May 18, 2015 ยท 24 minutes

What are we to make of David Plouffe’s sudden replacement at Uber -- uninstalled in favor of Google’s Rachel Whetstone? If you ask America’s business press the answer, apparently, is… nothing at all.

There was remarkable consistency in the headline language announcing the news: Recruiting Whetstone is a coup for Uber, with Plouffe's departure a logical side-effect of that coup, unworthy of further analysis.

The Financial Times reported that the ridesharing company had “poached” Whetstone to replace the former Obama campaign manager. The New York Times put another spin on that same spin: Whetstone had been “lured” to Uber while Plouffe had been “shuffled” to become “chief adviser to the company." One by one, business journalists repeated the message, from Uber’s lips to their readers’ eyes.

If anything, Plouffe’s “shuffling” was presented as a promotion…

“Plouffe has been promoted to advise Uber CEO Travis Kalanick and will focus on strategic initiatives and external affairs,” wrote the San Francisco Business Times.

The Guardian, too, agreed that the move was a win for all concerned...

Whetstone will replace David Plouffe, who was Barack Obama’s campaign manager in 2008 and joined Uber in August last year.

He has been elevated to the role of chief adviser to the company and its chief executive Travis Kalanick, and will also sit on the board of Uber. Only the Washington Post’s Brian Fung got close to acknowledging the suddenness of the announcement: "Uber just gave David Plouffe’s job to a top Google exec,” he wrote.

The sudden switch-up hints at how quickly Uber itself is evolving. When Plouffe came on board, Uber desperately needed a crisis communications team. Not long after he joined, BuzzFeed reported that the company was targeting journalists who'd criticized the firm. Plouffe began appearing on cable TV shows to tout "the good we're bringing to cities," and preparing academic-style studies linking Uber to decreases in drunk driving.

Since then, much of the public backlash against Uber appears to have eased, and it and other ridesharing companies have successfully pressed for friendlier regulations in more than a dozen states. But the company still faces significant regulatory hurdles in many places, particularly abroad. In South Korea, for instance, Uber chief executive Travis Kalanick was recently charged by police with operating an illegal service. The lack of digging can be partly -- but only partly -- explained by Uber's expert managing of the story. The news of Whetstone’s hiring was first leaked to Re/Code’s Kara Swisher — the self-styled “most feared journalist in tech” — who last year gushed in Vanity Fair about Travis Kalanick’s transformation from bad boy to slightly good-er boy just days before it emerged that his company had plotted to smear Pando’s editor-in-chief, triggering exposé after exposé after exposé of Uber’s disgusting behavior towards the media, customers and drivers. A few months before that, Swisher had given Kalanick an on-stage platform to promote the idea that Uber is the poor bullied David to the taxi industry's Goliath.

By all accounts, Swisher felt embarrassed at being snowed by her subject and it's likely Uber was keen to get the relationship back on track. Handing her the news of Whetstone’s appointment seems to have been their attempt to repay that debt, while making sure no tough questions would be asked. The mainstream press — disinclined to do too much follow-up reporting on someone else’s story, let alone one about (yawn!) a tech company — was perfectly happy to play along. Most tech blogs, including TechCrunch and Business Insider ignored it entirely.

But let’s be clear: Plouffe’s departure (and it is a departure) to be replaced by Rachel Whetstone is an absolutely fascinating, and important, story. To Brits like me, it's also a story that telegraphs clearly how Uber intends to get more, not less, aggressive and shady in its dealings with both lawmakers and the media. If you were worried about Uber's power under Plouffe, you should be shitting yourself at what they'll be capable of under Whetstone.

The problem is, to tell the story properly one needs to understand not just the inner workings of Uber but also the surprising, and growing, global influence of a small group of Anglos and Anglophiles credited with guiding Britain's "nasty party" from political exile to landslide electoral victory, despite being tangled up in Rupert Murdoch's international phone-hacking scandal.  Good luck getting American reporters to care about that.

