There is an increasingly large disparity in college graduation rates among low-income and first-generation college students. Research suggests that the main reason for this discrepancy is the lack of access to information and knowledge about the college process. First-generation students have fewer people in their social network who went to college and thus cannot help them navigate the difficult and multi-step process of finding, applying, and enrolling in college. Mentoring, however, has been proven to be a successful intervention for helping these populations navigate the post-secondary process. This paper evaluates a school-based hybrid mentoring program to attempt to measure the relationship between mentors and how students in New York City navigated the post-secondary process and enrolled in college. Findings show that program lessons, number of months matched, and meeting out of program are important program elements in increasing a student’s likelihood of graduating high school and enrolling on-time in college.