> I'm sure a lot of their sales funnel is just nerds like us using Tailscale at home, and then bringing it to their employers.
Honestly, I don't know why this stopped being the dominant strategy. Matlab, Adobe, Solidworks, and many other tools used to be free for students. It's not hard to see how people working with certain software while in school translates to using that same software outside. The same is true for at home! You get frustrated with whatever BS thing your work has and then ask your boss if you can use X instead.
I think it stopped because they got too big. Becoming the de facto tool they figured they could charge students and hobbiests too. I'm pretty sure this just lead to more piracy and open source solutions. I mean Coca-Cola still advertises... they sure aren't doing it for brand recognition... everyone knows who they are (same with McDonalds!). They do it to associate feelings. These companies should still do those student and hobbiest versions for the same reasons. It prevents others from displacing you. Companies aren't going to complain about the price and pirate your stuff instead, they have the money. Only hobbiests and students do that stuff...
There is one problem... I've seen employees at certain places use personal accounts for business work. Worse, I've seen them do this despite the business already having seats! I don't know why this is going on, but maybe we should do a bit of peer pressure if we want to ensure we keep those free hobbiest licenses. Plus, it puts your business in a legally dubious area. Not likely to get sued, but it sure isn't legal...