Like many teenagers, Kevin O'Leary got one of his first paying gigs working in a mall.
But it wasn't just any job. The brief stint as an ice cream scooper changed O'Leary's life. The "Shark Tank" investor says the day his boss fired him was the moment he realized he wanted to be an entrepreneur.
As a high-school student in Ottawa, Canada, O'Leary took a job at Magoo's Ice Cream Parlour at a mall where girls from his class would hang out. It wasn't a cool job by any means, but he hoped it could get him a chance to work his magic.
The first day went by easily enough, but the next day didn't end so smoothly.
"It was the end of the day of my second day of work, and the woman who owned the ice cream parlor said to me, 'Listen, before you go, scrape all the gum up between the tiles,'" O'Leary tells Business Insider.
He saw two problems with that:
1. It was a Mexican tile floor, the kind that would require some tough maneuvering on his hands and knees.
2. He'd have to do that in front of the cute girl who worked at the shoe store across from him, risking humiliation among her and her friends.
"I said, 'No, I'm not going to do that. You hired me to be an ice cream scooper,'" O'Leary recalls. "She said, 'I hired you for whatever I want. You work for me. Scrape the gum or you're fired.' And I said, 'I'm not doing it,' and so she fired me."
He says he didn't really understand the full weight of what it meant to be fired. He was shocked and embarrassed.
"I realized then that when you work for somebody else, you're basically their slave," he says. "From that day on I swore I'd never work for anyone else. That was the beginning of my journey."
O'Leary writes on LinkedIn that he got home with "tears of hot rage stinging my cheeks." He told his stepfather that he'd never work for anyone again, to which his stepdad replied, "Even if you're self-employed, you'll be serving someone," explaining that business owners have obligations to their customers and shareholders.
O'Leary writes that his stepfather's lesson became clear years later, but he was convinced that he would one day become an entrepreneur.
He went back to the mall in 2009 to see if his old boss was still around. He wanted to thank her.
"I never did find her — and when I visited the mall I realized I could buy it today if I wanted and bulldoze it — but she was a very important part of my decision-making for the rest of life," he tells us.
"That's how it started. I'll never forget it."
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