In an interview with Sylvester Henderson, Dr. Jo-Ann Rolle, a distinguished academic and former Dean of the School of Business at Medgar Evers College, discusses her extensive career in education and technology. She highlights her transition from an early career at IBM to a fulfilling academic path, emphasizing her commitment to underserved students. Dr. Rolle shares how she fostered experiential learning and raised significant funds to provide her students with international travel and competition opportunities, even for those facing severe challenges like homelessness. She also details her innovative approach to integrating technology in education, particularly during the COVID-19 pandemic, and her dedication to “bottom-up” publishing that makes academic work accessible to wider communities. Her focus consistently remains on equity and empowerment, striving to develop future leaders from diverse backgrounds through strong community partnerships and a belief in her students’ inherent potential.