Andrew Rubin (00:00:00):
We raised, in the first six/seven months of the company's life, over $40 million. The team hadn't hit 20 people, and we already had 40-plus million dollars in fundraising. And basically the month we started generating revenue two years later, we raised a hundred million dollar round. There is no doubt about it that we went in not understanding what we were doing. We understood the technology, and we understood the domain very deeply. And that was, I think, one of the two things that saved us early on. Was that we weren't making up what we were trying to do as we went when it came to the product story. We had a very sharp and, I'd like to think, a pretty educated point of view on what to build and why. 10 years later, I think we might be starting to be right about that. I've sort of taken to saying that the difference between being very, very, very, very early in something and being too early in something, T-O-O of course. It's really only one word. And the word is actually not time, it's bankruptcy. And the reason I say that is because we all know, especially in technology. There are ideas that come before their time all the time. You know, if you're not playing the game, you can't win it. And so the reality is that, yes, you do have to look at the data. You do need to look at the signals. Sometimes they're very early and very weak and very faint. And sometimes they're right there up in your face, and you know exactly what it's telling you. By the way, good and bad. But I also believe for a fact that an entrepreneur's number one job is to absolutely be that sort of voice of conviction in the room. I thought activity will equal money funding, because everybody talks about, oh, well, I pitched 100 VCs to get to the one. But sometimes pitching 100 is actually no better than pitching eight if it turns out that there's only three that really are gonna get your pitch. Another one of my mentors said to me. On the really good days, you're gonna think you have it all figured out. And on the really, really bad days, you're going to think it's the end of the world. And I promise you, neither one of them are ever going to be right. And I was like, that sums it up perfectly.

Previous Guests (00:02:07):
That's product market fit. Product market fit. Product market fit. I called it the product market fit question. Product market fit. Product market fit. Product market fit. Product market fit. I mean, the name of the show is product market fit.

Pablo Srugo (00:02:20):
Do you think the product market fit show has product market fit? Because if you do, then there's something you just have to do. You have to take out your phone. You have to leave the show five stars. It lets us reach more founders, and it lets us get better guests. Thank you. Andrew, welcome to the show.

Andrew Rubin (00:02:34):
Thank you so much for having me, Pablo.

Pablo Srugo (00:02:36):
So you launched Illumio back in 2013, so over 10 years ago. You went kind of out of stealth about a decade ago. You've raised $600 million. 800 employees to date. And your kind of catchline, we were talking. You haven't raised money in the last four years and don't plan to anymore. So we can all kind of infer what that means or will mean. But I think clearly you've built a pretty massive business, but it has been like a long road. And I say that more than anything to point out that it kind of usually is. You know what I mean? That's just the norm. You read about zero to 100 million, you know, all the time, and everybody's trying to outdo the last one that did it as fast as whatever. But those are not, even of the success stories. Those are the exceptions. So anyways, we'll go through all of that. But maybe just to start. What is Illumio? What does Illumio do? 

Andrew Rubin (00:03:26):
What we did is we built a graph. And that term, when we started talking about how we were going to build Illumio about 10 years ago. That term was not one that was often used. Now, literally everybody from Illumio all the way to Microsoft talks about the future of security is really being based on a graph. And a graph is sort of a very fancy and unusual way of describing a database that allows you to collect a lot of information to understand not just the things in the graph. But the relationship that they have to one another. And then what we did was we built two things on top of that graph, now more and more powered by AI. The first, and what we're known for, is obviously delivering zero trust segmentation. And that's what the company's been built on. We'll talk a little bit about what that means, but that's one of the two outcomes of having this very powerful security graph. The second one, and much more recently, is we deliver now an analytics layer that we call "insights" that allows you to go inside. Ask questions of the graph. Understand things that may be happening in your environment that, from a security perspective, either are risky or potentially risky. And so the way that we think about Illumio is we think about it being built on top of this very powerful security graph and then allowing our customers to do two things. Look inside and see what's happening in their environment. And the second one is writing policy to deliver zero trust segmentation. And I'm happy to talk about one or both of them, go into detail. But that's really the Illumio story underneath the covers.

Pablo Srugo (00:04:55):
Well, I think, you know, for people that are out, kind of, outside of security. Which is frankly most people just in general, but certainly most people like listening. Everything will make sense maybe as we kind of go through it. So maybe tell me this. When you started in. What's kind of the origin story? You know what I mean? When you started in 2013, what were you doing before? Where did the idea come from?

Andrew Rubin (00:05:12):
Yeah, so myself and the co-founder of the company. Who was our CTO for a long time. He and I knew each other prior to starting Illumio together. And we both had a similar view of the world. Which is that most of the traffic that runs through most of the networks inside of an enterprise or a government organization. It doesn't matter who it is. How big or small, what they do for a living. Everybody's got these networks that have been built over the last 40 or 50 years. Traffic runs through the network and then goes to the outside world and obviously comes in from the internet into the environment. And everybody's relied on literally one device to essentially control how that traffic can and can't move through the environment. The device is called the firewall. It's literally 30 or 40 years into its life, still one of the biggest categories in TAMs in cybersecurity spent on the planet. There's a couple of very large companies that have been built delivering firewalls. I'm sure even if you're not a cyber person, you've heard of Palo Alto Networks or Checkpoint, who really is credited with inventing it. And the reality is that that model, that entire theory of putting a firewall in a network. It worked super well for a long time because the network was in the data center. There was no such thing as cloud or public cloud. There was a very, very good alignment between the firewall and the environment that it was put in to protect. And then, give or take about 10 to 15 years ago, depending on when you want to start the stopwatch. All of a sudden, virtualization came to life. Cloud started to become a very real thing, and not just cloud to run a SaaS app, but cloud to run your infrastructure. And all of a sudden, this device no longer seemed to fit as neatly and as perfectly as it did in the past. The origin story of Illumio was we said we want to do in software what the firewall's been doing in hardware. Except we want to make it so that the software can do the job anywhere. The data center, the endpoint that I'm sitting in front of, called the laptop. We want to be able to do it in the public cloud and the private cloud, and we want one software platform to be able to deliver these outcomes across all of this hybrid universe. And that was sort of the theory behind what are we going to do differently than what's been done for decades before. We're going to take this hardware-based model that lived in the data center, and we're going to turn it into software and make it live anywhere.

Pablo Srugo (00:07:40):
Maybe just a very baseline question, but in simple terms. How does a firewall work?

