The Exchanges

Q Final one, and then I do want to discuss the Twitter disagreement. Um, you said about having hard conversations there with her, and discussing pretty challenging topics. How do you do that well? I'm never sure whether it's like, you know, um, minimize the time between, you know, action and discussion, you know, good conversation as one had now. How do you do hard conversations well?

A I mean, I think the, it's, I think it's, you have to start out that You know, you, you have, you each have the thing that you're an expert in, and you're the decision maker for that thing. So, so today at Cloudflare, as we think about things, when we have a question of what product to build, ultimately, I'm the one who, who makes the decision on, on that. But Michelle has a ton of input and, and is, is helpful. But, but at the end of the day, it's my decision. On the other hand, You know, when we think about marketing or sales or go to market or support or HR, I mean, that, that side of the business, um, those are all things where ultimately Michelle is the, the decision maker on, on those, those decisions. And she'll often come to me for, for advice. And again, sometimes we disagree, but, but she's the one that gets to make the, the call on, on those decisions. And I, and it's because she's better at those parts of the business than I am. And I think that recognizing that allows you to, you know, disagree, but then commit in a, in a really good way, and then we don't revisit those things. We've had one fight in 1415 years, and it was, she, she hosted a meeting that she invited me to, and I thought the meeting was stupid, and so I was sitting in the, you know, back playing on my phone and rolling my eyes and, and all kinds of things, and at the end, She, uh, she pulled me aside…

AI assessment note: “recognizing that allows you to, you know, disagree, but then commit in a, in a really good way”

Q Yeah, I know. I'm just, you know, devastatingly good skincare routine, um, which, you know, is secret to success in all things. You've got a penultimate one. You've got a dinner party. You can have one guest. Who do you have, dead or alive? Who do you have and why them? You can ask them anything.

A So a live, um, I really, I really admire, um, Tim Cook. I think he's a very principled person every time I've, I've interacted with him. They, he's just, you know, it's easy to poke at the, at the, at Apple as, as the most successful company, you know, in the world right now. But Tim, just as a human, I think is, is really interesting. And having grown up as a, you know, gay, uh, man in the South, uh, and, and having had the success he has, you know, I, I, way before Apple was, Sort of leaning into privacy. I heard him speak about, um, about how important privacy was for his, his life and his career, and I really admire how principled he is. Dead, probably somebody who's thought really deeply about the sort of principles of rule of law. So maybe, maybe Aristotle, maybe, um, Madison. The interesting thing is that for, for us is that when you get to a certain size, um, you know, we're all in the game of the trust game. How do you, you know, fundamentally it's how, how can I prove that we're trustworthy? That's also the problem. Um, that's the fundamental problem of governments is how do you, how do you continue to be, you know, trustworthy? And I think people who have thought about, um, those challenges and really thought through how you put in place systems that, that create trust. That's, I think those are really interesting people. I'd love to have conversations with them.

AI assessment note: “So a live, um, I really, I really admire, um, Tim Cook.”

Q Do you ever get a hard moment of like, what now? You know, Cloudflare is a 19.6 billion dollar market cap company, I think it was when I checked yesterday. You know, a public company, you have an incredible team, it's like, now what? Do you ever get that?

A We just celebrated our, our 13th, um, anniversary of, of launching, which we, which we think is our birthday, which was on September 27th, and I was in our office in Austin, um, and we had a, had a little birthday party with a cake and things, and, And, um, and I was talking to an engineer and they said, um, Hey, what do you think you're gonna be doing? You know, 13 years from now. And usually when people ask that, they ask it on a, on a more civilized timeframe. And my answer is always like, I'll be a cloudflare because I can't imagine anything else that I would do. And I'm 48. So 13 years from now, I would sort of did the math in my head and I was like, I'll be 61. And I was like, wow, that's really old. And And it was the first time where I thought, huh, there is a right time to step away from the company, uh, that you founded. And I, and I think there are people who have held on, uh, to it too long and, and sometimes, you know, at the detriment of, of their company and, and some of the really smart people that could take the, take the company over. Um, you may have, you may have had some of them on your podcast. Uh, and, um, but on the other hand, You know, it's really, it's hard to look out at successful founders. You know, who really successful founders that have stepped away from the thing they started and are actually living a life that I admire. Um, and for a long time…

AI assessment note: “it was the first time where I thought, huh, there is a right time”

Q Has Cloudflare become you, Matthew? You mentioned, you know, you're bending off the new gates.

