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Anguilla hit the jackpot with its national website domain.
Although US residents are likely used to visiting sites with .com, .org, and .edu, it’s common for other countries to use domains that reflect their names, like .uk in the United Kingdom or .cn in China.
Anguilla, a British territory, also uses a country domain, and until the last few years, its .ai domain wasn’t remarkable.
Industry insiders have been keeping an eye on how AI’s growth could impact Anguilla since 2023, as Business Insider previously reported. Now, as AI transforms the internet and our world, .ai is a moneymaker Anguilla never saw coming, as eager AI founders pay the country to register .ai domains.
For instance, tech founder Dharmesh Shah paid Anguilla $700,000 to secure the domain you.ai, as the BBC first reported.
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“I usually don’t invest in .ai domains — I lean towards .com,” Shah, the cofounder and CTO of HubSpot, told Business Insider. “But, you.ai was a great name and I had an idea for a project for it.”
The BBC reported that Shah said he hoped you.ai could serve as the domain for a product that would “allow people to create digital versions of themselves that could do specific tasks on their behalf.”
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Shah told Business Insider he doesn’t usually set out to buy domains to sell them, though in 2024, he posted on X that he bought chat.com for over $15 million and later sold it to ChatGPT for an undisclosed price. He owns a few other .ai-related domains as well, including simple.ai, easy.ai, and chess.ai.
According to Domain Name Stat, the number of .ai domains jumped from just 40,000 at the beginning of 2020 to 859,000 as of August 2025. Additionally, in a 2024 report, the International Monetary Fund said that Anguilla made $32 million through .ai domain registrations in 2023 alone.
Anguilla has been working with the US-based firm Identity Digital to manage the influx of registrations since 2024.
Although he’s an early investor in .ai domains, Shah said he doesn’t think they’re going to be lucrative long-term.
“Long-term, I think the interest is likely going to taper off,” he said. “I think .com domains will end up holding their value better.”
Business Insider reached out to Anguilla and Identity Digital for comment.
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