Matthew Prince may not be a household name, but the world most certainly knows his work.
Prince is the cofounder and CEO of Cloudflare. Launched in 2010, the internet infrastructure company has found itself increasingly in the position of serving as the web’s bodyguard. It filters out bad traffic, keeps sites safe, and stops them from crashing when too many people visit. Its tools defend against DDoS attacks. In 2017, Cloudflare made headlines when it dropped white supremacist site The Daily Stormer. (Maybe Prince’s name is ringing a bell now?)
Cloudflare’s severing of ties with The Daily Stormer marked a momentous shift, one that came after years of claiming a neutral stance. Prince continues to evolve the way Cloudflare works. In July, the company rolled out a new tool tasked with blocking unauthorized AI scraping. It effectively creates a pay-per-crawl model requiring AI platforms to shell out money if they want access to a site’s content.
On this episode of The Big Interview, I talked to Prince about publishing, the old internet, and how his ideal version of the future web means that OpenAI just might become the Netflix of content.
This interview has been edited for length and clarity.
KATIE DRUMMOND: Good to have you here, Matthew.
MATTHEW PRINCE: Thanks for having me.
You should have been warned ahead of time, but you probably weren’t. We always start these conversations with some rapid-fire questions. Think of it like a warmup.
Sort of like wind sprints or something.
Exactly. First, what’s the most embarrassing thing that regularly shows up in your feeds?
Probably just all the political content. On X it’s pretty embarrassing.
What can you teach me to do in two minutes or less? You don’t actually have to teach me anything, but you need to commit that you could do it if you had to.
I am pretty good at simple card tricks, so I could teach you a card trick to impress your friends.
Oh, I like that. I like impressing people. Fiction or nonfiction?
I tend to read more nonfiction, but I’m happier when I’m reading fiction. So I try to force myself to read fiction. The trashier the better.
Alright, trashy fiction. What do your haters say about you?
Oh God, people talk about neo-Nazis surprisingly a lot with me because we either kick or don’t kick them off our platform. So I think [they say] I am responsible for all the bad things that appear somewhere on the internet.
Inbox zero or inbox chaos?
Zero.
Same. OK, let’s jump into it. Are you ready?
I am. Those were fun wind sprints. I enjoy that a lot more than, you know, high school PE.
We do our best. Now, I love to ask people a little bit about where they came from, how they got to where they are. So I’m going to do that before we really get into what’s going on with Cloudflare right now.
The original name of Cloudflare was the only thing worse than Cloudflare, because [those syllables] are really hard for English speakers to say. We were going to be Project Web Wall.
Let’s go back to where it started. Park City, Utah, where you grew up. You got your first computer. My understanding is you were 7. Were you always drawn to technology, even as a toddler, or was that sort of a lucky accident as far as gifts go?
I got it from my grandmother, who was just with it. Apple had just released the Apple II. There wasn’t a ton of access to technology in the way that kids have it today. So everyone else had an Atari. Everyone else had a VHS player. We had a Betamax player. But the computer was really the first time that I dove in and it was like a duck to water. I loved it.
You majored in English, and you minored in computer science. Then you went to law school. What did you think you would end up doing?
I thought I was gonna be the in-house counsel for some cool tech company.
Oh, I like that.
I was good at computers as a kid, and the University of Utah had this incredible computer science program, and they did these continuing education courses and my mom would sign up. And then I’d do all the homework, basically. So by the time I got to college, I thought I was gonna study computer science. I took computer science 101 and I was so bored that an arrogant 17-, 18-year-old me was like, “There’s nothing I can learn from this.”
So I switched my major to English literature. This is like ’92 to ’96. This was right as the internet was taking off. And I knew enough about it that I got hired to be one of the student network administrators on our campus and help build what was one of the first thousand websites. I felt like I was sort of there, but I was also kind of burned out from the whole thing.
I wrote my college thesis on why the internet was a fad.
No.
