Matthew Prince is the Co-founder and CEO of Cloudflare, an internet infrastructure company that is making the internet a faster and safer place. On today’s episode, Jon Sakoda speaks with Matthew Prince on how he went from bartender to founder of one of the most successful startups built in the last decade.
Matthew Prince is the Co-founder and CEO of Cloudflare, an internet infrastructure company that is making the internet a faster and safer place. On today’s episode, Jon Sakoda speaks with Matthew Prince on how he went from bartender to founder of one of the most successful startups built in the last decade.
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MATTHEW PRINCE: And then 2008 happened, and I was, on paper, absolutely bankrupt at the time. And I think that was right around the same time that I’d met Michelle, that we were starting to think through what could be Cloudflare. And so, at some level, Cloudflare had to work.
JON SAKODA: Welcome to the Decibel Podcast. I am so excited to welcome my friend, Matthew Prince, founder and CEO of Cloudflare. Cloudflare is one of the largest internet infrastructure companies in the world today. It is one of the most successful startups built in the last decade. Matthew is a longtime friend to me and inspiration to many founders here at Decibel. It’s a privilege to have him on this episode of Founders Helping Founders.
And Matthew, it is wonderful to see you. Thank you again for doing this, and welcome to the podcast.
MATTHEW PRINCE: Jon, thank you so much for having me on. You’re looking good, and it’s always a pleasure to connect.
JON SAKODA: I appreciate you saying that. You also look great, and it is so nice to have you on the show. I think many of our listeners already know and possibly even use Cloudflare. I suspect that our founders know what your product does and how wildly successful your company has been. But I don’t think everyone knows your founding story. You were one of the first startups to build an internet-wide infrastructure with a freemium business. You did business globally seemingly overnight, including in places like China. You took on large cloud players. You went public. And along the way, you survived many moments of crisis that I’m sure would have killed others. It’s really an amazing story.
But before we get there, I don’t think everyone knows where you grew up, and where you came from, and what you did before Cloudflare. So if you don’t mind, could we start there? Tell us about where you grew up and what life was like in your house.
MATTHEW PRINCE: Sure. So I grew up actually in Park City, Utah, which is where I’m sitting now. My dad is in his eighties, and early in 2020, actually before the pandemic really kicked off, my wife and I decided to move back here a little bit to spend some time with him, because he lives on his own. And then I’ve largely been here ever since, because it’s been a great place to actually spend a pandemic.
Both my parents were entrepreneurs. I don’t think they would describe themselves that way. My mom owned a series of gift shops, sort of like Crate & Barrel without the furniture, plus Papyrus, plus Starbucks, but only the whole bean coffee, and a flower store all kind of rolled into one. And then my dad did a number of things over the years. He had a radio program, actually, for a while. He was a stockbroker. He owned a bunch of restaurants. He tried to start a ski resort that failed miserably. And I think that the thing I didn’t learn from my parents was how to get a job. But I think I learned a lot of how you invent what your job is.
And then I have one sibling, a sister who’s four years younger, who today is a fashion designer, so she got all the fashion sense, and I wear the same hoodie every day, so.
JON SAKODA: You know, one story I love that you’ve told me before, you had a lot of jobs. You’ve gone to law school. You’ve gone to business school. I remember once you told me that your parents called you all the time asking you, “Matthew, when are you going to get a real job?” So, tell us the story about how you eventually discovered the tech world and then found your way to Harvard Business School.
MATTHEW PRINCE: It was really pretty fortunate that when I was—it was 1980. I had either just turned six or just turned seven. And my grandmother, for Christmas, gave me an Apple II Plus. And basically from that point on, it was like a duck to water, where I really loved working with computers, thought they were great, and did really things that made you super popular in middle school, like going to computer camp.
JON SAKODA: Learning BASIC.
MATTHEW PRINCE: Yeah, BASIC and Pascal, and then eventually C and Assembly, and—
JON SAKODA: Playing Oregon Trail.
