Given the deficit and crisis narratives that dominate the discourse on Black males’ educational experiences and trajectories, more work is needed that attends to their strengths and assets and that also reveal new stories about their possibilities. The current study examines the college experiences of 65 Black men who participated in a Black Male Initiative (BMI) program at three different colleges. In particular, I use cultural capital as a frame to investigate how they made meaning and benefited from their BMI engagement. I discuss three specific ways that the men express and embody cultural capital: investing in self, uplifting the collective, and embodying leadership. Findings from this study provide empirical evidence for the importance of expanding and supporting alternate types of cultural capital for Black men, especially in the form of resistance capital and leadership capital, and better appreciating how these contribute to their collegiate experiences and personal development.