Yeah. It was pretty embarrassing. I predicted that search engines were gonna become political, that there would be a conservative one and a liberal one. That hasn’t happened.
That’s interesting considering what’s happened with Cloudflare.
When I got to the end, I was pretty good at standardized tests, so I took the LSAT. Didn’t know how to really get a job, so I ended up applying to law school, and I went to law school and in ’96 being like, “Eh, this internet thing is a fad.”
Somewhere in between I took a year off to basically goof around and be a ski instructor. By the time I actually got to the first day of class, I realized two things: One, the internet was gonna be kind of a big deal. And the second thing was that within about three days of law school I was like, “I’m not sure I’m cut out for this.”
Oh.
I finally found a type of law that I thought was really interesting, which was securities law, basically taking companies public. I spent the summer of ’99 working at a law firm in San Francisco. I worked on six IPOs in one summer. It was the dotcom boom. I was like, “This is really fun.”
I bet.
I thought, “I’ll go, I’ll do this for five years. I’ll find a company that’s really great, I’ll help them get ready for their IPO, they’ll hire me as their counsel.” I went back to school thinking that was what was going to happen in March of 2000. Then the bubble burst. The law firm called and said, “Hey, good news, bad news. The good news is you still have a job. Bad news is we don’t need any more securities lawyers, but bankruptcy is basically the same thing …”
Oh no.
I just didn’t want to do that. So I was crying in my beer with a young law-professor guy named Doug Liman, and he’s like, “Hey, my brother’s starting a B2B”—what we call a SaaS company today, although we didn’t at the time, in the insurance industry, which I knew nothing about—“would you be interested? They’ll match your salary and give you this thing called stock.” I was like, “Yeah, that sounds better than being a bankruptcy attorney.” So I did that, and it was a disaster.
That is a journey. There’s been a lot written about Cloudflare’s origins. But just so that people have a basic understanding, how would you describe the company’s original mission, and how has that evolved?
I was super lost. I was working as a bartender. And somewhat to run away from the sort of familial obligation of taking over my father’s restaurant business, I applied to business school, and that’s where I met my cofounder Michelle. What we saw back in 2009 was that all of the world of software was moving to the cloud. So inevitably that would mean that the security and networking tools, the firewalls of the world, would move to the cloud. So the original idea of Cloudflare was: How can you take a firewall and put it in the cloud?
Makes sense.
The problem that we had was we knew that in order to be a successful business, we’d eventually have to sell to really big banks and health care companies and governments and things like that.
Right.
In order to do that, we had to have something that was valuable in order to generate something that’s valuable. We actually had to have data. So being plucky business students, we thought, “Well, what if we made a sort of stripped-down, light version of the service and gave it away for free?”
That would allow us to gather a bunch of data that would be valuable for the firewall, for the big banks and things like that. At some level the whole story of Cloudflare is: If you take a firewall in the cloud and make it free, you create so many different problems. But in the process of solving all of those problems you build what Cloudflare is today, which is more than just a firewall in the cloud.
Tell me how you describe the company today, and then I wanna jump into why you’ve been in the news so much recently.
If I’m at a dinner party and you come up and ask me, “What do you do?” And I say, “I work for Cloudflare.” And they ask, “What does Cloudflare do?” I don’t really want to talk to you much more. I say, “It makes the internet faster and protects it from bad guys,” and everyone’s response to that is, “Oh, that’s really nice.” And then they walk.
They’re like, “Oh, sounds great.”
Yeah, “Thank you for doing that.” If I want to actually engage with someone, what I would say is, “When we wrote all the protocols for the internet in the ’60s, ’70s, and ’80s, we had no idea what the internet was gonna become.”
If you go back and read the original proposal for DNS or BGP or these fundamental kinds of technologies of the internet, like there’s a section often on security, and it says, “This section is intentionally left blank.” Right? So no one has actually done the work to do that. And that’s true in security. It’s true in reliability, it’s true in performance. And so now that we know how important this is, how do we go back and redesign all of those fundamental things about the internet?
