Artificial Intelligence

How AI Derailed a $50M Real Estate Deal: Lessons from Ryan Serhant's Tech Mishap

· 5 min read

Ryan Serhant and ChatGPT

High-profile real estate broker Ryan Serhant (pictured) recently disclosed that OpenAI's ChatGPT nearly derailed a substantial $50 million property transaction.

The television personality, widely recognized from Bravo's Million Dollar Listing franchise, shared the incident with his substantial social media audience of over three million followers on Instagram.

According to Serhant, the deal unraveled after months of careful negotiation and preparation.

Using ChatGPT

The broker described both parties as sophisticated and well-informed—"very smart buyer, very smart seller."

Yet in the final stages, the seller consulted ChatGPT about whether the asking price was appropriate. The AI recommended against proceeding.

Simultaneously, the prospective buyer queried the same platform about potential overpayment—receiving an affirmative response.

It is a good job I'm here when ChatGPT offered opposite answers."

In a subsequent update, Serhant confirmed he successfully salvaged the transaction.

He remarked: "It is a good job I'm here when ChatGPT offered opposite answers.

"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."

Addressing the limitations of AI-generated guidance, Serhant noted that such systems "frame assumptions to provide a coherent answer, not an objectively correct one" when responding to queries.

The initial social media post, published earlier this month, garnered significant engagement with over 70,000 likes.

Ryan Serhant currently stars in Owning Manhattan on Netflix and the Million Dollar Listing series. He specializes in high-end residential properties and serves as Chief Executive of Serhant, a prominent American real estate brokerage.

The post Reality TV star Ryan Serhant claims AI 'blew up his $50M deal' appeared first on The Negotiator.