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, writes Kate Bennermarch in the New York Times. 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.”

Mr. Gurley relaxed visibly. Now, however, Uber faces precisely the kind of test Mr. Gurley has warned about. Former employees have said they were sexually harassed and discriminated against at the company. This month, Uber ended its use of a tool to thwart authorities in various cities who were trying to stop the ride-hailing service, after complaints that the behavior was unethical. Mr. Kalanick himself was caught on a video, which quickly went viral, in which he told one of Uber’s drivers that “some people just don’t want to take responsibility” for their own behavior, using an obscenity. Bennermarch continues by saying that caution is needed at Uber’s helm.

At the same time, Uber is facing business challenges — a tarnished image, legal difficulties and competition from rivals like Lyft — and is spending big to get around those issues. The company needs to resolve the controversies and get its business back on track.

Mr. Gurley has become deeply involved in that effort. In recent weeks, he has been active in a review of Uber’s practices, according to a person briefed on the discussions, who spoke on the condition of anonymity because the conversations are confidential. Mr. Gurley is also helping the company search for a chief operating officer. Throughout, Mr. Gurley has remained one of Mr. Kalanick’s few trusted advisers, and the two communicate several times a week, according to three people who have spoken with the men.

Helping to right the ship at Uber is a somewhat fitting role for Mr. Gurley, who for years has warned about excessive risk-taking on the part of start-ups. Going against the Silicon Valley orthodoxy, the venture capitalist has urged technology start-ups to go public as soon as they are able, instead of continuing to take venture capital funding: Taking on too much venture funding, he has said, can fuel a lack of discipline.

“Bill was the one who pushed hard for my company, Net Gravity, to be profitable at the height of the dot-com boom” in the late 1990s, said Thuan Pham, a tech entrepreneur who joined Uber in 2013 and is now chief technology officer. “It was a very unpopular stance. At Uber, he is willing to speak up too.”

Mr. Gurley, 50, didn’t respond to requests for comment on Uber. In one of three interviews last year, he said of his warnings for start-ups that “I say these things because the longer bad behavior goes on, the worse things end up.”

Uber declined to comment on Mr. Kalanick’s relationship with Mr. Gurley.

Continue reading this longread on

https://www.nytimes.com/2017/03/18/technology/bill-gurley-uber-travis-kalanick-silicon-valley.html

• Is Travis Kalanick the right man for Uber’s CEO position?