Today, Jay sits down with legendary filmmaker and comedian Judd Apatow, known for shaping modern comedy with films like The 40-Year-Old Virgin and Knocked Up. Judd opens up about the struggles behind the success, sharing how self-doubt, early failures, and rejection shaped him into the storyteller he is today. Judd talks about the risks he took, the creative experiments that didn’t work, and how those “failures” became stepping stones toward lasting impact. He reveals how therapy, mindfulness, and even family dynamics have influenced his work, and why the most meaningful measure of success is not box office numbers, but whether your work truly connects with people.