Tailscale is free for personal use.

I set up Tailscale for personal use a couple years ago (shortly after the general availability announcement). I was blown away by how easy it was so set up, and the functionality it offered (which was only a fraction of what it offers now). I am also heavily involved in purchasing decisions for this sort of software for my employer. Tailscale's personal use plan led directly to a paid plan w/ my employer.

I'm sure I'm not the only such example of that path.

Exactly the same here. By the way, Headscale is great if you want to self-host, equally easy to run and manage.

As a Tailscale user, I am well aware. Tailscale being free doesn't mean they don't charge for it.

You comment makes it seem like it’s available only on the paid Tailscale product, or that Tailscale as a whole is only paid.

Ah, no, sorry. I meant "they charge for it in general so every feature that makes the product more useful makes them more money".