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Kevin O’Leary’s Humiliating Experience at His First Job

Kevin O’Leary looked back on his experience as an Ice-Cream Scooper in a chat with Ben Weiss.

Kevin O’Leary On Shark Tank

Highlights

  • Kevin O’Leary interacted with Ben Weiss and shared his experience from his first job.
  • Kevin claimed that an incident from the job made him the strong business person he is today.
  • The Shark reiterated the importance of standing on one’s ground.

Kevin O’Leary has presented a strong persona on Shark Tank. His clear-cut responses to pitchers, along with interactions with fellow Sharks, showcase his confidence and knowledge. The foundation of this strong personality has been shaped by Kevin’s experience at his first job.

In a 2024 conversation with entrepreneur Ben Weiss, the Shark investor reflected on his first-ever job and explained how it transformed his life. Kevin revealed that when he was in high school in the eleventh grade, he took a job at an ice cream parlor.

The reason why he did so was that he wanted to impress a girl who worked in a shoe store across the parlor. While this detail may appear a bit amusing, the experience brought a positively drastic change in Kevin’s life.

Kevin’s Nightmare As An Ice-Cream Scooper

Giving exact details of his first paying gig, Kevin O’Leary revealed to Ben that his profile was that of an ice-cream scooper. For this, the Shark used to sample ice creams for people with sticks. After trying it, buyers used to throw their gums on the floor, which resulted in a pile of garbage.

At the end of the day, the owner of the parlor told Kevin to scrap the gum off the floor. The Shark, who was then a teenager in an Ottawa based school, felt if he did so, it would not give a good impression to his crush. So, Kevin O’Leary told the owner, ‘You hired me as a scooper, not a scraper.’

Replying to him, the lady said, ‘No, I hired you to do whatever I tell you to do. You’re my employee.’ When Kevin still refused, she removed him from the job.

Kevin’s Takeaway From His First Job

After narrating the entire incident of his first job as an ice-cream scooper, Kevin O’Leary told Ben that he ‘immediately understood how this whole thing works.’ Additionally, the Shark admitted that the experience brought him to a realization that he cannot work under anyone else.

Kevin O’Leary stressed that he is not someone who can allow a person to have such power over him. So, he never went back to getting a job again. Instead, he decided to take up entrepreneurship, which could allow the Shark investor to do things just the way he wanted.

In what could have given him an early work experience, Kevin faced a defining moment in his life in just a day. The incident allowed the Shark to learn about the value of autonomy and control in business. Plus, independence allowed Kevin O’Leary to shape his career graph in an ideal way.

About Rob Merlino

Entrepreneur, auteur, raconteur. Rob Merlino is a blogger and writer who enjoys the Shark Tank TV show and Hot Dogs. A father of five who freelances in a variety of publications, Rob has a stable of websites including Shark Tank Blog, Hot Dog Stories, Rob Merlino.com and more.

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