Everything Ventured, What Gained?

Book: "The Leap: A Memoir of Love and Madness in the Internet Gold Rush"

Author: Tom Ashbrook

Publisher: Houghton Mifflin

Price: $26

Book: "eBoys: The First Inside Account of Venture Capitalists at Work"

Author: Randall E. Stross

Publisher: Crown Business

Price: $25.95

We Americans love to create myths about our entrepreneurs and the people who support them. We want to believe that startups are launched by brave men and women who have a passionate belief in maverick ideas. We want to see those pioneers as heroes who don't falter whenever problems arise. We even want to set aside a bit of glory for the financiers who bankroll startups. Venture capitalists are supposed to be modern-day Medicis, distinguished by their generous patronage and by their bold visions.

Those are the popular images. Reality, of course, gets a bit more complicated.

In "The Leap," entrepreneur Tom Ashbrook describes a poignant three-year struggle to launch a business that ultimately became known as HomePortfolio.com. For much of the narrative, he is torn between a desire to build that company and the fear that he is throwing away a good career as a writer and editor at the "Boston Globe" -- and perhaps jeopardizing his marriage as well. Even the mission of his new company is in flux: HomePortfolio starts out with a plan to sell CD-ROMs that will help affluent people design neo-Victorian homes. By the end of the book, HomePortfolio is doing all of its business over the Internet, where it mostly displays information about sinks, stoves, and other household fixtures.

In large degree, "eBoys" is an even blunter assault on the entrepreneur-as-hero myth. The book provides an inside look at Benchmark Capital, one of Silicon Valley's most successful venture firms, made famous by its well-timed backing of Ariba Inc., eBay, Scient Corp., and Webvan Group Inc. Randall E. Stross, who teaches business at San Jose State University, packs his book with juicy accounts of bickering and preening among the firm's partners. As Stross confides in his acknowledgments, "The Benchmark partners did not really know what they had signed up for; if they had, they wouldn't have."

Yet, for all of the legend-defying details that these books provide, both somehow end up portraying entrepreneurs and financiers as remarkably appealing. It's true that the day-to-day drama of Ashbrook's quest is, at times, harrowing. But, by the end of the book, Ashbrook has a company that he can view with great pride. (And his marriage survives too.) As for Benchmark, there's no question that its partners can be pushy, arrogant, and just plain befuddled. Still, they get right almost all of the big decisions that they face -- and they learn some useful lessons from their occasional missteps.

Startup Solitaire

Tom Ashbrook's big idea comes to him almost by chance. We meet him in the summer of 1994, when he is a restless writer for the Boston Globe. The world is changing, and he's worried that if he doesn't think of something new, he will be caught flat-footed. Into his life walks Rolly Rouse, a college friend who wants to build a company that would use technology to help people design their dream homes. "Yeah, it sounded a little crazy," Ashbrook writes. "But weren't new things ... supposed to sound a little crazy?"

For more than a year, the two men putter at this idea, treating it as a sideline to the rest of their lives. But by early 1996, the idea has become an obsession. Ashbrook and Rouse barely notice their families as they pour time into what is now a major project. They woo the few rich people whom they know in an effort to raise at least $500,000. And both men secretly begin to stockpile credit cards as a way to generate cash.

"There is a game that I call start-up solitaire," Ashbrook writes. "You're alone in your bedroom at midnight with a tall stack of credit cards.... You're slowly spreading it out on the bed,... looking for the ones that still have a few dollars left to borrow. It's a game to be played alone. Not many people can stand to watch it."

Yet, after several brushes with financial collapse, HomePortfolio finally starts to thrive. Companies that make Viking ranges and Corian countertops decide that they are willing to pay to be showcased on HomePortfolio's Web site. A venture affiliate of the media company E.W. Scripps decides to invest $3 million. And HomePortfolio starts attracting the kind of positive, high-profile media attention that often paves the way for more good news.