Borrowing from paradoxical leadership literature and using the case of a social enterprise formed from a traditional nonprofit, the present study identifies a set of multilevel skills that helped the leader address the two social–business tensions, namely, continuance as a nonprofit and the forming of a social enterprise and the sustenance of a social enterprise and preventing the drift towards a for-profit orientation during the formation of social enterprise and in its sustenance thereafter. The individual-level paradoxical leadership skill of balancing idealism and pragmatism, the organizational-level paradoxical leadership skill of navigating organizing contradictions, and the societal-level skill of gauging societal developments and their organizational implications helped address the two different manifestations of social–business tensions during the formation and sustenance of a social enterprise. Implications for paradoxical leadership, social–business tensions, and social enterprise literature are discussed.