ONLINE BUSINESS

A Notorious Icon of the First Dotcom Bubble Returns

Phil Kaplan parodied the early dotcoms; now he's got his own, and it's one of the fastest growing private companies in America.
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Phil Kaplan isn't a forgotten footnote to the dotcom bust -- in case you were hoping. He's back and doing very well, thanks.

Kaplan became notorious in 2000 and 2001 chronicling the painful death-by-a-thousand-bursts of the dotcom bubble. The obscenely named website he founded and wrote, F***edcompany.com, was a derisive diary of the industry's misery, carrying news and rumors about Internet company layoffs and flame-outs. Insiders emailed Kaplan dispatches from deep in the carnage, and he made their tidbits a snarky read for a huge audience. He made money too, selling ads on the site, hawking branded merchandise, even charging for access to extra material. He appeared on the October 2001 cover of Inc. magazine, though he got less love from Inc.'s sister publication Fast Company, whose name he'd twisted in parody.

Adbrite, Kaplan's current company, is No. 34 on the 2008 Inc. 500 list. It's a Web-based service that makes it easy to place an online ad on any of the 76,000 or so content websites -- from tiny blogs to big publishers -- that have signed up to run Adbrite ads. It's a highly competitive market that titans like Google, Microsoft, and Yahoo want to dominate.

The idea for Adbrite grew out of F***edcompany.com (as a way to automate its ad sales) and seems to have been driven by the two forces that drive Kaplan: a short attention span that makes him constantly look beyond what he's doing and an overwhelming desire to make life a little easier on himself. Kaplan was on a short vacation at the shore when we caught up to him by phone.

Things have changed since the magazine last featured you.

The famous October 2001 cover story! It was unfortunate timing for everyone, because that issue came out right around the same time that 9/11 happened. Every magazine was a picture of Osama Bin Laden. Except Inc. was a picture of me, and the headline said "Don't Blame Me!" I loved it.

We have another connection: your father, Sam Kaplan, is a business partner with Inc. columnist Norm Brodsky. Was your dad an inspiration when you decided to launch a business?

I always heard him on the phone doing deals. And he always had a very flexible schedule, and that was always attractive to me.

We heard you like flexible hours.

That was one of my biggest goals – in fact, it was my only goal – when I started my own business. I was making $40,000 or whatever at my [Web development] job, and I said to myself, there's got to be a way to make the same amount of money but be able to sleep late. That didn't mean I didn't want to work a lot of hours. I just wanted to be able to wake up whenever I wanted to wake up. When I accomplished that goal, which was like three months after I set out, I threw away my alarm clock. That was a very happy moment of my life.

Was that the entrepreneurial itch -- you didn't like working for the man?

It's not so much that I didn't want to work for the man. It's that I sort of see something that I like and go after it, which is difficult when you work at a company. As an employee, you have this one task you need to work on.

So you started your own Web development company in 1999 and began witnessing the crazy excess as the dotcom bubble grew...

I originally just launched F***edcompany.com – I guess now you would call it a blog – where I would write about these companies that were going out of business. The biggest scoop was Enron. The snarkiest was Pets.com. If memory serves, "My dog needs food and my cat's box needs new litter. I know what I'll do -- I'll order Dog Chow and Fresh Step online from a sock puppet, then watch the dog starve and the cat shit around the house while I wait two weeks for it to be delivered."

How did Adbrite grow out of that?

I would get advertisers emailing me, saying "Hey, can I advertise on your site?" Let's say an ad was $100 dollars for five days. I would run to the bank and deposit the check and wait for it to clear, and run the ad, and make changes that they wanted to their ad over the course of it running. And I would have to provide them with all sorts of statistics: how many times their ad was shown, how many times it was clicked. And then at the end of the five days I would have to remember to remove the ads.

Initially, Adbrite was written to automate that process, where I could let advertisers buy ads without my having to do anything. I put a link that said, "Your Ad Here." Someone would click that, it would go to an order form where they could simply upload their ad, or type it in if it were text, put in their credit card number, and buy an ad right there. All I would have to do is click "approve." It was probably started in 2002 for my own sites, then I opened it up to the world in 2004. I kind of dropped everything else, raised money for Adbrite from Sequoia Capital in September 2004, and today there are 70,000 to 80,000 sites using Adbrite to manage their ad inventory.

How much did you raise?

Our first round was $4 million from Sequoia. In total, we have raised $35 million in three rounds from various investors, including Sequoia, who participated in each round.

Google's AdSense ads seem to be on every Web page out there. How do you compete?

Most publishers run ads from two or more ad networks. And if advertisers are spending 10 cents a click and getting 11 cents a click, they want all the traffic they can get. They want to be on all the ad networks.

You're also going after a big chunk of the Web that doesn't get discussed a lot -- adult sites?

Most ad networks support adult advertising. If you go to Google and search for some adult term, you'll see a lot of pornographic ads. We wanted to keep that out of Adbrite. We have brand advertisers who want to be sure they're never shown alongside adult content. So we removed adult from Adbrite and launched a site called Black Label Ads that's completely separate.

Supposedly that's a lucrative market.

For Adbrite, no, it's a very small piece of our business. We have about 120 employees, and maybe two people touch that side of it. There's certainly opportunity out there, but it's not something we've gone after.

In 2006, you stepped down as CEO of Abrite to be chairman and chief product officer, you and brought in Iggy Fanlo as CEO. Some happy critics said "Look! The guy who mocked Internet CEOs couldn't hack being one himself!"

People said that? Basically, I'm a product guy. I'm not really that interested in managing 120 people. When we got to about 60 or 70 people, I was finding myself unable to get into the weeds and work on products. I had to deal with finance and HR and management. I looked at it like Adbrite was losing a really good products guy.

Whatever happened to F***edcompany.com?

From the very beginning, I always used to tell everybody that F***edcompany.com had another two weeks left in it. It was pretty popular for about two years. I moved on, and the rest of the world moved on. I hired someone to update the site. Then one day I noticed the person hadn't updated it in like three months. I said, "Ok, this is probably a good time to shut it down."

It seems like we could use it again.

Now there are companies that aren't making money that seem like brilliant ideas. Things like Facebook and Twitter are super useful. Back in the old days, a company would have no revenue and no users and not provide any value to anybody.

As Adbrite gets established, are you trying to push F***edcompany.com farther down on your resume, put some distance between now and then?

No! I'm very proud of everything I've done. I think F***edcompany.com was awesome. I can't believe it happened. When I look back on all that stuff I'm impressed with myself.

Last updated: Aug 22, 2008




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