At the Fortune Brainstorm Tech conference, celebrity real estate agent Ryan Serhant said ChatGPT nearly blew a $50 million deal for his firm. Serhant, founder and CEO of Serhant, recalled selling a New York City penthouse when, after a "contentious" back-and-forth, the deal sheet went out at $50 million flat. The buyer typed into ChatGPT a version of "I'm looking to buy this, is $50 million too much?" The chatbot said yes, and the buyer's broker called Serhant to pull out of the deal because AI said it wasn't worth it. Serhant called the move "dumb" and "stupid." His client then 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, Serhant used "off-market context and data that LLMs can't scrape." He posted a video about the debacle on social media, which racked up 3 million views in about three hours. Both clients saw it, both came back to the table, and the deal got done.