Shows / Reasonably Happy with Paul Ollinger
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.
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Episodes
Reasonably Happy with Paul OllingerFBI Hostage Negotiator Kyle Vowinkel
Did you negotiate with terrorists this week? No, I’m not talking about a toddler who won’t eat his broccoli or a comedy club manager who “knows funny.” I mean…
Reasonably Happy with Paul OllingerCan a Conservative Win in NYC?
This week, I sat down with Caroline Shinkle, the Republican candidate for Congress in New York’s 12th District. Caroline studied economics at MIT and graduated…
Reasonably Happy with Paul OllingerJared Dillian on ‘The Awesome Portfolio’
My guest today is Jared Dillian, a former Wall Street trader, DJ, and the best-selling author of Street Freak, No Worries, and his new book, The Awesome…
Reasonably Happy with Paul OllingerDave Winfield, Baseball Legend
If MLB first-ballot Hall-of-Famer Dave Winfield’s story tells us anything, it’s that you can’t judge a person by how things appear on the surface. What we saw…
Reasonably Happy with Paul OllingerLife in the Soviet Union (w/ Vitaliy Katsenelson)
Vitaliy Katsenelson grew up in the Soviet Union - in Murmansk, the largest city north of the Arctic Circle. Today, he is the CEO & Chief Investment Officer of…
Reasonably Happy with Paul OllingerSenator Phil Gramm Dispels Economic Myths
This week, I sit down with Phil Gramm, economist, three-term United States Senator from Texas, former chairman of the Senate Banking Committee, and co-author…
Reasonably Happy with Paul Ollinger‘Young Money’ with Jack Raines
This week, I’m talking to Jack Raines, the guy behind the mega-popular Substack Young Money and author of a great new book called Young Money: A Field Guide to…
Reasonably Happy with Paul OllingerThe Secret Economics Behind Only Fans, Tarrifs, and Government Grocery Stores
What’s that you say – you want an interview with an economist who has both a great sense of humor and movie star good looks? Well look no further, friends…
Reasonably Happy with Paul OllingerCan 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…
Reasonably Happy with Paul OllingerFreeze 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…
Reasonably Happy with Paul OllingerNobel 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…
Reasonably Happy with Paul OllingerHow 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…
Reasonably Happy with Paul OllingerThe 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…
Reasonably Happy with Paul OllingerTRIGGERnometry'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…
Reasonably Happy with Paul OllingerW. 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…
Reasonably Happy with Paul Ollinger5 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…
Reasonably Happy with Paul Ollinger5 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…
Reasonably Happy with Paul OllingerA 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…
Reasonably Happy with Paul Ollinger5 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…
Reasonably Happy with Paul OllingerI Read My Essays to You
✍️ Follow Paul Ollinger on Substack by clicking here ✍️ Hello friends, this week's Reasonably Happy is me reading some of my favorite posts from my Substack…
Reasonably Happy with Paul Ollinger5 Questions with Dave Barry
✍️ Follow Paul Ollinger on Substack by clicking here ✍️ Oh my goodness what a fun time I had chatting with Dave Barry on the first episode of 5 Questions, my…
Reasonably Happy with Paul OllingerGretchen Rubin Will Teach You to be Happy
✍️ Follow Paul Ollinger on Substack by clicking here ✍️ “Happiness is a choice that requires effort at times.” -Aeschylus Whenever I go back and re-listen to…
Reasonably Happy with Paul OllingerMoney, Family & Comedy w/Roy Wood Jr.
✍️ Follow Paul Ollinger on Substack by clicking here ✍️ My guest today is Roy Wood, Jr. You know him from The Daily Show and from his acclaimed stand-up…
Reasonably Happy with Paul OllingerHow to Get Rich in America
✍️ Follow Paul Ollinger on Substack by clicking here ✍️ “Capitalism is rigged!” cry the masses. “Nobody gets ahead anymore,” says the mainstream press. And 60%…
Reasonably Happy with Paul OllingerThe Fragile Power of Wealth
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…
Reasonably Happy with Paul OllingerSurviving the Loss of a Child
“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…
Reasonably Happy with Paul OllingerMillionaires 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…
Reasonably Happy with Paul OllingerThe 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…
Reasonably Happy with Paul OllingerMoney, 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…
Reasonably Happy with Paul OllingerBelieve 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…
Reasonably Happy with Paul OllingerGina 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…
Reasonably Happy with Paul OllingerThe 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…
Reasonably Happy with Paul OllingerInsider 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…
Reasonably Happy with Paul OllingerSurviving 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…
Reasonably Happy with Paul OllingerMarriage, Infidelity, and Millennial Disillusionment with Erin Somers
Erin Somers' new novel, The Ten Year Affair is a story about Millennial disillusionment (and extramarital sex). The New Yorker called it “intoxicating” and W…
Reasonably Happy with Paul OllingerA.I. Facts, Fears and Fiction (w/ Bryan Reimer)
AI will have at least as big an effect on society as the invention of electricity. That’s the prediction of MIT’s Bryan Reimer. Bryan is the co-author of the…
