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 OllingerBuy this, not that! with Author Sam Dogen
Sam Dogen left his job in investment banking at age 34 to start his financial newsletter, Financial Samurai. He's got a new book out this week called “Buy…
Reasonably Happy with Paul OllingerSoul in the Game with Vitaliy Katsenelson
Today’s guest is Vitaliy Katsenelson. He's an investor, writer and author of the new book ‘Soul in the Game : The Art of a Meaningful Life’. Nassim Nicholas…
Reasonably Happy with Paul OllingerLife after the PGA Championship with Rich Beem - ENCORE EPISODE
This is an encore episode with Rich Beem, winner of the 2002 PGA Championship, one of professional golf’s four major tournaments. Despite having won twice on…
Reasonably Happy with Paul OllingerThe Problem with Choice with Barry Schwartz - ENCORE EPISODE
This is an encore epsiode with Professor Barry Schwartz, author of several books, including Why We Work and The Paradox of Choice. I spoke to Barry in August…
Reasonably Happy with Paul OllingerHedge Fund Novelist with Jay Newman - Ep 145
Jay Newman makes BIG bets. In his 40 year hedge fund career, Jay was the guy who fought to recover deca-billion dollar debt defaults by countries like the…
Reasonably Happy with Paul OllingerThe Puzzle of Life (with A.J. Jacobs) - Ep 144
A.J. Jacobs believes that puzzles can save the world. The famously obscure 4-time New York Times best-selling author of books like The Know-It-All, Thanks a…
Reasonably Happy with Paul OllingerMoney and Comedy with Christian Finnegan - Ep 143
Description: Christian Finnegan is a comedian and actor, well known for his work on Chappelle’s Show and the popular sitcom, Are We There Yet? He has performed…
Reasonably Happy with Paul OllingerThe Joys and Anxieties of Wealth with Paul Schervish - Ep 142
Description: Paul Schervish studies very wealthy people: what worries them, what delights them, and what motivates them to give to charity. The Director of…
Reasonably Happy with Paul OllingerMid-Life Career Re-invention with Chip Conley - Ep 141
Something happens to many of us in our 40’s or 50’s: having achieved a certain level of success, we yearn to find work that is an expression of who we are…
Reasonably Happy with Paul OllingerFixing Financial Chaos with Joe Saul-Sehy - Ep 140
41% of people who make over $200k per year still cry about money. That’s the finding of a recent study that Paul discusses this week with Joe Saul-Sehy…
Reasonably Happy with Paul OllingerWhat’s Your Problem? with Jacob Goldstein - Ep 139
Jacob Goldstein is the author of Money: The True Story of a Made Up Thing and former co-host of Planet Moneywhere he worked for over a decade. His new podcast…
Reasonably Happy with Paul OllingerComparison and the Ultimate Money Delusion - Ep 138
If you think Paul Ollinger can’t draw poignant and funny lessons about money from the 1996 box office smash, Jerry Maguire, you are sadly mistaken. On this…
Reasonably Happy with Paul OllingerWhy Things Are Better than You Think with Grant J. Ryan - Ep 137
Many people want you to believe that the world is in worse shape than ever. They assert that wages are stagnant, inequality is growing and the earth is heating…
Reasonably Happy with Paul OllingerFounder of Russian Hedge Fund on Defying Putin with Bill Browder - ENCORE EPISODE
Bill Browder is the author of Red Notice: A True Story of High Finance, Murder, and one Man’s Fight for Justice, which is the best book I’ve read in a decade…
Reasonably Happy with Paul OllingerLL COOL J - ENCORE EPISODE
Nobody works harder than LL COOL J. The musician, producer, actor, and entrepreneur has been playing at the highest levels of art, business, and culture since…
Reasonably Happy with Paul OllingerJudd Apatow on Fame, Money, and the Creative Process - Ep 136
Judd Apatow doesn’t care that much about money. This non-attachment to material goods leaves him more time to focus on what matters: writing, developing…
Reasonably Happy with Paul OllingerOlympic Economics with Apolo Ohno - ENCORE EPISODE
In this episode, Apolo Ohno and I go deep into the economic realities of becoming an Olympian. Due to the steep cost of coaching, training, equipment, and…
Reasonably Happy with Paul OllingerHouse of Gucci author, Sara Gay Forden - Ep 135
Sara Gay Forden is the author ofHouse of Gucci: A Sensational Story of Murder, Madness, Glamour, and Greed,on which director Ridley Scott based his…
Reasonably Happy with Paul OllingerRaising Successful Kids with Julie Lythcott-Haims - Ep 134
Julie Lythcott-Haims is passionate about raising self-sufficient kids and helping them find their unique path into adulthood. The former Dean of Freshman at…
Reasonably Happy with Paul OllingerZen Money with Ken Honda - Ep 133
When it comes to money, there are two approaches: love or fear.” That’s what Ken Honda writes in his latest work, Happy Money: The Japanese Art of Making Peace…
