Self-deprecating in an almost old-fashioned way, Ashbrook seldom pulls back from his narrative to explain why his startup ultimately beats steep odds and survives. But the most important clues to the company's survival seep out anyway. Both founders (Rouse especially) always believed that the world needed their product, even if they weren't always sure how to get it to market. To ensure that production quality and user interfaces were better than most people might have expected, for example, they attracted top technical talent from MIT even during their most embryonic stage. And, for all of their private doubts, Ashbrook and Rouse showed brave faces to the outside world.

On a (Bank) Roll

There's not a lot of self-effacement in the Menlo Park offices of Benchmark Capital. The firm's most ebullient partner, David Beirne, is a former executive recruiter for whom bravado isn't merely a personality trait -- it's the essence of his strategy. In a community where others use a four-door BMW or Audi as an understated sign of wealth, he drives a Porsche 911.

Like a flashy basketball player who wins over a crowd with his skills, Beirne eventually gains his partners' approval with his prowess. He is Benchmark's biggest champion of investing in Webvan Group, an online grocery company that (at least in the early days after its November 1999 public offering) looks as if it will become a giant success.

Even when Beirne misfires, his audacity is instructive. At one point, he tries to coax his partners into making two big investments at the same time -- one in priceline.com, the other in TriStrata, a secretive company that claims to be on the verge of a breakthrough in computer encryption. Stross provides us with ringside seats during those deliberations, showing us the partners' mix of ardent faith and outright scorn. Beirne portrays both businesses as having the potential to achieve multibillion-dollar valuations. One partner, Kevin Harvey, calls priceline's losses "terrifying." Before long, terms like "chickenshit" and "prick" are flying around the room.

In that instance, Benchmark makes a mistake. The firm doesn't invest in priceline, which becomes a stock-market darling, but it does bankroll TriStrata, which stumbles. Yet the partners regroup. Robert Kagle, the firm's most experienced partner, reassures Beirne that his colleagues want him to pursue bold, risky deals. And Harvey, who was a strident opponent of the priceline deal, gradually recalibrates his worldview, making room for the idea that even seemingly dangerous investments may be worthwhile.

At least 10 times a year, Benchmark's partners sink major amounts of money into companies that are at such an early stage that risks are most immediate and success seems far away. The partners also pour a lot of energy into recruiting strong management teams and helping draft strategies for those companies. Sometimes knowing what not to do is the key to a good investment. At one point in 1998, well before the company is ready to go public, eBay gets an acquisition overture from OnSale, a more established online merchant. Two Benchmark partners -- Bruce Dunlevie and Andrew Rachleff -- argue vehemently against OnSale's initiative, maintaining that eBay has too bright of a future to allow itself to be swallowed up by a competitor -- an argument that the stock market later vindicates in a gigantic way.

By the end of "eBoys," it becomes clear why venture capitalists aren't seen as mythic figures in the way that entrepreneurs are: VCs play a role akin to studio bosses in Hollywood, putting talented people together, helping natural hits become even bigger hits, and worrying a lot about the numbers. Still, Kagle, in the book's final scene, argues persuasively that there is something special about what he does. Nine times out of 10, he says, an entrepreneur is taking on a big, established system. If his firm's money helps a little guy win, then that's "exhilarating," he says. "It's confirmation that one person with courage can make a difference."

FC Recommends

John Seely Brown is one of the most brilliant technologists and business thinkers we know. He's also a longtime member of the Fast Company community. Chief scientist at Xerox and director of that company's fabled Palo Alto Research Center, "JSB" coauthored an article for the premiere issue of FC that challenged conventional wisdom about how people work and learn.

Now he and historian Paul Duguid have released a book that challenges conventional wisdom about the impact of digital technology. "The Social Life of Information" (Harvard Business School Press, $25.95) offers a series of provocative essays that are meant to correct the "tunnel vision" of Web wizards and other digerati. It's time to look beyond our obsession with technology and information, the authors argue, and to appreciate how "social networks" -- relationships between people -- shape how ideas move, how people work, and how we live. It's also time for you to reckon with the sensible arguments put forth in this book.

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