And even if a reporter was inclined to make all those connections, it’s still almost impossible to work out what they mean. Asking questions about the company just leads to more and more questions -- it's far easier to republish Uber's press release and retreat back into the trenches.

In a Plouffe of smoke

Let’s start with the Uber side of things. When Plouffe was first hired, remember, his job title was “campaign manager” — with a remit to help what Travis Kalanick described in his interview with Kara Swisher as “Uber the candidate” to take on “an asshole named taxi.” Said Kalanick of candidate “Taxi”: “Nobody likes him, he’s not a nice character, but he’s so woven into the political machinery and fabric that a lot of people owe him favors.” Kalanick, we’re to believe, wants nothing to do with a character like that.

But now Plouffe is no longer running the show. For a candidate to lose his campaign manager generally means one of three things. One: That the campaign is over (does Uber no longer see Asshole Taxi as a threat? Is Kalanick satisfied that his company’s reputation has been repaired? Neither of those can be true). Two: That the manager wasn’t doing a good enough job and so was fired. (A few weeks ago the New York Times’ Farhad Manjoo asked on Twitter:

“It's almost May, and as far as I can recall there hasn't been a big Uber scandal/big neg[ative] story all year. Can we say: Plouffe is working?”

Is it really possible that Kalanick was unhappy with how successful Plouffe had been in creating a kinder, gentler Uber? Pando has heard from at least one well-placed source that some senior Uber execs felt Plouffe’s tactics were a little too kind and gentle for the hard-charging company.

Or is the opposite true with Kalanick blaming Plouffe for missteps like the UN Women debacle and the company’s continuing troubles with lawmakers? As the Post’s Fung put it: “Turns out that helping to manage a global logistics company is a bit more complicated than running a political campaign.”)

Or a third possibility: That the manager no longer believes his candidate can, or should, win the race.

Given that Plouffe is being handed a board seat and Uber is briefing that his removal from day-to-day operations is a “promotion” it seems like he was bumped upstairs — that is, canned — rather than choosing to quit. But trying to confirm any of these theories only leads to more weird twists. As my Pando colleagues started to call around Uber investors and others close to the company, shortly after the news broke, it became clear that many of those investors hadn’t even been told about Plouffe’s departure or Whetstone’s appointment. Even people who had previously been great sources on the inner workings of Uber sounded stumped when we asked them what had happened with Plouffe: They weren’t being coy, they literally didn’t know he had gone.

Still, at least those investors know who Plouffe is. Asked about Whetstone, no one had any opinions whatsoever, beyond a vague awareness that she came over from Google. Don’t believe me? Go back to the reporting. Whetstone is described, accurately, as a ten year veteran of Google and a former political advisor in the UK. But that’s as far as most reporters bothered to go.

Which is a shame because Rachel Whetstone’s full biography offers plenty of clues as to what Uber might be planning next. And it stretches back way beyond her ten years at Google where she is most famous for gently teasing Rupert Murdoch (more on him in a moment) with animated gifs of laughing babies.

A power couple with trendy headphones

To really understand Whetstone’s importance, and influence, you need to start with her grandfather, Sir Anthony Fisher, who made his fortune as founder of Britain’s first battery chicken farm. Fisher used that money to establish a string of highly influential libertarian think tanks including the Institute of Economic Affairs, Atlas Networks and the Adam Smith Institute. In the late 1970’s, Fisher moved to San Francisco where he shared an apartment with libertarian icon Milton Friedman -- whose economic views Bloomberg Business recently compared to those of Travis Kalanick. Around the same time, Fisher set up the International Center for Economic Policy Studies (aka the Manhattan Institute) with help from his attorney… future CIA director Bill Casey.

Fisher’s influence over British and American politics was perhaps best summed up by MP Oliver Letwin, in 1994:

“Without Fisher, no IEA; without the IEA and its clones, no Thatcher and quite possibly no Reagan; without Reagan, no Star Wars; without Star Wars, no economic collapse of the Soviet Union. Quite a chain of consequences for a chicken farmer.”