Andrew Rubin (00:07:44):
Sure, so there's obviously the traditional answer. And now fast forward to today. There's a very different answer based on segmentation. The theory of a firewall, and you don't need to be a cyber person or even a technology person to understand it, is. You put a device basically in the middle of the road, and it acts as not a speed bump. But literally a brick wall, except this brick wall can be programmed to say if a car comes at it that fits a certain description, the car can pass through the wall. And if a different car comes at it that doesn't fit the description that's been pre-programmed in, it hits the brick wall and it can't go through. And so the way to think about it is the firewall's job was literally to control what could and couldn't talk to each other inside of a data center or a network. The more modern version of that is, and there's an analogy that we've used since the beginning of Illumio to describe it in very non-technical terms. If you think about the way that a submarine is actually constructed, and I sort of joked that I could give my 12-year-old daughter a pencil and a piece of paper and say, "Draw me a submarine." And even though she's never built one or been on one, everybody is going to draw the same picture. It's that long tube. Most of the time you put the little periscope on top of it. But there's this one thing that, once you say it, you realize it's kind of part of the generic picture. Every submarine is divided up into compartments. Those compartments are actually there. They serve a purpose, which is if the boat is underwater and it springs a leak. Instead of the entire boat flooding and all of the very bad consequences that would happen. If you spring a leak at the front of the boat, you simply close that compartment. That one compartment floods, but everybody inside stays safe. You bring the boat to the surface. You fix the leak. The boat goes back into service. And relative to that catastrophic outcome, that's a pretty good outcome. Segmentation today is literally designed to do the exact same thing, which is to say, look, we live in a post-breach world. Every organization either has been breached or they're terrified they're next on the list. And they rightfully should be because this is no longer an anomaly. It's not if, it's when. If the biggest companies in the world and the most sophisticated governments can't keep their things safe 100% of the time, nobody should assume that that's a safe bet. What segmentation does is it builds the compartments so that if one part of your environment gets sick, you simply close that compartment. And yes, a handful of things will get sick. It's not perfect, but it prevents the catastrophe from happening when a few things infect everything. So it's sort of the modern version of the firewall with a lot more intelligence. And again, the ability to do this across a very, very diversified landscape.

Pablo Srugo (00:10:28):
And walk me through. What were you doing before Illumio that you even noticed all these things happening?

Andrew Rubin (00:10:33):
So both my co-founder and I came out of the firewall space. In my case, it was all network security. So firewall, IDS, IPS, a whole string of acronyms that basically mean looking at traffic, understanding how it moves, and when it should and shouldn't be allowed to move. My co-founder was in a very large firewall company here in Silicon Valley and was an architect. So that means that he was writing code and architecting systems. I think the thing, though, that's so much more important than what we were actually doing in our day job was that when we got together. He brought the deep technical and architectural point of view. And I've spent my entire career, including at Illumio. More at Illumio than ever before, in customer-facing roles. So sales and sales engineering and talking about how products are implemented and what competitive landscapes look like. So he was able to bring the technical problem and, obviously, a potential solution to the table. And I was sort of, we use a term around here at Illumio called "the voice of the customer." I was essentially the founding voice of the customer. I was describing the problems I heard customers talking about when they tried to take their firewall and plug it in public cloud. And it just didn't make sense or work. That was the genesis of the conversation that became Illumio.(Context: IDS (Intrusion Detection System) monitors network traffic for suspicious activity and alerts administrators, while IPS (Intrusion Prevention System) not only detects threats but also takes action to block or prevent them.)

Pablo Srugo (00:11:50):
When customers are trying to bring the firewall to cloud environments. What breaks? What were some of the symptoms of the issue?

Andrew Rubin (00:11:56):
Initially, way back when. It was really two, I'll say, fairly simple things to describe. It turned out to be unbelievably complicated to solve for them. One was just the architecture. A firewall literally has been delivered as a hardware box for decades. You literally plug network cables in the back of it, and you try and shove traffic through it. And in a traditional old-school data center, I wouldn't say that that was ever really easy. But at least there were solid operating models for how to do it. When you go to places like the public cloud. You can't ship a box to Amazon or Microsoft and say, "Here, please plug this in for me." It doesn't work that way. So there was truly a fundamental breakdown of the architectural model that everybody relied on. So there was a problem that needed to be solved there. The second thing is, and again, it sounds so simple and obvious when you say it. But solving for it was much harder. The network world and the cybersecurity world has been based on something called IP addresses forever. And networks still are based on these IP addresses underneath the covers. But in worlds like the cloud or in the developer world. Nobody talks or thinks about the IP addresses. They think about the application, or they think about the business process. So if you think about a bank that has ATM machines. There's literally an application or a set of applications that allow those ATMs to do their job and figure out how much money you have in your account versus me and mine. So when you go up, you can check your balance. All of this is happening, obviously, in the background. The problem is that when you talk to people today. They don't talk about, well, what IP address does this server have on it that needs to talk to that server over there? They talk about, well, this is the application that allows us to check the balance of the accounts of our customers, and it has different tiers. And those tiers need to talk to each other in certain specific ways. So the policy and the way you describe your firewall and segmentation had to change as well. And again, two fairly simple things when you say.

Pablo Srugo (00:13:59):
Because firewalls were fundamentally based on IP addresses, like, this IP address goes in, this one doesn't, things like that.

Andrew Rubin (00:14:04):
Fundamentally and entirely both. And the world was moving away from that, not from those addresses. But from writing your policy and describing how you wanted your environment to live and how you wanted to protect it. People were moving into the same thing that they do in the cloud. Which is you have tags and labels, and you describe things in much more human and natural terms as opposed to these clunky addresses that mean very little except to a small group of people who are running the infrastructure. By the way, Pablo, by no means am I saying those addresses are unimportant or that infrastructure is unimportant. The whole world runs on it. But security has moved into a place where the security is much more aligned with the way we build things. The way we run them, the way we describe them. And that had not happened. And so Illumio really was founded on building this architecture that works everywhere. And building a policy model on top of this graph that allows people to describe policy the same way they talk about the things they're building and running to make the business run.

Pablo Srugo (00:15:04):
How? You know, one question I have. Maybe it's not really a tangent, but it's a bit of a tangent. But when I look at a lot. One of the funny things of doing these podcasts and looking at companies that are 10 to 15 years old and then are successful. And you're obviously looking at kind of the successful group of companies. Is that in every single case, all the tailwinds played out. So, in your case, cloud did become big. You know, workloads did move to the cloud, and so on and so forth. And looking back, it kind of seems obvious. Like, I've spoken to other companies that, you know, rode, let's say, the mobile wave or, you know, things that. Speaking of Mercado Libre, you're like, "Yeah, of course, internet penetration will go to 100%." Of course, people will get mobile phones, and they buy everything online. And you are there, and you benefit. When you were starting, though, like, take us back to that, you know, 2013-ish, 2014, maybe even 2012. That time period, and you're telling people about the firewalls are not going to work in this future world and you got to do this way. Was this like generally accepted wisdom? Like, yeah, of course, no brainers, no matter who's going to do it and how, or were you a little bit of like the crazy one saying things that many people thought were just kind of unimportant or nonsense even?

