The purpose of this investigation is 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. The 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 that contributed to leadership dispersion and personal transformative experiences for teachers who choose to become leaders as well.