(Or how Phil Kaplan, founder of FuckedCompany, learned to stop worrying and love the dot-bomb)

Caroline Beddie had no idea what she was in for. Not a clue. The spunky 38-year-old had been a waitress at Ye Olde Kingshead, a tavern in Santa Monica, Calif., for more than a decade, and she thought she'd seen it all: the coiffed celebrities; the stargazers and wanna-bes; the surfers who consumed a little too much Bass Ale. But nothing could have prepared her for the night last January when Phil Kaplan, better known as "Pud," showed up. Kaplan is the 25-year-old founder of FuckedCompany.com, a Web site that for the past year and a half has chronicled the daily machinations of the dot-com bust. A few days before, as Kaplan prepared to leave his base in New York City, he alerted visitors to the site that he would be visiting L.A. and stopping in for a drink at the Kingshead. Did anyone want to join him?

You could say that again. "It was absolutely mobbed," Beddie laughs. "And they were all there to see him. He was like their local hero. They would ask in these discreet, hushed tones, 'Is that him? Is that Phil? Do you know which one he is?"

The Kingshead is no stranger to stars, says Beddie. Tom Cruise pops by every once in a while, and on the walls hang pictures of prior guests Rod Stewart, the band Oasis, President Reagan before he was President Reagan, Tom Hanks. "But this night," Beddie says, "everybody ignored the pictures because they were so desperate to meet this Philip person -- to build up the courage after a few pints to talk to this guy. All night long, it was 'Is that him? Is that him?' I just kept saying, 'He's that tall guy at the bar, wearing a denim suit, hanging out and talking to people and signing autographs.' I mean, people were waiting in line to meet him."

In the line was Kaplan's aunt, Marlen Mertz. She had wandered over to the Kingshead from her nearby home, hoping to get a moment with her nephew. "It was amazing," Mertz says, still slightly bemused by it all. "I felt like it was the Beatles! It was almost cultish. When I told people I was his aunt, I became famous, too!"

ENTREPRENEURIAL ADVISORY: This article contains frank language, ribald slang, and a prosperous dot-com, which some readers may find disturbing.

At the center of all of the brouhaha was Phil Kap- lan and his no-holds-barred Web site that, since its whimsical inception on Memorial Day weekend 2000, has detailed the tortuous ins and outs -- mostly outs -- of the dot-com debacle. As the site's own "What Is It?" page proclaims, FuckedCompany "has pretty much turned into the source for news about dot-com companies. Bad news, that is."

The site now attracts some 4 million unique visitors a month, according to Kaplan, and has attained a cultlike following among the pink-slipped or otherwise dot-com disenchanted. It has also become a must-browse for headhunters, journalists, and Internet analysts -- not to mention the just plain curious. For one, there's that name, which is nothing if not attention getting, as if daring one to indulge in a guilty pleasure. Even Kaplan's nom de Web, Pud, is obscene slang. "The site's name is so direct and in your face," says Anna Wheatley, editor of the AlleyCat News, a magazine that covers the business of New York City's Silicon Alley. "It's entertaining, if something of a gladiator sport. It's terrible that you're being entertained by carnage, a deathwatch. But what he has done so successfully is to make business into a form of entertainment. And Philip has turned himself into a personality, an entertainer. He is totally capturing the zeitgeist now. Totally! And I think he knows it."

Kaplan's 15 minutes of fame have been extended by the mass media. In the past year, he's been featured in the New York Post, the Washington Post, Rolling Stone, The Industry Standard, and New York magazine, to name but a few. Kaplan has also made TV appearances on CNN, MSNBC, and CBS's The Early Show, which hosted Kaplan last January after the Women.com site named him Internet Bachelor of the Year.

"FuckedCompany is a site for people in the trenches," says Kaplan. "It punishes the CEOs and the founders who have laid off so many people. The only people who don't like the site are the founders -- and, good, because they deserve it. All of the depressed, laid-off dot-commers love the site."

