Using results from 22 key informant interviews from 15 different universities, we analyze why various centers/programs on philanthropic and nonprofit studies started, their key revenue sources, the diversity of funding sources, the role of leadership, succession planning, and what they might have done differently to make things better. These case studies provide insights as to why some centers/programs fail, others barely survive, yet some thrive. While the old saying, “It’s better to be lucky than good” remains true. We found that many of the things we teach in our academic programs work well when leading academic centers: diversify income streams, do not become too reliant on one donor, provide for leadership transitions and succession plans, raise money for endowments, and build advisory boards.