'Shark Tank' investor Kevin O'Leary reveals his 'key to success' — a simple life skill that most ignore

It’s no secret that Kevin O’Leary is one of the most successful celebrity investors in the world today. He might be famous today because of “Shark Tank” but Mr. Wonderful’s success story started long before the show. Like most people, the 70-year-old has gone through his fair share of struggles, and he has learned some valuable lessons from them. One of those is the art of keeping your mouth shut and listening to what the other person has to say as per Showbiz Cheatsheet.

It sounds simple but many people have trouble with listening to and understanding what others have to offer. Being an investor, listening is perhaps the most important skill O’Leary has had to master over the years and he doesn't use it only on “Shark Tank” since entrepreneurs pitch their ideas to him outside the show as well.

But after listening and processing things, it is ultimately O'Leary himself who has to decide the best course of action when it comes to investments based on his sharp business acumen. In an Instagram post, Mr. Wonderful recently uploaded a screenshot of one of his tweets that reads, “The key to success that I would’ve taught myself 20 years ago - shut up and listen.”

That is the same as what he had said in an earlier interview with CNBC Make It as well. “Listen to the people around you. Listen to your boss. Listen to your peers. Shut up and listen,” the veteran investor had advised. “Listening to people and understanding what you’re doing, why you’re doing it, and what the rules are gives you tremendous power,” he added. He also revealed that he had witnessed the power of listening after observing the CEO of one of the companies that he had invested him.

While listening truly is an important skill, it’s not just other people you need to listen to. Sometimes, you need to listen to your gut feeling and stick with it, and O’Leary found that out the hard way. The celebrity investor was impressed with an entrepreneur on “Shark Tank” and decided to invest $250,000 in their company. Only four months later, the same investor called him back and asked for the same amount of money again.

Turns out that he had burned through the first $250,000 and needed more to keep his business afloat. At this point, one would think the investor probably turned down the request, but that was not the case for O'Leary. The entrepreneur said that they had learned from their mistakes and would not repeat them and this was enough to sway Mr. Wonderful.

He once again lent $250,000 to the entrepreneur, but this was a mistake since it only took a couple of months for them to burn through that cash as well. “The lesson is: Listen to your gut because that is your experience. You gain that over time. You can’t forecast it. You have to learn it,” O’Leary said. "So I lost half a million dollars.”