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 OllingerPaul Reads His Thanksgiving Essays
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…
Reasonably Happy with Paul OllingerEd Begley Jr. on Finding Serenity in Hollywood
✍️ 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…
Reasonably Happy with Paul OllingerPushing Our Kids Too Hard: On Toxic Achievement Culture with Jennifer Wallace
✍️ Subscribe to Paul’s Substack ‘Money & the Meaning of Life’ here. ✍️ Jennifer Wallace is a journalist and author specializing in psychology, parenting, and…
Reasonably Happy with Paul OllingerLessons from an '80s Guitar god with Rik Emmett of Triumph
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…
Reasonably Happy with Paul OllingerThe NHL, Brain Injury, and Psilocybin with Daniel Carcillo
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…
Reasonably Happy with Paul OllingerPaul and Cal Fussman Talk Israel, Hamas
Over the past 30 years, Cal Fussman has interviewed a breathtaking array of the world’s most fascinating people, including Nelson Mandela, Clint Eastwood…
Reasonably Happy with Paul OllingerOn Losing Billions with Victor Haghani
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…
Reasonably Happy with Paul OllingerHow Fear Can be Your Friend with Farnoosh Torabi
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…
Reasonably Happy with Paul OllingerHow Much Should You Pay for College? with Ron Lieber (Encore)
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…
Reasonably Happy with Paul OllingerWhy 2 Parents Are Better Than One with Melissa Kearney
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…
Reasonably Happy with Paul OllingerThe Funniest Financial Speaker on Earth (besides Paul) with Garrett Gunderson
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…
Reasonably Happy with Paul OllingerBreak Free from Automated Spending Habits with Julio Vincent Gambuto
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…
Reasonably Happy with Paul OllingerSorority Rush Consultant Trisha Addicks (as seen on Bama Rush)
“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…
Reasonably Happy with Paul OllingerOpioids: Greed, Death, and $$$$ with Barry Meier (Encore)
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…
Reasonably Happy with Paul OllingerThe Secret to Being Very, Very Rich (and more)
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…
Reasonably Happy with Paul OllingerSelf Help for Mediocre People with Laura Belgray
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…
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 OllingerFinding Hidden Assets in Divorce Discovery with Nick Himonidis
If you’re trying to hide assets from your spouse or soon to be ex-spouse, beware! Whether it’s Cayman Islands bank accounts, bearer bonds stashed in a safe…
Reasonably Happy with Paul OllingerDivorce For Wealthy Women with Olivia Summerhill
Having experienced divorce as the child of a wealthy family, Olivia Summerhill understands the massive impact parents fighting about money can have on their…
Reasonably Happy with Paul OllingerI See Rich People (with Will Vogt)
Will Vogt is a photographer with a front row seat to the American upper class. Raised on Philadelphia’s Main Line, Will attended boarding school, and spent…
Reasonably Happy with Paul OllingerStudent Loan Debacle with Oren Cass
Our higher education system is broken. But instead of trying to fix the underlying issues, the Biden administration is attempting to treat the symptoms with a…
Reasonably Happy with Paul OllingerThe All-or-Nothing Marriage with Eli Finkel
If you find marriage to be hard, you are not alone. If you feel as if your spouse should fulfill every single physical, emotional, sexual, and financial need…
Reasonably Happy with Paul OllingerWall Street, Cocaine, and Recovery with Turney Duff
Turney Duff was making millions on Wall Street until cocaine addiction brought him to his knees. His book The Buy Side: A Wall Street Trader’s Tale of…
Reasonably Happy with Paul OllingerStaying Hungry in Your 50’s
For your summer listening while driving, walking, gardening, pleasure, Paul reads three of his latest pieces from Substack (Money and the Meaning of Life)…
Reasonably Happy with Paul OllingerSearching for Meaning at Work with Bruce Feiler
Bruce Feiler is a seven-time New York Times best-selling author of books such as Life is in the Transitions, Walking the Bible, and The Council of Dads…
Reasonably Happy with Paul OllingerFamily Fortune and Misfortune with Janny Scott (Encore)
Janny Scott is the descendant of railroad barons and financial tycoons. She grew up on an 800-acre estate on the Philadelphia Main Line. In her book The…
Reasonably Happy with Paul OllingerKevn Kinney is Done Auditioning
Kevn Kinney is the lead singer of Drivin N Cryin, a rock band that achieved legendary status in the Southeast during the late 80s and 90s but never quite broke…
Reasonably Happy with Paul OllingerStarting from the Bottom with Justin Richmond
Justin Richmond is the producer and co-host of Pushkin's music podcast Broken Record with writer Malcolm Gladwell and Def Jam co-founder Rick Rubin. He is also…
Reasonably Happy with Paul OllingerIs Private School Worth it?
