Matthew Prince, the Cloudflare boss who says no one should have his power

Matthew Prince

Photo: Web Summit / CC BY 4.0, via Wikimedia Commons

Born	November 13, 1974 Salt Lake City
Occupation	Entrepreneur

Matthew Prince runs a company that stands between a large share of the world’s websites and the people trying to reach them, and he has spent years arguing that this position should not make him a judge. Cloudflare, in his telling, is plumbing. Then the plumbing has to decide something: a neo-Nazi site, an anonymous forum tied to a mass shooting, a harassment board, a crawler from an AI lab that takes pages and sends no readers back. He makes the call, then writes a long, signed post about why nobody should have been in a position to make it.

The habit has followed him well beyond the server room. When Cloudflare cut about a fifth of its staff and handed the work to AI, Prince laid out the logic himself in The Wall Street Journal and later objected only to the headline the editors put on it. In Park City, Utah, the ski town where he grew up, he bought the local newspaper, then the plaza at the foot of the town lift, and now he wants the mountain. The argument is always about who should hold power. The person holding it is usually him.

Prince was raised in Park City, up the canyon from Salt Lake City, where he was born at the University of Utah hospital on November 13, 1974, the son of a former journalist who went on to run restaurants and a stock brokerage, and of a mother who owned gift shops and put him to work in them. His great-great-great-grandfather was Jonathan Browning, father of the firearms designer John Moses Browning. An Apple II Plus arrived when he was seven. His mother used to sneak him into computer science classes at the university.

The education that followed explains the blog posts. At Trinity College in Hartford he majored in English literature, minored in computer science and edited the student paper, The Trinity Tripod, graduating in 1996. A law degree from the University of Chicago came in 2000, and from 2003 he taught cyberlaw in Chicago. He never stopped writing like someone trained in literature and law at once, and his company posts still read like legal briefs with better sentences.

The company began with spam. After the federal CAN-SPAM Act passed, he co-founded Unspam Technologies and, with the engineer Lee Holloway, built Project Honey Pot, an open-source network that tracked the bots harvesting email addresses. In 2008 the Department of Homeland Security got in touch with a question Prince has repeated ever since: did they have any idea how valuable their data was? At Harvard Business School he met Michelle Zatlyn, and in 2009 the three of them founded Cloudflare to turn that traffic data into a shield for websites. Cloudflare listed on the New York Stock Exchange under the ticker NET in September 2019, opening at $15 a share, and by early 2026 its network sat in front of roughly a fifth of all websites.

Scale brought the questions he says he never wanted. In 2013, defending service to a Chechen rebel news site, he wrote that “a website is speech. It is not a bomb.” Four years later he cut off The Daily Stormer after the site celebrated the killing of Heather Heyer in Charlottesville and boasted that Cloudflare was secretly on its side. His internal email, obtained by Gizmodo, was blunt about what he had done: “Literally, I woke up in a bad mood and decided someone shouldn’t be allowed on the Internet. No one should have that power.” 8chan followed in 2019, after the El Paso shooting, and Kiwi Farms in 2022, each time with an essay insisting the exception was not a rule.

Prince has heard the critique from both sides. Free-speech purists call it discretion dressed up as neutrality. Others ask why it took a body count, more than once, before he moved. The plainer problem is that the executive who warns about concentrated power runs one of its clearest examples. On November 18, 2025, a database permissions change inside Cloudflare doubled the size of a single configuration file and knocked large parts of the web offline for hours. Prince wrote the post-mortem himself and called it unacceptable. No essay changes how much of the internet runs through one company. Park City has its own footnote: in 2022, while his plan for a larger compound on King Road sat before the town’s planners, language letting him skip that review appeared in a state Senate bill and Prince hired a lobbyist. The bill died in the Utah House.

His current fights are about who pays and who stays. Since July 2025 Cloudflare has blocked AI crawlers by default for new customers and offered publishers a pay-per-crawl system built on the long-dormant HTTP 402 code, betting that AI companies can be made to pay for what they read. In May 2026 Cloudflare eliminated about 1,100 jobs, roughly 20 percent of the company, despite record revenue. Prince’s op-ed ran as “How I Choose Which Cloudflare Employees to Replace With AI”, sorting staff into builders, sellers and measurers; the cuts fell mostly on the measurers. “I didn’t do it because Cloudflare is struggling,” he wrote. Interviewed in September 2026 on Decoder, he said he had not chosen the title but had written the rest, and described death threats “from just random people who are anti-AI.” In October 2026, as attackers rushed at newly disclosed PHP flaws, he told Reuters that “we’re going to have a couple of years where every single week it’s going to feel like the sky is falling.”

At home the money is easier to see. In March 2023 Prince and his wife, Tatiana, bought The Park Record, made its website free and said they intend to turn it into a nonprofit or public benefit company with Spanish-language coverage. In May 2025 he bought Town Lift Plaza on Main Street, and he has kept offering to buy Park City Mountain from Vail Resorts, which says it is not for sale. In June 2026 he told The Colorado Sun he would put about $500 million into lifts and snowmaking and share profits with employees. “The town should own part of the resort,” he said. The couple live in Park City and have a daughter.

The mountain is now a boardroom matter. In an October 19, 2026 filing with the Securities and Exchange Commission, Vail said Prince had introduced two of the four candidates the activist fund Oasis Management is running for its board, the Olympic champion Picabo Street and the investor Bryce Roberts, and raised “potential conflicts of interest.” Prince answered by email that he had suggested several names and had “no influence over who Oasis put forward.” Vail shareholders will settle the slate at an annual meeting whose date the proxy filings still leave blank. Prince says he only made introductions. Everyone else in the room is looking at him.

Tags: business, ceos, tech executives, Cloudflare, Matthew Prince, Lee Holloway