Kevin O'Leary on his worst 'Shark Tank' investment ever: ‘I lost half a million dollars' - CNBC | Canada News Media
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Kevin O'Leary on his worst 'Shark Tank' investment ever: ‘I lost half a million dollars' – CNBC

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If there’s one thing Kevin O’Leary has learned from more than three decades as an investor, it’s that not every bet pays off.

On ABC’s “Shark Tank,” O’Leary has invested more than $8.5 million in roughly 40 companies since the show debuted in 2009, according to an estimate from Sharkalytics. The longtime investor and chairman of O’Shares ETFs has some notable successes, like an investment in online meal kit service Plated that later sold for $300 million.

He’s also seen his fair share of disappointing deals. “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,” O’Leary tells CNBC Make It. “You have zero probability.”

“Anybody that says they do is full of s—,” he adds.

O’Leary says he’s learned the hard way to trust his gut when it comes to making deals. While he declined to reveal the name of the company that represents his worst “Shark Tank” investment, citing ongoing litigation, he says it was a startup in the telecommunications industry — and that he ultimately lost $500,000 on the deal.

“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 says, describing the fateful investment.

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.

“In my stomach, I didn’t feel right about it,” O’Leary says. “My gut said ‘No.’ But because I knew the guy and I liked him, and he was a friend, and yada, yada, yada … I gave him another [$250,000].”

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.

“He went to zero 60 days later. So I lost half a million dollars,” O’Leary says.

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.”

The investor says his money-losing deals typically have a common thread: startup founders who can’t “pivot.”

“They can’t get out of their own way,” he says. “They won’t listen to anybody else.”

O’Leary calls those entrepreneurs “stupid,” because their stubbornness prevents them from changing their bad habits and tactics: “They don’t understand [that] the world moves and you have to move with 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.

Still, his worst-ever “Shark Tank” investment bothers him to this day because he didn’t trust his gut.

“I ignored it, and it cost me half a million bucks,” O’Leary says. “That was really stupid. I’m pissed. And I don’t forget that.”

Disclosure: CNBC owns the exclusive off-network cable rights to “Shark Tank.”

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S&P/TSX gains almost 100 points, U.S. markets also higher ahead of rate decision

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TORONTO – Strength in the base metal and technology sectors helped Canada’s main stock index gain almost 100 points on Friday, while U.S. stock markets climbed to their best week of the year.

“It’s been almost a complete opposite or retracement of what we saw last week,” said Philip Petursson, chief investment strategist at IG Wealth Management.

In New York, the Dow Jones industrial average was up 297.01 points at 41,393.78. The S&P 500 index was up 30.26 points at 5,626.02, while the Nasdaq composite was up 114.30 points at 17,683.98.

The S&P/TSX composite index closed up 93.51 points at 23,568.65.

While last week saw a “healthy” pullback on weaker economic data, this week investors appeared to be buying the dip and hoping the central bank “comes to the rescue,” said Petursson.

Next week, the U.S. Federal Reserve is widely expected to cut its key interest rate for the first time in several years after it significantly hiked it to fight inflation.

But the magnitude of that first cut has been the subject of debate, and the market appears split on whether the cut will be a quarter of a percentage point or a larger half-point reduction.

Petursson thinks it’s clear the smaller cut is coming. Economic data recently hasn’t been great, but it hasn’t been that bad either, he said — and inflation may have come down significantly, but it’s not defeated just yet.

“I think they’re going to be very steady,” he said, with one small cut at each of their three decisions scheduled for the rest of 2024, and more into 2025.

“I don’t think there’s a sense of urgency on the part of the Fed that they have to do something immediately.

A larger cut could also send the wrong message to the markets, added Petursson: that the Fed made a mistake in waiting this long to cut, or that it’s seeing concerning signs in the economy.

It would also be “counter to what they’ve signaled,” he said.

More important than the cut — other than the new tone it sets — will be what Fed chair Jerome Powell has to say, according to Petursson.

“That’s going to be more important than the size of the cut itself,” he said.

In Canada, where the central bank has already cut three times, Petursson expects two more before the year is through.

“Here, the labour situation is worse than what we see in the United States,” he said.

The Canadian dollar traded for 73.61 cents US compared with 73.58 cents US on Thursday.

The October crude oil contract was down 32 cents at US$68.65 per barrel and the October natural gas contract was down five cents at US$2.31 per mmBTU.

The December gold contract was up US$30.10 at US$2,610.70 an ounce and the December copper contract was up four cents US$4.24 a pound.

— With files from The Associated Press

This report by The Canadian Press was first published Sept. 13, 2024.

Companies in this story: (TSX:GSPTSE, TSX:CADUSD)

The Canadian Press. All rights reserved.

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Economy

S&P/TSX composite down more than 200 points, U.S. stock markets also fall

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TORONTO – Canada’s main stock index was down more than 200 points in late-morning trading, weighed down by losses in the technology, base metal and energy sectors, while U.S. stock markets also fell.

The S&P/TSX composite index was down 239.24 points at 22,749.04.

In New York, the Dow Jones industrial average was down 312.36 points at 40,443.39. The S&P 500 index was down 80.94 points at 5,422.47, while the Nasdaq composite was down 380.17 points at 16,747.49.

The Canadian dollar traded for 73.80 cents US compared with 74.00 cents US on Thursday.

The October crude oil contract was down US$1.07 at US$68.08 per barrel and the October natural gas contract was up less than a penny at US$2.26 per mmBTU.

The December gold contract was down US$2.10 at US$2,541.00 an ounce and the December copper contract was down four cents at US$4.10 a pound.

This report by The Canadian Press was first published Sept. 6, 2024.

Companies in this story: (TSX:GSPTSE, TSX:CADUSD)

The Canadian Press. All rights reserved.

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S&P/TSX composite up more than 150 points, U.S. stock markets also higher

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TORONTO – Canada’s main stock index was up more than 150 points in late-morning trading, helped by strength in technology, financial and energy stocks, while U.S. stock markets also pushed higher.

The S&P/TSX composite index was up 171.41 points at 23,298.39.

In New York, the Dow Jones industrial average was up 278.37 points at 41,369.79. The S&P 500 index was up 38.17 points at 5,630.35, while the Nasdaq composite was up 177.15 points at 17,733.18.

The Canadian dollar traded for 74.19 cents US compared with 74.23 cents US on Wednesday.

The October crude oil contract was up US$1.75 at US$76.27 per barrel and the October natural gas contract was up less than a penny at US$2.10 per mmBTU.

The December gold contract was up US$18.70 at US$2,556.50 an ounce and the December copper contract was down less than a penny at US$4.22 a pound.

This report by The Canadian Press was first published Aug. 29, 2024.

Companies in this story: (TSX:GSPTSE, TSX:CADUSD)

The Canadian Press. All rights reserved.

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