Additionally, DHH somewhat regularly blogs about political things. While I understand it's his "personal" blog, can you really have a personal blog separate from work when you're the CTO of the company and the creator of Rails?
I guess my take is that if you want to have a truly personal blog or social media channels, it should be as anonymized as possible. (Which has pros and cons.) Certainly, there are a ton of things I wouldn't write on a public channel even if I weren't technically violating any company policy because they would bite me.
When I was an analyst, I would absolutely not write anything about a CxO that differed from what I would put in a research report.