From Startup to Scale: How Tailscale Built a Billion-Dollar Business with Simplicity at Its Core

[00:00:01] Welcome to the Startup Builders and Backers Show, a podcast which is part of the Tech Talks Network. I'm Neil C. Hughes and you may know me from the Tech Talks Daily Podcast, which covers a completely different topic every day around how technology is ultimately impacting our life, our work and even world.

[00:00:22] But the Tech Talks Network is a series of unique podcasts that drill down on unique subjects and showcase the voices right at the heart of tech startups. And in this series, I want to shine a spotlight on the energetic world of startups where bold entrepreneurs and visionary investors come together and create the world-beating solutions of tomorrow.

[00:00:47] So the conversations you can expect to hear on this show will dive right into the journeys of those building innovative companies and also the strategic insights of those who support them. Balancing the excitement of breakthrough ideas with the more pragmatic challenges of scaling a business. So if you're a startup founder, you get to learn from other founders some of the mistakes they learned and also some of the opportunities that they unlocked along the way.

[00:01:14] So I invite you to join us as we unpack the risks, the rewards and the realities of turning those groundbreaking concepts into successful enterprises. It's a real feel good episode this one, and I think it will inspire startup founders and business leaders listening around the world. Truly great guy. I love chatting with him. But buckle up and hold on tight as I beam your ears all the way to Canada where you can listen to me and Avery in conversation today.

[00:01:45] So a massive warm welcome to the show. Can you tell everyone listening a little about who you are and what you do? I'm Avery Penran. I am a CEO and one of the three co-founders of Tailscale, which we started in 2019. As you said, you started in 2019, but you've been on an incredible journey because Tailscale recently crossed the $1 billion Canadian valuation mark.

[00:02:10] So I'm curious, how do you balance the expectations that come with being a tech unicorn startup against the need for sustainable long-term growth? Because it's quite a tricky balance, I would imagine. Yeah, well, it's certainly a tricky balance when we're only a company that's about four and a half years old and the expectations have been set that high. Yeah. I think part of our good luck is that the, I guess you could say the expectations were set so high that it has left the founders with a fair bit of control of the company.

[00:02:37] And so as much as there's high expectations that the, we have a lot of freedom to run the company the way we want to. And the way we want to is in a sustainable way of it is not going to like crash full speed into the ground, which it turns out is also what our investors want. That is, that's especially true since the tech economy downturn, whatever you want to call it, that started in sort of early mid 2022, where all of a sudden everybody's like, whoa, okay, remember how last year we were saying spend money as fast as you can.

[00:03:05] Now we're saying, now we're saying, don't die, because you might not be able to get any more money. And so as a fairly careful Canadian who doesn't like to spend lots of money in the first place and likes to be careful, suddenly I'm in my element where some of our competitors maybe are not. So I think this is pretty good. We raised a bunch of money in 2022, but our explicit goal is to like not blow through it as fast as possible. Like let's just use this as the way to make sure that we can build exactly the company we want to build exactly while the rest of the economy is sort of taking things slowly.

[00:03:35] And I think I should also highlight, this isn't your first rodeo. And as someone that's co-founded multiple startups and also worked nearly a decade at Google, I've got to ask, can you share some of your insights on how different leadership dynamics come into play in a startup versus a corporate giant? Because I would imagine you've got quite a unique perspective on this. I do have at this point a fair bit of perspective or experience, whatever you want to call it.

[00:04:02] My first startup, I started with my roommate in university back in the late 1990s. And it was actually kind of an experiment. Our plan was to start one while we were in school and just sell things for a few months and learn what it's like to start a startup, make all our mistakes and then shut it down before any of those mistakes caught up with us. So that we would know when we graduated, if we really wanted to start a company or not. And what actually ended up happening is we made a product, we sold it to some people, and then those people kind of really liked it. And they told their friends, at this point, we're starving students.

[00:04:32] We had this device that we could build for $1,000 and sell it for $2,000. With our $1,000 each time we build one of these things is a lot of beer money. So it was pretty hard to turn down all of this sort of word of mouth spread. And so it ended up growing faster than we expected. We brought in some what you might call late stage co-founder people to handle the business side. The next thing we were doing was fundraising, and we had a real company, and it grew to like 100 employees or so. And eventually, in like 10 years later, I exited to IBM.

