As far as HN proper, I don't dislike this community at all, particularly since dang took the reins. It's an interesting place and I've tried to contribute in good faith for many years now, besides just making fun of it.
I'm pretty sure Silicon Valley are quite well aware that privacy is an issue and a growing number of users are uncomfortable with the surveillance-as-a-service business model, but it pays the bills so why would they change? How can you create this demand so that the pro-privacy business model works?
I'm curious to see what you can make of the opportunity, if one even exists here.
I would call what I do 'impure trolling', since I run an actual business, and have given an earnest series of talks calling for regulations on mass surveillance.
Following in this earnest vein, I live a life of independence and fun, and would like to encourage young technical people to live that life too, rather than wasting their youth in pursuit of a one-in-ten-thousand shot at plutocracy.
The startup scene hasn't been content with "paying the bills". They've been chasing demand even when that demand doesn't bring actual money along with it. It's completely nuts, and maybe it should change a little.
I mean, you sort of imply that the pro-privacy business model doesn't work, but Pinboard is more profitable than Twitter. Does that mean profitability is no longer the measure of whether a business model "works"?
The folks at Basecamp (formerly 37signals) have been pretty consistent too at criticizing the Silicon Valley rhetoric, and their company is undeniably profitable. They write at https://signalvnoise.com and I also recommend their books.
It Just Works, and that's all it does, and that's all I need it to do.