Andrew Rubin (00:16:09):
So I actually think it's literally the single most important topic in question that we're going to talk about today. Because you said something debating about everybody thinks that it's zero to 100 million in an hour, and then it's a billion two hours later. And one of my favorite expressions, credit to whoever said it first, was, you know, it's the overnight success story a decade in the making.

Pablo Srugo (00:16:29):
Yeah, that's right.

Andrew Rubin (00:16:31):
Because everybody thinks these things happen overnight. But in our case, I actually think that it's much more fundamental. And the reason I say that is. I've actually talked about this more and more openly and more and more publicly over the last few years. Everybody starts the company and assumes that, at least in tech. Assumes that if you build something that's technically really interesting, certainly really difficult to build, that the whole world's going to figure it out and figure out that they need it the next day. And there are a few stories where that product market fit and go to market fit align on day one. They are very, very far and few between. And the reality is that I believe now more than ever, having been a part of helping to build this company. I believe that at the end of the day, the one thing that's out of your control controls more of your destiny than anything in your control. Which is the market adoption and where the market is in adopting. So you have to start by sort of noting, again, something really obvious. But ironically, something that I know they never taught me in B-school, and I don't think it's anything that anybody really talks about enough. There are two kinds of markets. There is an incumbent market that's ripe for disruption. And then there are literally brand-new markets that are built into a space where, for some reason, there's a brand-new problem that suddenly exists and needs to be solved. And the incumbency one is not a little easier. It's not a lot easier. It is fundamentally a different motion than the second one. Because if there's billions of dollars of product deployed. It's not just about the fact that the budget is there and the TAM is already there. It's that procurement has benchmarks for what to buy. It's that the POC is understood because somebody did one on the previous generation product. Its operating models exist inside of the customer so that when they buy this new thing to replace the old thing that may be legacy and maybe didn't innovate the way it should have. They already know how to operate it and who owns it internally. In other words, the infrastructure for the entire ecosystem is already built. Now, I'm not saying that means that starting a company to disrupt a big incumbent is easy. What I'm saying is that the journey for product market fit and go to market fit is a lot easier because the infrastructure has already been laid down. And I'll use a space like the firewall as an example. You look at what Palo Alto Networks has done. And of course, it's impossible to argue with how wildly successful the company has been. And I'm sure it was incredibly difficult to build every company at scale is. But Check Point had pioneered the firewall market and had an installed base all over the world before Palo Alto was ever the name of a company. And then when Palo came in and said, "We think we've built a better mousetrap, and we want to build and show you why we can disrupt the one you already have." All of those previous questions have been answered. Now, again, I'm not saying it's easy.

Pablo Srugo (00:19:24):
But it leads to like liquidity. That's almost the thing that comes into my mind. It's just like once you do have it. Everything around it is set such that you can just kind of make your way through that market, you know, very, very quickly. You have to execute all these things. Nothing's easy. 

Andrew Rubin (00:19:38):
Absolutely.

Pablo Srugo (00:19:39):
But the setup is there, right? It's kind of like selling a stock. If you're going to sell it for 10% less than market, you click a button. Somebody's buying it. But if you want to sell some random antique you have in your house, it could be super valuable. It could be great, but you're going to have to go and find that market somehow. It's going to be a lot more effort. And so that's similar to a new market. There's no infrastructure.

Andrew Rubin (00:19:55):
It's absolutely right. And I'll go a step further, which is you have to do a huge amount of evangelism and education. And that's the piece. That's why I said I think it's the most important question. When we started, "segmentation" wasn't a word that anybody was using. Gardner didn't write a report with the word in it until two years ago. And we had already become a company of over 500 people. We had customers all over the world. Obviously for us, we think we're still in our very early days. But the point is that when you are going out into a market that doesn't exist. You are literally evangelizing, not you. You're evangelizing the problem. You're educating on why the customer even needs to think about, let alone care. Then when they agree that maybe it is a problem they want to solve. There's no operating models or playbooks for what to do or how to solve it. It is a very, very, very different and difficult road. And in our case, what I will say is that when you try and do that in the infrastructure. When you're trying to sell something to someone that literally controls how their environment behaves. And if it goes wrong, could potentially break things. You've probably now stacked a bunch of pretty hard things on top of each other. So it doesn't mean that you're any less right about the problem. It doesn't mean that one day the mass market won't adopt. If you're a fan of Jeffrey Moore's adoption curve. There's a reason why 10 or so percent. I think it's 13 to be an early innovator and early adopter. And then there's that chasm where they say things go to die because if you can't get to the majority of the market, it's not really a market. But we've lived that entire journey, and it's been defining for the company in every way. And those tailwinds you talked about, I would argue we only started to get them very recently. despite whatever it is that we've built life to date.

Pablo Srugo (00:21:42):
Did you go? I'm curious, like, what your first step was. Did you raise a rounding? The broader question being. Did you go into it eyes open, knowing it's going to be a slow grind, we're going to have to evangelize, whatever, or did you go into it like, we've got the thing, let's get it, and then you kind of realize, holy shit, it's going to take a long time until people really get what I get.

Andrew Rubin (00:22:01):
So there's a running joke here. I'm sitting in our Sunnyvale headquarters today, and there's a running joke amongst the team here. They've heard me say it. If somebody had sat me down and described what the journey was going to look like, I might not have started the company. Now, I say it's a running joke because, number one, I'm pretty sure I would have started it anyway. And number two, I'm incredibly thankful that I didn't know. Naïveté is sometimes bliss. And obviously, I couldn't be more excited about where we are on the journey today. And as I said, I think we're just getting going because we've been doing this without a market for most of our life. And now I very much believe there is a market. There is no doubt about it that we went in not understanding what we were doing. We understood the technology, and we understood the domain very deeply. And that was, I think, one of the two things that saved us early on was. That we weren't making up what we were trying to do as we went when it came to the product story. We had a very sharp, and I'd like to think a pretty educated, point of view on what to build and why. What we didn't understand was how hard it was going to be to get the go-to-market right in light of not having a market. We assume, kind of like you just joked, Pablo. We assume, well, everybody's going to hear it. And of course they're going to get it in five minutes. Ten years later, I think we might be starting to be right about that. But I'll also add one thing, because this is another one of these little anecdotes that's made its way around the building here. I really, and again, so much of this is just because we've lived this journey that we've been on. I've sort of taken to saying that the difference between being very, very, very, very early in something and being too early in something, T-O-O, of course. It's really only one word. And the word is actually not "time." It's bankruptcy. And the reason I say that is because we all know, especially in technology. There are ideas that come before their time all the time. Somebody will start a company that's way ahead of the curve. That company will go bankrupt, disappear, go away. Five years later, a different group comes along. Starts something that essentially is the same thing, and they knock it out of the park. And that's simply because the market wasn't there the first time around. So if you want to be very literal about it, you can be very, very, very, very, very early. You can stick 20 very's in front of that. Just don't run out of money. And the two ways to not run out of money are fundraising and revenue. Those are always going to be the two sources of capital. Revenue is a lot more fun to generate, especially if you can scale it. But fundraising fills that gap while you're scaling your revenue. And so for us, you asked the question about raising. We went all in from the beginning. We knew, again, back to what we did know. We knew the problem was a hard one. We knew the technology was going to be, I'll call it "deep tech." Meaning we were going to need a lot of engineering horsepower to get it built and out the door. We raised, in the first six, seven months of the company's life, over $40 million.

