This article investigates the rationales and activities of nine nonprofit intermediary organizations operating in Israeli public schools, under similar missions of promoting school entrepreneurship. I apply a multiple case study qualitative methodology with in-depth interviews and complementary content analysis to investigate how those intermediaries operate and thrive. I depict how the concept of school entrepreneurship is formed and facilitated and reveal how state policy and intermediaries' activities interact and shape schools' realm, as shown in three specific paradoxes emerging from my analysis.