{"id":1513,"date":"2026-06-16T07:09:56","date_gmt":"2026-06-16T07:09:56","guid":{"rendered":"https:\/\/crosscountrymovingteams.com\/?p=1513"},"modified":"2026-06-16T07:09:56","modified_gmt":"2026-06-16T07:09:56","slug":"a-chatgpt-prompt-almost-killed-ryan-serhants-50-million-nyc-penthouse-deal-heres-how-he-saved-it","status":"publish","type":"post","link":"https:\/\/crosscountrymovingteams.com\/?p=1513","title":{"rendered":"A ChatGPT prompt almost killed Ryan Serhant\u2019s $50 million NYC penthouse deal. Here\u2019s how he saved it"},"content":{"rendered":"
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When asked by Fortune<\/em>\u2019s Term Sheet Editor Allie Garfinkle about what happens when AI goes wrong, Serhant, the founder and CEO of his namesake brokerage Serhant, remembered a time when he was selling a New York City penthouse.\u00a0<\/p>\n

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It was the kind of trophy asset that\u2019s infamously hard to price because it\u2019s impossible to find comparisons. After what Serhant described as a \u201ccontentious\u201d back-and-forth\u2014he likened it to dueling \u201ckings of the world,\u201d with the buyer and the seller each wanting to win\u2014the deal sheet went out at $50 million flat. Then, at the 11th hour, it nearly died.<\/p>\n

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That\u2019s because the buyer, Serhant said, went to ChatGPT and typed a version of \u201cI\u2019m looking to buy this, is $50 million too much?\u201d The chatbot said yes.\u00a0<\/p>\n

The buyer\u2019s broker then called Serhant to pull out of the deal because AI said it wasn\u2019t worth it. Unsurprisingly, Serhant\u2019s reaction was pretty blunt, telling the broker the move was \u201cdumb\u201d and \u201cstupid.\u201d<\/p>\n

Serhant recalled telling the buyer\u2019s broker \u201cyour client\u2019s incredibly smart and wealthy, isn\u2019t he using the data? He\u2019s like, \u2018I don\u2019t know what to tell you, man. Super intelligence just told him, \u2018Don\u2019t do this, it\u2019s not worth it.\u2019\u201d<\/p>\n

So then Serhant had to relay the bad news to his client, who did what \u201canyone would do in that situation,\u201d and turned to ChatGPT too.\u00a0<\/p>\n

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The client asked ChatGPT the inverse question: \u201cI have a buyer that no longer wants to spend [$50 million] because you told him not to. Is $50 million too little? And ChatGPT said, \u2018You know what, you\u2019re right, it is.\u2019\u201d<\/p>\n

To salvage the deal, the fix wasn\u2019t using more AI. It was using old-fashioned research like \u201coff-market context and data that LLMs can\u2019t scrape,\u201d Serhant said.\u00a0<\/p>\n

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He also went on to post a video about the debacle on social media, which he said racked up 3 million views in about three hours. Both clients saw it, both came back to the table, and the deal got done.\u00a0<\/p>\n

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AI models \u201cknow the history of the internet, they don\u2019t know the path forward, and they don\u2019t know what the internet, and Reddit, and Zillow and Realtor.com does not know,\u201d Serhant said. \u201cAnd we got the deal done, and now I can tell that story as a win and not as a fail.\u201d<\/p>\n

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This story is part of a larger debate he has been having publicly for a while about whether AI amplifies real estate agents or replaces them. It\u2019s a controversy that\u2019s been simmering for a couple of years now, with one award-winning professor telling Fortune <\/em>in March 2024 that real estate agents are becoming more like travel agents.<\/p>\n

\u201cIf you think about what an agent does for you, I think it\u2019s very different than what they used to do for you because so much more information is available on the internet,\u201d Andrew C. Spieler, a distinguished professor in business and finance at Hofstra University, told Fortune<\/em>.\u00a0<\/p>\n

Like travel agents, realtors were once the \u201cgatekeepers\u201d of information. They had access to MLS listings that consumers couldn\u2019t find on their own, so buyers had to be much more \u201cdependent\u201d on their agents to even start house hunting. But now, he argued, that information is more readily available.\u00a0<\/p>\n

Unsurprisingly, real estate agents beg to differ. Serhant, for example, said real estate agents are even more important to wealthier clients because they want to be told what to do, have someone to defer to, and if something goes wrong, someone to blame. AI can\u2019t absorb that, he said.<\/p>\n

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\u201cPeople hate being sold,\u201d Serhant said. \u201cBut they love shopping with friends.\u201d<\/p>\n<\/div>\n","protected":false},"excerpt":{"rendered":"

Broker Ryan Serhant explained how ChatGPT nearly blew up a $50M NYC penthouse sale\u2014and why he says AI still can’t replace a human in high-stakes deals.<\/p>\n","protected":false},"author":1,"featured_media":1512,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[218],"tags":[],"class_list":["post-1513","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-brainstorm-tech"],"yoast_head":"\nA ChatGPT prompt almost killed Ryan Serhant\u2019s $50 million NYC penthouse deal. 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