Visionary leaders shape their actions and initiate transformation to reach a specific goal. To do so is critically important in South Africa, where the education system offers limited opportunities to manage a school in a manner that deviates from the prescribed norm. School leaders typically encounter barriers such as the inadequacy of the national educational budget, poor teaching and learning quality, limited curriculum offerings and insufficient learning resources. One entrepreneurial school leader nevertheless, successfully crossed the boundaries of income, culture, language and technology, and as a result now provides efficient and equal education to less privileged schools in the immediate vicinity of his school, in a rural area in Mpumalanga Province. This article reviews the proactive, innovative and visionary leadership of this principal and assesses the pedagogical justifiability of his entrepreneurship.