Matthew Prince, cofounder and chief executive of Cloudflare, used a recent interview to explain why his company moved to block large-scale scraping by AI systems, outline three possible paths for the web’s future, and describe how Cloudflare has dealt with political pressure over the years.
Cloudflare began in 2010 as a firm focused on network performance and protection. Today its services stop distributed denial-of-service attacks, filter malicious traffic, and keep sites online when they receive massive visitor spikes. The company drew wide attention in 2017 when it pulled support for The Daily Stormer, a white supremacist site, an act that signaled a clear change from its earlier posture of strict neutrality. More recently, in July, Cloudflare launched a tool designed to prevent unauthorized AI crawling, creating what Prince describes as a pay-per-crawl approach that forces large language model operators to pay if they want systematic access to publishers’ content.
Prince appeared on a long-form interview program and spent much of the conversation on publishing, the history of the web, and his idea that some AI companies could end up acting like Netflix for written content. The exchange was edited for clarity and length.
A quick round of warmup questions opened the conversation. Asked what shows up in his feeds that he finds embarrassing, Prince answered that political posts on X are often awkward. When asked what he could teach someone in two minutes, he said he knows simple card tricks. He said he reads more nonfiction but prefers fiction for pleasure. On criticism he receives, he noted that online extremists often put him at the center of complaints—either because Cloudflare removes a site or because it continues to provide services to one. The rapid series of short questions set a conversational tone before the interview shifted into biography and strategy.
Prince grew up in Park City, Utah, and says he had his first computer at age seven after his grandmother bought an Apple II. He remembers being fascinated from the start. In college he majored in English and took computer science classes as a minor, eventually serving as a student network administrator and helping build an early campus website. For a time he believed the internet might be a passing fad; his college thesis argued that view. He took the LSAT and enrolled in law school thinking that he would become in-house counsel for a technology company, then gravitated to securities law. In the summer of 1999 he worked on multiple IPOs in San Francisco. The dot-com bubble burst in 2000, and the market’s collapse pushed him toward an insurance-focused software startup that offered stock in place of steady stability. He calls that episode a disaster, then went on to business school, where he met Michelle, his future cofounder.
The company they sketched in business school aimed to move the concept of a firewall into a cloud-delivered service. Their working name at one point was Project Web Wall. Prince said the real insight was that a cloud-based firewall could be given away in a limited form to gather the traffic data needed to build a more valuable security product for large customers such as banks, health systems, and governments. The free tier would collect signals that made the broader product stronger; these signals became a core advantage. “If you take a firewall in the cloud and make it free, you create so many different problems,” he said, “but in the process of solving them you build something bigger than a firewall.”
When asked how he describes Cloudflare in a single sentence, Prince suggested a simple version: “It makes the internet faster and protects it from bad guys.” He then elaborated for audiences who want more depth. The protocols that underpin the internet were designed decades ago, he said, with security often left as an afterthought. Many foundational documents include sections for security that were never filled in. That absence has left opportunity for companies that can rework those fundamental pieces to provide stronger safety, reliability, and performance.
That background feeds directly into Cloudflare’s recent moves around AI. Large language models have drawn heavily from material published on the open web; those models were frequently trained by copying large amounts of publicly available content. Prince sees a problem in that pattern: the creators of original material—journalists, researchers, academics, independent creators—have historically been compensated when users clicked through from search results and saw ads or subscriptions. Google’s search engine for years supplied a steady stream of referral traffic that publishers could monetize. As search results evolve into systems that present synthesized answers at the top of a results page, the amount of referral traffic declines, shrinking publishers’ ability to turn audience attention into revenue.
Prince pointed to a change at Google itself as a clear example. Search results now often show an AI-generated summary or an “AI Overview” that collects pieces of content, compresses them, and presents a synthetic reply. Other services such as Perplexity, OpenAI, and Anthropic serve similar functions. When a user receives a direct synthesized answer, they aren’t clicking through to the original reporting or analysis, so the publisher loses the traffic that once supported advertising and subscription revenues. Prince estimated that the ability to get the same level of traffic for the same content has fallen significantly—his shorthand was that it is roughly ten times harder now than when search results were primarily a list of blue links.
That structural shift prompted Cloudflare to develop defenses that give publishers control over how automated crawlers access their content. The company’s tooling can identify the behavior of bots and the network fingerprints of particular crawling services, letting a site permit, block, or require payment for access from agents that act like Perplexity or ByteDance bots. Prince framed that technical capability as a first step toward a market where publishers can require an exchange of value for their work. “The web has never been free,” he said, pointing out that creators need to earn a living. Search engines, he added, were the dominant mechanism that had provided economic support for content for the past two decades. Cloudflare’s product attempts to replicate an exchange that is appropriate for the AI era.
