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'Shark Tank' judge Mark Cuban seals the deal with contestant only to save him from Kevin O'Leary

Cuban had seen enough of Mr. Wonderful's greedy tactics, and he decided to take a stand.
PUBLISHED OCT 23, 2025
Screenshots showing Kevin O'Leary and Mark Cuban on "Shark Tank" (Cover Image Source: YouTube | Shark Tank Global)
Screenshots showing Kevin O'Leary and Mark Cuban on "Shark Tank" (Cover Image Source: YouTube | Shark Tank Global)

Kevin O’Leary is one of the most brutal judges on "Shark Tank," but sometimes, his tough tactics can backfire. It happened once when Mr. Wonderful made a ridiculous offer, which may have resulted in the entrepreneur losing ownership of his company down the line. Thankfully for him, Mark Cuban came swiftly to his rescue and sealed a deal after he said that he was out.

The entrepreneur was a man named Alexander Simone who sought $100,000 for a 5% stake in his company, Prontobev. The product was a wine cooler. It looked like an elaborate flask with two openings. The wine is poured into it through one and poured back out into the bottle from the other.

Screenshot showing the entrepreneur. (Image credit: YouTube | Shark Tank Global)
Screenshot showing the entrepreneur. (Image credit: YouTube | Shark Tank Global)

The entrepreneur said that the inside of the Prontobev was lined with a cooling gel, which brought the temperature down of the beverage by 20 degrees. However, that cooling doesn’t last until the point of freezing. A screen on the bottom of the item shows the temperature of the beverage inside.

Different types of alcohol have different temperatures at which they can be enjoyed best. Wine is no different, and no one knows more about wine on the show than O’Leary. He was the one who walked up to check the results and was impressed. He drank white wine and said that it was at the perfect temperature for consumption.

Screenshot showing the product. (Image credit: YouTube | Shark Tank Global)
Screenshot showing the product. (Image credit: YouTube | Shark Tank Global)

However, the guest had brought a prototype, meaning that the product was not in production just yet. Simone had only earned $54,000 in sales from a crowdfunding drive until that point. Therefore, a $2 million valuation left the sharks surprised. Daymond John, Lori Grenier, Mark Cuban, and Robert Herjavec all said no as a result. O’Leary was the only one who offered a deal, but he wanted a whopping 50% of the company for $100,000.

This was a greedy offer, and everyone knew it. Mr. Wonderful refused to be flexible despite multiple requests from the entrepreneur and the sharks. Ultimately, Cuban had to step in. He first asked his colleague to give Simone at least $200,000 for that much equity. Mr. Wonderful said that he might put more money in the future. “But now he owns less than 50%, it’s not his company anymore,” Cuban clapped back.

Screenshot showing the sharks. (Image credit: YouTube | Shark Tank Global)
Screenshot showing the sharks. (Image credit: YouTube | Shark Tank Global)

“Cry me a river, Mark,” came the response. After this, Cuban made a much better offer even though he had pulled out earlier. He’d pay $100,000 for 25% contingent on the fact that Simone raised another $100,000. The entrepreneur immediately said yes, and O’Leary was left stunned and disappointed.

More on Market Realist:

'Shark Tank' contestant fits cameras inside bird houses — judges weren't convinced by it at all

'Shark Tank' contestants hide inside giant cake to surprise judges — the deal went as expected

'Shark Tank' contestant comes to the show in his boxers and it went as expected

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