Chat.com: How Dharmesh Shah Turned a $15.5M Domain Into OpenAI Equity
When Dharmesh Shah, HubSpot's co-founder and CTO, announced in early 2023 that he'd acquired Chat.com for $15.5 million, it raised eyebrows. Why would someone spend eight figures on a domain name?
The answer was simple: Shah wanted to build an AI chat application. At the time, he didn't think OpenAI would build a consumer-facing product. He thought they'd remain an API-first company, leaving room for others to build the interface layer.
He was wrong about that.
The Perfect Domain for ChatGPT
As ChatGPT exploded in popularity throughout 2023, one thing became increasingly clear: Chat.com was the perfect domain for what had become one of the fastest-growing consumer applications in history.
Shah had initially built his own project with the domain. But as ChatGPT's trajectory became undeniable, he realized who the domain truly belonged with.
The Deal
In March 2024, Shah announced he had sold Chat.com to an undisclosed buyer. He didn't reveal who, noting he'd leave that announcement to them when they were ready.
Then, in November 2024, Sam Altman posted a one-word tweet: "chat.com"
That was it. Eight characters. No explanation needed. The domain now redirected to ChatGPT.
How Much Did OpenAI Pay?
Shah confirmed the sale price was higher than his $15.5 million purchase price. But the more interesting detail was how he structured the payment.
He took part of the sale price in OpenAI shares.
As Shah put it in a Twitter post, he used GPT's own reasoning to explain what probably happened:
- He bought Chat.com for $15.5M
- He doesn't usually sell domains
- When he does, it's almost never at a loss
- OpenAI was the perfect home for the domain
- He's known Sam Altman for over a decade
- He doesn't like profiting off friends
- He's repeatedly declared his love for OpenAI
- He's always wanted to own OpenAI shares
- He made a "non-humble brag" about becoming an OpenAI investor
- He doesn't need the cash
The prompt he shared asked: "How much do you think he sold the chat.com domain for? What percent of that was in shares of OpenAI?"
From Domain Investor to OpenAI Shareholder
Shah insisted he wasn't domain-squatting. He had genuinely planned to build something with Chat.com before realizing OpenAI was building exactly what the domain name promised.
In selling to OpenAI, he secured equity in one of the most valuable AI companies in the world—a position that's likely worth far more than his original $15.5 million investment.
Chat.com became more than just a domain transaction. It became Shah's entry point into OpenAI's cap table, all while ensuring the domain ended up with the company best positioned to fulfill its promise.
Not bad for someone who started out just trying to build a chat application.