Pablo Srugo (00:24:55):
Whoa.

Andrew Rubin (00:24:56):
The team hadn't hit 20 people, and we already had $40-plus million in fundraising. And basically, the month we started generating revenue two years later, we raised $100 million round. And back in 2015, you know, there were not a lot of enterprise companies.

Pablo Srugo (00:25:12):
I was going to say that's not that common. 

Andrew Rubin (00:25:13):
It was. 

Pablo Srugo (00:26:14):
These days there's AI. There's people that, you know, they leave open. They raise a billion dollars. This is a new world. It was not happening back then.

Andrew Rubin (00:25:20):
It was a very, very different landscape back then. And so we were fortunate to be able to raise early, to raise aggressively. And one of my many mentors, I remember, said to me at one time after we had raised the $100 million round. And we were sort of getting a clue that this was going to be harder and probably take longer than we thought. We had no less conviction that we would have a shot at being right in the end. In terms of the problem being a big one. But we definitely were starting to get a sense that it wasn't going to be as easy as we thought. And I'll never forget, one of my mentors said to me at the time. The one insurance policy that you have when you're right, but you don't know how long it's going to take, is cash. And I never forgot that. And, you know, the whole thing about trying to gain dilution. Sell a tiny little bit less of the company. That's great, so long as you don't go broke. And so we took the attitude that we were going to raise. We were going to raise aggressively, and we were going to keep our heads down and just build, build, build. And look, I'm the first to say it, it took a lot longer to really have any kind of data-based conviction as opposed to the "we believe" conviction. It took a lot longer to get the database conviction. The database conviction that the market was really becoming real and opening up. We definitely waited a lot longer for that feeling than we thought we would.

Pablo Srugo (00:26:38):
You know, I will add one thing like you did. You mentioned, you know, to stay in the game when very early, however very early you are. You need to have money. You need to not go bankrupt, obviously. But I think the other thing you need, and I think this is lost, especially like, for example, it was lost on me when I was a first-time founder. Which is, the power of, you know, you want to call it passion, conviction, you know, whatever you want to call that. It's like sometimes, especially as a first-time founder. You just want to start a company so bad. At least for me, I was like, I don't really care what it is. If I hear a really good idea, let's do that. You know what I mean? I just want to do a business. It sounds stupid, but I think a lot of people think this way. And you don't realize. Even if you're right, it might just be that you're right in 10 years, and you have to wait it out. And obviously things are happening in between. You get signals. It's not like nothing happens. Then you raise all this money. But even though you get signals, you're not really there for a long, long time. And so if you don't have a serious level of conviction in whatever it is you're doing, you know, at least like in the problem, if not the solution. You're going to give up early, almost for sure, unless you just hit it out of the gate. You're probably going to give up way before because all that market data is going to mean more than maybe it should. And you're going to say, "Well, you know, if it was a real thing, we would have already, you know, we'd be here, not here." And so, and then you don't make it whether you go bankrupt or not.

Andrew Rubin (00:27:55):
I couldn't agree more on the number of times that I've had an entrepreneur share their story with me where they say, "We were slugging it out, and it was just brutal for X number of years." It's never weeks or months like everybody thinks. And then something changed in the world. And essentially overnight, we went from being interesting to being insanely and incredibly relevant. You know, if you're not playing the game, you can't win it. And so the reality is that, yes, you do have to look at the data. You do need to look at the signals. Sometimes they're very early. And very weak and very faint. And sometimes they're right there up in your face, and you know exactly what it's telling you. By the way, good and bad. I don't think that walking around with conviction that's based on nothing other than belief is a good strategy. Because you can throw a lot of good effort and a lot of good money after bad if you walk through your sort of decision-making that way. But I also believe for a fact that an entrepreneur's number one job is to absolutely be that sort of voice of conviction in the room. The number of times where we debated, should we staple features on in the early days just because those features might make it easier to sell the product? The problem was every time we had the conversation, we said, Yeah, but those features have nothing to do with the problem that we started the company to solve. And what we're going to do is we're going to end up being distracted and diluting our story to get some short-term win that we don't even know if it's really going to be a win. But we know in the long term it doesn't make sense. So either we're convinced that we're right in the long term and we're going to stick to it, or if we think we're wrong. We should have that conversation and figure out what we're going to do to pivot, change, or go away. And I just think the ability to continually have that intellectually honest conversation is so critical. When you're doing it in a market that doesn't exist in a category that's not mature.

Pablo Srugo (00:29:50):
How did you raise that $40 million, you know, six months in? Because, I mean that's a hard thing to do.

Andrew Rubin (00:29:56):
Yeah, you know, it's so funny because on one hand it feels like yesterday. And on the other, I know certainly, based on feeling a little bit older, that it was actually quite some time ago. You know, we raised $8 million to start the company. Andreessen Horowitz took the bet on us that literally, and I am not exaggerating, I can't say hundreds, plural. I can absolutely say many, many, many dozens of venture capitalists, including just about every logo on Sand Hill Road, both 10 years ago and today. They all said no. Or they said, "Thanks, it's interesting, come back later." Which is no when you're asking for money to start a company.

Pablo Srugo (00:30:34):
And did you have a network to get in front of a16z, or you went cold? How did that happen?

