Douglas Edwards: And it wasn’t just advertising for lobsters. Ryan quickly understood the opportunity for arbitrage. Amazon had an affiliate program where if you sent someone to Amazon and they bought a book, Amazon would pay you. So Ryan began taking ads out on Google not just for lobsters, but for books that would link to his Amazon affiliate page, where he would collect commissions. And of course in the same way he was using Amazon to generate revenue, he began linking to adult sites that were paying for traffic.

Ryan Bartholomew: I just couldn’t make much money on the lobsters, so in 2001 I ended up selling that company and ended up focusing on porn basically. Google allowed you to bid on adult keywords and run traffic to the porn affiliate programs, which get people to give their credit card and sign up for a free trial and all that stuff. It was a really simple business model: I would bid on any sex-related keyword that I could get, traffic was cheap—especially for the obscure stuff—and I would send it to a page that was nothing but text links. It would break down whatever their interest was, any kind of fetish, and then they would click it and it would take them to a porn site targeted to that interest. At one point there must have been forty or fifty affiliate programs for everything under the sun.

Ray Sidney: I got burnt-out. I was not feeling very productive. I thought, You know what? I need to get away.

Charlie Ayers: A lot of the early-timers were looking at, like, How much does this island cost? There was a lot of distraction.

Ray Sidney: Originally I thought, You know what? I just need to take a month or two off, and then I’ll kind of get that fire back in my belly. And that never happened. I left in March of 2003.