How have you kind of managed that, I suppose, the expectations of others? So

I have to say, I don't really know.

What happens is I go to, well, our very first funding round, what happened is we weren't actually sure that we wanted to raise money.

We went down to Silicon Valley and we thought, let's meet with some investors and ask them, like, what do we need to do, do you think, to make this company something that would be worth investing in? And then we'll come back in a few months and hopefully we'll have done that and we'll talk about fundraising.

And it turns out there's this saying that I had not heard until then, that is like, if you go to a VC and ask for money, they give you advice.

If you go to a VC and ask for advice, they give you money.

And so they were just like so confounded that I didn't show up with a pitch deck that they were like actually thrown off.

But what do you think to that? If you think about your peers, do you think there is an increased level of pressure at the moment to make sure that you are across those skills and that you are the tip of the spear? I think so.

had open claw up at a tab the other day and it's like i can't do it i can't i was reading what it's like i'm not i can't it's too scary

yeah well exactly and so you know you know the the big picture for aperture uh which i'll tell you it's like if i was to make a one-liner of the challenge i made to our team uh is like hey what could we do or what do we need to build in order to make open claw assuming open claw freezes today it never gets any better right what would we have to do in order to make this thing safe for our employees to run on our tail net, right? And our security team is like, whoa, no, no, no, stop, hold on a second.

I'm like, well, you know, use your imagination.

It's not there yet.

OpenClaw is pretty hard to secure, but what would you need to do to make this thing not horrifically dangerous, right? Because that's what the world wants.

They want to be able to write horribly insecure code and have it magically work out to be not dangerous.

That is a wonderful dream.

uh to aperture that's on my tail net what what am i looking at

Okay.

Um, and it just goes through the login with Microsoft endpoint.

Uh, it also works with Okta.

It works with everything that supports OIDC.

Anyway, uh, once you've logged in, then it uses that login token, uh, to take your WireGuard key, and it signs your public key, sends it up to Tailscale and says, like, "Hey, I can prove that this key belongs to, uh, this person who successfully logged into, say, Entra."Right? And then we provide that information back to everybody else on the tailnet.

Uh, and so they can say like, "Hey, when I got this packet, it came from definitely Avery on my corporate domain." Right? And if you can do that, you can have...

And, and we also have, you know, the group information from Entra, so we can say like, "Well, Avery is in these five groups in Entra." And so when I write a policy that just says like, "Okay, engineering team in Entra is allowed to access devices like this," then it can be a simple one-liner like that.

... or these sorts of things.

had open claw up at a tab the other day and it's like i can't do it i can't i was reading what it's like i'm not i can't it's too scary

yeah well exactly and so you know you know the the big picture for aperture uh which i'll tell you it's like if i was to make a one-liner of the challenge i made to our team uh is like hey what could we do or what do we need to build in order to make open claw assuming open claw freezes today it never gets any better right what would we have to do in order to make this thing safe for our employees to run on our tail net, right? And our security team is like, whoa, no, no, no, stop, hold on a second.

I'm like, well, you know, use your imagination.

It's not there yet.

OpenClaw is pretty hard to secure, but what would you need to do to make this thing not horrifically dangerous, right? Because that's what the world wants.

They want to be able to write horribly insecure code and have it magically work out to be not dangerous.

That is a wonderful dream.

uh to aperture that's on my tail net what what am i looking at

Can you talk a bit about why you see that as so essential?

Well, this is, this is really important, right? I mean, Tailscale, it's a VPN.

One of the things we do is security, right? And we hire some of the best security people in the world to make sure that our system doesn't have any holes in it.

Uh, historically, law enforcement and government systems don't have that same bar, right? And the problem with security is like we, we, we, like, compare it to a chain, and the weakest link in the chain is how strong your chain is, right? We are talking about a regulation that in a very hand-wavy, nonspecific way says, like, "Maybe we're gonna require you to put in specific stuff that lets us access your systems," right? And that, you know, that makes sense.

You imagine, like, the olden days with, like, literally analog telephone where, like, when they, what they mean is we're gonna put a tape recorder and somebody's gonna go into the office, and they're gonna clip the tape recorder to a literal wire that is literally the phone cable that goes to somebody's house.

And it's like, okay, I understand that.

It's pretty hard to misunderstand how this works, to misuse it for, to be, like, an unexpected vulnerability in the system, right? Software is not h- not like that at all, right? Like, this, these systems are so complicated, the chance that, like, the, the RCMP is gonna come up with some system that is secure enough that when they force us to plug it into Tailscale, the system is not going to be less secure overall is, is basically zero.

Uh, can you talk a bit about what that impact might ultimately be if this passes in its current form? Does, does this mean exiting the country? Does it mean exiting certain services? How, how do you envision trying to, to deal with legislation that, at least at the moment, could include both the prospect of both backdoors and, and access to encryption as well as the, the metadata retention requirements?

What are some trends you're all seeing among your customers about how they're using Tailscale, what they're securing, and, and how they're using it day-to-day?

So I think, I mean, one, one thing that's maybe telling about it is, like, we're having a conference about, about Tailscale, and if you think of Tailscale as, like, it's a VPN, like, w- when was the last time you heard of anybody going to a, a conference about a VPN product, right? Does- doesn't really make sense.

It would be the most boring conference you can imagine.

And yet, there's lots of people who are really excited, excited to go to Tailscale Up.

And why is that? It's 'cause Tailscale is kind of a fun toy.

I mean, it's useful at work, uh, but it's also, like, fun to play with 'cause it has this, like, I guess we could say, cult following.

Because when you try it, it just kinda makes the network work the way it's supposed to work, right? Uh, and so for people who haven't done it, you can get it from the App Store, you download it from the App Store, you log in with your Google account or your Apple account or whatever, uh, your corporate SSO, right? And then all of a sudden, you're just on the network, and all of the other people who are on that same network or all the other devices are on that same network, they can just see each other, and you don't have to worry about firewalls, you don't have to worry about CGNAT and NATs and, and operating systems and all this other stuff.

So really in a, in a cloud-first world, Tailscale makes everything feel local.

So for folks out there who don't know, what does Tailscale do?

All right.

So super simple, uh, answer is Tai- Tailscale is technically a VPN.

That is the like space in the technology world that it occupies.

That doesn't really tell the whole story 'cause VPNs have basically stagnated for 30 years, uh, before Tailscale showed up.

And so it doesn't work like IPsec or whatever you're used to.

Tailscale uses this new thing called WireGuard.

Mm-hmm.