Superintendents and other school administrators live with tensions in political economy. The voting public believes school funding is fixed when the economy expands and new state programs are introduced. Administrators are publicly criticized when, strained for resources, their schools cannot perform within the "do more with less" paradigm. This research begins to trace patterns of political economy in schooling. The author emphasizes the last economic recession along with funding for schools to describe challenges for school administrators. He also emphasizes entrepreneurial movements in schooling to describe competition that public school administrators face. A jaundiced viewpoint asserts that public school funding suffers entropy while entrepreneurial school funding expands. (Contains 4 tables.)