How Kalanick-Gurley Tensions Shaped Uber of Today

In the run-up to Uber’s IPO, the company presented a new face to Wall Street. Two relatively new executives, CEO Dara Khosrowshahi and CFO Nelson Chai, appeared at investor meetings around the country. Former CEO Travis Kalanick wasn’t even on the stock exchange podium the day of the offering. But it was the relationship between Mr. Kalanick and investor Bill Gurley—both of whom are now peripheral to the company—that indelibly shaped Uber.

That becomes clear in this account of the tensions between Messrs. Kalanick and Gurley, based on interviews with Uber executives, investors and others involved.

From the time Mr. Gurley’s firm, Benchmark, invested in Uber in 2011, he and Mr. Kalanick battled over a variety of issues, most prominently Mr. Kalanick’s aggressive growth strategy and his preference to avoid “big company” practices such as well-staffed finance and legal departments with public market experience. As far back as 2015 and 2016, Mr. Kalanick rebuffed suggestions from Mr. Gurley that Uber prepare for an IPO as a way of instilling more discipline in the company’s management practices.

In their discussions, Mr. Kalanick didn’t try to hide his disdain for Mr. Gurley’s ideas. Early on, Mr. Gurley repeatedly questioned steps Uber was taking to expand ride-hailing geographically, launch a food delivery business, and fight bigger rivals in China. Mr. Kalanick’s response invariably was to dismiss Mr. Gurley’s concerns by saying “Anyway, we’re doing it,” said a person who saw some of the discussions. Mr. Kalanick sometimes would add comments like: “Why are we talking about this?” Later, Mr. Gurley asked Mr. Kalanick to upgrade the management team.