The history of Cloudflare's Birthday Weeks and AI innovation with Matthew Prince

Hello, everyone, and welcome to This Week in Net. This is a special episode all about our Birthday Weeks and Innovation Weeks.

I'm João Tomé, your host, and with me, I have Matthew Prince, our founder and CEO.

Hello, Matthew. Hey, João. Nice to be here.

Nice to have you. It's the first time you're at This Week in Net. Actually, we don't do a lot of in-person shows, so this is an in-person show, too.

Welcome. Thank you.

Thank you for having me. I watch. I'm a big fan. Good. I have a question for you regarding you're in Lisbon right now for a few weeks.

Now, how have you been liking being here, going to the office?

It's been great. So I've actually been here, going to be here for about two months.

So I picked up and moved here.

I'm spending a lot of time visiting with our Lisbon team. We just opened our brand new office, which is absolutely gorgeous.

It's this one. Yeah, exactly. And it's such a fun and lively and just bright place to come and work.

And so I've actually felt incredibly productive here.

So that's been terrific. I'm also spending time going around meeting with customers across all of Europe.

So I am traveling to Amsterdam, up to Stockholm, a number of other trips just to see a bunch of our European customers and spend some time with our team around this part of the world.

The new Lisbon office, as you were saying, it's one of those main offices from Cloudflare.

How that came to be and how relevant it is these days? Yeah, you know, when we started Cloudflare, we realized that we were a global company, no matter what.

And we had to have people who were watching the network, taking care of customers, making sure that we continue to work 24 hours a day, seven days a week, 365 days a year.

And what that meant was we had a choice. We could either put people in one location.

In our case, we started in Palo Alto, California, sort of the Bay Area.

And so we could have people work sort of regular hours, sort of the swing shift and then the graveyard shift.

The challenge is, you know, unless you're a vampire, you don't really like working the middle of the night, most people.

And so the other alternative was we could follow the sun.

And so the first Cloudflare office was in the Bay Area.

The second was actually in London. And the third was in Singapore.

And those continue to be important offices for us. However, when Brexit happened in 2016, we realized that we needed to have a European headquarters that wasn't in the UK.

And so we started to search. We started with 44 different cities.

We narrowed that down to six. Those six were Warsaw, where we already had a small team, Berlin, Amsterdam, Paris, Barcelona and Lisbon.

And Lisbon was the only one of those six that I hadn't personally visited.

And so my wife and I came out here and visited over the holidays, actually, in the Christmas of 2017, and just really fell in love with the people, fell in with just the atmosphere of Lisbon, really, really came to appreciate how welcoming all of Portugal was.

And that was something that was just incredibly important to us as a company, because we want to be good members of the overall community.

And so we made a choice around that and that we would invest in Lisbon.

Today, we're, you know, we have hundreds of employees and continuing to build this up.

And it's one of the most important and fastest growing offices across Cloudflare.

And now we have this beautiful space for our team whenever they're here.

There's a lot of different areas in this office, new office.

It's clearly an office built for building things, for engineers, for sales folks, for everyone, really, has a lot of different areas.

Do you have like a favorite area? Do you enjoy working in specific areas?

I've been, I mean, while I've been here, I've been camping out in our common area, which is where the kitchen and snacks are.

But there are these booths and it's got this incredible view of the bridge in Lisbon that goes over the river.

And so it's just been a great place for me to sort of camp out, be able to meet a bunch of our team, get a bunch of work done.

I actually wrote our annual founder's letter from one of those booths.

And it's, again, just been a happy and comfortable place to be.

Quite interesting. You mentioned the founder's letter that was just published this Sunday.

This is one of Cloudflare's Innovation Week, the most important one, birthday week.

Let's go into birthday weeks.

Birthday week is happening right now. It's the first full day of announcements, September the 23rd.

Cloudflare's birthday is on September the 27th.

How did the birthday week first came about? And with that, Innovation Week too? Yeah.

So Cloudflare launched on September 27th of 2010. We'd actually sort of incubated the company for about nine months prior to that, getting ready for our launch.