MATTHEW PRINCE: Yeah. Oh, well, I was never as much of the play the game. I was more the kid who wrote the games and made up the games. So, went to college thinking I was gonna study computer science, and then started taking some computer science classes. And like the arrogant kid that I was, I was like, oh, there’s nothing for me to learn here. And I remember early on, our very first assignment in Computer Science 205 or whatever was—or the final exam question was, you had to build a CAD program, and you had to type like, toilet, comma, 20, comma, 18, and it would draw a fix-sized toilet at those dimensions in sort of crude graphics. And I was like, that’s really stupid. And so, I went to the library and checked out all the editions of Inside Macintosh and built a full GUI-driven drag and drop, resizeable, pick whatever style toilet you want.
JON SAKODA: I love this story. I love this story.
MATTHEW PRINCE: And I remember the computer science professors were like, “How in the world did you do this?” And the answer was, I mean, at some level, I was just following examples in a book. I didn’t really understand any of the theory behind computer science or anything else. But at this point, I was like, well, these people can’t teach me anything, which was stupid, and transferred from computer science to English literature, which was the polar opposite. I still minored in computer science. And I was in college right in the sort of early ‘90s, right when the campus was building out its computer network. And I was good enough at this stuff that I got hired on to be one of the student network technicians. And that’s how I learned about networking. That’s how I learned about programming routers and switches.
And so, at the end of school, I turned down offers from companies I didn’t think were going anywhere, like Netscape and—
JON SAKODA: Netscape.
MATTHEW PRINCE: … Yahoo, and Microsoft, which is the one that would have been really interesting. And instead thought, I know what I’ll do. I’ll go to law school. And I wrote my college thesis on why the internet was a fad and wasn’t really gonna go anywhere, which was pretty stupid too. And so, I think that a lot of Cloudflare is penance for that time.
But I ended up in law school not really for any good reason other than I was good at taking standardized tests. And within a semester or so, realized that was a mistake. But that was a pretty costly mistake. And what I really didn’t want to do was spend the rest of my life sitting in front of a computer writing code. And what I didn’t realize is that lawyers spend most of their lives sitting in front of a computer writing code, but without the benefits of a debugger. And within a semester, I sort of realized that I was a terrible law student.
And what sucked then was when I was out of school, between when I finished law school and when I went to business school, there was this sort of 10-year period of time where I really felt like I was wandering in the wilderness. And I tried to work for a law firm, and that didn’t really work. I tried to work for a startup that imploded. Once you’ve worked for a startup, it’s really hard to go back to work at a law firm, for sure, and any big company, in a lot of ways.
And so, I was kind of looking for something to do. I was a bartender for a while. I taught LSAT prep courses, GMAT prep courses. I somehow became an adjunct law professor, which I don’t still to this day understand how I was hired to do that.
JON SAKODA: So I have another really important question, because I think, just to fast-forward to the Cloudflare story, did you feel like because you had some of these fits and starts and left turns and right turns, that somehow that just gave you more self-confidence that whatever was gonna happen next, it was gonna eventually work out? Walk me through the journey of the left turns and the right turns before we landed at Cloudflare.
MATTHEW PRINCE: So, I think actually, in a lot of ways, it was the opposite of that. I made, at some level, one very smart decision that allowed me to pay for law school and business school, and somewhat wander in the wilderness, which was, I remember, right as I was starting law school, and this was in sort of 1997, I’d heard that Steve Jobs was coming back to Apple. And I’d always been an Apple fanboy over the years. And so, I called my dad, who was a stockbroker, among other things, at the time, and I said, “I think I want to buy some Apple stock.” And he was like, “Are you sure?” Because Apple stock was—it was at $6 a share or something at the time. And I said, “Yeah, I think there might be something to this.” And that turned out to be a pretty smart decision that allowed me, again, to pay for law school and survive without having a very steady or professional job, and pay for a lot of business school.
And to some extent, I think that that was actually keeping me from really doing the big thing, because I could still eat, and I could afford to pay for a house over my head. And then 2008 happened. And I had basically paid for my life largely by borrowing against these shares that I had in Apple stock. And Apple stock fell a ton. And it was still up from where I had originally bought it, but it went down enough that all of a sudden, I had this thing called a margin call, which I had no idea what that was at the time, and all of a sudden had to sell everything. And then to add on top of that, had this massive tax bill, where I was, on paper, absolutely bankrupt at the time. And incredibly embarrassing to me, as a 30-something-year-old, well-educated, should be a much more successful person, had to go out and borrow money from my mom.