That’s what motivates everyone at Cloudflare; that’s what defines our roadmap. When we say we’re trying to help build a better internet, that’s literally what we try to do every single day.
So let’s talk about that better internet in the context of AI. A few months ago your company made major news, especially with people working in media or the creator class, around what you are doing with AI bots and their ability to scrape websites with impunity.
That’s how a lot of these AI models were trained in the first place, right? They scrape the internet, pull whatever content they want, and use it to train LLMs. Your company has now taken a major stand to stop that from happening without financial incentives for the creators of that content. Tell us a little bit about where that idea came from.
So, my cofounder Michelle hates history lessons. I, on the other hand, am a recovering adjunct law professor. So …
Oh boy.
Let’s just talk about the history of the internet, where we’ve been, where we are, where we’re going, and what the opportunities and what the challenges are. So, the first thing is that there’s this sort of mistaken belief that the web has been free. The web has never been free. Somebody has always paid for the web, because journalists like yourself and other folks at Condé Nast, other folks at, you know, all of the different media companies, they deserve to eat.
Agreed.
You know, if you go to a restaurant, they kind of want you to pay your bill. So somehow there has to be money that goes back to the people that are creating stuff, whether it’s news or entertainment or anything else.
For the last 25 years, the great patron of the internet has been Google. They created this incredible tool to let you search for things and then it gives you a treasure map and you can click on the links in that treasure map, and that will take you to content that Condé Nast or Meredith or whoever it is [created]. The key was that the traffic that their treasure maps generated then provided tools to turn that traffic into revenue, into dollars, that you could then pay creators with.
Yes.
Like, that’s an amazing thing. It has, at the same time, had some perverse effects [since] traffic has never been the best measure of quality in any kind of objective sense. You also had a bunch of publications like BuzzFeed that would literally A-B test headlines to figure out which ones generated the largest cortisol response, the largest stress response, because baiting you into clicking things—regardless of what the quality of the actual content was—was kind of the game.
It became all about SEO.
Again, I think Google has been a massive force for good in the world. The internet would not exist in the form that it is right now without Google’s patronage. But that same sort of traffic-is-all-we-care-about [idea] is what led to Facebook, which was what led to TikTok. And we’ve kind of spiraled down this sort of attention-economy hole where I think all of us feel a little bit wistful for the internet of old, right? So that’s kinda where we are today in terms of the content side.
Right.
What’s been happening, though, is that the entire industry has moved away from search being the dominant interface of the web. You can actually see this at Google itself. Now, if you run a search it gives you back an answer at the top of the page. It doesn’t give you a treasure map. Instead it provides you what they call an AI Overview, which has taken a whole bunch of content, smashed it together, summarized it in various ways, and synthesized it.
And Google is just one piece. Like if you look at Perplexity, if you look at OpenAI, if you look at Anthropic, they’re not search engines, they’re answer engines.
The difference is that if you just give someone the answer, then they don’t generate traffic. They don’t follow those links. We have the data on how much of that has changed. The short answer is that in Google’s case it’s about 10 times harder today, because of AI Overviews, to get traffic for the same amount of content than it was back when Google was just 10 blue links.
And I would say [Google] has been very resistant to the notion that AI Overviews have damaged traffic to publishers.
I think they’ve been very careful in saying that they’re still sending a bunch of clicks to the web, but they’ve been very imprecise about what parts of the web are benefiting, what parts are hurting.
So what we see is that if you’re an ecommerce shop, AI Overviews haven’t hurt you as much because, again, people still have to buy the thing. So they’re like, “OK, which digital camera is the best digital camera to buy?” And they get an AI Overview that answers that, but they still then have to go buy the digital camera. So they still go to one of the digital camera sellers that’s out there, but they’re not reading WIRED’s description of what digital camera is the best directly.
Right.
