This article argues that contemporary political theory often contains an obscured supposition that I call the entrepreneurial assumption. This assumption can be seen most clearly when political theorists who do not have economic expertise per se theorize the relationship between their political thought and taxation. In order to explicate the entrepreneurial assumption, the article engages in close readings of John Rawls, Robert Nozick, and Ronald Dworkin. By elaborating on each of these authors' views, the importance of preserving “talent” through a system of taxation, the centrality of the entrepreneurial assumption can be seen more clearly.