Liz Gannes

Recent Posts by Liz Gannes

Uber CEO Travis Kalanick on How He Failed and Lived to Tell the Tale

The most entertaining presentation at the recent FailCon conference in San Francisco came from Uber CEO Travis Kalanick, who spelled out the many hurdles he faced at his last company, the peer-to-peer content delivery provider Red Swoosh.

Kalanick named names and numbers and shared an astounding number of low points in his speech, which he dubbed his submission for “non-luckiest entrepreneur of the year.” You have to admire the guy for being so levelheaded and funny through it all, at least in the retelling.

Here’s a sliver of a synopsis, though you should just watch the video if you’ve got half an hour:

At Red Swoosh and its predecessor, Kalanick was sued by his own potential investor, Michael Ovitz; was sued by media companies for $250 billion and then sold at auction; “started a revenge business” to turn those litigants into customers; kicked out his co-founder; ran out of money; ran into trouble with the IRS; ran through crappy funding deals and crappier acquisition offers from Microsoft and others; and saw his only remaining engineer recruited to Google. And when that news got on, he lost an AOL deal; got Mark Cuban to invest, but had to go back to coding himself; and talked his way into a VC firm, buying out Cuban’s share so he could sign an EchoStar deal.

Then, in 2007, Akamai acquired Red Swoosh for $23 million. And now Kalanick’s new company — the fancy car-service dispatcher Uber — is a tech industry darling. So you can’t feel too bad for him.

Here’s the video:

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