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Startups and Self-Loathing at the 8th Annual Crunchies Awards

The Valley loves satire. Or does it?

Nellie Bowles

There was a moment last night — when comedian T.J. Miller (who had called an Uber co-founder’s girlfriend “bitch” multiple times) was smashing a TechCrunch piñata as a hundred people walked out of his performance — that the Crunchies, and the presenter, seemed almost to fall apart.

Still, there is an insatiable appetite for satire in the tech world, especially for someone who can make fun of all these new piles of money, and the show went on.

“You’re run by money,” said Miller, one of the stars of HBO’s comedy series “Silicon Valley.” “We make fun of it with ‘Silicon Valley’ [the show]. That’s why you invited me here. That’s how fucked up all of you are, that you’re literally like, shall we bring the jester?”

The Crunchies, held at Davies Symphony Hall in downtown San Francisco and hosted by TechCrunch, is an annual award show for the startup world, with categories like Best VC and Best Mobile App. It’s a silly, tongue-in-cheek affair, much like the Teen Choice Awards, and everyone (even those jockeying for prizes) makes fun of them.

But people show up. Uber co-founder Travis Kalanick, Snapchat co-founder Evan Spiegel, Salesforce founder Marc Benioff, venture capitalist Ron Conway, and Tinder co-founder Sean Rad all arrived on time and suited up last night. And though the event can be written off as a little-league mess, it’s the best microcosm of the troubled, funny and extremely affluent startup world, which is still struggling to define what a startup is.

Outside the symphony hall, a group of about 40 anti-eviction protestors rallied around a man with a loudspeaker who called himself Con Ronway and dressed in a white wig to mimic the venture capitalist Ron Conway. He shouted out his own set of awards like the “Urban Regression Award” to Y Combinator “for turning a sophisticated and mature city into a frat house.” Winners, wearing pig masks, took their prizes.

 Protestors outside the Crunchies
Protestors outside the Crunchies
Nellie Bowles

Inside, the real Ron Conway was checking in. Did he like his impersonator?

“What? Who?” he said. “Oh, I avoid them.”

As the audience flooded into the auditorium, TechCrunch reporter Josh Constine, who wore a rose lapel pin in his grey suit and whose stylized curl, as always, adorned his forehead, said it was the most significant gathering of startup brass each year.

“It’s the one night of the year that if one building blew up, the tech economy would tank,” said Constine, who would later present an award onstage with Snapchat co-founder Spiegel. “A lot of more traditional companies, their leaders are more interchangeable. Who’s the CEO of Pepsi? It doesn’t matter. With startup founders it does.”

The lights onstage cast a green hue, and next to the podium was a sculpture of an enormous monkey wearing a baseball hat, smashing computers. Hidden behind the screen, which would begin to flash different startup categories and winners, was the symphony organ.

 Protestors outside the Crunchies
Protestors outside the Crunchies
Nellie Bowles

T.J. Miller stepped up for his opening monologue. He rapped nonsensical startup words to great effect and made jokes about Clinkle, a failed payments startup.

The awards started.

In the first category, called Best Technology Achievement, Apple Pay was a nominee. Apple, the world’s most valuable company, is hardly a startup. When Kalanick went onstage, he acknowledged Uber (valued at $40 billion) might not be a startup anymore. The startup world — or at least TechCrunch — is in a funny spot where it seems to have trouble identifying what is and is not a startup.

There were sweet, childish moments. One of the founders of Yik Yak (another anonymous messaging app) opened with “What’s up, we’re from Yik Yak” and the other closed with “Ride the yak!”

Miller came back onstage.

“Finally we prove how terrible teenagers can be when they have absolute anonymity,” he said of Yik Yak.

He made an Uber joke and called out Gabi Holzwarth, Kalanick’s girlfriend who was holding a small white puppy near the front row, who said something, which was inaudible to the rest of the audience.

Miller’s response was quick.

“Bitch,” he said. “Asians aren’t supposed to be this entitled in the U.S. … Is this bitch from Palo Alto?”

Holzwarth gamely explained Shyp, the shipping startup where she works.

“Shyp, the app. It’s like Fedex but it’s spelled wrong,” Miller concluded and cut back to the awards. But he was hardly done with Holzwarth.

The presenters were a little stiff and some missed their lines, but the winners took their awards seriously. The representative for Line said: “Line is really truly a life platform. We’re really the godfather of stickers.”

The Kim Kardashian: Hollywood team’s representative, who took a selfie onstage, spoke about the app’s “journey” for dozens of people who worked on it and called Kardashian a “transmedia storyteller and the mistress of all social media.”

 Protestors outside the Crunchies
Protestors outside the Crunchies
Nellie Bowles

Miller, who plays the buffoonish team manager on “Silicon Valley,” came back to spoof what startup taglines should be:

Lyft: Do whatever you want back there, I’m high.

Tinder: Get robbed by strangers you just had sex with.

Airbnb: Visit new places, meet new people, get fingered on a murphy bed.

When Michael Arrington and Om Malik went onstage, Arrington said he wouldn’t read the script because, “It’s the worst thing I’ve ever seen. Every time someone comes on stage, it’s like ‘oo, ow.'”

Arrington, who himself has a history of controversy with women, called out Miller’s language — “one more ‘bitch’ and something’s going to happen.”

Miller’s final monologue lasted more than 15 rambling minutes (the whole presentation session lasted about three hours). He frequently called out to Holzwarth and to Uber venture capitalist Shervin Pishevar, whom he had nicknamed “Sherv the perv.”

Within the rant were kernels of insight: “It’s so exciting to see Uber even though they’ve been holding back health insurance for the people who work for them. Airbnb has a new design although several people have been raped,” Miller said. “Barkbox: It’s like white people ejaculated onto other white people.”

Afterward, Holzwarth cradled her small white dog outside, while the crowd spilled out into the halls for cocktails.

“I’m pretty sure T.J. was just high, so it wasn’t that big of a deal to me,” she said. “But I do draw the line at the rape and pedophilia jokes.”

“It was a wild performance at the end there,” Kalanick said, grimacing.

The general consensus afterward was that the act was pretty funny, that the prolific use of the word “bitch” was just part of the jokes.

Why do technologists love to be satirized so much?

TechCrunch co-editor Alexia Tsotsis had a clinical diagnosis of the situation: “I think we’re masochists. Plus it’s narcissism. Anytime someone pays attention to you, anytime they know enough to make fun of you, you get a chill,” she said.

Outside, Stewart Butterfield, the co-founder of Slack and an award winner that evening, was having a cigarette. He said the Valley loved satire because it cuts to the core of the issue: Much of the work and money in the startup industry is absurd. It’s almost disturbing. Satire is a way to cope.

“Everyone here must know that everyone is making too much money, and that’s why we love satire,” he said. “If anyone is honest with themselves, they must think that the reward is disproportionate to the work.”

This article originally appeared on Recode.net.