Urban community leaders describe their perceptions of critical issues in education and offer recommendations for the creation of a college-going culture (CGC). This qualitative study employed a maximum entropy analysis. Results demonstrate critical issues with increasing educational attainment including complexity of the urban school system, limited traditional parental involvement, and self-acceptance among youth. This study emphasizes the importance of a CGC inclusive of the Community Cultural Wealth model, culturally sensitive teachers, and community-connected leaders. Research suggests that educational settings that value student's and families' Community Cultural Wealth can increase the number of students that matriculate through the educational pipeline.