A Grown Man’s Guide to Living Well

Career Second-Acts and Living Your Purpose | Paul Ollinger

How a corporate refugee-turned-comedian learned to redefine success

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Hey gents, hope you’re having a great week. You may have noticed, I’ve slowed down a bit in creating new episodes. Well, this will actually be my last episode for The Distilled Man Podcast. And I think it’s a fitting topic. Today, we talk with the multitalented Paul Ollinger about reinvention, career second-acts, fatherhood, and living your purpose.

Paul Ollinger

Paul Ollinger is a nationally-touring comedian, podcaster and corporate refugee. After 15 years selling advertising for companies like Yahoo! and Facebook (where he was employee #250) Paul launched the comedy career that has taken him all over North America, opening for legends like Norm Macdonald, Dave Attell, Daniel Tosh, and Roseanne Barr.

He has performed in the Laughing Skull, Asheville, Big Pine, Cleveland, DC, San Diego, and North Carolina comedy festivals. Earlier this year, he headlined the legendary Carolines on Broadway in New York City.

Paul is the host of the Crazy Money podcast in which he interviews celebrities, authors, and everyday people to explore how money affects their decision-making and happiness. He lives in Atlanta with his wife, two kids, and two goddamn French bulldogs.

Success feels like ability to do what you want to do, but doing thing you know you want to do as opposed to things you’re supposed to be doing.”

Episode Highlights

  • Paul’s first taste of comedy in business school
  • How Paul’s upbringing affected his views on wealth
  • Should you take a sabbatical to pursue your dream?
  • Paul’s return to the corporate world at a fledgling company called “Facebook”
  • The importance of consistently showing up to improve your craft
  • Defining your worth and knowing your limits
  • Understanding wealth and the importance of identifying what you want
  • How to create greater purpose in your life

Resources Mentioned

Connect with Paul

About Kyle Ingham

Kyle Ingham is the Founder and Editor of The Distilled Man, an online channel that helps everyday guys become well-rounded gentlemen. Kyle is a husband, new father, blogger, podcaster, and a recovering advertising executive. For the past 7 years, he's been helping men learn the essential skills and knowledge they need to become better, more confident men. Kyle enjoys Bourbon, burritos and the occasional pirate joke. He lives in the San Francisco Bay Area with his wife and son.
 
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Comments

  1. Chaitanya K says

    Hi Kyle,
    I’ve been listening to your podcasts the last year and they were really great.
    I’m very sad that you’ve decided not to do this anymore. May I ask why?
    I wish you a very successful career/path beyond “The Distilled Man”!

    Reply

    • Kyle Ingham says

      Thanks Chaitanya! I just decided that I needed to hit “pause” and get some perspective after doing this for a few years. Online content is a difficult business, and trying to keep up can be a grind. I’m happy to just “be” for awhile.

      Reply

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