Crazy Money with Paul Ollinger

A Careers podcast by Paul Ollinger

4.9 • 375 ratings

Want connect with Paul Ollinger and email directly about potential partnerships?

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

Puck CEO, Sarah Personette
Published: July 16, 2025
Listen
Weapons Grade Gorgeous w/ Mehran Khaghani | Reasonably Happy with Paul Ollinger
Published: July 6, 2025
Listen
How Victimhood and Narcissism Hold Us Back (w/ Scott Barry Kaufman)
Published: July 2, 2025
Listen
Legacy, Loss, and Being Jewish Now | Reasonably Happy with Paul Ollinger
Published: June 30, 2025
Listen
Jeffery Toobin Exposes Presidential Power | Reasonably Happy Podcast
Published: June 18, 2025
Listen
A Poet’s Wild Past w/ Edward Hirsch
Published: June 11, 2025
Listen
Has Affirmative Action FAILED? | Richard Kahlenberg & Paul Ollinger
Published: June 5, 2025
Listen
Facing Down Trump with Jocelyn Benson
Published: May 30, 2025
Listen
Paul Wants $$ From Qatar (and other hilarious Substack posts)
Published: May 23, 2025
Listen
From Chaos to Cambridge - Rob Henderson
Published: May 14, 2025
Listen

Listen to All Episodes From Crazy Money with Paul Ollinger