"Rock On, Pud"
FuckedCompany is also a solid business of its own. Kaplan brings in revenues from banner advertising and online sales of merchandise that includes FuckedCompany T-shirts, mouse pads, and coffee mugs. Kaplan also says he reels in some $90,000 a month from 1,200 subscribers, who pay to search through unfiltered tips about layoffs and barricaded doors at dot-coms. Kaplan estimates that he receives some 400 unsolicited tips a day -- often from programmers on the front lines. They're the nameless souls who played with Nerf guns, worried about their sites' "stickiness," and populated the cubicles of Internet start-ups. Today their tips -- often made anonymously with online pseudonyms like techdude, dottedeyes, and notagoy -- provide the core of FuckedCompany's database.

And Kaplan talks back to them, which is key to FuckedCompany's mystique, not to mention its sheer drawing power. He regularly starts message threads on his site, and he also E-mails 65,000 of his fans a free newsletter -- signed by his alter ego, Pud -- that has become increasingly full of what Kaplan calls "personal stuff." On May 29, for example, Pud wrote, "Today is fuckedcompany's 1-year anniversary! Woohoo! Hope everyone had a good Memorial Day. As for me, I woke up at around 3:00 pm, watched TV for a few hours, ordered Chinese delivery which never came, just finished about a million bowls of raisin bran, still wearing my bathrobe, ready for sleep again. Okay so Thursday night, I went on a blind date. I was all excited cuz I hadn't been outside in weeks, recovering from strep throat and just being a loser in general." After describing the disastrous date, in which he was "coughing all over the place, sweating, spilling crap on myself, trying to act normal," Kaplan signs off, "i will forever suck. anyway ... rock ... on, pud."

"The site's name is so direct and in your face. It's entertaining, if something of a gladiator sport. It's terrible that you're being entertained by carnage, a deathwatch. But what he has done so successfully is to make business into a form of entertainment. And Philip has turned himself into a personality. He is totally capturing the zeitgeist now."

--Anna Wheatley, editor of Alleycat News

Kaplan's use of online forum software and E-mail newsletters harks back to the early days of the Web, observes Allison Hemming, founder of the Hired Guns, a consulting firm in New York City. "Community-driven content is so cost-effective," she says. "Phil is utilizing true economies of scale. And he has captured the true spirit of the Web. His site is a real model for how to use community-driven content."

One thing is for sure: it works. Consider the math. At Kap- lan's current rate, he will bring in some $1 million a year from his "hot tips" subscription list alone, not to mention the less predictable but recurring revenues he receives from advertising and merchandise sales. Not bad when you consider that his overhead basically comprises one full-time assistant and a portion of his rent -- Kaplan's Manhattan loft office doubles as his apartment. "In covering the demise of the dot-coms, Phil has succeeded in creating a viable Internet company," observes Geoffrey Kloske, the Simon & Schuster editor who in May commissioned a book from Kaplan tentatively titled F'd Companies: Spectacular Dot-Com Flameouts. "And he is making money. He has succeeded where so many others have failed. Phil is viable and profitable, and I wish" -- and here Kloske pauses -- "I wish I owned shares in Phil."

"This Is a Joke!"
In retrospect, it would seem that Kaplan and his fellow FC-ers were some of the only people in America who were not taken in by the dot-com hype. Kaplan saw through it as early as April 1998, when he moved to New York City to work as a technical producer for Think New Ideas, a Web-design firm. There, working on the Avon.com site, he began to realize just how fragile -- and transitory -- the dot-com craze was. "We built a Web site in three to four months, and Avon paid about $1 million for it. I remember the invoice," Kaplan recounts. "Money was just being thrown around. I knew it was not going to last. Meanwhile, all the programmers were sitting around in cubicles, saying, 'This is a joke! How the fuck is this being sold for $3 million?"

