Kevin O'Leary | Crain's

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Kevin O'Leary


O'Leary Financial Group offers a wide range of income generating mutual funds and investment strategies. 

The Mistake:

Working for someone else. In high school, the summer between 10th and 11th grades, I got my first real job working at a place called Magoo's Ice Cream Parlour. I was the head scooping guy; there was always a line of people at that place.

On my second day, the owner said to me, “Before you go today, you've got to take all the gum out from between the grout [on the floor]. Here's a tool, here are gloves and … you need the stuff that dissolves gum." I said, "No. No. No. I was hired to be an ice cream scooper. And, I'm good at it. These lines are short. But I don’t do gum on the floor."

We had a bit of an argument; it was my second day. But I figured it shouldn’t be an issue because I am so great at scooping. She fired me. It was totally humiliating. I said to myself then, "I will never work for anybody ever again. Ever." And, I never have. I don’t like people controlling me, and it's a powerful enough motivator to make myself do my own thing 100 percent of the time.  

You have to decide if you are a gum scraper or you tell people to scrape gum.  


The Lesson:

You don’t have to ever work for anybody. Do something on your own. I think a third of people in the world are entrepreneurs, and they can create their own outcomes.

That's what I try and do — push those ones that are on the cusp not to make that mistake; you don’t have to work for somebody. You can take money from them, you can get investors … but you can wake up every morning controlling your own destiny, every day of your life — and that's good enough for a third of the population. If you are in the other two-thirds and want to be a model employee, that’s great. Because being an entrepreneur is 110 percent commitment. There is no balance in life, and that's the dark side of it. You get your freedom later after you have achieved financial success. But you have to decide if you are a gum scraper or you tell people to scrape gum.  

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