185 episodes

Money makes the world go round – but how does it shape you as a person? Join comedian and former Facebook Sales VP Paul Ollinger as he extracts a wealth of wisdom from CEOs and celebrities, authors and artists, Olympic gold medalists and Nobel Prize winners – each with a unique perspective on the role that money plays in our lives. At a time when talking about personal finance can still feel taboo, Paul offers refreshingly honest discussions about the motivations and misconceptions surrounding money, ultimately asking: what are the ways in which it can (and can’t) bring us happiness? Crazy Money won’t make you rich. But it will definitely make you think (and laugh).

Crazy Money with Paul Ollinger Paul Ollinger

    • Business
    • 4.9 • 391 Ratings

Money makes the world go round – but how does it shape you as a person? Join comedian and former Facebook Sales VP Paul Ollinger as he extracts a wealth of wisdom from CEOs and celebrities, authors and artists, Olympic gold medalists and Nobel Prize winners – each with a unique perspective on the role that money plays in our lives. At a time when talking about personal finance can still feel taboo, Paul offers refreshingly honest discussions about the motivations and misconceptions surrounding money, ultimately asking: what are the ways in which it can (and can’t) bring us happiness? Crazy Money won’t make you rich. But it will definitely make you think (and laugh).

    Growing Up Rich with Kristin Keffeler - S4 Ep 18

    Growing Up Rich with Kristin Keffeler - S4 Ep 18

    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 founder of Illumination360 where she works with ultra high net worth families, including many worth billions of dollars. Her specialty is helping the rising generations create their own identities having grown up with extreme family wealth.
    In this conversation, Kristin and I talked about how her own family's affluence led her into this field; the specific doubts and fears that teen and adult inheritors of generational wealth have to deal with. We talked about the negative messages that society sends to wealthy children, about the balance rising generation members must strike owning their family name, but creating their own. We talked about how all parents—especially wealthier ones—can model financial behavior for their kids. And lastly, we discuss what the NFL Hall of Fame can teach us about the likelihood of measuring up to our wildly successful parents or grandparents.  

    🎧Listen on Apple Podcasts here 🎧
    ✍️Get Paul’s Substack newsletter here.✍️
    🔥Subscribe to us on YouTube here. 🔥

    Follow Kristin Keffeler:
    Website - https://illumination360.com/myth
    The Myth of the Silver Spoon: The Book - https://amzn.to/3i6qFwN

    • 57 min
    Why Boys and Men are Struggling with Richard Reeves - S4 Ep 17

    Why Boys and Men are Struggling with Richard Reeves - S4 Ep 17

    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 Matters, and What to Do about It. You might ask, “Why is this topic relevant to Crazy Money, a podcast about money and happiness, work and meaning?” Because the connection between education, gainful employment and life satisfaction is massive. And on these metrics, the modern male is not doing well. Consider some of these data points: Boys are 50% more likely to fail classes in math, reading and science than girls. By High School, 2/3 of the students in the top 10% of the class ranked by GPA are girls, while about 2/3 of the students in the lowest 1/5 of the class are boys. And education matters. One in three American men with only a high school diploma (10 million men!) are now out of the labor force. They're not unemployed–they're out of the labor force. They're not even counted in the unemployment numbers. And this matters because men without education and jobs do less well as husbands and fathers and thus perpetuate the cycle for their children. Yes, especially for their sons. Perhaps worst of all, men make up 75% of those who die by deaths of despair, i.e. by suicide, or acute substance abuse. The net of it is when you lose hope in the future, you will become increasingly volatile in the present. You've probably read Richard's writing in the New York Times, The Guardian, The Atlantic or the Wall Street Journal, his previous book Dream Hoarders, which The Economist named a Book of the Year.. I'm delighted to have him back on the show.

    🎧Listen on Apple Podcasts here 🎧
    ✍️Get Paul’s Substack newsletter here.✍️
    🔥Subscribe to us on YouTube here. 🔥

    Follow Richard Reeves:
    Twitter - https://bit.ly/3EBSXIo (@RichardvReeves)
    Of Boys and Men: The Book - https://a.co/d/3SnjEhQ
    Website - https://richardvreeves.com

    • 45 min
    The Basic Human Need that Shapes our Identity with Geoffrey L. Cohen - S4 Ep 16

    The Basic Human Need that Shapes our Identity with Geoffrey L. Cohen - S4 Ep 16

    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 physiological requirements, is our need to feel safe as part of a tribe. My guest this week is Geoffrey L. Cohen, the author of Belonging: the Science of Creating Connection and Bridging Divides. Geoff is a professor of Psychology and Organizational studies at Stanford University in Palo Alto, California. In this conversation, he and I talk about what it means to belong to a place, an organization, a family or a movement; We explore how belongingness and identity are intermixed, and what implications that has for discussing politics and other beliefs with people who have differing points of view. We talk about how to design diversity training so it doesn't alienate half the room (maybe we should call it “Belongingness Training”). We also talk about what groups you'd rather not belong to, because while belongingness is important, some tribes are better than others!

    🎧Listen on Apple Podcasts here 🎧
    ✍️Get Paul’s Substack newsletter here.✍️
    🔥Subscribe to us on YouTube here. 🔥

    Follow Geoff Cohen:
    Twitter - bit.ly/3UVv5F4
    Website - www.geoffreylcohen.com

    • 57 min
    The Hedge Fund Legend Who Just Wants to be Loved with Hugh Hendry - S4 Ep 15

    The Hedge Fund Legend Who Just Wants to be Loved with Hugh Hendry - S4 Ep 15

    Former hedge fund manager Hugh Hendry grew up working class in Glasgow, Scotland. His anxiety, detachment from money, and passionate observations of life led him to hypotheses and market positions others couldn’t see. In 2008, when the rest of the world was melting down, Hugh’s Eclectica Asset Management returned over 30%. As great as the money was, he says what drives him is a profound need to be loved. Today, Hugh develops property in St. Barths where he lives full time.