[00:04:59] So that was an interesting experience, a little bit of accidental success there with a lot of ups and downs, because I really didn't know anything about business when I started. The entire purpose was to find out the basics, and we ended up finding out a lot more than the basics, and making a lot of mistakes along the way. After that, I spent a little bit of time in the banking industry, which is a whole like sideline of its own, and ended up joining Google a few years later. And that was like, it's a very big company. I think it is true what they say, or at least was true at the time.

[00:05:26] It was probably the most startup-like giant company I can imagine, because I'd had some like internship experiences at giant companies, and they were not at all like Google. And so I give them a lot of respect for that. I think things have sort of started to change a little bit in recent years. But generally speaking, they still, it is very startup-y. Lots of stuff gets created. Lots of stuff sort of then explodes, just like a startup. It's just that they're a big company. And then I sort of, I got a little frustrated there not having control over my own destiny.

[00:05:52] The thing that sort of finally set me off was the project I'd been working on for about six and a half years just suddenly got shut down, and with no real explanation. And so I left, and I'm like, okay, I want to start. I want to do a startup again. And the most important thing is not exactly whether I succeed or fail, but whether I'm the one who made the difference whether we succeeded or failed. I don't want it to be somebody else deciding whether we succeed or fail. And so that's kind of, that was my motivation for TailScale. Love that. Are you allowed to say what the product was that got shut down?

[00:06:21] Because there's been a lot of them over the years, isn't there? Yeah, no comment. No comment. The project I was working on was the devices that go in your home for Google Fiber. So Google Fiber is the US internet provider that rolled out gigabit fiber to several different cities in the US. And so my team was working on the actual, the Wi-Fi router, the TV box, the kind of stuff your ISP gives you when you sign up for the service. And we had custom everything. And specifically, I was leading the team that made the Wi-Fi router. So I learned a lot about Wi-Fi.

[00:06:51] And we sort of, I would say we advanced the state of the art of Wi-Fi a little bit. Because when you have gigabit fiber to the home, it turns out the reason people are not getting gigabit in their speed tests is not the internet. It is the Wi-Fi. And so we were right at the center of like, oh my God, how are we going to make it as fast as possible so people don't complain? It was very exciting. But in the end, and for good reasons, that's the problem. For good reasons, they're like, hey, maybe we shouldn't be making our own Wi-Fi router just for Google Fiber. Right?

[00:07:18] And eventually, they spun some of our technology out into what became Google Wi-Fi, which is the sort of consumer Wi-Fi routers. But it wasn't, it didn't make sense to have a team specifically doing it just for the ISP division with relatively low volumes. But all of those decisions were made like way above my head. It had no relationship with whether we were succeeding at building Wi-Fi routers, which we were. It had everything to do with business decisions. Yeah, 100%. And what about the slides and Google bikes? Was that still a thing when you were there? Or was that a bit? Oh, yeah.

[00:07:47] I mean, that's, that is, that was, Google started the trend in the late 1990s of like, let's over the top, let's super highly pay our engineers. Let's figure out every perk we can possibly find and just make it like a playground for people to like do their best work and think creatively and so on. And that worked super well for them. And everybody, well, the biggest companies started copying them. And so now it's like less of a competitive advantage than it used to be. But I don't think they can give up that stuff because they don't want to, they don't want to go backwards. Their competitors are giving the same things.

[00:08:17] Yeah. And of course, that path would lead you to Tailscale. And for anybody listening, hearing about Tailscale for the very first time, can you just tell me a little bit about that problem that you set out to solve with Tailscale? Sure. Well, the top line, I guess the name of the company is what we had first, even before I found my two co-founders. And it's sort of a joke. It's the opposite of Internet scale. And so I spent a bunch of time at Google building things for billions of people, right? Like, what would you do if this thing had to scale to a billion people?

[00:08:45] And like everything at Google was like, how will this scale to a billion people? And that had, by the time I left Google, sort of spread outside Google to the point where like people are the... It's a joke that's not a joke, like spitting up a Kubernetes cluster to host their personal website, right? And it was like, look, your personal website is just not ever going to have a billion users. I'm sorry to tell you this, but you're solving the wrong problem, right?

