Frustrated as a public high school teacher in Santa Cruz, California, Wes Beach started his own one-man high school, Beach High School (http://beachhigh.education). Over 25 years Wes has freed more than 1500 teenagers from compulsory schooling by rapidly graduating them and creating transcripts that allow them to immediately dive into college, career, or further self-directed learning. Wes and I recorded our interview in his home office (i.e., Beach High School headquarters) and discussed how he started his “shadow school” while teaching in the public system, the many paths his students have taken, what colleges want to see in nonconventional applicants, and the fundamental problems of compulsory education.