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 feel like people are so concerned about infinite scaling that nobody ever tries to scale to 5 anymore.

I have a big collection of movies, and I’d like my mom-technical blue collar friends to be able to watch them. I trust them, and I have trusted communication channels with them. We exchange keys somehow.

With the sort of routing I’m describing, they could watch my movies and I wouldn’t have to have a public IP address. And I wouldn’t mind if their friends (that aren’t my friends) watch my movies, either, by forwarding through my friends. What’s the catch? This could work for that. How could I do this today?

I don’t have any ideological or moral problem with blockchains, I just think they suck at solving problems where the requirements for trust are low or met elsewhere.

edit: mom-technical was a typo of non-technical but I’m leaving it because it’s more accurate.