"One does not decide to be an entrepreneur," he writes in "Lucky or Smart: Secrets to an Entrepreneurial Life." "One is an entrepreneur. Those who decide to become entrepreneurs are making the first in a long line of bad business decisions."

Peabody can afford to pass such sweeping judgments. He personified the "slacker CEO" image that became the rage during the Internet bubble years of the late 1990s.

In this slender, 58-page memoir, he recalls some of the fawning articles that were written about him after he became a dot-com millionaire and warns other successful entrepreneurs to beware of a trap: "The number-one killer of startups is when entrepreneurs confuse 'being lucky' with 'being smart.' You must possess the humility to distinguish one from the other."

You might remember the stories: Peabody, a shaggy-haired guy who drove a beat-up Volkswagen Rabbit, rode the Internet revolution to wild riches by the age of 26. Rather than follow the pack to Silicon Valley, he based his company in Williams- town, a village of 6,000 tucked away in a corner of Massachusetts.

During a recent interview at his Manhattan loft, he acknowledges that one of the main reasons for writing the book was to describe the wrenching, 24-7 schedule required to launch a startup.

"I wanted to set the record straight," says Peabody, 33. "It seemed easy, but it wasn't."

Peabody acknowledges that the success of Tripod, the company he founded at Williams College a decade ago, was largely a product of luck. As an undergraduate, he wanted to launch an online service that would provide "real life" information to college students about practical subjects such as job searches and personal finance.

But the computer programmers he hired to build that online service came up with something else: a software program that allowed users to build their own Web pages and publish their views on the Internet. Peabody had no interest in or awareness of the potential of the self-publishing movement (this was well before the advent of Web logs, or "blogs"), but he soon recognized that this component was the most popular service of Tripod, so he latched onto it.

In 1997, Tripod attracted more than 1 million registered users. It wasn't profitable, as it hardly generated any revenue, but the size of membership was valuable. Peabody faced a choice: take the company public or sell to a bigger Internet company. In Bob Davis, the then-41-year-old CEO of Lycos, he found a grown-up who shared his view that the Internet would eventually self-select into a series of niches where like-minded consumers would surf.

"I was 25 or 26; I wasn't ready," he recalls. "I knew I couldn't play ball at the level Bob Davis could." He sold Tripod (including his own 7 percent stake) for $58 million, taking his payout in Lycos stock, the value of which subsequently grew tenfold.

By 2000, when the Internet bubble finally burst and many high-flying companies crashed, Peabody had sold most of his Lycos shares. He walked away a rich man, and his book, a meditation on the lessons he learned from the experience, attempts to define how much of his own success derived from luck, and how much grew out of his business acumen.

For the past four years, Peabody has been building his own venture capital funds through a company called Village Ventures. These funds, which are raised, managed and invested in smaller markets, such as Providence, R.I., and Boise, Ida., seek to identify business opportunities that get overlooked by the big funds from Boston and Silicon Valley.

Having grown from student entrepreneur to venture capitalist, Peabody laughs about the confused priorities of some of the entrepreneurs who approach him for money. Many insist that he sign an "NDA," or nondisclosure agreement, before they make their pitch for Peabody's financial backing.