Riding an Uber With Sam Biddle, the Tech World’s Least Beloved Watchdog

Sam Biddle, photographed by Christopher Anderson/Magnum Photos/New York Magazine Photo: Christopher Anderson/Magnum Photos

Sam Biddle stands outside the high glass door of the Tesla dealership in Chelsea, squinting through the shiny pane. He pulls it open with a flourish to survey the showroom. Two model cars are crouched like a pair of bionic panthers. “Wow,” he says ­quietly, exhaling. Biddle, 27, is a bomb-throwing blogger who, from his perch at Gawker Media’s tech site, Valleywag, has become an icon of anti–Silicon Valley backlash. Tesla corporate had mysteriously canceled our scheduled test drive at the mention of his name. So we’d decided to try our luck at strolling in off the street.

A sales rep glides over, with perfectly tailored pants and alien good looks. “Can I help you?” he inquires, one elegant eyebrow cocked. He eyes Biddle’s Ray-Bans (still on, indoors) and the puffy striped scarf with a whiff of European discothèque wound around his neck.

Where do you live?” the rep asks.

Williamsburg,” says Biddle.

The man takes a moment to arrange his face. “We can only squeeze in serious buyers,” he says at last, muttering something about checking the schedule, then disappears.

Biddle laughs. “He’s going to go back and get security,” he says. A few minutes pass with no sign of the Tesla guy. “Let’s just go,” Biddle says, and we head out into the bright afternoon.

At this point, Biddle is used to such treatment. Over the past year (one in which tech-wealth resentment reached such a fever pitch that there were protests against Google buses), he has swaggeringly taken on the “techno-libertarian goon squad,” as he puts it. The result is that ­Biddle—who has no interest in moving to San Francisco—is perhaps the most hated journal­ist in the Bay Area. He was once, with no explanation, escorted out of a TechCrunch party by two massive bouncers. (TechCrunch, Biddle declares, is the prime example of how much “Silicon Valley gets its ass kissed every day,” thanks to a species of article he characterizes as: “Man, Facebook has made it faster to upload photos; that’s pretty great.”) Marc Andreessen has taken to Twitter to denounce Biddle’s Valley­wag stories as “flatly incorrect.” Online, Biddle is routinely pelted with insults such as, to give a mild example, “Sam Biddle you are a piece of human shit.”

Why Biddle stirs up so much bile is obvious. His style is proudly resistant to nuance (“Read This If You Want to Hate SXSW and the World in General,” “How a Start-up Went From Hype to Clusterfuck”) and largely absent of reporting (hard to do when the gentlest thing you call your subjects is “Silicon Villains”), save the occasional gossipy tidbit, often emailed his way from an anonymous source. (One of his most notorious scoops was outing Sergey Brin’s 26-year-old mistress.) In the case of Tesla, Biddle happens to be the author of several withering posts about CEO Elon Musk. “If I were the kind of person in real life that I am at my computer,” Biddle says, “I would be alone.”

Standing on the sidewalk in the shadow of the Tesla logo, we call an Uber ride instead. Uber may be Biddle’s main adversary. He has called out CEO Travis Kalanick’s “condescending asshole routine” and skewered the company’s surge-pricing practices. “I feel like I shouldn’t be giving them money when I think they are such bad executives,” Biddle says, climbing into the black leather backseat. “So, I’ve tried to stop.” He hasn’t succeeded. “Listen, these products are good. They just have a lot of shitty consequences,” Biddle says of Uber and its ilk, jabbing the air for emphasis. “A nuclear bomb is masterfully engineered and designed. It dropped and did what it was supposed to do well.” He takes a moment to consider how that sounded. “Please do not write that I compared the Manhattan Project to Uber.”

Biddle normally tries not to overthink his mudslinging. “When I started this job, I did have to sort of acknowledge that I was never now going to work at a start-up or be employed by Google or something,” Biddle says. It’s easy to imagine Biddle’s brogrammer alter ago. After all, he’s a Johns Hopkins grad who throws around phrases like seed round, prides himself on disrupting a staid industry, and has the goofily laid-back vibe of a sidekick in a frat comedy. But he gave up on the prospect of joining forces with the tech world pretty early on. “I mean, I failed math in high school.”

As we cruise across town, Biddle pulls out his iPhone: 16 voice-mails and missed calls, “all from my mom and various bill collectors.” “On my home screen, it’s just Uber,” he jokes. Actually, it’s an array of neatly organized apps, which Biddle excitedly catalogues. There’s the calendar app Peek (“I love Peek”), Chipotle (“amazing”), ­OKCupid (“I should delete that”), the anonymous social-sharing app Secret (“Such a great app”). 

Biddle leans back against the upholstery. “I want to keep doing this forever,” he declares. “That is, I hope I have the constitution to be doing something like this in ten years. It’s basically sticking your head in a toxic gas cloud every day.” But Biddle admits that covering what he calls “our coddled new overclass” has given him something of a hero complex. And the more bridges he has purposefully burned, the more his sense of mission has grown. “These are people and companies and places that deserve to be embarrassed and upset,” he says. Also, he adds with a smile, “I like attention.”

The role of tech gadfly was an accidental one. After college, Biddle moved to New York and applied for editorial internships at magazines and publishing houses, from which he was roundly rejected. Then he wrote a series of essays for the Awl about his travails as an unemployed philosophy major trying to break into writing. (“I sat jobless in Tompkins Square Park the other day … talking about sad, idle white person things.”) His essays stirred up some whiny-millennial mockery. But they also caught the attention of the editor of Gawker’s gadget blog Gizmodo, who hired him. Biddle jumped to long-dormant sister site Valleywag a year ago when it was revived to capitalize on the media’s fascination with the latest tech bubble.

We pull up outside the Ace Hotel, watering hole for the New York tech crowd and one of Biddle’s favorite haunts. Strolling through the lobby beneath a canopy of funky metal light fixtures, he offers a quick rundown of the scene. “Those seats are for conspicuous laptop usage,” he says as we pass a long central table crammed with 20-somethings in statement eyeglasses.

I had one of the best dates of my life here,” he adds, gesturing to the crook of a distressed-leather couch. “Then we made out over there.” He points across the room.

Some of Biddle’s critics complain that the Valleywag narrative is too neat, its view of the corrupt tech overlords and the exploited public too Manichaean. “But I mean, I would never say these people are evil,” Biddle objects. Reminded that he had tweeted the words “Google vs Facebook: which company is a more literal manifestation of evil on our planet?,” he amends that statement. “Oh, yeah, I guess I did. Yesterday.”

In the café attached to the Ace lobby, Biddle sips an Americano. This year, he says idly, Valleywag should be just a little bit nicer. Maybe a few posts about start-ups he doesn’t hate. He adjusts the Ray-Bans on top of his head and grins. “But I would still like to have a 20-to-1 ratio of ruining people’s days versus making them.”

*This article appeared in the April 7, 2014 issue of New York Magazine.

Riding an Uber With Sam Biddle