Art by Danielle Davis

As 2020 begins, Uber CEO Dara Khosrowshahi faces what is shaping up to be a year of reckoning. Uber’s market capitalization has dropped $29 billion since it went public in May. It likely lost five to six times as much money in 2019 as it forecast in presentations to banks two years ago. And it has lost ground in its ride-hailing, scooter and food-delivery businesses, while regulators in cities like London are threatening its ability to operate.

Some early investors who want faster cost cutting have privately contacted the company, suggesting the possibility of a more public challenge if things don’t improve, said an Uber executive briefed about the situation. Meanwhile, senior Uber employees as well as some outsiders are increasingly questioning whether Khosrowshahi, who took over from Uber co-founder Travis Kalanick in 2017, is the right person for the job. 

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