I agree, I think DHH's statements were bizarre. They seemed to assume a sort of binary idea of "professional." You were either an anal retentive, by the book pedantic clock puncher or you were a fun loving rock star. The truth is there's a wide gamut and I think it's great for people to be "professional" without going to some sort of IBM-style extreme.
Times change. IBM-style "professional" is not the "anal retentive, by the book pedantic clock puncher" you might think. I worked there over 10 years ago, and we had no written dress code, flex-time scheduling, remote work, etc. The building I worked in had a 9 hole putt-putt course outside it, with foosball tables in a couple of the stairway landings.
Interesting how long we can hold on to perceptions from the past, even when they've been wrong for over a decade.
(I'm not implying that I'm disagreeing with you, in fact I think this shows that even what people think of as "pedantic clock puncher" and "fun loving rock star" from the outside is often very different on the inside.