This article takes an assets-based approach to study the educational aspirations of Latino males and their families, including extended family. While research has underscored the influence that Latina/o families have on their children's educational trajectories, this investigation demonstrates the reciprocity in relationships through the perspective of Latino males. Through funds of knowledge and familismo as guiding frameworks, the author highlights an optimistic and encouraging portrayal of Latinos and their families as rich information sources. Using a set of three in-depth interviews with each participant from a sample of 24 Latino collegians, the author presents four themes in the form of pairs to illuminate a two-sided transaction. The author offers a visual representation based on the findings to illustrate the cyclical and reciprocal relationship between Latino male college students and their families.