Paul Ollinger: Comedy, Tech, and the Pursuit of Happiness

My guest on episode 380 of #thePOZCAST is Paul Ollinger. After 15 years in sales at companies like Yahoo! and Facebook, Paul bailed on the corporate world to chase the comedy dream, which has seen him headline top clubs like Carolines on Broadway, West Side Comedy Club (NYC), Cobbs (SF), and Zanies (Nashville). He has performed at the Hollywood Improv and Comedy Cellar and shared the stage with stars such as Norm Macdonald, Dave Attell, and Chelsea Handler.

Paul has also opened for major music acts, including Styx and Collective Soul, and performed at some of the biggest festivals, clubs, the smallest theatres, dive bars, and everything in between.

Paul is also the host of the Crazy Money Podcast. In conversations with some of the world's most interesting people, he explores the connection between money, happiness, work, and meaning. Previous guests include Judd Apatow, LL Cool J, Moby, and winners of the Nobel Prize, Heisman Trophy, PGA Championship, and Olympic gold medals.


In this engaging conversation, Adam Posner interviews Paul Ollinger, a former tech executive turned comedian and podcaster. They explore Paul's journey from a corporate career at Yahoo and Facebook to pursuing his passion for comedy. The discussion delves into his early influences, the challenges of transitioning to stand-up, and the lessons learned from both the tech and entertainment industries. Paul shares insights on success, happiness, and the importance of embracing the journey, while also offering advice for aspiring comedians.

Follow Paul on Instagram: https://www.instagram.com/paul_ollinger/

Follow him on Substack: https://paulollinger.substack.com/

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