· This article explores the Skillman Foundation’s shift in its approach to fulfilling its mission to improve the lives of children and youth and to making grants – moving from a traditional grantmaker to a place-based investor and change-maker. · Three aspects of Skillman’s approach have directly shaped the evolution of its youth-development investments: recognizing Detroit’s economic, social, political, and environmental challenges; articulating overarching goals to provide direction and setting priorities for the scope and focus of its programmatic work; and using rapid learning to inform strategic decisions and social-innovation practices designed to tackle deeply entrenched problems. · This article reflects on the foundation’s evolution...