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Ryan Serhant says a $50 million deal almost collapsed because of ChatGPT

2026-06-18 97 Dailymotion

At Fortune Brainstorm Tech, Serhant founder and CEO Ryan Serhant told the story of a $50 million penthouse deal that nearly fell apart after the buyer asked ChatGPT whether the property was worth the price and got a no.

In the end, Serhant said the deal got done using something AI couldn't access: off-market context.

“[LLMs] know the history of the internet,” he said. “They don't know path forward.”