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Gawker stories that might have pissed off Peter Thiel and his Silicon Valley friends

Reuters/Jacky Naegelen
Friends in high places.
By Josh Horwitz
Published Last updated This article is more than 2 years old.

Peter Thiel’s financial support for Hulk Hogan in the pro wrestler’s lawsuit against online media outlet Gawker has once again pitted Silicon Valley against the media industry.

Many have assumed that Thiel’s vengeance for the site comes from an article that outed him as gay. But Thiel told the New York Times (paywall) that he’s fighting against Gawker not because he himself felt wronged, but because he felt his friends were.

Thiel didn’t elaborate on which “friends” of his had faced negative coverage from Gawker. But his inner circle includes people so prominent in Silicon Valley that it’s easy to find the stories that might have caused them distress.

Below are some examples of people who have worked with Thiel and who have also been subject to slam pieces from Gawker.

Tesla CEO Elon Musk

Musk and Thiel worked together during the early days of PayPal, and Thiel later called Musk the “most impressive member” of the “PayPal mafia”—the term used in the Valley to describe the company’s first employees.

Gawker provided regular skeptical coverage of Musk’s ambitions for Tesla, which was suffering from financial woes in the lead-up to the launch of the Model S. Writer Owen Thomas once declared Musk’s plans to commercially release the car a “fantasy,” stating, “The only real source of financial viability Tesla now has is the power of Elon Musk’s imagination.”

Gawker also would comment regularly on Musk’s personal life, specifically on the aftermath of his divorce from his first wife Justine. And in typical Gawker fashion, it skewered his second wife, model Talulah Riley (who was then his girlfriend) when she said she was attracted to Musk out of a mutual love for physics. “Perhaps it was ‘physiques.’ Those British accents are tricky,” Thomas wrote.

Facebook CEO Mark Zuckerberg

Thiel was one of the earliest investors in Facebook, and continues to sit on its board.

Valleywag writer Sam Biddle would frequently call out Zuckerberg for political posturing (full disclosure: Quartz has too). He called Zuckerberg’s announcement of his annual salary of $1 a “PR move aimed at painting a self-portrait of modesty and populism.” And he described as a “quasi-philanthropic” initiative that’s less about getting poor people internet access and more about getting poor people on Facebook.

But at times Biddle’s pieces were more personal in nature. On Facebook’s 10th birthday, Biddle posted leaked photos of a young, possibly inebriated Zuckerberg guzzling wine at a company party. “Here’s to another decade of privacy erosion, buddy,” Biddle wrote.

Investor Marc Andreessen

Netscape founder and prominent investor Andreessen sits on Facebook’s board with Thiel, and also guest lectured at Thiel’s Stanford class on entrepreneurship. “It’s hard to be around Peter and not think, ‘I have to get smarter,'” he once told Fortune.

Andreessen was a favorite target for Biddle, who would often hold up the investor’s public comments as examples of Silicon Valley’s self-righteousness and hypocrisy. When Andreessen posted a rant on Twitter predicting a downturn for startup funding, Biddle argued that Andreessen himself was to blame. “When the next downturn happens, Andreessen and friends will be eager to point back at these tweets and say I told you so,” he wrote. ”They’ll be in less of a hurry to point to their own work and say, We made this happen.”

Biddle would also frequently mock Andreessen’s physical appearance, once describing the bald, portly investor as “the Milky Way Galaxy’s wealthiest hard-boiled egg.” He also penned a piece alleging that Andreessen and his wife Laura had divorced, though they remain married to this day.

Investor Sean Parker

Parker, like Thiel, was another early investor in Facebook. He was also a partner at Founders Fund, Thiel’s primary vehicle for VC investments, until 2014.

Parker arguably received the most brutal treatment from Gawker among anyone in Thiel’s immediate circle. The site had covered Parker’s rumored penchant for drug-fueled partying several times, including when he was barred from Facebook’s board after getting caught by police with cocaine.

It also mocked Parker for his lavish, fantasy-themed wedding to Alexandra Lenas, which cost $4.5 million and caused environmental damage to the forest site it was held in.

But Gawker’s biggest scoop concerning Parker came when he disrupted traffic on a residential street in New York City so Verizion could install a fiber-optic internet connection in his $20 million home.

Parker’s initial email response to Gawker was upfront and cordial. But a reply to Page Six, which picked up the story, contained scathing words about Gawker and founder Nick Denton, and a resentment towards media that’s quite common in the Valley.

You [Page Six]… must feel constant, unrelenting pressure from Denton, that sinister little beast that he is, always nipping at your heels like a tiny obnoxious dog (the kind of dog whose head could only be a fraction the size of Denton’s giant oversized pumpkin head)… Nick Denton is basically Joseph Goebbels’ annoying little shitzu (sic).

Gawker published the letter in its entirety.

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