Reasonably Happy with Paul Ollinger
by Paul Ollinger
Latest episode
The Collapse of Parenting (w/ Dr. Leonard Sax)
The Collapse of Parenting (w/ Dr. Leonard Sax)
About this podcast
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
Episodes
The newest 50 of 349 episodes
- The Collapse of Parenting (w/ Dr. Leonard Sax) · 1 h 3 minDr. Leonard Sax is an MD, PhD psychologist who has been practicing family medicine for over 35 years. He is worried about the disturbing trends he sees. According to Dr. Sax: *…
- $18 Billion, Epstein, and Russian Girlfriends: The Life of Leon Black · 1 h 1 minBill Cohan writes big, meaty books about the personalities and institutions that shape American finance. His latest, Money to Burn: The Unvarnished Truth About Leon Black…
- FBI Hostage Negotiator Kyle Vowinkel · 55 minDid 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 real terrorists…
- Can a Conservative Win in NYC? · 38 minThis 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 from Harvard Law…
- Jared Dillian on ‘The Awesome Portfolio’ · 45 minMy 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 Portfolio. Let me ask you…
- Dave Winfield, Baseball Legend · 51 minIf 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 from the outside: a…
- Life in the Soviet Union (w/ Vitaliy Katsenelson) · 58 minVitaliy 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 IMA (Investment…
- Senator Phil Gramm Dispels Economic Myths · 1 h 0 minThis 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 of 'The Triumph of…
- ‘Young Money’ with Jack Raines · 58 minThis 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 Wealth and Purpose…
- The Secret Economics Behind Only Fans, Tarrifs, and Government Grocery Stores · 57 minWhat’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. Matt Hill teaches…
- Can You Fake Happiness? w/Beth Cabrera · 44 min“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…
- Freeze the Rent! And Other Silly Policies ( w/ Paula Pant) · 1 h 12 minLast 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…
- Nobel Prize Winner on "Moral Economics" · 50 minThis 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…
- How Empathy Is Destroying Western Civilization (with Gad Saad) · 1 h 10 minIn 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…
- The Richest Family You've Never Heard Of · 52 minInvestment 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…
- TRIGGERnometry's Francis Foster on Teaching, Comedy, and Why the U.K. is Fucked · 31 minFrancis 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…
- W. Kamau Bell on Cosby, Comedy, and Father's Day · 28 minI 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…
- 5 Questions with Bruce Feiler · 37 minThanks 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…
- 5 Questions with Andy Borowitz · 31 minOn 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…
- A Political Family Black Sheep Tells All (with Rosebud Baker) · 50 minMy 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…
- 5 Questions with A.J. Jacobs · 32 min✍️ 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 Read My Essays to You · 36 min✍️ 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 over the past six…
- 5 Questions with Dave Barry · 31 min✍️ 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 bite-sized…
- Gretchen Rubin Will Teach You to be Happy · 59 min✍️ 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 one of my podcast…
- Money, Family & Comedy w/Roy Wood Jr. · 57 min✍️ 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 specials, where he proves…
- How to Get Rich in America · 1 h 6 min✍️ Follow Paul Ollinger on Substack by clicking here ✍️ “Capitalism is rigged!” cry the masses. “Nobody gets ahead anymore,” says the mainstream press. And 60% of young people…
- The Fragile Power of Wealth · 47 minIf 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…
- Surviving the Loss of a Child · 1 h 4 min“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…
- Millionaires v. Billionaires in NYC · 1 h 6 minChris 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…
- The Beatles, Ted Turner, and Ric Flair with Steve Chamberlain · 1 h 1 minThis 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…
- Money, Fame, and Misery: Meet the Beatles · 58 minMoney, 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…
- Believe and You Will See! (w/ Nir Eyal ) · 58 minMy 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…
- Gina Gershon on Fame, Desire, and Boobs · 1 h 0 minGuess 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…
- The Courage to Be Right w/ Matt Kaplan · 58 minMatt 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…
- Insider Trading w/Tom Hardin · 1 h 13 minHow 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…
- Surviving Middle Age w/ Ben Markovits · 48 minBen 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…
- Marriage, Infidelity, and Millennial Disillusionment with Erin Somers · 42 minErin Somers' new novel, The Ten Year Affair is a story about Millennial disillusionment (and extramarital sex). The New Yorker called it “intoxicating” and W praised the book for…
- A.I. Facts, Fears and Fiction (w/ Bryan Reimer) · 43 minAI 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 new book ‘How to…
- From Apartheid to Atlanta w/ Robyn Curnow · 60 minMy 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 Robyn Curnow. Prior…
- Rewrite Mental Illness w/Laura Delano · 1 h 11 minLaura Delano is the author of Unshrunk: A Story of Psychiatric Treatment Resistance. Laura was fourteen years old when she saw her first psychiatrist, which was not something…
- Find your Essential Intent w/ Greg McKeown · 1 h 25 minWelcome back to this holiday conversation with ‘Essentialism' author Greg McKeown (see his very impressive resume below). As you set your goals and intentions for 2026, Greg’s…
- High Net Worth Divorce with Laura Wasser · 40 minPeople magazine called Laura Wasser “the celebrity of celebrity divorce attorneys,” which makes sense considering she has—according to Wikipedia—handled cases for A+listers like…
- Surviving the College Application Process w/ Jeffrey Selingo · 55 minAs 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 years and is a New…
- Paul’s Insights into NYC, Email, and Estate Planning · 43 minHello 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 find here. (You can…
- Confronting Mortality with Thad Reichley · 1 h 4 minImagine 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 the flu. When…
- Walking Away from Fame and Money with Rachel Heck · 57 minRachel 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 Stanford University, where…
- Family, Politics & The American Dream with Raj Goyle | Reasonably Happy · 52 minRaj 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 first-generation…
- Stoic Street Smarts w/ Ed Latimore · 1 h 8 minEd 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 professional boxer…
- Soul on Fire w/ John O’Leary (Encore episode) · 52 minJohn 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 with fire and got…
- Why You Will Never Feel Rich w/ Daniel Crosby · 56 minAcclaimed psychologist, behavioral finance expert, and author, Dr. Daniel Crosby, PhD* joins me this week to discuss his new book The Soul of Wealth: 50 Reflections on Money and…
