Tech founder Dharmesh Shah paid Anguilla $700,000 to use the .ai domain

Anguilla, a British territory, has unexpectedly found itself in the spotlight thanks to its .ai domain, which has become a valuable asset amid the surge of artificial intelligence. While many internet users are accustomed to domains like .com and .org, Anguilla's unique country code has recently attracted significant attention from tech entrepreneurs eager to capitalize on the AI trend. In a noteworthy development, tech entrepreneur Dharmesh Shah, co-founder and CTO of HubSpot, invested $700,000 to acquire the domain you.ai. This purchase highlights the escalating demand for .ai domains as entrepreneurs look to establish a presence in the rapidly evolving AI landscape. Shah expressed that while he typically favors .com domains, the potential of you.ai for a future project was too appealing to pass up. Shah envisions you.ai as a platform where users can create digital avatars to perform specific tasks on their behalf. Although he primarily invests in domains for personal projects rather than for resale, he has previously made headlines for acquiring chat.com for over $15 million, which he later sold to ChatGPT for an undisclosed amount. His portfolio also includes several other .ai-related domains such as simple.ai, easy.ai, and chess.ai. The interest in .ai domains has skyrocketed, with the number of registered .ai domains soaring from just 40,000 at the start of 2020 to approximately 859,000 by August 2025. A recent report from the International Monetary Fund revealed that Anguilla generated an astonishing $32 million from .ai domain registrations in 2023 alone. To manage this influx, Anguilla has partnered with the US-based firm Identity Digital since 2024. Despite his early investment in the .ai domain space, Shah remains skeptical about their long-term value. He noted, "I think the interest is likely going to taper off. I think .com domains will end up holding their value better." As Anguilla continues to navigate this unexpected revenue stream, the future of .ai domains remains a topic of intrigue in the tech community.