Examining the careers of democratic heads of state and government from 1960–2010, we find that one in every seven turns to the private sector after office. Distinguishing between the factors that attract leaders to business and those that render leaders attractive, we find that the global CEO compensation rates, cultural norms, having served in office in Anglo-Saxon countries as well as their personal background matter. We also find that certain economic outcomes and policies in office such as economic growth and reduction in state spending are often associated with post-tenure business careers. We do not find evidence, however, that leaders are able to implement policies with future careers in mind, which would in turn raise concerns over accountability.