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"Philip never was somebody who could take orders that well from anybody," acknowledges Leslie Kaplan. "So I knew that he would have to be in business for himself."

Butterflies
While still working at Think New Ideas, Kaplan spent his evenings writing a piece of E-commerce software called Startcommerce. "I was doing it with the intention of eventually being able to quit and just write software," he says. "And the day I sold the first copy [for $6,000], I quit my job. I figured this was a perfect time to start a development company where I would charge $200,000 for something that would otherwise cost $1 million." He started his new company, PK Interactive, in early 1999. It eventually employed four people and attracted clients that included Meade Paper and Toyota.

At that time Kaplan received what he says was his father's soundest advice. "I started PK Interactive with the intention of eventually hiring people and growing beyond just myself," Phil says. "But when I had more work than I was able to do and I needed to hire somebody, I told my father that I was nervous because I didn't have enough money to pay somebody. I mean, I had enough money to maybe pay somebody for the month, but of course that would be reliant on more revenue in order to keep paying this person." His father told him that if he couldn't keep one programmer employed, then he didn't deserve to be in business. "I thought that was good advice. I took it, and I did fine. I was out about six months on my own when I turned a profit," Phil says.

Recalling that time, Sam Kaplan says, "The concern of any entrepreneur is that you build for expansion, and then what if the expansion doesn't come? When the company is at the start-up level -- very small -- if you don't have confidence that you can keep people busy, then what's the point of building the business? And Philip wanted to build the business. He was very apprehensive in the beginning, which is odd for him. But he has an aversion to not making money. We entrepreneurs seem to be full of bravado, but inside there are butterflies, and Philip is no different in that regard."

But Phil -- or is he Pud at this moment? -- swears that money was not his primary reason for stepping out on his own. Instead, it all boiled down to the hands on the clock. "My main motivation for starting my own business -- and this is totally true -- was so that I could sleep late," he says, yawning. "The goal of being able to throw away my alarm clock looked a lot better to me."

As the year 1999 progressed, Phil became only more convinced that the Internet craze was here to go. "It all got to the height of ridiculousness," he says. That spring, in a key event that helped his thinking coalesce, he attended a party held by shopping site Boo.com. "Boo was the first really big dot-com disaster," Kaplan says. "They blew through like hundreds of millions in like a year. They used to do stupid shit like having these big parties. It was just the height of excess. But when you have millions in the bank, you don't think it's a big deal to buy drinks for everybody in New York City. They had this one party at a bar named Joy, gave out gift certificates, and then went out of business." (Boo.com has since been acquired and relaunched by new owners.)

Not long after that party, Kaplan found himself alone in the deserted city on Memorial Day weekend. With nothing better to do, he created a Web site as a lark. He named it FuckedCom- pany as a parody of Fast Company magazine (which, like Inc, is owned by Bertelsmann division G+J USA). The site tapped into the thriving E-mail grapevine through which dot-commers swapped gossip about their companies. "Internet people are always sending each other links, saying 'Peep this," says Aron Malkine. "And it would usually be silly Web ideas that were really trying to be serious. FuckedCompany is a commentary on everything like that."

After launching the site, Kaplan did what any self-respecting Web-preneur would do: he took a week's vacation in Brazil. But before he left, he E-mailed the new site's URL to six or so friends, who then sent their own E-mails flying.

The rest, as they say, is history. By the time Kaplan returned from Brazil, some 20,000 people had logged on to the site. Most were interested in playing its version of a "deadpool" game, in which participants won points by accurately picking which dot-coms would bite the dust first.

Within weeks of the site's launch, Seth Kaplan got a call from his brother. "Dude! You are never going to guess what," Phil said, according to Seth. "It just ballooned within weeks," says Seth.

"I Figured Out How to Make Money"

Late in 2000, Kaplan decided to go full-time with FuckedCompany and turn over PK Interactive to his employees. After conferring with his father, Kaplan left his employees with a three-month severance package and referred all his clients to them at the new company that they formed.

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