In fall 2008, Columbia Business School graduate Andrea Wenner had nearly accomplished her initial goals for the nonprofit organization, Out2Play, she had founded three years earlier. Out2Play had raised $17 million, enough to finish construction of 40 playgrounds and permit another 40 to be built throughout the five boroughs of New York City. Struggling with "Founder's Dilemma," Wenner and her board considered the longer-term agenda for their successful social enterprise program.