Active learning theory states that students learn best by having the opportunity to engage in realistic experiences beyond the textbook or lecture. In many fields, active learning is “learning by doing,” through internships, clinics, or cooperative experiences. Numerous academic studies have confirmed that having the chance to put learning into practice results in students that are more motivated, better educated, and better prepared for their careers (Hawtrey, 2007; Wingfield and Black, 2005). To provide experience managing money, Niagara University developed a class in the spring semester of 2008 to let their students manage money by investing a portion of the university’s endowment. Referred to as the Monteagle Fund, named for the ridge on which Niagara University is located, the Fund is a student managed investment fund. Managed by a class in the Niagara MBA program, the Fund realistically conveys to students the challenges of managing an investment portfolio on behalf of a client. In this case report, we review the challenges involved in setting up this type of class, the difficulty of investing during the financial crisis that began in 2007, and the effect that participation in the class had on students and their choice of careers.