Reasonably Happy with Paul Ollinger
Reasonably Happy with Paul Ollinger

Reasonably Happy with Paul Ollinger

Paul Ollinger

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Episodes

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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

Recent Episodes

The Fragile Power of Wealth
APR 30, 2026
The Fragile Power of Wealth
<p>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 <em>Fragile Power</em>, 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.</p><p>✍️ Subscribe to Paul’s Substack <a target="_blank" href="https://words.paulollinger.com/">here</a>. ✍️</p><p>📈Rate Reasonably Happy <a target="_blank" href="https://ratethispodcast.com/paulopod">here</a>.📈</p><p>👀 Learn More about Dr. Paul <a target="_blank" href="https://drhokemeyer.com/">here</a>. 👀</p> <br/><br/>Get full access to Reasonably Happy at <a href="https://words.paulollinger.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_4">words.paulollinger.com/subscribe</a>
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1 MIN
Millionaires v. Billionaires in NYC
APR 2, 2026
Millionaires v. Billionaires in NYC
<p><strong>Chris Pavone</strong> is the bestselling author of some of the smartest and most stylish thrillers of the past decade. His latest book, <em>The Doorman</em> 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, <em>The Expats</em>, 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 <em>The Accident</em>, <em>The Travelers</em>, and <em>The Paris Diversion</em>—known for their globe-trotting settings, psychological depth, and characters navigating secrets, ambition, money, and power. </p><p>✍️  Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ <a target="_blank" href="https://ratethispodcast.com/paulopod">HERE⁠</a>  (DO IT!) ✍️  </p><p>📚 Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ <a target="_blank" href="https://words.paulollinger.com/">HERE</a> 📚</p><p>🗽 Order 'The Doorman' book <a target="_blank" href="https://www.amazon.com/Doorman-Novel-Chris-Pavone/dp/0374604797">HERE</a>. 🗽</p><p>🚩 Follow Chris Pavone <a target="_blank" href="https://substack.com/@chrispavone">on Substack</a> 🚩</p> <br/><br/>Get full access to Reasonably Happy at <a href="https://words.paulollinger.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_4">words.paulollinger.com/subscribe</a>
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66 MIN
The Beatles, Ted Turner, and Ric Flair with Steve Chamberlain
MAR 26, 2026
The Beatles, Ted Turner, and Ric Flair with Steve Chamberlain
<p>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. </p><p>I originally wanted to talk to Steve because of his experience leading the go-to-market plan of <em>The Beatles Anthology</em>, one of the most commercially successful recording projects of all-time. It was to be the follow-up episode to <a target="_blank" href="https://words.paulollinger.com/p/money-fame-and-misery-meet-the-beatles">last week’s interview</a> with Peter Doggett, author of '<em>You Never Give Me Your Money: The Beatles After the Break Up</em>'.</p><p>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.”</p><p>Steve oversaw the 50th Anniversary celebrations for both <em>Gone With the Wind</em> and <em>Casablanca</em>, then—after Turner— went on to captain the release of Frank Sinatra’s <em>Duets</em>, which eventually led to his work with the Fab Four.</p><p>Check it out here or wherever you get your podcast love.</p><p>✍️ Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ <a target="_blank" href="https://ratethispodcast.com/paulopod">HERE⁠</a> (DO IT!) ✍️</p><p>📚 Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ <a target="_blank" href="https://words.paulollinger.com/">HERE</a> 📚</p><p>#music #movies #film #marketing #beatles #entertainment #TedTurner #wrestling #ricflair</p> <br/><br/>Get full access to Reasonably Happy at <a href="https://words.paulollinger.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_4">words.paulollinger.com/subscribe</a>
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61 MIN
Money, Fame, and Misery: Meet the Beatles
MAR 19, 2026
Money, Fame, and Misery: Meet the Beatles
<p><strong>Money, Fame, and Misery: Meet the Beatles (w/ Peter Doggett )</strong></p><p>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 <em>You Never Give Me Your Money</em>, 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 <em>Rolling Stone</em>, <em>Mojo</em>, <em>Q</em>, 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 <em>Surf's Up: Brian Wilson and The Beach Boys</em>. Btw, if you like this episode, you’ll also love the new Amazon documentary about Paul McCartney called <em>Man on the Run</em>. Check it out.</p><p>  Please ⁠rate and review⁠ ⁠⁠Reasonably Happy⁠ <a target="_blank" href="https://ratethispodcast.com/paulopod">HERE⁠</a>  (DO IT!)   </p><p> Read ⁠Paul’s ⁠⁠Substack newsletter⁠⁠⁠ <a target="_blank" href="https://words.paulollinger.com/">HERE</a> </p><p> Order Peter’s book <a target="_blank" href="https://www.amazon.com/You-Never-Give-Your-Money/dp/0061774189/ref=sr_1_1?crid=3CJW5PSPP9J00&#38;dib=eyJ2IjoiMSJ9.e2gDedg_1ZNRK9SYFV0OUJEqyi3m3wQGIg-2KyKdmI5yFePl14vZZNOnDDH_BAOqov38IMlEKsydBQOv8EHdv0ya457BtxnC4GFsElZV0k66YkI3R5SD3WtrZveKdk9iq_VUDU7jSvRWnfugRuuHuWSUTDY_MfOAM5mBKHNEpUuFVbeq8lis3-8crpknSVS1xUXEiNPtFjTDuhxsVH-nHG9hClJhgUJvUrh1jJPvBYU.cLV87OJLxKS_2QrHjkQrdQ2_B0sAVZk51mBqoWHMngk&#38;dib_tag=se&#38;keywords=peter+doggett&#38;qid=1773579759&#38;sprefix=peter+doggett%2Caps%2C141&#38;sr=8-1">HERE</a>. </p> <br/><br/>Get full access to Reasonably Happy at <a href="https://words.paulollinger.com/subscribe?utm_medium=podcast&#38;utm_campaign=CTA_4">words.paulollinger.com/subscribe</a>
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58 MIN