About Paul Ollinger: Paul Ollinger is a nationally touring comedian and author of Reasonably Happy: The Skeptic's Guide to Achievable Contentment. He has performed over 1,000 shows, including at top festivals, and opened for legends like Norm MacDonald, Dave Attell, and Roseanne Barr.
A former Facebook VP of Sales and one of its first 250 employees, Paul managed a team responsible for 35% of the company's revenue. After retiring at 42, he launched the Crazy Money podcast to explore the connections between money, happiness, and meaning, featuring guests like Judd Apatow, LL Cool J, Dr. Drew Pinsky, and Guy Raz.
In this episode, Shawn and Paul Ollinger discuss:
- The nuanced relationship between wealth and happiness
- The identity and lifestyle challenges of early retirement
- Importance of purpose and planning beyond financial security
- Using humor as a lens for self-reflection and fulfillment
"Work provides you with a place in the world, peers that sometimes can be frustrating but are really your community, whether you believe it or not." — Paul Ollinger
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