I think of hipster as someone who follows (non mainstream) trends, goes to starbucks, loves Apple products and cannot live without Wifi. Not a hacker who builds it's own stuff and cares about privacy. But maybe the beard confuses people.
It's hard to define the term, but I think at the most basic level, "hipster" specifically refers to anyone who enjoys being alternative. "Goes to starbucks, loves Apple products and cannot live without Wifi" are common qualities of people who want to be hipsters but only because they think it's cool (and don't actually embrace an alternative lifestyle).
It's pretty funny because of the stereotype. On the other hand, it makes sense that someone dedicated to improving the state of privacy and personal data ownership lives on a boat. If he decides the government becomes too authoritarian, he just leaves with all his stuff. No go-bag needed because he has a go-house. Lay low in SEA near a wifi hotspot or something. You can't escape the reach of corporations, but he (and others) are working on it in the form of scuttlebutt.
Substack is awesome. I think he's very much a modern day instance of the old hacker ethos. He's so creative, too- I've really enjoyed some of his project ideas and presentations I've been fortunate to see.