But we always think of September 27th as the day of our birthday. And the way that we came to do birthday week, and then what gave rise to then the Innovation Weeks that Cloudflare is really known for, was a bit of an accident in a lot of ways.

We were invited. We had launched at TechCrunch Disrupt, the technology publications conference.

And we were invited back a year later after our launch to give an update.

And they said, you know, it'd be really great if you could announce some sort of product at that particular anniversary.

And, you know, we sat and we were like, what could we launch?

And we really, you know, wanted to do something that was in the spirit of Cloudflare, of giving back to the Internet itself.

And so that very first anniversary of our launch, we actually announced a product that made it easier for people to adopt IPv6, because we really thought that for the future of the Internet, we needed to expand beyond IPv4, the older protocol to IPv6.

And we needed, we could provide a way of making that transition. And what would have been kind of a sort of a ho-hum launch, if we'd done it on any random, you know, Wednesday, all of a sudden got all this attention because of the fact that we had sort of packaged it up around that period of time.

And so that then started a tradition where we thought, okay, every single anniversary, let's do something which gives back to the Internet, gives back to the web, makes it better.

And I think the one that was the real crystallizing was in 2014, which I guess would have been our third birthday.

And in 2014, we made the decision that we would take something, which was really the biggest differentiation between our free and our paid products, which was encryption, and we would make that free for the entire web.

So it was a huge amount of work, took a ton of the team. We weren't sure if it was technically possible.

At the time, this was way before Let's Encrypt or anyone existed.

So we had to actually go out and do deals with the certificate authorities to pull this off.

And I remember so clearly, you know, pushing the button to turn it on on September 27th.

And in that instant, the amount of the web that was encrypted doubled overnight.

Now, since then, we have Let's Encrypt, we have, you know, encryption is sort of table stakes for everyone.

But at the time, and this wasn't that long ago, I mean, this is 10 years ago.

This was really just this real watershed moment for the web. And I think that the whole team felt how powerful that was.

And then all of a sudden, come 2015, everybody wanted something during birthday week, or birthday day on the day.

And so that then expanded to birthday week.

And then over time, we've realized that we don't have to wait around till September 27th, we could actually have targeted innovation weeks throughout the rest of the year, but really started with the IPv6 gateway started with our original launch, really expanded when we when we when we when we made encryption free.

And today, it's just a huge part of the engineering and product culture at Cloudflare.

I'm curious, Synth2Gate, IPv4 gateway, for example, it was already free at a time when it was launched.

The same for SSL. So an encryption security, the free element of making again, it's helping build a better Internet in the sense that we're making it free, it will be already there, even if you didn't select if you didn't enable it.

In what way that also created like a culture of Cloudflare?

You know, I think that, so first of all, our mission is to help build a better Internet.

And we take that very seriously. It's amazing. As I talked to team members from anywhere in the world, how many say the reason I could work anywhere, the reason I work here is because I believe in that mission.

And part of that mission is when we see problems, how do we fix them?

And sometimes, you know, those are problems that really only matter to the biggest companies that are out there.

You know, whether or not you're FedRAMP certified, like that matters to the federal government in the United States, and maybe to some very big companies that service the federal government.

The average blog, they don't care, right?

And so that doesn't, it doesn't make sense. But we do build products that people pay us for.

But from our earliest days, we said, nobody should be faster than someone else because they have a bigger budget.

Nobody should be more reliable than someone else because they have a bigger budget.

Nobody should be more secure than someone else because they have a bigger budget.

And so we were always trying to say, the web should be for everyone, the Internet should be for everyone.

And so how can we make it as accessible and available as possible? And I think that, you know, I think that, you know, that is almost naive in its simplicity of, we're just trying to really serve the Internet.

And Birthday Week is a great way of us demonstrating that.

And so, you know, throughout the course of this week, we're announcing a set of different, you know, features, almost all of which are free, almost all of which are available to every single customer, and almost all of which are really designed to live up to how can we make the Internet faster, more reliable, more secure, more efficient, and more private.