A Well, I hope it's, I mean, there's probably a bit of me, but I, I think it's, it's, it's, it's bigger than me. It's, it's certainly at least me and, and, and Michelle and Lee. And, and Michelle is, you know, such a radically different human than I am that I think that that DNA, uh, that, that sort of cross-pollination of DNA from, from the two of our, our skill sets, um, has been really, really important. And, and, you know, the things that I'm, Really bad at, ah, she's, she's amazing at. And the things that, um, that, that, you know, once upon a time she was bad at, turned out to be my strengths. But, but again, I, you know, it's been amazing to watch her also evolve as a, as a leader, leader as well. So, so I, I think for sure it, it becomes, it becomes a founder. And I, I think a lot of times the fact that, you know, she and I have been doing this now for, you know, over 14 years and, um, We have hard conversations, but we, we get along. We don't have fights. We're really, we're low drama. I think that that echoes down through, uh, the rest of the organization. And, you know, the, the probably most important thing that you, that you do in your life is pick who your partner is in, in, in, in, you know, whether it's marriage or whatever, whatever you, whatever you believe in. And I think then the, the private second most important thing, if you're a, if you're a, uh, a founder…

AI assessment note: “there's probably a bit of me, but I, I think it's... bigger than me”

Q I mean, clearly you're not a VC because then you'd take credit for everything. My question to you is, and there's a couple that I have to spin off from that, is often we're told you have to love what you do, and it has to be kind of the central passion of your life in entrepreneurship. Do you agree with that statement?

A I will say that this is the first job I've had where I haven't been imagining what else I could do, and people now are like, why do you, why do you still, you know, work at Cloudflare? And I'm like, because I can't imagine anything Where I'm happier and, and can have more impact and, and make more of a difference in the world. You end up spending a lot of time on these things, uh, if they're, if they're successful. And so, you either, I think, have to, have to really love what you're doing, or, or you've, or you've gotta, you know, fall in love with it, because otherwise, um, otherwise it's gonna be tough. I don't, I, but I don't think that my, if you had asked me, You know, 14 years ago was the thing that I cared about most in the world, helping defend, you know, the Internet. I would have, I would have probably said, I would have said no. Um, but I think, um, having then spent the time doing this, you know, I, I feel fall more and more in love with our mission and what we're doing as a company every, every day.

AI assessment note: “you either, I think, have to, have to really love what you're doing”

Q Final one before we actually get into the need. What was the aha moment for Cloudflare? When was that? I'm starting the company. We're doing this.

A You know, I had started another company that was, um, it was in the anti-spam space, was not, was not particularly successful. Still kind of muddles along, um, but, uh, but, but wasn't particularly successful. And we had a really amazing engineering team, uh, without a whole bunch of amazing things for them to do. So we would come up with these sort of side projects, um, that, that were You know, just various things to keep, keep the team busy and entertained. So we predicted the winners at the Sundance Film Festival in advance using Bayesian statistical analysis. Today we'd call it AI, but, um, it's all just statistics under, under the hood. We built a browser plugin that would like switch your Google cookie with other people. This was before Gmail and those things. And the idea was it's really hard to keep Google from getting signal because the very nature of you type something in, it's what you're searching for. But the best, so that you can't eliminate signal, but if you can throw enough noise at it, that's another way to, uh, prevent tracking and preserve privacy. So, so we had that, which was called lost in the crowd. And then we, we, we actually, for, um, Paul Graham, who's someone a lot of your, uh, listeners will know, um, Paul, before he started Y Combinator, um, would host a, a conference at, at MIT called the MIT Anti-Spam Conference, and he would invite me to come …

AI assessment note: “I said, hey, could we build a system that would track basically how spammers”

Q How did you first make money? I ask this of every founder that I meet on the investing side. I think it's very indicative of one's mindset.

A I mean, the first thing that comes to mind, and I don't know if there's something earlier, was, you know, in about fourth grade or so, um, I, uh, I, I, I had access to a bunch of illegal fireworks. And I would sell them at school, which was, made me really popular with the other kids, but not so popular with their parents. Um, and, and so I think that that, that probably something around that, um, there, there, there are a bunch of, again, sort of strange little entrepreneurial things that we did, did in, in school. Although, um, I, again, it was, uh, none of them were necessarily big money makers, but that was, uh, that was probably, that was probably the first thing that I, I, I charged someone money for.

