The accidental guardian: How Cloudflare’s Matthew Prince became publishing’s unexpected defender

But when publishers continued to press him, he pulled the data — and that’s when the scale and urgency of the problem snapped into focus for him. He was shocked. He could see that the business model of digital publishing was dissolving. 

“Ten years ago, for every two pages that the Google [search] bot slurped down, copied, they would send you one visitor. Fast forward to today, it’s 18 pages scraped in return for one visitor. What’s changed? [Google] AI Overviews,” he says.

And that’s the good news.

For new players in the digital ecosystem, like OpenAI, that initial trade with publishers never existed. With OpenAI, it’s 1,500 pages crawled for every one visitor sent back to the publisher. If you look at Anthropic, it’s 40,000 to one, he stresses.

But this is just the kind of existential puzzle Prince seems to thrive on. Speaking from his house in Lisbon, Portugal, this fall, he sounds relaxed. Just the day before he was in London meeting with the Competition Markets Authority to argue for why Google must completely separate its AI and search crawlers. 

Although his surroundings are obscured by a generic video-call backdrop, his affection for Portugal comes through clearly. He talks warmly about the locals and how glad he is that he moved the Cloudflare headquarters there from London after Brexit in 2016. It’s become a second home for him and his family, and they’ve spent roughly eight months there spread over the last two years. He uses the Portuguese capital as a base from which he can travel to meet customers across Europe and the Middle East. 

But Prince’s energy spikes the moment the conversation turns to the problem consuming much of his time: what the future of the internet should be. This isn’t an abstract debate for him. It’s a live problem to be solved – one he wants to help shape into something better than the web architecture that came before. 

“A lot of the criticisms of the internet, of social media, come back to this idea that the currency of the internet is traffic. And the problem with traffic is that the best way to get traffic is to appeal to humans’ worst instincts – you know, fear, greed, lust,” he says. 

He points to how some publishers effectively fed this model by producing content as cheaply as possible and relying on increasingly provocative headlines to drive scale. “I don’t think that made humanity better, I think it made it worse…And I worry that if the company [Google] that taught us that traffic was the deity that we all have to worship, also controls the future of the internet, I’m not sure we’re going to fix some of those problems,” he says. 

Let’s make news mistakes, he stresses, not repeat old ones. 

Storytelling as a ‘superpower’

That moment when Prince, 51, saw the dire situation for publishers so starkly visible in the data, nearly two and a half years ago, set off a chain reaction. He hired former Adobe exec Will Allen as vp of product in October 2024. His remit: develop new products to assist publishers and help them defend themselves from the technological onslaught of unregulated AI scraping.

Allen works closely with Cloudflare’s chief strategy officer Stephanie Cohen, and reports to CTO Dane Knecht. He says he was struck by Prince’s personal involvement from the get-go, even before he was officially hired. Not expected from a CEO with 4,838 employees globally. “He just showed incredible patience and thoughtfulness,” says Allen. “He could have pushed me off to somebody else, but he wrote back amazing, thoughtful responses to the questions that I sent over.”

Allen says there wasn’t an exact role defined at that time, more that the vision was clear. “He knew that there was a center of gravity building around this sort of initiative… that we have an opportunity and maybe an obligation here, to build this better internet… so his message has been: we’re going to listen to our customers, listen to the world and try and take a swing at making this better for everyone,” says Allen.

Some of the fruits of those efforts bubbled more publicly to the surface on July 1, when Cloudflare released a pay-per-crawl tool that enabled publishers to block all unauthorized AI crawlers by default with a single button. The company threw a party for publishers to celebrate at its NYC headquarters on the 88th floor of One World Trade Center the night before. Publishing execs described the atmosphere at the time as a tension-releasing moment where emotions stretched from relief to renewed hope and defiance.

Inside the company, colleagues shrug off that moment as largely symbolic — a public marker of work that had been quietly progressing for some time. What had changed was Prince’s skill at crystallizing the public messaging behind it. Several colleagues describe Prince as a master storyteller. His ability to distill big-picture “30,000 ft-high” ideas into practical, relatable guidance is one of the traits they value most about his leadership.

Dane Knecht, Cloudflare CTO, pinpoints the DLD Conference in Munich (Jan. 2025), where Prince spoke on stage with editor-in-chief of German news publisher ZEIT Online, Jochen Wegner, as the moment he “kind of found his voice and found the messaging” around the threat AI posed to content creators and the web.

“He’d been talking about his vision for a good year before that, but it hadn’t quite been coalescing into a message he was able to get out,” says Knecht, who has worked alongside Prince for nearly 14 years, a year or so after its launch in 2009, when you could fit its entire staff into one meeting room. “At DLD he started to nail the messaging and the storytelling. That’s a superpower – the storytelling. Once he figured that out, everything kind of ramped up from there. July 1 was more of a way to really draw a line in the sand.”

