Supporting student learning, especially in high-need urban schools, is impossible by simply focusing on teaching and curriculum issues. Rather, school leaders must also pursue initiatives traditionally considered outside the purview of schools and assume different mind-sets and practices to do so successfully. This was the case when a principal of School 17 (one of the poorest elementary schools in Rochester, New York), decided to establish a health clinic on his school premises in the late 1990s. Having a child almost die in his arms convinced him to bring community services into the school. Examining the development of this initiative will help educators appreciate not only the value of bringing community services to schools, but also the benefits of assuming an entrepreneurial mind-set. ["Educator as Entrepreneur: Bringing Community Services to Schools" was written with Ralph Spezio.]