ChatGPT Almost Derailed Ryan Serhant's $50 Million NYC Penthouse Deal
At Fortune's Brainstorm Tech conference, real estate broker Ryan Serhant disclosed that a $50 million New York City penthouse sale for his firm was nearly jeopardized by ChatGPT. The buyer consulted the AI, which advised against the purchase, leading to an eleventh-hour withdrawal. Serhant ultimately saved the high-stakes deal through traditional research and a widely viewed social media video, highlighting the limitations of artificial intelligence in complex transactions.
Celebrity real estate agent Ryan Serhant, founder and CEO of Serhant brokerage, revealed at Fortune's Brainstorm Tech conference that a $50 million New York City penthouse deal almost failed due to input from ChatGPT.
Serhant recounted that after a contentious negotiation, a $50 million deal sheet was issued for a trophy penthouse, an asset difficult to price due to a lack of comparable properties. At the last minute, the buyer consulted ChatGPT, asking if $50 million was too much. The chatbot responded affirmatively, prompting the buyer's broker to attempt to pull out of the deal.
Serhant described his reaction as blunt, telling the buyer's broker that the move was "dumb" and "stupid." He then had to relay the news to his client, the seller, who also turned to ChatGPT, asking if $50 million was too little given the buyer's withdrawal. ChatGPT then stated it was, in fact, too little.
To salvage the deal, Serhant utilized what he called "old-fashioned research" and "off-market context and data that LLMs can't scrape." He also posted a video about the situation on social media, which garnered approximately 3 million views within three hours. Both the buyer and seller reportedly saw the video and returned to the negotiation table, allowing the deal to close.
Serhant argued that AI models understand the history of the internet but lack foresight and knowledge beyond publicly scraped data from platforms like Reddit, Zillow, or Realtor.com. This incident contributes to an ongoing public debate Serhant has been involved in regarding whether AI enhances or replaces real estate agents.
Andrew C. Spieler, a distinguished professor in business and finance at Hofstra University, previously told Fortune in March 2024 that real estate agents are becoming more akin to travel agents, as much information is now available online, reducing buyers' dependence on agents as "gatekeepers" of MLS listings. However, Serhant contended that real estate agents remain crucial, especially for wealthier clients, who seek guidance, someone to defer to, and accountability if issues arise.
According to Fortune, Serhant concluded by stating, "People hate being sold, but they love shopping with friends," emphasizing the human element in high-value transactions.
