Recent trends of democratic backsliding in post-communist Central European states have led scholars to look for structural and agent based economic explanations for the causes of said backsliding as well as how to promote democratic liberalism within said societies. Often agent-based explanations go hand in hand with structural inequalities in the long-term historical development of certain sectors and regions of the Visegrad Four states where anomie at the level of individual agents, resulting from limited economic opportunities, leaves them susceptible to radicalization. In this article, I test the extent to which entrepreneurship plays a role in both the support for democratization and liberal norms within the Visegrad Four states by analysing the relationship between entrepreneurship and the political values of the self-employed. Doing so, I argue that both entrepreneurial culture and shifting incentive structures have led self-employed individuals in Visegrad Four states experiencing democratic backsliding in the wake of the 2015 refugee crisis to be more supportive of liberal democracy than other groups. I contend that support for a given regime type among the self-employed is more elastic to fluctuating contexts and is determined by the interactions between entrepreneurial culture, perceived material interests, and the regime-type under which they reside.