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October 29, 2024 36 mins

Mastering any new skill can take years, and that was Paul Ollinger’s experience when he first started doing comedy. After working in sales leadership for fifteen years at companies like Yahoo and Facebook, Paul took the leap to pursue his passion for stand-up comedy and has since opened for top comics like Daniel Tosh and Chelsea Handler, and headlined the legendary Carolines on Broadway in 2019. Paul is also an author, podcast host, and keynote speaker, and his podcast, Reasonably Happy (formerly known as Crazy Money), explores the connection between money, happiness, work, and meaning. In this episode, we discuss Paul’s career path as a comedian, what the mantra “dare to suck” means, and becoming yourself onstage. 

Don’t miss this interview where we talk about:


  • How Paul discovered his love for comedy while in business school, why he stepped away from it once, and what eventually brought him back
  • Pushing the boundaries, taking risks, and finding your lane 
  • Paul’s experience working as one of Facebook’s first 250 employees and how he refound his footing after retiring from the corporate world
  • The difference between walking away from something and walking towards something new
  • Why Paul started his podcast Reasonably Happy and what it means to be authentically fulfilled


Find Paul:

www.paulollinger.com

IG: @paul_ollinger

X: @Paul_Ollinger

LinkedIn: Paul Ollinger


Follow Lydia:

www.lydiafenet.com

IG: @lydiafenet

LinkedIn: Lydia Fenet

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Recorded at The Newsstand Studios at Rockefeller Center.

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