This basic qualitative study examines the parental investment strategies of first-generation African American rural college graduates in cultivating college student success. Extant literature has demonstrated that the role of the family is necessary to support the college student and that the investment of the parent is paramount to student college completion. Although educational attainment is an important goal for African American rural residents, research detailing strategies that cultivated student college completion among this population is needed to fill the gaps in the literature. The objectives were to discuss communication, involvement, and factors of influence to determine how these parents transferred their educational beliefs to their children and supported them through college graduation. These stories of success were told through the eyes of first-generation parents and their second-generation adult offspring. Research detailing the parental investment strategies toward college completion is necessary to inform parents, educational institutions, and rural college student completion in postsecondary institutions of the strategies necessary to ensure college success in this population. Lieberman’s transgenerational theory, along with concepts extracted from parental investment as it relates to education, provided the conceptual lens for the study. Data collected through interviews and documents were analyzed utilizing content analysis. Ten semistructured interviews were conducted with parents and their adult offspring. Interviews gleaned the lived experiences of the participants. Data analysis revealed six themes: (a) Catch Them Early, (b) Set the Tone, (c) Keep Them Busy, (d) Don’t Let Them “Break Rank,” (e) Encourage Advancement, and (f) Tell the Generations. The findings support the importance of developing a family investment team, how a return on parental investment occurs, making use of rural extracurricular programming, and transferring positive beliefs regarding higher education.