A ChatGPT prompt almost killed Ryan Serhant’s $50 million NYC penthouse deal. Here’s how he saved it

AI can drudge up untrustworthy sources or just feel kind of “off,” but the technology has also been pretty consequential for some business owners. In fact, celebrity real estate agent Ryan Serhant said at Fortune’s Brainstorm Tech conference last week that Chat GPT nearly blew a $50 million deal for his firm. When asked by Fortune’s Term Sheet Editor Allie Garfinkle about what happens when AI goes wrong, Serhant, the founder and CEO of his namesake brokerage Serhant, remembered a time when he was selling a New York City penthouse. It was the kind of trophy asset that’s infamously hard to price because it’s impossible to find comparisons. After what Serhant described as a “contentious” back-and-forth—he likened it to dueling “kings of the world,” with the buyer and the seller each wanting to win—the deal sheet went out at $50 million flat. Then, at the 11th hour, it nearly died. That’s because the buyer, Serhant said, went to ChatGPT and typed a version of “I’m looking to buy this, is $50 million too much?” The chatbot said yes. The buyer’s broker then called Serhant to pull out of the deal because AI said it wasn’t worth it. Unsurprisingly, Serhant’s reaction was pretty blunt, telling the broker the move was “dumb” and “stupid.” Serhant recalled telling the buyer’s broker “your client’s incredibly smart and wealthy, isn’t he using the data? He’s like, ‘I don’t know what to tell you, man. Super intelligence just told him, ‘Don’t do this, it’s not worth it.’” So then Serhant had to relay the bad news to his client, who did what “anyone would do in that situation,” and turned to ChatGPT too. The client asked ChatGPT the inverse question: “I have a buyer that no longer wants to spend [$50 million] because you told him not to. Is $50 million too little? And ChatGPT said, ‘You know what, you’re right, it is.’” To salvage the deal, the fix wasn’t using more AI. It was using old-fashioned research like “off-ma