AI assessment note: “in about fourth grade or so... I had access to a bunch of illegal fireworks”

Q I have to ask, you've mentioned your co-founder quite a few times, Michelle. What's your biggest advice to others on partner and co-founder selection, having the great relationship you do with Michelle?

A This is an incredibly important topic. And, um, You know, we're, we're at a point now where, where other founders come and ask us for advice all the time. And one of the most common pieces of advice that we get asked is how did you and Michelle split up your responsibility? And, and usually it comes from, I picked a co-founder. We're having a hard time figuring out who does what. I don't say this, uh, at the time, but what I think is, wow, they're doomed because if it's not totally clear, Then it can become really, really bad. So let me take you back to my previous startup, which is called Unspam. Started also with two other people. Uh, and those two other people basically I picked as, as co-founders, um, because we'd had lockers next to each other in primary school. We were, uh, three white guys. We were all basically the same height. We all basically looked the same. We'd all grown up within a few blocks of each other. We were, we were great, great, great friends going in. And, um, by the time we came out the other side, um, I just still don't talk to one of the, uh, one of the three of them, or one of the other two, I guess. The other one, I, I went years, um, not speaking to. We fought like dogs. And, and what was interesting was, you know, when two of us stepped away from operating roles in the company, the company went on just fine, uh, without, without the two of us. Bec…

AI assessment note: “fundamentally, the problem was, The three of us were the same person.”

Q Has Cloudflare become you, Matthew? You mentioned, you know, you're bending off the new gates.

A Well, I hope it's, I mean, there's probably a bit of me, but I, I think it's, it's, it's, it's bigger than me. It's, it's certainly at least me and, and, and Michelle and Lee. And, and Michelle is, you know, such a radically different human than I am that I think that that DNA, uh, that, that sort of cross-pollination of DNA from, from the two of our, our skill sets, um, has been really, really important. And, and, you know, the things that I'm, Really bad at, ah, she's, she's amazing at. And the things that, um, that, that, you know, once upon a time she was bad at, turned out to be my strengths. But, but again, I, you know, it's been amazing to watch her also evolve as a, as a leader, leader as well. So, so I, I think for sure it, it becomes, it becomes a founder. And I, I think a lot of times the fact that, you know, she and I have been doing this now for, you know, over 14 years and, um, We have hard conversations, but we, we get along. We don't have fights. We're really, we're low drama. I think that that echoes down through, uh, the rest of the organization. And, you know, the, the probably most important thing that you, that you do in your life is pick who your partner is in, in, in, in, you know, whether it's marriage or whatever, whatever you, whatever you believe in. And I think then the, the private second most important thing, if you're a, if you're a, uh, a founder…

AI assessment note: “there's probably a bit of me, but I, I think it's, it's, it's, it's bigger than me.”

Q I mean, clearly you're not a VC because then you'd take credit for everything. My question to you is, and there's a couple that I have to spin off from that, is often we're told you have to love what you do, and it has to be kind of the central passion of your life in entrepreneurship. Do you agree with that statement?

A I will say that this is the first job I've had where I haven't been imagining what else I could do, and people now are like, why do you, why do you still, you know, work at Cloudflare? And I'm like, because I can't imagine anything Where I'm happier and, and can have more impact and, and make more of a difference in the world. You end up spending a lot of time on these things, uh, if they're, if they're successful. And so, you either, I think, have to, have to really love what you're doing, or, or you've, or you've gotta, you know, fall in love with it, because otherwise, um, otherwise it's gonna be tough. I don't, I, but I don't think that my, if you had asked me, You know, 14 years ago was the thing that I cared about most in the world, helping defend, you know, the Internet. I would have, I would have probably said, I would have said no. Um, but I think, um, having then spent the time doing this, you know, I, I feel fall more and more in love with our mission and what we're doing as a company every, every day.

AI assessment note: “you either, I think, have to, have to really love what you're doing”

Q Why did you think it was a dumb idea?

