You can probably guess the domain name that’s making Anguilla millions

By Trevor Mogg Published September 4, 2025

Anguilla got lucky. Really lucky. When countries were being assigned nation-specific domain names decades ago during the early days of the internet, Anguilla’s “.ai” attracted very little attention. But fast forward 40 or so years and it’s suddenly turned into a serious cash cow for the tiny Caribbean island. And it doesn’t take a genius to work out why.

Thanks to a massive surge of interest in artificial intelligence (AI) that was kick-started by OpenAI with the launch of the generative-AI ChatGPT chatbot in 2022, a rush of individuals, businesses, and organizations have been paying Anguilla top dollar to register new websites with the .ai domain name, BBC News reported this week. 

The BBC cites the example of U.S. tech entrepreneur Dharmesh Shah, who reportedly forked out a whopping $700,000 for the “you.ai” address that at some point will showcase a new AI-focused product. 

While Anguilla gets most of its income from tourism, the hurricane season can cause serious disruption to the flow of inbound travelers. It’s true that most customers purchasing a .ai domain are spending nowhere near as much as Shah, but the cumulative effect of all of the extra business — there are now 850,000 .ai registrations compared to just 50,000 five years ago — is creating useful revenue for Anguilla, a British Overseas Territory. 

Indeed, the BBC’s report notes that last year alone, Anguilla earned 105.5 million East Caribbean dollars (about $39 million) by selling domain names — that’s equal to almost a quarter of its total revenue for 2024. It’s even edging toward the amount brought in by tourism, which accounts for 37% compared to the domain’s 23%. 

Anguilla is able to make some big sales because it held onto what it believed were ultra-premium names — like you.ai — and later released them at auction or set its own prices.