and of course brilliant systematizing skills—can become a bit more problematic when you rule the world. Like pop stars who are vaulted onto the global stage, world-building engineers aren’t always ready or willing to accept the enormous responsibility they come to hold when their creations start to teem with life. And it’s not infrequently the case that engineers who are deeply mistrustful of power in the hands of others see themselves as supreme rationalists impervious to its effects.

It may be that this is too much power to entrust to any small, homogeneous group of individuals. Media moguls who get their start with a fierce commitment to the truth become the confidants of presidents and lose their edge; businesses begun as social ventures become preoccupied with delivering shareholder value. In any case, one consequence of the current system is that we can end up placing a great deal of power in the hands of people who can have some pretty far-out, not entirely well-developed political ideas. Take Peter Thiel, one of Zuckerberg’s early investors and mentors.

Thiel has penthouse apartments in San Francisco and New York and a silver gullwing McLaren, the fastest car in the world. He also owns about 5 percent of Facebook. Despite his boyish, handsome features, Thiel often looks as though he’s brooding. Or maybe he’s just lost in thought. In his teenage years, he was a high-ranking chess player but stopped short of becoming a grand master. “Taken too far, chess can become an alternate reality in which one loses sight of the real world,” he told an interviewer for Fortune. “My chess ability was roughly at the limit. Had I become any stronger, there would have been some massive tradeoffs with success in other domains in life.” In high school, he read Solzhenitsyn’s Gulag Archipelago and J. R. R. Tolkien’s Lord of the Rings series, visions of corrupt and totalitarian power. At Stanford, he started a libertarian newspaper, the Stanford, to preach the gospel of freedom.

In 1998, Thiel cofounded the company that would become PayPal, which he sold to eBay for $1.5 billion in 2002. Today Thiel runs a multi-billion-dollar hedge fund, Clarium, and a venture capital firm, Founder’s Fund, which invests in software companies throughout Silicon Valley. Thiel has made some legendarily good picks— among them, Facebook, in which he was the first outside investor. (He’s also made some bad ones—Clarium has lost billions in the last few years.) But for Thiel, investing is more than a day job. It’s an avocation. “By starting a new Internet business, an entrepreneur may create a new world,” Thiel says. “The hope of the Internet is that these new worlds will impact and force change on the existing social and political order.”

His comments raise the question of what kind of change Thiel would like to see. While many billionaires are fairly circumspect about their political views, Thiel has been vocal—and it’s safe to say that there are few with views as unusual as Thiel’s. “Peter wants to end the inevitability of death and taxes,” Thiel’s sometime collaborator Patri Friedman (grandson of Milton) told Wired. “I mean, talk about aiming high!”

In an essay posted on the libertarian Cato Institute’s Web site, Thiel describes why he believes that “freedom and democracy are no longer compatible.” “Since 1920,” he writes, “the vast increase in welfare beneficiaries and the extension of the franchise to women—two constituencies that are notoriously tough for libertarians—have rendered the notion of ‘capitalist democracy’ into an oxymoron.” Then he outlines his hopes for the future: space exploration, “sea-steading,” which involves building movable microcountries on the open ocean, and cyberspace. Thiel has poured millions into technologies to sequence genes and prolong life. He’s also focused on preparing for the Singularity, the moment a few decades from now when some futurists believe that humans and machines are likely to meld.

In an interview, he argues that should the Singularity arrive, one would be well advised to be on the side of the computers: “Certainly we would hope that [an artificially intelligent computer] would be friendly to human beings. At the same time, I don’t think you’d want to be known as one of the human beings that is against computers and makes a living being against computers.”

If all this sounds a little fantastical, it doesn’t worry Thiel. He’s focused on the long view. “Technology is at the center of what will determine the course of the 21st century,” he says. “There are aspects of it that are great and aspects that are terrible, and there are some real choices humans have to make about which technologies to foster and which ones we should be more careful about.”

Peter Thiel is entitled to his idiosyncratic views, of course, but they’re worth paying attention to because they increasingly shape the world we all live in. There are only four other people on the Facebook board besides Mark Zuckerberg; Thiel is one of them, and Zuckerberg publicly describes him as a mentor. “He helped shape the way I think about the business,” Zuckerberg said in a 2006 Bloomberg News interview. As Thiel says, we have some big decisions to make about technology. And as for how those decisions get made? “I have little hope,” he writes, “that voting will make things better.”

“What Game Are You Playing?”

Of course, not all engineers and geeks have the views about democracy and freedom that Peter Thiel does—he’s surely an outlier. Craig Newmark, the founder of the free Web site craigslist, spends most of his time arguing for “geek values” that include service and public-spiritedness. Jimmy Wales and the editors at Wikipedia work to make human knowledge free to everyone. The filtering goliaths make huge contributions here as well: The democratic ideal of an enlightened, capable citizenry is well served by the broader set of relationships Facebook allows me to manage and the mountains of formerly hard-to-access research papers and other public information that Google has freed.

But the engineering community can do more to strengthen the Internet’s civic space. And to get a sense of the path ahead, I talked to Scott Heiferman.

Heiferman, the founder of MeetUp.com, is soft-spoken in a Midwestern sort of way. That’s fitting, because he grew up in Homewood, Illinois, a small town on the outskirts of Chicago. “It was a stretch to call it suburban,” he says. His parents operated a paint store.

As a teenager, Heiferman devoured material about Steve Jobs, eating up the story about how Jobs wooed a senior executive from Pepsi by asking him if he wanted to change the world or sell sugar water. “Throughout my life,” he told me, “I’ve had a love-hate relationship with advertising.” At the University of Iowa in the early 1990s, Heiferman studied engineering and marketing but at night he ran a radio show called Advertorial Infotainment in which he would remix and cut advertisements together to create a kind of sound art. He put the finished shows online and encouraged people to send in ads to remix, and the attention got him his first job, managing the Web site at Sony .com.

After a few years as Sony’s “interactive-marketing frontiersman,” Heiferman founded i-traffic, one of the major early advertising companies of the Web. Soon i-traffic was the agency of record for clients like Disney and British Airways. But although the company was growing quickly, he was dissatisfied. The back of his business card had a mission statement about connecting people with brands they’d love, but he was increasingly uncertain that was a worthy endeavor—perhaps he was selling sugar water after all. He left the company in 2000.

For the remainder of the year and into 2001, Heiferman was in a funk. “I was exhibiting what you could call being depressed,” he says. When he heard the first word of the World Trade Center attacks on 9/11, he ran up to his lower-Manhattan rooftop and watched in horror. “I talked to more strangers in the next three days,” he says, “than in the previous five years of living in New York.”

Shortly after the attacks, Heiferman came across the blog post that changed his life. It argued that the attacks, as awful as they were, might bring Americans back together in their civic life, and referenced the bestselling book Bowling Alone. Heiferman bought a copy and read it cover to cover. “I became captivated,” he says, “by the question of whether we could use technology to rebuild and strengthen community.” MeetUp.com, a site that makes it easy for local groups to meet face-to-face, was his answer, and today, MeetUp serves over 79,000 local groups that do that. There’s the Martial Arts MeetUp in Orlando and the Urban Spirituality MeetUp in Barcelona and the Black Singles MeetUp in Houston. And Heiferman is a happier man.

“What I learned being in the ad business,” he says, “is that people can just go a long time without asking themselves what they should put their talent towards. You’re playing a game, and you know the point of the game is to win. But what game are you playing? What are you optimizing for? If you’re playing the game of trying to get the maximum downloads of your app, you’ll make the better farting app.”

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