Reasonably Happy with Paul OllingerOver-thinking and What to do About It with Jon Acuff - Ep 132
Overthinking is so deeply ingrained in humanity that it shows up as a theme in Buddhism, Stoicism, Shakespeare, and the songs of Barenaked Ladies. Jon Acuff…
Reasonably Happy with Paul OllingerFrom the Trailer Park to the Comedy Big Time with Rocky Dale Davis - Ep 131
Comedian Rocky Dale Davis grew in a trailer park in Brookwood, Alabama. His single mom worked hard to keep him fed and on the straight-and-narrow. After eight…
Reasonably Happy with Paul OllingerLife After Public Failure with Warwick Fairfax - Ep 130
Today we are going to talk about public mistakes: big, flagrant, public mistakes that might best be described as “failure” and earn the derision of the press…
Reasonably Happy with Paul Ollinger$50 Million Mistakes with Ali Partovi - Ep 129
Ali Partovi is an Iranian-Americanentrepreneur and angel investor. He is best known as a co-founder of Code .org, iLike, and LinkExchange. He was an early…
Reasonably Happy with Paul OllingerWhat HBO's Succession Tells us about Wealth with James A. Miller, Meredith Blake and David Lenok - Ep 128
Today we will be discussing the enthralling HBO series, Succession and all it tells us about wealth, dysfunctional family dynasties, ambition, and greed with…
Reasonably Happy with Paul OllingerThanksgiving Essays - Ep 127
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Reasonably Happy with Paul OllingerInvesting for Good with Judith Rodin, Joan Salwen, and Pieter van der Gaag - Ep 126
This week I speak to three distinguished guests about how money can be used to make the world a better place and how investors large and small can influence…
Reasonably Happy with Paul OllingerThat Voice in Your Head with Ethan Kross - Ep 125
That voice in your head isn’t all bad. Sure, it sometimes tells you you’re not good enough or that Bob from Accounting is plotting to get you fired, but your…
Reasonably Happy with Paul OllingerPreppy Handbook Author, Lisa Birnbach - ENCORE EPISODE
Lisa Birnbach is the author of over 20 books, includingThe Official Preppy Handbook, which became a cultural phenomenon in the early 1980’s. The book sold more…
Reasonably Happy with Paul OllingerBuckhead v. Atlanta - Ep 124
What would happen if the richest neighborhood in your town declared itself its own municipality, taking with it the tax dollars of the richest 20% of citizens?…
Reasonably Happy with Paul OllingerYour Brain on Money with Daniel Crosby - Ep 123
Educated at Brigham Young and Emory Universities, Dr. Daniel Crosby is a psychologist and behavioral finance expert who studies and writes about the…
Reasonably Happy with Paul OllingerFrom Iraq to Dancing with the Stars with J.R. Martinez - Ep 122
J.R. Martinez joined the Army to give back to the country that accepted his immigrant, single mother and to earn money for college. As a 19-year-old, handsome…
Reasonably Happy with Paul OllingerStevie Van Zandt takes it all in - Ep 121
Stevie Van Zandt is best-known as guitarist and founding member of Bruce Springsteen's E Street Band, and for playing Silvio Dante on HBO's The Sopranos and…
Reasonably Happy with Paul OllingerNet fulfillment v. Net worth with Bill Perkins - ENCORE EPISODE
(originally posted Sept, 2020) Would you consider yourself a success if you died with $1 million? How about $10 million? Well, what if you died with $0.00? In…
Reasonably Happy with Paul OllingerGianni Le Nguyen: mom, entrepreneur, Vietnamese refugee. ENCORE EPISODE
(Originally posted June, 2019) Gianni Le Nguyen fled Vietnam at the age of 5. Late one night in the early 1980s, her father wrapped his two young daughters in…
Reasonably Happy with Paul OllingerLuck v. Hard Work with Robert H. Frank- Ep 120
Robert H. “Bob” Frank teaches economics at Cornell and is the author of a dozen books, including the one that caught my eye for this week’s topic: Luck and…
Reasonably Happy with Paul OllingerAre Smart People Less Happy? with Raj Raghunathan- Ep 119
Is there something about being successful that makes you less happy? Do smart people’s over-active brains fill their heads with negative thoughts? If so, how…
Reasonably Happy with Paul OllingerHow to Restore Sanity to our Political System with Charlie Wheelan - Ep 118
Charlie Wheelan is a professor of economics and public policy at Dartmouth College and the author of several books, including Naked Money, Naked Economics, (no…
Reasonably Happy with Paul OllingerAndrew Sullivan Holds Nothing Back - Ep 117
Andrew Sullivan’s new book, Out on a Limb: Selected Writing 1989-2021 captures the best of his three decade quest to identify and share The Truth with his…
Reasonably Happy with Paul OllingerHow to Use Your 4,000 Weeks with Oliver Burkeman - Ep 116
Oliver Burkeman is the author of the new book, 4,000 Weeks: Time Managment for Mortals, which Adam Grant calls “The most important book ever written about time…
Reasonably Happy with Paul OllingerA conversation with my producer Mike Carano- Ep 115
