“Shark Tank” star Kevin O’Leary shared the biggest lesson learned during his investment “journey” with LinkedIn viewers on Monday, urging them to take risks and rely on a little luck.
The O’Leary Ventures chair posted a video to the platform, reflecting on his hits and misses since selling his first company – The Learning Company (originally SoftKey) – to Mattel for $4.2 billion in 1999.
“If you’re going to have a portfolio, if you’re going to be an investor like I am, you need a lot of companies because the ones you think are going to be your best winners never are,” he said, imparting some wisdom to his followers.
“And the ones that you think are going to be dogs – maybe you’re taking a huge risk – they end up being fantastic successes, and the path that this occurs on is serendipitous,” he continued.
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“Markets change, economics change, products change – and the outcome of that is never known until you get to the end of the road.”
O’Leary recounted losing millions in some instances and earning millions in others since striking the Mattel deal, with the caption reiterating the lesson he learned in the process: “You need a little luck.”
“The companies you expect to win often don’t, and the ones you bet against? Sometimes they surprise you. It’s all part of the journey,” the post continued.
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Many in the comments section appeared to agree.
“Kevin, your journey is a testament to the unpredictable nature of entrepreneurship. It’s fascinating how the unexpected can often lead to the biggest wins,” one said.
Another wrote in part, “Your story is a testament to the unpredictable nature of success—luck may tip the scales, but resilience keeps us in the game. Here’s to the surprises that make this journey unforgettable.”
“In the end, it’s about how much you keep getting up and learning from a loss. It sounds like you have taken a few bumps and bruises along the way and are still here,” said a third.
O’Leary also appeared on the FOX Business Network on Monday, where he revisited his criticisms of Vice President Harris for not disclosing her policy positions in detail and for allegedly dodging pressing interviews.
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“The reality is for most of us… as investors [is] we have to deal with whoever is in the White House on November 6. So we’re really hungry for policy, and it looks like we might be getting some,” he told “The Big Money Show.”
“So far, the Harris narrative regarding any distinct policy has been all sugar, no protein, and it’s worked. We’ve got the tightest race in recent times again, and all we care about are these counties in the seven battleground states, but these people want answers, and I think for all of us, no more sugar, please.”
Harris has faced ongoing criticism for her reluctance to disclose specific policy plans or sit down for interviews with tough questions since taking the reins as the Democratic Party nominee.
Commenting on this, O’Leary encouraged her to explain proposals like her floated price control plan, and proposed ideas to give a $25,000 down payment to first-time homebuyers and hike the corporate tax rate to 28%.
“Explain that to me. I know how to ask those questions. I’ll do the interview. I’m happy to do it, and I know what the answers have to be in order to convince me,” he said.
“And I’m just one investor. I understand why she’s reaching out to giant corporate leaders. Some of them are endorsing her. Others are hedging their bets, as in the case of Jamie Dimon, because he’s a pragmatic guy like I am, and I have to deal with her if she ends up being president, but none of the policies I’ve heard yet are going to be pro-GDP growth.”
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