And I think that was right around the same time that I’d met Michelle, that we were starting to think through what could be Cloudflare. And so, at some level, Cloudflare had to work, because I had to pay my mom back. I really didn’t want to go work for my dad’s restaurants, because that just wasn’t my passion, even though he had built a great business himself. And I actually think it was that time where all of a sudden, choices really got focused. That was what forced me to make the decisions that really made it so that we were taking Cloudflare seriously.
JON SAKODA: I think this is a pretty common story in successfully entrepreneurship. In some ways, lack of options clarifies the mind. Many great startups are founded in dark times because there’s not as many options. And success might be the only option.
MATTHEW PRINCE: I think that’s right. I think the one caveat that I’ll say—I mean, I talk about this as dark times, but my parents had been—I mean, we weren’t crazy successful, but I wasn’t gonna starve. I had a safety net that was out there. We were upper middle class or upper class in a lot of ways. And I think that that’s sort of the formula for, I think, a lot of founders that are out there. My hunch is that that actually is a problem, because I think that there are a lot of people who go work at McKinsey, or go take the job at the law firm because they don’t necessarily have that safety net, who if they had the option would be creating things and companies and technologies that could even be more revolutionary.
And so, I think that we as a society and we as an industry need to figure out how—that it can’t just be kind of upper middle class kids, wayward kids, who find their way into startups. And yet that, I think, describes a lot of the founders that are out there.
JON SAKODA: You are making such an important point here. Everybody has a different story as a founder. But I think what is common across all of us is that no matter where you come from, you are stepping into the great unknown for this first time. And that first step requires you to stare into the abyss. Obviously, if you have a safety net of some sort, it can be more comforting. But even if you do have one, I think it’s still a very scary jump for your first time.
I also want to point out that you happened to pick a particular type of business, which you recognized and have described yourself as being very, very high risk, very high return, right? Highest difficulty of dive, highest risk kind of business. I think you’ve said Cloudflare was either gonna be a one or a zero. So talk to me about that decision, because that is, in some ways, just as scary as anything. No matter where you come from, starting a company like that can be quite scary.
MATTHEW PRINCE: Yeah. I think that in business school, I was searching very much to find really people. I have a set of skills and talents. But I also have a lot of weaknesses. And I think the first company that I started really showed me pretty clearly what those weaknesses were. And the people that I’d started that first company with, I realized very quickly were way too similar to who I was. And so, they also had sort of the same list of strengths and weaknesses. And we had picked to start the company together largely because we’d had lockers next to each other in junior high school, which is about the worst possible way to pick. And your spouse might be worse.
But I think that a lot of people try to pick who they start businesses with, with the people that they get along with and they’re friends with. And what that tends to lead to is the question of—and a lot of times, from entrepreneurs, I’ll get the question of like, “How did you and Michelle and Lee split up responsibility early on?” And if you’re asking yourself that question, chances are, you’ve got the wrong founders. And I hate to say that, but I think it’s really true. There’s such a huge surface area of things that need to get done when you’re starting a company that—for us at Cloudflare, it was so clear who did what that we never thought about it, we never argued about it, and I think as a result, we were many times more productive and civil to each other. Whereas at my first company, since we we were all so similar, the org chart said I was the CEO, and the other two founders had other roles. But had sort of drawn slightly different lots, it could’ve been completely flipped around. And as a result, we were all ultimately fighting over and over and over again about the same question, which was who was in charge.
And if you’re doing that, that’s just an incredible waste of time. And so, I think that at Cloudflare, what I was looking for was how do I find other people that could go on this journey me? And I had lots of—I had no shortage of ideas. And so, I think to a large extent, choosing the area that we did, Michelle gets credit for it, because I had all kinds of ideas on—I’d gone to law school. As far as I could tell, the best job in the world from law school was being tax collector. You wanted to collect taxes from people who had a lot of money. And so, I had all of these different ways of how could you tax Google, basically, because Google had lots of money. And so, how could you tax them in various ways? So, we had—there was an idea about you could pass a law around trademark, and you could restrict the thing that Google could sell search terms against.