Andrew Rubin (00:30:38):
So ironically, a16z was actually the one that I couldn't get to. And I had been out trying to raise. Let's call it from January of 2012 all the way through until October, November, still had no luck, lots of no's. And it was a meeting, ironically, with a partner at a corporate venture fund, not a traditional VC, but a CVC. I knew they would never write the check, but we knew a handful of people in common. And he had done some cyber in his previous life when he was at a Sands Hill Road fund. And I went and I pitched him not for the money because I knew that the CVC wouldn't write a startup check. A true startup, check in our case. But I said, "Anybody you can think of." And the first person he mentioned was actually a partner at Andreessen. Now, of course, back then Andreessen was 30 or so people in the whole firm. I mean, they were a startup compared to what they are today. And he made the call. He actually called the partner and said, "I'm looking at something really interesting, it's right in your wheelhouse." I went over. This was around Thanksgiving of 2012. And after 11 months of begging and pleading for money, and I can't say ever seriously considering giving up, but definitely thinking about what are the drop-dead dates. And the alternatives if we can't raise a real round. I had one meeting with a partner. It lasted for less than an hour, and two weeks later, they had signed a term sheet to give us $8 million to start the company. And it's an amazing story that I will forever be grateful that that random connectivity existed. It also is something I believe in very deeply. Which is you get in cars, you get on trains, you get on planes, and you go sit face to face. And you build real relationships because you never know where they're gonna come in handy. Where they're going to add value. And by the way, in which direction, right? Because if it's a real relationship and partnership, it's bi-directional. That was one of the luckiest strokes that we had. We finally got the money, and then we started the company. And I will say, it's one of those things that we didn't plan. Being so deeply in stealth and literally having a homepage for the first two years of the company's life that had nothing on it but literally a fully black screen with a white logo of Illumio. That mystery built really quickly. We were lucky to hire some really well-known folks out of places like VMware that helped the mystery as well. Every time somebody asked what we were doing, our answer was, "We don't talk about that." And six months later, I got very lucky again through the network. The former CTO of VMware had become a venture capitalist at General Catalyst. And we were effectively the first investment he made. And we were pretty open with him, given his background as CTO at VMware. We knew he would get it right away. And once we started describing it, he got it even faster than right away. So we were lucky enough to partner with Steve Herrod from General Catalyst. And he had a partner named Hemant who now runs General Catalyst. And they were kind enough to take a big bet on us and led what ended up being about a $35 million round. And then we spent another year and a half in stealth, barely making a dent in the capital because we were literally just an engineering team. There was no go-to-market. There was no marketing. There was just a website with a logo on it. 

Pablo Srugo (00:33:56):
You love this show. You don't want to miss the next episode. Why would you? So hit that follow button. Trust me, it's in your own best interest. So we'll get into that. But my last question is just on that fundraise. a16z, like they must have obviously seen something in you guys. They must have believed in you, but they probably also just understood the problem. Like, was it a space they were already looking at or just when you described to them and kind of just made sense?

Andrew Rubin (00:34:17):
Yeah, it goes back to that evangelism and education thing. So the only way that you can get around evangelism and education, and I don't care if it's an investor or it's a customer prospect on the other side of the table. They have to already have the deep expertise and background. So the partner at Andreessen Horowitz was actually a gentleman. He's no longer at the firm. He retired years ago, but his name was Scott Weiss. And Scott had literally started in the same role that I'm in at Illumio. He was the founder, CEO. Scott had started a company called IronPort. Which was a network security company. Built it very successfully, sold it to Cisco, I think for about a billion dollars. Scott needed three minutes, if that, and he already knew exactly why we were building what we were trying to build. Steve Herrod, obviously living as CTO of VMware, deeply, deeply understood the problem space. And again, just like Scott, needed maybe three seconds to understand why we were doing it. And obviously with Steve, we were six months down the road. So there was more to show. Scott got it off of a set of slides in a matter of minutes. But it really does come down to, we were never gonna, in my opinion. We were never gonna raise the capital for something this hard and this new from what I'll refer to as a generic VC. And by the way, some of the smartest generic VCs. In other words, when I say generic, people who do all sorts of investments. If you didn't have really deep domain expertise. We were probably speaking some combination of French, German, Spanish, and Latin all mixed up together.(Context: IronPort was a cybersecurity company known for its email and web security appliances, which helped protect organizations from spam, malware, and other online threats before being acquired by Cisco in 2007 for in a deal valued at $830 million, comprising both cash and stock.)

Pablo Srugo (00:35:46):
Well, for what it's worth, this is some of the kind of softer. I mean, the true signal is customers buying your stuff. But in terms of the softer signals. VCs who get the domain, like the deep domain expertise is where you're building, who take large bets, is one of those things you would kind of add on as you're kind of challenging and testing your conviction on the way to true success, is like, okay, you know, C2OVM where, you know, Scott, et cetera, et cetera. Yes, they agree with this view, you know, and that kind of keeps you going the next year and the next year and things like that, right? They start to add up.

Andrew Rubin (00:36:15):
It does. And, you know, the expression. Everybody knows the expression about mistakes. Which is never make the same one twice. And my add-on to that is what you're going to make at least a couple every day. So number one, don't make the same one twice. Learn from it and fix it. And number two, just don't make one that kills you. In other words. Mistakes come in all forms, all factors, right? The really, really big ones and then the really, really small ones. The hope is that you learn from every one of them. Really, really want to try and not repeat them when you can. But obviously the other piece of it is don't make one that kills you. So if you know you're building something that's going to take longer, be harder, and cost more money. Don't get focused on dilution. Get focused on raising the capital you need. Because if you run out of money, it won't matter how much of the company you own. It won't matter how right you would have been in the end. You're broke, and so getting focused on what is the real problem that you're trying to solve and, therefore, like, really being clear on that problem statement, it's amazing at how you can start testing the thesis of am I focused on solving the right things? Am I focused on really the right things that are gonna move the needle as opposed to just creating activity for activity's sake? I would argue that our fundraising early on. We didn't understand that, and I made that mistake big time. I thought activity will equal money, funding, because everybody talks about, oh, well, I pitched 100 VCs to get to the one. But sometimes pitching 100 is actually no better than pitching eight if it turns out that there's only three that really are going to get your pitch. The other 97, it's going to make no difference at all. And that's a mistake that I didn't learn from fast enough. And believe me, after we got the A done with Scott, I had a very different philosophy on fundraising going forward.

Pablo Srugo (00:37:58):
And so what do you do in those first couple of years? Maybe first, question, how many people do you hire with that 40 million in that first year or so?

Andrew Rubin (00:38:06):
So when we raised the Series B, let's call it six months or so after we founded the company. We were about 20 people. That gives you just that first six-month hiring plan. It was all product and engineering and literally me. And then from there, obviously partly driven by the funding. But much more so because we were like, wow, the engineering lift on this is going to be a lot bigger and heavier than we thought. I think when we came out of stealth, so call it at the two-year mark a little bit more. I think at that point we were about 50 people, just under the 50 mark. And then from there, we obviously started what was, I can't say, a steady acceleration because it had fits and starts. One thing that I'm incredibly, incredibly proud of is that I can say that I'm working on a team for a company that literally has never done an economic driven layoff before. We've never done a riff in the life of the company. There were some times, obviously, when COVID first hit and the whole world was terrified about what was going to happen. That obviously we had those conversations. But the team has just done a really great job of being very judicious, being very deliberate, and being very thoughtful about the fact that we knew that our rocket ship. If you want to call it that, looked more like one that did this and then this and then this and then this as opposed to this. And so when you feel like you're going like this. It's very, very easy to just go higher, higher, higher, fundraise, fundraise, fundraise, hire more. The problem, of course, is that the second that this goes like this, not even like this, just a tiny bit off. All of a sudden your burn goes through the roof. It's very hard to fix that without layoffs and rifts because almost all the money that a software company spends is in people. It's the only expense big enough that you can move the needle. We were very thoughtful once we realized that our journey was going to be a little bit longer. Maybe a lot longer, probably harder. So we've always been accelerating, but we've done it more cautiously than most people from the outside in would expect.

