S12, Ep45 Part 2: Paul Ollinger: From Facebook Exec to Stand-Up & Being Reasonably Happy

Making his Next on the Tee debut is comedian, author, and former Facebook executive Paul Ollinger. Paul is the host of The Reasonably Happy Podcast and the author of Reasonably Happy: Essays on Money, Work, and Other Things That Piss Me Off. Before turning to stand-up comedy and writing, Paul served as VP of Sales at Facebook, leading one of the most successful teams in the tech world.

In our conversation, Paul shares the story behind his unlikely journey—from corporate boardrooms with Mark Zuckerberg to comedy clubs where the only bottom line is laughter. He talks about the moment he decided to leave the corporate grind for the stage, the lessons he’s learned from both worlds, and what “reasonable happiness” really means. We discuss how much financial stability you need before chasing a dream, why fear and money often hold people back, and how to take that first step toward a more fulfilling life.

Paul also shares insights from his book, including why Denmark consistently ranks as one of the world’s happiest countries, what our pandemic obsession with toilet paper says about us, and the humor behind a chapter titled Nightmare on the Back Nine. And yes—he even confesses how his golf index jumped after buying a Jailbird putter.

It’s a fun, thoughtful, and inspiring conversation with a man who’s lived life on both sides of success—and learned that happiness isn’t about what you earn, but what you love doing.