Despite being meticulous about the businesses he backs on “Shark Tank,” Kevin O’Leary admits that he’s not particularly optimistic about most of them. Speaking with CNBC, he shared that only a small percentage of his deals actually manage to make him money. “You make 10 investments, you get two to three huge hits. And it pays for the other seven,” he said. But what he didn’t expect was to incur a colossal loss on one of his deals, and it’s something he regrets to this day.
“You put $250,000 on a deal. And then the guy calls you up four months later saying, ‘Look, I burned through all the cash. But, I know what I did wrong. I need another [$250,000],'” O’Leary recalled, refusing to name-drop the company due to legal issues. And even though he initially wanted to refuse, he went ahead and bit the bullet as the founder showed promise. “My gut said ‘No,'” he continued. “But because I knew the guy and I liked him, and he was a friend … I gave him another.”
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O’Leary says that he’s still “pissed” about it, but knows that losing is part and parcel of investing. “What I’ve learned after doing this a long time [is] no matter how you feel, and how optimistic you are, in the moment of making an investment, pulling the trigger, you have no idea of the outcome. You have zero probability,” he noted. “Anybody that says they do is full of s***.”