And I remember I’d run through all these ideas, and Michelle would say over and over, some version of, “Hm, I think that’s a really interesting idea. That’s probably a great business for someone. But it’s not a great business for me, because I want to be able to look at myself in the mirror and be really proud of what I’m doing. And, in my ideal world, I want to go start Google before it’s Google, or Facebook before it’s Facebook, or Microsoft before it’s Microsoft. I want to build something that someday, I’m gonna be incredibly proud of.” And so, I think those two constraints—one, how can you do something which feels like a net positive to the world—not just how do you make money as quickly as possible? And then two, how do you do something that has the potential to be really iconic over time? I think those were really constraints that Michelle put on things. And I think that that’s what led us to what was a really ambitious problem that we were looking at. And I think that that’s part of what’s allowed us to be successful.
What I will say is, it take almost as much work to build the smart dog collar as it does to build Cloudflare. And the challenge, and the thing I really didn’t appreciate, is that the smartest people in the world are like Michelle. They want to work on big, hairy, thorny problems, and they want to be proud of the work that they’re doing. And so, if you have a choice between the big, scary, thorny problem that you don’t see all four corners of, or the thing where you understand all the different components of it, pick the big, thorny, hairy problem. Because it turns out that the hardest thing that you do in this entire journey is attract other people to come along on it with you and help you build whatever it is that you’re building. And it’s just a lot easier to help attract people when you say that your mission is, “We’re gonna help build a better internet,” than we’re gonna, with all due respect for people building fancy dog collars, “We’re gonna sell some fancy dog collars to a handful of rich people.”
And I think that that’s the thing that I underappreciated, is how much mission and scale and sort of the dream of potentially succeeding matters at every single stage along the way. And secondly, how much hiring is the only skill that every founder really needs to have in order to be successful.
JON SAKODA: So, I think what goes hand-in-hand with picking something that’s incredibly ambitious, high risk, high return, also is some contrarian thinking and doing something that a lot of people are going to disagree with or think is crazy. And I can think of no better example of this than Cloudflare. I think early on in the early days, if you said to me, “Hundreds of thousands, if not millions, of businesses will just hand over their DNS keys to a startup,” it’s a big, hairy, audacious goal. But you’ve done that. And not only have you done that, you’ve proven to people that that is not just a good idea—it’s a great idea. And it’s a better internet when people do that.
But let’s go back to the beginning of how you set this big, hairy, audacious goals, and what it means to be a contrarian thinker, and how to organize a company around doing things differently. I think at one point, you said you felt like you were the ugly kid at the dance, right? Nobody really understood Cloudflare. And yet, you were growing and growing and growing. So, do you remember how you set everybody up to somehow see through all of that?
MATTHEW PRINCE: Well, I think that oftentimes, the people who succeed in seeing different paths are not the people who have been the experts in the industry previously, but they’re the people who are sort of tangentially interested in the industry and know just enough to be dangerous. And you can imagine, if you hike the same trail on a mountain every single day, you’re gonna follow the same path, and you know what works, and it’s gonna be the same thing. If you take a kid who’s never been up the mountain and just sort of turn them loose, they may find a more efficient path.
JON SAKODA: That’s right. They’ll forge their own trail.
MATTHEW PRINCE: Yeah. They’re gonna be more likely to sort of see a path that was there. And so, if you look at the Airbnb founders, they didn’t come from a hospitality background. But they were sort of one degree separated from it. They were kind of interested in that space. If you look at the Collisons and Stripe, I mean, they didn’t come from a payment space. They’d tried to start businesses and seen how hard it was to sign up for a merchant account. And they’re like, “Why does this need to be so complicated?”
I mean, I remember really clearly, Michelle and I went to talk to one of our business school advisors whose name is Tom Eisenmann. And Tom’s wife was on the board of Akamai. And we were describing what we were gonna do, because the original plan for Cloudflare was we were gonna build hardware boxes. And very quickly, it became clear that that was not the right path. And so, then we said, we’ll build this giant proxy network. And then everyone’s objection was, “Oh, you’re gonna slow requests down.” And so, then we studied how you speed requests up, and it turned out that in computer science, one of the ways you do that all the time is either with compression or caching. And so, we were building all these compression and caching things.
