Kalanick wanted to keep Uber from feeling too “big company,” like a Google or an Apple. That meant protecting his employees from corporate bureaucracy. He wanted them to ignore all rules except Kalanick’s beloved fourteen principles. As Kalanick looked upon his empire, he was proud of what he saw—dozens of young, hungry entrepreneurs, autonomous and improvising as each situation required. What Gurley saw was a sprawling mess. He was trying and failing to convince Kalanick to hire another CFO.
