What happens when you’ve checked every financial box—and still feel lost? Carl sits down with comedian, former Facebook exec, and Reasonably Happy author and podcast host Paul Ollinger to explore the emotional weight of money and identity.

Paul shares what it felt like to walk away from Silicon Valley at 42, why he once considered himself a "rich loser," and how chasing fulfillment led him back to the stage as a stand-up comedian. They unpack the psychology of wealth, the shame and status we attach to our financial lives, and why we often struggle to say, “I have enough.”

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Follow Paul @paul_ollinger 

Listen to Paul’s podcast Reasonably Happy

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Cover Art: Josh Passler - TheFinArtist.com

Music Credits: 

Alexandra Woodward / Rabbit Reggae / courtesy of www.epidemicsound.com

Cody Francis / Wherever You’re Going / courtesy of www.epidemicsound.com

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