John Dewey and Mahatma Gandhi conceived, built and successfully managed their educational institutions that were pioneering experiments in their respective historical contexts. Though a large volume of scholarly literature has been generated on their theories and schemes of education which were trend setters, there has been no major attempt to identify and articulate how these institutions were managed and none that compares them and generates cross- cultural insights about conceiving, building and managing institutions that are relevant for their socio historical contexts. John Dewey''s model of education was the heart of his philosophy of pragmatism which he expounded first from the University of Chicago where he built and ran his ‘Laboratory School''. Mahatma Gandhi''s scheme of education evolved and matured through four successive ''Ashram Schools''- models that progressively integrated learning and living into a concurrent process. His philosophy of non-violence became the increasingly central and dominant motif in each of the successive models.