Annual private school tuition can run over $60,000 in big cities like New York or Los Angeles. But even in smaller markets like Atlanta, 14 years of private…
Reasonably Happy with Paul OllingerUsing Your 4,000 Weeks with Oliver Burkeman (Encore)
Oliver Burkeman is the author of 4,000 Weeks: Time Managment for Mortals, which Adam Grant calls “The most important book ever written about time management.”…
Reasonably Happy with Paul OllingerCooking with Money w/ Frankie Celenza
Chef Frankie Celenza started his culinary career with an illicit George Foreman grill in his prep school dorm room. Today, Frankie is the Emmy award-winning…
Reasonably Happy with Paul OllingerWealthy Woman Flies Southwest with Leah Rudick
Leah Rudick is an actor, writer, and comedian whose Wealthy Woman character videos have earned her almost one million followers on Instagram and TikTok. Thanks…
Reasonably Happy with Paul OllingerMorgan Housel on The Psychology of Money (Encore)
Morgan Housel is the author of the book, The Psychology of Money: Timeless Lessons on Wealth, Greed, and Happiness. As the back cover of his new best-seller…
Reasonably Happy with Paul OllingerCars, Sex, and Money with Robert Searle
Do women find men in expensive cars more attractive than men in less expensive cars? Some people believe that the answer to this question is so patently…
Reasonably Happy with Paul OllingerWhy it’s Called “F-You Money” and other Thoughts on Wealth and Happiness
This week, Paul reads some of the recent essays from his Substack. In "Why Talking About Money and Happiness Matters” he reflects on the reasons Bono, Jonah…
Reasonably Happy with Paul OllingerCancer, Careers, Finances, and Family with Julie Saxon (Encore episode)
Julie Saxon is the mother of two and a senior media executive. In 2013, her life was upended when her husband, Joel, was diagnosed with stage IV colorectal…
Reasonably Happy with Paul OllingerMass Hole Donuts co-founder Peter Gladstone
This episode is about working for fun, love, and legacy. Peter Gladstone is the Co-founder of Mass Hole Donuts, bakers of gourmet donut holes that celebrate…
Reasonably Happy with Paul OllingerRich B*tch Nicole Lapin: More than Meets the Eye
Nicole Lapin is the New York Times best-selling author of Rich B***h, Boss B***h, Miss Independent, and Becoming Super Woman. A summa cum laude graduate of…
Reasonably Happy with Paul OllingerA Hollywood Dream Career with Larry Thompson
Larry Thompson is an entertainment manger in Beverly Hills, CA. In his 50+ years in Hollywood, Larry has guided the careers of over 200 stars, including Drew…
Reasonably Happy with Paul OllingerNew Fame, New Money with Katherine Blanford
A year ago, Katherine Blanford was working as a nanny by day and doing comedy at night. Last summer, she made her network television debut on The Tonight Show…
Reasonably Happy with Paul OllingerCrazy Money's direction in 2023
Hey everybody. Happy 2023! This is a short, lightly edited greeting from Paul /me about where the podcast has been in 2022 and where we're going to take it in…
Reasonably Happy with Paul OllingerHow Your Mindset Can Change Your World with David Robson
The philosophical martial artist and actor, Bruce Lee is supposed to have said, “So you think, so shall you become.” On this week’s episode, we explore the…
Reasonably Happy with Paul OllingerGrowing Up Rich with Kristin Keffeler
Kristin Keffeler is the author of a new book called The Myth of the Silver Spoon: navigating family wealth and creating an impactful life. Kristin is also the…
Reasonably Happy with Paul OllingerWhy Boys and Men are Struggling with Richard Reeves
Richard Reeves is a senior fellow at the Brookings Institution and the author of a new book called Of Boys and Men: Why the Modern Male Is Struggling, Why It…
Reasonably Happy with Paul OllingerThe Need to Belong with Geoffrey L. Cohen