[00:09:07] And it turns out that, the way I like to put it, about 90% of the problems solved by 90% of the engineers in the world will never scale to a billion users. And that's perfectly okay. Even if you're an engineer who works at a company building a product that scales to a billion users, 90% of the stuff you do doesn't need to scale to a billion users. It's mostly like building dashboards or automated test frameworks or all kinds of stuff that's necessary to build your product. That's going to have 10 users or 100 users or even 10,000 users, but not a billion.

[00:09:36] And the whole tech industry has stopped building tools for those people. Everybody wants to build the super fancy sounding stuff that scales to a billion, but it makes everything harder, right? And so tail scale, just the initial motivation, the thing that got me and my co-founders excited is like, let's just build things to make the easy stuff easy so that I can do most of my work with less of this hassle. Right. And when it's worth doing the hassle, all those tools already exist. No problem. Right.

[00:10:04] But when it's not, you can just ignore that stuff. And that's the fundamental idea of tail scale. And the first product we produced, which turned out to be a humongous market and we've never expanded outside of that first product is networking specifically. Because if I want to launch an internal dashboard, if you look at most of the work you have to do to launch that internal dashboard, it's not building the dashboard. Right. It's making sure the people can log into the dashboard, making sure attackers can't reach the dashboard, making sure the dashboard can access the internal databases. Right.

[00:10:31] All of this connectivity stuff that is completely tangential to the thing you actually wanted to do takes 90% of the work. And tail scale just makes that 90% of the work go away. And it's a hell of a journey you've been on here. And I think what is most impressive, we're talking about four years in business, 2019. It must have been an incredibly exciting time. But then, of course, came a global pandemic and you've had to say, global scale, global pandemic and economic uncertainties.

[00:10:56] I'm curious, what were the risk mitigating strategies that you employed during that time? And how did they differ from conventional wisdom? Because it was, I can't begin to imagine what it must have been like during that time for you. It was, I mean, it was certainly exciting. We raised our first round of funding near the end of 2019. We hired our first employees in, I think, February 2020. Before anybody really expected things would get as bad as they were. And next thing you knew, there were stay-at-home orders and lockdown starting in March 2020.

[00:11:24] So we always intended to be a remote company, at least on the engineering side. We hadn't made any commitments on the non-engineering side because that early, we weren't hiring anybody except engineers. But we were sort of forced into, well, I guess we're going to be a fully remote company when lockdown continued for like two plus years after that. As a company making, it turned out, remote connectivity tools, not, it's bad to celebrate the pandemic, but it was extremely good for us business-wise. We can't, we cannot deny, right?

[00:11:52] All of a sudden, everybody had the same problem, which is their stuff that they had at the office that was connected to everything they needed to do was now locked in an office that they were not in, right? And so all of a sudden, everybody needs to get their connection into the office to access all this stuff. And they were finding out that the remote tools that they had set up for like people occasionally to go traveling to a conference or whatever, were not going to scale to every single employee being remote 100% of the time. It was a disaster.

[00:12:19] So the only thing I wish had been different would be maybe if Tailscale had started maybe a year earlier, we would have been a more mature product in time for all of these emergency impulse buys of connectivity tools to try to fix this stuff. Because a lot of people ended up locked into things that were not that good, but they got a good discount on a two or three year enterprise deal because that thing existed right at that moment. Tailscale still, it launched us into success without a doubt, right? But if our product had been a little more ready at that time, we could have made a lot of money fast, like some other companies did.

[00:12:49] Zoom being super notable, right? Their valuation skyrocketed because everybody suddenly needed to have remote meetings all the time. Everybody who previously didn't like remote meetings or would avoid them had to learn how. And had to do them all day long. So suddenly, if you're a remote video conferencing company, like you're worth zillions. And of course they were. And now everybody, even though things have opened up again, the big difference is everybody now knows how to do remote meetings, right? So Zoom is not going to, maybe the valuation goes down a little,

[00:13:18] but the need for video conferencing is never going to go back down. Yeah, it really was a crazy time. I remember reading at the height of all that stuff that I think Zoom was worth more than the top five airlines combined. It was just absolutely insane. Well, it was pretty hard luck being an airline at that time. That's true. So it's one of those like, well, Zoom was a little inflated. The airlines were a little deflated. And it's like, nah, still, I do a lot more Zooming than I do flying. Yeah.