And I think that that's, again, a big piece of why people come to work at Cloudflare and why we have the team that we do.

One of the things that surprised me working here is also seeing that Birthday Weeks, really important.

Other Innovation Weeks, really important.

It drives the teams to build something with a deadline. When there's a deadline, there's an objective, clear objective.

How that element of driving folks to have deadlines, having specific Innovation Weeks about topics like security, developers, things like that, is important in terms of the company building tools, improvements, things like that.

Yeah, I don't think that, I mean, certainly, you know, as we sort of stumbled our way into this formula, I don't think that we realized or appreciated how important that was.

But if I sort of step back and look at it, a lot of companies for a long time have had sort of an annual user conference.

And they've used that as, you know, you've got to get this feature done in order to be included in the Worldwide Developer Conference at Apple or in, you know, in Dreamforce at Salesforce or in Oracle, you know, World, you know, at Oracle or whatever that big event was that people did.

And early on, you know, when we were a much smaller company, we didn't have the resources to go out and put on a giant event.

We couldn't rent out a giant conference center and fly people in from all around the world.

And so we thought, what, and again, it wasn't the original plan, but it turned out that if we just said, let's deconstruct kind of a user conference down to one of its most critical elements, which is, we'll make a bunch of product announcements around, you know, a particular theme.

It's been amazing how much that really drives teams to both think about how they can get products that might be, you know, 90% of the way done over the line, but also as we lay that schedule out for all the innovation weeks at the beginning of the year, it helps really crystallize people thinking, well, what can my team have to launch during that particular time?

And while the innovation weeks have different themes, I think a little bit of the secret of them is that we can kind of slide things in to kind of any of those weeks.

And in a typical year, we'll have between six and eight innovation weeks over the course of the year.

And so there's a, there's a kind of constant rhythm with these deadlines. And I think that really helps us, you know, continue to ship products.

And it's part of why Clouflet are seen as one of the most innovative companies in the world.

Regarding this year in particular, founder's letter was just published. This day actually, where we're recording is the AI day in a way.

How would you categorize in terms of the announcements that we have in general, things that are important for this week specifically?

Yeah, I mean, AI is going to flow throughout the course of the week.

I think what was important and what we really learned talking to our customers is our customers are content creators.

They are publishing information, publishing applications, making kind of their work available online.

And what, if you think about the previous sort of era of the web was I think really defined as the search era, right?

Where and some of the original inspiration for Cloudflare was Google's crawler would create so much traffic.

How could you sustain that if you, if you, if you were just getting crawled all the time and yet, you know, Google's quid pro quo, what they gave you in exchange for, you know, crawling your web was they sent you traffic and you could do things with that traffic.

You could monetize it through advertising.

You could monetize it by, you know, selling products.

You could generate value that had nothing to do with money around just the ego of, you know, I built something people care about and want to see.

And that was the promise of the search era of the web.

As we move to, and it's, you know, it has been kind of a, it's not been as dramatic a transition as people, as people think, but as we move to a web, which is maybe a more AI driven web.

And, you know, this started with Google itself, where you type a question and they give you the answer right on the page without sending you to the page that changes the quid pro quo.

And if you go to something like, you know, chat GPT or anthropic or perplexity, and you ask it a question, you get back an answer.

And the nature of these LLMs is oftentimes they can't even like from a very technical perspective, they can't even credit back where they necessarily found that answer in the same way that, you know, if one morning you wake up and you're really craving Thai food, you might not know exactly why you're craving Thai food, but somewhere in your brain, you know, the, the neurons fired in such a way, LLMs work in a really similar way.

And that's created a real challenge for the web, because if original content creators can't generate value from the content that they're getting, if they don't get that traffic, so they can't sell ads, they can't sell products, they can't just even get recognition that they're the reason that the answer is correct, then why will they create content at all?

And as we have talked with content creators, they've all said, you know, they've had a real fear around this.

