Educational inequality resulting from wealth disparity leaves many students from low-income families unprepared for college or career. While this problem affects the entire nation, the 80-mile corridor between Aspen and Parachute in western Colorado exemplifies these inequality issues. In this region, over half of children are not ready for kindergarten, and only 73 percent of low-income youth graduate high school. Recognizing that this problem reached beyond the classroom, the Aspen Community Foundation (ACF), under the direction of Tamara Tormohlen, launched the Aspen to Parachute Cradle to Career Initiative (CCI) in 2012. CCI brings together the non-profit, public, and private sectors to pursue four high-level goals: Goal 1: All Children Should be Ready for Kindergarten; Goal 2: All Children Should Develop Social and Life Assets for Success and Happiness; Goal 3: All Children Should Succeed Academically; Goal 4: All Youth Should Graduate High School Ready for College and Career. With former Aspen Mayor John Bennett now serving as CCI’s Director, CCI has instituted community enrichment programs for 1,400 K-8 students, two pre-kindergarten “jumpstart” programs for at-risk children, and two mobile “preschools on wheels” reaching 120 underserved children.