And we came in, and we presented it all to Tom. And Tom said, “Oh, you’re building a CDN.” And I remember Michelle and I looked at each other, and we looked back at him. And we didn’t want to look stupid in front of our advisor. And so, we were like, “Yeah, yeah.” And we walked out in the hall, and Michelle was like, “CDN, is that Canadian?” And we were like, “We gotta go look that up.” And I mean, I’d heard of Akamai, and I remember when they went public, and sort of following them and being like, “Wow, that’s really clever.” Of course, we went and talked to everyone in the space, and we were like, “Listen, we’re competing with firewalls. Your firewall doesn’t charge you more if you get more attacks. It doesn’t charge you less if you get fewer attacks. So of course we’re not gonna charge based on traffic. That would be insane.” And all the CDN folks were like, “Oh, these guys are gonna be bankrupt over night.”
And again, I think it was one of those instances of, we knew just enough about the space to be dangerous, but we weren’t experts in it. And so, we were willing to look at the problem from a very different perspective. We were the kid running up the hill who doesn’t know exactly what path you have to follow. And I think as a result, we chartered a very unique and different path. And I think that that’s a large part of what’s been successful for us.
JON SAKODA: You are the source of so much great contrarian wisdom. And sometimes I bottle it up and share it with other founders. I always remembered in the early days of Cloudflare when people would ask you, “How are you going to explain to people the difference between Cloudflare and a CDN?”, you used to say that famous Ronald Reagan quote, “‘If you’re explaining, you’re losing.’ We don’t need to explain to our customers how we’re different than a CDN.” And I remember 10 years ago, just the foresight that you had in just making a service so easy to use that people don’t need an explanation as to why they need Cloudflare.
MATTHEW PRINCE: I didn’t even know that was a Reagan quote. I use that all the time. I have to think about that. I didn’t know it was from Reagan. But I do think it’s—I mean, I think at some level, customers buy solutions to problems, right? They hire companies to solve the problems that they have. And what we see what that there was a significant portion of the market that had a significant problem with cyber attacks, had a significant problem with just incredibly expensive bandwidth, had a problem with—their site would show up on, once up on a time, Slashdot, and now Reddit or Hacker News, and it would get overwhelmed. And we thought, there has to be a way that we can solve that problem. And so, it didn’t really matter what you called us. We were a solution to all of those problems.
And fundamentally, I think what Cloudflare is, is it’s a bit like a time machine, where we are saying, “If you could go back to the ‘60s and ‘70s and ‘80s when those original internet specifications and protocols were being laid out, how would you do it differently?” And every day, we’re asking ourselves, what are all the steps that are required to send an email? What are all the steps that are required when you click on a link on a web page? What are all the steps that are required when you SSH into a server somewhere? And how can we make each and every one of those steps faster, more reliable, more secure, more efficient, and more private? And if we can, that’s an opportunity for us to live up to our mission of helping build a better internet.
JON SAKODA: So, I know that we won’t be able to cover every single successful chapter of the Cloudflare story, and I know so many people have already covered that. And you are a wildly successful public company. You built a giant freemium business. You’ve served so many customers around the world. 20% of the internet passes through you every day. You’ve taken on Amazon. You’ve beaten Amazon. You’ve overcome outages and vulnerabilities, and you face some of the most formidable hackers every day. So, you’ve been through so much.
I wanted to give you an opportunity, though, maybe to look back and maybe call out some of the really big, tough things that you think you got right. And then also, is there anything you would’ve done differently? Obviously, it’s a Cinderella story, and this is one of the most successful companies built in the last decade. But looking back, is there something you look back and you say, “I really wish we had done that differently, sooner, or better?”
