How Dara Khosrowshahi transformed Uber from a band of pirates into a powerful navy

When Uber went public last month in one of the 10 largest IPOs in US history, the company celebrated not just an iconic growth story but also an iconic transformation story. It was just over two years ago that Uber was a company in crisis, engaged in costly conflicts, not just with competitors and regulators but also with its own drivers, investors and employees. The key to this dramatic transformation was new CEO Dara Khosrowshahi’s ability to guide Uber through its ongoing transition from “pirate” to “navy.”

In this latest episode of Masters of Scale, I talk with Dara about his evolution as a leader, and the challenges he faced at Uber. When he was first approached about becoming Uber’s CEO, in fact, he took one look at the mess he’d inherit and decided to turn down the job. He only changed his mind after a conversation with his friend Daniel Ek, the co-founder and CEO of Spotify.

Dara and Uber’s story illustrates both the power of swashbuckling risk-taking in early entrepreneurship (pirates don’t convene committee meetings), and the necessity to evolve from seat-of-the-pants pirate captain to by-the-book navy admiral as a company grows. You’ll hear what Dara learned from fellow Master of Scale Barry Diller, how a single sentence from a young product manager when Dara was a first-time CEO taught him his most important leadership lesson, and the simple questions you can ask yourself to determine if you’re an ethical pirate or a dirty rotten scoundrel.



Entrepreneur. Investor. Strategist.

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