At the same time, as we've talked to the best leading AI companies, they've all said, you're absolutely right.

That's a problem we need to solve. And you can see it where they're striking deals with the Reddits and Quoras and, and large companies of the world.

What's been missing though, is how do you give people the visibility, the control, and then the marketplace, if you're a small content creator or a niche content creator to say, I want to figure out how I'm going to give permission for these various AI systems to be able to use my content.

And some people are just going to say, you can do whatever you want with it.

Other people are going to say, you can do what you want with it.

Just send me a t -shirt. Other people are going to say, here's the price list if you want to do something with it.

And what we want to give people is the power to do that.

And so that's on one side of what we're doing with AI.

There's going to be a lot of other announcements over the course of the week where we're doing other things with AI to make it faster, more reliable, more distributed, more regulatory compliant.

Obviously, AI is a big piece of what the future of the Internet, the future of the web is going to look like.

And as Cloudflare has relationships with so many of the top AI companies and so many of the content creators, I think that gives us a really unique opportunity to, again, help maybe rethink what the quid pro quo of the web is going to be in the future.

Makes sense.

And it's quite interesting to see how, and I was a journalist, so it's close to heart, this area of maybe there's an AI provider you want to use your content because you know it will use well.

Maybe you'll gain something with that. Maybe you don't want others to use.

So having that ability to pick and choose what you really want in terms of your content to be available is quite important, having the controls, in a sense.

Yeah. And I think it starts with visibility. So what we're giving now away for free for every Cloudflare customer is a dashboard that lets you see, here's how the AI bots are that are crawling my site.

And I think people will be surprised that there are bots that people might not even know are out there that are constantly scouring the site.

There are also differences in AI bots.

So our team has taken the time to classify different bots differently. The ones that are training LLMs are different than the ones that are effectively like kind of active search agents that are going out.

And we've taken the time to classify them.

And then after we've given you that visibility, now we're giving you the control to say, allow this one through, don't allow this one through, or maybe allow this one through for a price.

And then that will lead to what we're announcing today but won't turn live probably for at least another couple months, which is the marketplace that then says, here's the quid pro quo.

Here's what I as a content creator am willing to let you as an AI company access my data for.

And I think that that's going to be a really powerful tool to again hopefully encourage more original content that's out there.

That's good for the web. That's good ultimately for the AI companies.

And it's good for content creators with unique kind of content that they can feed into these global intelligence systems, which a lot of the AI companies are building.

If there's one idea or conclusion you want folks to have from this birthday week 2024, what would that be?

I think it's that there's still a lot of opportunity to dream big.

Oftentimes I think people think, oh, the web is a certain way, you can't change it.

The Internet's a certain way, you can't change it.

The society is a certain way, you can't change it.

And I think what I'm constantly proud of our team is that they're thinking about and inventing new ways of making the Internet better.

Another example, I talked about the AI example, but another example of a product that's just incredibly revolutionary, we're announcing something called Speedbrain, which is an AI-driven system that intelligently predicts what's the information that you're going to need in order to go to a web page, and then delivers it in anticipation of where you're going, all doing it without putting any additional load on our customers.

It's all delivered from Cloudflare's cache. And the results as we've turned this on are that you're getting almost a 50% increase in performance.

And if you had told me a year ago that we could increase the performance of the web by 50%, I would have said, what are you smoking?

That seems almost just inconceivable.

And yet our team looked and said, we can do this. And what they continue to tell me is, Matthew, we're just getting started.

There's a lot more that we can do to actually really even more dramatically increase the performance of the web.

And again, that's something that we're offering completely free across our entire platform.

And what I think is so amazing is you just think about how much time that's going to save the world as they are not waiting for pages to load.

That's time that you can spend with your kids, that you can go out, walk in the park, you can do other things.

And that's, I think, just, again, Cloudflare's gift back to the entire Internet is, how do we make the web that much faster?

And how do we give everyone who uses it back that time? Makes sense.

One of the things, actually, that working at Cloudflare, when I explain what the company does and the importance of speed, performance, things like that, people think, oh, the Internet is fast.

