The Next Big Breakout Isn't a Chip. It's Glass.

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Kevin O'Leary Says 'You'll Never Be Free' If You Remain An Employee, But There's Actually Nothing Wrong With It: Here's Why

Shomik Sen Bhattacharjee
July 06, 2025

Shark Tank investor Kevin O'Leary says most people will never start a company, insisting that only about one in three has the grit to thrive as an entrepreneur and taste true freedom.

What Happened: "In life, only a third of people can become successful entrepreneurs. That's it," the investor told Steven Bartlett on the "Diary of a CEO" podcast. "The rest can be very successful employees … you can have a fantastic life.”

“You won't be shackled to the ups and downs of entrepreneurship, the challenge of it, how hard it is. But you'll never be free,” said O Leary.

For the two-thirds who prefer salaried positions, O'Leary insisted there is "nothing wrong" with a corporate path and a steady paycheck.

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He argued that true builders master a razor-sharp "signal-to-noise ratio." Steve Jobs was “80 signal, 20 noise," O'Leary said, mentioning that he sees a similar trait in Tesla Inc. (NASDAQ:TSLA) chief Elon Musk. "Elon Musk … he has no noise. 60 seconds of every minute, 60 minutes of every hour, the 18 hours he's awake, it's all signal. And look what he's achieved,” he added.

Why It Matters: O'Leary, now 70, built Toronto-based SoftKey into an educational-software powerhouse and sold it to Mattel for $3.7 billion in 1999, a deal that helped give him an estimated $400 million fortune.

He told listeners that even at Harvard Business School, two-thirds of students "want to become consultants and lead a life of mediocrity," while the top third embraces “the stress and the pain and the trauma and the anxiety and the risk of failure” of starting companies.

Other successful entrepreneurs identify different ingredients for success, and O'Leary's former "Shark Tank" cohost Mark Cuban echoes them, saying he observes one trait in successful people and that’s a strong work ethic.

Photo courtesy: Kathy Hutchins / Shutterstock.com

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