Philanthropy has a long history in the American public school system, but a marked influx of private dollars and a shift towards strategic giving has drawn increased attention. Prior research has explored funding patterns, strategies used by foundations to leverage their grants dollars, and the emergence of venture philanthropy; yet little has been done to understand the perspectives of the foundations, the philanthropic approaches that guide their giving, and the desired outcomes of their involvement in K-12 education giving. Using a multimethod qualitative design, this study aims to fill this void through a line of inquiry focused on the perspectives of the leading foundations and how they differ from one another in K-12 education giving. This study reviewed the 35 largest United States based K-12 education foundations by total annual giving in 2013 in two stages. Stage One of the study analyzed annual reports, mission statements, foundation portfolios, and online foundation websites to grasp the degree of adherence to venture philanthropic tenets and how foundations differ in their approach and perspectives in education philanthropy. Stage Two then sought to capture the perspectives of foundation representatives through interviews to better understand why foundations choose to give to education, the philanthropic approach of their giving practices, and the desired outcomes from their work in K-12 education. In the study, I found patterns of similarities and differences in foundations’ perspectives, approaches, and desired outcomes by their degree of adherence to venture philanthropy. Further, I illustrated how some moderate to high venture philanthropy foundations are acting as policy entrepreneurs.