A few days ago, I got into a bit of a Twitter fight. Peter Thiel, the billionaire venture capitalist, had just admitted to secretly bankrolling the wrestler Hulk Hogan's invasion-of-privacy lawsuit against Gawker Media, and my Twitter stream was full Thiel's VC colleagues applauding his actions and celebrating its result: a $140 million judgment that could force the publisher's sale or closure. 

One of the celebrants was an early-stage investor I'd met recently at a cocktail hour. He seemed like a nice enough guy, if a bit clueless about the lives of journalists. (When I told him my wife was pregnant, he suggested I do what he did and hire a night nurse for at least the first three months. He said it as though he were recommending a brand of diaper rash cream, not a domestic servant.) I saw room for productive engagement. 

Granting, I said, that publishing a sex tape was a serious error in judgment by Gawker's editors, did that mistake really merit a judgment so large it amounted to capital punishment for an entire company, one that has produced plenty of worthwhile journalism and writing and employs dozens of people? "You gotta read the history on the case," he replied. "It's not bad judgment -- it's pure trash and character attack masked as 'news.'" 

Aha, I thought, I have you. Clearly, my VC friend didn't know whom he was attempting to educate. Before moving to San Francisco, I spent more than 10 years covering the media industry -- its awkward transition to digital, the impact of search and social media, the rise of online power players like Gawker and BuzzFeed. I once spent six hours interviewing Gawker founder Nick Denton, about the Hogan case and other matters, for an 8,000-word Playboy interview. Portions of the article were read to the jurors at the trial by the prosecution. I informed my sparring partner of this, thinking it would bring him up short. 

He didn't break stride. Gawker, he declared, had crossed a line, and if that meant its demise, that was no loss. The free market for ideas would ensure other news organizations would "pick up the slack" to make up for Gawker's contributions, he assured me, and any writers who "care about their business models" would find new jobs.

That left me sputtering. Here was a tech investor, one who specializes in "cloud infrastructure," "big data," and "digital health," lecturing a lifelong journalist about the limits of free speech and the economics of the industry I covered. I was, in a word, flabbergasted.

But I wasn't alone. Publicly and privately, this sort of exchange has been playing out again and again for the past few days. For journalists, Silicon Valley's reaction to the matter of Peter Thiel vs. Gawker has been a painful object lesson in just how little our values are shared or even understood in America's new power center. 

I say "painful" because we truly believed otherwise. We tech reporters tend to think of venture capitalists as our wealthier, more earnest cousins, basically like us only with nicer cars and better Strava times. Indeed, some notable VCs, like Sequoia's Michael Moritz, are former journalists. Our jobs are superficially similar: We both spend most of our time interviewing people, boning up on unfamiliar topics, trying to figure out what the next big thing will be. 

But it turns out not only are VCs not like us; they don't even really like us. We're too different. The press is expected to be antagonistic, to vet and push back on the claims of companies like Theranos and Zenefits and keep them honest. VCs treasure harmony. "Alignment" is a totem word for them. So strongly do they believe in the possibility of the win-win, some of them don't even see a problem with investing in companies that compete with each other. How do you align alignment with antagonism? You don't. 

Journalists are skeptics. We have a saying: "If your mother tells you she loves you, get a second source." We are professional nit-pickers, of other people's mistakes and our own. It's a big reason terrific reporters often make for boring, careful opinion columnists. 

VCs are believers. They don't mind being wrong about the small things because they're so sure about the big ones. Their business model presupposes failure nine times out of 10, but the galactic payoff from No. 10 will sweep away all memory of the other nine.  

The peculiar language of VCs reflects a bone-deep confidence in their ability to parachute into unfamiliar intellectual territory and quickly master the basics well enough to wager millions of dollars of other people's money on their knowledge. Thiel's pet phrase is "to a first approximation," a locution that suggests being wrong about something isn't really being wrong as long as you're wrong in the right general direction. VCs like to boast of their skill at "pattern matching," the idea that you can understand an unfamiliar industry or business model by analogy to one you know better. (Ben Horowitz has  written about the problem of his colleagues who "confuse pattern matching with knowledge.")

Perhaps the strangest bit of VC-speak is "domain expert," referring to someone with deep specialized knowledge of a topic. The rest of us already have a word for that kind of person: "expert." But that implies people without deep knowledge aren't experts. In venture capital, that's not a universally accepted notion. The job of a VC with a broad portfolio is basically to be an expertise expert. 

More than anything, that sort of free-floating certitude is what scares journalists about Silicon Valley. It scares us because it feeds our sense that powerful tech entrepreneurs and investors are making decisions that shape the fate of the news business without having thought particularly long or deeply about that business and its function in society.

When he's not secretly waging legal jihad against publishers, Thiel is a board member at Facebook, a platform whose sheer scale and capricious product moves force publishers to revise their digital strategies on a quarterly basis. Marc Andreessen, who tweeted his approval of Thiel's Gawker-stalking, is another Facebook director and his firm invested $50 million in BuzzFeed. Vox, Mic, Medium, Business Insider -- most of the fastest-growing media startups are now venture backed. No doubt there are many venture capitalists who revere the values of journalism, who see the news business as something other than just another industry to be disrupted and the First Amendment as more than just an instrument for special pleading. We just haven't heard much from them lately.

Which brings me back to my sparring partner. After a few more pointed back-and-forths and a couple "Can you believe this guy?" asides on both sides, the investor I'd been arguing with blocked me on Twitter. That is to say, he used the power of technology to insulate himself from speech he found disagreeable.

It's hard to think of a better metaphor for the gulf that divides journalism from Silicon Valley. 

Published on: May 31, 2016