A I, cause I, I don't know. I just didn't, I didn't, I, I, I was like, that sounds hard. And, and at the time we, we thought it would have to be software where it would be like a Apache plugin and writing Apache plugins and Apache was being updated and, and it, it just didn't, it, it didn't seem, it didn't seem like there was a really clear path on how, how to build it. It also seemed, you know, like it was to do it, um, would be really kind of big and hard, and that, that sounded, that sounded daunting. And I'd taken a sabbatical to go, um, to, uh, to business school, largely because the, the company I started got sued, and it was a whole, I mean, a whole, whole big thing. I met Michelle, who was, uh, so Lee, uh, Michelle and I started Cloudflare, but I met Michelle, and I, and Michelle was just clear, was the person I should start a company with, um, Something we can talk about if, if that's, if that's of interest. And, um, she, uh, I was trying to pitch her on idea after idea, all of which, by the way, in retrospect, were terrible ideas. Um, and at some point I was telling her about Project Tiny Pot and how people wanted us to, um, you know, build the thing to stop it. And it was actually Michelle who was like, that's the idea. We're building that. And so it wasn't really even my aha moment. It was, it was actually Michelle's.

AI assessment note: “it didn't seem like there was a really clear path on how to build it”

Q Do you ever get a hard moment of like, what now? You know, Cloudflare is a 19.6 billion dollar market cap company, I think it was when I checked yesterday. You know, a public company, you have an incredible team, it's like, now what? Do you ever get that?

A We just celebrated our, our 13th, um, anniversary of, of launching, which we, which we think is our birthday, which was on September 27th, and I was in our office in Austin, um, and we had a, had a little birthday party with a cake and things, and, And, um, and I was talking to an engineer and they said, um, Hey, what do you think you're gonna be doing? You know, 13 years from now. And usually when people ask that, they ask it on a, on a more civilized timeframe. And my answer is always like, I'll be a cloudflare because I can't imagine anything else that I would do. And I'm 48. So 13 years from now, I would sort of did the math in my head and I was like, I'll be 61. And I was like, wow, that's really old. And And it was the first time where I thought, huh, there is a right time to step away from the company, uh, that you founded. And I, and I think there are people who have held on, uh, to it too long and, and sometimes, you know, at the detriment of, of their company and, and some of the really smart people that could take the, take the company over. Um, you may have, you may have had some of them on your podcast. Uh, and, um, but on the other hand, You know, it's really, it's hard to look out at successful founders. You know, who really successful founders that have stepped away from the thing they started and are actually living a life that I admire. Um, and for a long time…

AI assessment note: “it was the first time where I thought, huh, there is a right time”

Q Does it unlock something else? Does it open the door for them to be able to do another product?

A Maybe, but it is, it is, um, you know, I was, there's that, Ray Rothrock is one of the, one of the, um, early investors in, in Cloudflare, and he said, you know, usually, You start a company, um, that, that he backs. He's like, usually you start with this big vision and it just gets narrower and narrower and narrower. And it, and it, you end up in this smaller box. I think it's actually very hard. And I, and I spent some time, you know, this morning trying to, trying to think of an example. I think it's really hard to find the, the counter example of you start with, you know, What is a, a more limited vision and what you're going to say is what your vision and where you start, those are different things. I think you've got to be careful though, because it turns out where you start, people start to optimize for that and you can find just local minimums and you can spend a whole bunch of time on that local minimum. I think you really do have to articulate what that bigger vision is. I think it's very rare to find someone who said, I started out just trying to build, you know, the, the platform for, you know, People to sell snowboards, and I, and, you know, and I ended up building, building Shopify, or I started out, you know, building that small thing. I think it's a, that's a very, very, very rare case.

AI assessment note: “I think it's really hard to find the, the counter example”

Q Why did you think it was a dumb idea?

A I, cause I, I don't know. I just didn't, I didn't, I, I, I was like, that sounds hard. And, and at the time we, we thought it would have to be software where it would be like a Apache plugin and writing Apache plugins and Apache was being updated and, and it, it just didn't, it, it didn't seem, it didn't seem like there was a really clear path on how, how to build it. It also seemed, you know, like it was to do it, um, would be really kind of big and hard, and that, that sounded, that sounded daunting. And I'd taken a sabbatical to go, um, to, uh, to business school, largely because the, the company I started got sued, and it was a whole, I mean, a whole, whole big thing. I met Michelle, who was, uh, so Lee, uh, Michelle and I started Cloudflare, but I met Michelle, and I, and Michelle was just clear, was the person I should start a company with, um, Something we can talk about if, if that's, if that's of interest. And, um, she, uh, I was trying to pitch her on idea after idea, all of which, by the way, in retrospect, were terrible ideas. Um, and at some point I was telling her about Project Tiny Pot and how people wanted us to, um, you know, build the thing to stop it. And it was actually Michelle who was like, that's the idea. We're building that. And so it wasn't really even my aha moment. It was, it was actually Michelle's.

