Since the 1990s, colleges and universities throughout the United States have witnessed a substantial increase in student population demographics. In particular, upticks have been reported in the number of first-generation students enrolling in colleges and universities. There is evidence that first-generation college students often face insurmountable challenges not representative of their non-first-generation peers. Although there is substantive literature about the characteristics of first-generation college students, there is limited research uncovering pathways to a college or university presidency for this student population. The purpose of the study was to examine 12 individuals' unexpected path to a college or university presidency, important lessons learned, and factors that differentiate first-generation college presidents. A list of themes was used to organize each participant's story and capture major insights. Collaterals (chancellors, board chairs, search committee chairs, or mentors) were used to triangulate/corroborate data and highlight the qualities and needs of first-generation college presidents. An interview protocol was used to capture the rich stories of first-generation college presidents. A first-generation college student was defined as one whose parents have not earned a bachelor's degree prior to their children and/or extenuating circumstances exist that prevent the parents from exerting influence over their children's decision whether to attend college. A comprehensive list of first-generation college presidents was compiled purposefully to select participants. Face-to-face, Skype, Zoom, and telephone interviews were conducted using open-ended questions. Hermeneutic phenomenology was the theoretical framework used to describe first-generation college presidents' stories/experiences. The profile of college and university leadership continues to reflect a homogenous pool of white males in their early sixties. Existing research has found that a staggering percentage of these presidents are expected to exit the presidency in the next few years, thus creating opportunities to diversify the presidential pipeline. First-generation college students' drive and grit may provide the capital to address the vacancy. Results of the investigation showed that participants either benefited or realized the benefits of mentorship, professional development, and sponsorship during their ascension to the presidency. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]