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. 3D AGO

    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

    1h 6m
  2. 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 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

    1h 1m
  3. 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.  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

    58 min
  4. 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. 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

    58 min
  5. Gina Gershon on Fame, Desire, and Boobs

    MAR 5

    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 P***y: 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

    1h 1m
  6. The Courage to Be Right w/ Matt Kaplan

    FEB 26

    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

    58 min
  7. Insider Trading w/Tom Hardin

    FEB 19

    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

    1h 14m
  8. Surviving Middle Age w/ Ben Markovits

    FEB 12

    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

    48 min
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4.9
out of 5
441 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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