

#378 Paul Olinger - The Truth About Western Society, Media, and Education
Aug 29, 2025
Paul Ollinger, a comedian and former Facebook executive, shares his fascinating journey from corporate tech to stand-up comedy. He reflects on the evolution of social media and its effects on society, discussing political polarization and the challenges of identity politics. The conversation tackles media bias and the decline of neutral news, emphasizing the importance of constructive dialogue. With a touch of humor, Ollinger highlights the complexity of modern issues while advocating for optimism and resilience in navigating societal challenges.
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Early Life And Money Realization
- Paul Ollinger grew up in suburban Atlanta in a large Catholic family and felt ambition baked from frugality.
- He made money at Facebook but discovered wealth did not deliver the expected happiness, prompting his podcast on money and fulfillment.
Accidental Entry Into Comedy
- Paul accidentally discovered comedy after co-hosting a talent show and getting huge laughs for mocking friends.
- He pursued digital media for stability while keeping comedy as a passion before later re-entering corporate tech.
Joining Facebook Early
- Paul joined Facebook as roughly the 250th employee and ran West Coast sales after being recruited by a former Yahoo colleague.
- He experienced the startup's youthful culture and direct connection to product teams early on.