In March, HubSpot co-Founder Dharmesh Shah announced the acquisition of OS.ai for $150,000. In response to his post on X, Perplexity CEO Aravind Srinivas replied to Dharmesh to tell him he wanted to buy OS.ai. It looks like that happened.
Yesterday evening, Srinivas posted about OS.ai, and Dharmesh re-posted his comment:
And so it begins. https://t.co/3oAzQvO1uI
— dharmesh (@dharmesh) July 14, 2025
The OS.ai domain name has been registered at GoDaddy under Whois privacy, so an ownership change wouldn’t have been noticed via Whois records.
This is not the first time Dharmesh sold a domain name he had recently acquired to a leading AI company. In 2023, he acquired and re-sold Chat.com. OpenAI turned out to buy the buyer of Chat.com, and Dharmesh revealed he was able to obtain stock in the privately held company as part of the deal.
I reached out to Dharmesh on X early this morning to see if he was willing/able to share the sale price of OS.ai. Perhaps he was able to secure some stock in Perplexity, another privately-held AI high flyer. Regardless of that, this deal once again shows that Dharmesh knows how to choose great domain names and his investments are paying off even when he is acquiring great domain names for his own use.
Update: In a LinkedIn post, Dharmesh commented about the sale of OS.ai.
Dharmesh is leaning into the future of domain name assets: domains for equity. Right person, right timing, right assets.
This is where high-level domain strategy is going. We’re not there yet, which leaves top names with significant untapped upside as investment vehicles.
Had to be some communication reguarding OS.com ?
How many domains do I have where owner of the DOT APP , DOT AI …… even the DOT NET would like to have the DOT COM and they have done well in SEO with thier NON DOT COM but they still want the DOT COM – not for traffic – but for the brand…. That wont ever change – its always in the back of the business and consumers mind
Dharmesh also created the best domain AI appraisal tool.
I believe it’s launched under Agent.ai.
He should launch it with Value.ai, or Appraise. Ai, or Estimate.Ai.
Didn’t know he also got some equity with sale of Chat.com (wow)
LOL
Godaddy appraisal tool for this domain
os.ai
Estimated Value$2,624
LOL
It also appraises Cloud.AI at 2600 usd and breeze.ai at 2600 usd approx, with those values maybe working for 2017? But not during the AI Age.
.AI will never reach .com values for single words, but it’s going to be #2 for a while.
If companies want funding, they better signal they have AI, and VCs and angel investors screen companies and its talent for Ai chops these days. If these companies also have a great single word .COM, that also will signal CRED and Hustle to get that name.
BTW
I had probably the 5th or 4th best .AI domain portfolio in 2016, as the gentleman from Ukraine had the second best in my opinion, and he provided documentation of the .ai domains and owners at the time.
Mind you, just about every single word in .AI was avail to register in 2016. Over 90 percent of the .AI domains regged at that time related to Anguilla. Then the gent who ran the .AI registry was astute to see the AI repurpose upside. This extension exceeded expectations, but there were early naysayers comparing .ai to .mobi, but this was prior to the explosion of AI and the ai concomitant funding and advances in technologies.
People mock me for having sold a large portion of that portfolio for only about 900 K between 2017-2023, but I wasn’t certain .AI would stick. And the domain renewal fees have always been high. The leading .AI domain portfolio belong to an entrepreneur from China and he had some crazy sales to the big tech companies now in AI arms races. He also acquired about 20 of my .ai domains and he got great deals.
I even gave 5 .AI domains to friends who were starting .AI startups in 2017 — these companies are all worth fortunes now.
So, yes. I made mistakes in not just holding all those single one wonder .AI domains, but at least I still own about 50.