It's fast enough. It's OK. But to be honest, if you work and your Internet is somewhat your side, your Internet is a little bit slower than usual, you will do less.

You'll be more frustrated when you want to do things quickly.

It's really not a very good experience. And in a big company, that will have effects.

Yeah, but not even just in companies. I mean, I think, again, if you have to sit and wait to figure out what are the hours of the restaurant that you're trying to go to or what's the traffic like outside, that's just time that is wasted.

And so every second that we can take back, every millisecond, every microsecond that we can take back from someone having to wait for information is, again, I think, a gift back to everyone who uses the Internet.

So about 4 billion people that use Cloudflare's network on a monthly basis.

And I'm so excited that we're returning time to all of them.

And that includes chatbots, like waiting for chatbots to give the output.

One question I want to do also is regarding how do we select what comes into a birthday week?

How is that process for you?

What do you know, oh, this is good for us to have here? What goes out?

What is that process? Yeah, so it's not me. This is actually a Samaria question.

Yeah, probably from our team. Well, I think that it's an everyone at Cloudflare question.

I think that there are companies that are designed very much to be run from the top down, where the CEO comes in and says, we're going to go do X.

And then you build a roadmap and drive that forward.

And again, often the assumption behind that is that the CEO is sort of the smartest person in the room.

I'm not the smartest person in the room.

I'm certainly not the smartest person in the room on all of the topics that we have.

And so if everything has to be, what does Matthew want the company to build?

That's going to hold us back as a company. And so we've really designed the company from the beginning to, instead of ideas coming from the top down, they really come from the bottom up.

And I see a lot of times my job is to figure out how can you make the thing that maybe wasn't as ambitious as it could be, how do we make it even more ambitious?

So I find myself often when someone says, oh, here's this thing and we're going to charge this.

It's like, well, why can't we make it free?

Why can't we make it available for everyone? Why can't we do those things?

Because that, again, is part of the ethos of Cloudflare.

And sometimes that can be very scary as an individual at the company to say, well, is that going to have cost to us?

Is that going to challenge it? Is it going to erode our markets in some way?

And again, I think that's a place where I can add value.

But the ideas really come from the bottom up. And so it's multiple different teams across product, a group we call ETI, which is Emerging Technology and Incubation, the engineering team, our research team, all coming together in order to pull this off.

And also just scouring the rest of the company saying, what are ideas of places?

What are problems that we've heard that we can solve and do this?

We sort of start to put this together at the beginning of the year.

So starting in January to think through what it is. But it's often that there's some idea that someone comes up with, even weeks before birthday week, that ends up finding its way, sneaking in if there's a way that we can make it a part of it.

So I wouldn't say it's a really sort of disciplined, rigorous, this is the way we do it every time process.

It's much more, how do we pull the team together, get them aligned around a mission, get them aligned around a vision of how do we give a gift back to the Internet, give a gift back to the web, and then thinking through what are the ways that we can do that.

Once we have sort of the list, then we work with our communications teams and others to figure out what goes on Monday, what goes on Tuesday, what goes on Wednesday, and pull that off.

But again, it's very much a bottoms up exercise. And there will be a bunch or headlines, but I really encourage everyone to read our blog.

If you only read Cloudflare's blog like one time, do it through the course of this week, because there's just so many incredible things that again are all designed to be helping make the Internet a better place, helping make the Internet better.

And on my end, I would say also understanding better how it works, because those are blog posts that try to explain how it did things.

You get a sense of how the Internet works by reading those, and it sounds right too.

Yeah, I think one of the real superpowers that we have or luxuries that we have is that we do get to see a lot of the inner workings of how the Internet actually functions.

The Internet is this mysterious thing that most people take for granted.

We understand, here are the cables, here are the network connection points, here's how a packet of information is encoded and transmitted across the network, here's what even a packet means.

