Reasonably Happy with Paul Ollinger

Latest Episodes:

5 Questions with Dave Barry May 28, 2026

Show notes

✍️ Follow Paul Ollinger on Substack by clicking here ✍️

Oh my goodness what a fun time I had chatting with Dave Barry on the first episode of 5 Questions, my bite-sized, live-streamed Substack interview show that I’ll be producing in addition to longer-form episodes of Reasonably Happy. Dave’s column was syndicated to hundreds of newspapers around the globe for several decades. He has published dozens of books on myriad topics that sold millions of copies—of books, not topics—in 22 languages. The New York Times called him “the funniest man in America.” (And when has the NYT ever been wrong?) In other words, he’s accomplished an incredible amount in the funny game, and I'm thrilled I got to talk to him. In this fast-moving 30 minute conversation, we talk about:

• What he’s looking for in a nursing home.

• Advice for me on shepherding my kids through the college search process (even though it doesn’t matter where they end up)

• The rock band he plays in with Stephen King, Amy Tan, Roy Blount, Jr., Scott Turow, and many other

• Which other authors make him laugh

• What Baby Boomers could learn from Gen Z (and vice versa)

Listen now and share with all your friends! Also, come see me tell jokes (or give a talk), in person:

* June 4 - Atlanta Athletic Club

* June 5 and 6 - Laughing Skull Lounge, Atlanta

* June 12 - Wade Hampton Country Club, Cashiers, NC (Talk)

* June 19 and 20 - The Comedy Catch, Chattanooga

* June 25 - Happy Couples Show, West Side Comedy Club, NYC

* July 21 - The Venice West, Los Angeles (on sale soon)

* July 23 - Cobbs Comedy Club, San Francisco

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

* Aug 8 - Atlanta Country Club

* Aug 13-16 - McCurdy’s Comedy Theatre, Sarasota, FL

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

Gretchen Rubin Will Teach You to be Happy May 26, 2026

Show notes

✍️ Follow Paul Ollinger on Substack by clicking here ✍️

“Happiness is a choice that requires effort at times.” -Aeschylus

Whenever I go back and re-listen to one of my podcast interviews, I always discover elements of the conversation I didn’t recall. Upon revisiting this 2025 conversation with best-selling author Gretchen Rubin, I of course remembered that she is a warrior for happiness and the practices that help her huge readership attain it. But listening again, I was struck by how cool Gretchen is. Not “cool” in a biker-jacket / beat poetry / clove cigarette way, but in the “I know who I am, what I’m committed to, and how I can add value to the world” way. I don’t claim to know Gretchen, but it seems logical to me that this self-awareness is a by-product of the kind of work she evangelizes. And it is work. As Aeschylus advised in the quote above, happiness is always there if we choose it, but only if—in the hard times—we are willing to get off the couch or smile through the pain. In times like these, Gretchen’s writing can help us find a path through the noise and, as she describes it, “identify ways we can take happiness from the transcendent to the concrete.” A great way to start that process is to listen (or re-listen) to this episode and take her happiness quiz here. You can also find many more applicable insights on Gretchen’s Substack, Secrets of Adulthood. Remember, happiness is growth—keep growing!

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Come see me (Paul) tell jokes (or give a talk), in person:

* June 4 - Atlanta Athletic Club

* June 5 and 6 - Laughing Skull Lounge, Atlanta

*June 12 - Wade Hampton Golf Club, Cashiers, NC

* June 19 and 20 - The Comedy Catch, Chattanooga

* June 25 - Happy Couples Show, West Side Comedy Club, NYC

* July 21 - The Venice West, Los Angeles (on sale soon)

* July 23 - Cobbs Comedy Club, San Francisco

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

* Aug 8 - Atlanta Country Club

* Aug 13-16 - McCurdy’s Comedy Theatre, Sarasota, FL

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

Money, Family & Comedy w/Roy Wood Jr. May 14, 2026

Show notes

✍️ 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

How to Get Rich in America May 07, 2026

Show notes

✍️ 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. 📗

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The Fragile Power of Wealth Apr 30, 2026

Show notes

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

Surviving the Loss of a Child Apr 16, 2026

Show notes

“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

Millionaires v. Billionaires in NYC Apr 02, 2026

Show notes

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

The Beatles, Ted Turner, and Ric Flair with Steve Chamberlain Mar 26, 2026

Show notes

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

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Money, Fame, and Misery: Meet the Beatles Mar 19, 2026

Show notes

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.

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Believe and You Will See! (w/ Nir Eyal ) Mar 12, 2026

Show notes

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

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