In this inspiring conversation, entrepreneur and author Chip Conley shares his journey from founding a boutique hotel chain at age 26 to becoming a transformative mentor at Airbnb. He reflects on the importance of "right-sizing" ego, embracing intergenerational learning, and finding purpose in midlife. Chip introduces the concept of being "useful" rather than "used up," a theme central to his book Midlife Manifesto, and discusses the creation of the Modern Elder Academy a wisdom school for midlife transformation. The dialogue explores how aging can be a time of growth. This is how AI interacts with human wisdom, and how community and connection are essential to longevity. Chip also reveals his latest passion, disrupting senior living through regenerative communities. Packed with insights, humor, and heartfelt stories, this conversation is a must-watch for anyone curious about living a deeper, more meaningful life at any age.