Jump to the 2000s and Fisher’s granddaughter had enjoyed a similarly star-studded early career as a political strategist for Britain's Conservative (aka Tory) party — roughly analogous to America’s GOP. Amongst her many accomplishments, Whetstone and her husband, Steve Hilton, are credited with helping transform the party from the racist, homophobic, classist “nasty party” of British politics, to the slightly less racist, homophobic and classist party that was recently re-elected with its first outright parliamentary majority since 1992.

Whetstone first worked with future Prime Minister David Cameron in the 90s at Conservative Party HQ. She then briefly left politics to work alongside Cameron in the PR department of Carlton Communications before joining him to help with his party's (unsuccessful) 2005 election campaign under then-leader Michael Howard. Next she was tipped to join her husband in running Cameron's own electoral campaign but instead left politics and returned to the private sector. Still, that didn't stop her helping Cameron: After joining Google as head of PR, one of Whetstone's first acts was to convince the search engine giant to pay for Cameron and his entourage to fly across the Atlantic to tour California and speak at the company's Zeitgeist conference. (One of the members of that entourage: Steve Hilton.)

Screen Shot 2015-05-17 at 7.24.47 PM

The relationship between Whetstone and the Camerons is by no means limited to 9-to-5 hours. Whetstone was godmother to Cameron's first child, Ivan, and today Whetstone, Hilton and Cameron are all affiliated with the so-called Chipping Norton Set -- a high status group of politicians, celebrities and upper class power-players all of whom have (second) homes close to the same town, not far from London. The Daily Mail has also referred to Whetstone and her friends as "Cameron's Cronies."

As part of the Chipping Norton set, Whetstone and Hilton (and Cameron) are also close with the British arm of Rupert Murdoch’s empire. As the Guardian reported last year:

Just 24 hours before news broke that [murdered schoolgirl] Milly Dowler's mobile had been hacked, Elisabeth Murdoch and her husband Matthew Freud hosted a gathering of the UK's political and media elite at their Costwolds mansion. According to The Mail on Sunday, Guests included… Tory policy guru Steve Hilton, his wife, Google communications chief Rachel Whetstone, Rebekah Brooks and James Murdoch.

A Westminster friend of mine describes Whetstone and Hilton as “a total Tory power couple [but] more trendy/progressive than most Tory couples — less tweed and more expensive headphones.” A Sunday Times profile quoted a political insider calling Whetstone “Margaret Thatcher reincarnated” while The Telegraph described the couple's differing demeanors: "Whereas Rachel gets terribly cross and jumps up and down, [Hilton] is very laid back and easy going."

Power couple is right: In another echo of her grandfather’s career, Whetstone is a former director of Policy Exchange, a UK think tank that has published a variety of libertarian and right wing reports — a casual glance at their website shows paper after paper urging the wider adoption of new technology as a way to reduce the size of government. More troublingly, in 2011, Policy Exchange was accused by the BBC of whipping up Islamophobia in the UK. Whetstone is no longer actively involved in Policy Exchange but — never fear — today that same website boasts as their top story:

We are delighted to announce that Steve Hilton, Visiting Professor at Stanford University and former senior adviser to Prime Minister David Cameron, is joining Policy Exchange as a Visiting Scholar.

Whetstone was also involved in setting up Portland Communications, a lobbying and PR firm that former Tony Blair spin-master, Alastair Campbell (the inspiration for The Thick Of It’s Malcolm Tucker) is now involved with. Current Portland clients include defense giant BAE, Omidyar Network, Facebook, Google and...  (well, look at that!) former Uber partner UN Women. Just today, the BBC reported that Portland had invited reporters to Qatar for a PR junket on behalf of the country's government only for some of them to be thrown in jail for daring to report on human rights abuses.

Everyone in UK politics who I asked about Whetstone was agreed on one thing: She’s the person you bring in if you need to convince everyone that your company isn’t quite as nasty as it appears, and if your current spin doctors aren’t delivering the results you want. First that was Google, and now comes the biggest challenge of her career: Uber.