I think they very much know that for things that are just purely information-based, the traffic to those things is just falling off of a cliff. But again, they couldn’t generate that AI Overview if they hadn’t slurped up the data from WIRED, and Ars Technica, and all the different companies out there that are actually doing the work to review the cameras.
I’m still waiting for my check from Google. When is that coming?
Google does send you a check, but they only send you a check—not personally, maybe—if a human has followed a link and then there’s an ad that DoubleClick serves. So Google is still supporting the ecosystem, but that support is declining, declining, declining.
As we shift from search engines to answer engines, the future is going to look different than the past, and I think that there are three possible outcomes. The most nihilistic of all is you starve to death and die.
I personally, and other journalists, don’t want that.
And not just journalists. Academics, researchers, that whole group. It is terrifying to me how many people out there, sort of the AI maximalist camp, are like, “Why do we need journalists anymore? We have drones.” And I’m like, “You really have no earthly idea what good journalism is.”
Sure, the facts, you can do that. But the real color of someone saying, “Hey, your house just was swept away in the flood. How are you dealing with that?” That really is an incredibly important thing.
The reporting, the storytelling, the investigative work. It is human-led work.
So the nihilistic version is awful and I think unlikely to happen. The second possibility, which I think is frighteningly likely to happen, is what I would call the Black Mirror possibility, which is that journalists and academics and researchers don’t go away, but we don’t go back to the media of the 1980s. We go back to the media of the 1400s, where every journalist, every researcher, every academic is employed by one of five big families.
But it’s not families anymore. It’s AI companies. And it’s not too crazy to imagine a world where Sam Altman says, “You know what? We’re just gonna stand up our own Associated Press.” Right? “Lots of unemployed journalists out there. We’re gonna hire them; we’re gonna stand up bureaus all around the world.”
If they do that, then Anthropic has to do it, and everyone else has to do it. Then they’re feeding the machine that’s out there. If that happens, we get back to my college thesis, which [means] there will be a conservative one, and there will be a liberal one, and there’ll be a Chinese one, and there’ll be an Indian one. Europeans will try to create one and eventually just use the liberal US one.
That’s not crazy, but think about how backwards-moving that is. The internet has been this great information equalizer, democratizer. And in this world, all of a sudden, you subscribe to one of the five big AI companies and you get their perspective. It’s going to be very difficult if it’s thousands of dollars a month for your AI subscription. You’re not going to subscribe to two, very few people will. So information in that world gets incredibly siloed, but it’s not crazy.
OK. What’s the third possibility?
Right now everyone’s getting content for free. In the future, I think the AI companies will look less like science labs and look more like Netflix, where what differentiates them is whether or not they have access to unique content, and that unique content is something they will be willing to pay for. That’s the day in which not only Google but OpenAI and Perplexity and Anthropic and all the different AI companies—hopefully there are thousands of them—are sending you a check.
Well, I’m waiting. But Cloudflare is doing something very fundamental in helping ensure that third possibility becomes a reality. Tell us a little bit about how that works.
OK, so that third possibility is a market. The one thing that every market has in common is scarcity. You can’t have a market if there’s no scarcity. Like there’s no market for breathable air because in most places there’s plenty of breathable air.
Yeah, for now.
We’ve talked about a lot of dystopian futures, and we can talk about more if you want, but let’s just try to figure out …
… let’s stick to this one.
So the problem that we saw was that our customers who were publishers, and the entire publishing industry, wasn’t creating scarcity. A lot of that was that they didn’t have the technical wherewithal to actually identify who the AI scrapers were and block them from taking their content.
We’re really good at that. Like that’s what we do every day. We built these tools to stop Chinese hackers or Iranian hackers or Russian hackers. But those same tools also identify “that’s the Perplexity bot” or “that’s the ByteDance bot.” We can give publishers the tools to do that.
