SAN FRANCISCO — It's Monday morning at an online-advertising conference, and the chief executive of AdBrite Inc. is talking about repurchase rates and average per-click costs. But he's seriously distracted by the busty models serving beer in the booth next door.
At the first opportunity -- after getting through his sales pitch -- he reaches over for a plastic cup of Amstel Light.
Potential clients might recoil at the sight of a CEO behaving this way before lunch. But those who recognize Philip J. Kaplan would be disappointed if he didn't. Some drop by just to pay homage to the Internet's preeminent bad boy.
"I had to come talk to you because you're the creator of the best website ever," says Kevin O'Barr, a vice president for an online marketing company.
He's not talking about AdBrite. He's talking about Kaplan's other business, a website that made him one of the few people to get both rich and famous from the Internet crash of 2000 -- a site with an obscene name that is a mocking twist on that of the new-media magazine Fast Company.
Five years ago this month, as a 24-year-old Web designer, Kaplan created what quickly became the Internet industry's wailing wall, a site that used leaked information and ruthless commentary to chronicle the disintegration of hundreds of Internet companies.
To laid-off workers, he was a hero. To employers, he was a curse.
Now, instead of tearing down companies, Kaplan -- at 29 -- is building one of his own.
He persuaded Sequoia Capital, the blue-chip Silicon Valley venture capital firm that backed such companies as Google Inc. and Apple Computer Inc., to invest $4 million in his method of placing ads on websites. He moved from New York City to San Francisco with dreams of turning AdBrite into the next billion-dollar company.
In some ways, Kaplan's story is the story of the Internet: Both worked through their youthful indiscretions and are coming back in a more sure-footed, sober way. After 10 years of booms and busts, the Internet has proved itself a medium capable of generating billions of dollars from the kinds of ads Kaplan is selling.
"C-E-O," says Web entrepreneur Greg Tseng, as he approaches Kaplan's booth and shakes his nametag. "Man, you're all legit now."
Legitimacy is something Kaplan is still coming to terms with. He says taking venture capital funding and trying to turn his tiny company into an Internet giant may be the most "punk" thing he's ever tried.
"I knew that if I concentrated on AdBrite I could probably make a big company out of it," he wrote in a March e-mail to followers of his old site, which he calls "FC" to get past spam filters.
"But leave my cushy life in NYC? No more waking up at noon, updating FC for an hour, and spending the rest of the day cashing FC checks and watching porn? ... It was a hard decision, but, like, I'm a man now. 29!"
Kaplan doesn't need to look too deeply into his childhood in Chevy Chase, Md., to find the irreverence that seeded FC. With a habit of cutting school to skateboard, he was often in the principal's office. He was expelled in fourth grade for getting in trouble too often and again in eighth grade for constantly skipping class. Slingshot target practice on the roof of a parking structure earned him a day in jail.
Six feet 4, rail-thin and into heavy-metal music, Kaplan says he had trouble making many friends in high school. But he loved computer programming and found camaraderie online.
His parents bought him a Hyundai personal computer and a phone line, and he spent most of his bar mitzvah money on a faster modem. He would often stay online until 3 a.m. or 4 a.m., with a towel stuffed under the door so his mother couldn't see the light from his monitor.
He began running his own online bulletin board, a messaging system that predated the World Wide Web, and it quickly became a popular place for finding the latest pirated game and other software, swiped credit card numbers and directions for making free phone calls. It was a closed community with 300 members, and he was the leader.
He found his stride at Syracuse University, where he made friends, played drums in a band and taught programming courses. He graduated cum laude with a degree in information management and technology and landed a job with a management consulting firm in Virginia, creating computer programs for running businesses.
A year later, on a whim, he moved to Manhattan to try his hand at a career producing music. He lived with his grandmother. To pay the bills, he worked at a Web design firm.
It was 1998, and he quickly got his first taste of how overheated the Internet business was becoming. One time, he was asked by his bosses to estimate how much to charge for a project. It was easy work, so he said $200. By the time the bid got to the client, his bosses had tacked on two zeros: $20,000. The client signed the contract.