I have low hopes when it comes to the American business press covering Uber, but even I was surprised at how few journalists bothered to share even the most basic details of Whetstone's background with their readers. That stuff sits barely below the surface and speaks volumes about the famously ultra-libertarian Travis Kalanick’s decision to replace Plouffe with her at Uber: An Obama liberal booted upstairs to make way for a multi-generation Cameron conservative/libertarian.

Less shocking is the American's media’s unwillingness to delve any deeper into the other bizarre web of connections that link Uber with Whetstone and her British political pals. People who go up against those folks rarely come away unsmeared, and we all know what Uber is capable of on that front. In any case, it takes a whiteboard and a lot of patience to even begin to get the threads straight -- and there's little evidence that anyone in Washington, Wall Street or Silicon Valley really cares what lurks under Uber's hood, so long as it keeps providing fancy limos and killer profits.

Friends in low places

The key thing to understand is that Whetstone’s connections to Uber began long before this past week. Remember that widely-reported dinner, late last year, at which Uber’s Emil Michael laid out his plan to smear Pando's Sarah Lacy in order to stop her writing about the company? Of course you do — everyone wrote about it. What was less well reported is the identity of the person who hosted the dinner.

His name is Ian Osborne, a British political fixer who… wouldn't you know it?... is another of the people credited with rebranding David Cameron, along with his colleagues Rachel Whetstone and Steve Hilton. Both Whetstone and Osborne appeared together in a 2010 Vanity Fair profile of Cameron written by American journalist Michael Wolff. In the article, Wolff raved at how "impressed" he was by Cameron while describing Rachel Whetstone as “a marketing prodigy” who, with her husband, “will become the pillars of the Cameron marketing and brand-development brain trust.” That same year, Wolff described Cameron as "Churchillian, making President Obama seem even more like a wishy-washy, ever-treading-water bureaucrat." More on Wolff, too, in a moment.

It's not immediately obvious why a British political fixer would be hosting a dinner for Travis Kalanick in New York, which is possibly why almost no journalist thought to ask.

Here's the answer: Like Whetstone, Obsorne remains close to both the Cameron government and to Rupert Murdoch’s British lieutenants — but, again like Whetstone, Obsorne no longer spends much time in UK politics, preferring instead to act as a kind of reputation fixer for hire for US tech companies and international billionaires.

According to Osborne's official bio: "Ian Osborne advises political and business leaders on international affairs, and on all aspects of their reputation."  He has worked with people like Sean Parker,  Marc Benioff and Michael Bloomberg and is also a partner in DST, the tech investment firm headed by Russian oligarch Yuri Milner.

Uber is Osborne’s latest client, and possibly his most controversial. It was Osborne who came up with the idea of hosting a dinner in New York where Uber could shmooze journalists and convince them that Kalanick and co weren’t quite the monsters we all believe them to be. Or at least that was the stated purpose of the event. Awkwardly, it was at that dinner that Uber SVP of Business (and former Defense Department staffer) Emil Michael, believing himself to be speaking off the record, explained to Buzzfeed’s Ben Smith his strategy for smearing any journalists who dared to cross Uber.

I’ll leave it to the conspiracy theorists to consider whether it was always the plan for Michael to seed the idea to journalists that Uber won’t hesitate to play dirty with those who cross them. What’s certain is that, after Smith blew the whole gaffe, Uber, with help from Osborne, went into damage limitation mode — first trying to convince Smith to suppress his reporting, then bleating that Michael’s comments were off the record and so somehow didn’t count, then publicly apologizing for Michael’s “lack of humanity” then using surrogates to plant the idea that Michael hadn’t made the comments at all before finally settling on what they figured was the most plausible excuse: that Emil Michael was drunk and that his comments didn't "reflect his views."

