First commit on https://github.com/shoes/shoes-deprecated.git predates that by about a year. Might not be the first time he'd given that talk, of course, but I always thought of _why and DHH as being at totally different ends of the ruby community.
This would pretty much be true. While DHH's claim is to Rails, I wouldn't say he was really a Ruby community guy. Where _why was specifically about Ruby, and non-commercially aspiring.