Lucky or Smart

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It is for just this reason that I harbor a tremendous amount of guilt about my place in entrepreneurial culture. I fear that perhaps thousands of well-intentioned people wasted hundreds of thousands of hours pursuing entrepreneurial projects in part because of what they read in the press about me. I created a sort of playboy persona for myself as the CEO of Tripod. Pictures of me skiing, mountain biking, drinking beer, skateboarding in the office, and attending meetings in shorts, Birkenstocks, and a baseball cap graced several major media outlets. From Forbes to ABC's Nightline, from BusinessWeek to People, from MTV to Spin, the media broadcast images of me doing just about everything but working.

I absolutely, completely, 100% sold myself to the media to promote Tripod. Together, we created this image of the Slacker CEO: an athletic, shaggy-haired, perpetually mellow 24-year-old making millions while barely lifting a finger.

This image was broadcast not just in the United States but also to most of Europe. In five days during the summer of 1999, I jetted from Madrid to Milan, to Hamburg, to Paris, and finally to London, attending launch parties for Tripod Europe, staying in first-class hotels, and internationalizing the Slacker CEO myth of which I had become the archetypal example.

Hell, who wouldn't want to be an entrepreneur? I was a rock star. And I was the only person who knew it wasn't true. Friends would ask me, "What's it like to be a famous international Internet CEO?" "I'm not a famous international Internet CEO," I would answer. "But I play one on TV."

Working with the media was the most important job I had at Tripod. Period. Twenty-four-year-old Bo Peabody, with his hip Internet company in the mountains, was a perfectly packaged pied piper for the story of the decade. I was not only Tripod's poster child, I was shilling the whole goddamn Internet. And when it came to promoting these two things, the only self-respecting thing I ever did was turn down an interview on Montel. How noble.

I've often kidded that 90 percent of Tripod's value was in the amount of press we received in such a concentrated period of time. Sitting at a board meeting, lamenting our anemic revenue, I once joked to the board of directors that rather than actually running ads on the Tripod site, I'd sell potential advertising customers the opportunity that I might mention them in an article or wear their logo on my baseball cap. The board didn't laugh. They asked me to look into whether or not this plan was possible.

A lot was left out of all those articles. The hundred-hour workweeks. The anxiety attacks. The crashed cars and missed planes. The times I had to tell colleagues that we couldn't make payroll. The years of a $12,000 salary. Night after night after night of pasta dinners and stress-relieving Advil "cocktails." The countless meetings with absolute assholes who had no interest in learning about the Internet, the single most significant business innovation of their lifetimes. Pleading to venture capitalists for financing. Firing perfectly pleasant people when they didn't perform. In the late nineties, this reality did not sell newspapers and magazines. Baseball caps and Birkenstocks did.

Had I actually begun to believe what was being said about me in the press, I would never have sold Tripod when I did. I would have reasoned, instead, that I was in fact a genius, and that I should take complete credit for the great things happening to my company. Never mind that Tripod had little revenue, no profits, and an unproven business model; we should take this horse public! "Yeah," I could have said, "I am smart, not lucky, and I can defy economic gravity. I am in control!" Wrong. Tripod was all hat and no cattle. Had we taken it public, we would most likely have failed, and everyone, including many unsuspecting individual in-vestors, would have lost a lot of money.

I was not, however, completely immune to the media frenzy. Following the sale of Tripod to Lycos, what personal money I did not invest in bonds or real estate I invested in more than 20 Internet start-ups. Only five of these companies are still in business. The others are gone, along with a few million of my dollars.

The quickest way to tank your company is to believe what you read in the press, especially if it happens to be about you. The vast majority of journalists are not interested in covering what is actually happening. They are interested in covering what they think people want to think is actually happening. Everything is sensationalized. In 1999 it was sensationalized on the positive side, and in 2002 it was sensationalized on the negative side. It's never exactly accurate. As it turns out, accuracy can be quite boring. And quite boring does not sell newspapers and magazines.

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