Kevin O’Leary has a message for anyone managing money for the rich: keep it boring and protect their wealth.
The investor and “Shark Tank” star took to X recently to criticize how many successful entrepreneurs handle their money once they make it big. In his words, “Most wealthy entrepreneurs are terrible investors. They take wild risks, chasing gains like gamblers.”
‘Your Job Is to Protect Their Wealth’
In a video he shared in the same post, O’Leary doubled down on the point. He explained that just because someone built a thriving business doesn't mean they know how to invest. “They have no idea what they’re doing,” he said.
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O’Leary argued that if you’re advising wealthy clients, you shouldn’t try to outperform the market. “Your job is not to beat the market. Your job is to protect their wealth,” he said. “I would tell my clients, I’m not going to beat the market ever. You’re going to be rich forever with me. I’m going to protect your money. I’m going to make sure you get your distribution out.”
He added that he doesn't mess around with high-risk trades or flashy strategies. “I love boring. I just love boring,” he said. Instead of trying to impress clients with aggressive stock picks, he believes in building a portfolio that “will probably track but be less volatile.”
Avoid The Cousin's Restaurant
One of the biggest traps for new millionaires, according to O’Leary, is saying yes to emotional investments. “The first thing they do is they give money to their cousin to open a restaurant or a bowling alley,” he said. “Your job is to say, ‘No, you can’t do that.'”
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He emphasized that the entire point of investing for the wealthy should be preserving their capital, especially for those with $5 million or more. “All the crap that I see in the markets, all the garbage and the leverage and all that stuff, I don’t touch any of that,” he said.
O’Leary knows risk firsthand from his portfolio of 54 “Shark Tank” companies. “A lot of that stuff goes to zero,” he said. “So, I know how to lose money the old-fashioned way. But the real dough, it’s parked in that philosophy we talked about.”
In short, O’Leary wants rich entrepreneurs to stop acting like high-stakes gamblers with their investments. His advice? Keep it simple, stay disciplined, and remember that making money and keeping it are two very different skills.
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