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.

Cloudflare already has a competing product https://www.cloudflare.com/en-in/lp/ppc/cloudflare-for-teams...

It’s not really a competing product until they relaunch it with a heavy consumer focus and with some of the properties that Tailscale has, ie: avoiding going through the cloudflare CDN. But more to my point, cloudflare is definitely in a position to outcompete Tailscale, it’s just a couple tweaks and a marketing shift.

I don't think Tailscale will focus on the consumer market, I'd be very surprised at least if they did. I think they built a developer-friendly product to get mindshare and early adoptors, but eventually the real market for such such products is in the B2B space, i.e. implementing the "BeyondCorp" model of zero-trust networking. There's also a market for building cloud mesh services but I'm not sure if Tailscale is well positioned for that as there are good open-source solutions available for that already.

They already (sort of) do [0] as they have a "Personal Pro" plan that's not too obvious - personally, I hope they expand to make it more cloud-native via a la carte pricing for those users as I'd pay an extra $x/month for an additional subnet router or three. And, IMO, it's a smart approach - those who are the targeted "Prosumer" might leverage this for their homelab and carry it over with them into the enterprise. I say that it's a smart approach because in my time at a vendor that was slinging security middle boxes - we used to give away our small form factor product to those homelab'ers for free. They'd take them home and see how much the solution could provide, they got comfortable with the UI, and they learned it for their own use cases. And then the path into an enterprise conversation held much less friction.

[0] https://tailscale.com/pricing/