Transitioning from high school to college is a challenging time for young adults and can be more difficult for first generation students. In some cases, adolescents are assisted by community assets (coaches, teachers, church/family members) and community-based leadership education programs. This combination may provide youth with critical skills to navigate the collegiate environment. The authors interviewed eight adult men of color who had participated as adolescents in a cohort-based, six-month life-skill development program. The goal was to identify attributes of the program that aided in their transition to college by examining the findings through the lens of Yosso's (2005) community of cultural wealth model. The findings suggest that the structured program along with other disclosed community assets positively influenced these students' choices to enroll in college and provided necessary skills needed to navigate their first year of college.