Cloudflare CEO criticizes Portugal, faces scrutiny over airport incident
Matthew Prince was allegedly involved in a security incident at Cascais Municipal Aerodrome (Tires), prompting an official report to the Portuguese Civil Aviation Authority (ANAC).
Cloudflare CEO Matthew Prince has sparked controversy with a sharp rebuke of Portugal’s business environment.
He warned the U.S. cybersecurity firm may scale back investments due to what he described as “suffocating bureaucracy” and persistent immigration delays.
The criticism comes just hours after Prince was allegedly involved in a security incident at a Portuguese airport, prompting an official investigation.
In a series of posts on X (formerly Twitter), Prince lashed out at the country’s infrastructure and regulatory inefficiencies, labeling Portugal “not a serious country” and claiming it had failed to uphold promises made to the company during its expansion.
“Portugal promises much and delivers very little,” Prince wrote, adding that conditions for doing business in the country have “significantly worsened” since Cloudflare began investing.
The San Francisco-based firm opened a major office in Lisbon in 2024, pledging to hire up to 500 employees as part of a broader expansion strategy in Europe.
While Prince had previously praised Portugal’s quality of life and appeal to tech talent, his recent statements paint a starkly different picture.
Mounting Frustration Over Bureaucracy
Prince specifically pointed to long-standing issues with visa processing and hiring delays, accusing Portuguese authorities of failing to deliver on promises of a streamlined onboarding process for international talent.
“We were promised simplified hiring and immigration procedures. None of it materialized,” he said.
The CEO also took aim at Lisbon’s Humberto Delgado Airport, mocking its accolade as “Best Airport in Europe” in 2020, attributing the recognition to “randomness” due to pandemic-related shutdowns.
“Lisbon only has one runway. Call me when that changes,” he quipped in response to a comparison with Newark Airport in New Jersey.
He went so far as to suggest Lisbon’s airport could suffer a “fatal accident” before Newark does, a comment that raised eyebrows among industry observers for its inflammatory tone.
Tensions Within Portugal's Startup Scene
Prince’s remarks come amid wider unease in Portugal’s startup ecosystem.
Industry leaders, including those at Startup Leiria and other incubators, have voiced similar frustrations over slow bureaucracy and an immigration backlog that reached 347,000 unresolved cases as of early 2024.
Critics argue that despite Portugal’s marketing as a tech-friendly haven, its public administration remains ill-equipped to support rapid growth in the digital sector.
“Portugal is falling behind because its institutions don’t match its ambitions,” said a Lisbon-based VC who requested anonymity. “Prince is just saying out loud what many founders have been whispering.”
Prince further inflamed tensions by comparing Portugal unfavorably to Latin American countries such as Colombia and Chile, calling them “more serious” in terms of delivering results for international investors.
Alleged Airport Incident Under Investigation
Just hours before his social media tirade, Prince was reportedly involved in a heated incident at Cascais Municipal Aerodrome (Tires), west of Lisbon.
According to Jorge Roquette Cardoso, the aerodrome’s director, the CEO attempted to board his private aircraft Sunday night without submitting his luggage to mandatory screening.
“Mr. Prince reacted poorly to standard aviation security checks,” Cardoso told local media. “He allegedly insisted that because the plane was his, screening wasn’t necessary. That is, of course, unacceptable under European aviation law.”
The incident occurred around 10:30 p.m. on Sunday and allegedly escalated to a verbal altercation involving raised voices and visibly agitated passengers. There were 10 individuals on board the aircraft, and several were reportedly unsettled by the confrontation.
Security reports from private contractors and airport staff have been submitted to the Portuguese Civil Aviation Authority (ANAC) through the National Civil Aviation Security and Facilitation Commission (FALSEC).
Border police and customs officers were present and reportedly intervened to de-escalate the situation.
Prince and his pilot, identified as Peter Duncan Stewart, were both said to be frustrated by the procedures. As Cardoso emphasized:
“No one boards an aircraft — private or commercial — without proper screening. These are non-negotiable international safety standards.”
As of publication, Cloudflare has not issued a public comment on the alleged incident.
Prince denies the incident
Speaking to Observador on Thursday, Matthew Prince dismissed the idea that his recent comments on social network X were prompted by the incident at Tires aerodrome last Sunday.
The Cloudflare CEO downplayed, and outright rejected, the report: “I have absolutely no idea what they’re talking about.”
“I love Portugal, I love the people, I'm just frustrated with the Portuguese government,” he said.
When asked which administration he was referring to, given the change in government since Cloudflare established operations in the country, Prince clarified: “This isn’t about a specific government. From what I can tell, the past six years of leadership have failed to deliver on their promises. They’re not serious about turning Portugal into a unicorn factory or a genuine tech hub.”
“I’ve reached out through nearly every channel,” he added. “I’m not naming names, but at every level, the Portuguese government has let me down.”
Government and Industry Response
Gil Azevedo, Executive Director of Unicorn Factory Lisboa, a leading tech hub in Portugal, responded to the controversy by acknowledging legitimate concerns while reaffirming the country’s strengths.
“Portugal remains a highly attractive destination for startups and tech talent,” said Azevedo. “But yes, bottlenecks in visa processing must be urgently addressed.”
Since its founding, Unicorn Factory has attracted over 500 startups, with more than half of them being international.
Lisbon has also welcomed 14 unicorn companies since 2022, contributing to more than 15,000 new jobs in the tech sector.
Azevedo urged the Portuguese government to adopt fast-track visa programs for high-skill workers, similar to models in the U.S., UK, Germany, and Australia, and called for a broader EU-level shift toward innovation-friendly policies.
“If we want to keep Europe competitive globally, we need to match rhetoric with regulatory action,” he said.
About Cloudflare
Founded in 2009, Cloudflare provides cybersecurity and internet infrastructure services to major clients including Allianz, L’Oréal, TAP Air Portugal, and the Portuguese Football Federation.
Despite ongoing profitability challenges, the company recently secured its largest contract to date, a deal worth over $100 million.
While Cloudflare remains operational in Lisbon, the future of its presence in Portugal now appears uncertain.
While the struggles with AIMA are very real, I also note that Cloudflare only opened its office in Lisbon last year, in 2024, and it has been an extraordinarily difficult year of political upheaval making the AIMA road even rockier. What the world does not need, in my view, is another wealthy American businessman loudly criticizing others and demanding their own way prioritized over everyone else. AIMA needs the support (and, yes, the positive work culture) to process the applications of people desperate to secure their status so they can work to feed their families, perhaps even more than Mr. Prince needs to bring in his tech workers. He makes some sound points about the thorny challenges facing business innovation, but angry, insulting and/or threatening tweets are not a good behavior model to follow for your brand and reputation. I hope he considers a better way to build relationships and work together to improve the situation (which is what everyone wants!) rather than creating more chaos and loss by pulling out of Portugal.
Very true. And very sad. This country has so much potential but is beset with endless bureaucratic nonsense, antiquated systems and overbearing socialist meddling in businesses and the lives of its citizens and immigrants