Leadership education is offered in a variety of options at numerous colleges and universities: freestanding courses, seminars or within a program, case studies, online instruction, and umbrella leadership courses within various majors. This paper is about the Leadership Program at the City University of New York (CUNY). The Institute for Virtual Enterprise (IVE) is a CUNY Special Initiative charged with implementing a broad leadership program for the diverse student body found within all 17 CUNY campuses. IVE instituted a multifaceted approach to leadership education with an emphasis on having students apply their newfound leadership skills in the real world. This paper discusses the underlying theory, the curriculum design, and the events that occurred during the first run of the leadership program in 2003. It does not advocate for a particular best practice, but merely relates what worked best for the diverse student body of CUNY.