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PODCAST

Reasonably Happy with Paul Ollinger

Comedian Paul Ollinger wants you to be happy but let’s not go crazy here, okay? In his new show, Reasonably Happy: the Skeptic’s Guide to Achievable Contentment (fka Crazy Money), Paul will help you find authentic fulfillment through candid conversations with comedians, authors, celebrities, and other remarkable guests who share their failures and foibles, anxiety and addiction, and their grand vision of life that keeps them pushing forward.

business philosophy

All Episodes

58:08

Wall Street, the movie: a panel discussion - Ep 104

Reasonably Happy with Paul Ollinger ·

2021/04/06

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 Hannah and a whole bunch of other amazing actors. The movie, which was a morality tale about financial excess, both celebrated and condemned the era's obsession with money and over-the-top luxury (clearly that’s over!). In addition to cocaine, caviar, and steak tartare, it asked us to consider: How much is enough? How do you define

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51:00

Wall Street Trader Turns Big Time Writer with Jared...

Reasonably Happy with Paul Ollinger ·

2021/03/30

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 investment bank. Wearing cheap suits from the Mens Wearhouse, he found himself out-of-place among the Armani-clad Ivy League set on Wall Street. But he loved trading and made a lot of money in the process. In this candid conversation, Jared shares frank insights into the incredible stress of trading and the mental health that became apparent

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50:09

Money and the Maasai people with Josphat Mako - Ep 102

Reasonably Happy with Paul Ollinger ·

2021/03/23

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 Maasai Mara, a massive plain just north of the Serengeti. He taught himself English, learned how to drive, and has since become become a well-known safari guide for the legendary Cottars camps. In today’s episode, we talk about his childhood, daily life in the Maasai Village, who goes to school in their culture (it will surprise you!), and

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60:12

Ryan Holiday on Stillness - ENCORE EPISODE

Reasonably Happy with Paul Ollinger ·

2021/03/16

(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 30 languages. World-class athletes, celebrities and political leaders use his lessons to achieve peak performance. His 2014 book, The Obstacle Is The Way, was read by the New England Patriots during their 2014 Super Bowl-winning season and by four-time major champion golfer Rory McIlroy as preparation for the 2019 Masters Tournament. In this

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64:55

Andy Stanley on Jesus and Money - Ep 101

Reasonably Happy with Paul Ollinger ·

2021/03/09

Communicator, author, and pastor Andy Stanley founded Atlanta-based North Point Ministries (NPM) in 1995. Today, NPM consists of seven churches in the Atlanta area and a network of nearly 100 churches around the globe that collectively serve nearly 185,000 people weekly. A survey of U.S. pastors in Outreach magazine identified Andy as one of the ten most influential living pastors in America. Andy holds an undergraduate degree in journalism from Georgia State University and a master’s degree from

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2:17

Crazy Money Trailer

Reasonably Happy with Paul Ollinger ·

2021/03/02

Comedian Paul Ollinger started Crazy Money to explore the connection between money, happiness, work, and meaning through the lens of his guests' expertise and/or money journeys. Preveious interviewees include prominent authors, academics, CEOs, celebrities, and winners of the Nobel Prize, Heisman Trophy, PGA Championship, and Olympic Gold medals, including: Academics: Princeton's Sir Angus Deaton (Nobel laureate) and Peter Singer (“the world’s most influential living philosopher”), Yale’s Laurie

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46:09

LL COOL J on Hip Hop, money and business - Ep 100

Reasonably Happy with Paul Ollinger ·

2021/03/02

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 he burst on the scene at the age of 17, in 1985. For over 35 years, LL has pushed himself to achieve in all that he does while leading with spirit and character. And achieve he has. The two-time Grammy-winner and first ever Hip Hop Kennedy Center Honoree has recorded 14 studio albums, landing massive hits including Going Back to Cali, Mama

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46:29

The Glass Closet: Why Coming Out is Good Business...

Reasonably Happy with Paul Ollinger ·

2021/02/23

“Never tell anyone a secret because they will surely use it against you.” That’s what Lord John Browne’s mother, an Auschwitz survivor, always told her son. The former CEO of BP followed her advice until he was 59 years old when his secret—the fact that he was a closeted gay man—was exposed by an ex-boyfriend in the British tabloids. The revelation resulted in a media storm and Lord Browne’s immediate resignation. Just like that, after almost 40 years of service to his employer, he was out of a job

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58:10

James Altucher Skips the Line - Ep 98

Reasonably Happy with Paul Ollinger ·

2021/02/16

James Altucher is an author, chess master, podcaster, former hedge fund manager, angel investor, and — just to top it off —comedian. Oh, he’s also an entrepreneur who has started 20 companies, 17 of which failed. Over the course of his career, James has made and lost multi-million dollar fortunes “three or four times.” The Wall Street Journal best-selling author of Choose Yourself, Choose Yourself Guide to Wealth, and The Power of No has a new book, Skip the Line that is all about how thinking

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63:06

Love and Money with Rachel Greenwald - Ep 97

Reasonably Happy with Paul Ollinger ·

2021/02/09

Rachel Greenwald is a professional match-maker whose business serves wealthy men looking for love. A graduate of Harvard Business School where she is an Executive Fellow, Rachel is also the New York Times bestselling author of Have Him at Hello and Find a Husband After 35. In today’s episode we discuss the mistakes both men and women make when talking or inquiring about money during courtship. She also divulges the #1 mistake successful women make on first dates, as reported in interviews with over

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45:56

Divorce, Anxiety, and $8B in real estate with Holly...

