
Reasonably Happy with Paul Ollinger
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.
Paul Ollinger
Show overview
Reasonably Happy with Paul Ollinger has been publishing since 2019, and across the 7 years since has built a catalogue of 333 episodes. That works out to roughly 290 hours of audio in total. Releases follow a weekly cadence.
Episodes typically run thirty-five to sixty minutes — most land between 47 min and 59 min — and the run-time is fairly consistent across the catalogue. It is catalogued as a EN-language Comedy show.
The show is actively publishing — the most recent episode landed 1 weeks ago, with 24 episodes already out so far this year. Published by Paul Ollinger.
From the publisher
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
Latest Episodes
View all 333 episodesW. Kamau Bell on Cosby, Comedy, and Father's Day
5 Questions with Bruce Feiler
5 Questions with Andy Borowitz
A Political Family Black Sheep Tells All (with Rosebud Baker)
5 Questions with A.J. Jacobs
I Read My Essays to You
5 Questions with Dave Barry
Gretchen Rubin Will Teach You to be Happy
Money, Family & Comedy w/Roy Wood Jr.
How to Get Rich in America
The Fragile Power of Wealth
Surviving the Loss of a Child

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 🚩 This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit words.paulollinger.com/subscribe

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 This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit words.paulollinger.com/subscribe

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. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit words.paulollinger.com/subscribe

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-believersNir 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. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit words.paulollinger.com/subscribe

Gina Gershon on Fame, Desire, and Boobs
Guess who I got to meet last week - Gina Gershon. That’s right, the incredibly beautiful and talented actress, author, singer, and long-standing disruptor of polite expectations. You know Gina from unforgettable roles in Bound, Showgirls, Face/Off, Cocktail, and a career that has zig-zagged fearlessly between Hollywood glamor, indie grit, Broadway, and music. We talked about her work and life as recounted in her new memoir, 'Alpha Pussy: How I Survived the Valley and Learned to Love My Boobs’ (a title that caught the attention of my 16 year-old son and, well, me). Gina shares stories about Prince, David Mamet, Paul Thomas Anderson, Robert Altman, Michael Mann, and Lou Reed. And she spills the beans about kissing both Tom Cruise and Jennifer Tilly (I’d go with Jen, personally). Oh, she also tells why it was so much fun to improv with Larry David on 'Curb Your Enthusiasm’. Need I say more? Okay, yes - just a little: What I took away from this interview is that artists like Gina who prioritize freedom above commerce sometimes miss out on millions of dollars and a degree of “stardom,” but they maintain their sense of self and Alpha vibe. Check it out. Please rate and review Reasonably Happy HERE (DO IT!) Read Paul’s Substack newsletter HERE Buy Gina's book HERE. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit words.paulollinger.com/subscribe

The Courage to Be Right w/ Matt Kaplan
Matt Kaplan is a science correspondent at the Economist and author of the new book I Told You So!: Scientists Who Were Ridiculed, Exiled, and Imprisoned for Being Right in which he shares the stories of researchers—from Darwin to Pasteur to modern Nobel Prize winners—who had to fight for their revolutionary ideas to be accepted. "But Paul…” you might say. "This sounds very interesting, but how does it fit into the conversations here on Reasonably Happy?” Good question! It’s because I like contrarians and truth-seekers. I worry about prevailing power structures or narratives that restrict innovation, progress, free markets, and personal liberty, whether those obstacles be bureaucracy, fascism, religion, or political correctness. And perhaps by pondering these historical examples, we’ll be less likely to repeat past mistakes. Over the last two decades, Matt has written about everything from paleontology and parasites to virology and viticulture. In addition to the Economist, his writing has appeared in National Geographic, Nature, and the New York Times. He completed a thesis in Paleontology at Berkeley, and one in science journalism at Imperial College, London. In 2014 he was awarded a Knight Fellowship to study at MIT and Harvard. Born in California, he lives in England. Please rate and review Reasonably Happy HERE (DO IT!) Read Paul’s Substack newsletter HERE Buy Matt’s book, I Told You So! here. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit words.paulollinger.com/subscribe

Insider Trading w/Tom Hardin
How do you handle it when you screw up badly? (Like really badly.) Former hedge fund trader and Wharton graduate Tom Hardin was convicted of Securities Fraud and Conspiracy to Commit Securities Fraud, which are felonies. In 2008, during the beginning of the great finanical crisis, Tom desperately needed to put some points on the board at his fund. And since everybody else in the industry seemed to be doing it, Tom allowed himself to trade equities on material, non-public information—something he knew was illegal. After being stopped by the FBI on the streets of Manhattan, Tom agreed to become an informant and wore a wire over 40 times to aid the agency in its investigation of big fish like Steve Cohen of SAC who paid a $1.8 billion fine and Rajaratnam of of Galleon Group who went to jail for 7.5 years. I spoke to Tom this week about his new book, Wired on Wall Street: The Rise and Fall of Tipper X, One of the FBI’s Most Prolific Informants. A scrappy, middle-class kid from suburban Atlanta (Go Braves!), Tom willed himself into the University of Pennsylvania’s famed Wharton School of Business, which launched him into the finance industry. He eventually earned a seat at a prestigious hedge fund and was on his way until the intense pressure of the gig led him to make a terrible decision that earned him only $46,000 but ended his career. Today, Tom works with Fortune 500 companies, financial institutions, law firms, business schools, and leadership teams, delivering keynotes and advisory engagements on behavioral ethics, culture risk, and organizational conduct. NOTE: The actor in 'Traffic’ actor whose name I was trying to remember is Benicio Del Toro, not Guillermo Del Toro. Please forgive me.Please rate and review Reasonably Happy HERE (DO IT!) Read Paul’s Substack newsletter HERE Pre-order Tom’s book HERE. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit words.paulollinger.com/subscribe

Surviving Middle Age w/ Ben Markovits
Ben Markovits is the author of several acclaimed novels, including his most recent release The Rest of Our Lives, which explores marriage, infidelity, empty nesting, and mortality. The book, which was short-listed for the Booker Prize, focuses on a 55-year-old law professor’s midlife crisis and transformative road trip after his children leave home. You might say it examines the sources of happiness in our lives as we age. Ben’s writing has appeared in The New York Times, The New Yorker, and The Guardian. He spoke with me from his home in England.Please rate and review Reasonably Happy (DO IT!) Read Paul’s Substack newsletter Read Ben's book NYT essay This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit words.paulollinger.com/subscribe