Through using a Positive Youth Development framework and culturally based education program, Konaway Nikka Tillicum Native American Youth Academy aspires to mentor and prepare Native youth through high school and on to higher education. This collaborative research partnership investigated cultural identity, self-esteem, and academic optimism of Native American youth attending the academy. The results of this program evaluation found that cultural identity, self-esteem, and academic optimism were all closely related to each other as well as that they increased significantly when measured before and after the academy. GPA was found to not be predictive of cultural identity, self-esteem, or academic optimism prior to students attending the academy. Lastly, the relationship between cultural identity and academic optimism appeared to be explained through the indirect effect of self-esteem. The results suggest that culturally based education and positive youth development programs such as Konaway are efficacious in increasing protective factors among Native American youth.