This qualitative inquiry uses the methodology of portraiture to investigate the relationship between founding holistic school leaders and the schools they lead. The guiding question of this investigation is, how do founding holistic school leaders embody their pedagogy through their approach to leadership within holistic schools? Through an immersive process of field observation, interviews, artifact gathering, and analysis, this study elucidates patterns across four diverse institutions and their founders. While all four schools studied here organize around a holistic pedagogy, these four institutions include schools with enrollment as small as 32 and as large as 1,500 students. They sit on three different continents and are both privately and publicly funded. The four school founders include both male and female leaders, they include different ethnic origins, and range in age from 40s to 70s. The schools are all remarkable in that they have been founded and organized around a clearly articulated holistic view of child development and the appropriate role of the school. All have sustained operations from between 13 to 28 years and look well established to continue into the future. This study concludes with the presentation of an original model of holistic leadership in holistic schools which suggests that holistic school leadership involves an adherence to core personal values and a strong unifying ethos. Holistic leaders of holistic schools are profoundly focused on this mission, and they do so with an ethic of beauty and grace. They attend closely to the cultivation of deep and trusting relationships that echo between the character of the leader and throughout the schools they lead creating a learning community of care. Finally, these leaders embody a powerful spirituality that radiates purpose and meaning, situating their school community in relation to something larger. This includes an attunement to place and a reverence for the natural world. These four remarkable individual stories combine to offer a hopeful vision for the possibility of holistic education through practices of holistic leadership. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]