Publishers’ reactions to Cloudflare’s offering have been strong, he said. He named major outlets among early adopters and said executives at publishing houses told him they felt newly empowered. “I’ve gone from being just depressed, like there’s nothing I can do, to actually being optimistic,” he recounted hearing from some leaders. The analogy he offered compared the situation to what happened in recorded music. Before Apple launched a paid-per-song model, the industry’s economic footprint was smaller; new distribution models expanded revenue that ultimately flowed to artists. Streaming platforms now move large sums—he cited $10 billion paid by Spotify to creators in a recent year—as evidence that new models can deliver sizable returns for people who make content.
Prince sketched three broad scenarios for where content might end up as AI continues to evolve. The most dire is a collapse in the creator ecosystem, with journalists and academics losing the financial incentives to produce original work. A second scenario sees a handful of AI companies internalizing content production—hiring reporters and researchers, operating large centralized newsrooms, and delivering content in ways that reflect each company’s perspective. In Prince’s view that outcome would shrink the diversity of independent outlets and place decision making about information in the hands of a small number of private platforms. The third scenario is a market in which AI platforms pay creators for access to unique material, creating scarcity and a functioning marketplace that rewards originality. Cloudflare’s technology, he argued, is meant to make that third path feasible by giving content owners the ability to control automated access.
Prince used the language of scarcity to make a market point: without scarcity there cannot be a market. In the old web, scarcity existed because content was not easily aggregated into a single answer without driving traffic back to the source. The new generation of answer services collapses that scarcity. Cloudflare’s tools aim to reintroduce scarcity by letting publishers control automated copying. They can block crawlers, differentiate between scraping at scale and casual pageviews, and set policy about who can use their material and on what terms. The company made those tools available for free to any content provider that wanted the option to require an exchange of value before a crawler could harvest their pages.
That approach has led to public deals between publishers and AI companies, and Prince flagged several examples that suggest payment for content is possible. He pointed at Reddit’s disclosure of near-$140 million annually in payments from Google and OpenAI last year and contrasted that sum with a reported deal for The New York Times that amounted to roughly $20 million. The discrepancy, he suggested, stems from the difference between unique, community-generated content and reporting that aggregates widely available facts. Reddit’s contributions are harder for answer services to replicate without direct access, so a licensing arrangement for that material commands a higher price. The music industry comparison reappeared: new platforms assembled ways to pay creators at scale, and something similar could happen for written material.
Prince said Cloudflare’s motive is not purely commercial. He and his wife own their local hometown paper, and he described a personal interest in sustaining journalism. From a company angle, he argued that a healthy internet ecosystem benefits the core Cloudflare business: if publishers and creators vanish, the market that needs Cloudflare’s services would shrink. Yet he acknowledged that the company is already seeing commercial upside as some customers shift infrastructure to Cloudflare to use the anti-scraping tools and related services.
The conversation turned to a different subject when Prince was asked about internet disruptions around the world. Cloudflare’s global network, he said, spans 125 countries. The company publishes regular outage summaries, and in a recent report it found a pattern of government-directed outages changing across the year. The first quarter of the year showed few such shutdowns; the second quarter contained a marked increase. Prince described a seasonal reason for some of the blocking: a number of governments temporarily cut connectivity during national exams to prevent students from accessing online resources and sharing answers. He criticized that approach both for the way it penalizes poorer regions and for normalizing the idea that governments can flip the internet off when it suits them. Those same technical levers, he warned, can be repurposed to silence dissent during political uprisings or to tamp down opposition in the run up to an election.
Prince was asked if Cloudflare had seen any policy shifts with the current U.S. administration and replied that the company has had good relationships across recent presidencies. He named previous administrations and said Cloudflare maintained lines of communication with each. On the current administration, he singled out the State Department for calling certain proposals—such as mandated backdoors into encryption—a trade issue, which he viewed as favorable to an open internet. He said the administration has been assertive in pushing for global access to the internet, an outcome Cloudflare supports.