Kaplan's father and business mentor, Sam Kaplan, a self-described "serial entrepreneur" who is currently a partner in CitiStorage Inc., in Brooklyn, N.Y., remembers that time clearly. "Philip didn't mind being part of it, but he saw it for what it was," Sam recalls. "Most people thought it was reality, but he thought it was fantasy." In fact, when Phil set up a retirement account for himself during the height of the dot-com boom, he avoided tech stocks. Sam recounts, "He said, 'No, don't invest in those stocks, because this thing can't last.' He realized that people were putting out $1-million contracts for jobs that could be done by two high school kids in a weekend."

It was a view shared by many who did the actual labor behind the Web-site explosion, writing code, designing pages, editing content. Aron Malkine, one of Kaplan's early employees and now a freelance programmer, was one of those people. "It was pretty obvious that the bubble was going to burst," he says. "There were a lot of really silly ideas being seen as something real." Another skeptic was Nick Baily, an old friend of Kaplan's and a former dot-com laborer. "I was saying, 'No way can we be making money,' but we had millions of dollars in financing," he says. "You keep it to yourself; you talk about it over a beer with your friends. But a lot of us were part of the collective delusion."

For the folks in the dot-com trenches, FuckedCompany touched a nerve. "People who went to Phil's Web site said, 'Wait a minute. I'm not the only one who thinks this is crazy," Baily says.

So Phil Kaplan -- or is it Pud? -- became the man of the moment. "Phil is the geek sex symbol," giggles Tracy Castelli, a director of creative services for Popsmack, a Los Angeles online-advertising firm. "This whole segment was ripe for an angry young man. Every generation has an angry young man, and he is ours."

Sometimes it can be hard to separate Kap- lan from Pud -- or to know which one you're talking with. "His Pud persona is this geeky guy," says Phil's mother, Leslie Kaplan, a partner at the Washington, D.C., law firm of Dickstein Shapiro Morin & Oshinsky. "Some people might look at Phil as a geek, but he doesn't think he is one. He thinks he's quite cool, but he writes Pud as if he is a geek."

"Pud is a character," agrees Bonnie Halper, a New York City headhunter. "He knows it, and he works it. I think he has the most fun at being an Internet star. It's almost like it's a parody of itself -- which is what is so brilliant about it. He parodies geek chic. And he looks, dresses, and lives the part."

"It's not so much me as what I represent," Kaplan says as he lopes across his loft to answer the telephone. "I'm a 25-year-old-programmer who lives in New York City and is somewhat cynical. This is what my life is like."

Sam Kaplan suggests that Pud's geekiness is far more orchestrated -- even more calculated -- than Phil's "Hey, dude, this is cool" nonchalance might suggest. "This is Philip's moment in time, and he knows it," Sam says. "Part of his persona is that he is this lucky, geeky kid -- that he's making it up as he goes along. But from a business point of view, that's not the case. There is nothing accidental that he does with regards to FuckedCompany. Nothing. I'm talking down to where things go on the page, to what he says, how he says it, what he promotes."

Adds Phil's older brother, Seth, "Philip would have made a great chess player because he's always thinking three or four moves ahead."

"There is Pud, his persona, and there is Philip," Sam says, laughing. "They're not always the same. But speaking as a father, I love them both."

"An Independence Thing"
To get to FuckedCompany Central -- housed on Manhattan's West 31st Street -- you must first negotiate a scary elevator that creaks precariously to the seventh floor. (Kaplan, in fact, has been known to store water and a sandwich above the elevator just in case it breaks down.) On a steamy summer day, gangly Kaplan -- he's six foot four -- is stretching his legs, eyeing a half-empty beer bottle on the table, and ignoring a plastic cup filled with an unidentifiable pink liquid as he tells his story.

Kaplan grew up in Chevy Chase, Md., during the late '70s and '80s. He was the second of three boys and an admirer of shock jock Howard Stern -- "He'll talk about anything, anything." But Kaplan also was a fan of his entrepreneur dad. "Ever since I was a little kid, I always said that I wanted to do what my dad did -- even though I didn't know exactly what he did," Kaplan recalls. "He goes into businesses, fixes them, and sells them. Part of the deal was that I knew he made his own hours. I knew it was pretty cool, so I was always interested.

