Meet Paul Ollinger: Comedian, Host of the Crazy Money podcast

We had the good fortune of connecting with Paul Ollinger and we’ve shared our conversation below.

Hi Paul, what role has risk played in your life or career?
The biggest risk I have strived to avoid is regretting on my deathbed the way I lived my life, or—more near term—that feeling of waking up in the morning and dreading what I had to do that day. When you start to view your work through this lens, you give yourself permission to do the things that are the truest expression of who you are as opposed to those things that might generate the most money or the highest social / professional status. Ironically, if you keep at it, others really begin to respect what you’re doing and think, “I wish I could do that.”

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
Mark Manson, author of the best-seller, The Subtle Art of Not Giving a F*ck advises that we shouldn’t ponder which activities give us the most joy. Rather, we should decide which form of pain we are willing to endure: to ask ourselves, “which values am I willing to suffer for?” For me, those values are self-discovery and truth-telling in the form of comedy, writing, and podcasting. So I traded the paycheck, predictability, and security of the corporate world for the pain of uncertainty, self-doubt, and suckitude that are your unavoidable companions on the road toward proficiency in any new craft.

But the rewards are just phenomenal. There is nothing like making a huge (or tiny) group of people laugh when you, for the briefest of moments, change the way they see the world. Few things compare to complete strangers sharing your writing with their friends saying, “this guy is willing to say what needs to be said.” And when academics, authors, or artists I admire reach out asking to be on my podcast because they appreciate what I’m trying to do, well, that’s just the best.

I’ve worked as a stand-up comedian full-time for a total of eight years now. As I improve and as I start to see the “pain” as “opportunity,” more good things happen. The calibre of guests on the podcast is outstanding, and I’m landing more and more interesting comedy gigs. I opened for the band, Collective Soul for three awesome shows last month. And this summer I’ll be opening on the road for Styx. It’s going to be an adventure.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
Many of my friends are golf fanatics, so in addition to sneaking onto some of the area’s great private clubs and daily fee courses, I would pull every string I could find to get them onto historic East Lake Golf Club. They’ve all seen it on TV watching the annual TOUR Championship, and would relish playing the uphill par-3 #9, the picturesque par-5 #18 finishing hole, and #8 (formerly #17) where Bill Haas made one of the greatest shots in history.

Speaking of history, we would spend a lot of our days learning (and eating). We’d tour the Old Fourth Ward, visit the King Center and Ebenezer Baptist Church, then have lunch at Krog Street where I would enjoy meat and bread at Fred’s, followed by a scoop of the latest batch at Jeni’s Splendid Ice Cream. We’d walk off our lunch on the way to Oakland Cemetary and say hello to Margaret Mitchell, Bobby Jones, and Maynard. After paying our respects, we’d head across the street to sip a 420 on the upstairs deck at Six Feet Under. We’d come home, nap and wrap up the busy day with a fire on our back porch in Brookhaven.

Friday night would be dinner at Ecco midtown for a little grilled pulpo + pappardelle + Priest Ranch cab, followed by the Best of Atlanta comedy show at Laughing Skull Lounge, which is just around the corner on Peachtree.

Saturday would be more exploring midtown, walking / biking on the Belt Line, kicking about Piedmont Park, enjoying a tasty IPA at New Realm or Orpheus. That night we’d grab a burger at the Vortex in Little 5 then take in comedy or music at Variety Playhouse.

On Sunday, we’d wear out our kids with an obligatory morning walk up Stone Mountain, followed by biking the trails at Big Creek Park in Roswell.

(I’m exhausted just thinking about it.) The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
There’s a lot of talk about “privilege” these days, and I think the greatest source of privilege of my life was being born to two parents who wanted me, loved me, prioritized my education over their material comfort, and modeled fidelity and commitment for 55 years until death did they part. Despite the occasional chaos of a large brood (6 kids, lots of extended family), our home was a safe environment where I knew I was part of a cohesive clan. You can’t overstate the value of this kind of upbringing, and my wife and I are trying to replicate the most important elements of this for our own children.

Speaking of my wife, I couldn’t do what I’m doing if I weren’t married to someone who has my back and is in my corner both emotionally and logistically. Doing comedy requires a lot of travel and late nights, which means she has to cover for certain parenting events or attend many social events solo. It also requires being okay with the foregone income from a corporate job while I work to establish myself in the creative world. If your partner is not on board with you chasing your dream, it will not go well.

Website: https://paulollinger.com/

Instagram: https://www.instagram.com/paul_ollinger/

Linkedin: https://www.linkedin.com/in/paulollinger/

Twitter: https://twitter.com/Paul_Ollinger

Facebook: https://www.facebook.com/PaulOllinger/

Other: Medium: https://paulollinger.medium.com/

Image Credits
Mike Carano, Sam Silverstein, TBD (the one from Laughing Skull Lounge – I will find the photog’s name prior to publishing)