In this article, we utilize 25 years of data on the Milwaukee voucher program to test the relationships among organizational liabilities of newness, institutional affiliation, market‐share, and regulatory environment on the cumulative risk of school failure. Overall, we find that 41 percent of all private voucher schools operating in Milwaukee between 1991 and 2015 failed. Start‐up voucher schools, and those unaffiliated with a larger institution, have comparatively higher failure risk over time. The results of our analysis shed light onto one of the long‐term impacts of a public policy reform premised on social entrepreneurship. We conclude that policymakers should consider the consequences of organizational failure when utilizing nongovernment entities in the provision of public goods, and that scholars focus increased attention to understanding the negative externalities created by public entrepreneurship.