I don't know why anyone ought to listen to Dave Winer (to pick one example from pseudo-random). The man can't give a hyperlink a meaningful title; this gives me little confidence that he actually thinks anything interesting about the Internet.
Seriously. The reason hypertext works is because you can associate meaningful words and phrases with other information. Consider how Ward's wiki still works; it forces you to make link titles describe the destination.
If, when writing a sentence like "I was talking to some person about some interesting subject", you think the proper place for your link is the word "talking", then get off the Internet, have a good think, and don't come back until you get it. Really. It's not irony; it's incompetence.