You probably already know about the PayPal Mafia—the influential and wealthy group of former PayPal executives that spawned many of Web 2.0's biggest hits. But soon, there may be a new generation of Silicon Valley start-up bosses in town.
When Facebook goes public, these current and former Facebookers-turned-entrepreneurs and venture capitalists will be worth billions. What's more, this group is rich in ideas and connections. So when they're not backing promising start-ups, you can bet they'll be tinkering on something of their own. Here are the Mafiosos to watch.
Parker first disrupted the business world—and caught the ire of the music industry—in 1999 when he launched Napster. After founding online address book company Plaxo in 2001, he joined Facebook as its inaugural president in 2004. Since leaving the company under questionable circumstances, he formed Founders Fund with investor and former PayPal executive Peter Thiel. Parker also has been enlisted to help woo the music labels he once irritated: He is a Spotify investor and board member. This June, he will reveal his stealth start-up Airtime, which he created with Napster co-founder Shawn Fanning.
Thiel's résumé includes many of the darlings of the social Web: He was CEO of PayPal, a LinkedIn investor, and one of the earliest backers of Facebook. He remains on the Facebook board and maintains a 2.5% stake, which could be valued at up to $2.5 billion after the IPO. His newest ventures are far more eccentric. Recently, Thiel invested in biotech start-ups looking to reverse the aging process and Blueseed, a moored boat that will float in international waters and serve as a business incubator. Thiel's Founders Fund also flew 50 engineers and entrepreneurs to Hawaii for a secretive three-day conference.
The former Treasury Department chief of staff and Google vice president made news recently about her insistence on leaving work at 5:30 every day to spend time with her children. Although the Facebook COO has yet to found her own company or invest heavily in other start-ups, the upcoming IPO will give her more than enough to do either—with almost 2 million shares, her stake will be worth roughly $1 billion.
Moskovitz was Zuckerberg's Harvard roommate and is the youngest person on Forbes's list of billionaires (he is eight days younger than his former boss). In November 2009, the Facebook co-founder left the company to co-found Asana, a workplace productivity start-up, with former Facebook engineer manager Justin Rosenstein. (Rosenstein is the man responsible for Facebook’s ubiquitous "Like" button.) Moskovitz owns 7.5% of Facebook, a stake that could be valued as high as $7.6 billion. To get Asana off the ground, he landed angel funding from Thiel and Parker, among other Silicon Valley notables.
D'Angelo began working at Facebook the summer after his sophomore year at California Institute of Technology and eventually became the company's chief technology officer. Cheever was Facebook's software engineering manager for three years, until he and D'Angelo left to found Q&A website Quora in April 2009. Quora's $11 million in initial funding came from fellow former Facebooker Matt Cohler, a partner at Benchmark Capital. Back before Facebook acquired Instagram, D'Angelo played a Godfather-like role at the fledgling start-up—he helped the company find engineers, gave feedback on initial features, and was an initial investor.
Hired in 2005 as the vice president of product management, Cohler was the seventh Facebook employee. He remains a "special advisor" to the company, but his primary responsibility today is as general partner of venture capital firm Benchmark Capital, whose investments include Quora and Asana. Cohler's role as venture capital Mafioso comes with experience: Before he started at Facebook, Cohler was protégé to Reid Hoffman, another member of the PayPal Mafia.
Facebook Connect is a set of APIs that streamline the login process across countless other sites across the Web, and Morin is one of the men responsible for the feature's development. Since leaving Facebook in February 2010, he co-founded Path, the buzzy social network that declined a $100 million buyout offer from Google less than a year after it was launched. Whether or not that was a wise decision remains to be seen. He's also invested in a slew of tech start-ups, including inDinero, TaskRabbit, and Tumblr.
Saverin was the Facebook co-founder Zuckerberg pushed out of the company by diluting his shares. (Hello, fans of The Social Network.) Don’t feel too bad for Saverin, though; he was given about $1 billion worth of shares in a legal settlement (now worth $2 billion).
Is he really a legitimate Facebook Mafioso? He still lists himself as an active co-founder on his LinkedIn profile, but Saverin's level of involvement is suspect. Reports say he was last seen living a playboy lifestyle in Singapore. He'll have to do something with his new wealth, but after renouncing his U.S. citizenship, it seems increasingly unlikely he'll funnel some of it back into Silicon Valley.
Read more: Mark Zuckerberg's Smartest Moves