Owen Davis & Avi Asher-Schapiro

When Ayda Valilar first read that Uber was losing billions of dollars, she couldn’t believe it. She’d been driving for the ride-share service for nearly five years, and had tried unsuccessfully to organize a union in Los Angeles with other Uber contractors. How could a company that had so adamantly played Goliath to the drivers’ David be so deep in the red?
 
 That was the reaction among many casual observers when Bloomberg reported in late August that Uber had lost $1.6 billion in the first six months of 2016, hemorrhaging capital on subsidies designed to make its pricing more competitive. It was the latest in a string of bad headlines for Uber. A week earlier, a federal judge ruled the company could be on the hook for more than $1 billion in labor costs. And just before that, drivers in Seattle beat back a legal challenge to dissolve the first-ever Uber drivers union.