Now he'll soon be swimming in greenbacks in reality.
Uber Technologies Inc [UBER.UL] co-founder Travis Kalanick, who was ousted as chief executive in June, is selling almost a third of his 10 percent stake in the ride-services company for about $1.4 billion (1.03 billion pounds), a person familiar with the matter said on Thursday.
Kalanick had long boasted that he had never sold any Uber equity, ever.
While the coming financial windfall may sound like a triumph, it can not obscure the tremendous fall of one of Silicon Valley's most high-flying tech executives. This is a reflection of the struggles Uber experienced in 2017. Kalanick said at the time, "I love Uber more than anything in the world and at this hard moment in my personal life I have accepted the investors request to step aside so that Uber can go back to building rather than be distracted with another fight".More news: Golden Globes 2018: 'Oprah For President' - Twitter Cheers Her Emotional Speech
Mr Kalanick, who has on-paper wealth of around $5bn, should net $1.4bn in cash from the sale but will also lose some of his influence over how the company is run.
Uber also is being sued by Google's self-driving auto company, Waymo, which alleges that Uber stole its proprietary tech when it bought self-driving truck company Otto.
While rival Lyft has by a variety of accounts gained some ground in the past year, Uber remains the dominant ride-hailing option in the United States, and has operations in dozens of foreign countries.
Uber told Reuters the deal will be finalised early this year under new CEO Dara Khosrowshahi.