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 backPushing 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 worldThe difference between walking away from something and walking towards something newWhy Paul started his podcast Reasonably Happy and what it means to be authentically fulfilledFind Paul:www.paulollinger.comIG: @paul_ollingerX: @Paul_OllingerLinkedIn: Paul OllingerFollow Lydia:www.lydiafenet.comIG: @lydiafenetLinkedIn: Lydia FenetQuestions or comments, we'd love to hear from you...send us a text!Record a question here so we can answer it on the next episode of Claim Your Confidence.To stay up to date with Claim Your Confidence and get all the behind-the-scenes content, follow us on Instagram and on YouTube.If you enjoyed this episode, please subscribe and leave a rating and review on Apple or Spotify or where ever you get your podcasts.Recorded at The Newsstand Studios at Rockefeller Center.Thank you for listening.
No persons identified in this episode.
This episode hasn't been transcribed yet
Help us prioritize this episode for transcription by upvoting it.
Popular episodes get transcribed faster
Other recent transcribed episodes
Transcribed and ready to explore now
3ª PARTE | 17 DIC 2025 | EL PARTIDAZO DE COPE
01 Jan 1970
El Partidazo de COPE
13:00H | 21 DIC 2025 | Fin de Semana
01 Jan 1970
Fin de Semana
12:00H | 21 DIC 2025 | Fin de Semana
01 Jan 1970
Fin de Semana
13:00H | 20 DIC 2025 | Fin de Semana
01 Jan 1970
Fin de Semana
12:00H | 20 DIC 2025 | Fin de Semana
01 Jan 1970
Fin de Semana
迷你心身 38. 我們有什麼怪癖
21 Dec 2025
心身難路上的身心科