Disclosure: The article was originally published on Benzinga.com on June 19, 2025.
Shark Tank star and investor Kevin O’Leary once remarked on how real-world experience—not business school—shaped his instincts, allowing him to size up entrepreneurs with near-perfect accuracy.
What Happened: In a 2019 episode of Behind the Brand with Bryan Elliott, O’Leary was asked whether entrepreneurs are born or can entrepreneurship be learned? And how does he judge someone, beyond just their business numbers?
In response, O’Leary told a story from when he was finishing his MBA. A guest lecturer came into class and told them bluntly that the real world would be far tougher than they expected.
According to the speaker, a third of the class would fail, another third would stagnate and only a small portion would find real success.
At the time, O’Leary thought the speaker was arrogant and wrong, but now, decades later, after building his career and becoming an investor, he said, “Today, I’m that guy… he was absolutely right.”
O’Leary, who is also known as Mr Wonderful, went on to explain that experience builds something far more valuable than theory: intuition.
“Intuition is just experience distilled,” he stated, adding, “I can sit in a room with somebody for 15 minutes and know if I've got a winner or not and 99% of the time I'm right so I listen to the gut and I listen to the person I listen to the plan I know it's gonna work or it isn't I just know I'm that good.”
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Why It’s Important: According to Celebrity Net Worth, O’Leary currently has a net worth of $400 million.
O’Leary has invested over $8.5 million in 40 companies on the show, with some big wins, but also some painful losses, reported The Street earlier this year.
One of his worst investments cost him $500,000 after he ignored his instincts and backed a telecom startup that quickly burned through the funds.
Despite red flags and an uneasy feeling, O’Leary reinvested because he liked the founder — a decision he now regrets. The experience taught him two key lessons: always trust your gut and avoid founders who refuse to adapt.
He previously highlighted that failure is part of investing, but stubborn entrepreneurs and ignored intuition often lead to the biggest losses.
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Disclaimer: This content was partially produced with the help of Benzinga Neuro and was reviewed and published by Benzinga editors.
