Answering the Question: Is Uber Doomed?

One of the joys of writing a book is the clever people you meet while promoting it. In New York I was privileged to thrust and parry on these two existential questions with the likes of Bradley Tusk, Uber’s regulatory consultant and host of a penetrating podcast; Leonard Lopate, a silver-tongued and observant host for the local public radio station in New York City; my old friend David Brancaccio, leader of Marketplace Radio’s morning program; Neil Cavuto the Fox News business-coverage chief; and Anne Marie Green and Vlad Duthiers, the lively and intelligent anchors for the CBS News digital network.

Before I tell you how I answered, I’m reminded of a similar line of questioning I faced five years ago, when I published a book about Apple: Were Apple’s best days behind it, given that the company’s operations were optimized around a brilliant man who had recently died? Then I answered that although it would be unrealistic to expect Apple to continue to be “insanely great,” even if Steve Jobs had lived, the company a had good shot at being “merely great” for years to come. Given its consistency and profitability in the years since, I feel vindicated by that hedge of an answer.

Which brings me to Uber in mid-2017, a promising, disruptive, controversial, world-changing company at a crossroads. Having just completed a book focused on its contentious rise to prominence, I’ll first impartially present the bull and bear scenarios.

The case for Uber is that it has built a global business, is cherished by many customers whose use of its service has become a habit, has billions in capital left to spend, and is led by a ruthless strategist and tactician, Travis Kalanick, who’ll do what it takes to win.

The bear case: Uber is a money pit, Kalanick is unable to learn from his many mistakes, its culture is toxic, and its penchant for encountering daily scandals—in turn the result of everything from stupidity to chicanery—will prevent it from moving forward effectively.

Were I a betting man—and I’m not—I’d wager that the company makes something of itself but at a valuation far below its last level of nearly $70 billion.

There is rarely a dull moment at Uber. Don’t expect many in the future.