The tools for collaboration and direct publishing that Tim Berners-Lee had argued for at the start were introduced to the mainstream during these years as Web 2.0. This phrase immediately stuck in his craw, however. What exactly was new—2.0-ish, that is—about these companies built around user contributions? They were simply fulfilling the original vision for the Web, where “interaction between people is really what the Web is.” 5 There was one vital difference, however. In Web 2.0, the tools for sharing and publishing were part of a social network or service that profited off of what you created there. You weren’t publishing a video to the Web, you were publishing a YouTube video; you weren’t writing a restaurant review on the Web, you were posting a Yelp review. The truly new idea expressed by Web 2.0 was a commercial one, and perhaps that is why Berners-Lee couldn’t recognize it.

There is something jarring about a group of self-styled survival-of-the-fittest free-marketeers committing to a strategy of collective risk and mutual support. At least one pillar of the Silicon Valley ideology was toppled by this arrangement: that success was handed out to an entrepreneur strictly according to ability and hard work, no matter his station in life or place of origin. Marc Andreessen once expressed this faith in individual merit in an interview with the New York Times journalist Tom Friedman, offering another example of how the world is flat: “The most profound thing to me is the fact that a 14-year-old in Romania or Bangalore or the Soviet Union or Vietnam has all the information, all the tools, all the software easily easily available to apply knowledge however they want. That is, I am sure the next Napster is going to come out of left field.” Somehow, things haven’t quite worked out that way. Instead, a collection of male executives from a single company, a few of whom were hired as much for their right-wing political beliefs as for any latent computer or business talent, managed to create a roster of successful companies. A kid in Romania, it seems, no matter how talented, didn’t stand a chance against these guys.

Considering their origin in university friendships and earlier start-ups, networks like the PayPal mafia tended to be nearly uniform when it came to sex, race, and educational background: white, male, elite. Somehow, though, the experience of profiting from connections and college friendship hasn’t diminished the lecturing from Silicon Valley about how other institutions—typically highly unionized ones like the public school system or the automobile industry—are rife with favoritism. Here is Hoffman explaining Detroit’s decline in The Start-Up of You, his business-advice book: “The overriding problem was this: The auto industry got too comfortable. . . . Instead of rewarding the best people in the organization and firing the worst, they promoted on the basis of longevity and nepotism.” Hoffman makes no mention of any similarity to the PayPal mafia, which he describes this way: “My membership in a notable corporate alumni group in Silicon Valley has opened the door to a number of breakout opportunities.”