I wouldn't hire Dave Winer in a startup because he is an internet legend and I would assume he was very expensive.
Part of his salary would probably have to go on the marketing account but I'm sure there are wiser ways to spend that money in a startup.
I would be more OK with having him in a technical advisory role or something similar. That would give me most of the publicity value at a much lower price. (I would then of course also make sure his experience was utilized to the fullest extent possible, probably as a mentor to the tech team.)
Part of his salary would probably have to go on the marketing account but I'm sure there are wiser ways to spend that money in a startup.
I would be more OK with having him in a technical advisory role or something similar. That would give me most of the publicity value at a much lower price. (I would then of course also make sure his experience was utilized to the fullest extent possible, probably as a mentor to the tech team.)
Not sure he would like that, though.