Perplexity AI, the AI-powered search startup, has acquired the domain os.ai from Dharmesh Shah, founder and CTO of HubSpot. Shah confirmed the news in a LinkedIn post, stating that he could not disclose details of the deal.
“I have sold the domain os.ai to Perplexity,” Shah wrote. “I was already a shareholder in Perplexity before (I love the product, as do millions of others). Now I’m a somewhat larger shareholder.”
The domain now redirects to Perplexity AI’s agentic browser, Comet.
The announcement comes as tech companies explore platforms optimised for AI-native workflows. Shah has previously written about the idea of an operating system for the AI era.
“It makes complete sense for an OS for AI to exist. Every big technology shift brings a new kind of OS,” he said. “Decades ago, we saw the PC wars. Then the battle for the browser. After that, the fight for the mobile OS.”
The domain os.ai may signal Perplexity’s ambitions beyond search, potentially pointing to a broader product strategy. Perplexity CEO Aravind Srinivas had shared the news earlier in the day.
This is not Shah’s first major domain sale. In November last year, he sold chat.com to OpenAI. The domain, originally registered in September 1996, is considered one of the web’s longstanding properties. Shah had purchased it for $15.5 million, one of the highest known prices paid for a domain.
OpenAI did not disclose the acquisition amount, though estimates suggest it likely exceeded $15 million.