Significant resources have been directed at understanding and alleviating the achievement gap in education. Most programs focused on this aim rely on a top-down approach, including funding for infrastructure improvement, curriculum development, class size, and teacher salaries. This article presents findings from a randomized field trial that evaluates a bottom-up approach in which high-achieving students of diverse racial and ethnic backgrounds from poor families are given monetary incentives to maintain their academic standing. The evaluation was designed to explore the role of monetary incentives as a mechanism for promoting resiliency in the face of poverty-related challenge. Discussion of what motivates students to learn is framed as a function of normal cognitive and socioemotional development in challenging environments. Evaluation findings indicate that monetary incentives are effective in promoting academic success to different degrees and for different reasons depending on students' perception of the meaning of the incentive in relation to their emergent identity.