Daniel Robbins sits down with John Glaser for a wide ranging conversation on rebellion, reinvention, leadership, and a life built far outside the conventional path. Drawing directly from the transcript, John reflects on getting expelled from high school, hitchhiking from Alaska to Panama, going to clown school, and eventually becoming a leading voice in digital health and an executive in residence at Harvard Medical School. The episode becomes a deeper meditation on love, family, courage, meaningful work, and why the journey itself matters more than the applause at the end.