And oftentimes, I think that when we're at our best, we take these opportunities as not only an opportunity to launch a new product or a new feature, but also an opportunity to pull the curtain back and show people like, hey, here's how a little bit more of the Internet works, or here's how your browser pulls down a web page and how that's changed over time, and how we can again use literally machine learning and artificial intelligence to anticipate what you're going to need and send it to the browser in advance, and that that very much can improve the performance beyond what we ever, ever thought was possible.

I have this question that is a bit out of birthday week, but I think it's actually a bit related, which is a bit about your background.

It's about working and developing different disciplines.

In your case, you were a lawyer, actually. You did computer science, did different things.

The question is a little bit more on how no different disciplines, different areas, not just one, helps to build a startup.

Or even right now, think about a birthday week, innovation week, how does that work in a sense?

Well, I wish it was, for me, had been a grand plan. There were definitely times where my parents were like, what is our wayward son doing?

Immediately before I started Cloudflare, my primary job was bartender.

I had certainly gone to a lot of school.

I'd seen a bunch of things. I think one of the things I regret is I had offers out of college to go be a product manager.

I didn't even know what a product manager was, but they had offered me this job to be this product manager thing at companies that I was like, oh, those companies are never going to amount to anything.

It was Netscape, Yahoo, and Microsoft, which any one of those three would have just been this incredible journey to be on.

I think that what has been, as I look at the people that end up being the most successful at Cloudflare, and the people that I really admire, they're folks like John Graft Cumming, our CTO, who has this incredibly deep technical knowledge, but then is this incredible communicator as well.

To the extent that your expertise can be ands, like I do this and this, that oftentimes is just a really powerful formula for people who can excel in their careers.

John is someone who I just admire his ability to take incredibly complicated technical concepts and break them down in a way that people can really understand.

He's been a great mentor to me as I thought about this and a great mentor to a lot of our team.

I think that those are the people that end up being not only the most successful often, but also the people who have the most interesting lives and get to the most fun to hang out with.

I think that's really great.

It's something that we really, really try and hire for. John lives here in Lisbon, so you have been with him a lot.

I know. We have been walking to and from work many, many days.

It's great to just get a chance to have those casual conversations on your walk home from work.

Exactly. Last but not least, I ask this a lot to Cloudflare employees when I have them on the show.

I'll ask you, what is the thing about Cloudflare that most people don't realize in general, but they should potentially?

I think one of the things that we've done, which I think is different than a lot of other companies, most companies, they take their most interesting projects and they hold them back at headquarters.

We've always thought the opposite was the right strategy.

We push a lot of our most interesting projects out to the edges of Cloudflare.

Here in Lisbon, a lot of the work that we do in AI, all the work that's being done in radar, which is the global analytics platform that Cloudflare provides to see the health of the Internet and the web overall, that's all being done here.

A lot of our top security work is being done in London.

I think that's one of those things where we do it differently than a lot of others, where we really think that actually the easiest place to be innovative and especially to do disruptive innovation is further away from headquarters because you get just a little bit more freedom to experiment and try different things.

I am so excited about this office here in Lisbon. I'm going to be spending a lot more time here because there's just so much incredible work that's going on.

I think that we're just seeing that some of the top engineers from Portugal who may have left the country because they couldn't find a job that was really satisfying, they're coming back.

They want to be here. We're seeing a lot of our American team that comes out saying, I'll stay for six months.

Six years later, they're still here.

I think that part of that is can you do really interesting work in a place that you also love to be?

Again, I think something that's a little bit different about us is we've pushed that most interesting work out to the edge.

You don't have to move to San Francisco to be one of the top engineers at Cloudflare.

You can do that in Lisbon. You can do that in London. You can do that in Austin.

You can do that in Singapore. You can do that anywhere. You can still do it in San Francisco as well.

But I think that's something which is, again, different about what we're doing.

I think it's also part of how we've been able to continue to innovate as fast as we have.

Thank you, Matthew. This was great to have you.

For us, we're going to have an episode that is a recap of birthday week with all of the one week's time, actually.

Thank you, Matthew. Thanks, Rob. That's a wrap.