Tailscale raises $100M

Tailscale has a fantastic product, I’ve been extremely happy from day one. If you’re waiting for a weekend to have a few hours to try out Tailscale, don’t, it takes 15 minutes to get every device you own up and running and talking. This is the lowest friction personal VPN to ever exist, and once you see how easy it is for your own devices, you’ll wish you had it at work.

The biggest risk that this company has is that Cloudflare (in all reality) should just buy them or reimplement it. It’s the type of product cloudflare would make, that’s for sure. Being based on open source wireguard, and being just a STUN/TURN server at its core… I’m sure that Tailscale will be the first but maybe not the best.

I’ve been dreaming lately of a tor-like network that’s based loosely on the idea of tailnets. Rather than blockchain bullshit, you’d have a direct ring of trust with friends, and then you could set up access policies to forward packets for people you don’t trust, but who know someone you do trust.

Web3 happens when people can host stuff on their phones, and Tailscale is something that lets you host things on your phone.

> a direct ring of trust with friends

The vision you outlined is great, except it doesn't work. The trust assumptions are too high, and even a great product like Tailscale seems to rely completely on centralized identity providers (you have to choose Google, Microsoft, or Github on sign-in).

Ultimately, if you want to maintain full control of your online identity and network, you'll probably need some of the decentralized (but economically aware) resources you seem to have issues with — or at the very least a means of transitioning authentication to private key methods with DIDs.

I self host headscale as my control node of my tailscale vpn so no sign ins required, I just give keys out to anyone I want in my vpn.

My problem is the client doesn't support multiple servers, so I can't have a work vpn and a home vpn, not even with an easy toggle - you have to run tailscale with different conf options for both. Changing namespaces also isn't easy, so having friends and family segregated even on one server is also a pain point.

Thanks the main objection I have with tailscale is that you can't self-host (and you need external identity providers). I had no idea there was a self host option. I'll investigate. I assume it's an unsupported community option?