I don't think it would work. Conan is a funny guy but almost all his comedy is based on mainstream popular culture punchline. On the Internet you're dealing with an audience who has largely turned away from the mainstream spoon fed world to search out their own interests. He would have to drastically revamp his routine because, chances are, most of that mainstream spoon fed audience is going to watch whatever is on broadcast TV at 11:35. This nicely explains the success of people like Jay Leno and David Letterman who haven't delivered a new joke in the last decade that didn't involve simply updating names/places/event to fit their classic routine of pop culture humor. It's not quite the same as the silent film era stars who couldn't make it in talkies but I don't think it's entirely different either. It's just a different skill set and a big transition to make for someone who's been doing basically the same exact show every night for 15 years.