This study was designed to explore, record, explain and describe the lived experiences of African American male students engaged in mentorship programs for post-secondary education. This study takes an exploratory phenomenological approach to research and is conducted at a mentorship program site. The following research questions guided this study and provided insight into participant's experiences: 1. How do Black males describe their experience in a holistic mentorship development program that prepares them for post-secondary educational success? 2. How were aspirations for post-secondary education cultivated among Black male students who are currently enrolled in high school and entering their first year in college? 3. How do African American male collegians overcome boundaries and continue to earn degrees, despite racial stereotypes, transition issues, academic under-preparedness, and other negative forces? The phenomenological methodology's emphasis on lived experience drove this study's data collection and assessment of a subset of 10 participants that included both mentors and mentees. Participants in this study participated in one-hour interviews that were later analyzed to develop an understanding of the participant's experience with mentoring. A guided interview structure was used to elicit a detailed description of each participant's experience. The interviews were composed of both semi-structured and open-ended questions. Using this approach, phenomenological reduction and imaginative variable processes were deployed to create textual and structural descriptions from each participant's experience. From this study, the following themes emerged: (a) societal influences; (b) family & health; (c) friendship & role models; and (d) personal and professional development. This study finds that mentorship has a profound impact on African American men in their journey through high school and college. Many participants reported that their successes and drive to pursue higher education were instilled by guidance, coaching, and friendship that was provided in mentorship programs. This study concludes with a number of recommendations for educational stakeholders, including public school leaders and non-profits that wish to better serve African American men in college and throughout their careers for personal and professional success. [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.]