Jeff, I don't know if what your dealing with is necessarily a generation gap, as much as it might be a gap in thought process, unless I completely misunderstood you. It feels like creative, young people should be the kinds interested in experimenting in new media, but I don't think that's always the case, at least in terms of what I have observed in my peers. Even those who have an interest in using Internet / new media as a creative medium, I'm not sure many of them know how to use it, or even approach the concept. I think the bigger issue is that we are all still so used to having the long standing technology and the preexisting community, and not needing to build it from the ground up. For example, one doesn't need to invent language, paper, the printing press, book stores, advertising and distribution models to write a novel. We aren't even conditioned to consider all the steps involved. However, I will admit that age is an issue in all of this, because younger people have an easier time reconditioning themselves.
These are just things this episode made me think about, off the top of my head. Again, I apologize if I misread your thoughts, and in the interest of full discretion, I'm a 24 year old undergrad at a rather small art college on the coast of Massachusetts and besides that I've spent a couple years amongst creative types in the Minneapolis / St Paul area. So, despite my broad statements, my cultural view is admittedly small.
On an unrelated note, I want you to know that I love and listen to all of the earwolf shows. It gets difficult, being stuck in my own head all day, and these shows keep me sane when I'm up the entire night creating art. Not to mention how inspiring it is, listening to hours of creative content. So, thank you.