[00:13:44] And Zoom's like cost to provide the service is a lot lower than an airline's cost. And of course, you were named one of VentureBeat's top 20 zero trust startups to watch here this year in 2023. So I'm curious, how would you differentiate hype from reality and the zero trust security model? Because there's been a lot of hype, a lot of talk, and it's a very crowded space, isn't it, as well? Oh boy. So zero trust, I think it's both a joke and not a joke in the security industry

[00:14:14] because everybody knows that nobody knows what zero trust is. And also, every security department has some giant zero trust budget to implement this thing that they're not really sure what it is, right? And so it's a super weird market. Like the whole thing is hype, basically. I have a simple definition of zero trust that I think actually is relevant that maybe not everybody shares. But it's the one that I think is sort of where it all came from. But actually, all of this zero trust stuff derives from what I think

[00:14:44] was invented at Google during the time I was there. Certainly not by me, but by people that I know that they called BeyondCorp. And it was a simple idea of like, look, just because you're plugged into the physical network shouldn't give you access to a bunch of super secret high security stuff, right? And that's the way most companies even still today operate, right? If you're in the office, if you're plugged into the network, a bunch of stuff is basically sitting there waiting for you to use it slash attack it, right?

[00:15:11] And the original assumption was that to plug into that, you had to be able to physically get into the office. It meant you had a scan card and like people were looking at you and stuff. And like, that's decent security. And then somebody invented Wi-Fi. It's been a while since this happened, but somebody invented Wi-Fi. And now they like super secret secure internal private network is leaking through your walls in like through it as radiation, right? So somebody can sit outside your office. And I mean, there's stories of people with flying drones to sit on the roof of a building and then penetrate their Wi-Fi and access all the stuff.

[00:15:40] Like the physical network is no longer to be treated, trusted as secure, right? It just, you can't. And so zero trust means don't trust the physical network. It's not good enough. What zero trust does not mean is let's build a world where nobody trusts anybody and we can't trust anything. And like, let's build a distributed consensus algorithm, blah, blah, blah. It's not that. It's just like, look, if you're going to trust, you have to build that trust. And usually that comes because you do encryption and you somehow get certificates and logins associated with people and devices

[00:16:09] so that the physical network doesn't matter because the only thing going over the physical network is this encrypted authenticated traffic, right? So it's relatively simple in the end. Zero trust in the physical network. Trust something else. Trust cryptography, right? And there's a lot of people building a lot of different products that fit in the, well, don't trust the network, trust cryptography category. I like the way Tailscale does it. But there's lots of other products that do the zero trust thing in lots of different architectures.

[00:16:37] What makes it confusing is that you say, I want zero trust, but you don't know which architecture you're going to buy because there's a hundred different ways of doing it. And we've dared explore the buzzword that is zero trust and the hype that surrounds it. The other one, of course, is enterprise VPN solutions. There's a other can of worms right there as well. You guys launched a zero trust virtual private network solution for enterprise customers. So can you talk through some of the unique challenges

[00:17:06] in building something like that? Because again, huge talking point, right? Yeah. So it's interesting. It's an interesting positioning problem that Tailscale sort of, we think about every single day. And the interesting positioning problem is every enterprise has a VPN. Every enterprise quite dislikes their VPN. But every enterprise has a budget for a VPN and is more than willing to replace it. And VPNs are like, have not progressed in probably 20 plus years.

[00:17:34] It's the same garbage that it was 20 years ago, which maybe wasn't garbage 20 years ago, but now it's kind of garbage compared to the stuff that we expect our computers to be able to do today. Right? So Tailscale can easily replace or supplement that VPN thing that you've been using with a much better experience and much more modern technology. Right? So we position ourselves kind of as an enterprise VPN, partly because when we talk to customers and we say, here's what Tailscale does, the first thing that jumps into their head a lot of the time is like,

