The world likes anodyne. Not every individual, but as a whole.
Express a different opinion, do something different, and while you may have a few ardent fans/viewers/users/whatever, you're most often dismissed by the masses.
It's like the actor who does "one for them, one for me" where "them" is basically $$$. They're raging when they do the film they want to do for themselves, in a small way, and accept that it may not be as popular.
I think some architects might almost do the same, except it may not even be on a project by project basis. I'm not familiar enough with Tom's work, but perhaps there are times when he built a green he wanted to do, but capitulated slightly on some other feature somewhere. You can call it pushing the boundaries, but it's almost the same thing to me - different developers will have different limits.