Jaime Fall sits down with us to discuss his plans for launching a $5 million digital upskilling initiative for the Economic Development Collaborative in Ventura County, California. After seven years as director of UpSkill America at the Aspen Institute, Jaime explains how he is using his past experience to build a portfolio of digital skills solutions for jobseekers and workers in Ventura. Jaime describes Ventura’s progressive plan to address three unique segments: Those who lack digital skills, workers who need improved digital skills for work, and small businesses who lack the digital skills to thrive or survive in an increasingly digital economy. His insights for planning these efforts can provide other communities with a framework for vying for funding under the Digital Equity Act. Jaime concludes with powerful insights on the importance of businesses that are offering no-cost online college options to their workers, which he sees as a transformative opportunity for millions who otherwise would not be able to afford college.