Even multi-billionaires feel bad about missing up on investment possibilities that ended up being really lucrative.
Mark Cuban laments not having made an investment in Uber. In 2009, co-founder of Uber Travis Kalanick offered him the option to invest at a $10 million value, but he declined because he believed the ridesharing company wasn't worth that much, he claimed on a recent edition of comedian Kevin Hart's Peacock talk program "Hart to Heart."
Just consider: If I had given him $250,000 at a [$10 million] valuation, it would have been billions, remarked Cuban.
In particular, Cuban's $250,000 would be worth $2.25 billion today given Uber's market valuation of $90.1 billion as of Friday. "I mean, I did alright. But nevertheless," remarked Cuban, whose current estimated net worth is $5.1 billion.
At the time, Kalanick and Cuban already had a relationship: in 2005, Cuban invested $1.7 million in Kalanick's prior business, a peer-to-peer networking startup called Red Swoosh. "We made a little bit of money," Cuban remarked when Kalanick sold the venture to cloud services provider Akamai in 2007 for $18.7 million.
In particular, Cuban's $250,000 would be worth $2.25 billion today given Uber's market valuation of $90.1 billion as of Friday. "I mean, I did alright. But nevertheless," remarked Cuban, whose current estimated net worth is $5.1 billion.
At the time, Kalanick and Cuban already had a relationship: in 2005, Cuban invested $1.7 million in Kalanick's prior business, a peer-to-peer networking startup called Red Swoosh. "We made a little bit of money," Cuban remarked when Kalanick sold the venture to cloud services provider Akamai in 2007 for $18.7 million.
It turns out that Cuban and Hart both had the experience of declining an Uber. Hart bemoaned his own error of not making an early investment of at least $75,000 in Uber, which he claimed could have made him "$100-plus million," had he seized the opportunity.
Troy Carter, a music manager and Uber investor, reportedly sought to persuade comedian Kevin Hart to invest in the business before it gained widespread recognition. Hart claimed Carter's description of the business as "basically, like strangers giving people they don't know rides" made him think, "This has to be the stupidest s-t I've ever heard."
According to Cuban, he did give Kalanick some guidance on how to deal with some of the substantial regulatory challenges Uber would likely have as well as "dealing with all of the taxicab commissions that are going to try to put you out of business."
For many years, Cuban has regretted not making an investment in Uber. The entrepreneur was insistent at SXSW 2017 that he doesn't want to make the same mistake with any other disruptive business ideas that he did with Uber.