AI assessment note: “that sounds hard. And, and at the time we, we thought it would have to be software”

Q Do you think it's the same in terms of marriage? How does finding a romantic partner differ?

A Uh, I, I, so I, I, uh, I'm definitely not a couples, uh, therapist, and it's, and it's interesting. I, you know, I feel very fortunate to have dated some just incredible people, um, over, over the years, and especially during the time of, of starting, starting Cloudflare, and it could have worked out with almost any of them, um, but I, I think what, what What happened was, you know, your company came first, and, and I, and I screwed up a whole bunch of relationships, um, because of that, and then I think finally when I got to a place where I felt like I had some stability and, and comfort, and, and met an amazing woman, that was the, the point in time where, where, you know, I, I, I sort of said, okay, I'm ready, ready to get married.

AI assessment note: “finally when I got to a place where I felt like I had some stability”

Q Final one, and then I do want to discuss the Twitter disagreement. Um, you said about having hard conversations there with her, and discussing pretty challenging topics. How do you do that well? I'm never sure whether it's like, you know, um, minimize the time between, you know, action and discussion, you know, good conversation as one had now. How do you do hard conversations well?

A I mean, I think the, it's, I think it's, you have to start out that You know, you, you have, you each have the thing that you're an expert in, and you're the decision maker for that thing. So, so today at Cloudflare, as we think about things, when we have a question of what product to build, ultimately, I'm the one who, who makes the decision on, on that. But Michelle has a ton of input and, and is, is helpful. But, but at the end of the day, it's my decision. On the other hand, You know, when we think about marketing or sales or go to market or support or HR, I mean, that, that side of the business, um, those are all things where ultimately Michelle is the, the decision maker on, on those, those decisions. And she'll often come to me for, for advice. And again, sometimes we disagree, but, but she's the one that gets to make the, the call on, on those decisions. And I, and it's because she's better at those parts of the business than I am. And I think that recognizing that allows you to, you know, disagree, but then commit in a, in a really good way, and then we don't revisit those things. We've had one fight in 1415 years, and it was, she, she hosted a meeting that she invited me to, and I thought the meeting was stupid, and so I was sitting in the, you know, back playing on my phone and rolling my eyes and, and all kinds of things, and at the end, She, uh, she pulled me aside…

AI assessment note: “recognizing that allows you to, you know, disagree, but then commit”

Q I have to ask, you've mentioned your co-founder quite a few times, Michelle. What's your biggest advice to others on partner and co-founder selection, having the great relationship you do with Michelle?

A This is an incredibly important topic. And, um, You know, we're, we're at a point now where, where other founders come and ask us for advice all the time. And one of the most common pieces of advice that we get asked is how did you and Michelle split up your responsibility? And, and usually it comes from, I picked a co-founder. We're having a hard time figuring out who does what. I don't say this, uh, at the time, but what I think is, wow, they're doomed because if it's not totally clear, Then it can become really, really bad. So let me take you back to my previous startup, which is called Unspam. Started also with two other people. Uh, and those two other people basically I picked as, as co-founders, um, because we'd had lockers next to each other in primary school. We were, uh, three white guys. We were all basically the same height. We all basically looked the same. We'd all grown up within a few blocks of each other. We were, we were great, great, great friends going in. And, um, by the time we came out the other side, um, I just still don't talk to one of the, uh, one of the three of them, or one of the other two, I guess. The other one, I, I went years, um, not speaking to. We fought like dogs. And, and what was interesting was, you know, when two of us stepped away from operating roles in the company, the company went on just fine, uh, without, without the two of us. Bec…

AI assessment note: “the problem was, The three of us were the same person.”

Q Do you think it's the same in terms of marriage? How does finding a romantic partner differ?

A Uh, I, I, so I, I, uh, I'm definitely not a couples, uh, therapist, and it's, and it's interesting. I, you know, I feel very fortunate to have dated some just incredible people, um, over, over the years, and especially during the time of, of starting, starting Cloudflare, and it could have worked out with almost any of them, um, but I, I think what, what What happened was, you know, your company came first, and, and I, and I screwed up a whole bunch of relationships, um, because of that, and then I think finally when I got to a place where I felt like I had some stability and, and comfort, and, and met an amazing woman, that was the, the point in time where, where, you know, I, I, I sort of said, okay, I'm ready, ready to get married.