[00:18:04] wait, that sounds like a VPN, just better. Right? And in fact, we've had one customer, my favorite quote from a customer of all time. I can't believe they said this, but they really did. It's like, we often go out and we'll ask them, how would you describe Tailscale? And they're like, look, I hate to break it to you because I know you'd rather not be described this way, but you're a VPN. It's just that you're the best VPN anybody's ever used. You're the VPN that changes the way you think about VPNs. I'm like, this is great. I don't know if I could really put that on my website. Sounds a little over the top,

[00:18:33] but that is what they said to us. Right? And then we're balancing that against security teams that also have a budget for this zero trust thing. Tailscale is also a zero trust thing. People wouldn't naturally, like IT people would not naturally describe this that way because they're not looking for zero trust stuff. They're looking for connectivity tools, right? Security teams look at it and say, wait a minute, this thing is zero trust. And I'm like, well, yes. So we have to kind of admit that it's zero trust. But the thing that actually gets people excited to look at it for the first time is that it's a VPN.

[00:19:00] And considering your focus on security, I've got to ask, are there any new threats that you might see arising as a result of advancements in AI? We're hearing a lot of stories of good AI versus bad AI. And what are you doing at Tailscale to prepare and mitigate some of these challenges that might be on the horizon? So that's actually, there's a whole big area, of course. I like to think of it is AI is a progression

[00:19:28] of all of the bad stuff that technology has already been doing to create new ways of breaking into your computer now, basically. Right? And so again, going all the way back to Tailscale, it's the opposite of internet scale. One of the things I believe a lot is that computer networks follow a lot of the same laws as human social networks, right? Human social networks evolved to trust a small number of people and then trust a little less, a larger number of people and a little less, a larger number of people. When you get to a billion people,

[00:19:58] you do not trust everybody, right? Almost all of those people are not in your social network. And if someone came to you and said, I have a boat to sell you, it's only $1,000. If that person is not in your social network, you'd be like, I don't know, probably not going to buy that boat, right? But then on the internet, we just took all of the computers and stuck them out there on the internet. And anybody can come in and say, can I access your web server? Oh, let me probe around and see which user accounts are in there, et cetera. It was like, there's no reason that a billion other computers on the internet

[00:20:26] should be able to do that to your private server that is only supposed to be used by your friends or your coworkers or your company, right? And so the point of Tailscale is to take that stuff off of the public internet to get into the technology side. Like we allow you to bypass your firewall so you don't have to open any ports at all. You just leave something inside your firewall and you leave another thing inside a different firewall and they can find their way to each other by mutually agreeing to it because they have this cryptography link, right? And then only the people that are supposed to have access

[00:20:54] can even see that it exists, right? When that happens, the whole class of threats that comes from being on a too wide social network of a billion computers just goes away. And so AI is an advancement of the threats that come from the network being too big. It's a really big advancement. You're going to see some spectacular new threats coming in from this big network, right? Especially things that exploit people on Twitter and stuff like that by like sounding like a real person and trying to convince you to do stuff you shouldn't be doing, right?

[00:21:22] But tail scale just wipes out that whole group of people slash computers that now you can't tell if they're people or computers out of your threat model, right? Only the people inside your network become the threats. And those people generally are not that threatened and you can trust them, right? It's funny tying it back to zero trust. I always find the term zero trust so funny and so misleading because the whole way you achieve security is trust, right? The point is though, you have to think about trust and you don't just give trust to everybody, right? By default, everybody has zero trust

[00:21:52] but you have to build up this trust from a small select group of people that you actually want to be working with. It's so refreshing to hear somebody talk about zero trust in this way, let me tell you. And of course, you mentioned earlier in our conversation that one of your earliest startups was acquired by IBM which is a huge talking point on its own. So I'm curious, were there any lessons that you learned from that experience and did those lessons influence your approach at Tailscale? Is there a story there?

