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This study focuses on 23 first- and second-generation Latino male college students’ reflections on the “who” and “what” helped them enroll in selective colleges. Latino male students have strong aspirations to enroll in college but have limited access to college knowledge and structural support. Using community cultural wealth and validation theory, this study explores how Latino male students perceived the role counselors had in supporting their college pathways. Drawing on life-history methods, findings show Latino male participants attributed their preparation for selective institutions to their high school counselors. Additionally, the second-generation Latino male students had similar experiences as first-generation Latino male students. This study challenges conventional ideas of available resources of Latino male students in preparation for selective four-year institutions.