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Reasonably Happy with Paul Ollinger

Reasonably Happy with Paul Ollinger

De: 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.comPaul Ollinger
Ciencias Sociales
Episodios
  • Surviving the Loss of a Child
    Apr 16 2026

    “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. 👀



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    1 h y 4 m
  • Millionaires v. Billionaires in NYC
    Apr 2 2026

    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
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    1 h y 6 m
  • The Beatles, Ted Turner, and Ric Flair with Steve Chamberlain
    Mar 26 2026

    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
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    1 h y 1 m
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