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The context for economic and engineering entrepreneurism is well researched, but there is less information on the context for emerging social entrepreneurship, especially in K-12 public education. This purpose of this study was to examine five contextual factors (organizational structure, leadership, culture, process, and workspace) in two innovative early college programs to answer the question: what contextual factors impeded or promoted social entrepreneurism? Using data from design team meetings, interviews, observations and documents, the study traced four key innovative ideas for evidences of entrepreneurism. The author found key promoters for entrepreneurism and discovered that some contextual factors could often counteract other anti-entrepreneurial factors. The results offer hope for social entrepreneurism in public education and suggest avenues for future research.