I seem to recall reading that Tew spent up to 20% of his targeted million dollars on PR[1]. Which would suggest that he had a very good understanding of page views being the important ingredient, a good story for traditional media being important (more so at the time) to get there, and more faith in what he was doing than anyone else that had the idea of creating a pure web page billboard.

[1]IIRC it was discussed in Paul Carr's Bringing Nothing to the Party, which isn't exactly complimentary about Tew

From an article in 2006:

"His friends and family paid the first $1,000 dollars, which he spent on a press release. That small publicity gave his site more traffic, which in turn persuaded more advertisers to have faith."

Source: http://news.bbc.co.uk/1/hi/magazine/4585026.stm

I remember from the TV news coverage he talked about how he'd sent that press release out to hundreds of news outlets. So I feel he (in part at least) made his own luck on this one.

Thousands of people send their press releases out every day, and most of them are never seen again. I stand by my assertion that it was largely a matter of luck, and while Tew no doubt knew he needed publicity, he had no reliably repeatable way of getting it. He was very fortunate with a dumb idea that fit someone's need for a good story at the time. There are thousands, maybe millions, of other dumb ideas that would make equally good stories but are not picked up. Statistically, it would indeed have been a better move for Tew to take the money and sit on it, just as it is a better move for a lottery player to save their $2. But it's certainly a lot more fun to gamble it. And unlike a lottery winner, in business if you win with a dumb idea, you not only profit, you look like some kind of savant.