Philanthropic involvement in K-12 education is growing, and it increasingly shapes the direction of reforms pursued throughout the country. A recent report from the NewSchools Venture Fund offers a thought experiment on how philanthropists can make a “big bet” over the next decade on innovative schools—a broad category that generally includes schools with a high degree of education technology use and so-called personalized approaches to learning that likely utilize digital platforms. Unfortunately, the report fails to provide a meaningful examination of research or a thorough basis for its recommendations. This critique focuses on six key concerns regarding the report: it fails to consider human capital constraints or to sufficiently consider obstacles confronting classroom technology usage, it overlooks equity concerns and past problems with dependence on external professional services, and it ignores both the potential for disruptive reform churn and the danger of philanthropic efforts altering public education systems in undemocratic ways. For these reasons, the report’s usefulness to policy and practice is limited.