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

From Prison to Oprah
Published: August 20, 2025
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Would you vote for Jesus?
Published: August 15, 2025
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Tribalism is Dumb (w/Andrew Heaton)
Published: July 30, 2025
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Puck CEO, Sarah Personette
Published: July 16, 2025
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Weapons Grade Gorgeous w/ Mehran Khaghani | Reasonably Happy with Paul Ollinger
Published: July 6, 2025
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How Victimhood and Narcissism Hold Us Back (w/ Scott Barry Kaufman)
Published: July 2, 2025
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Legacy, Loss, and Being Jewish Now | Reasonably Happy with Paul Ollinger
Published: June 30, 2025
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Jeffery Toobin Exposes Presidential Power | Reasonably Happy Podcast
Published: June 18, 2025
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A Poet’s Wild Past w/ Edward Hirsch
Published: June 11, 2025
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Has Affirmative Action FAILED? | Richard Kahlenberg & Paul Ollinger
Published: June 5, 2025
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