Michael Ovitz is the legendary co-founder of Creative Artists Agency, where he transformed Hollywood’s talent business and built the most powerful force in entertainment. In his time at CAA, Michael shaped the trajectories of artists, filmmakers, and companies, including actors Tom Cruise, Kevin Costner, Bill Murray, Sylvester Stallone, and Barbra Streisand, filmmaker Steven Spielberg, author Michael Crichton, talk show host David Letterman, the Coca Cola Company, and many, many more. Michael transitioned from entertainment to investing thirty years ago, advising Marc Andreessen and Ben Horowitz on the creation of a16z, and most recently, partnering with Ali Hamed as Chairman of Treville Capital Group. Ali has twice been a past guest on the show, and those conversations are replayed in the feed.

Our conversation begins with Michael’s formative influences from his upbringing, early lessons that shaped his relentless drive, and origins of CAA. We cover his fascination with creativity, CAA’s culture of empowerment, honesty, and momentum, and frameworks for building businesses, assessing talent, focusing on relationships, and learning from new industries.

We then turn to Michael’s recent work with Ali at Treville. We discuss the beginning of their partnership, the process of scaling, the building of momentum, and the systems that foster accountability, relentless follow-up, and refreshing of relationships. Michael closes with candid reflections on his mistakes and life lessons that continue to shape his remarkable path.