Although Kevin O’Leary started his first business at 32, he knew as a teenager that he would become an entrepreneur.
He had that ‘aha’ moment working at an ice cream shop in high school, he tells CNBC Make It.
“My big ‘aha’ moment was getting fired from my first job on the first day I was there,” O’Leary, now 66, says. “That was really powerful.”
O’Leary got the job at Magoo’s Ice Cream Parlour “because it was located in the mall where the girls tended to gather after school,” O’Leary, who grew up in Canada, wrote in a 2014 LinkedIn post. “Working there was a surefire way to meet girls.”
Kevin O’Leary as a teenager
Kevin O’Leary
But when his manager instructed him to scrape gum off of the shop’s floor tiles, things went downhill.
“The woman there told me, ‘You got to clean all the gum off the floor before you leave.’ And I said, ‘Hey, I’m not a scraper. I’m a scooper. You hired me as [an ice cream] scooper. I don’t want to scrape the floors.’
“She said, ‘How about this? You’re fired,'” he says.
But for O’Leary, being fired wasn’t a bad thing. O’Leary says it made him realize that there are people who own the store and people who work in the store, and “you have to decide which one that you are. And I would prefer to own the store.”
That’s not to say being an employee is a bad thing. “It’s a very secure job if you’re a good employee,” says O’Leary. “Nothing wrong with that. But it’s not for me.”
“I’ve told that story countless times,” he says. “It was my ‘aha’ defining moment. I realized I don’t want anybody to tell me what to do, and the only way I could do that is work for myself. It’s that simple.”
O’Leary’s “Shark Tank” co-star Mark Cuban, also realized after being fired that he would make a better entrepreneur than employee.
After graduation from Indiana University in 1981, Cuban said on “Shark Tank” that he “quit or [was] fired from three straight jobs, including a sales gig at a software retail store called Your Business Software.
“I got fired because [my boss] wanted me to open up the store. It was a software retail store — I had to sweep the floor, make sure the windows were clean, make sure the store was open on time — and I had a big deal I wanted to close. And I thought, ‘Okay, I’m gonna let [my boss] know that I’ve got everything taken care of, someone’s watching my shift if you will, and I’m gonna go pick up a $10,000 check.’
“I figured when I came back he’d be thrilled to death, right? Fired me on the spot,” Cuban said on The Thrive Global Podcast in 2017.
But ”being fired from that job was the determining factor in my business life,” Cuban wrote in a 2013 Forbes piece. “I decided then and there to start my own company.”
“You have to make that decision too,” says O’Leary. “[It’s] a different path. In some ways, it’s much harder. [But] personal freedom is worth it.”
Disclosure: CNBC owns the exclusive off-network cable rights to “Shark Tank.”
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