Reasonably Happy with Paul Ollinger

Paul Ollinger
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Reasonably Happy is a podcast hosted by comedian and former tech executive Paul Ollinger who explores the intersection of money, meaning, and happiness through candid conversations with authors, thinkers, and creatives. With wit and depth, each episode offers insights into how we can lead more fulfilling lives—without chasing perfection. words.paulollinger.com

  1. 4D AGO

    Money, Family & Comedy w/Roy Wood Jr.

    ✍️ 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) Get full access to Reasonably Happy at words.paulollinger.com/subscribe

    57 min
  2. How to Get Rich in America

    MAY 7

    How to Get Rich in America

    ✍️ Follow Paul Ollinger on Substack by clicking here ✍️ “Capitalism is rigged!” cry the masses. “Nobody gets ahead anymore,” says the mainstream press. And 60% of young people believe that the American Dream is dead. But my guest today calls this hogwash, baloney, and complete malarkey. Joseph Moore is a historian, entrepreneur, investor, and the author of a new book called How to Get Rich In American History: 300 Years of Financial Advice that Worked (And didn’t) in which he explores how ambition, risk, and reinvention have shaped America from the very beginning. He also reveals the money myths, sacred cows, side hustles, and NAYsayers that have always been a part of our society. What if so-called timeless beliefs about money like “invest for the long run,” “compound interest builds wealth,” and “real estate always goes up” weren’t always true…and play out less often than you think they do. Joseph’s book is part history, part playbook, and part reality check. He brings lessons to life with rigor that is deeper than an oil well and a wit that is dryer than the Texas plains. And in so doing he demystifies the past in order to clarify the present for anyone thinking about money, success, and what it really means to “make it” in America. 📕 Follow Joseph here. 📗 Get full access to Reasonably Happy at words.paulollinger.com/subscribe

    1h 6m
  3. The Fragile Power of Wealth

    APR 30

    The Fragile Power of Wealth

    If you’ve ever wondered if having everything you’ve ever wanted would make you feel like a complete human being, this episode is for you. My guest today is Dr. Paul Hokemeyer, a psychotherapist who works almost exclusively with ultra-high-net-worth individuals—the kind of people most of us assume have life completely figured out. Spoiler alert: they don’t. Dr. Hokemeyer is the author of Fragile Power, a fascinating look at the emotional and psychological challenges that come with extreme wealth, fame, status, and success. In his work, he’s seen firsthand how money can insulate people from consequences, distort relationships, and quietly fuel addiction, anxiety, and isolation. In other words, he has a front-row seat to the uncomfortable truth behind the fantasy. Today, we talk about why power is more fragile than it looks, how wealth can complicate identity and purpose, and what it actually takes—whether you’re worth $10,000 or $10 billion—to build a life that feels meaningful. ✍️ Subscribe to Paul’s Substack here. ✍️ 📈Rate Reasonably Happy here.📈 👀 Learn More about Dr. Paul here. 👀 Get full access to Reasonably Happy at words.paulollinger.com/subscribe

    47 min
  4. Surviving the Loss of a Child

    APR 16

    Surviving the Loss of a Child

    “How am I ever going to be happy again?” That was the question the wife of this week’s guest asked him after the death of their one-month-old son, Fisher. Michael Cruz Kayne is a comedian, actor and a staff-writer on The Late Show with Stephen Colbert, where his work has earned him a Peabody Award, a WGA Award, and two Emmy nominations. He made his off-Broadway debut in Sorry For Your Loss, a raw, comedic, and deeply vulnerable one-man show about coping with a parent’s worst fear, the loss of a child. This is a sad but inspiring conversation. I found Michael’s attempt to make sense out of his grief and to honor Fisher’s brief life to be an uplifting act of service. You can watch the show starting March 27 on the Dropout network. ✍️ Subscribe to Paul’s Substack here. ✍️ 📈Rate Reasonably Happy here.📈 👀 Watch Sorry for Your Loss here. 👀 Get full access to Reasonably Happy at words.paulollinger.com/subscribe

    1h 4m

  5. APR 2

    Millionaires v. Billionaires in NYC

    Chris Pavone is the bestselling author of some of the smartest and most stylish thrillers of the past decade. His latest book, The Doorman is set in a glamorous Manhattan apartment building where the lives of the ultra-wealthy residents intersect with the man who quietly watches it all—the doorman. Over the course of one explosive day, secrets, class tensions, and personal betrayals collide in a fast-moving plot that doubles as sharp social satire about modern New York and the divides of race, wealth, politics, and status. This invites an inevitable and much-deserved comparison to Tom Wolfe’s Bonfire of the Vanities, though the Masters of the Universe are now fleece-vest-wearing tech and hedge-fund bros (not that there’s anything wrong with that). Full-disclosure: I loved this book. It's a page-turner! It's eminently-readable! But even more, it's an insightful look at modern society through the lens of New York City. Before becoming a novelist, Chris spent nearly two decades in book publishing, working on—or with—the editorial team for authors like John Grisham and Pat Conroy. Chris' debut novel, The Expats, became an international bestseller, won the Edgar Award and the Anthony Award for Best First Novel, and was translated into more than 30 languages. Since then he’s written a string of critically acclaimed thrillers—including The Accident, The Travelers, and The Paris Diversion—known for their globe-trotting settings, psychological depth, and characters navigating secrets, ambition, money, and power. ✍️  Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ HERE⁠  (DO IT!) ✍️   📚 Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ HERE 📚 🗽 Order 'The Doorman' book HERE. 🗽 🚩 Follow Chris Pavone on Substack 🚩 Get full access to Reasonably Happy at words.paulollinger.com/subscribe

