Would have rails taken off if he was equally open about his politics back then?
People's politics do often (but not always) change as they age.
[0] https://www.vice.com/en/article/basecamp-didnt-just-ban-poli...
I'm not sure DHH really held the same views back then, either. The "Overton Window" has moved over the last 20 years so openly bigoted and racist views are accepted in the discourse now.
Calling for ethnic cleansing is not a libertarian belief. It is a fascist belief. "Privately owned roads are a good idea" and "Let's round up all the gypsies" are not equivalently debatable ideas.