159: Laughing All the Way to Rock Bottom (Then Back Up) with Paul Ollinger

Paul Ollinger quit his job at Facebook to chase his comedy dream. (Don’t ever do that.) This highly unprofitable decision has allowed him to headline major clubs like Carolines on Broadway, Cobbs (SF), and Zanies (Nashville and Chicago). He has performed at the Hollywood Improv and Comedy Cellar, and headlined his own show in the 2024 New York Comedy Festival. Paul is the host of the Reasonably Happy podcast, on which he explores the connection between money, happiness, work, and meaning in conversations with some of the world’s most interesting people. Previous guests include LL COOL J, Deepak Chopra, Judd Apatow, Paul Shaffer, and winners of the Nobel Prize, Heisman Trophy, and Olympic gold medals. He has just published a collection of essays, also titled Reasonably Happy, in which he shares humorous, thoughtful, and sometimes touching insights from over 200 of these interviews. Podcast Sponsor: Summit Leadership Group Summit Leadership Group transforms organizations by developing bold, agile leaders who inspire performance and lead with purpose. Through tailored coaching and immersive training, we ignite lasting growth where it matters most—at the intersection of people, culture, and results. To know more about Paul visit his website: www.paulollinger.com