Kalanick, 43, a director at the ride-hailing company, sold 20.3 million shares worth about $547 million that were held in a trust, according to a regulatory filing on Friday.
The trades came after a 180-day lockup period restricting insider and early investor sales following May’s initial public offering. They were among the large stake disposals last week that pushed the stock down to an all-time low.
Uber has underwhelmed investors in the public markets so far. Its shares fell 2.2 per cent to $26.42 at 10:22 a.m. in New York, and have tumbled 41 per cent since the IPO. That’s reduced the San Francisco-based firm’s value from almost $76 billion at its listing to about $45 billion.
Kalanick remains one of tech’s richest entrepreneurs. Even after the sale, he still owns 78 million shares in Uber -- a 4.6% stake -- and has a net worth of $3.5 billion, according to the Bloomberg Billionaires Index.
His latest business, CloudKitchens, got $400 million of funding from Saudi Arabia’s Public Investment Fund, which valued the food startup at $5 billion, the Wall Street Journal reported Thursday.