AI assessment note: “your company came first, and, and I, and I screwed up a whole bunch”

Q Does it unlock something else? Does it open the door for them to be able to do another product?

A Maybe, but it is, it is, um, you know, I was, there's that, Ray Rothrock is one of the, one of the, um, early investors in, in Cloudflare, and he said, you know, usually, You start a company, um, that, that he backs. He's like, usually you start with this big vision and it just gets narrower and narrower and narrower. And it, and it, you end up in this smaller box. I think it's actually very hard. And I, and I spent some time, you know, this morning trying to, trying to think of an example. I think it's really hard to find the, the counter example of you start with, you know, What is a, a more limited vision and what you're going to say is what your vision and where you start, those are different things. I think you've got to be careful though, because it turns out where you start, people start to optimize for that and you can find just local minimums and you can spend a whole bunch of time on that local minimum. I think you really do have to articulate what that bigger vision is. I think it's very rare to find someone who said, I started out just trying to build, you know, the, the platform for, you know, People to sell snowboards, and I, and, you know, and I ended up building, building Shopify, or I started out, you know, building that small thing. I think it's a, that's a very, very, very rare case.

AI assessment note: “I think it's a very, very, very rare case.”

Q At 2:38 a.m. No, I'm joking. I'm not too sure. But, uh, you responded pretty strongly disagree with this. Full stop. Help me. Why do you disagree with this statement?

A Yeah. So, so let's, so first of all, let's, let's, let's see if we agree on a framework and then we can, we can get to this. So, so you're a VC. So instantly that carves you out from what I'm going to, what I'm going to call like the entrepreneurs, like my parents, like, you know, bootstrapped entrepreneurs, and you can build incredible bootstrapped companies and businesses. And when you do that, Um, oftentimes focusing on, on a, on a niche is the right, right way to do it. But I, but, but the context of the tweet, I think from you was in the context of you're an entrepreneur and you're going to raise venture capital. And that's a, that's a different, that's a different piece. Or is that, is that fair?

AI assessment note: “let's see if we agree on a framework and then we can get to this”

Q Uh, 2:38 a.m. Uh, no, I'm joking. I'm not too sure. But, uh, you responded, pretty strongly disagree with this. Full stop. Help me. Why do you disagree with this statement?

A Yeah. So, so let's, so first of all, let's, let's, let's see if we agree on a framework and then we can, we can get to this. So, so you're a VC. So instantly that carves you out from what I'm going to, what I'm going to call like the entrepreneurs, like my parents, like, you know, bootstrapped entrepreneurs, and you can build incredible bootstrapped companies and businesses. And when you do that, Um, oftentimes focusing on, on a, on a niche is the right, right way to do it. But I, but, but the context of the tweet, I think from you was in the context of you're an entrepreneur and you're going to raise venture capital. And that's a, that's a different, that's a different piece. Or is that, is that fair?

AI assessment note: “let's see if we agree on a framework and then we can get to this”

Q Final one for you, Matthew, if you look at where we are today, which is circa twenty billion market cap, give or take Depending on the day. 10 years time. What needs to happen for Cloudflare to be a two hundred billion dollar company?

A I was hanging out with, um, Parker Harris, who's the other co-founder of, of Salesforce. And this was right before the pandemic. It was, uh, January of, of twenty-twenty. And I was reflecting on the first 10 years of Cloudflare, and every single day that, um, that, including weekends and holidays, um, I did the math, and at that particular time, we had generated something like seven million dollars in shareholder value every day since, since we had launched, including, again, weekends and holidays. And I was like, I wonder how that benchmarks against, against other, other firms. And so I, I looked at Salesforce, what they had done over that same 10 year period, which was the second 10 years of, of their, of their life. And I did the math and every single day, including weekends and holidays, um, over that same period of time, they had generated something like forty eight million dollars of shareholder value, which is extraordinary. Like, if you think about it. And I told, I told Parker, uh, that, and he's like, wow, that's so cool. I've never thought about, I never thought about it that way. There is something really incredible about subscription businesses. I think it was Einstein, although it might be miscredited, who said that, you know, the most powerful force in the universe is compounding interest. And SaaS businesses have that natural compounding, um, effect to them. And…

AI assessment note: “SaaS businesses have that natural compounding, um, effect to them.”

Q Final one before we actually get into the need. What was the aha moment for Cloudflare? When was that? I'm starting the company. We're doing this.

