"Didn't listen to my gut" — Shark Tank's Kevin O'Leary shares his biggest financial mistake

Kevin O
Shark Tank's Kevin O'Leary Testifies On China's Financial Aggression In Joint Senate & House Hearing | Image via Getty

Even seasoned investors like Kevin O'Leary, who is well-known on Shark Tank for having keen intuition, sometimes have regrets. In a recent video he shared on his Instagram account, O'Leary talked candidly about one of his worst financial mistakes. Thinking back on the expensive choice, he acknowledged that deviating from his gut caused him to enter into a transaction that didn't work out emotionally or financially.

"What was my biggest financial mistake? And I'll tell you what I learned from it. I didn't listen to my gut."

O'Leary, well-known for his calculated risks and tough love style, highlighted the importance of intuition in the economic world. Although data and analysis are important, he revealed that no spreadsheet can ever fully replace the inner voice of experience, something he discovered the hard way. The lesson? It's worthwhile to pause when everything appears fine on paper, but something feels off.


Shark Tank's Kevin O'Leary opens up about the time when he lost $750,000

Even the brightest minds on Shark Tank can hit a block financially, and Kevin O'Leary isn't hesitant to acknowledge this. In a recent reflection, the investor described how he lost an incredible $750,000 on a deal because he ignored his gut. Even more painful than the lost money was the fact that he sensed it coming but decided to ignore his intuition. The narrative of O'Leary serves as a warning about the real consequences of self-doubt.

The clip began with Shark Tank expert Kevin O’Leary opening up about making a $750,000 investment despite his internal self telling him not to. The result was disastrous. All the money was gone.

"I made an investment, $250,000, and it didn't feel right. Then I followed up just a couple of months later with another $500,000, and it went to zero."
"Not listening to my experience, my intuition, and my gut feeling. What is gut feeling? It's experience. Always listen to it, and don't get emotionally involved. I probably let my emotions play into that. I lost $750,000."

Shark Tank OG then reflected upon the importance of following one's instincts, describing them as a result of experience. He acknowledges that letting emotions influence his decisions and disregarding his instincts was his worst mistake.

He wrapped up with a piece of straightforward advice: take a step back and pay attention to your inner guidance when emotions begin to affect judgments. It frequently understands what the facts cannot.

For both seasoned investors and aspiring business owners, this unique moment of vulnerability serves as a potent reminder that gut feeling is more than just a catchphrase. It frequently makes the difference between costly regret and success. Even in the presence of specialists, O'Leary's candor serves as a reminder to follow your own instincts.


To watch Kevin O'Leary make some of the best investments of his life, watch Shark Tank on ABC.

Edited by Anshika Jain