Reasonably Happy with Paul OllingerFrom Apartheid to Atlanta w/ Robyn Curnow
My guest is Robyn Curnow, a native South African who spent over two decades at CNN, where she hosted CNN’s Newsroom, and anchored The International Desk with…
Reasonably Happy with Paul OllingerRewrite Mental Illness w/Laura Delano
Laura Delano is the author of Unshrunk: A Story of Psychiatric Treatment Resistance. Laura was fourteen years old when she saw her first psychiatrist, which…
Reasonably Happy with Paul OllingerFind your Essential Intent w/ Greg McKeown
Welcome back to this holiday conversation with ‘Essentialism' author Greg McKeown (see his very impressive resume below). As you set your goals and intentions…
Reasonably Happy with Paul OllingerHigh Net Worth Divorce with Laura Wasser
People magazine called Laura Wasser “the celebrity of celebrity divorce attorneys,” which makes sense considering she has—according to Wikipedia—handled cases…
Reasonably Happy with Paul OllingerSurviving the College Application Process w/ Jeffrey Selingo
As the father of two prep school students, I was very eager to meet this week’s guest. Jeffrey Selingo has written about college admissions for more than 25…
Reasonably Happy with Paul OllingerPaul’s Insights into NYC, Email, and Estate Planning
Hello friends. On this week’s episode, I read to you—like a daddy rocking his baby to sleep—the most recent posts from my Substack newsletter, which you can…
Reasonably Happy with Paul OllingerConfronting Mortality with Thad Reichley
Imagine being told you have a terminal illness. Would it change the way you approach each day? Two years ago, Thad Reichley went to the doctor because he had…
Reasonably Happy with Paul OllingerWalking Away from Fame and Money with Rachel Heck
Rachel Heck was a golf prodigy who qualified for the US Women’s Open at age 15 and made the cut. As a freshman in high school, she committed to play at…
Reasonably Happy with Paul OllingerFamily, Politics & The American Dream with Raj Goyle | Reasonably Happy
Raj Goyle is running for Comptroller of New York state, and he wants your support. He’s got mine because I think Raj is what America is all about. A…
Reasonably Happy with Paul OllingerStoic Street Smarts w/ Ed Latimore
Ed Latimore grew up in the projects of Pittsburgh where poverty, drugs, and gun violence were the rule of the streets. But he escaped and went on to become a…
Reasonably Happy with Paul OllingerSoul on Fire w/ John O’Leary (Encore episode)
John O’Leary’s life story has just been made into a movie called Soul On Fire, starring William H. Macy and John Corbett. When John was 9 years old, he played…
Reasonably Happy with Paul OllingerWhy You Will Never Feel Rich w/ Daniel Crosby
Acclaimed psychologist, behavioral finance expert, and author, Dr. Daniel Crosby, PhD* joins me this week to discuss his new book The Soul of Wealth: 50…
Reasonably Happy with Paul OllingerWhy Two Parents Are Better Than One w/ Melissa Kearney (Encore)
Melissa Kearney is the author of The Two-Parent Privilege: How Americans Stopped Getting Married and Started Falling Behind. Her book confronts the politically…
Reasonably Happy with Paul OllingerGiving Away Half-a-Billion Dollars w/ Craigslist founder, Craig Newmark
If you had hundreds of millions of dollars, how would you use it? Craigslist founder Craig Newmark faces this exact “problem”—and he’s working hard to give his…
Reasonably Happy with Paul OllingerLaughing at Death w/ John Kenney
What happens when you mix grief, comedy, and a brutally honest take on life’s hardest moments? You get John Kenney’s new book, I See You’ve Called in Dead. In…
Reasonably Happy with Paul OllingerRise of Populism w/ Brad Todd
Political strategist, author, and CNN commentator Brad Todd joins Paul Ollinger for a no-BS and eye-opening conversation about what’s really happening in…
Reasonably Happy with Paul OllingerFrom Prison to Oprah
What happens when a suburban soccer mom falls into heroin addiction, commits felonies, and ends up in prison—only to climb back out and become a four-time New…
Reasonably Happy with Paul OllingerVote for Jesus! w/ Jonathan Rauch
What happens when someone who grew up Jewish, gay, and atheist finds deep inspiration in the teachings of Jesus? In this fascinating conversation, Jonathan…
Reasonably Happy with Paul OllingerTribalism is Dumb (w/Andrew Heaton)
Andrew Heaton is the author of the new book Tribalism Is Dumb and the host of The Political Orphanage podcast. He sits down with Paul to unpack where tribalism…
Reasonably Happy with Paul OllingerPuck CEO, Sarah Personette
This week, Paul sits down with Sarah Personette, CEO of Puck, the fast-growing news outlet the New York Times described as “Vanity Fair for the Substack era.”…
Reasonably Happy with Paul OllingerWeapons Grade Gorgeous w/ Mehran Khaghani | Reasonably Happy with Paul Ollinger
Paul sits down with comedian and actor Mehran Khaghani and gets deep into the psyche of a man who was brought to America from Iran as a 3 year old who…
Reasonably Happy with Paul OllingerHow Victimhood and Narcissism Hold Us Back (w/ Scott Barry Kaufman)
Scott Barry Kaufman is a cognitive scientist and best-selling author of the book Rise Above: Overcome a Victim Mindset, Empower Yourself, and Realize Your Full…
Reasonably Happy with Paul OllingerLegacy, Loss, and Being Jewish Now | Reasonably Happy with Paul Ollinger
Zibby Owens is an author, publisher, and bookstore owner. She opens up about her writing journey, legacy, loss, and identity as the daughter of Blackstone…
Reasonably Happy with Paul OllingerJeffery Toobin on Presidential Power | Reasonably Happy Podcast
CNN legal analyst and bestselling author Jeffrey Toobin breaks down the hidden power of presidential pardons — and how they reveal the true character of…