This qualitative, grounded theory study focused on the experiences of 10 nonprofit executives in New York City. This study sought to identify patterns and regularities in the behavior of successful social entrepreneurs. The analysis highlighted key similarities and differences between the traditional nonprofit model and the entrepreneurial nonprofit model and presented a framework for how to approach the social entrepreneurial process systematically and effectively. In addition, this research project sought to explore the environmental, organizational, and personal leadership factors that may distinguish the traditional nonprofit model from the entrepreneurial nonprofit model. The study uncovered some new themes and validated some existing theory. The new themes uncovered fell into three categories: (a) motivation, (b) capacity, and (c) start-up capital matters.