The Worst Shark Tank Deal That Mark Cuban Says He Ever Made

"Shark Tank" judge Mark Cuban has been an integral part of the show's panel since its second season. While he may be one of the most pensive investors, there's more to his silence than meets the eye. In fact, the businessman revealed that it was part of his strategy to listen more than speak when he was on the show. He talked to Chris Voss on Fireside Chat and shared why he allows his co-hosts to first discuss and question the entrepreneur before he engages. He said (via CNBC Make It), "[Silence] gives you a chance to learn. There will be times when someone walks in on 'Shark Tank' and I'm thinking to myself: 'There's no way I'm interested. Or, if I am, I don't have quite all the data that I need to make a decision.'" He continued, "When I listen to the other sharks, they're going to tell me if I have any competition financially to do a deal. They're going to teach me things, potentially, about that industry ... about the person."

When it comes to money, Cuban can flex, be silent, or yell his thoughts from the rooftops. In fact, as far as "Shark Tank" judges' net worth goes, Cuban is the wealthiest investor by far. With a fortune of $4.3 billion, Cuban knows how to stack his loot in deep pockets. However, Cuban may have lost a lot of money on one deal that he bought into on the show. 

Billionaire investor Mark Cuban appeared on the "Full Send" podcast and talked about the worst investment he had made on "Shark Tank." He believed Charles Michael Yim's Breathometer fits the bill. In the 2013 episode,  Yim revealed a smartphone attachment that he dubbed the "world's first smartphone breathalyzer." After an impressive spiel, Cuban was the first investor to make Yim an offer of $500,000 for a stake of 20% of Yim's product. And for only the third time in "Shark Tank" history, all the judges jointly invested in a product. It was a big mistake — at least, according to Cuban. 

He shared that even though the Breathometer was a good product, working with Yim was a challenge. Cuban revealed, "But, the guy — Charles — I'd look at his Instagram and he'd be in Bora Bora ... Two weeks later, he'd been in [Las] Vegas partying, and then he'd be on Necker Island with Richard Branson." Cuban continued, "I'd text him, like 'What the f*** are you doing? You're supposed to be working.'" Yim's response was that he was networking. After settling a claim with a Federal Trade Commission in 2017 for misleading consumers, the company had to refund every customer that had bought a Breathometer, and the investors lost a lot of money. In 2016, Yim told "Next Shark" that he's no longer motivated by money. "I've achieved enough personal wealth that it's not about ambition anymore," he said.

Mark Cuban has a surprising reason he is part of the panel on "Shark Tank." The television personality spoke to Masters of Scale about why he keeps coming back to the show.  He said that during "Shark Tank"'s third year, it became incredibly popular for families to watch the show together. "And so once I understood that, then doing the show became a no-brainer and that's why I continue to do it to this day. It's not because I get access to these great deals, even though some are good, some are bad, but just the idea that kids are watching, or parents are telling me, you know, 'Now my kids understand what I do when I explain that I'm in this industry or that industry.'"

Cuban also shared why one of his favorite "Shark Tank" entrepreneurs is "Simple Sugars" founder Lani Lazzari. He spoke to the Oxford Union Society in 2017, saying (via CNBC Make It), "When I invested, she was 19. When she was 11, she had eczema and wanted to come up with a natural-based scrub to help with her eczema." While another investor may have been discouraged by her youth, Cuban admired her tenacity. "Lani is my favorite entrepreneur because she's so driven and she wants to keep an edge," he stated. As a father of three, Cuban seems to be looking out for other kids just starting out too.