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September 2, 2025

3 Lessons from Anguilla’s Internet Domain Serendipity

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Beach in Anguilla, the small Caribbean island with the internet domain .ai that attracted Artificial Intelligence companies

Have you ever wondered about where .ai domains used to belong to?

Back in the 1980s when internet was a new thing, countries were given their own unique website domains. For United States the address would be .us, and for the United Kingdom the address would be .uk. This included the small Caribbean Island of Anguilla, which was given “.ai”.

Does that name ring a bell?

Recently the world has witnessed a rise on artificial intelligence (AI), and to brand themselves as an AI enterprise, some companies are paying Anguilla to register new websites with the .ai tag. One US tech boss Dharmesh Shah spent $700k on the address you.ai. This became a source of jackpot income for the small island.

However, it is not the first time that this happened. Tuvalu, a tiny island in the Pacific Ocean also signed an exclusive deal in 1998 to license its .tv domain name. Reports say this granted exclusive rights to US domain name registry firm, VeriSign in exchange for $2m a year, which later rose to $5m.

From this story we can learn about several lessons:

  1. Your trivial assets might mean a lot in the future

When Anguilla was assigned .ai, they did not think about 40 years later when Artificial Intelligence rocked the world, with chatbots such as ChatGPT emerging. Similarly, even if your company has any unique attributes that you feel might not benefit you in the future, it does no harm to you by keeping that unique attribute. Who knows you and your company might benefit from this in the future.

One example is NVIDIA. All gamers know the company as the designer of GPUs involved in commercial games. However years later, their consistent investment in a unique architectural attribute, parallel processing, and a software environment called CUDA allowed them to serve as the backbone for the AI revolution. NVIDIA’s years of nurturing this “unique attribute” positioned it not as just a gaming company, but as the fundamental backbone of the entire AI industry, catapulting its value and defining a new market.

  • Pivot your unique attributes to make it more unique

Anguilla experienced a big win when the world experienced AI boom and everyone started registering the domain for their company. But they turned it into a bigger win when they decided to pivot the asset’s purpose by rebranding an obscure national identifier to the global standard for artificial intelligence innovation. This strategic agility and flexibility in redefining an asset’s core value proposition is what differentiates between those who benefit from serendipity and those who create their own. We see this pattern of successful pivots time and again in the tech world, where the most valuable assets are often those that have been radically repurposed.

One example is Slack. The platform was not originally created for public use; it began its life as an internal communication tool built by Tiny Speck to coordinate development on a multiplayer game, Glitch. When the game was shut down, instead of discarding the tool, the team recognized its unique value proposition—a streamlined, channel-based system that was vastly superior to the email chains and existing chat clients plaguing the modern workplace. They then decided to pivot this asset’s purpose, from an internal game dev tool to a global SaaS product, which earned them billions of dollars in value and fundamentally changed how businesses operate.

  • Capitalize on your assets

Besides pivoting their assets, companies also need to make their assets secure enough so that the assets are still accessible in sudden unpredictable situations that might otherwise hinder usage. Anguillan government is a living example of this, having signed a five-year deal with Identity Digital, a US firm specializing in domain name registries, which migrated the domains to its own resilient global network, eliminating worries of disruption in the event of hurricanes.

The story of Anguilla’s asset is quirky, but inspiring because of how it was leveraged in the modern era. In a world that is becoming more and more turbulent, the next unexpected opportunity won’t be found solely in any domain. It is hidden in plain sight within your own organization—in an unused data set, an internal process, or a niche expertise. But the question is not about if any coincidence will happen, but whether you have the foresight to recognize your asset and the foundation in place to seize it. The time to start building that foundation is now.


At Vintage Management, we provide consultation services to business owners, including those who want to leverage on their untapped potentials. If you are one of them, please contact us here for a private discussion: https://seeandconnectsg.com/contact/

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