    1h 6m
  6. The Beatles, Ted Turner, and Ric Flair with Steve Chamberlain

    MAR 26

    The Beatles, Ted Turner, and Ric Flair with Steve Chamberlain

    This week’s podcast is a conversation with my former Atlanta neighbor, Steve Chamberlain, a former media executive whose career has intersected with some of the biggest brands and celebrities in entertainment history. I originally wanted to talk to Steve because of his experience leading the go-to-market plan of The Beatles Anthology, one of the most commercially successful recording projects of all-time. It was to be the follow-up episode to last week’s interview with Peter Doggett, author of 'You Never Give Me Your Money: The Beatles After the Break Up'. And while Steve and I discussed this at length, I found his experience as an executive vice president at Turner Broadcasting in the 1980s even more interesting. Working directly for Ted Turner, Steve’s responsibilities included everything from home video to cable syndication and World Championship Wrestling. He shares a great story about utilizing 1-900 telephone numbers to monetize wrestlers' smack talk. It’s a fun insight into the early days of a pre-Internet media “start-up.” Steve oversaw the 50th Anniversary celebrations for both Gone With the Wind and Casablanca, then—after Turner— went on to captain the release of Frank Sinatra’s Duets, which eventually led to his work with the Fab Four. Check it out here or wherever you get your podcast love. ✍️ Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ HERE⁠ (DO IT!) ✍️ 📚 Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ HERE 📚 #music #movies #film #marketing #beatles #entertainment #TedTurner #wrestling #ricflair Get full access to Reasonably Happy at words.paulollinger.com/subscribe

    1h 1m
  7. Money, Fame, and Misery: Meet the Beatles

    MAR 19

    Money, Fame, and Misery: Meet the Beatles

    Money, Fame, and Misery: Meet the Beatles (w/ Peter Doggett ) In the late ‘60s, The Beatles had it all: worldwide fame, critical admiration, and more money than they ever could have imagined. So why were these four young men so miserable? (And often short of cash!) My guest today is Peter Doggett—one of the great rock music writers of our time, and a man who has spent decades studying what happens when ambition, fame, and enormous piles of cash—and drugs—collide. Peter is the author of You Never Give Me Your Money, a brilliant and deeply human book about the Beatles, not only at their creative peak, but also at their breaking point, when the most successful band in history discovered that unimaginable wealth and universal adoration do not, in fact, lead to contentment and enlightenment…but do lead to lawsuits, divorce, and—sometimes—heroin addiction. Peter has written for Rolling Stone, Mojo, Q, and many others. His work has this rare quality: it makes you love the music more while feeling slightly better about your own messy life. His latest book is Surf's Up: Brian Wilson and The Beach Boys. Btw, if you like this episode, you’ll also love the new Amazon documentary about Paul McCartney called Man on the Run. Check it out.   Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ HERE⁠  (DO IT!)     Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ HERE   Order Peter’s book HERE.  Get full access to Reasonably Happy at words.paulollinger.com/subscribe

    58 min
  8. Believe and You Will See! (w/ Nir Eyal )

    MAR 12

    Believe and You Will See! (w/ Nir Eyal )

    My guest this week is Nir Eyal, whose two books ('Hooked’ and ‘Indistractable’) have sold over 1 million copies in over 30 languages. This week he published his latest - Beyond Belief: The Science-Backed Way to Stop Limiting Yourself and Achieve Extraordinary Results. In our chat, Nir and I discuss: Why beliefs can help us perform at our top potential (or vice versa) The difference between facts, faith, and belief How beliefs can benefit us, even if they’re not “true” The importance of cognitive flexibility And, the power of prayer, even for non-believers Nir also shares a powerful story about the thing he learned by buying his mother birthday flowers from the “wrong” florist. Nir's work has been featured in the New York Times, Forbes, Harvard Business Review, Psychology Today, and many more. He attended The Stanford Graduate School of Business and Emory University. Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ ⁠HERE⁠⁠  (DO IT!) Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ ⁠HERE⁠  Learn more about Nir on his website. Get full access to Reasonably Happy at words.paulollinger.com/subscribe

    58 min
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442 Ratings

About

Reasonably Happy is a podcast hosted by comedian and former tech executive Paul Ollinger who explores the intersection of money, meaning, and happiness through candid conversations with authors, thinkers, and creatives. With wit and depth, each episode offers insights into how we can lead more fulfilling lives—without chasing perfection. words.paulollinger.com

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