Financiers like Kevin O'Leary never sleep, so what better day than Labor Day, September 3, for the money-minded mentor-to-millions to spend some time on Megyn Kelly's NBC morning hour talking employment. It's always fun to see how successful people started out in the work world, and Megyn Kelly was more than willing to show her first entrée into employment, sharing her video clips as a fitness instructor, literally bouncing with energy. She brushed off jabs from Matt Iseman, her favorite sidekick from “American Ninja Warrior," who was singing “Physical” in the background.

Megyn likely keeps in shape more from motherhood and juggling her broadcast assignments than from being the one in front of a class of new fitness devotees now, but she still has fond memories of her first job.

Kevin O'Leary could not share such fond recollections of his first outing as an employee, despite being a portrait of a handsome, fully-coiffed teen of the time. The mega-millionaire, best known for his brutal honesty and purported wisdom in the world of finance and on "Shark Tank," never made it through his first day on the job, and the experience taught him a life-altering lesson.

A step too low

Many teenagers couldn't dream of a better job than being an ice cream scooper at a shop in the mall, and looking back at photos shared of the teenage Montréal native, one would think that Kevin O'Leary could sell plenty of floats, cones, and banana splits.

He had a charming smile in those days and dark, shoulder-length hair that could have landed him on the cover of the Canadian version of Tiger Beat, especially with his perfect bangs.

Actually, there was a special young lady the young Kevin O'Leary's life at the time, and she does figure into the story. Kevin did a fine job with the skill of ice cream scooping.

It was the “fallout” of discarded gum on the floor from customers caused the newly-employed future mogul to reconsider making a living in the way common folk does. His girlfriend worked in a store just across the way, and when his boss told him he had to scrape the wads of gum from the floor, he was embarrassed that his lady love would see him so humiliated on his knees.

Pride came with a cost.

“I'll fire you,” his boss warned if he refused. O'Leary responded with “You can't fire me!” That declaration resulted in a swift “You’re fired,” so the handsome teen was out of the ranks of the employed. Megyn Kelly could not resist bringing up that a certain president has made a career out of saying just those two words.

The lesson lasted

Kevin O'Leary asserts that on that day, he decided that he would never work for anyone again, and instead, become the one who hires, and who lets assets work for him. He playfully teased that “Now I have enough to bulldoze the whole mall,” but retail is not really this Shark’s forte. He prefers royalty deals, and he loves the phrase “in perpetuity” almost as much as he loves saying “You’re dead to me,” to anyone who refuses his offers.

Kevin O'Leary is often honest about his financial rise, and all its bumps, to the top, and has been a frequent guest of Megyn Kelly, like Isemen, who gave up being a doctor to pursue standup comedy, and then Hollywood opportunities. He may have had a considerably more auspicious first job than O’Leary, but his first TV gig as Captain Obvious on a children's show lasted for just one episode.

NOTE TO EDITOR: The CNBC interview link was the most recent I could locate in addition to today's Megyn Kelly source. I searched extensively, and I hope you will allow the piece to be published. Thank you.
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