"My father just seemed too smart to work for anybody," Kap- lan continues. "I don't see myself like that -- well, maybe I do. It's not a smart thing or an intelligence thing, it's just like an independence thing." As he talks, Kaplan's eyes twitch in a gesture that connotes more restlessness and speed than nervousness -- but definitely jibes with the fact that, as a boy, Kaplan took Ritalin, was arrested once (for "attempted destruction of private property, involving a slingshot," he says), and was expelled from school twice. "I just hated all school," he says with a shrug.

In fact, Kaplan recently attempted to obtain his mug shots from the slingshot incident. "I thought that it would be really cool to have those," he says. "But they wouldn't let me, because I was a juvenile at the time, and they couldn't release the records. But I would love to use those pictures for your story. It would be like the O.J. cover -- remember his mug shot? Cool." ("That is Philip's persona," cautions his father when told how much his son likes to talk about his arrest. "That's Phil marketing Phil.")

As a boy Phil also had firsthand contact with several business builders. Sam belonged to the YPO -- the Young Presidents' Organization -- a group dedicated to creating leaders through education, recounts Phil's mother. "They often had family events, so the boys grew up knowing people who were the presidents of many of the businesses in town, from stores to travel agencies to service companies, manufacturers," she says. "Other children might grow up knowing colleagues of their father, but the boys grew up knowing presidents of high-profile businesses in town."

Phil also had an early love affair with the computer and often stayed up all night. "If you wanted to punish most kids, you took away the television," Leslie says. "But if you wanted to discipline Philip, you took away the computer. There were times when I wanted to put the computer in the trunk of my car when I went off to work. We used to call it computer addiction."

The addiction translated into what was, in many ways, a precursor of FuckedCompany. While in high school, Phil ran an online bulletin board with some 400 members. "In those days everything was dial-up through the modem," Sam remembers. "His door was across from ours, and all night long we would hear people dialing up through the modem."

"Well," Phil suggests, "it's more fun to be involved in an online community if you started it and you have ultimate control over it. That's one of the reasons that I built my bulletin boards in high school."

Phil's exposure to the more traditional working world also started when he was a young teenager. He held a series of summer and after-school jobs, always moving on when he felt he had learned all that there was to know about the business at hand. And he used the proceeds to rent office space from his father to house a music studio. "Music is my art," he says.

"Phil is the geek sex symbol. This whole segment was ripe for an angry young man. Every generation has an angry young man, and he is ours."

--Tracy Castelli of Popsmack, a Los Angeles online-advertising firm

In 1997, after graduating from Syracuse University with a degree in information management and technology, Kaplan joined Booz-Allen & Hamilton Inc. in McLean, Va., as a senior consultant. There his independence was readily apparent. "I really did see the entrepreneurial side of him," recalls Karen Base, then a colleague of Kaplan's. "His big tag line was, 'Meanwhile, we could be doing this.' He was always multitasking and thinking of better ways to do things. If I could quote Phil, it would be 'Meanwhile."

The following year, Kaplan moved to New York to pursue his music career -- playing the drums is his passion -- and joined Think New Ideas. "As an employee, it was not unusual for me to be reprimanded," he says. "One time I fixed a program because there was a bug, and even though I fixed it correctly, everybody yelled at me. So I was like, 'Whatever ...."

That's when Kaplan seriously considered working for himself. "I have a lot of different skills -- writing, programming, different ideas, financing, accounting," he explains. "At most companies you have a job title, and if you do something outside your job title, then you're seen as stepping on other people's toes. But now that I have my own business, I'm allowed to step on whoever's toes that I want to!"

"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."

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.

