Project Coach is an after school program developed and directed by the authors. The program, which is set in a high-need urban community in Springfield, Massachusetts, teaches high school and middle school students to be sport coaches and then to run youth sport leagues for elementary-aged youth in underserved neighborhoods in their own community. The program's premise is that sport coaches must employ a complex repertoire of skills, behaviors, and aptitudes that are associated with high achievement and success across a range of domains including school. Project Coach utilizes coaching as the vehicle to teach and practice key achievement skills such as communications, initiative taking, perseverance, conflict resolution, and other leadership capacities. This article describes the story of how eight years ago the authors began with an academic-based research question about the achievement gap and now find themselves running a medium-sized youth program that has three significant goals. First, it is a multi-layered and busy program that operates four afternoons a week with almost eight adult staff, 25 teenagers, and nearly 100-elementary aged youth. Second, it is a Smith College community outreach initiative that provides community service learning placements and other opportunities for numerous college students and research opportunities for other faculty. Third, it serves as a "laboratory program" for developing curriculum, conducting research, and preparing future educators with the skills and understandings that are applicable to working in the emerging field of out-of-school time. The authors' experience developing the model and establishing Project Coach as a successful outreach program that is supported by the college and the community offers one lens into the process of designing sustainable partnerships between higher education and local communities. What is instructive and perhaps generalizable about their story to other faculty involved in the development of community partnerships is that they emerged not as a component of a formalized college initiative, but as an enterprise that grew out of a series of academic and theoretical questions. In reflecting on this journey, the authors believe that the lens of social entrepreneurship helps explain their development.