Only 11% of students who are Pell-eligible and the first in their family to attend college graduate with a bachelor's degree. Upward Bound is a federal-funded project that seeks to: (1) improve the motivation and skills of disadvantaged students; and (2) increase students' likelihood of success at two- and four-year institutions. The study sought to understand how a specific Upward Bound program helped facilitate college readiness for economically marginalized Black students through the lens of the participants. The data for this project was collected through interviews with current and former participants. The findings revealed that familial-like relationships between the staff and students were the pillars of the program's success. Having adult mentors created a climate of empowerment and high self-esteem for the students aspiring to attend and be attain success in their collegiate pursuits. Pairing mentorship with the financial means to remove structural barriers in education through grant funds, cultivated outcomes that produced college entry and completion. These findings indicate a need for intentional college-to-career efforts that support post-secondary goals of students to include: identifying adults and college students to serve as mentors, training staff to embrace ideologies that work to combat structural barriers in education, and building relationships with local colleges and universities to utilize free resources and be abreast on admission trends. [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.]