.kevinolearytv on his worst 'Shark Tank' investment ever: 'I lost half a million dollars.' (via CNBCMakeIt)
The quick loss of O'Leary's initial investment set off alarm bells in his head, he says. But, the startup founder won the investor back by admitting his past mistakes and promising to fix his approach.
O'Leary says he quickly realized his mistake: The company immediately went back to its free-spending ways, burning through the second $250,000 investment within two months without anything to show for it.Had O'Leary instead heeded his own uncertainty, he would have prevented the additional losses. "The lesson is: Listen to your gut, because that is your experience [talking]," he says. "You gain that over time. You can't forecast it. You have to learn it.
To an extent, it might be an unavoidable part of investing. O'Leary says he actually expects the majority of his investments to disappoint. "You make 10 investments, you get two to three huge hits. And it pays for the other seven [failed investments]," he says.
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