Crazy Money with Paul Ollinger

A Careers podcast by Paul Ollinger

4.9 • 375 ratings

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Crazy Money exists to promote financial wisdom and better living through no-holds-barred conversations about the role of money in our lives. Listen as comedian and former Facebook sales VP, Paul Ollinger interviews entrepreneurs, celebrities, authors, artists, and others with a unique perspective on money, wealth and careers. He will address how they’ve gotten money right or wrong, and discuss the misconceptions and mistakes that have led them to where they are today. The tone is always honest, irreverent, and funny.

Recent Episodes

High Net Worth Divorce with Laura Wasser
Published: December 3, 2025
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Surviving the College Application Process w/ Jeffrey Selingo
Published: November 19, 2025
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Paul’s Insights into NYC, Email, and Estate Planning
Published: November 12, 2025
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Confronting Mortality with Thad Reichley
Published: November 5, 2025
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Walking Away from Fame and Money with Rachel Heck
Published: October 29, 2025
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Family, Politics & The American Dream with Raj Goyle | Reasonably Happy
Published: October 22, 2025
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Stoic Street Smarts w/ Ed Latimore
Published: October 15, 2025
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Soul on Fire w/ John O’Leary (Encore episode)
Published: October 8, 2025
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Why You Will Never Feel Rich w/ Daniel Crosby
Published: October 1, 2025
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Why Two Parents Are Better Than One w/ Melissa Kearney (Encore)
Published: September 24, 2025
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Listen to All Episodes From Crazy Money with Paul Ollinger