The purpose of this investigation was to explore through a historical case study the ways in which one principal mentored and built capacity with a school-based cohort of teachers who became school leaders themselves in a variety of capacities. Findings reveal a generative female leader who embraced strong philosophical and theoretical foundations enacted in an enriching, innovative culture. This case study illustrates the nested activity of leadership in the development of a learning organization focused on strong relationships, continuous adult learning, and practical leading capacities. This nested activity contributed to leadership dispersion, strong community identity, and personal transformative experiences for teachers who chose to become leaders as well. Findings suggest ways in which principals in contemporary schools can mentor and develop teachers to become teacher leaders and learning-centered administrators.