He bought Chat.com and you.ai, and now he has sold OS.ai to this company!

In March this year, the domain name circle ushered in a sensational transaction: Dharmesh Shah acquired the ultra-short boutique domain name OS.ai for $150,000. He is the co-founder of HubSpot and the legendary buyer who bought Chat.com for $15.5 million in 2023-later the domain name was sold to OpenAI.

At that time, he said on the social platform that this was the only two-character .ai domain name he owned, and it was also one of the very few .ai suffixes he bought in his many years of investment, which shows how much he values it.

And the deal did not end there. A few months later, OS.ai changed hands again-the buyer was the AI search upstart Perplexity!

Perplexity officially acquired OS.ai, and the big boss turned into a shareholder!

According to Dharmesh himself, this transaction was not a traditional cash transaction, but was completed through equity swap. He said frankly:

"I was already a shareholder of Perplexity... Now I am a bigger shareholder."

In fact, as early as March when he just announced the purchase of OS.ai, Perplexity CEO Aravind Srinivas left a message under his post expressing interest in buying. Now, several months have passed, and the wish has come true, and the buyer is still him!

What's more, Perplexity has just released its own AI browser Comet recently, positioning it as "the operating system of the AI era". OS.ai is simply a tailor-made brand entrance for them.

Domain name + equity combination

This is not the first time that Dharmesh has turned a domain name into a strategic asset. In addition to Chat.com and OS.ai, there is another case that cannot be ignored:

you.ai - sold for $700,000, currently the highest transaction record in the history of .ai domain names, and it was also bought by him.

Three super domain names, three scenarios:

Chat.com→ sold to OpenAI in exchange for cooperation and equity;

you.ai→ purchased at a high price, not yet sold, but with great potential for self-use;

OS.ai→ sold to Perplexity, exchanged for equity to continue to bind high-quality projects.

This path of "buy high-quality products → sell terminals → exchange for equity" is simply a high-level template for domain name investment.

Why is OS.ai so valuable?

Don't look at it as only two letters. OS is almost a "universal currency" in the technology industry. It is the abbreviation of "Operating System" and is related to core infrastructure such as software, hardware, and browsers.

The .ai suffix has long become the standard for AI startups. OS.ai is short, professional, and easy to remember. It is a "dream combination" that the entire AI industry is scrambling for.

Coupled with the endorsement of star projects such as Perplexity, OS.ai is not only a domain name, but also a traffic entrance, brand identity and strategic bargaining chip.

Can domain names be played like this? Lessons for investors

From this OS.ai transaction, we can see that domain names are far more than just a website address. Under Dharmesh's operation, it can become the core entrance of a corporate brand, a bargaining chip for strategic cooperation, and even a capital tool for exchanging equity.

This "buy domain names for equity" gameplay may be far-fetched for ordinary investors like us, but it also provides a clear inspiration direction - high-quality domain names have strong brand premium capabilities and potential monetization space.