Kevin O'Leary was fired from his first job over a bizarre reason —and never worked for anyone again

O'Leary spilled that his first stint was at an ice cream parlor as he had a crush on a girl who worked at a store across it.
Kevin O'Leary participates in a panel discussion during the annual Milken Institute Global Conference at The Beverly Hilton Hotel in California. (Image Source: Getty Images | Photo by Michael Kovac)
Kevin O'Leary participates in a panel discussion during the annual Milken Institute Global Conference at The Beverly Hilton Hotel in California. (Image Source: Getty Images | Photo by Michael Kovac)

'Shark Tank' judge Kevin O'Leary once revealed why he got fired from his first job. During a Fox News interview, O'Leary spilled that his first stint was at an ice cream parlor as he had a crush on a girl who worked at a store across it. As per Fandom Wire, O'Leary decided to take the girl out after work but his boss ruined his plans when he asked him to scrape all the gum off the floor. O'Leary penned on Facebook, "The day I got fired from my first job for refusing to scrape gum off the floor was the day I decided I’d rather own the store than clean it. It wasn’t about the gum, it was about understanding my worth and where I saw my future." 



 

O'Leary detailed, "I went there for the very first day and the girl I was hot for in high school was working at the shoe store across the mall and the plan was when I finished scooping, we would go out on a date...So she's watching me and then, at the end, the woman who owns the store comes over to me and says, 'Listen, you have gotta take all of the gum off the tiles'...and I was looking at the girl across the hall looking at me saying, 'That’s not a brand for me.' Getting on my knees and scraping the floor is a bad look. So I said, 'You hired a scooper, not a scraper,' and she said, 'No, no, no. You're gonna do whatever I say I own the store,' and I said, 'I'm not doing it.' She said, 'You're fired' and I never had a job or had been fired before and I did both of them on the same day and that was the last time I ever worked for anybody."



 

O'Leary shared that the experience was humiliating, especially breaking the news to his mother. He argued that he learned that day that there are two types of people— people who scrape gum off the floor and those who own the store, and he wanted to be the latter. He stressed, "I'm not saying that it's bad to be an employee but I don't know how to do it." 



 

The story had 'Shark Tank' fans gushing over O'Leary's boss mentality. On Facebook, a viewer penned, "Wow that gum created the man you see now. If he had scrapped the gum he would probably would still be doing it." Another echoed, "Good on you Kevin. That’s very smart." In a similar vein, one chimed, "The notion of understanding, curating, and protecting your personal brand is critical even if you’re an employee vs entrepreneur. People who don’t understand why they never get promoted may never have considered their brand within the organization. That said, it’s definitely better to own the store."



 

O'Leary a.k.a 'Mr Wonderful' today has a staggering net worth of $400 million, according to Celebrity Net Worth. The Canadian mogul accumulated his early fortune through his educational software company SoftKey Software Products and rose to fame after his appearances on television shows such as 'Dragons Den' and 'Shark Tank.' 

GET THE BIGGEST ENTERTAINMENT STORIES
STRAIGHT TO YOUR INBOX.

MORE STORIES

Mariska Hargitay’s reported ‘SVU’ paycheck includes acting and producing, while her estimated wealth reflects a career spanning more than four decades.
2026-11-12T20:43:49.000Z
'Marshals' Season 2 introduces a Texas cowgirl who joins Kayce Dutton at East Camp to help establish an equine therapy program.
2026-11-12T20:24:16.000Z
‘School Spirits’ Season 4 brings back Jennifer Tilly as Deborah Hunter-Price and Milo Manheim as Wally Clark while expanding its cast with four new additions
2026-11-12T20:05:26.000Z
Paul Wesley and Sara Canning reunite for Netflix’s college sports romance ‘Icebreaker,’ years after starring together in ‘The Vampire Diaries.’
2026-11-12T19:40:49.000Z
Peacock’s ‘The Good Daughter’ finale answers questions about the school shooting, Huck’s past and the buried secrets dividing Sam and Charlie’s family.
2026-11-12T16:29:59.000Z
‘Chicago Fire’ star Taylor Kinney shares the date for the franchise’s next crossover, which will bring all three NBC dramas together
2026-11-12T08:52:55.000Z
James Reynolds reveals his Parkinson’s diagnosis and explains why ‘Days of Our Lives’ is bringing it into Abe Carver’s storyline
2026-11-12T08:23:38.000Z
Charlie Vickers and his ‘The Rings of Power’ co-stars hint at Sauron’s next move and the Season 3 moments that left even the cast struggling for words
2026-11-12T07:50:09.000Z
Nearly three decades after their 1997 horror film, Jennifer Love Hewitt and Ryan Phillippe are sharing the screen again, this time in the ‘9-1-1’ franchise
2026-11-12T06:55:17.000Z
The Hulu spinoff follows nine MomTok creators in California, with Jen Affleck as the lone original star
2026-11-12T05:10:11.000Z