    In this conversation, Hugh shares anecdotes of Scottish thrift that will make you laugh, an honest description of how it feels to lose millions of other people's dollars, why closing his hedge fund felt “as if you've died in Mortal Kombat,” and why we should all be mindful of “the profound wrongness of today.” We spoke at the Stansberry Research conference in Boston in October.

    🎧Listen on Apple Podcasts here 🎧
    ✍️Get Paul’s Substack newsletter here.✍️
    🔥Subscribe to us on YouTube here. 🔥

    Follow Hugh Hendry:
    The Acid Capitalist podcast - https://apple.co/3FX3D5v
    Twitter - https://bit.ly/3UKgfBg
    Instagram - https://bit.ly/3UDczkA
    Website - acidcap.com

    • 48 min
    Profits Over People: the Sacklers, OxyContin, and America's Opioid Epidemic with Barry Meier - S4 Ep 14

    Profits Over People: the Sacklers, OxyContin, and America's Opioid Epidemic with Barry Meier - S4 Ep 14

    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 Opioid Epidemic, which explores how the Sackler family's greed catalyzed a plague of addiction and death that has destroyed families and whole communities across the country.

    Between 1999 and 2000, 564,000 Americans died from an opioid overdose. In 2020, the most recent year for which statistics are available, there were over 68,000 opioid overdoses in the U.S. That's 188 per day and each one of these deaths represents a son or daughter, a brother or sister or a mother or father, who is not coming back. People died of opioid overdoses before the 1996 launch of OxyContin, but it’s clear that Oxy and Purdue Pharma’s (owned by the Sacklers) aggressive and deceptive marketing practices threw gasoline on a spark that has turned into a raging wildfire. In 2023, Netflix will launch a miniseries based on Pain Killer.

    In our conversation today, Barry and I discuss the Sacklers’ family legacy of ethically dubious marketing of pharmaceuticals and how they made tens of billions of dollars selling OxyContin using the same techniques, like pushing free samples, knowing that the drug was quite addictive. We discuss how and why the FDA approved claims that OxyContin was less prone to addiction in the complete absence of evidence proving that it actually was. And lastly, we discuss the extent to which OxyContin kicked off this opioid epidemic for which there is no clear way out.

    🎧Listen on Apple Podcasts here 🎧
    ✍️Get Paul’s Substack newsletter here.✍️
    🔥Subscribe to us on YouTube here. 🔥

    Follow Barry Meier:
    barrymeier.com
    nytimes.com/by/barry-meier
    Pain Killer: The Book - https://a.co/d/b9cEPHS

    • 45 min
    The Status Game: Money, Status & Social Hierarchy with Will Storr - S4 Ep 13

    The Status Game: Money, Status & Social Hierarchy with Will Storr - S4 Ep 13

    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 probably know the answer: above some, below others, and probably on about the same level as most. Perhaps you'd follow up with questions like “Do you mean who has more money? Or who has more recognition in the community or who's more attractive or physically fit?” This request for clarification demonstrates the nature of status, and how we go about gaining it and retaining it, whether or not we are conscious of our efforts to do so.

    My guest this week is Will Storr. He's the author of a fascinating book called The Status Game. The author of six critically acclaimed books, including The Status Game, Selfie, and The Science of Storytelling, Will’s writing has appeared in The Guardian, The Sunday Times, The New Yorker and the New York Times. And his journalism has been recognized with awards from the National Press Club, the One World Press and Amnesty International. If I haven't yet convinced you of his status, I’ll also share that he's a great looking guy who grows giant yams. (You'll understand that reference about 20 minutes into the episode.)

    In this conversation, Will and I discuss why status matters; Whether the pursuit of status is a fool's game for small minded people with totally fragile egos; We talk about a totally bizarre source of status in Polynesia that demonstrates the arbitrariness and locally relative nature of status. We talk about whether it's better to be a big fish in a small pond or a small fish in a big pond. We talk about how the quest for status shows up in politics and religion and boy does it ever and lastly, we discuss how the thirst for status among even the most rich and famous among us, like Sir Paul McCartney, demonstrate the insatiable need for this elusive and addictive drug that is STATUS.

    🎧Listen on Apple Podcasts here 🎧
    ✍️Get Paul’s Substack newsletter here.✍️
    🔥Subscribe to us on YouTube here. 🔥

    Follow Will Storr:
    Twitter - https://bit.ly/3D84YVg (@wstorr)
    The Status Game: The Book - https://amzn.to/3TnazNi

    • 53 min

Customer Reviews

4.9 out of 5
391 Ratings

391 Ratings

want to travel for free? ,

Somewhat funny host

Okay fine he made me chuckle during his Ken Honda interview as well as his chat with Rabbi Daniel Lapin. The theme is a great spin on how much weight we place on money’s ability to make us happy.

Ps: Paul is a funny comedian just for clarity

Gamereviewer7 ,

Compelling and thought provoking

This is one of my favorite podcasts. Paul has a great interviewing style and compelling guests. I enjoy hearing his personal story as well. Great talent. Please keep them coming!

pffan22 ,

Great interview

Came across the interview with Sam @ Financial Samurai - loved it. Thanks for hosting!

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