If our mission is to help build a better internet, it makes total sense for us to not only build those tools, but then make them available for free to anyone who is creating content online and wants to say, “I don’t want you to have my content unless there’s some exchange of value.”
There’s always been an exchange of value in the search engine world. The exchange of value was that the search engine got your content and in exchange they sent you traffic and then helped you monetize that traffic. As the world moves toward answer engines, we have to figure out what that new exchange of value is, but step one is creating scarcity.
Have companies taken you up on that offer? What’s the response been like?
On the content creator, publisher side it has been extraordinary. Everyone from the Associated Press to Ziff Davis and every publisher in between has come to us and said, “We’ve been waiting for someone to come along.” The most common thing I’ve heard as I’ve talked to the CEOs of publishing houses is, “I’ve gone from being just depressed, like there’s nothing I can do, to actually being optimistic.”
I mean, I cannot overstate what a significant step this is.
The music industry on some level is an analogy. The day before Steve Jobs steps on stage and announces iTunes, 99 cents per song, the entire music industry is worth $8 billion. Not revenue, market cap. That’s a big number, but for the influence that it had in that world, it was actually relatively modest. Ninety-nine cents a song isn’t the business model that ended up winning. It ended up being something closer to Spotify, and there’s still record sales. There’s Spotify and Apple Music and Tidal and YouTube and TikTok. They’re all sending dollars to music creators. Spotify sent $10 billion. So they sent more in cash to music creators and that ecosystem in the last year than the entire industry was worth 18 years ago.
You’ve gotten a lot of really positive press for this. What’s in it for Cloudflare beyond that?
I was my college newspaper editor. My wife and I bought our local hometown newspaper, but not because we’re making any money off of it. Because we believe in local journalism. We need journalists, and we need academics, and we need researchers, and we can’t have new technology just strangle the business model of that.
Personally, that’s my motivation from a company perspective. Like this is an existential threat to us. If the internet stops existing, what’s left for Cloudflare to do? So one of the things that is really important to us is a thriving and vibrant internet ecosystem. Even if it didn’t contribute a single dollar in revenue to us.
But it’s contributing revenue to us already because we’re seeing folks like your parent company and others who are saying, “This is important, and we were using someone else and now we’re shifting to Cloudflare.”
I want to ask you a little bit about a different aspect of what you guys do. So you have this massive network, right? One hundred and twenty-five countries. You released an outage summary on internet blockages or interruptions around the world and found that there were no government-directed outages in the first three months of this year, but the second three months were a different story. Can you talk a little bit about what you’re seeing?
It’s interesting how there’s a seasonality to this and that seasonality happens for what is a pretty silly reason in my estimation. There are a lot of countries in the world that believe access to the internet gives students an unfair advantage if they’re taking standardized tests.
Oh, really?
So at the end of the school year, you’ll see a massive uptick in the internet being turned off in those countries to deny access to students to be able to cheat on the tests. What’s depressing about that? First, they’ve designed tests that you can cheat on so easily just by having access to the internet. Second, we see it being turned off in those countries in poor regions but left on in rich regions. Which is a way that powerful people are helping their own kids but punishing the poorer kids.
But what worries me the most is that it’s normalizing the idea that it’s OK for the government, for what is a relatively silly reason, to turn off the internet and that they have essentially built the tooling to be able to do that on the back of “we must protect the children.”
That same tooling—whenever there’s an election and they want to suppress any kind of other party that might kick them out of power, whenever there’s any sort of civil unrest or protests, they can use that same tooling.
That is fascinating. I have to ask, in the context of the US administration right now, have you seen any changes in the online environment since Trump took office?
No is the answer. We had a great relationship with the Obama administration. We had a great relationship with the first Trump administration. We had a great relationship with the Biden administration. We have, so far, had a great relationship with the second Trump administration.