MATTHEW PRINCE: Yeah. So, I mean, I remember—one of the things I think I’ll end up being the most proud of that we did that was a super scary decision at the time, back in 2014, the difference between Cloudflare’s free plan and the difference between our paid service was largely that our paid service included encryption and our free service didn’t. And this was at a time when only about 30% of web traffic was encrypted, and encryption was really hard and complicated and bizarrely expensive. And I remember, Lee and I were talking about this over beers. And he said, “It’s clear over time that everything online is gonna be encrypted. And that’s the direction everything is gonna go.” And I remember saying, “Well then, if that’s the way that we’re gonna go, we should be the leaders in that, not the followers in that.”
And it was super scary, because we were about to take the one feature that was basically the difference between our free plan and our paid plan, and make it free. So, from a business perspective, that was super scary. And then from a technical perspective, it was incredibly hard. Nobody knew if you could really pull it off at scale. And when you have encrypted traffic, it burns more CPU resources. And everyone said, “You’re crazy. That’ll never work.”
JON SAKODA: Yeah. You were breaking one of the laws of physics, right? This was one of the biggest moves you made.
MATTHEW PRINCE: And in September of 2014, we announced that every single one of our free customers would all of a sudden be just out of the box, magically encrypted. And we held our breath, because we thought this could be the end of our business in a lot of ways, because our costs could go through the roof.
JON SAKODA: All the assumptions, right? It’s gonna be slower. It’s gonna be more expensive. It’s just not gonna work.
MATTHEW PRINCE: And it turned out that, yeah, our upgrade rates dropped ever so slightly. But we increased the number of sign-ups per day by an order of magnitude. Literally, it went up 10X. And in one day, it was also just incredible, the amount of encryption on the web doubled. And that was one of those times it was one of those sort of like, whoa. Because you could see the graphs. And for a while, there were people who were reporting on these things that would say, “What happened on this day, September 27th of 2014?” And it was, we flipped a switch. And that was a really powerful moment. And it was one of those times where it really hit us, like wow, we can make a positive difference in the world. And Let’s Encrypt came shortly after that. And I think we helped inspire them to get that project across the line. And today, if you use a service and it’s not encrypted, it’s like, what’s wrong with you, right?
In terms of the things we did wrong, in the sort of very personal story bucket, around that same time, Michelle and I had met in business school, so in sort of the 2007 time-frame. Lee and I had actually been working together. When we were starting the company, I remember Lee said—because he knew me and Michelle knew me, but Lee and Michelle didn’t know each other. And Lee said, “Listen, I understand why I need you. And I understand why you need me. But I’m not quite so sure why we need Michelle.” And I said, “Give it a month and just watch, and see what happens.” And a month later, he came back to me and he said, “Okay, I totally understand why we need Michelle, and I understand why Michelle needs me. It is a lot less clear to me now why we need you.” And it was quite insightful of him.
But again, I think the three of us were a good founding team. But right around that same time, September of 2014 time, Lee started to—I mean, there’s no other way to say it. He started to become kind of a jerk. And he had been married and had a kid, and he and his wife got divorced, and he started dating someone who was an employee at the company. And I was like, “What are you doing?” And I remember really, it came to a head. We had an all hands meeting, and there were some sales people who were presenting. And he was sitting in the corner playing a video game on his phone. And I texted him. I said, “Are you playing a video game on your phone?” And he’s like, “Yeah, this is boring.” And I was like, “Lee, you’re one of the senior leaders at the team.” And he was running all of our engineering team. We ended up bringing team a very experienced, seasoned engineering leader. He just clashed with him back and forth and left and right. And it was a real mess. And eventually, this person left, largely because he just couldn’t deal with Lee.
And Lee’s job got narrower and narrower and narrower over time. And he was still this incredible architectural genius, but he just became incredibly difficult to work with. And so, around 2017, and this was for a long time, like this would be all that Michelle and I would talk about. And Michelle, who again, didn’t know Lee as well, was like, “We gotta do something about this.” And so, finally in 2017, I said, “You know, Lee,” and it was super emotional for me. I said, “You know, Lee, you’ve gotta go.” And he was like, “Yeah, you’re probably right.” And then he left. And I went from being sad to actually being really angry. Because it was like, we’re showing up every day. We’re working super hard. And about six months later, his second wife, she showed up at the office and she said, “I’ve gotta tell you, Lee’s been diagnosed with a brain disorder called frontotemporal dementia,” which is just a really cruel disease. Basically, the frontal lobe of your brain, which is what controls your sort of ability to have empathy and relate to other people and interact in groups, basically melts. And so, all this time when Lee was becoming a jerk, what was really happening was his brain was melting.
