Mark Cuban rejected an offer to make a $250,000 investment in Uber that’d now be worth $2.3 billion

Mark Cuban (Credit: Quinn Harris—Getty Images)

Billionaire Mark Cuban had what he thought were good reasons for not investing in Uber in 2009. But nearly 15 years later, he still deeply regrets not doing so.

In 2009, Uber cofounder Travis Kalanick approached Cuban about making an investment in Uber at a valuation of $10 million. The ride-sharing giant’s market capitalization now stands at about $90 billion.