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. words.paulollinger.com
Author
Paul Ollinger
Category
Podcast website
Latest episode
Jul 8, 2026
Where to listen?
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Episodes
Paul Reads Money Essays 21.02.2024 39:21
In this special “where has Paul been?” episode, Paul reads three of his latest pieces from his Substack, Money and the Meaning of Life, so that you can drive or workout without reading. Latest posts include: Adventures in Affluence: Dry Cleaning - why Paul got freaked out when he starting thinking about how much he spends on dry cleaning every year. Gary v. Jerry: Why Gary Gulman Resents Rich Peop...
Race and Money with Coleman Hughes (Encore) 06.02.2024 41:34
Today’s guest is Coleman Hughes, a writer, podcaster, opinion columnist and self-described "Black man who does’t think everything is about race.” Coleman has a new book out this week called 'The End of Race Politics: Arguments for a Colorblind America,’ in which he confronts the "failed corporate diversity and inclusion efforts and poisonous race-based policies that hurt the very people they inten...
The Joys and Anxieties of Wealth (Encore) 28.12.2023 51:58
Paul Schervish studies very wealthy people: what worries them, what delights them, and what motivates them to give to charity. The Director of Boston College’s Center on Wealth and Philanthropy, Paul is the co-author of 'The Joys and Dilemmas of Wealth,' a 2010 report that is one of the most insightful studies of the ultra-affluent ever. We discuss how the fears and joys that come with being rich...
Dr. Drew Pinsky on Careers, Money, and Fame (Encore) 27.12.2023 1:09:26
This is a special holiday encore of the 2nd episode of Crazy Money with Dr. Drew, which ran Jan 30, 2019. Dr. Drew offers candid insight into the ups and downs of a career in broadcasting and medicine. From Loveline to Celebrity Rehab, Dr. Drew has been a staple on radio and cable television for over 30 years, but that doesn’t mean he’s rich — he’s got triplets to get through graduate school, afte...
How to Live a Stress-free Financial Life with Jared Dillian 19.12.2023 1:00:00
Financial gurus like Dave Ramsey or Suze Orman tell their audience that the key to achieving wealth—or just financial stability—is to cut back on the little things like that daily Starbucks latte. Jared Dillian thinks they’re wrong. Focusing on the little things, Jared argues, is pointless and unsustainable. But focusing on the big things, like your house, your car, and how much you pay for colleg...
Judd Apatow on Money, Fame, and Adam Sandler (Encore) 13.12.2023 48:26
Judd Apatow is one of the most important figures in comedy and film today. But he just doesn’t care that much about money. This non-attachment to material goods leaves him more time to focus on what matters: writing, directing, developing talent, and getting his family together for dinner. Judd has accomplished so much in his career that, in retrospect, his success appears to have been pre-ordaine...
Author Gary Sernovitz 05.12.2023 59:08
Gary Sernovitz is one of the funniest financial writers working today. His hilarious new novel The Counting House tells the story of a university’s Chief Investment Officer who is suffering a mid-life crisis. If you possess either an interest in finance or a robust / dark sense of humor, The Counting House will make you laugh and, at times, cry in empathy with the protagonist. Gary has spent the l...
How to Get Un-stuck with Merrick Furst, Ph.D. 29.11.2023 1:06:24
Do you ever feel stuck in life? As if you are in the wrong place or you’re in the right place but doing the wrong thing? What do you do when you find yourself at a crossroad? Today, I speak to innovation expert Merrick Furst about how seeing ourselves and the world more clearly can tell us how to move forward when the way isn’t clear. Merrick is a Distinguished Professor at Georgia Tech. His list...
Paul Reads His Thanksgiving Essays 21.11.2023 35:41
In this special “over the river and through the woods” episode, Paul reads four of his latest pieces from his Substack, Money and the Meaning of Life, so that you can drive or workout without reading. Latest posts include: Every Day Is Thanksgiving This One Question Will Help You Stop Comparing Yourself to Others Why the Jews? The holy roots of anti-semitism might surprise you This is Us: Inconclu...
Ed Begley Jr. on Finding Serenity in Hollywood 15.11.2023 38:45
✍️ Subscribe to Paul’s Substack ‘Money & the Meaning of Life’ here. ✍️ 🎤 See Paul’s upcoming comedy dates here and random thoughts on Instagram here. 🎤 Ed Begley Jr. has been acting professionally since 1967 when he appeared in an episode of My Three Sons. 56 years later, Ed has acted in hundreds of movies and TV shows, including An Officer and a Gentleman, Batman Forever, The Larry Sanders Show...
Pushing Our Kids Too Hard: On Toxic Achievement Culture with Jennifer Wallace 08.11.2023 49:29
✍️ Subscribe to Paul’s Substack ‘Money & the Meaning of Life’ here. ✍️ Jennifer Wallace is a journalist and author specializing in psychology, parenting, and health. Her new book 'Never Enough: When Achievement Culture Becomes Toxic—And What We Can Do About It' delves into our modern dilemma of busyness, achievement, credentialing, and status-seeking. Katie Couric calls the New York Times best-sel...
Lessons from an '80s Guitar god with Rik Emmett of Triumph 31.10.2023 1:05:15
Rik Emmett is a vocalist, guitarist and former member of the rock band Triumph, which earned 18 gold and nine platinum records in Canada and the United States in the late 1970s and early’80s. Triumph was known for its BIG live shows featuring lights, pyrotechnics, and lots of spandex (as was appropriate for the era!). Along with Rik's bandmates Gil Moore and Mike Levine, the power trio played loud...
