Mark Cuban missed out on huge Shark Tank investment despite making $30,000,000 offer that's largest in the show's history

Mark Cuban once made the largest Shark Tank offer in history - and the business that turned him down is apparently now worth a jaw-dropping nine-figure sum.

From 2011 to 2023, Cuban, 66, served as a high-stakes ‘Shark’ investor on Shark Tank US.

During his 14-season run, the Pennsylvanian native poured money into businesses like live horror entertainment producers Ten Thirty-One Productions, nut butter spread Nuts 'N More, BeatBox Beverages and more.

Cuban, whose enviable investment portfolio also includes Magnolia Pictures and the sports tech company Mustard, is also the former principal owner of the Dallas Mavericks.

In January 2000, the father-of-three purchased the majority stake in the NBA team before selling it to the Adelson and Dumont families in late 2023.

This sale meant Cuban was no longer in control of the Mavs, who play the Brooklyn Nets at the Barclays Center tonight (March 24).

And while the reality TV star’s net worth is estimated by Forbes to sit at around $5.7 billion, the 2929 Entertainment co-owner actually missed out on the chance to increase it way back in 2015.

During the sixth season of Shark Tank US, the billionaire and his fellow ‘Shark’ investors met with the Kang Sisters.

Arum, Dawoon and Soo Kang appeared on the TV show looking for $500,000 for 4 percent of their dating and social network service Coffee Meets Bagel.

The San Francisco-based company launched in 2012 and is engineered for singletons with serious dating intentions to meet ‘The One’, eliminating awkward conversations on intentions and time-wasting interactions.

The Kang Sisters were offered a hypothetical $30 million by Mark Cuban (ABC)

During their time on Shark Tank, the Californian siblings unfortunately failed to impress the likes of Barbara Corcoran, Lori Greiner and Cuban with their company.

Some claimed the trio’s annual combined salary of $300,000 was too much, while others said it was ‘too easy’ for the competition to rip off their app model.

After all five admitted they wouldn’t want to invest in Coffee Meets Bagel, Cuban sprang a surprising lifeline.

“Let me ask you a question. If I offered you $30 million for the company, would you take it?” Cuban asked.

With the largest money offer in Shark Tank US history on the plate, the sisters deliberated for a heartbeat.

“No,” they responded. “I would not be taking it because we see this business growing as big as Match.com and do you know how much revenue they’re generating? $800 million a year.

“They’re becoming a billion-dollar revenue company and we think [our] model and this product has potential to be as big as Match.”

Upon hearing the history-making deal had been turned down by the Kangs, Robert Herjavec said: “He offered you $30 million and you didn’t even flinch.”

“She should feel confident,” defended Cuban. “It’s a new, effeminate version of ‘Hot or Not’ which is brilliant. But I don’t know how protectable that is.”

Cuban's offer was eventually turned down by the business trio (ABC)

He added that although he gives the businesswoman ‘total credit’ for their work, investing in Coffee Meets Bagel would be too much of a risk.

The Kangs left Shark Tank US without any investment. A month after their appearance, the company announced a $7.8 million Series A financing round led by DCM Ventures.

And nearly a decade after their appearance, it’s reported that Coffee Meets Bagel is still thriving.

Last year, TechieGamers reported that it’s the second most popular dating app in Singapore, with an estimated user base of around 10 million people.

With 85 employees, Coffee Meets Bagel reportedly makes around $36 million in annual revenue, with the company being estimated at a $150 million value.

With those kinds of figures, maybe Cuban is kicking himself that he didn’t make that $30 million offer seem a little more lucrative, hey?