Kevin O'Leary fired off a post on X earlier this month that was part confession, part humblebrag. It started with a cat swab and ended with millions in his pocket. In classic Mr. Wonderful fashion, he admitted he once wrote a $250,000 check—not because he loved the pitch, but because he wanted it to go away.

"A woman pitched me a cat DNA test… for $29," he posted. "I laughed. I told her, ‘I can buy a new cat for five bucks.' But she wouldn't give up. So I wrote a $250K check just to get rid of her."

The woman was Anna Skaya. The company? Basepaws. On the surface, it looked like a gimmick—genetic testing for your cat. But underneath the fluff was a serious play in DNA data collection. And O'Leary? He cashed out hard.

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In the video clip attached to the X post, he explained that when Skaya first appeared on "Shark Tank" in 2019, she pitched her swab-and-send kit to help pet owners learn more about their cat's genetics, health risks, and diet needs. O'Leary mocked the idea. "No one is going to give you a dime. This is a stupid idea," he told her. But her pitch didn't fizzle—it wore him down.

"For $250,000 I can just get her out of here," he joked. So he went in on the deal.

Three years later: "All cash exit. I made a fortune." Or, as he put it more colorfully, "I made a sh*tload of money."

It wasn't the first time O'Leary revisited the pitch that sounded ridiculous but made him millions. On "The Daniel Mac Show" in July 2023, O'Leary recounted the absurdity: "A woman comes on with a Q-tip and says, ‘For $29.95, I can extend your cat's life 20 to 30%.' I said, ‘Wait a minute. I can buy a new cat for two bucks. Why would I spend $29.95?'"

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And yet, he admitted, "It was such a crazy pitch, I bought it anyway. She was so compelling." He estimated he paid around $50,000 for a 3.5% stake. It's worth noting that figure doesn't match the $250,000 for 5% he mentioned on Shark Tank and in his recent X post, leaving it unclear whether the deal terms changed behind the scenes.

"We just sold the company at such a crazy price that I had to sign an NDA," he said. "It went to a very large pharmaceutical company. Far over $50 million."

O'Leary sees 220 pitches a year. This one? His biggest percentage win on "Shark Tank"—even bigger than Plated, the meal-kit company that sold to Albertsons for $300 million.

He's not shy about crediting Skaya. "I invested in Anna for Anna," he said in a separate video. "She's so good at promoting her products. She built that business tenfold since Shark Tank." He'd back her again "in two seconds"—but, as he put it, "she's too rich."

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Now for the numbers. In Q2 of 2022, Markets Insider reported that animal-health giant Zoetis—an $80 billion company—acquired Basepaws. Zoetis disclosed $93 million in cash acquisitions that quarter, and Basepaws was the only company named.

Based on their reported calculations, if Zoetis paid a conservative $50 million, and O'Leary owned 5% from the $250,000 deal — which was the original offer on the show, that's roughly $2.4 million. If his revised claim of $50,000 for 3.5% is accurate, his haul could've been around $1.7 million—a 35x return. And if Zoetis shelled out the full $93 million? His payday likely landed between $3.2 million and $4.5 million.

Not bad for a cat idea he once called stupid.

Apparently, you can buy a cat for two bucks. But investing in the persistent woman who wanted to swab it? That's what really paid off.

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