Over the past two decades First Generation African American (FGAA) males have been underrepresented in America’s colleges and universities. Nearly 67% of those enrolled, specifically at Historically Black Colleges and Universities (HBCUs), have failed to obtain a 4-year degree. Therefore, I utilized a phenomenological design with Astin, Spady, Tinto, and Bean as the theoretical frameworks. I interviewed six FGAA male students utilizing a series of three-interviews to understand their experiences at an HBCU (Seidman, 2006). In addition, I reviewed institutional documents such as the student code of conduct manual, campus activity bi-laws, and student transcripts, to compare the data obtained through the interviews. Data analysis utilizing memos, categorizing, connecting strategies, document analysis, and constant comparative method produced three themes: community and family influences on educational goals; responding productively to racism; and First Generation (FG) students reinventing themselves. The findings suggest FGAA male students are more likely to be successful because of resilience and persistence which helps them break down barriers. The findings also suggest although FGAA male students may start college at a disadvantage, special characteristics of persistence and resilience might benefit all African American (AA) male students.