Gawker: valleywag, paypal mafia

David Sacks is having an excellent Memorial Day weekend

Owen Thomas — Mon, 26 May 2008 17:00:00 EDT

David Sacks, the former COO of PayPal turned first Hollywood producer and now CEO of Geni.com, seems to be enjoying himself. Even if, we suspect, he's not following his own advice about Twitter and alcohol.

Why Elon Musk isn't in Fortune's PayPal Mafia picture

Megan McCarthy — Fri, 16 Nov 2007 19:11:55 EST

Accompanying the Fortune article about the PayPal mafia is a fantastic shot of the article subjects dressed as gangsters. But, if you look closely, there are three people missing from the main group shot of the players. YouTube founders Chad Hurley and Steve Chen were, as we surmised, nixed from allowing to participate in the shot once the corporate handlers at Google got wind of the theme. The other missing link? X.com founder Elon Musk, who has a controversial history with PayPal-gang godfather Peter Thiel. So why wasn't Musk included in the large group shot? Did Thiel pull some strings to keep him separated from the core gang?

Nope. There was no acrimony, just a scheduling conflict, Musk told me at the unveiling of TheFunded.com founder Adeo Ressi. (Who, by the way, happened to be Musk's housemate in college.) Musk was scheduled to receive a magazine's innovator of the year award in Chicago and had a hard stop at 12:30 p.m. on the day of the Fortune shoot. The person who coordinated everyone's schedule's flubbed that tidbit, and scheduled the group for the afternoon. Musk had to make do with an individual shot before rushing to catch his plane. Oops.

(Photo by Robyn Twomey/Fortune)

Is Peter Thiel Silicon Valley's godfather?

Owen Thomas — Wed, 14 Nov 2007 17:12:38 EST

Here's the real takeaway from Fortune's long-expected profile of the PayPal mafia: "Peter Thiel has a butler." The former PayPal CEO is living large in Pacific Heights. But he's hardly idle. With PayPal cofounder Max Levchin, masterminding a wide array of startups founded by some of his star hires at the payments company he sold to eBay in 2002 for $1.5 billion. He's now on the board of Facebook, with a stake worth hundreds of millions of dollars, and stakes in Yelp, LinkedIn, Slide, and others besides. He may not quite be the capo di tutti capi imagined by Fortune's photo editors — who cleverly staged a Godfather-inspired shoot, above — but he's created a gang that can run free from the rules of the traditional VC game. Sand Hill Road hates him for it. I say, more power to him — and the rest of his mafiosi. (Photo of Thiel and Levchin by Robyn Twomey/Fortune; Godfather still from IMDB)

Max Levchin has more money, less sleep than you

Megan McCarthy — Mon, 29 Oct 2007 19:30:11 EDT

Sunday's New York Times profile of PayPal and Slide founder Max Levchin tackles the phenomena of serial entrepreneurs. What makes them start multiple companies after a multimillion-dollar IPO or sale? The short answer: Money, but not in the way that you think. Levchin talks about how Slide's exit needs to be more than the $1.5 billion PayPal received, plus inflation, for him to be pleased with the outcome. (Look no further than fellow PayPal Mafia membes Chad Hurley and Steve Chen, who sold YouTube for a PayPal-topping $1.65 billion, for another example of this behavior.) Netcape cofounder Marc Andreessen, who was interviewed for the article, points out the obvious in Silicon Valley: No one here really cares about money in the consumption sense, but everyone cares about having more than the other guy. San Francisco society blog SF Luxe begs entrepreneurs to become conspicuous in their consumption, and we'd like to agree. It's more fun for the rest of us.

The other secret? No one sleeps around here. Levchin offhandedly mentions his life without a company:

"I enjoy sitting on nice beaches and hanging out with my girlfriend and playing with my dog, but that's three hours a day," Mr. Levchin said. "What about the remaining 18 hours I'm awake?"

Unless Levchin has mastered the 30-hour day, we're counting a mere three hours reserved for sleep. Are we sure he's not a cyborg?

More PayPal Mafia mugshots

Megan McCarthy — Fri, 26 Oct 2007 18:46:11 EDT

Thanks to commenter yarbles, we were alerted to evidence of two more members of the PayPal Mafia posing, like YouTube founder Jawed Karim, in mafioso costumes. Pictured, above, Yelp cofounders Russell Simmons and Jeremy Stoppelman. (Stoppelman's the one with the fake mustache. At least, we hope it's fake.) Any more evidence out there? Join the gang.

The PayPal Mafia personified

Megan McCarthy — Fri, 26 Oct 2007 16:05:56 EDT

Seen here, in YouTube founder Jawed Karim's Facebook profile page, the current Stanford grad student (and former PayPal engineer) dressed in disco-era gangster gear. The reason? Karim comments:

lol — yes there is a story. basically a magazine is doing a story about the "PayPal mafia" — a group of ex-PayPal people who have worked together to create companies after PayPal. they took a group photo of us posing as mafia guys, so everyone underwent a full transformation for the photo ;)

Why Karim? We've heard that YouTube's better-known founders, Steve Chen and Chad Hurley, were missing from the shoot. We're sure that the magazine wanted at least one representative from last year's $1.65 billion acquisition — a purchase price, some have noted, that seems carefully calibrated to be 10 percent higher than the $1.5 billion PayPal went for. We bet Google's unimaginative PR drones nixed the gangster-gear appearance.

While the PayPal Mafia's an old story online, it's hilarious that a print magazine would pick up on the meme and actually get some PayPal alumni to don costumes for it. We're wondering, which other PayPal alum underwent the Donnie Brasco treatment? Are there pictures floating about of Yelp founders Jeremy Stoppelman and Russell Simmons clutching tommy guns? Or a shot of PayPal founder Peter Thiel looking like Al Capone? Please send them in.