ISSUE – Mar. 18 | In Silicon Valley, a Voice of Caution Scolds a High-Flying Uber

Travis Kalanick, the famously combative chief executive of Uber, took the stage at a Vanity Fair conference in San Francisco last October and quickly faced a prickly question. Why all the blunders at the company, Vanity Fair’s editor, Graydon Carter, asked. And had Mr. Kalanick learned anything? Off in the wings of the auditorium, Bill Gurley appeared to tense.

Mr. Gurley has a lot riding on Uber. His venture capital firm, Benchmark, bought into Uber six years ago, when the ride-hailing company was a mere pipsqueak. Today, what was a 20 percent stake in Uber is worth billions.

Mr. Gurley is a rare figure, a Silicon Valley habitué who chides some of the biggest start-up stars to show some discipline and drop their arrogant behavior. That day in October, Mr. Kalanick passed Mr. Gurley’s test. He answered calmly, saying that he could learn from leaders who had failed in the past. “We’ve made mistakes,” Mr. Kalanick said. “We always find a way to learn and to get better.” [ NY Times ]
Related : Full transcript: Benchmark general partner Bill Gurley on Recode Decode