Pablo Srugo (00:40:09):
And with 50 people, did you have customers? Did you have revenue? Or this is all pre-revenue?

Andrew Rubin (00:40:14):
So when we came out of stealth, that was the day that, arguably, the revenue train began to leave the station. I think one of the things that we got lucky on, and it really helped us enormously. Was that the problem that we were solving tended to be. Much less so today. This statement is nowhere near as true now as it was when we came out of stealth. But certainly back then, the early adopters and the early innovators who were willing to look at segmentation. These were the biggest companies in the world, literally not figuratively. So think the biggest banks around the world. The biggest insurance companies. Partly because they have very deep technical expertise. Partly because they run very large critical infrastructure. Partly because they're more heavily regulated than most other companies and because they have a rightful paranoia about what happens if they get hit. And so, our first customers were some of the biggest banks in the world, and fortunately. They believed in us and the problem we were trying to solve enough that we didn't do a lot of $50,000 or $100,000 deals in the beginning. Quite frankly, most of our deals were seven-figure deals. And so we were able to land big deals in very large customers. It became an operating model that let us grow revenue. It was something we knew eventually would have to broaden out. You can't be a public company, or I should say it's almost impossible to be a public company only selling to the Fortune 100. At some point, you want the diversity in every way. Size of customer, industry of customer, geography, obviously. But in the beginning, we were lucky that we were landing very big deals in very big customers, and that gave our revenue a lot of acceleration. Certainly still not enough to be profitable, not enough that I didn't have to go out and raise hundreds of millions of dollars more after. But it was a great way to get out of the gate to land some of these very big logos and then have a seven-figure PO attached to it from very early on.

Pablo Srugo (00:42:15):
I've spoken to a few founders who were in a similar setup as you in that they're selling to large enterprise. And it's kind of a deep-tech kind of solution. Like, oh, operating on a hard, double hard mode, you know, like startups are already hard. This is like triple hard because you have hard startup and then deep tech. Which is harder, and then selling enterprise, which is, you know, really hard, mainly because of the mismatch of like timelines. You know, like for a startup, we usually. What do you get done this day, this week? This month is already like long-term thinking. Whereas an enterprise, it's like, I'm not talking to you today about today. I'm talking to you about next year and the year after that. And so there's this mismatch in time to make things really hard. All that to say, maybe you can walk me through your first customer. How do you go from stealth company developing product to meeting them to, I'm assuming POC, like what was that like to finally that seven-figure PO? Like, kind of, end to end, because I, you know, just imagining from the perspective of early-stage founder that is in this selling enterprise kind of mode. It's not an obvious place. Like if you don't come from selling enterprise, it's a completely new world. So it will be great to kind of walk through that end to end.

Andrew Rubin (00:43:26):
Yeah, absolutely. So first of all, again, a huge shout-out to Andreessen Horowitz from the very, very beginning. Because they had built this model that now so many of the VCs have rightfully copied. But this executive briefing center, what they called their ABC, and what Andreessen, you know, did that was just the value was literally indescribable in the early days was. They would bring out the CIOs or the chief security officers of these huge companies. Companies that most of us as founder CEOs or founders would spend years trying to get in front of and most of the time would strike out. And what they did was they simply brought them out to California. They brought them to their office on Sand Hill Road. And the pitch to those folks, to those CIOs and CTOs and CISOs, was coming out and spend the day. By the way, it's not the worst place in the world to spend the day is sitting in Andreessen's offices on Sand Hill Road. And what we're going to do is we're going to get a bunch of our interesting companies and the founders to come in and do, like, a 20 or 30 minute pitch on what they're building. And by the way, most of these are going to be things that are either in stealth or just came out of stealth that you've never heard of. And in stealth, you really have never heard of. And I am not kidding when I say this. I lived in that EBC days on end in the first two years.

Pablo Srugo (00:44:43):
How often were they doing this?

Andrew Rubin (00:44:44):
Oh, I mean, back then, and I certainly would imagine the model is even larger and more structured today than it ever was back when we were a startup. But back then, I was probably in their office doing at least a few EBCs a week, every single week from the week that we started. It was unbelievable the access that it created and the conversations we were able to have. So keep in mind what was fun about it. And I say "fun" as in it was really fun. But what was fun in terms of how it helped the business was. I would walk in the room, and the first thing I'd say to every one of these teams that I would meet. Because most of the time it wasn't just one person, we'd walk in, and GM would have the entire technology leadership team in that conference room. We would walk in, and we would. First thing I'd say is, look, I just want to be really clear. Everything that we're showing you is confidential. And I couldn't ask you for a purchase order at the end of this meeting. Even if I wanted to, because we're not going to deliver the software for another two years. And they would laugh, but it actually was a very disarming comment because now it wasn't a sales pitch. We really wanted their feedback. And a few of them got excited enough about what we're working on. They kind of became design partners. So they were actually engaged with us outside of the EBC over the course of those couple of years. But what it meant was by the time we actually pulled the cover off of that website and, you know, the day went live and it said, "Here we are, and this is what we do." I had probably spent over those two years. 50% of my time in front of prospects. I can't call them customers because none of them were paying us yet, but let's call them prospects. I had a Rolodex full of these folks. Some I had met with many times. I started traveling for Illumio, call it six months into the company's life. Because the engineers and the product folks were all back in Santa Clara at that time, building what would become version one of the product. I had nothing to do. I had raised my $40 million to give to the company and say, Here you go, go build a great product. So I said, you know what, I'm going to start traveling, and I'm going to go meet with these customers in New York and London. I wasn't going to Asia yet because that felt a little too far afield.

Pablo Srugo (00:46:48):
Were you going to conferences and stuff, or you were leveraging these contacts and then going to see them?

