There is much debate about the survival and future of small, private, nonprofit colleges and universities in the United States. Most of them are facing fiscal austerity and their long-term financial sustainability is being questioned. This is in part because of the demographic, technological, regulatory, and other challenges that are impacting higher education but, more important, because small institutions are primarily tuition-revenue dependent. Without being able to secure their financial futures, small, private colleges and universities may not be able to fulfill their unique missions and key roles in society. To ensure their survival, it is imperative that they devise new approaches to doing business. The purpose of this study was to uncover innovative approaches to revenue diversification for small, private nonprofit colleges and universities. It examined why and how leaders at these institutions engaged in such approaches and the challenges they faced in their decision-making processes. A multiple case study research methodology was used to frame the research. It focuses on a sample of three institutions—Babson College, Wellesley, Massachusetts; Butler University, Indianapolis, Indiana; and Denison University, Granville, Ohio—that have demonstrated significant improvement in their revenue streams in the past five years due to their institutional commitment to innovation. A qualitative research method through semistructured interviews of senior leaders in strategic and operational positions at these institutions captured the lived experiences of the individuals directly involved in the innovation initiatives and revenue strategies. This study has attempted to contribute to the field of higher education in two ways. First, the findings from this study may be used as practical key takeaways for senior leaders at small, private colleges and universities who seek to strategically engage in innovative ways to create sustainable financial futures for their institutions. Second, this study has contributed to the body of literature that lies at the intersection of academic business-model innovation, revenue diversification, and institutional decision making for small, private colleges and universities.