A $50 million property transaction temporarily collapsed after both parties consulted ChatGPT for advice on the deal, according to New York-based estate agent Ryan Serhant.
Serhant, who heads the American real estate group Serhant and appears in Netflix’s Owning Manhattan series, disclosed the incident on his Instagram account, which has over three million followers.
How the deal unravelled
According to Serhant’s account, the seller used ChatGPT to ask whether they should proceed at the agreed price. The AI tool advised against the sale. Simultaneously, the buyer asked the platform if they were overpaying, receiving an affirmative response.
The opposing advice from the same AI system nearly derailed months of negotiation work on the transaction.
Deal salvaged through direct negotiation
In a follow-up post, Serhant confirmed he had recovered the transaction by engaging directly with both parties.
“Our job is to interpret and provide perspective. I talked through the deal with the buyer and seller and pushed both parties back to the table,” he stated.
Serhant noted that AI “frames its assumptions to provide a coherent answer, not an objectively correct one” when responding to queries.
Industry implications
The incident highlights emerging challenges as artificial intelligence tools become more accessible to property market participants. The case demonstrates potential conflicts when buyers and sellers rely on AI-generated advice without professional context or market-specific knowledge.
The original Instagram post, published earlier this month, received more than 70,000 likes. Serhant’s firm specialises in high-value property transactions in the New York market.
