What's in a name? According to GoDaddy, as of 2022, only five domain names have sold for more than $30 million, with the top spot going to CarInsurance.com at a sale price of $49.7 million. If estimates are accurate, it might need to add a sixth contender. OpenAI reportedly bought Chat.com for over $35 million, with at least some of that paid in shares.

On Wednesday, Sam Altman cryptically posted "chat.com" on X. Of course, the URL redirects to ChatGPT's homepage. Speculation is that OpenAI wanted a short domain name, but those guesses are dubious since it already owns ai.com, which it bought last year for around $11 million. The company most likely wants to just drop the "GPT" from its current domain. What is more interesting is the transaction.

The Verge notes that HubSpot founder Dharmesh Shah bought the domain for $15.5 million early last year. He wanted it for a project that never came to fruition. However, he figured he could still sell it for more than he paid, considering the direction of AI and the proliferation of chatbot assistants.

"The reason I bought chat.com is simple: I think Chat-based UX (#ChatUX) is the next big thing in software," Shah posted on LinkedIn. "Communicating with computers/software through a natural language interface is much more intuitive. This is made possible by Generative AI."

He sold it after a few months but did not disclose the price or who bought it, only stating that he sold it for more than he paid. However, after Altman made his "chat.com" post, Shah confirmed that the buyer was OpenAI and that he took his undisclosed payment in shares rather than cash (at least partially... maybe?). Shah explained that he took the stock investment because he has known Altman for over ten years and doesn't like profiting off people he considers friends.

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Taking over $15.5 million in shares is hardly "not profiting." However, Shah looks at it as an investment. If OpenAI does well, so does he; if it tanks, so does he. That said, it is a good bet that OpenAI will do just fine well into the future.

Shah humorously worded his post as a ChatGPT-o1 prompt. He defined the chatbot's character and then supplied relevant information. He then asked for it to guess the transaction price range and percentage he took in shares. It was, of course, a faux prompt without an answer, but that didn't stop followers from plugging it into ChatGPT.

One X user posted a response showing an estimated sale price of $18.6 million to $23.25 million with 50-70 percent as OpenAI shares. The estimated value in shares was $9.3 to $16.3 million. It seems like a fair guess. We got a different but relatively similar answer from ChatGPT-4 ($20 to $30 million and 50-75 percent, or $10 to $22.5 million in shares), but who knows? As we have seen, chatbots can spew out some terribly inaccurate results, especially when math is involved. At least for now, Shah and Altman aren't sharing details.