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A paradox emerges upon close examination of corporate philanthropy: a record number of “generous” donations and historic levels of social inequality. Tech companies are placing significant investments in education, and many efforts to support Latino boys are aligned with these goals. I employ Critical Discourse Studies and Critical Social Theory to examine (1) how does the Bay Area tech boom shape the academic experiences of high-performing Latino boys? And, (2) how do high-performing Latino boys resist and/or become complicit in the Bay Area tech boom? I draw from an ethnographic study of high-performing Latino boys at an urban high school. Findings reveal the way students engage in delicate balancing acts between resisting and becoming complicit in the reproduction of inequality.