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Does Money Equal Happiness? Comedian Paul Ollinger (ep. 644)

Paul Ollinger

John O’Leary welcomes Paul Ollinger on the Live Inspired Podcast to discuss how money’s only one attribute to a multivariable equation for happiness in life.

Paul Ollinger is a nationally-touring comedian and a former Facebook VP of Sales. As one of Facebook’s first 250 employees, Paul managed a team that generated about 35% of the company’s revenue. After retiring from Facebook at 42, Paul found himself bored, lonely and unfulfilled. Wondering why the wealth windfall he had so long pursued didn’t deliver the contentment he expected, Paul launched the Crazy Money Podcast to explore the connections between money and happiness.

Today, Paul shares how his childhood shaped his traditional conservative economic outlook, how he weighed his success in how much money he made, and ultimately how he learned that money’s only one attribute to a multivariable equation for happiness in life.

My friends, you’ll leave this conversation with a newfound appreciation for the complexities of happiness beyond wealth.

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  • As one of six kids, Paul sees it as one of the best gifts I’ve been given in life when taking care of aging parents.
  • “We can’t afford that” mentality: Growing up, Paul recalls a subtext of financial stress and believed that if he made a lot of money, he’d have nothing to worry about. As an adult, Paul recognizes that money’s only one attribute to a multivariable equation for happiness in life.
  • Feeling a tension between the role he thought he was supposed to play and the person he wanted to be, Paul left the corporate world.
  • After earning his MBA from Dartmouth, Paul worked for Launch CD-ROM Magazine with Dave Goldberg and Bob Roback.
  • Paul left Yahoo! to move to Los Angeles where he opened for Norm MacDonald, Roseanne Barr and other famous comedians with hundreds of sets in two years.
  • As big as MySpace: Two years into developing who he was on stage, Paul got engaged and because his traditional conservative economic outlook, he took a job as an early employee of Facebook.
  • “Today, Facebook has arguably, next to Google and the printing press, the most important communication tools in the history of the planet and the most effective advertising tools in history.”
  • Rooted in the quarter-to-quarter mindset from his past roles, Paul struggled to see the future-oriented focus of Mark Zuckerberg and Facebook. He soon left, returned home to Atlanta to spend time with his aging parents and his immediate family.
  • Research shows that those who retire early, die early. In his work through writing and the Crazy Money Podcast, Paul wants to help others be conscious of the things they’re getting from work that are beyond a paycheck, including purpose, belonging and self-esteem.
  • Be Uncle Fred: Paul reminds us that opportunity isn’t going to find us, we have to create it and when you get clear on what you stand for, you’ll find fellow travelers.
  • Declining marginal return of stuff: Paul reminds us that where money helps solve our problems and really brings us joy in life, is really at the lower end when you can replace chaos with reliability.
  • What to do when when things aren’t going right? Acknowledge it.
  • “You can’t wait for the outside world to love you and to applaud you. You just gotta keep working on yourself and striving to get better.”

Did you enjoy today’s conversation? 

You’ll love my conversation with Sebastian Maniscalco. Named “the hottest comic in America”, Sebastian shares how perseverance and hustle have been the key ingredients to attaining the success he once only dreamed of, the challenges that come with it and where he finds inspiration. Listen to Sebastian Maniscalco on ep. 334 now.


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  1. Q. What is the best book you’ve ever read?
    A. Red Notice by Bill Browder and The Lives of Stoics by Ryan Holiday.
  2. Q. What is a characteristic or trait that you possessed as a child that you wish you still exhibited today?
    A. Earnestness.
  3. Q. Your house is on fire, all living things and people are out. You have the opportunity to run in and grab one item. What would it be?
    A. My laptop.
  4. Q. You are sitting on a bench overlooking a gorgeous beach. You have the opportunity to have a long conversation with anyone living or dead. Who would it be?
    A. My parents.
  5. Q. What is the best advice you’ve ever received?
    A. Think before you talk.
  6. Q. What advice would you give your 20-year-old self?
    A. You'll get there. Take your time.
  7. Q. It’s been said that all great people can have their lives summed up in one sentence. How do you want yours to read?
    A. He did his best.