A collaborative at several sites across the state of California will offer evidence of how successful linked learning, which connects academics to real-world work, can be. This article presents examples that illustrate the powerful connections and linkages that are generated by combining academic rigor with the relevance of applying learning to real-world work and careers. The connection is compelling not only to students, but to teachers, industry, and funders as well. The article also presents highlights that describe challenges, successes, and lessons learned from the work of the Alliance for Regional Collaboration to Heighten Educational Success (a statewide organization) with six regional collaboratives as they plan and implement linked learning approaches in specific school sites, with the support of the Irvine Foundation.