The NHL, Brain Injury, and Psilocybin with Daniel Carcillo 24.10.2023 50:17
When Daniel Carcillo played in the NHL, he was known as an enforcer so tough and volatile that he earned the nickname “Car Bomb.” In his 12 seasons in the NHL, Daniel was a member of two Stanley Cup-winning teams (2013 and 2015 Chicago Blackhawks), led the league in penalty minutes, and was fined or suspended by the NHL 12 times. He also suffered about a dozen concussions and was diagnosed with ea...
Paul and Cal Fussman Talk Israel, Hamas 17.10.2023 1:09:35
Over the past 30 years, Cal Fussman has interviewed a breathtaking array of the world’s most fascinating people, including Nelson Mandela, Clint Eastwood, Barbara Walters, Richard Branson, Muhammed Ali, Mikhail Gorbachev, Neil Young, Serena Williams, Tim Ferriss, Kobe Bryant, Al Pacino, Pelé, and hundreds more. He co-authored Larry King’s memoir and won a James Beard Award for a story about his jo...
On Losing Billions with Victor Haghani 10.10.2023 1:01:04
Victor Haghani is the author of a new book called The Missing Billionaires: A Guide to Making Better Financial Decisions, which explores why family fortunes like the Vanderbilts' get destroyed in the hands of the heirs. Victor knows a lot about wild swings in wealth. As co-founding partner of the Long-Term Capital Management (LTCM), Victor saw the hedge fund's value soar over the first years of it...
How Fear Can be Your Friend with Farnoosh Torabi 03.10.2023 59:21
Farnoosh Torabi is an Iranian American journalist and one of the country’s most trusted personal finance experts. In her new book, A Healthy State of Panic she examines the role fear can have in leading us toward the relationships, careers, and financial situations we are meant to have. For over two decades, Farnoosh has a strived to help people become financially empowered and lead richer lives....
How Much Should You Pay for College? with Ron Lieber (Encore) 26.09.2023 48:19
After 15 years of financial reporting, Ron Lieber reports that “No consumer decision inspires more confusion and emotion than the question of what to pay for college,” which is understandable since four years at many state schools now costs over $100k in tuition and four years of private school can run over $300k! The "Your Money" columnist for the New York Times, Ron is the author ofThe Price Yo...
Why 2 Parents Are Better Than One with Melissa Kearney 19.09.2023 40:55
Kids who grow up in stable, two-parent homes are less likely to live in poverty, have behavioral problems, and get in trouble at school. They’re more likely to go to college, attain stable employment, achieve higher earnings, and to get married themselves. So reports Melissa Kearney in her new book The Two-Parent Privilege: How Americans Stopped Getting Married and Started Falling Behind. A profes...
The Funniest Financial Speaker on Earth (besides Paul) with Garrett Gunderson 13.09.2023 55:31
Garrett Gunderson is a NYT best selling author and the funniest financial speaker you may or may not have heard of. The son of a Utah coal-miners, Garrett wants to teach others how to become financially independent and have a laugh along the way. He has written several money books, including Disrupting Sacred Cows, Killing Sacred Cows, and What Would Billionaires Do? among others. His new book Mon...
Break Free from Automated Spending Habits with Julio Vincent Gambuto 06.09.2023 1:07:34
In an automated world without constraints or time to think, our spending has been super-charged. Markets, apps, and e-commerce are all designed to separate us from our money as quickly and consistently as possible. So argues Julio Vincent Gambuto in his new book, Please Unsubscribe, Thanks!: How to Take Back Our Time, Attention, and Purpose in a World Designed to Bury Us in Bullshit. Paul and Juli...
Sorority Rush Consultant Trisha Addicks (as seen on Bama Rush) 29.08.2023 41:37
“Parents Hire $4,000 Sorority Consultants to Help Daughters Dress and Impress During Rush” read the Wall Street Journal headline that nearly made my neck snap. As a middle-aged man whose kids aren’t quite college age, I was unaware of the #RushTok phenomenon on TikTok or the Bama Rush documentary that sparked a massive fascination with the sorority rush process at the University of Alabama. Trisha...
Opioids: Greed, Death, and $$$$ with Barry Meier (Encore) 22.08.2023 42:39
The new Netflix series Painkiller is based on a book my guest, Barry Meier wrote over 20 years ago. In Pain Killer: An Empire of Deceit and the Origin of America's Opioid Epidemic, Meier explores how Purdue Pharma’s drug OxyContin catalyzed a plague of addiction and death that has destroyed families and whole communities across the country. Between 1999 and 2020, 564,000 Americans died from an opi...
The Secret to Being Very, Very Rich (and more) 15.08.2023 23:47
Paul reads three of his latest pieces from his Substack, Money and the Meaning of Life, including: Dare to Suck: What you can learn about improvement from acting coach Lesly Kahn and author Mark Manson The Secret to Being Very, Very Rich Nobody Needs a House with 8 Toilets 🔥Paul publishes these essays (about) every other Tuesday. You should subscribe here. 🔥 🚀 Follow Paul on Instagram here. 🚀...
Self Help for Mediocre People with Laura Belgray 09.08.2023 57:32
If your new college grad son or daughter is unemployed, sleeping in their childhood bedroom, and watching All My Children every day, fear not - Laura Belgray has been there and she turned out okay. As Laura explains in her new, laugh-out-loud (LOL) funny memoir, Tough Titties: On Living Your Best Life When You’re the F-ing Worst, sometimes it’s good to be unoccupied so that, when opportunity final...
High Net Worth Divorce with Laura Wasser 01.08.2023 37:14
People 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 Angelina Jolie, Kim Kardashian, Johnny Depp, Ryan Reynolds, Dr. Dre, Kevin Costner, Maria Shriver, and Jimmy Iovine, among many others. And while “celebrity divorce attorney” might conjure up images of a rapacious shark in...
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