A You know, I had started another company that was, um, it was in the anti-spam space, was not, was not particularly successful. Still kind of muddles along, um, but, uh, but, but wasn't particularly successful. And we had a really amazing engineering team, uh, without a whole bunch of amazing things for them to do. So we would come up with these sort of side projects, um, that, that were You know, just various things to keep, keep the team busy and entertained. So we predicted the winners at the Sundance Film Festival in advance using Bayesian statistical analysis. Today we'd call it AI, but, um, it's all just statistics under, under the hood. We built a browser plugin that would like switch your Google cookie with other people. This was before Gmail and those things. And the idea was it's really hard to keep Google from getting signal because the very nature of you type something in, it's what you're searching for. But the best, so that you can't eliminate signal, but if you can throw enough noise at it, that's another way to, uh, prevent tracking and preserve privacy. So, so we had that, which was called lost in the crowd. And then we, we, we actually, for, um, Paul Graham, who's someone a lot of your, uh, listeners will know, um, Paul, before he started Y Combinator, um, would host a, a conference at, at MIT called the MIT Anti-Spam Conference, and he would invite me to come …

AI assessment note: “could we build a system that would track basically how spammers, uh, harvest”

Q At 2:38 a.m. No, I'm joking. I'm not too sure. But, uh, you responded pretty strongly disagree with this. Full stop. Help me. Why do you disagree with this statement?

A Yeah. So, so let's, so first of all, let's, let's, let's see if we agree on a framework and then we can, we can get to this. So, so you're a VC. So instantly that carves you out from what I'm going to, what I'm going to call like the entrepreneurs, like my parents, like, you know, bootstrapped entrepreneurs, and you can build incredible bootstrapped companies and businesses. And when you do that, Um, oftentimes focusing on, on a, on a niche is the right, right way to do it. But I, but, but the context of the tweet, I think from you was in the context of you're an entrepreneur and you're going to raise venture capital. And that's a, that's a different, that's a different piece. Or is that, is that fair?

AI assessment note: “let's see if we agree on a framework and then we can get to this”

Q Does it unlock something else? Does it open the door for them to be able to do another product?

A Maybe, but it is, it is, um, you know, I was, there's that, Ray Rothrock is one of the, one of the, um, early investors in, in Cloudflare, and he said, you know, usually, You start a company, um, that, that he backs. He's like, usually you start with this big vision and it just gets narrower and narrower and narrower. And it, and it, you end up in this smaller box. I think it's actually very hard. And I, and I spent some time, you know, this morning trying to, trying to think of an example. I think it's really hard to find the, the counter example of you start with, you know, What is a, a, a more limited vision and what you're going to say is what your vision and where you start, those are different things. I, I think you've got to be careful though, because it turns out where you start, people start to optimize for that and you can find just local minimums and you can spend a whole bunch of time on that local minimum. I think you really do have to articulate what that bigger vision is. I think it's very rare to find someone who said, I started out just trying to build, you know, the, the platform for, you know, People to sell snowboards, and I, and, you know, and I ended up building, building Shopify, or I started out, you know, building that small thing. I think it's a, that's a very, very, very rare case.

AI assessment note: “I think it's a, that's a very, very, very rare case.”

Q What, what was that transition, Matthew? Because I'm in the company comes first stage. And I haven't made the transition. What was that transition?

A I don't know. I felt, I think I felt, I felt like, huh, okay, I've done it. Like, and, and, and been successful enough and, you know, made, made enough that I, I wouldn't worry about, you know, like it's, it's one thing to like have, and when, when we started Cloudflare, I was debt broke. Like I, if we hadn't raised money in November of 2009, like I wasn't sure how I was going to pay my rent. Um, I'd already borrowed a bunch of money from my mom and I mean, it was, it was just, by the way, it was a 30 something year old. Super embarrassing. And it was 2008, 2009, and like there was, there wasn't a really good other, other option. You know, over the years I've had, I was a bartender. I was, I was like, you know, test prep instructor. I had a bunch of just odd jobs to just basically cover, you know, my living expenses. But, uh, you know, we, we had to, we had to close that first round so that we could, uh, Set up payroll so that, so that I could, I could, I could pay my rent. And I, and I remember it when the, um, VCs were like, yeah, you know, we have to, you know, we've signed everything, but it's going to take a few days for us to wire it. And I was like trying to stall my landlord so I didn't get, didn't get evicted.

AI assessment note: “I felt like, huh, okay, I've done it. Like, and, and, and been successful enough”