Student persistence to graduation remains a critical measure of institutional success. Degree attainment is not only essential to the personal achievement of students arriving on campus each fall but has become a high-stakes measure for performance-based funding. It is telling, that even now, the pursuit of a college degree is characterized as replete with challenges. Yet, despite the multitude of conceivable barriers, many students represent the best hopes and aspirations of their families; some as the potential firsts to realize the numerous advantages afforded by a college degree. A student's performance either solidifies first-year achievement and persistence toward Year 2 or results in academic failure and stop-out. How do faculty and administrative leaders at Historically Black Colleges and Universities (HBCUs) uniquely influence the trajectory of the students they shepherd? What is the impact of motivation as particularly expressed and experienced in the HBCU environment? This article offers an HBCU-specific view from campus faculty and administrators. Particular attention is given to an account of motivation and reflections as former students and resulting influences on student interaction and instructional approaches.