I admit, I'm a skeptic. While I think chatroulette is brilliant in its simplicity, very much like Google was when it came out, the similarities stop there. I'm a big believer in serendipity, but the media buzz around it -- including the recent Ben Folds story -- has to taper off. Will the chatroulette guy be able to capitalize on all the fame and make some money? Possibly, but I think the money will come from Russia, not the US. I've been wrong before -- and plenty of people have argued with me on this point -- but I think that first, the barriers to entry are far too low to make this worth a substantial investment, second, the user interface doesn't make for very scalable marketing efforts (it's event more one-to-one marketing that face-to-face marketing!), and last but not least, the rather, um, colorful content limits their potential advertising customers.
You can read more of my and others' thoughts on chatroulette in BusinessWeek.