And I think he’d had the disease since he met. I’m not sure we could’ve pulled off what we did with the encryption bit without his sort of incredible ability to focus and cut out a lot of the other distractions. And to this day, there’s code which people are like, “Whoa, who wrote this? This is really genius.” And almost every time that happens, it was Lee in this sort of window of time from about 2012 to about 2015, where I think that maybe because of the brain disorder, he was able to really focus on things in a way that most human beings can’t. But today, it’s incredibly sad. He’s still alive, but he’s not verbal. He doesn’t seem to recognize me, or Michelle, or his brother anymore. He’s in a place that’s safe. His family has gotten him a place where he’s got kind of room to sort of safely roam.
But I think that was a good illustration that when people do start to behave differently, I try to always remind myself, what might be going on elsewhere in their life? What might be going wrong with them?
JON SAKODA: Yeah. It’s so hard to see the world through their eyes, right? We all think that we understand what’s going on in someone’s lives, but we have no idea of what’s going on. In a beautiful way, you and Michelle frequently bring up his contributions. And increasingly, I think we are all now greatly appreciative of his technical contributions. I mean, in many ways, though he is different, what he has contributed lives on. And I think we can all remember him for that greatness.
MATTHEW PRINCE: Yeah. And there’s a great—if people are interested in his story, there’s a great Wired piece. “What Happened to Lee?” is the title. And we have so far been successful in making sure that the Wired editors don’t put it behind the paywall. So, you can google it and find it.
JON SAKODA: So, I have one last question. It’s my favorite question that I love to ask. And that is, looking back, is there any advice that you would give to your younger self, the person that’s about to start the journey?
MATTHEW PRINCE: Oh gosh. I think probably take the job at Microsoft. I really do think that the thing that I missed out on at some level, and would’ve made the journey a lot easier, is had I taken some time at really a fast-growing, successful technology company, where I could have watched how the leaders there worked; could’ve built my network up a lot better. It would’ve been so much easier to hire people if I could’ve just called up my former colleagues from Microsoft and said, “Hey, wanna come start this journey?” I think it would have been a lot less lonely along that way. And so, there’s sort of a window of time there where—again, I don’t think I would want to have been a career person at any of those companies. But I do think that spending five years at a company that you can really learn from, even if you think ultimately you’re gonna go start something, I think that that is such valuable advice.
And so, I was fortunate to be able to go through a lot of educational experiences. But I never really had that go work at a big company experience. Again, the trap is, don’t stay there for the rest of your life. But I love the fact that we’re building kind of—I don’t really like “mafia” as a term—but sort of a Cloudflare diaspora of people who’ve gone and started really amazing companies—Coalition, the cyber insurance company. Dani and Irtefa at Jam. Maria at the AI Company up in Seattle. There’s a group of people who spent some time at Cloudflare, kind of absorbed the Cloudflare DNA, learned from what we did well and what we did poorly, and now I think are off building other companies. And as I think about what success will look like going forward, it’s really rewarding to get to see, as people do start other things, that they take the best of us and riff and on it and make it better in other places.
JON SAKODA: Maria’s company, I believe, is called is YLAB. It’s a really impressive company. And Josh’s company is an amazing cyber insurance company. So, you do really have a great alumni base that have gone on and done great things, which I think is a testament to the quality of the people that you’ve hired through the years.
It’s rare that I say this, but as we wrap up, I’m really grateful that you can’t go back in time and tell your younger self to take that job at Microsoft, because I suspect that maybe we would not have seen Cloudflare if that was the case. And I know that there are now hundreds of thousands of customers that would not have the privilege of using your service. So, I’m in many ways grateful that you’re stuck here with us in the present. But I do really want to thank you for joining us today, Matthew. You’ve been an incredible friend to so many founders, and you’ve been an incredible friend to me. I really appreciate you coming on the podcast today, and thank you for being here.
MATTHEW PRINCE: Thanks, Jon. Hope to see you out in Park City.