Bill Flagg is a seasoned entrepreneur who built five thriving tech businesses before seeking a simpler life in Portugal. In their conversation, Bill shares his journey from intense entrepreneurship to a place of creativity and inspiration. He discusses the emotional turmoil of his post-exit identity crisis and the challenges of letting go of past achievements. Emphasizing the importance of introspection, he reflects on finding joy in simplicity and the fulfillment that comes from embracing uncertainty and living authentically.