Paul Ollinger

Reasonably Happy with Paul Ollinger

Comedy EN ↓ 335 episodes

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

Comedy

Podcast website

words.paulollinger.com

Latest episode

Jul 8, 2026

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Episodes

Stevie Van Zandt takes it all in - Ep 121 28.09.2021

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 Frank Tagliano on Netflix's Lilyhammer. But as he shares in his new memoir, Unrequited Infatuations, Stevie has done so much more with his time on this earth, even if it all didn’t go exactly as he might have hoped.  As a producer, songwriter,...

Net fulfillment v. Net worth with Bill Perkins - ENCORE EPISODE 21.09.2021

(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 his new book, Die With Zero: Getting All you Can from Your Money and Your Life, Bill Perkins challenges you to flout conventional wisdom and spend your money not just before you’re dead, but while you’re still young enough to enjoy it. That...

Gianni Le Nguyen: mom, entrepreneur, Vietnamese refugee. ENCORE EPISODE 14.09.2021

(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 a fishing net, then rowed a basket boat out to meet a more seaworthy vessel a quarter mile offshore. They spent five days battling storms, illness and pirates who took everything Gianni’s dad possessed, including his official papers. Thus be...

Luck v. Hard Work with Robert H. Frank- Ep 120 07.09.2021

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 Success: Good Fortune and the Myth of Meritocracy. Bob cares a great deal about recognizing luck’s role in our success because doing so, he argues, would make us all more grateful, happy, and generous. He also cares because without the “lucky”...

Are Smart People Less Happy? with Raj Raghunathan- Ep 119 31.08.2021

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 can you calm these voices? These are topics we address today with Raj Raghunathan, the author of the book If You’re So Smart, Why Aren’t You Happy? and the creator of the wildly successful Coursera course called A Life of Happiness and Fulfil...

How to Restore Sanity to our Political System with Charlie Wheelan - Ep 118 24.08.2021

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 nudity in either), and The Centrist Manifesto, all of which we discuss in this episode. The Chicago Sun-Times describes Charlie as someone who “combines a razor-sharp mind with a boatload of charm and impressive expertise in economics and f...

Andrew Sullivan Holds Nothing Back - Ep 117 17.08.2021

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 readers. Because his philosophy does not adhere to the predominant narrative of either the Left or the Right, Andrew has made many enemies over the years. He has been called a flaming liberal, a nazi, a misgoynist, a white supremacist, a homoph...

How to Use Your 4,000 Weeks with Oliver Burkeman - Ep 116 10.08.2021

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 management.”  In it, Oliver argues that using your life (4,000 weeks = about 80 years) most meaningfully requires abandoning the illusion that we can—or should try to—get everything done. And that the attempt to do so just leaves us miserab...

A conversation with my producer Mike Carano- Ep 115 03.08.2021

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 that I painstakingly crafted. In this episode we talk about stand-up (I worked at The Improv comedy club for 30 years), the origin and mission of this podcast, and I attempt to imply his wife is a serial killer. If you're reading this, cong...

God Wants You to be Rich with Rabbi Daniel Lapin - ENCORE EPISODE 27.07.2021

(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 children. Therefore, doing business is doing God’s work. In his videos, courses, and books, Thou Shall Prosper and Business Secrets from the Bible, Rabbi Lapin leverages scripture to weave a passionate and refreshing defense of capitalism. In sh...

Overcoming Injury and Life After the NFL with Mohamed Massaquoi - Ep 114 20.07.2021

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 Charlotte, NC, became a star receiver at the University of Georgia, and was a second round draft pick of the Cleveland Browns. Unfortunately, serious concussions cut his NFL career short, and a couple of years later, an ATV accident resulted i...

Why Commitment Matters with Pete Davis - Ep 113 13.07.2021

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 cornerstone of the book, has been viewed over 30 million times.  Pete wants you to commit to some thing, some place, and some one outside of yourself. He believes deeply that doing so will not only be good for your community but it will be GOO...

Does More $ = More Happy? with Sir Angus Deaton - ENCORE EPISODE 29.06.2021

(Originally posted September, 2019...but so worth another listen) Princeton economist and Nobel laureate, Sir Angus Deaton co-authored a famous study concluding that well-being peaks at $75k/year in income. But the results of this research are widely misconstrued and go much deeper than that headline. The first question we wrestle with is "what does it mean to be happy?” We also get into health, o...

How to Change with Katy Milkman - Ep 112 22.06.2021

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 podcast Choiceology, and the author of the best-seller, How to Change: The Science of Getting From Where You are to Where You Want to Be Over the course of her career, she has worked with or advised dozens of organizations on how to spur positi...

Living Rich v. Dying Rich with Joe Duran of Goldman Sachs - Ep 111 15.06.2021

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 Financial Management, which serves clients across 100 locations throughout the United States. A proven entrepreneur, investor, best-selling author, and sought-after industry speaker, Joe previously built Centurion Capital, which he sold to General...

Aging Well with Dr. Laura Carstensen - Ep 110 08.06.2021

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 should think about our health, careers, families, and government programs.  Laura Carstensen is the founding director of the Stanford Center on Longevity and the author ofA Long, Bright Future: Happiness, Health, and Financial Security in an Age...

Hey everyone, this is just a quick update from Paul to talk about how summer travel will affect the production schedule for Crazy Money. 02.06.2021

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Wealth and Existential Despair with Melissa Bernstein - Ep 109 25.05.2021

Melissa Bernstein has great wealth, a wonderful husband, and six healthy children. She has also endured a lifetime of “existential anxiety and depression,” suicidal thoughts, and a feeling that she does not belong on earth.  The Co-founder of Melissa & Doug’s toys describes her brain as a “prison of despair” but that same brain also provides her the “boundless expanse of imagination” that has help...

Moby on Fame, Fortune, Addiction, Animals - Ep 108 18.05.2021

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 depressed.” Having grown up as "poor white trash” in the wealthy town of Darien, CT, Moby's financial status made him feel like a “third-class citizen.” Decades after selling over 20 million albums, winning all kinds of awards, and experiencing "ba...

Life After Paralysis with Maura McVann Coley - Ep 107 11.05.2021

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 high school athlete had to adjust her expectations for senior year, college, and life beyond. On today’s episode, Maura shares with great candor how she adapted logistically and emotionally to her new and very different circumstances. She offe...

Rebounding from Mid-life Melancholy with Jonathan Rauch - ENCORE EPISODE 04.05.2021

(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 happiness that most people experience in middle age and what there is to do about it. Even after achieving all we had ever dreamed of and more, many of us experience a disappointment or melancholy, and question if “this” is all there is to life. ...

How business education builds character with Matt Slaughter - Ep 106 27.04.2021

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 and Paul discuss the role of business education in creating not just savvy business leaders but curious, ethical human beings. Matt shares insights into the challenges the pandemic inflicted on universities, how Covid-19 caused the worst day...

The Science of Well-being with Dr. Laurie Santos - ENCORE EPISODE 20.04.2021

(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 money, more fame, and to be alone, but what will actually make you happy are more social connections and more gratitude. Dr. Santos’ course Psychology and the Good Life—the most popular class in Yale’s history—teaches students to live happier,...

Our possessions, ourselves with Michael Heller & James Salzman - Ep 105 13.04.2021

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 right to blast it out of the sky? (Seems fair to me, but the law says otherwise.) In their new book,Mine!, law professors Michael Heller and James Salzman explore the the concept of ownership and property in ways you have almost certainly not c...

Wall Street, the movie: a panel discussion - Ep 104 06.04.2021

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 cocai...

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