4 Investments Mark Cuban Regrets Not Cashing In On
Even billionaires have financial regrets, including Mark Cuban, an American businessman, entrepreneur, television personality and former principal owner of the Dallas Mavericks.
For Mark Cuban, some of these investments that he regrets not cashing in on were businesses that initially seemed too expensive, too unusual or outside his expertise. But fast-forward a couple of years, many of these missed opportunities have become major companies today. Here are four investment opportunities Cuban said he regrets passing up.
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Uber
Cuban’s biggest missed opportunity is Uber.
Before Uber became a global ride-sharing giant, cofounder Travis Kalanick approached Cuban about investing $250,000 at a roughly $10 million valuation, according to Fortune. Cuban already knew Kalanick because he had invested in his previous startup, Red Swoosh. However, Cuban turned down the opportunity because he didn't think the ride-share company was worth that much.
“Just think: If I would have given him $250,000 on a $5 million or $10 million valuation, it’d be billions,” Cuban said. Given Uber’s market capitalization of $144.73 billion as of today (per CompaniesMarketCap), Cuban’s $250,000 would be worth about $3.62 billion right now.
Spikeball
Sometimes an idea can sound almost too simple to become a serious business.
Spikeball is a four-player game built around bouncing a yellow ball onto a small round net. Founder Chris Ruder appeared on "Shark Tank" in 2015 with ambitions to build not just a product, but an organized sport.
Cuban, in his role of one of the investor "Sharks," passed on this opportunity as well.
Years later, Cuban has admitted in several interviews, including this one with Kevin Hart, that one of his biggest regrets is not investing in Spikeball, and he gets really jealous when he goes to beaches and sees people playing it.
The Bouqs Company
Online flower company, The Bouqs Co., also failed to win Cuban over when cofounder John Tabis appeared on "Shark Tank" in 2014. The company wanted to simplify the flower industry by shipping flowers more directly from farms to consumers and eliminating the middlemen.
Though all the Sharks on the show, including Cuban, passed on the investment opportunity, Bouqs kept growing. And by 2026, Bouqs has become one of the largest floral subscription businesses in the U.S.
“That’s the one I regret not doing, ‘cause that’s a deal I would’ve loved,” Cuban admitted to ABC News.
Chef Big Shake Foods
Cuban also regretted passing on Chef Big Shake's shrimp sandwiches idea. Chef Shawn Davis, aka Chef Big Shake, pitched his shrimp burgers on "Shark Tank." Cuban later said on Good Morning America that seafood wasn’t an industry he understood well enough to invest in.
“He had these shrimp sandwiches, and one of the things in business [is] you have to try to stick to what you know, and I don’t know shrimp sandwiches from hot dogs,” Cuban told "Good Morning America." After he passed on the opportunity, the business still managed to go from just around $200,000 in annual sales to more than $6 million.
This article was provided by MoneyLion.com for informational purposes only and should not be construed as financial, legal or tax advice.
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