Native Hawaiian males are not attending college at rates comparable to other males in Hawai?i. Nearly 30 percent of the total male population in Hawai?i over the age of twenty-five hold a bachelor's degree or higher (OHA, 2017). When looking at Native Hawaiian men in this age group, only 15 percent hold a bachelor's degree or higher (OHA, 2017). This 50 percent gap between Native Hawaiian males and the state average for all males is substantial and worthy of investigation. This article comes from the author's larger dissertation work in which he conducted a qualitative study examining the motivating factors for Native Hawaiian male students pursuing postsecondary education at the University of Hawai?i -- West O?ahu. The study presented the perspectives of four successfully enrolled Native Hawaiian males and the factors that impacted their college enrollment decision and matriculation at a four-year postsecondary institution. The purpose of the larger study was to deepen understanding of the factors that influence Native Hawaiian males' decisions to pursue higher education in order to develop strategies to increase Hawaiian male entry and persistence in obtaining a higher education degree. Specifically, the author was and remains interested in the factors that influence low-income, first-generation, Native Hawaiian males from the Wai?anae coast of O'ahu educated through the public school system. The author writes that his hope is that the findings of the larger study will inspire a more nuanced and culturally sustainable perspective of Native Hawaiian males and college aspiration, persistence, and success.