When the interviewer asked what keeps him awake at night, Prince answered that the breakdown of sustainable funding for original content is his central worry. If creators cannot make a living, he warned, many will stop producing material that underpins public knowledge and civic life. On the optimistic side, he described the technical side of the moment as offering a rare opportunity. The modern AI systems, he said, represent a mathematical map of human knowledge: broad, useful, but incomplete. He compared that map to a block of Swiss cheese—largely solid but with holes that represent gaps in coverage, nuance, and specialized expertise. If platforms and markets properly reward creators for filling those gaps, the quality of the collective knowledge base could improve.
Small signs point in that direction, Prince argued. He pointed to the deals that have already sent money from AI firms to content sites. The Reddit figure he cited—about $140 million annually from Google and OpenAI—stands as an example of a publisher that can command significant payment because of unique contributions. The contrast with the roughly $20 million figure he attached to a large national newspaper made his point about scarcity and uniqueness: aggregated reporting on public facts is less monetizable on an exclusive basis than forum content or original investigations.
The interview included a light moment when Prince described an intimidating meeting with Anna Wintour. He said he arrived in New York in heavy humidity wearing a fall-weight light-blue suit because it was the only one he owned; he spent much of the meeting sweating and felt embarrassed. He praised Wintour’s courtesy and thoughtfulness despite his sartorial misfortune.
At one point the conversation turned to a quick bit of theater in which Prince picked three technology targets under the rubric “Control, Alt, Delete.” For “Delete” he put TikTok in the crosshairs, labeling it as low-value content that adds little to informed public discourse. For “Control” he said he would like influence over the future business model of the web, not to dominate it but to shape incentives so that original work is rewarded. For “Alt,” his wish was to change the state of home automation; he wants a system that works reliably when you walk into a house rather than one where lights and entertainment devices misbehave.
Throughout the exchange Prince returned to a central argument: technical capability alone will not safeguard the internet’s cultural and civic roles unless economic arrangements exist that reward people who produce high-quality material. The company’s anti-scraping tools, he said, are simply a way to give content owners choices. If publishers, platforms, and creators can reach agreements with AI firms that reflect the market value of content, then publishers might find a durable path forward. He framed Cloudflare’s product as an infrastructural contribution to that broader negotiation.
On operational matters, Prince emphasized that Cloudflare’s work focuses on a mix of speed, safety, and privacy. The company has built tools that detect and block malicious traffic, stop supply of automated scraping at scale, and help sites stay online under stress. He framed that set of capabilities as the technical backbone that makes any future model for content viable: if publishers can rely on the network and defend their material, they are in a position to pursue licensing deals and other revenue streams.
The interview threaded technical detail with cultural commentary and a running personal narrative. Prince moved from a childhood encounter with an Apple II to the turbulence of law and finance at the end of the 1990s, then to an entrepreneurial college project that became Cloudflare. He told stories about the company’s decisions and how those choices intersect with public debate about content moderation, digital rights, and national policy. That mix of memoir and technical strategy made the hour-long discussion equal parts origin story, product briefing, and policy argument.
Prince’s posture toward platform responsibility has evolved over time. The decision to cut ties with The Daily Stormer in 2017 was a pivot away from strict neutrality, he said, and it signaled Cloudflare’s willingness to weigh the broader social impact of who uses its network. That stance has continued to influence choices about which services the company will provide and under what circumstances.
He returned repeatedly to the theme that markets require scarcity. In the current environment, synthetic answer services reduce scarcity by absorbing value from many original sources. Cloudflare’s anti-crawl features aim to reestablish control in the hands of rights holders so they can negotiate value. Prince cast that work as a defensive technology that content owners can deploy freely, giving them leverage in talks with AI companies that want to incorporate their material.
Cloudflare has been vocal about the broader governance questions that follow from the rise of AI. Prince argued that the law and public policy communities must think through intellectual property, fair compensation, and the balance between innovation and creators’ rights. He said market solutions are possible, but only if technical controls and negotiation frameworks exist that allow creators to assert ownership and receive payment when large automated systems repurpose their output.
At the end of the discussion Prince summarized an underlying conviction: sustaining robust public information depends on people who are paid to do the hard work of reporting, investigating, and analyzing. The technical tools Cloudflare provides are meant to keep those people economically viable in a market that is being reshaped by systems that can synthesize content without sending traffic back to authors. The device that Cloudflare shipped in July, he suggested, is an attempt to give publishers agency in that transition.
The interview ranged across technology, policy, and personal anecdotes, with Prince offering a long view of where the web could head and a practical explanation of what Cloudflare is doing to affect that direction. He framed the company’s efforts as part of a broader pledge to keep the web fast, available, and organized in ways that allow creators to be compensated for their work.