Combo deal? Dharmesh Shah teases about selling price of Chat.com to OpenAI

Dharmesh Shah, founder of HubSpot, acquired the domain name Chat.com for $15.5 million dollars in the spring of 2023.

Known for his busy mind that creates projects, Mr. Shah acquired the domain to host yet another of his AI-driven creations and not for reselling.

That being said, never underestimate the power of money, as Chat.com has been sold once again. The buyer is OpenAI, creators of ChatGPT.

Sam Altman, the CEO of OpenAI revealed today that his company is the buyer; the domain Chat.com now forwards to ChatGPT.

So the question arising from this news is how much did Dharmesh Shah sell the domain Chat.com for?

He didn’t offer any numbers but provided instead a well-tailored prompt to be used with ChatGPT!

Very clever, Dharmesh! 🙂

We fed that prompt to ChatGPT and this is what it came back with:

Dharmesh likely sold chat.com for an amount that would fit the unique context of the transaction—high value but not profit-focused, given his relationship with OpenAI and Sam Altman. Here’s a thought process for estimating the sale price:

  • Dharmesh’s purchase price of $15.5M: This sets a minimum baseline, especially as he tends not to sell at a loss. Given the strategic importance of the domain to OpenAI, the value could easily be above this figure. A range of $15.5M to $20M would be reasonable for a breakeven or modestly profitable deal.
  • Relationship-based discount: Since he doesn’t like profiting off friends and has a personal connection to OpenAI, a traditional “high premium” domain price seems unlikely here. The sale may have been more about OpenAI’s fit with *chat.com* rather than maximizing profit, suggesting that the range likely stayed below typical high-value sales for prime domains.
  • OpenAI shares: Given Dharmesh’s enthusiasm for OpenAI and his prior investment, it’s plausible that part of the sale involved equity. If he truly loves OpenAI’s mission and wants a long-term stake, shares could be highly appealing. Assuming he structured 20-40% of the sale in shares aligns with his goals and reduces the cash component while increasing OpenAI equity.

Estimated sale price: Based on these points, Dharmesh might have sold chat.com for around $15.5M to $18M, with $3M to $7M in OpenAI shares. The deal’s structure likely balanced his costs, loyalty, and a strategic partnership through equity. This range accounts for the combination of financial value and Dharmesh’s apparent desire for a meaningful, long-term connection with OpenAI.

Now this is how you close a combo deal! 🙂

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