Andrew Rubin (00:46:52):
Yes to every version of that. My view was I had one job to do, which was to get out there and meet with as many people that could help us to shape the product story as possible. And that brings us to this other part of your question and the other thing that you said, which I could not agree with more. We had to understand the timelines we were gonna be operating on if this was really the customer base that we were going to. And I say this in a totally joking way. That's why I'll do the air quotes. We were going to be stuck with this customer base for a while. And the reason I say it in those words is, back to what did we know going in. We knew the problem. We had a very sharp view on what we wanted to build. We didn't know if our first customer was going to be a local bank in Sunnyvale with three branches or JP Morgan Chase. And obviously selling to the local branch here in Sunnyvale is very different than selling to JPMorgan Chase in every imaginable way. We figured out during that stealth period that it was very likely that if we were going to sell this software to anybody out of the gate, it was going to be the biggest. We were pretty confident that we could deliver against that requirement, but it meant that everything had to be worked against a plan of what happens when it takes a year to get the first contract. Because you're not getting it in three weeks. And so I went out, and I spent that year and a half or so running around the world. Building as many contacts as I could, obviously updating very regularly on the development progress. And when I say I did it, it was myself, our head of product, my co-founder, our CTO. We were lucky that in some cases, the customers or the prospects got so excited. They'd say, why don't you come in and spend a day, and we'll just go super deep on this. Show us where you're at. We'll give you our feedback. And we just took advantage of all of that. But as I started to say, that brings us to something that's not thought about or described. Everybody talks about PMF, and rightfully so. I can't have a company if you don't have a product that fits the market. But the other version of that statement, which is equally true and equally important, is you have to have go-to-market fit. You have to understand your go-to-market the same way you understand your PMF. If you're gonna sell to Citi and JPMorgan, it's not just about how long it takes. How do you have that conversation? Who really controls the money? Where do you have to go in order to get the money? Right? These are IT organizations that have tens of thousands of people. If you think that everything from budget cycles to politics isn't part of that conversation. So the same way that we say, why is a product such a great fit for a market? Your entire go-to-market has to be built to be able to exist and thrive in that environment. And so I was trying to figure as much of that out while the team was really focused on how do we get this product to something where we're going to end up being right on the PMF side. And I spent all that time trying to understand what is our go-to-market fit going to need to look like to sell these big deals to these big customers.

Pablo Srugo (00:49:57):
And who, like, I don't know if you can name your first customer. But I'm less interested in the name as to, you know, that kind of journey. Because on the one hand, what is surprising and not normal. Makes tons of sense, but not normal, is the quantity maybe of conversations, and the frequency of conversations that you were having. I find a lot of enterprise, and maybe it's because of lack of access. But fundamentally, you kind of bank on a couple things. You know what I mean? Like, you meet some, you have one conversation with many at some point. There's two or three that are interested. There's one or two that are truly serious and moving along, and you're, like, Hey, this is the one that's gonna make it happen for me. Was it like that for you, or did you always have, you know, a dozen or so that you're kind of moving through. You know what I mean, like, how do you get to that because at some point you do need to deliver a POC, and the it's a convoluted question. But the flip side is you don't want to put all your eggs in one basket. The flip side is you can only service so many of them at enterprise white glove level anyway. So at some point you kind of do. How do you kind of manage all that?

Andrew Rubin (00:51:00):
Yeah. So actually, he deserves the callout. Ironically, despite most of them being large companies, our actual first customer is a company down in Los Angeles called CAA. It's been one of the most well-known Hollywood talent agencies for many decades. And they have a chief security officer who, in addition to being a really wonderful human being, is also a very, very aggressive early adopter. He loves to look around the corners. Jeff Blair, and I've known him forever. And he took that first bet. Now, I will say promptly after CIA, which was an easier choice. Not easier sale, but an easier procurement process. It's a big company, but it's certainly not, let's say, a global systemically regulated bank-sized company. You know, after CAA, our next one was Morgan Stanley. And that one was absolutely everything that you would imagine. And after that came a few more big banks. And then we were pretty much, as I said, sort of stuck in that zone. And in this case, being stuck there was wonderful because it forced us to grow up and mature and figure out how to support the largest companies in the world. Obviously, you know, if you can support a Morgan Stanley or a JP Morgan or any global enterprise. In theory, you should be able to take those learnings and then support the upper mid-market or the commercial mid-market or certainly the non-global enterprise market. But there's no doubt about it. We had to do a lot of growing up, and we had to do it very, very quickly. And that's where raising all that money also comes in helpful because you start to hire aggressively against the world and the problem space that you're living in. So if you're going to support a firm like Morgan Stanley or any of their peers around the world. There's this thing called "follow the sun support." The model's been around forever. Illumio didn't have to invent it or even think about it, but here's the thing. Follow the sun support is exactly what it sounds like, which is as the sun moves around the globe. You have to have support people in all these regions so that you always have somebody available live during the daytime to pick up the phone. So you need somebody in the Americas and somebody in Europe and maybe somebody in the Middle East and somebody in Asia. So it's a money thing. It's not. Is the model buildable? Of course it is. Large companies use this to support their customers all over the world for decades. But as a startup. Most don't say, "To support our first three customers, we need a global follow the sun support model right now." We didn't have a choice. And so we made a lot of those investments, I can't say prematurely. Let's just say very, very early.

Pablo Srugo (00:53:29):
And what's that timeline? Morgan Stanley, like from the first time you meet them to the POC to the full contract? Was that two years? You know what I mean? Just give me a sense of what that looks like.

Andrew Rubin (00:53:37):
Yeah, it was very different back then. Obviously, because there really truly was no market awareness of anything, including us. We were brand new. I had met with most of these big banks that became early customers during those two years of stealth. So if I'm being intellectually honest. It was a multi-year sales process because it's not like it started the day we came out of stealth. Not even remotely close. I don't think necessarily today that's accurate. I think today we look more like you'd expect. And if you talk to what I'll call certainly people a growth stage or larger company. I think you'd expect a typical enterprise sales cycle to be, call it, six to nine months. Maybe it's 12 based on procurement. But it's sort of in that six to nine.

Pablo Srugo (00:54:17):
But you have brand, you have referrals. You have all these sorts of things. And when you're starting off. You got none of that.

Andrew Rubin (00:54:20):
You got nothing.

Pablo Srugo (00:54:22):
And so maybe answer this question because I know we're coming on time. Everything so far, and this is the way it happens when you tell stories. Sounds pretty nice and linear, pretty smooth, big round, good team, you know, good enterprise motion. You get some good customers pretty much out of the gate. And yet there is a storyline here that, as I understand it, it still took a long time for these tailwinds to really hit. And there was some, let's say, turbulence. Why was that not? Okay, Morgan Stanley deployed seven-figure contract, private market fit, up and to the right? You know what I mean? What complicates the story?

