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Centralization and control of education can stifle initiative, prevent problem solving, and result in low student achievement. Nonetheless, many countries maintain centralized control of education and grant little autonomy to school directors to help them face the daily challenges of administrative problems or the more profound issue of parents who have little voice in their own education or the education of their children. School directors need autonomy to become educational entrepreneurs who take initiative and involve local constituencies. Woods and Woods’ (2009) define four types of entrepreneurialism. Business entrepreneurialism is intended to achieve a competitive advantage. Social entrepreneurialism reduces depravation and social exclusion. Public entrepreneurialism promotes a democratic vision for the good of the community. Cultural entrepreneurialism establishes meaning in the school. The paper examined two doctoral programs in educational leadership programs that intend to promote entrepreneurship. The program orientation, pedagogy, and outcomes associated with a doctoral program in California and a doctoral program in Mexico aimed to develop educational entrepreneurs. The founding of these two programs is described along with an analysis of a course in each program that attempts to develop the entrepreneurial skills of leadership. In their courses, students conducted oral history projects and analyses of leadership that were connected to a real school context. They were able to practice entrepreneurial skills and develop field projects to fulfill the requirements of research and school improvement. This conceptualization of the practice of leadership goes beyond the academic skills of information gathering and research. It includes entrepreneurial skills to help leaders advocate for all stakeholders. Experiences that have the potential to develop entrepreneurship can take students to new areas and ask them to step back and think in different ways.