Money, Family & Comedy w/Roy Wood Jr.

Money, Family & Comedy w/Roy Wood Jr.

Author: Paul Ollinger May 14, 2026 Duration: 56:44

✍️ Follow Paul Ollinger on Substack by clicking here ✍️

My guest today is Roy Wood, Jr. You know him from The Daily Show and from his acclaimed stand-up specials, where he proves that smart comedy can still hit hard. A native of Birmingham, AL, Roy has that rare ability to make you laugh while also making you think—whether he’s talking about race, class, media, relationships, or the strange little hypocrisies we all live with. In addition to The Daily Show, Roy has performed on The Tonight Show, The Late Show with David Letterman, BET’s Comic View, Conan, and many other top TV programs. He is now the host of the CNN current events-comedy show, Have I Got News for You. His 2025 memoir, The Man of Many Fathers explores—among other things—Roy’s complicated relationship with his father, Roy Wood, Sr., a civil rights journalist and African American radio pioneer.

Today, Roy and I talk about money, family, fatherhood, and we go deep on the craft of comedy.

Speaking of comedy, see my upcoming shows below. Save the date / buy your tickets!

COMEDY NEAR YOU - GET YOUR TICKETS!

* May 16: QED, Astoria Queens, 9:30

* May 20: Dunwoody Country Club (members only)

* May 21: Atlanta Punchline - ON SALE

* May 22-23: DC Comedy Loft ON SALE

* June 4: Atlanta Athletic Club (members only)

* June 19-20: Comedy Catch, Chattanooga ON SALE

* June 25: Couples Therapy Comedy at West Side Comedy Club, NYC

* July 21: The Venice West, Los Angeles - On Sale soon

* July 23: Cobbs Comedy Club, San Francisco - ON SALE

* Aug 1: Sticks and Stones Comedy Club, Southampton, NY -

* Aug 8: Atlanta Country Club (members only)

* Aug 13-16: Headlining McCurdy’s in Sarasota, FL - ON SALE

* October 15: Capital City Country Club (members only)



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Paul Ollinger has worn a few different hats-stand-up comedian, tech executive, and now, the curious host of Reasonably Happy with Paul Ollinger. This isn't a lecture series or a dry self-help guide. Instead, it feels more like pulling up a chair for a series of genuinely engaging talks that wander into the places where our daily lives, careers, and inner worlds collide. The conversations, which feature authors, thinkers, and various creatives, are refreshingly candid. They dig into the practical and philosophical questions about what it actually means to build a life that feels both successful and satisfying. You'll find that each episode of this podcast approaches big themes-money, purpose, and the pursuit of contentment-with a blend of wit and thoughtful depth. The underlying idea isn't about finding a perfect, Instagram-ready version of happiness, but something more grounded and attainable. It's for anyone who's ever wondered if there's a smarter, more meaningful way to navigate the pressures of business and culture without losing sight of what matters. Tuning in, you get the sense that Paul is figuring it out alongside his guests, making the insights feel earned and relatable. The result is a consistently interesting exploration of how we can all aim for a life that feels reasonably, and authentically, well-lived.
Author: Language: English Episodes: 100

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