That last one seemed to satisfy most reporters — largely because it gave them an excuse to stop thinking about any of the other terrifying possibilities. Who amongst us hasn't got a little wasted and laid out a $1m plan to hire "four to opposition researchers and four journalists" to destroy a female journalist by "going after" her family?

Both the original plan for the dinner and the clean up afterward were testament to why Uber, and others, pay Osborne the big bucks: Inviting journalists to an off-the-record briefing at which — oops! — those journalists accidentally learn what happens to critics who take on Uber. Had the veil of secrecy remained that would have been a masterstroke. What was certainly brilliant was how Uber, helped by Osborne, reduced a gigantic scandal into nothing more than a drunk guy speaking out of turn.

A sheep in Wolff's clothing

For that last piece of media trickery, Osborne needed to call upon some local help — a friendly insider who could help push Uber’s side the of the story inside New York media. Step forward, Michael Wolff — the Vanity Fair writer who relied on Osborne and Whetstone as sources for his coverage of their old boss, David Cameron. Coincidentally, Wolff is also tight with other members of the Chipping Norton Set thanks to his closeness with Rupert Murdoch and his trusted lieutenant, former Sun editor Rebekah Brooks.

Readers of Wolff’s (thoroughly enjoyable) first book, Burn Rate, and of his countless love-letters to Rupert Murdoch will know his modus operandi: posing as an outsider — snarking his way through Silicon Valley, or New York media, or Britain’s upper classes — while barely able to hide his desire to be accepted by the same people he claims to hate.

Here’s Wolff chortling at how Britain thinks anyone cares whether Brooks is guilty in the Murdoch phone hacking trial:

It's one of the more comical aspects of the debate: that, in the universe of information, Britain continues to believe it means something. A priggish debate goes on in Britain, while around it the worldwide flow of information could not care less, barely acknowledging that a debate is in progress, and shrugging off its consequences.

Without a trace of self-awareness, Wolff continues:

Concerns about the British press and its bad behaviour and mendacious owners occur in a solipsistic world of people mostly employed by the media or directly affected by it (that is, celebrities and politicians who get bad press). And largely among people who know each other.

And yet, throughout the Murdoch phone hacking scandal, whenever Murdoch’s brilliance needed to be “explained” to American readers, Wolff appeared like magic…

Michael Wolff: How Rupert Murdoch won the hacking case

The hacking defense, wholly paid for by Murdoch, is the most expensive in the history of British jurisprudence. It was an American-style defense, in which captivating and theatrical lawyers overshadowed the Crown's straightforward prosecution. They showed great flair and style (the judge kept telling the prosecution to speak up and the defense to pipe down), addressing the complicated charges with inundating detail and great confusion. It was certainly the most dizzying defense money could buy. And no wonder Wolff was so well equipped to comment. In a truly awe-inspiring piece of source-dropping, Wolff explained to the Guardian how he had been by Brooks’ side at almost every pivotal event mentioned during the hacking trial…

Brooks, who did not elaborate beyond her flat denial, did go swimming with Murdoch off his boat. She told me this one evening at a party, arranged by Murdoch's son-in-law at the Notting Hill home of the film director Matthew Vaughn and his wife Claudia Schiffer (just to help fill out the picture of Brook's [sic] social strata, which Jay seemed to want to demonstrate but fell short of). She said Rupert had challenged her to a swimming race. If she lost, which she did (that is, she let Rupert win), she promised to give up smoking.
I might add – further setting the scene of Brooks' professional and social circle – that in my conversation with Brooks that evening (she was not yet married to Charlie Brooks, so was still officially Rebekah Wade), she was discussing what made Rupert Murdoch Rupert Murdoch. Her conclusion being that he was "a genius!”

Today, Wolff is firmly established as the lickspittling Boswell of the Chipping Norton Set. As such he can be relied on to turn out a stream of positive stories about Osborne's latest client, with headlines like “Uber -- hated but perfect” and “Uber invades the world.”

