

Today we’d like to introduce you to Paul Ollinger.
Hi Paul, please kick things off for us with an introduction to yourself and your story.
I went to business school at Dartmouth because I wanted a more lucrative career. One night, I hosted our class talent show and told jokes in front of an audience for the first time in my life. That was the day I was bit by the comedy bug (which is NOT what you want to happen if you’re hoping to maximize your income). Over the next few years, I hopped between the digital media business and the comedy world. In 2007, after two years performing as the in-house host at the Improv clubs in Southern California, I decided I need a “real job” again. I joined the Los Angeles-based sales team of a small social networking company called Facebook. I hung onto that rocketship of a company for four and a half years then moved back to Atlanta to be closer to my family. Seven years ago, I recommitted to stand-up comedy and have been at it full-time ever since.
I’m sure you wouldn’t say it’s been obstacle free, but so far would you say the journey have been a fairly smooth road?
I wouldn’t say the road has been particularly rocky, but it certainly hasn’t been a straight line. All of the choices I’ve made have involved some degree of sacrifice, but those choices were mine to make. Nobody forced me to quit comedy to go back to work and nobody made me leave the lucrative technology industry to pursue my passion. That said, gaining proficiency—to say nothing of professional legitimacy—in comedy requires years of your life and thousands of shows, most of which are profoundly unglamorous and pay close to nothing. I recently booked a gig that highlighted “free water and soda” as part of my compensation (I’m not kidding). I’m beyond fortunate to have savings but I’m also a relative beginner at age 52. The older you get, the harder it is to be uncomfortable. But the fact that I seek out discomfort in pursuit of a craft tells me that the job is worth doing.
Appreciate you sharing that. What else should we know about what you do?
When people ask me what I do, I describe my work as “comedian / writer / podcaster.” I love doing stand-up more than almost anything else and am grateful that I’m being invited to perform longer sets in new venues around the country. (Plus, I get free water!)
But I am also fascinated by the conversations around money in our world and thoroughly enjoy producing the Crazy Money podcast on which I explore the connection between money, happiness, work, and meaning. In 125 episodes so far, I have interviewed prominent authors, academics, celebrities, and winners of the Nobel Prize, Heisman Trophy, GRAMMY, PGA Championship, and Olympic gold medals. Guests range from LL COOL J talking about working at the top of the music and TV business for 35 years to my then 92 years old father sharing insights into the financial realities of raising six children (“spend less than you earn.”)
Do you have any advice for those looking to network or find a mentor?
The best way to build your network is to demonstrate your commitment to a craft. Find something worth doing, do it for the right reasons, and keep doing it. Be willing to suck while you put in the hours and the years. Eventually, you won’t suck so much and others will notice. They will invite you to collaborate, offer advice, and return your emails/texts when you seek their input.
Also, be a good person. Opportunities don’t always go to the most talented. They go to people who have enough talent and are also pleasant to be around.
Contact Info:
- Email: paul@crazymoneypodcast.com
- Website: http://paulollinger.com/podcast
- Instagram: https://www.instagram.com/paul_ollinger/
- Facebook: https://www.facebook.com/PaulOllinger/
- Twitter: https://twitter.com/Paul_Ollinger
Image Credits:
JT Walsh