[00:22:20] Well, I guess I would put it this way. Getting your startup acquired by a big company has a couple of predictable outcomes. One of them is you make a bunch of money. So pro. The other one is they probably rip your product to shreds and ruin it and you never see it again. So con. At this point in my career, I've made enough money. I'm not super rich by any stretch of the imagination but I'll be fine, right? And my point of view, what I want to do with the rest of my career is build something that matters, that continues to exist, that nobody's going to cancel

[00:22:50] without my permission. And therefore, I don't think getting Tailscale acquired would help me achieve my goals, right? Like it's probably one way or another not going to achieve my vision anymore. Even if it doesn't get completely shredded by whoever the acquirer was, it would probably go off the course I think we should be on, right? And so the most important thing I learned is like, yes, if you're starting a startup and what you want to do is get rich, like it's a way to do it, right? But it's very sad and I think almost every founder whose startup gets acquired

[00:23:20] is sort of in denial about this at first because the dollar signs are so big, right? But not long afterwards, they're like, oh crap, it's gone. I'm sad. I will wipe my tears away with all these dollar bills. I can really get what you're saying. I've spoken to a few people on this subject and obviously from somebody outside the industry, they were going, well, why don't you just drink cocktails on a beach for the rest of the days? You're going to be like, yeah, you can do that for two or three weeks but by the end of that three weeks, you're just blowed and fed up and want to do something and well, why don't you travel the world? Okay, where's on your bucket list? Okay, you've done that.

[00:23:49] Now what are you going to do? And you need a reason to get out of bed and a mission and to create something. Yeah, I mean, a lot of entrepreneurs are driven by this so-called need for achievement, right? It's the number one thing that makes them go and like having your achievement reversed even in exchange for a big dollar reward doesn't actually, I mean, it feels good for a few moments but then you're like, oh, well, I'm going to need to go achieve some more stuff right now, right? And sometimes it's easier to start the next startup with a bunch of extra money, right? And a bunch of like reputation that you gained from making your investors

[00:24:19] a bunch of money on the last one, right? It doesn't hurt but it's still, it's a major setback. You go back, it sets your career back years and now you have to start over again. Right? That said, also a lot of entrepreneurs really prefer the first few years of a startup, right? Everyone's got their favorite phase and the being a big company phase is a very different experience than the early stage. So where's your favorite phase in all that? I would say like historically my favorite phase has always been the absolute total chaos at the beginning. Yeah.

[00:24:49] But I'm kind of growing into the, it's annoying at the bigger phase. Like there's a lot of just what I might call dumb problems. One of my investors a couple days ago was just saying like, at some point in your startup you start to realize that all of your problems are people problems because there is no other kind of problem anymore because every problem needs to be solved by people. And so if it's not getting solved then you have a problem with people, right? And you know what? I grew up, I like to live in my parents' basement and I was writing code

[00:25:18] and this was my favorite time and I didn't really like people that much. So the fact that all of my problems now are people is not that inspiring on a day-to-day basis. But I really like, again, this sort of this drive, this need for achievement means like I get over that because the level of achievement that's possible when a company has this level of success and this level of customer love and this level of momentum is just, is really fun, right? So even though like my daily is like, oh, another meeting. It's so cool to go to a customer and say like,

[00:25:48] remember all that stuff people have been telling you about VPNs and zero trust? Like just try this and five minutes later you will get it, right? And they do, right? They can understand it within five minutes of trying it and it's such a fun experience. Absolutely love that. And talking about your vision for the future, where do you see the most exciting opportunities for Tailscale, particularly as 5G, edge computing, IoT, et cetera, so many emerging technologies beginning to converge and grow throughout the industries. So where do you

[00:26:17] see things going? What exciting opportunities are there for you? So this gets into sort of like the technology vision of Tailscale, but the sort of thing we stumbled into and it started out as kind of a joke because it was like a line from Silicon Valley, the TV show, but it turns out to be really true. It's like Tailscale is kind of the new internet, right? We built this internet starting in the 1990s to connect everybody and we dreamed that when we connected everybody, like communication would be better and society would be improved and all this other stuff would be so great.

[00:26:46] And where we got to is now just like I'm afraid sometimes to turn on my computer because who knows what kinds of weird hacks are going to come in or like people are like attacking me on Twitter or whatever, right? We created this network that's so connected that now everybody can attack anybody anytime, right? It's like that's not fun. That's not fun for people and it's not fun for computers, right? Tailscale is sort of this like wait, what if you thought about that a different way? What if we modeled a computer network based on the way humans are sort of evolved to work with each other,

[00:27:16] right? Then you could have better relationships with people you want to have relationships with and not have people intruding randomly from all over the world who never knew you that just want to cause you pain, right? That is, it's kind of lofty but I can imagine a world where like every single device should have Tailscale on it, right? If you look at, I was around in 1995 when Microsoft Windows 95 came out. In 1994, TCP IP was an add-on option you had to buy from a third party. Windows 95 came with TCP IP for the first time, right?

