I am going to take the opposing side of HN's groupthink and tell why I don't like that this guy is celebrated as a hero.
I haven't checked since a while but a long time ago when I tried to sign up to his site it was a showcase of dark patterns. What I specifically remember is that it sucked in all my data on a sign up form before telling me that I actually have to pay for access. I specifically checked every square inch of the opening site beforehand to see if it's a paid system. But it was filled to the rim with all the other usual dishonest marketing psychology bullshit too.
Usually it's best to avoid anybody who does any business with "digital nomad" in its description. So many hustlers preying on clueless people who are sucked into the promise of easily setting up an online passive income while travelling the world. Coaches, masterminds and paid-for online communities are the worst: newcomers pay access to people who are either essentially in the same shoes as themselves or are only part of the community to make a profit out of it. Obviously the ones who are willing to pay for this (and fall for the above described dark patterns) are the ones who want to get value out of it, not the ones who can provide. Why would any serious "digital nomad" pay to be part of such a community?
Also the original nomad list site was like a distillation of everything that's wrong with the lean startup ideology. The content was not only thin, it actually looked like it was totally made up. Whenever I saw someone link it as some authority on a location I always wondered whether anybody who has ever been to that place had any input on it. But it didn't matter, it was sleek and easy to digest so it took off. And then could be used as a traffic source for the other ventures under the same umbrella.
So the guy is now making half a million a year based on a site spreading completely useless and misleading information and riding the hope of a better life of newb digital nomads. Yes I am bitter that I am not his position. But I am also bitter that this is the kind of business practice that makes money nowadays.