It’s in the US’s interest for there to be more global internet access. If there is a change, the one place where I think that there has been what we view as a positive change has been that some of the internet blocking or restrictions or what we saw out of the UK where they were trying to force back doors into encryption, some aspects of the Trump administration, the current State Department, have said that’s actually a trade issue. So I actually think that the current Trump administration has been more aggressive at protecting the internet than we saw from the Biden administration.
When you think about everything that your company is across, what is it that’s waking you up at 3 in the morning right now? What do you worry about?
The business model of the internet is breaking, and if content creators don’t have an incentive to create content, if they can’t get famous and they can’t get rich, they’re just going to stop creating content. That’s an existential threat. That’s the nightmare, the dream that wakes me up.
What makes you excited? What are you optimistic about?
So we, for the first time in human history, have a relatively good mathematical model. To describe the totality of human knowledge, it’s not perfect. But if you take all the AI companies that are out there, they have these giant decision trees that they’ve created. It’s the best representation of human knowledge that we’ve ever had, and it tells us what we know, but it also tells us what we don’t know. I analogize it to being like a giant block of Swiss cheese. There’s a lot of cheese, but there’s a bunch of holes in that cheese.
The thing that actually makes me super optimistic is that if we do this right, creating a set of incentives that reward content creators for filling in the holes, that is a lot better business model and a much healthier business model than the old traffic generation.
My evidence that we’re onto something is we’ve seen a handful of content deals, and the company that has gotten the best deal by far is Reddit. We know from their public filings that last year they got close to $140 million a year from Google and OpenAI.
Hmm.
If you compare that with a similar deal that was done for The New York Times, they got about $20 million. So Reddit got seven times more than The New York Times. Why? Well, maybe it’s crazy …
I think I know where you’re going, and I’m gonna agree with you, but [$140 million compared to $20 million is] a wildly different number.
Yeah. But 20 minutes ago we both, I think, agreed that we’re nostalgic for the quirky internet …
Oh, I love Reddit.
… and there’s nothing that represents that more than Reddit. The New York Times is amazing, but if you have data from The New York Times, The Wall Street Journal, The Washington Post, The Boston Globe, like how much real difference is there? Basically the facts stay the same between those, whereas Reddit is this unique content, and so we already have some evidence that the business model of the AI-driven web is going to be one that rewards the Reddits of the world more.
All right. I gotta figure out what hole in the Swiss cheese I’m gonna fill.
You know, the scariest meeting I’ve had in the last little bit was coffee with Anna Wintour. My wife was like, “You have to wear a suit.” And I’m like, “I don’t have anything.”
Wait. This is really important. What did you wear, Matthew?
It was in New York and it was a hundred degrees outside, a hundred percent humidity. The only suit I had was this light blue, fall, relatively heavy suit. So, I wore the suit.
Oh boy.
Anna probably rolled her eyes at this. But I also was just a sweaty mess. So I think it was a pretty embarrassing meeting.
This is a shocking visual. I’m sure she thought it went great. The thing about my boss is that she’s actually really, really nice. So there you go.
She was incredibly, incredibly lovely, and so thoughtful about the whole content and media industry. So I really appreciated the opportunity to get to pick her brain.
That’s really funny.
Even though my sartorial sense is pretty …
Trust me, so is mine. I know the feeling.
Before we end, I wanna play a little game we came up with. It’s called Control, Alt, Delete. What piece of tech would you love to control? What piece would you alt, so alter or change, and what would you delete? What would you vanquish from the Earth if given the opportunity?
So, delete. I’d probably say TikTok. Zero protein, very low-value content, I think, is really dangerous and damaging.
Um, control. I feel super privileged in terms of what we do at Cloudflare, so I would love to have significant influence in thinking through what the next business model of the web looks like. I don’t necessarily wanna control it, but I would love to at least control making sure that we’re rewarding filling the holes in the cheese.
Then, alt. I’m still longing for a home automation system that doesn’t suck. Because I showed up at my house in Austin and the light switches didn’t work and I couldn’t turn the TV on. You know, a smart home that was a little bit smarter.
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