It was Wolff who, having recently returned from a trip to London, personally invited Buzzfeed’s Ben Smith to Osborne’s dinner. And it was Wolff who helped clear up the mess afterwards, first trying privately to convince Ben Smith to kill his story before publication, and then using his column in USA Today to pour cold water on the outrage, and even to suggest that maybe Pando and Lyft had staged the whole thing:

Instead of labeling Michael's remarks in such OMG, shock-shocked, clickbait fashion, Smith, or a more skillful writer, might have located them with greater precision on the broader spectrum of meaning and emotion. After all, how likely is it that a company planning to investigate reporters is going to divulge this to a reporter, even in an off-the-record conversation? If you believe that, there are many worthless tech companies I could sell you. So if he did not literally mean we're going to spy on the press, then what was Michael trying to say?

What indeed? Occam’s Razor be damned! But here’s the best part…

BuzzFeed itself — a financial play as much as Uber is — has key investors who are investors in Uber's main competitor, Lyft. Those investors are, too, investors in PandoDaily. Does this have any bearing at all on the cost of tea in China? I don't know. But I know that little in this world is what it seems.

It’s dizzying to imagine how far beyond native Wolff must have gone, or how much contempt he must have for readers, to argue that Uber is the real victim in any of this. For one thing — yes, Pando does happen to share investors with Lyft, but Wolff neglects to mention the inconvenient fact that we have investors in common with Uber too. For another is he seriously suggesting that… what?… Lyft’s investors worked with Pando to convince Wolff’s old pal Ian Osborne to host a dinner at which we... drugged Emil Michael to the point where he drunkenly threatened to launch a smear campaign Sarah’s family? Still, the important thing is that Wolff’s readers were left with absolutely no idea what to believe — which, from Uber’s point of view, is far better than them believing the truth.

In fact it’s likely that you, like me, were probably getting dizzy long before Wolff stepped into the story. The whole towering pigpile is enough to give anyone an attack of vertigo. Here's a recap: Uber’s new spin doctor is a former political colleague of the guy who organized the dinner at which Uber threatened to smear journalists, the continuing fall-out from which she is now tasked with fixing. Both are insanely close with British Prime Minister David Cameron, who was elected into office thanks to the spin doctor's husband. Uber’s leading journalistic cheerleader has previously relied on all of the above as sources, and works quietly behind the scenes to try to prevent unflattering stories about Uber from being published. To make the whole thing more strange, and sinister, all are part of of a tight-knit transatlantic social group that includes Rupert Murdoch and his key lieutenants, many of whom, let's not forget, were recently implicated in the biggest journalistic phone hacking scandal of all time.

And now, in one way or another, they all serve at the pleasure of Travis Kalanick.

It’s at this point: When you start to consider this whole tangled mess — and get back to wonderering why Uber might replace a slick American political fixer — Plouffe — with a network of well-connected British spin doctors, politicians and media cronies — headed now by the granddaughter of Britain’s Ur-libertarian — that the whole room starts to spin. By the time you add in those persistent rumors about Google wanting to acquire Uber— or try to comprehend why a hi-tech cab company has also hired former CIA chief/defense secretary Robert Gates (Emil Michael’s old boss, lest we forget) to chair a division called, in all seriousness, “Uber Military”… well, by then the walls close in and the edges of your vision start to go black.

Tech companies aren’t supposed to be this confusing, or this frightening. And tech reporting is supposed to be sunshine and unicorns — all junkets with billionaires and free iPhones — certainly not something lifted from a Michael Dobbs novel. That’s why, with all due respect to our former colleagues at Verizon TechCrunch, most practitioners rarely go further than rewriting a press release and gobbling down hook, line and sinker each new set of “job creation” stats Uber deigns to pass along.

Never mind that, by now, covering Uber as a simple, successful “tech company” requires a tactical ignorance bordering on Stockholm Syndrome. Either out of incompetence or fear, most American business journalists have decided no good can come from examining Uber’s corporate moves too closely.

Congratulations on your new jobs, Rachel and David!