"An excellent book could be written about this period, about how Dave changed the internet."<p>There may have been some interesting ideas coming out of his shop, but isn't this a little ridiculous? I don't think a single one of these products ever got any real traction, and, frankly, most of them were flops.<p>I was using Macs during this period. I tried the thing I think was called Radio: started it, it insisted on getting an email address, so I typed mine in. Not more than 10 minutes later I get a spam email from some clown who was handed my email address by Radio, which apparently broadcast it to other Radio users all over the world without asking permission. I deleted it from my machine and never looked at another piece of Winerware after that. But I kept up with comments about Userland stuff on the internet, and noticed a barrage of complaints about security, privacy, memory leaks, instability, and the infamous, irrational behavior of the CEO.
The thing I've never been able to get past with Winer's tech is that he is so married to hierarchical representation. I've always felt like my own thoughts are best expressed as graphs.<p>edit: I mean CS graphs; many-to-many; a child having multiple parents. I don't mean your basic mind-mapping graphical software, which very often also don't support representing graph data structures.
Been a while since I thought about Scripting.com. It was the first "blog" I really read. I thought I was so cutting edge: had a reader app on my Palm (Sony Clie) that I synced and could read offline. Good times.