While shifts in entrepreneurial venturing have often been seen as the work of visionaries or uncontrollable market forces, we propose that these changes stem in part from an evolving political theory of legitimate venturing. Building on the political philosophy of Isaiah Berlin and Charles Taylor, 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 expressions of freedom are reinterpreted as threats to freedom as they grow dominant. The result is a dialectical political theory of entrepreneurial capitalism. Using evidence from the past 250 years, we identify three periods of American entrepreneurial organizing around conflictual business models that produced frictions in the exercise of freedom. We then show how these freedoms’ frictions produced contestation that a new entrepreneurial form resolved for a time before frictions emerged anew. Finally, we draw out the implications for interpretations of entrepreneurial capitalism today.