In explaining his decision to concentrate solely on FuckedCompany, Kaplan says, "I have a lot of ideas, so I get in over my head a lot. I mean, at one point I had PK Interactive going, I had FuckedCompany going, and I was in a band. It was sort of a roll of the dice which one should I really focus on more. I had to make a decision, and that kind of thing happens to me a lot."

Since then, Kaplan has hired one full-time assistant, who answers the several hundred E-mail messages he receives each day and basically tries to organize Kaplan and keep his life running. Kaplan has also brought in a partner. "It's just not something I'm really ready to talk about," he says.

This past March, Kaplan launched his subscription service. "I figured out how to make money," he says. "I knew what I had was really valuable because people kept asking me, 'Do you have any information on this company? Do you have any information on that company?' When you get 100 E-mails like that a day, and you have that information, you realize that you can start selling it. An old-fashioned Web site would have just made it available for free. It's useful information just packaged in a rude way, but if you need to use it for business purposes and you can get past the rudeness, then you'll find its value."

As for advertising, "it's totally all over the place," Kaplan says. The site used to make a lot of money on advertising -- until the online-ad market fell through the floor. So for a while there was no way Kaplan could use one month's ad revenues to predict what the next month's would be. Then late last spring, he devised a plan that automated the ad-buying process. A new page on the site now lets advertisers and agencies place an ad on FuckedCompany and pay with a credit card. "I noticed that we were still selling tons of T-shirts and tons of subscriptions, and I think that the reason was that you could just use your credit card, and it would be done," Kaplan says. "And as soon as we did that with ads, I started getting advertising again. Instead of hiring an ad salesperson, I was like, 'This is stupid. Why don't I just make a thing where you can type in your credit card?' So now it sits there by itself and does the job of a person."

One thing is for sure: Kaplan's alarm clock is gone for good. "Sometimes I spend literally all day and all night on the site," he says. "And then sometimes I just spend an hour or two." Updating the front page takes maybe two hours. That's a sort of daily minimum for Kaplan, but he quickly adds, "I don't really look at it as work. I'm so into what I'm doing, I can't put it down."

Some in the dot-com industry question how long FuckedCompany's allure will last, given that the Internet bust is starting to feel like yesterday's news. Will the site's fans become inured to its relentless litany of bad tidings, and will FuckedCompany lose its cachet? Kaplan indicates that so far, the site has outlasted even his own original projections. "I've been saying 'another two weeks' for the past year. It has definitely confounded my expectations," he says. "You tell me: When are Internet businesses going to stop going out of business? Well, the answer is never."

Furthermore, he suggests that the site has filled a niche that no one else can occupy. "I figure companies will never stop going out of business, so I figure my company is OK," he says. "I mean, layoffs stopped being news six months ago, and I have more traffic and more subscribers than ever, so ..."

As for future plans -- well, let's put it this way: Philip Kaplan is considerably less forthcoming than Pud. "Yeah, I have a lot of things that I am working on, but I can't say," he hedges, smiling. Kaplan does acknowledge, however, that he's "working on some new sites" that could be linked to FuckedCompany.

One thing does seem likely to hang in there: the site's awful -- or, depending on your point of view, wonderful -- name. At a FuckedCompany party hosted by Kaplan this past July at San Francisco's Cloud 9 Motel (it's actually a bar and nightclub), Max Young, Cloud 9's owner, introduced his father, Bob, to Kaplan. Bob Young is a retired TV sales executive who now works as a media consultant and is a big fan of Kaplan's site. At age 67, he was easily the oldest guy at the party. "I introduced myself to Phil," Young recounts. "I told him, 'I love the site, and I will tell you why: it's a great source.' Phil said, 'Great.' He looked around the room and said, 'There just aren't enough women here.' And I said, 'In that case, maybe you should change the name of the site!' And he just smiled and laughed. You could see the twinkle in his eye."

Change the name of the site?

Not a chance, dude.

Not a fucking chance.

Gay Jervey is a freelance writer living in New York City.

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