We don't think about it all the time, but BELONGINGNESS is the third most fundamental desire on Maslow’s Hierarchy of Needs. Just above safety and…
Reasonably Happy with Paul OllingerThe Hedge Fund Legend Hugh Hendry
Former hedge fund manager Hugh Hendry grew up working class in Glasgow, Scotland. His anxiety, detachment from money, and passionate observations of life led…
Reasonably Happy with Paul OllingerMoney and Opioids with Barry Meier
Barry Meier is a former investigative reporter at The New York Times and the author of the book, Pain Killer: An Empire of Deceit and the Origin of America's…
Reasonably Happy with Paul OllingerWhy Status Matters with Will Storr
Where do you sit on the social hierarchy? You might not think about it daily, but if I asked you to compare your status to that of one of your friends, you'd…
Reasonably Happy with Paul OllingerMoney in College Sports, Part 2 (with AJ Vaynerchuk and Laine Higgins)
This episode is Part Two of our Money in College Sports: NIL series. Until last year, college athletes were prohibited from collecting any compensation. But…
Reasonably Happy with Paul OllingerEmotions and Money Stress with Ken Honda
The news from the economic world is pretty bad right now. Inflation up and the stock market’s down, which means we're all experiencing some degree of financial…
Reasonably Happy with Paul OllingerRobinhood, Wall Street Bets, and the GameStop Stock Frenzy with Spencer Jakab
Spencer Jakab is the editor of The Wall Street Journal's Heard on the Street column and the author of a fascinating new book called The Revolution That Wasn't…
Reasonably Happy with Paul OllingerMoney in College Sports, Part 1 with Darren Rovell and John Staton
Up until last year, no college athlete could legally, officially accept compensation for playing a sport at his or her college. That changed last year with a…
Reasonably Happy with Paul OllingerMoney and Pro Golf: How LIV Golf’s Billions Threaten the PGA with Rich Beem
Saudi-backed LIV Golf is throwing hundreds of millions of dollars at top pro golfers in an attempt to lure them away from the PGA Tour. The Tour is responding…
Reasonably Happy with Paul OllingerPorn, Money, and Women in Hollywood with Maitland Ward
Maitland Ward is an adult film star and author of a new book called Rated X: How Porn Liberated Me from Hollywood. Best known for her role as Rachel Maguire on…
Reasonably Happy with Paul OllingerDrug Cartels, Money Laundering, and HSBC with Chris Blackhurst and Everett Stern
I've got a great conversation to share with you today about international banking, massive drug cartels and billions and laundered money. My first guest is…
Reasonably Happy with Paul OllingerThe Prison Break of a Global CEO - The story of Carlos Ghosn
Carlos Ghosn is the former CEO of both Renault and Nissan. Japanese authorities arrested him for (allegedly) paying himself tens-of-millions in unreported…
Reasonably Happy with Paul OllingerStudent Loan Debt with Oren Cass
Why in the world is student debt treated differently than all other kinds of debt? Why does the cost of college keep sky-rocketing? Why do colleges and…
Reasonably Happy with Paul OllingerSurviving the Market Meltdown with Ben Carlson
Ben Carlson is the Director of Institutional Asset Management at Ritholtz Wealth Management and the author of several books about investing. He is the founder…
Reasonably Happy with Paul OllingerUniversal Basic Income with Andrew Yang
Andrew Yang is a former Presidential candidate and the founder of Venture for America. He's also the founder of the Forward Party where he advocates for…
Reasonably Happy with Paul OllingerRacial Wealth Gap with Coleman Hughes
Today’s guest is Coleman Hughes, he's a writer, podcaster and opinion columnist who specializes in issues related to Race, Public Policy and Applied Ethics. He…