Hello! My name is Mike Carano, I edit Crazy Money. At my suggestion I interviewed Paul for this weeks episode, and unexpectedly didn't get to a single question…
Reasonably Happy with Paul OllingerGod Wants You to be Rich with Rabbi Daniel Lapin - ENCORE EPISODE
(Originally posted May, 2020...but so worth another listen) Rabbi Daniel Lapin believes that money is the reward we get when we serve another one of God’s…
Reasonably Happy with Paul OllingerOvercoming Injury and Life After the NFL with Mohamed Massaquoi - Ep 114
Life has thrown a lot more than passes at former NFL wide receiver, Mohamed Massaquoi. Born in the United States to parents from Liberia, Mohamed grew up in…
Reasonably Happy with Paul OllingerWhy Commitment Matters with Pete Davis - Ep 113
Pete Davis is the author of Dedicated: The Case for Commitment in an Age Of Infinite Browsing. His Harvard Law School graduation speech, which served as the…
Reasonably Happy with Paul OllingerDoes More $ = More Happy? with Sir Angus Deaton - ENCORE EPISODE
(Originally posted September, 2019...but so worth another listen) Princeton economist and Nobel laureate, Sir Angus Deaton co-authored a famous study…
Reasonably Happy with Paul OllingerHow to Change with Katy Milkman - Ep 112
Katy Milkman is the James G. Dinan Professor at The Wharton School of the University of Pennsylvania, host of Charles Schwab’s popular behavioral economics…
Reasonably Happy with Paul OllingerLiving Rich v. Dying Rich with Joe Duran of Goldman Sachs - Ep 111
Joe Duran grew up poor, in a one-room house in Rhodesia (now Zimbabwe) during violent and tumultuous times. Today, Joe is Head of Goldman Sachs Personal…
Reasonably Happy with Paul OllingerAging Well with Dr. Laura Carstensen - Ep 110
Human life expectancy increased more in the 20th Century than it did in all prior years of human existence combined! This has meaningful impact on how we…
Reasonably Happy with Paul OllingerHey everyone, this is just a quick update from Paul to talk about how summer travel will affect the production schedule for Crazy Money.
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Reasonably Happy with Paul OllingerWealth and Existential Despair with Melissa Bernstein - Ep 109
Melissa Bernstein has great wealth, a wonderful husband, and six healthy children. She has also endured a lifetime of “existential anxiety and depression,”…
Reasonably Happy with Paul OllingerMoby on Fame, Fortune, Addiction, Animals - Ep 108
Moby’s first job as a DJ was spinning records at a dive bar next to a methadone clinic. A few years later, he was rich and famous, but "never felt more…
Reasonably Happy with Paul OllingerLife After Paralysis with Maura McVann Coley - Ep 107
In 1988, Maura McVann Coley sustained a traumatic spinal cord injury that deprived her of the ability to walk. Just 17 at the time of the accident, the then…
Reasonably Happy with Paul OllingerRebounding from Mid-life Melancholy with Jonathan Rauch - ENCORE EPISODE
(Originally posted Jan, 2020...but so worth another listen) In The Happiness Curve: Why Life Gets Better After 50, Jonathan Rauch explores the decline in…
Reasonably Happy with Paul OllingerHow business education builds character with Matt Slaughter - Ep 106
Matthew J. Slaughter is the Dean of the Tuck School of Business at Dartmouth where Paul (the host of this show) earned his MBA. In today’s conversation, Matt…
Reasonably Happy with Paul OllingerThe Science of Well-being with Dr. Laurie Santos - ENCORE EPISODE
(Originally posted Sept, 2019...but so worth another listen) Our brains are not good at predicting what will actually make us happy. You think you want more…
Reasonably Happy with Paul OllingerOur possessions, ourselves with Michael Heller & James Salzman - Ep 105
What does it mean to “own” something? Do you “own”your body? Do you own the dirt in your backyard? If someone flies a drone over your deck, do you have the…
Reasonably Happy with Paul OllingerWall Street, the movie: a panel discussion - Ep 104
This week we tried out a new format—a panel discussion about the 1987 classic Oliver Stone film, Wall Street. It starred Charlie Sheen, Michael Douglas, Darryl…
Reasonably Happy with Paul OllingerWall Street Trader Turns Big Time Writer with Jared Dillian - Ep 103
A working class kid from the poor part of Connecticut, Jared Dillian somehow managed in 2001 to land a job as a trader at Lehman Brothers, the then-prestigious…
Reasonably Happy with Paul OllingerMoney and the Maasai people with Josphat Mako - Ep 102
My guest today paid a dowry of eight cows for his first wife and six cows and three sheep for his second wife. Josphat Mako, or just “Mako," grew up in Kenya’s…
Reasonably Happy with Paul OllingerRyan Holiday on Stillness - ENCORE EPISODE
(Originally posted October, 2019) Ryan Holiday is the author of ten books, which have sold sold more than 2 million copies worldwide and been translated into…