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Shark Tank's Kevin O'Leary Calls Business 'Biggest Sport On Earth,' Says 'You Don't Retire' From Entrepreneurship

Benzinga·12/30/2025 10:23:49
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Kevin O'Leary, the Shark Tank investor known as “Mr. Wonderful,” compared the pressures of professional sports to entrepreneurship, calling business the ultimate arena for competition.

Pro Athletes Face Intense, Short-Lived Careers, O'Leary Explains

On Monday, O'Leary posted on X discussing the stress and intensity of both careers. 

"People ask me all the time what's more stressful, being a professional athlete or being an entrepreneur. The truth is, they're both brutal, just in different ways," he wrote. 

He explained that athletes face a short career window, often five to seven years if they're lucky, where performance is critical every day and injuries can abruptly end their careers.

Entrepreneurs Compete For Decades

Entrepreneurship, by contrast, lasts for decades. "You don't age out. You don't retire. You do this for decades. Once you get the bug, it never leaves you," O'Leary said. 

He emphasized that his motivation isn't money anymore, but the thrill of competition: "I love to compete. Nothing motivates me more than being told I can't do something. I live for that." 

He also highlighted why many athletes, including Tom Brady and Shaquille O'Neal, transition into business: "They're still competing, just in the biggest sport on earth now… MONEY."

See Also: Bernie Sanders Slams ‘Immoral and Unsustainable' Wealth Inequality, Calls To End Oligarchy Amid Soaring Billionaire Fortunes

O'Leary Reveals Productivity, Growth Tips

O'Leary shared insights into his daily routine and personal growth.

He woke up naturally at 5 a.m., followed global news, went on a 12-mile bike ride, avoided managing thousands of emails, and focused on three key tasks each day, inspired by Steve Jobs.

He also reflected on his career and life experiences, advising his 25-year-old self, "Don't change anything. The good, the bad, the failures, the wins, that's your DNA."

O'Leary emphasized that embracing both successes and mistakes shaped his professional journey and encouraged young professionals to learn from their experiences.

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Disclaimer: This content was partially produced with the help of AI tools and was reviewed and published by Benzinga editors.

Photo courtesy: Kathy Hutchins / Shutterstock.com