Macho boys and entrepreneurial gurus

They swear. They hunt. They make millions. The "eBoys" of Benchmark Capital and "Confessions of a Venture Capitalist" show us the ropes of Sand Hill Road.

May 24, 2000 | "eBoys: The First Inside Account of Venture Capitalists at Work"


By Randall E. Stross
Crown Business, 325 pages


"Confessions of a Venture Capitalist: Inside the High-Stakes World of Venture Financing"


By Ruthann Quindlen
Warner Books, 218 pages

Q: "How many venture capitalists does it take to screw in a lightbulb?"

A: "I don't know but it cost me 30 percent of my company!"

With the exception of public relations flacks, there's probably no profession in the tech food chain that suffers from such bad PR as venture capitalists, who have a reputation for being back-stabbing, dastardly, greedy vultures.

Two new nonfiction books want to let the repositioning begin. "eBoys" gives us "venture guys" as boy heroes in their own multibazillion-dollar action-adventure, and "Confessions of a Venture Capitalist" inaugurates the VC as a self-help guru, dispensing advice on all things entrepreneurial. I wouldn't pony up for a 30 percent equity stake in either.

Randall Stross' "eBoys" is the heady tale of the Internet gold-rush years at an ambitious new Silicon Valley venture capital firm, Benchmark Capital, which funded the likes of eBay and Webvan and, over the course of four years, has increased each of its partners' personal net worth by some $350 million.

Stross, a professor of business history at San Jose State University, who also wrote "Steve Jobs and the NeXT Big Thing" and "The Microsoft Way," finagled impressive access to the cloistered world of venture deal-making, sitting in on the heated meetings where the Benchmark partners hash out which entrepreneurs and ideas deserve their enormous cash injections. For a story that takes place largely in conference rooms, "eBoys" is surprisingly fast-paced and engaging: a page-turner laced with juicy, frequently profane dialogue.

But if you don't happen to be an entrepreneur looking for clues on how to woo your own venture capitalist or a newly minted MBA hankering to nail a cool $350 million for yourself in four years, what makes "eBoys" compelling isn't what the partners do or don't fund and why; it's how they think of themselves.

It's rapidly clear that the guys at Benchmark have utter contempt for exactly the kind of men that outsiders might take them for: filthy-rich power brokers, keepers of the moneybags, who green-light or squash the grand schemes of struggling entrepreneurs at their whim.

The eBoys at Benchmark, which has only been around for four years, absolutely bristle at being mistaken for some blue-blood, monied club, though that's precisely the way they regard their arch-rivals at Kleiner, Perkins, Caufield & Byers, which was established in 1972 and is the home of celebrity VC John Doerr. "The haughtiness of aristocrats versus the scrappiness of up-from-the-bottom plebeians"; that, Stross writes, is how they regard the culture of Kleiner's firm as compared to their own.

The Benchmark partners even worry that their own kids, growing up unfathomably rich, will turn into the kind of priggish bow tie- and suspender-wearers they abhor. "I'm going to have kids like the kind I hated when I was a kid," worries one partner.

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