One of your points early on is that MySpace was the first Internet heavyweight to materialize outside the usual high-tech/Silicon Valley axis. In other words, it was the brainchild of marketing guys rather than geeks. Do you see this as the first of a new wave? Or is MySpace still the exception to the rule?

I really wanted to think it would be the beginning of a new wave. But I haven’t seen any evidence of that yet [laughs]. One reason is that the MySpace guys have found it technically much heavier going than they expected. In fact, they have fallen behind and not kept pace with the social-networking movement. So we have seen the potential repercussions of being a marketing-focused company.

But I think it will happen. Because the big media companies are investing a lot of time and expertise in this, and they will figure it out. Things like Hulu are beginning to be the next wave. The technology will have succeeded once it becomes to easy for people who are not technologists to use it.

So we’re waiting for Old Media to save the our bacon?

You do need money to launch a really big website. I mean, look at Twitter—they’re still barely keeping up with their growth.

I hadn’t read much before about Chris DeWolfe and Tom Anderson, and to be honest, I was taken aback by the sleaze level of their earlier enterprises. Essentially these guys were scam artists.

You know, I like to say that they were really good at imitation.

But hold on. At ResponseBase and Intermix, they were peddling spam, fraudulent e-books, and anti-wrinkle cream. They made a business of sneaking spyware onto people’s computers. You must have been aware of this stuff when you began your research.

I knew a tiny bit of it. But as I dug, it got richer and richer, and I was very pleased.

Did it surprise you?

It did surprise me. I thought, okay, whatever, they had sent out spam emails for one product. There were always rumors, things that had been hinted at in the past.

For me, there was a certain comedy in them selling the cheapo remote-control cars from China, or the miniature spy cameras. That’s just low-end retail. But the American flag cursor they persuaded people to download, which then planted spyware for banner ads on their computers—that’s actually illegal. And morally indefensible.

Yes. Particularly given the fact that they were jumping on the 9/11 bandwagon.

So what do you make of it all?

I hadn’t spent much time with people like this before, and it made me realize that this is what entrepreneurship is all about. These people throw stuff against the wall until something sticks. They have no way of knowing which of their crazy ideas will make it big. It’s the entrepreneurial spirit, which I have to admire. I probably couldn’t cut it in that world.

A related question. At one point in your book, venture capitalist David Carlick recalls his initial meeting with Richard Rosenblatt, who would become the CEO of MySpace corporate parent eUniverse. “I fell in love with the guy,” recalls Carlick. “He’s a reality distortion field.” Didn’t such reality-distortion specialists already wreak enough havoc during the first dot-com boom? Or is this just the nature of the entrepreneurial game?

I think it is the nature of the game. Carlick compares Rosenblatt to Steve Jobs. His basic point is that Steve Jobs is the ultimate reality distortion field (he didn’t invent that line, by the way). And it’s true. The greatest entrepreneurs are hucksters who have simply crossed the line into brilliance.

To a large degree, your book is about the mating dance between Old and New Media—with Rupert Murdoch dominating the dance floor. At this point, how does Murdoch look? Is he a swashbuckling visionary, or did he get sold a bill of goods?

James Marcus is the deputy editor of Harper’s Magazine. His next book, Glad to the Brink of Fear: A Portrait of Emerson in Eighteen Installments, will be published in 2015.