Entrepreneurial ventures are often established, controlled and led through the commitment of individuals. This article problematizes the nature of the form of leadership relevant for the small business as it matures. In this way, it explores the temporal dimension to the appropriateness of distributed leadership in the context of the entrepreneurial business. The authors critique the opportunity that distributed leadership can bring to the maturing business. They illuminate a dilemma for entrepreneurs as to whether they should give up control for a broader distributed process of leading or continue a practice of leading that resonates with their essence of being entrepreneurial - independent, controlling responsive and opportunity driven. This dilemma is addressed by suggesting the contextualization of distributed leadership may offer the maturing business. The article concludes by reviewing development approaches that contextualize intervention and suggests a research agenda to contribute to a greater understanding of how leadership can become distributed in the maturing business.