AI & Real Estate
A $50 Million Deal Almost Died Because of ChatGPT
A buyer and seller both asked AI if their penthouse deal was fair. It told them to walk. The problem was not the deal. It was the prompt.
By David Golovin · June 17, 2026 · 2 min read
A Manhattan penthouse sale that nearly fell apart at the closing table, because two people opened a chatbot.
How it unravelled
Ryan Serhant, the broker behind Netflix’s Owning Manhattan, had the deal all but done. Then the buyer and seller each typed the same thing into ChatGPT:
The conversation that nearly killed it
What the chatbot couldn’t see
The advice was not malicious. It was blind. It answered a question about a specific apartment as if it were trivia. What it never knew:
Strip that out and “you may be overpaying” is not analysis. It is a coin flip in a confident voice.
How Serhant pulled it back
He did not argue with the robot. He put the real story on camera and let the facts do the work:
He filmed the real deal
The building, the comps, and why the price held up.
The video reached both parties
It circulated back to the buyer and seller the chatbot had spooked.
The context closed the gap
The missing facts brought both sides back, and the sale closed.
The fix was not less AI. It was more facts.
Why this is the whole point of Roots
A chatbot with no data hands you a confident guess. We built the opposite. Roots’ AI runs on live MLS data: real prices, real rates, and the actual comparable sales for the home in front of you. With more than 22,000 assumable homes, thousands of them under 3%, the answer reflects the market, not a hunch.