It takes root in posting really good content, at least for a while. You get your points up, get seen as a contributor, and then you start posting your own blog posts. Nothing explicitly an ad at first; you're just trying to get people to start thinking of your blog as something that usually has good reads, and that . Then you eventually post about a thing you made that you think the audience would want to buy, and, not exactly shockingly, they do!

By framing it using something like "My startup failed... again. An analysis," or "Just got the first few bites on my product, after years of trying," you let the audience escape the feeling of being advertised to despite the motive being entirely profit.

There was one user that was so good at this they were on the front page nearly every month of last year and they sold $60k worth in units because of it, never getting called out for what they were doing. To be generous to them, the content was good when it wasn't advertisements. You have to remember that what's popular on Hacker News on any given day will also circulate around a bunch of tech sites that are bad at coming up with their own content.

One person that I actually know built a complete business out of subtly using HN for advertising.

This takes root in even smaller ways, though. Like someone popping up in every thread that's remotely relevant to say, "Hey! We're building a product that does this at lazyfiveletternamedotio! Check it out, it seems like it fits your use-case." Sure, they'll get criticized, sometimes. But they'll also get bites. And when you're selling software as a service substitute for $600/mo, it doesn't take very many bites to make being criticized on Hacker News worth it. Doubly so when you're taking venture and need to up your numbers for the next round.