Securing quality time with an Internet tycoon—even for a Washington Post reporter wielding a book contract—can be vexing.

“I would have had an easier time pulling my body hairs out one by one than get Steve Case to talk about himself,” says journalist Mark Leibovich. “We had an infuriating one-hour, off-the-record sit-down that he seemed to relish as much as a hernia. Then his flacks insisted that we do the rest by e-mail, because it was so ‘cool.’ I got a lot of e-mails from him—he’s a very good e-mailer—but they were extremely unrevealing.”

Leibovich was eventually able to fill in the blanks of Case’s life by talking to dozens of people who knew him. But the author of the just-released The New Imperialists: How Five Restless Kids Grew Up to Virtually Rule Your World—which profiles Microsoft founder Bill Gates, Cisco Systems CEO John Chambers, Oracle founder Larry Ellison, founder Jeff Bezos, and America Online founder Case—found that his difficulties grew, and changed, as his work neared publication. “It has been a significant challenge making this thing relevant and marketable,” he says. “The book feels like it’s three eras removed from relevance: the tech bubble bursting, the recession, and Sept. 11.” The book’s salvation, Leibovich says, is that it tries to be more history than journalism.

Using skills unofficially honed as the son of a psychiatrist and a social worker, Leibovich teased out the often similar forces that shaped his five subjects. With the exception of Ellison, “they’re all rich kids,” Leibovich notes—in stark contrast to Industrial Age giants such as John D. Rockefeller, Andrew Carnegie, and Henry Ford, all of whom suffered severe economic disadvantages in childhood that helped shape their adult ambitions. In addition, each of the five faced significant personal challenges as youngsters: Chambers from severe dyslexia, Gates and Bezos from bullies, Ellison from a troubled relationship with his father, and Case from feelings of inadequacy spurred by comparisons with his successful older brother.

Though the “great man” theory has been out of fashion with historians for more than a generation, Leibovich says that it “absolutely” fits the hi-tech sector, “largely because of the cults of personality that [the book’s subjects] and the media created,” he says. “At certain companies, the place could run fine without their CEO. But these five companies are all an intimate reflection of their CEOs’ ambitions, genius, and demons.”

Leibovich, 36, began his career at the Boston Phoenix in the early ’90s. In 1994, he joined the San Jose Mercury News, just as it was becoming the newspaper of record for Silicon Valley. (Leibovich says he had to overcome his “dumb-as-hell” attitude toward computers to cover the “human side” of the industry.) Three years later, he moved to the Post to cover Virginia’s booming—and later busting—technology corridor. Now that he’s finished with a lengthy Post project about MicroStrategy CEO Michael Saylor—who “embodies all the hype and hubris and possibilities and precariousness and hyperindulgence of the late ’90s,” Leibovich says—he will abandon the hi-tech beat to take a style-section slot covering politics.

Having reported the same subject for the better part of a decade, Leibovich says, “I have exhausted tech. It’s always a fascinating story, but it no longer interests me. I’m sick of these guys—the five in the book, but also the whole ilk. The era has become a cliché.” —Louis Jacobson