That shift in the external storytelling of the company’s vision and role helps explain how Prince’s public profile among publishers exploded seemingly overnight. He went from being a background operator of a web infrastructure company worth $72.84 billion on the stock market, to the CDN vendor CEO all publishers know by name, in the blink of an eye. 

“I’ve seen him get a second wind, almost, from what we call Act 4 at Cloudflare,” says Knecht. 

Shifting the balance of power

Several publishers have told Digiday that AI scraping conditions have since improved, as a direct result. “The relationship between AI companies and publishers is terrible,” says Nicholas Thompson, CEO of The Atlantic. “There’s no leverage to bring the AI industry to the table to try to strike a fair deal. Suddenly, Cloudlfare is like, you know what – let’s give the publishing industry some leverage to make this a fair debate.”

Prince often states that Cloudflare has “no dog in the fight” so it has the ideal neutral stance to act as mediator. “The anecdotal evidence is that the deals the publishers are getting today [with AI companies] are significantly better than they were before, and I’m proud of that,” says Prince. 

Picture this: A big box of blueberries in a store, which all the AI companies just came in and wolfed down. Nobody could stop them, says Thompson. Cloudflare supplied the key to lock the door. Now if they want blueberries, they have to knock and pay for them. “Some of them can still get in the windows, but for the most part, they can’t get the blueberries for free,” adds Thompson. “It’s not like the AI companies have totally changed their tune and are now all in on fair compensation and making up for the original sin. But it changed the dynamics,” he adds. 

Geoff Campbell, svp of strategy and business development at Condé Nast, agrees that Cloudflare’s stance has helped shift control back to publishers and strengthened their leverage in negotiations with AI platforms. “It has also helped build industry-wide momentum around the principle that quality journalism shouldn’t be taken or used without permission,” he adds.

Naturally, there has been concern among publishers that in taking such a defining role, Cloudflare could end up being another dreaded monopoly. History has taught publishers that no tech company will act in their best interests in the long run. Many will in the short run, but they have their own economic incentives and their own shareholders to appease. But for now, in the media industry “he’s the good guy,” as Thompson put it. 

“Some think that he has an ulterior motive, but nothing could be further from the truth,” says Campbell, who began working with Prince after they met in Davos in January 2025. “Publishers are naturally wary of a technology CEO who seems to be looking out for our interests without any direct commercial motivation. At a macro level, Cloudflare does benefit from a healthy and strong internet and information economy. But Matthew is doing this because he believes it’s right, not because he wants to gain some near-term business advantage,” he adds. 

Legendary dinner party host

Prince has earned a side reputation for throwing legendary dinner parties, complete with eclectic guestlists and exceptional private chefs. 

Publisher execs might find themselves seated between a ski instructor and a tech CEO or an elite athlete and a renowned author. Prince hosts these alongside his wife Tatiana. “He’s a fabulous host, his wife’s terrific, and he brings people from all walks of life together. He’s exceptionally generous,” says Thompson, who has known Prince since 2018. At the time, Thompson was editor-in-chief of Wired, which had just published an article featuring Cloudflare. He laughingly recalls how at a dinner party Thompson hosted, Prince passionately argued the case for capitalizing “internet” in the article. “He’s just a kind, smart, interesting, wonderful guy,” adds Thompson. 

Despite being known for pulling off flawless dinners, Prince admits to feeling a flicker of stress before the dinner he is hosting that evening in Lisbon — a small tell that, even at the top, he still cares deeply about getting it right. Colleagues and friends all reference that attention to detail, and how much he cares about people, and society generally, as a consistent character trait they admire, along with a self-effacing, yet direct, manner. 

It’s a mindset that shows up everywhere — even in the purchase of a local newspaper. Prince and his wife bought The Park Record, a local newspaper in his hometown of Park City, Utah, in 2023. It’s a move that seems less sentimental and more like a careful bet on where AI and content economics are heading. “If there’s an AI chatbot in the future for foodies who like to travel, they will have to subscribe to the Park Record, because it’s a destination, and we’re the only ones who write reviews for new restaurants that open,” he says. 

He is adamant that the future can’t be one giant AI brain everyone queries. It needs a whole ecosystem of models, powered by many independent publishers and content suppliers feeding them.

And yet, he’s not interested in perpetuating the internet’s status quo.

“I think that everyone should be asking themselves, if the business model of the internet is going to change, what are the things we want to keep, what are the things that we want to change, and then how do we set the incentives up in such a way to change it?…I can’t imagine anything more fun than having the opportunity to work on figuring out what that change is going to be,” he says.