Reasonably Happy with Paul Ollinger ·

2021/02/02

Holly Parker is one of the most dynamic people I have ever met. A top NYC realtor who has sold over $8 billion in property, she is also a self-made millionaire, consummate connector of people, world traveler, twin mom, and author. In her new book, Back on the Market: A Realtor’s Guide to Love and Life Holly tells the story of her divorce, re-entry into the dating world as an ultra-successful woman, and how she earns the trust of billionaires who purchase $50mm+ apartments. On this week’s episode

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57:03

The Price of College with Ron Lieber - Ep 95

Reasonably Happy with Paul Ollinger ·

2021/01/26

If you have kids in or nearing college age, you HAVE to listen to this episode. Ron Lieber’s new book, The Price You Pay for College contains critical, in-depth information about one of the most important financial decisions your family will ever make. After 15 years of financial reporting, Lieber reports that “No consumer decision inspires more confusion and emotion than the question of what to pay for college,” which is understandable since 4 years at many state schools now costs over $100k in

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52:35

Working Ourselves to Death with Daniel Markovits - Ep 94

Reasonably Happy with Paul Ollinger ·

2021/01/19

Daniel Markovits is the Guido Calabresi Professor of Law at Yale Law School and the author of The Meritocracy Trap in which he outlines the price meritocracy imposes on society. In addition to severely limiting opportunities for the middle and lower classes, our knowledge-based economy “devours the elite” who work brutally long hours at top law firms, investment banks, and consulting companies. And Daniel would know. After all, he acknowledges that he is part of the system that he is criticizing

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49:39

Managing Our Desires with William Irvine - Ep 93

Reasonably Happy with Paul Ollinger ·

2021/01/12

William “Bill” Irvine is an author, philosophy professor, and an active investor who describes his intended audience as "intellectually-upscale readers who have a minimal background in philosophy but who are interested in carefully rethinking the assumptions of everyday life.” (Hey, that’s YOU!) Bill wants to make philosophy accessible and applicable to our everyday struggles. His research can best be described as hybrid, reflecting topics that lie on the border between philosophy and something

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54:27

Getting the Most from Life with Jesse Itzler - Ep 92

Reasonably Happy with Paul Ollinger ·

2021/01/06

Jesse Itzler only eats fruit 'til noon, loves Run-D.M.C., and enjoys living life "out of the box." The author of the New York Times bestseller, Living with a Seal, cofounded Marquis Jet, the world's largest private jet card company which he and his partner sold to Berkshire Hathaway/NetJets. Jesse then partnered with Zico coconut water, which he and his partner sold to The Coca-Cola Company. He’s a former rapper on MTV and wrote and performed the NBA's Emmy Award-winning "I Love This Game" music

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56:26

Peter Singer on the Moral Obligations of Money (from...

Reasonably Happy with Paul Ollinger ·

2020/12/22

The New Yorker called Princeton and University of Melbourne bio-ethicist, Peter Singer “the world’s most influential living philosopher." Time included him on its annual list of the world’s 100 most influential people. Peter has a question for you: Did you know that for the cost of a new television ($600), you can save a life? Here’s another: would it be worth foregoing a nice bottle of wine ($50) to cure someone’s blindness, thus allowing them to return to work and provide for themselves and their

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44:15

The Death of Tony Hsieh with Angel Au-Yeung, David...

Reasonably Happy with Paul Ollinger ·

2020/12/15

Tony Hsieh was the former CEO of Zappos, which Amazon bought for $1.2 billion. With a net worth reported at over $700 million, Tony appeared to have everything anyone could want. However, Tony suffered from severe addiction that pulled him down into a spiral of substance abuse, bizarre behavior, and his eventual death. During the Covid lockdown, Tony bought over $50 million worth of houses in Park City, UT and actually paid his friends to come live near him and “be happy.” He died from injuries

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53:02

Happiness Around the Globe with John Helliwell - Ep 90

Reasonably Happy with Paul Ollinger ·

2020/12/08

John Helliwell is Professor emeritus of Economics at University of British Columbia and editor of The World Happiness Report, a landmark survey of the state of global happiness that ranks 156 countries by how happy their citizens perceive themselves to be. The report has been published since 2012 when the United Nations General Assembly invited countries to measure their citizen’s happiness. And why not? We measure and report GNP, the GDP, the unemployment rate, average income, home sales, but not

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52:23

Real Life Diff'rent Strokes with Kay Madati - Ep 89

Reasonably Happy with Paul Ollinger ·

2020/12/01

Kay Madati was born to a single, Tanzanian mother who died when he was 12. Kay and his brother were then adopted by a very affluent caucasian couple who lived on the Upper East Side of Manhattan. His new family situation was an uncanny mirror to the plot of Diff’rent Strokes, one of the most popular American TV shows of the early 1980s. In a very short period of time, Kay went from a world where “black kids were never supposed to be anything but working class” to attending Riverdale Country School,

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50:58

Giving thanks, literally with A.J. Jacobs - ENCORE...

Reasonably Happy with Paul Ollinger ·

2020/11/24

In this special Thanksgiving encore episode, I talk to A.J. Jacobs about his latest book, Thanks a Thousand: A Gratitude Journey, in which he expresses gratitude to a thousand people who are involved with getting him his morning coffee. A.J. Jacobs is an author, journalist, lecturer and human guinea pig. He has written four New York Times bestsellers that combine memoir, science, humor, and a dash of self-help. He is also editor at large at Esquire magazine, a commentator on NPR and a columnist

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311 results

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