Informed by the experiences of former peer mentors, this qualitative study examines the structure of opportunity of a university retention program. Extending the concept of social capital, the study investigates the experiences of students who served as peer mentors, and how their involvement in the retention program has influenced their social and academic development while in college. Findings suggest that employing peer mentors can be mutually beneficial to retention efforts since the peer mentors were trained to demonstrate aspects of advocacy, role modeling, and acting as human bridges for the program participants while also benefiting from those very forms of institutional support embedded in the program structure. Specifically, peer mentors developed important peer-to-peer and peer-to-staff social relationships that aided in their own retention.