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Uber Just Hired Obama's Most Ruthless Political Genius

David Plouffe has a lot in common with his new company's fanatical CEO

Handout/Getty Images

My first thought after hearing that Uber hired David Plouffe to be its “campaign manager” in the fight against bureaucrats and taxi companies was a story I first heard in 2008. Back then, Plouffe was still managing more pedestrian operations, like presidential campaigns. And the campaign he was managing had just taken a kick to the teeth in New Hampshire, where it had expected to wrap up the Democratic nomination only to be shocked by Hillary Clinton.

Pretty much every operative on the Obama campaign was either dazed or weepy-eyed or both at this point. Except for the militantly unsentimental Plouffe. He’d long calculated that Obama’s path to the nomination involved fighting Clinton to a draw a few weeks later on Super Tuesday, then surging to an insurmountable delegate lead in the Obama-friendly states that followed. He methodically laid out this strategy on a campaign-wide conference call late the night of the New Hampshire debacle, then ended with a classic Plouffe-ian growl: “Now let’s go win this fucking thing.” Obama did, of course—and more or less precisely the way Plouffe laid it out.

There are basically two ways Silicon Valley upstarts like Uber and Airbnb can press their case against the regulators and traditional industries that would just as soon see them die. The first is by persuading the public that they’re really warm, fuzzy, and altruistic. This is the approach Airbnb has settled on, with its constant talk of helping people make friends and build communities. The second is by shunning the pretense of do-gooder-ism and simply mau-mau-ing the regulators and incumbents into submission.1

This is the approach favored by Uber CEO Travis Kalanick, who, after the company raised some $250 million in capital last year, warned the powers that be that the war chest would help him “fight off protectionist, anti-competitive efforts.” Not exactly a sweet-talker that guy. Or one to stand on principle: Under Kalanick, Uber once attempted to stamp out a rival car service by having employees order up the rival company’s cars and then cancel them, simply to take them out of circulation. It was not exactly a high-water mark of fair competition.2 

Perhaps not surprisingly, Airbnb has also drawn from the ranks of Obama alumni to wage its campaign for acceptance. But there were always two sides to the Obama project, the hopey-change-y, David side, and the steely, pragmatic David Plouffe side, and Airbnb has opted for the former. Most of the people who run Peers, the industry front group co-founded by a top Airbnb executive, are former Obama operatives who love to wax on about the ways Airbnb and its “sharing economy” cousins help urban-dwellers live more connected, fulfilling lives—the way small-town Americans have lived for generations. 

Plouffe has begun his Uber tenure with a nod to the Airbnb strategy, telling The New York Times that, “Uber is making transportation safer. It’s providing jobs; it’s cutting down on drunk and distracted driving.” But, in truth, he’s always been an operative that the ruthless Kalanick could love, and I suspect that’ll continue. During the 2008 race, when pretty much every traditional Democratic interest group wanted care and feeding from the Obama campaign, Plouffe told them to, in effect, go screw themselves. “He didn’t want to have a desk”—a formal outreach effort—“for every ethnic group,” one Obama campaign colleague said in my book on Team Obama. Plouffe even came up with a name for all the Democratic kibitzers he disdained: “bed-wetters.”

After the campaign, meanwhile, Plouffe displayed no particular hang-ups about cashing in, pocketing $50,000 for a speech in Azerbaijan to a group affiliated with the country’s repressive regime. (Plouffe donated his speaking fee to democracy activists amid the inevitable backlash.)

And then there is Plouffe and Kalanick’s shared affinity for creating “facts on the ground.” Kalanick’s approach, as one former regulator summed it up to me recently, is “Get super popular, ignore the laws, and if you try to enforce them, we’ll use the power of the bully pulpit”—that is, mobilize loyal customers to rise up in protest. In fairness, Airbnb does some of this too, but generally a kinder, gentler version, whereas Uber has gone so far as to trick it’s own customers into engaging in political activism on its behalf.

For his part, Plouffe is also a big believer in simply doing what he wants without asking first. Back in late 2012, as he was preparing to leave his position as White House senior advisor—Barack Obama’s top in-house consigliere—the West Wing was divided over who should succeed him. Plouffe resolved the question by abruptly ceding all his responsibilities to his eventual successor, then-communications director Dan Pfeiffer, just before he stepped down. “The way it got handed entirely to Pfeiffer was that Plouffe stopped doing the job one month before he left,” says a longtime Obama adviser. “Everyone was expressing frustration that [Plouffe] won’t talk to anyone, won’t answer email. [It was] ‘Let Dan do it.’ He started doing it without permission.” (Plouffe didn’t respond to an e-mail and Pfeiffer declined to comment.)

The move was all the more curious given that it occurred in the middle of a tense standoff with Republicans over the dreaded “fiscal cliff.” But the approach did have something to recommend it in the end. “Things were working better on the organizational side. Plouffe did them a big favor,” says the adviser. “I’m not sure [Dan] would have been the first choice. But he demonstrated to people he could do it.”

As it happens, Kalanick thinks of himself in a similar way: He and Uber are doing you a big favor, even if you can’t appreciate it yet. Something tells me David Plouffe will fit in quite nicely. 

  1. Well, there’s a third way—which is hire back-slapper lobbyist types to make your case behind the scenes. But pretty much everyone does that, so there’s not a whole lot of differentiation here.

  2. Kalanick denied ever engaging in such behavior in an interview on Tuesday.