Kalanick, who co-founded the company and owns 10 percent of it, would sell the shares as part of the deal that will see a group of investors led by Japanese tech titan SoftBank acquire a major stake in Uber.
Uber was valued around $68.5 billion during a 2016 capital investment, but that dropped to somewhere above $48 billion in the SoftBank deal announced last week.
Uber co-founder Kalanick, who was ousted as chief executive in June, is selling almost a third of his 10 per cent stake in the ride-services company for about $1.4 billion, a person familiar with the matter told Reuters on Thursday.
As part of the deal, the group will also be investing $1.25 Bn directly in Uber at the $69 Bn value.More news: Next-gen Mercedes-Benz G-Class leaked ahead of debut
Today's report explains that Kalanick originally had offered to sell around half of his stake in Uber, but that ultimately didn't happen due to limits outlined previously between Uber and the buyers, thus putting him at selling 29 percent of his shares.
One of the wealthiest people in the world on paper, Kalanick would become an actual billionaire for the first time as a result of the sale.
The executive himself was accused of being unprofessional, Uber was accused of encouraging a toxic work culture and is now in the middle of a lawsuit with Waymo over the alleged theft of intellectual property, regulators are less-than-impressed with Uber's operational tactics and a slew of sexual harassment allegations led to a number of employees being fired.
Despite that, early investors stand to make significant gains. Kalanick was replaced by Dara Khosrowshahi, who is attempting to turn Uber's image around despite the past.