We focus on the paradox generated when prospective entrepreneurs accumulate broad functional experience. On one hand, broad functional experience may facilitate an individual's pursuit of new ventures, as breadth enables the mastery of different skills and access to heterogeneous information and resources. On the other hand, such broad experience might hinder transition into entrepreneurship by imposing the threat of devaluation by key resource providers and thus undermining the legitimacy of entrepreneurial claims. To resolve this paradox, we introduce the notion of multiple category systems, which explains how a potential legitimacy discount of categorical membership can be avoided, when individuals are classified according to multiple categorical schemas simultaneously. Using the context of the music industry between 1990 and 2013, in which artists can launch independent record labels, we find that transition to entrepreneurship is most likely to occur when functional experience is broad but market experience is narrow: individuals have mastered a variety of skills but solicit few audiences. We further document that the paradox of breadth is attenuated when alternate methods of signaling legitimacy reduce the potential penalty of functional breadth and the corresponding need to develop narrow market experience.