom as they grow dominant. The result is a dialectical political theory of entrepreneurial capitalism. We illustrate the theory by showing how it can explain the evolution over America capitalism over the last two centuries, and we draw out the implications for interpretations of entrepreneurial capitalism today.