For generations in Black America, a college education was thought to be the silver bullet against poverty and a sure entryway to upward mobility and middle-class life. Rising college-associated costs coupled with falling incomes create a challenging scenario for some Black aspiring college students. This reality becomes more pronounced for first-generation prospects. Many of these first-time college students lack the financial resources or parental knowledge that can create a comfortable transition from high school to higher education. The 100 Black Men of South Florida, Inc. partnered with the Miami-Dade County Public School system to reverse this trend.