Entrepreneurship is considerable not only desirable but necessarily in the contemporary world, and education is no different. However, contemporary calls for entrepreneurship are not too dissimilar to past calls for strategy and strategic approaches to educational (and particularly school) leadership. Drawing on the emerging field of relational studies and empirical projects on different forms of schooling, I highlight how in seeking to capture entrepreneurship into products (e.g., books, teaching materials) or replicate it (e.g., through mentoring / coaching) very much overlooks the strategies that make it possible in the first place. Put simply, chasing entrepreneurship, much like strategy before it, is always doomed to be playing catch up – even if replication is achieved - as those leaders identified as entrepreneurial have moved on. Prosecuting the case through a relational analysis I argue that like most developments in educational leadership studies entrepreneurship focuses on idealising and legitimising the heroic great man mythology.