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March 3, 2025 49 mins

Paul Ollinger is a nationally-touring comedian and writer. He has done more than 1,000 shows including the Limestone, BigPine, Laughing Skull, and Boston Comedy Festivals. Paul’s comedy is poignant and cutting, but what also distinguishes Paul is his previous life as a former Facebook VP of Sales, and one of Facebook’s first 250 employees.


After cashing in and retiring from Facebook at 42, Paul found himself bored, lonely, and driving his wife crazy. Wondering why the wealth windfall he had so long pursued didn’t deliver the contentment he expected, Paul launched the Crazy Money Podcast (now called Reasonably Happy) that began his lifelong dream of being a comedian. His work explores the connections between money, happiness, work, and meaning.

 

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