Andrew Rubin (00:54:56):
So, the way there's a visual here that I think is so easy to comprehend that I don't think it's an Illumio visual. I think every company would tell you, under the covers, this is the picture that they have. When you do a podcast like this, when you tell the story to a friend or a family member, and let's say that line is 10 years long. You're looking at it as a story. So you're out, let's say, 10 feet or 100 feet away. And the line looks just like this because you're far enough away. When you actually get close up and you look at it right here, the line actually is going like this. And by the way, there's a few times the line goes like this and drops down quite a bit. I promise you, it is not revisionist history. It's not rose-colored glasses. And it by no means is an attempt to make it sound easier or more fun than it was. I say that even on the worst days at work that I've had at Illumio, and there have been some really tough ones. It's still the most fun that I'd ever have working in my life. But don't for a second confuse that with there having been some brutally difficult days, weeks, and months. There are quarters that get missed at the last minute. And it's devastating to get up in front of a team of 100 or 200 or 500 people and say, I know you all worked as hard as you could. And unfortunately, the number didn't come in where we thought. And unfortunately, at the end of the day, we're not really rewarded enough, and I don't mean financially. We're not rewarded in terms of our ability to grow up based on how we feel or how hard we try. The number is the arbiter of all truth. That's a hard day when you have to get up and share that news. By the way, when you get up and say, we beat plan, we crushed plan, it is antithetically one of the best feelings that you could ever have to say, I know you all worked hard and look at this win that we're all a part of. And of course, this happens every 90 days. It's not once. It's not once in the life of a company or once a year. And so the ups and the downs. People always say, I go back to WashU where I went to school, and I guest lecture a couple of times a year. And it's inevitable the question comes up. What's the hardest part of the job? Right? It's easy. We're human beings. Try firing somebody. By the way, try firing somebody even when you know it is absolutely the right thing for them, for the business, and for the team. Where there is no doubt that it's the right outcome and it will be better for them too. It's still one of the worst feelings you'll ever have. It is a very human journey that we're on, that we're all on. And so, yeah, the line looks like this when you go raise a lot of money, big customers, revenue seems to be going up, haven't had to raise money in a long time, which is really wonderful. But when you're living it every day, it's got all the highs and all the lows. And actually, another one of my mentors said to me on the really good days, you're going to think you have it all figured out. And on the really, really bad days, you're going to think it's the end of the world. And I promise you, neither one of them are ever going to be right. And I was like, that sums it up perfectly.

Pablo Srugo (00:57:55):
Was there? Maybe we're coming out to the end where I kind of go through the three questions, but I'll ask it in reverse order. Because you mentioned some of the lows. Is there a particular time, day, month, quarter, whatever. Where maybe you really did think things might not work out? Like, things really might, you know, fail?

Andrew Rubin (00:58:15):
No. I can't tell you that I've had a day in sitting in this job where I genuinely came into work and I said, "I think it's actually going to go to zero." I don't think it's going to work. I've let the voice of the customer rule the roost around here since the very beginning. As long as the customer is telling us we're going in the right direction. And of course, you need the data and the POs and the revenue and everything else to align behind it. But since the beginning, we've had unbelievable voice of the customer. We always described it as the customer's been in the room with us since day one. Years before we were even asking them for money. As long as the customer voice was in the room and telling us we were going in the right direction. That was enough data for me to say, "I believe execution is a function of really three things." The ability to raise the money you need to build the business. Using that money to hire the best people and, in particular, leadership that you can, and then giving those leaders and people whatever they need in order to execute and do the job the right way. That's it.

Pablo Srugo (00:59:13):
But were you ever close on the runway side?

Andrew Rubin (00:59:16):
Never. That was one thing that I viewed it as. I'm sure, like many of the other guests that you've had on who are in the CEO seat specifically, I don't say it in a joking way. I actually think that in a lot of ways, I have one of the simplest jobs in the building. I have to do a lot of context switching day in and day out and move between everything from a podcast now to a product roadmap conversation after this. So there's a lot of moving back and forth, but ultimately there's only a few really big things that I own and I'm truly responsible for. Obviously hiring the executive leadership team that report directly to me. But one of them early on was fundraising. And I believe that the CEO ultimately has responsibility for the financial soundness of the business. Later on, as you grow up, the CFO becomes your partner in that endeavour. But in those early days, it wasn't about a CFO keeping the books. There wasn't much to keep. It was all about, do we have enough money in the bank that we can withstand some bad days, maybe a bad quarter? Maybe we get something wrong, and we have to go spend some money to fix it. I over-raised from the very beginning, and over-raised meaning we always had a lot more money in the bank than we ever believed we need for the business plan. That was the insurance policy. And so I never had that moment.

Pablo Srugo (01:00:32):
I think, just for what it's worth. The CEO is uniquely. Three things uniquely the CEO can do. Vision, money, and people. I'm sure those are the three things only you can do.

Andrew Rubin (01:00:40):
Great way to say it.

Pablo Srugo (01:00:41):
Last two questions really quickly. When was the moment for you that you felt like you had true product market fit?

Andrew Rubin (01:00:46):
Like two hours ago.

Pablo Srugo (01:00:48):
Every day? All the time?

Andrew Rubin (01:00:50):
No. Yeah, I mean, honestly, I'm not sure. I'm not trying to be in any way sort of funny when I say this. I don't think that you have true product market fit and then you're done. I think you have moments in time where you figure things out that now make it feel like it's closer than it's ever been. So do I feel like we've got pretty good product market fit for delivering zero trust segmentation to a large enterprise? Yeah, I do. We got there not yesterday, but certainly, you know, it took years, but we got there. We just launched a brand new product at the RSA conference two weeks ago called Insights. It's brand new. I think we'll have product market fit on Insights in what will be a minuscule fraction of the time that it took us to get there on segmentation, even though it's the newest thing we built. We had the customer's voice in the room already because we have all these customers all over the world that have been on the journey with us. And we didn't the first time around. So it's not a moment where the light switch goes off and you're done. It's sort of this constantly evolving thing where sometimes it feels like it's just clicking really well.

Pablo Srugo (01:01:50):
Last question. If you had one piece of advice for like a zero to one early-stage founder, what might that be?

Andrew Rubin (01:01:55):
Two pieces, but they're interrelated. One, talk to every single person who's willing to have a conversation with you, and do it with no agenda whatsoever. Get on airplanes, cars, trains, buses, the tube in London, my favorite way to get around. Go to the customer, go to the prospect, go to the investor. Let them tell you everything. Walk out and disagree with all of it. But listen, because somewhere in there, there's going to be a nugget that you wouldn't have thought of. And somewhere there's going to be a person you meet that's going to end up moving the needle in a way that you could never imagine at the time. And the second one is over-raise early on. Over-raise. Cash is literally the single most important insurance policy that every single startup has years before they're profitable and capable of standing on their own two feet. There's no amount of optimizing for dilution that will ever convince me that raising a lot more, not a little more, money is the right answer.

Pablo Srugo (01:02:49):
Perfect. Well, that's been great, man. Andrew, thanks for sharing your story with us.

Andrew Rubin (01:02:52):
Such a pleasure. Thank you so much for having me.

Pablo Srugo (01:02:56):
Listen, when you go to, like, a restaurant, you eat a nice, you know, meal, maybe a fancy one, maybe not. Do you leave a tip? I assume you probably leave a tip. You probably leave a tip 100% of the time. Well, guess what? A review is just like a tip, and I know you haven't been leaving one. So just like the waiter that doesn't get a tip after hours of great service, I'm getting a little frustrated. So take your phone out and leave a review. It helps the show move up rankings. It helps us get better guests. It doesn't just help me. It helps way more founders. Thank you.