"I was so humiliated" — When Shark Tank mentor Kevin O'Leary opened up about his first job as an ice cream scooper

In a conversation on the Behind the Brand podcast with Bryan Elliott, posted on March 7, 2019, Kevin O'Leary described his first job during high school. He shared how he worked as an ice cream scooper in a mall and encountered a situation that became a defining moment in his life.

Reflecting on his first day, O'Leary remarked that it was a pivotal moment in realizing the importance of control over his career.

“I was so humiliated when I got home and explained that to my mother,” he admitted, as the event shaped his decision to never work for someone else again.

On his first day, he followed instructions to offer free samples to customers using wooden spoons, which led to discarded gum piling up on the floor. At the end of the day, his boss handed him a scraper and ordered him to clean up the gum.

O'Leary refused, asserting that his role was that of a scooper, not a scraper. His boss insisted that as an employee, he was required to do whatever she asked, and after standing his ground, he was fired.

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Kevin O'Leary on lessons from global experiences

During the podcast, Kevin O'Leary reflected on his global upbringing and how it shaped his perspective. As the son of Irish and Lebanese immigrants, he experienced significant challenges early in life, including dyslexia, which made school particularly difficult.

He credited his mother’s determination to enroll him in experimental programs that taught him to view dyslexia as a unique ability, not a limitation. O'Leary shared that this reframing boosted his confidence and helped him excel later in life.

"Luckily I was very fortunate my mother was desperate she was trying to find a solution for this," he said.

O’Leary’s global exposure was another key influence. Moving frequently due to his stepfather’s career with the United Nations, he lived in diverse countries, including Cyprus, Cambodia, and Ethiopia.

He emphasized the importance of respecting local cultures, recalling how integrating with local communities instead of staying within different circles broadened his understanding of the world.

O'Leary highlighted how his childhood exposure to various economies helped him recognize opportunities in industries like real estate and banking early in his career.

“You don’t know it at the time,” he noted, “but those moments build a foundation for how you see and seize opportunities later.”

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Kevin O'Leary perspective on failure and the pursuit of freedom

Kevin O'Leary also shared his perspective on failure and its role in entrepreneurship. He explained how the fear of failure served as a powerful motivator in his early days.

Recalling one of his ventures that involved a partnership with a major telecommunications company, he detailed how the project failed despite significant investment.

This loss taught him to be more strategic in building partnerships and managing risks.

“Failure is part of the process,” he said. “You learn more from your losses than your wins.”

One of O’Leary’s messages was about the pursuit of freedom as the ultimate goal of entrepreneurship. He described how the lesson from his ice cream job reinforced this belief.

"I realized I never wanted to scrape gum off the floor or be told what to do again. Entrepreneurship gave me the freedom to control my life,” he shared.

Kevin O'Leary said that wealth was not the primary motivation but rather the ability to make independent decisions and spend time on meaningful pursuits.

He advised aspiring entrepreneurs to embrace challenges and setbacks as opportunities for growth.

“The market doesn’t care about your feelings. It’s binary—you make money, or you don’t,” he stated.

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