[00:27:46] And now, like I bought an Apple watch, right? If I had a watch that didn't have TCP IP on it, it would be like, what's this thing? It doesn't do anything. It doesn't have internet, right? And that's the space of less than 30 years, right? I could imagine a world where in less than 30 years you're thinking like, well, why do I want the old internet? Like this thing, it needs to connect me to my devices, not the internet, right? And it needs to be safe and that should just be the default. And whether that's Tailscale or whether it's something like Tailscale, I can see that's where things are going, right? And 5G and IoT and everything,

[00:28:16] like all these devices need to be on some sort of network. I do not want my internet connected light switch to actually literally be on the internet. That's dumb. It should be connected to me so that I can turn my lights on and off, right? And that's not how they're built right now. They go through some cloud provider that could be broken into at any moment and somebody is changing my light settings. Well, you mentioned Silicon Valley and Twitter there. I don't know if you saw the CEO interview from Twitter or X as it's now called where she didn't have a copy of the app

[00:28:45] on her own phone. It felt like a Silicon Valley moment itself that did. Well, I loved chatting with you today. I think we could chat for so much longer but before I do, I always like to finish on a light hearted note. So I'm going to put you on the spot here and throw you a few curveballs and we've got an Amazon wish list. I always ask my guests to leave books to to leave a book on and also I always ask my guests if there's somewhere someone they'd like to have lunch or breakfast with. So I'll let you answer this but if you could choose a book for everyone listening

[00:29:15] or choose someone to have lunch with, what would you leave everyone listening with tonight? All right, well, this is a good set of questions because I can answer them both the same way. I think everybody at work at this point thinks I'm a stereotype because I say this at almost every meeting. Crossing the Chasm, best business book ever. It is the thing we did wrong in my first startup. It's the thing that many failed projects at Google really should know if they just read the book and it's the thing that Tailscale is using as our textbook that has actually got us to the level of success we have today.

[00:29:45] Virtually guaranteed that is the secret to how we are where we are. I love that book so much. It's everything you need to know about starting a startup. And of course, Jeffrey Moore is the author. So if he was around for breakfast, I would fly there to have breakfast with him because he is absolutely my hero. Awesome. Well, I'll get that added to the Amazon wishlist and we'll stick Jeffrey Moore into the ether now. Let's see if we can manifest something together. For anyone listening that we may have sparked a few light bulb moments want to find out more information about Tailscale.

[00:30:15] Dig a little bit deeper. Where would you point everyone listening? Well, Tailscale.com has a blog at Tailscale.com slash blog. I also have my own personal blog where I post more controversial stuff at appinwar.ca. You can find many references to Crossing the Chasm in there as well as lots of other stuff. And also we're at Tailscale.com on Twitter as well if you want to follow all our latest announcements. Brilliant. Well, I'll get all those links added to the show notes so people can find you nice and easy. And you've achieved so much in your fantastic career now. And just the last four years

[00:30:45] that a security network startup valued at more than a billion Canadian dollars and named one of VentureBeat's top 20 zero trust startups to watch. And you did it all in the middle of a global pandemic and economic uncertainty that followed. But it's just the story behind it. A real pleasure chatting with you today. So thanks for sharing your story. Yeah, it's been great being here. Nice to meet you and all the best for your podcast. Wow, what a great story. If you've got a team that just wants secure private networks without weeks

[00:31:15] of setup and configuration, Tailscale really does have a reputation for making it easy. And I think we all know some of those existing corporate VPNs that will remain nameless. Unlike those, Tailscale doesn't have upfront costs, minimal latency and works with other existing services. So I do urge you to check that out, especially because they launched that Zero Trust virtual private network solution earlier this year. Lots to explore, but more than anything for me is the story behind it.

[00:31:45] And I do hope to meet Avery in person one day in the near future. Great guy. And for anyone listening, if you've got a story you'd like to share with everyone, please email me. Thank you. Thank you. Thank you.