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How Uber CEO Travis Kalanick Rationalizes Bold Decisions

Hello again from sunny Vancouver, the lovely Canadian port city where Uber is banned. I’m here attending the TED conference, where the conversations among overachievers are stimulating, the musical entertainment is invigorating, and the esoteric and work-life-balance onstage presentations betray next to no awareness of existential crises such as an ominous political season in the U.S., the civil war in Syria and coincident migrant disaster in Europe, and the shaky state of the global economy.

The business-tech highlight of TED on Tuesday was a talk by Travis Kalanick, CEO of Uber. He shared data about the long-forgotten rise and fall of a “jitney” industry across the United States a hundred years ago. (Jitney was slang for nickel, the cost of a ride. Who knew?)

Jitneys were immensely popular but were done in by regulations influenced by entrenched trolley interests, said Kalanick. Sound familiar? The long-ago service is exactly what Uber is trying to establish now with its urban UberPool service. A newer service, UberCommute, focuses on the suburbs.

Kalanick’s message was straightforward: Regulations a century ago killed an innovation that could have altered the trajectory of the life of U.S. cities. Don’t let it happen again.

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An intriguing moment of Kalanick’s time under the bright lights at TED came during uncharacteristically tough questioning from Chris Anderson, TED’s congenial chief curator. He asked Kalanick about Uber’s funky new logo. Kalanick: Uber’s old logo began by mimicking a black car shield. Besides, he said, the “U doesn’t mean anything in Sanskrit or Mandarin.” Anderson called Kalanick an enigma whose company tolerated bad behavior toward women. Kalanick called Uber’s period of bad publicity a communications problem. “We felt we were good people doing good work,” he said.

As for how Uber reconciles doing right by its drivers while developing self-driving cars, the Uber CEO said that transition will take a long time (implying drivers will be productive for quite a while yet) and that to ignore the inevitable would be naïve. Uber, he implied, can help drivers and others retrain when the time comes. It’s an opportunity, he said, for “optimistic leadership.”