Paul Ollinger is a nationally-touring stand-up comedian, podcaster, author, and former digital sales leader. He is the host of the Crazy Money podcast, where he explores the connection between money and happiness through the lens of his guests’ expertise and money journeys.
Where did you grow up and what was your childhood like? Did you have any particular experiences/stories that shaped your adult life?
I grew up as the fifth of six kids in a big, loving family in suburban Atlanta in the 1970s and 80s. My parents—who stayed together for 55 years until my mother died—were smart, kind Depression-era people who held down jobs but also feared that it could all go away at any time. We never missed a meal and my parents passed up any luxuries for themselves to pay the Catholic school tuition for all six of us. For this or some other reason, there was a pervasive sense of financial anxiety in our home. I remember the first time I got a cavity filled, my father told me, “don’t get the Novocain – it’s $25.” As the dentist’s drill tore into my virgin molar, I writhed in agony and pledged to myself, “someday, I’m going to make some damn money.”
What is something you wish you would’ve realized earlier in your life?
It is not only okay to make your own path, it is absolutely critical in fulfilling the opportunity you have to be uniquely you. (I actually just wrote that – I didn’t read it on a Successories poster.)
What are bad recommendations you hear in your profession or area of expertise?
Without going into the specific bad advice available in the comedy world, be skeptical when anyone tells you there is only one way to achieve success. In general, hard work and focus are hard to beat, but few people’s career trajectories are smooth, uninterrupted lines “up and to the right.” I was in the corporate world, then quit to do comedy. I gave up on comedy after two years because I was getting married and wanted a more stable job. I stumbled into a gig as the 250th employee at Facebook where I worked for 4.5 years. I left a ridiculous amount of money on the table on Facebook because I wasn’t feeling it anymore.
Eventually, I recommitted myself to comedy. I had a lot of momentum at the end of 2019….then 2020 happened. Now we’re back and I’ll be the opening act at some big outdoor arenas this summer. You never know how it’s all going to work. Just do whatever you want to do for the right reasons, be open to opportunity, and keep moving forward.
Tell me about one of the darker periods you’ve experienced in life. How you came out of it and what you learned from it?
Ironically, one of the darker times for me was right after retiring early from Facebook at age 42. I had “hit my number” (by a lot) and figured, “I’m rich – all my problems are solved.” But when I bailed on my job without a plan, assuming money was all that mattered, I found myself bored and lonely. I missed my work friends, my sense of belonging to a team, and the pride of working on and solving difficult problems. It’s a widely-held belief in America that money is the most important thing in life. And while it is important, past a certain point, money isn’t going to solve your problems or make you feel like your life matters. I pulled out of this slump when I summoned the guts to commit myself to writing and comedy. This brings me to another Epictetus quote I love: “If you want to improve, be content to be thought foolish and stupid.”
What is one thing that you do that you feel has been the biggest contributor to your success so far?
I have always been surrounded by good people. From a really solid family to great teachers, coaches, and the best friends a person could have. In addition to my own folks, I remember admiring my friends’ parents who were not just successful but also kind and attentive to their children. I’d think, “that’s what I want to be like when I grow up.”
What is your morning routine?
Half the time, I’m up at 5:00 or 5:15. I brush my teeth, make coffee, and focus on writing (jokes, my Medium column, or book manuscript) until I wake the kids up at 6:40. It’s the most peaceful, most productive time of the day. The other half of the time, I’ve stayed up late performing comedy so I sleep until 6:30.
What habit or behavior that you have pursued for a few years has most improved your life?
Meditation. I started meditating 4-6x per week about 3 years ago and it has made a big difference. Paired with reflective writing and reading, taking 15-20 mins to be present helps me stay aware, grateful, and—to a not-perfect extent—out of my own head. I think the big misconception is that meditation is a woo-woo, new age practice for flakes, but that couldn’t be less true. I think it would have helped me significantly if I had started while working in the corporate world.
What are your strategies for being productive and using your time most efficiently?
I have a lot of different creative balls in the air, so the focus is pretty important and an area where I can improve a lot. I have an embarrassing number of documents and browser tabs open as I write this. It’s my virtual ‘to-do’ list, but it’s counter-productive. I am doing better with my recently-imposed “follow up or close the window” strategy and I recently reduced my email Inbox to under 40 messages, which makes me Super-human.
What book(s) have influenced your life the most? Why?
To start, I’ll define “most influential” as those which blew my love of reading wide open. I read Pat Conroy’s The Lords of Discipline and The Great Santini the summer before 9th grade, and I was hooked. Prior to encountering Conroy, I had never lost myself in a “page-turner.” From that point on, I dabbled in Hemingway, mainlined Fitzgerald, and read everything Nick Hornby released (except the newest one, which is sitting on my bedside table). Donna Tartt’s The Secret History turned my brain inside-out.
More recently, I tend toward non-fiction. I’ve re-read Steven Pressfield’s The War of Art three or four times. It’s outstanding and required reading for anyone who thinks they might be an artist of any kind. Robert Wright’s Why Buddhism is True helped demystify meditation (see below) and Ryan Holiday’s books on Stoicism (Ego is the Enemy, The Obstacle is the Way, Stillness is the Key) have encouraged millions, including me, to lead more meaningful lives with or without traditional, western religion.
I also read a lot of books by authors I interview on my podcast, Crazy Money. Two that I can’t get out of my head include Jonathan Rauch’s The Happiness Curve: Why Life Gets Better after 50 and Bill Perkins’ Die With Zero: Getting All You Can From Your Money and Your Life.
Do you have any quotes you live by or think of often?
“Comparison is the thief of joy.” – Teddy Roosevelt
“Wealth consists not in having great possessions but in having few wants.” – Epictetus
The purpose of my podcast is to explore the connection between money, happiness, work, and meaning. When we examine why money leaves us wanting, we find two main reasons:
1. We don’t evaluate our lives objectively, especially when it comes to our allotment of status and resources. We compare ourselves to others, and almost always against those who have more. This leaves us with an unrealistically pessimistic view of how our lives are going, stealing our joy.
2. The better we do, the more we compare ourselves with others who are also doing well. We begin to crave things we didn’t even know existed years prior. Thus, our infinitely-expanding desires can never be satisfied and the only way to feel wealthy is to control our wants.