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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. words.paulollinger.com

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Can You Fake Happiness? w/Beth Cabrera

“People do not decide their futures: they decide their habits and their habits decide their future.” – F.M. Alexander If you want to improve, be kind to yourself. That’s the message from this week’s guest, Dr. Beth Cabrera, a positive psychologist, professor, and author of the new book Being Well: A Positive Path to a Healthier, Happier You . Beth is also an old college friend who's now the first…

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Freeze the Rent! And Other Silly Policies ( w/ Paula Pant)

Last week, I received a bill from New York City for $71,1783.16. It was the balance due for my Non-primary residence surcharge, aka the pied-à-terre tax that is a premium on top of the $55k or so we pay in regular, old fashioned property tax. We got pinged because our home is owned by our trusts, which are not New York entities. The good news is that, since we are legit full-time residents, we…

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Nobel Prize Winner on "Moral Economics"

This week, I sit down with Dr. Alvin Roth, Nobel Prize-winning economist, Stanford professor, and author of Moral Economics: From Prostitution to Organ Sales, What Controversial Transactions Reveal About How Markets Work . Al lays out why so-called repugnant markets like kidney sales, prostitution, horse meat aren't moral failures so much as trade-offs we refuse to name, and argues we should judge…

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How Empathy Is Destroying Western Civilization (with Gad Saad)

In this episode of Reasonably Happy, I sit down with Dr. Gad Saad, an evolutionary behavioral scientist, longtime professor, and author of the New York Times bestseller Suicidal Empathy: Dying to be Kind . Gad lays out why empathy, when it hyper-fires at the wrong targets, becomes a form of civilizational self-disembowelment. We cover open-border immigration, cultural relativism, the UK grooming…

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The Richest Family You've Never Heard Of

Investment management firm Fidelity is a private company that administers over $18 trillion in assets—that’s greater than the GDPs of Germany, Japan, the United Kingdom, and France combined . (Or, it’s18 Elon Musks.) Last year, the company earned almost $13 billion in profit , half of which goes to the family who started it. To be more precise, it goes to the founder's grandchildren, a few of whom…

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TRIGGERnometry's Francis Foster on Teaching, Comedy, and Why the U.K. is Fucked

Francis Foster is the co-host of the massively popular TRIGGERnometry podcast and author of the new book (Un)Educated: My Life as a Teacher, and Why You Should Never Become One (which you should buy here ). In this honest, fun, and sometimes stark conversation, Francis and I discuss: * Why teaching is a terrible job. * What he loves about TRIGGERnometry * His love for Buc-ees* (which are closer to…

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W. Kamau Bell on Cosby, Comedy, and Father's Day

I was most pleased to speak this afternoon with W. Kamau Bell, a Peabody Award and 4-time Emmy-winning comedian, filmmaker, and television host who is also a Celebrity Jeopardy champion! He is best known as the creator and host of CNN’s United Shades of America on which he spent seven seasons traveling the country exploring communities, subcultures, and perspectives that often go overlooked. The…

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5 Questions with Bruce Feiler

Thanks very much to Bruce Feiler for joining me on the 5 Questions livestream to discuss his new book A Time to Gather: How Ritual Created the World—and How it Can Save Us . In this upbeat and positive conversation, Bruce and I discuss: • What came first, ritual or religion? • Why SEC football tailgating fits the definition of ritual • How Balinese tooth-filing ritual has much in common with…

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5 Questions with Andy Borowitz

On this third episode of 5 Questions, I speak with Andy Borowitz , whose massively popular newsletter The Borowitz Report tops out around 200 words per post. So this intro is going to be brief! Even if you belong to Andy’s army of loyal readers, you might not know that he is also the co-creator of The Fresh Prince of Bel-Air and wrote on classic 80’s TV shows, The Facts of Life and Square Pegs ,…

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A Political Family Black Sheep Tells All (with Rosebud Baker)

My guest today is Rosebud Baker. Rosebud is one of the sharpest and most honest voices in comedy today. She’s an Emmy-nominated and Writers Guild Award-winning writer whose credits include Saturday Night Live , Inside Amy Schumer , and That Damn Michael Che . In her new autobiography, Fully Baked: A Messy Memoir, Rosebud shares the story of being the grand-daughter of James Baker, the former…

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5 Questions with A.J. Jacobs

✍️ Follow Paul Ollinger on Substack by clicking here ✍️ A.J. Jacobs is a journalist, bestselling author, self-described “human guinea pig,” and one of the most interesting people I know. He was a great choice to be my second guest on my 5 Questions series of Substack livestreams. Over the past two decades, A.J. has built a remarkable career by asking questions most of us would never think to…

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