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Tailscale raises $100M

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Re: Tailscale raises $100M

#111
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.

Re: Tailscale raises $100M

#112
What's the state of affairs when it comes to self-hosting?

I'm waiting to deploy either Nebula, ZeroTier, or Tailscale, but we don't want to rely on third parties for auth or coordination.

Re: Tailscale raises $100M

#113

For anyone else who wonders wtf tailscale is: > Tailscale is a VPN service that makes the devices and applications you own accessible anywhere in the world, securely and effortlessly. It enables encrypted point-to-point connections using the open source WireGuard protocol, which means only devices on your private network can communicate with each other. It seems to take care of key distribution, nat-traversal, authen…

I'm about to go away but having local access will be very useful.

I've just setup tailscale in a few minutes, very smoothly. I'm impressed it scales down to this kind of simple use case nicely, and it seems it has nice features as my use cases might scale up.

Re: Tailscale raises $100M

#114
Crazy how people can raise these sums of money, it's all about who you know.

I also notice they have a careers page so I had a gander. A 6 stage interview process! Good lord tech companies really have gone down the shitter

Re: Tailscale raises $100M

#115
post #81

For anyone else who wonders wtf tailscale is: > Tailscale is a VPN service that makes the devices and applications you own accessible anywhere in the world, securely and effortlessly. It enables encrypted point-to-point connections using the open source WireGuard protocol, which means only devices on your private network can communicate with each other. It seems to take care of key distribution, nat-traversal, authen…

I thought that Tailscale was pretty interesting. Avery Pennarun, its CTO, is somebody whose judgment I am used to trusting. Then I learned that to use it, I would be dependent on authenticating using a login on one of the unaccountable internet behemoths who could take away my account for any random reason or no expressed reason at all. No, thank you.

Google does that, Microsoft doesn't. Microsoft will ban you from a particular service if you egregiously violate the terms of service for a particular application of theirs, but never the whole account.

Google will throw you on your ass in the blink of an eye.

Re: Tailscale raises $100M

#116
post #41

As the founder of what some say is a competitor (ZeroTier) I'd like to congratulate the Tailscale team. We don't really see Tailscale as the competition. We see the competition as: (1) The old school castle and moat IT model that dominates at 99% of companies. If we can disrupt this then TS, ZT, and four other upstarts could all become billion dollar companies. Right now 1-2% of this market has been disrupted at most…

Agree with this Adam.

Avery and the team at Tailscale are building a fantastic product and totally deserve the round and recognition, huge congratulations - we're super happy for them.

In many ways they're also an ice-breaker for the zero trust overlay network architecture, which means they've got the most work to do. As the current top comment on this thread correctly notes, with huge investment comes the obligation to eventually pay it back.

The market hasn't even come close yet to crossing the chasm and seeped into mainstream conscience to become the accepted norm - yet.

That said, we believe fiercely that networks should be simple to reason about, easy to use and safe to operate. That private connectivity should “just work”, and just work in exactly the same way, everywhere too. Flexible to change, simple to automate and only available to the right things at the right times.

When you think about it, building private networks is actually pretty complex right now and can be pretty insecure too. It's some unholy combination of spell casting meets a yak shaving contest to wrangle firewalls, VPNs, MTUs, and manage IPs, subnets, ACLs, NSGs, VPCs, NAT, routing, VLANs, certificates & secret keys, then hoping a zero-day doesn't show up that drops someone straight into the network via the VPN server, who then starts poking around the squishy centre.

Once you've used products like Enclave, Tailscale or ZeroTier and seen how simple private networks really can be - at a certain point you almost stop and ask the question, why would you not do it like this.

There will always be nay-sayers and people for whom this approach just isn't a fit, and that's fine - but I personally find it hard to imagine that this genie can be put back in the bottle.

- Founder @ https://enclave.io

Re: Tailscale raises $100M

#117

Earlier quoted context omitted.

This is kind of overstated. Even if everyone went IPv6 and gave every device a public IP address, pretty much every network would have a firewall that behaved just like NAT.

> Even if everyone went IPv6 and gave every device a public IP address, pretty much every network would have a firewall that behaved just like NAT. No, they do not behave just like NAT. With NAT you have two problems: * figuring out your address * firewall hole punching With IPv6 you already know your address and just give it to the peer you are communicating with. You then tell your firewall to allow connections fro…

No, no, no, no. You haven't really experienced the quality of IPv6 routers at home. The only thing that I can (probably) say with confidence is you will not need TURN, and even that assumption can be broken with even more restrictive firewalls that block nearly all UDP traffic or even not know your real public address because IPv6 NAT does exist (https://blogs.infoblox.com/ipv6-coe/you-thought-there-was-no..., https://datatracker.ietf.org/doc/html/rfc6296), but fortunately this is usually found in enterprise stuff. NAT-PMP or router UPnP is probably the wildest: majority don't (remember that I'm focusing on ISP routers since that most people don't bother to switch to actual routers...*), some only on IPv4 (which is even more frustrating), and only few supports it correctly. Worse, those same broken garbage-level routers have NAT-like firewalls: at least you know what address and port you will contact the other computer, but you will still need UDP (TCP handshake will be very problematic) and you will still need keepalives (or otherwise your firewall will just close the port).

* ... and most that do get another router (usually because they have seen that their Wi-Fi on the "modem" is bad) don't turn on** bridge mode which will be a definite headache on both IPv4 (double NAT) and IPv6 (address conflict, especially if you're using an ISP like Comcast that would only allocate a /64 and no more.

** ... because you need to call up the ISP or even outright refused to bridge it (either because they're stupid but you don't have another ISP to switch or the equipment manufacturer of their garbage special router didn't program one).

Re: Tailscale raises $100M

#118

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…

No post body was provided.

Re: Tailscale raises $100M

#119
post #51
post #14

I read almost all of TFA (started to jump paragraphs near the end) and still couldn't figure out what it was or did, even after being told, repeatedly, that they "make easy things easy". Apparently, it's a VPN.

The blog post is poor. It has TailScale's "house style" of folksy reminiscence and Avery's stream-of-consciousness writing stylewrapped around an announcement. It only says two things, one at the top, and one at the bottom: "We raised a $100m for our war chest; we don't have any plans for how to use it besides extending runway for our current operations". The middle is left trying to justify why that is a good thing,…

I thought the post was remarkably well written. I had a vague idea what Tailscale did going into it, but this post did a good job of describing the company's values and vision. I'm not sure what the intended audience of the announcement was, but for me it was interesting.
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