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**AI.com Is for Sale. Asking Price? $100 Million**

Larry Fischer, a veteran Brooklyn domain broker, hopes to convince the likes of OpenAI to do a deal that's likely to break records.

By Akash Pasricha

Mar 1, 2025, 6:00am PST

Deep in Queens, New York, out near John F. Kennedy Airport, Larry Fischer was distraught. One of his favorite Italian joints—Don Peppe, the place where he lunched with Facebook's lawyers after selling them Messenger.com in 2014—had closed for vacation this past week. It had seemed like a fitting place for our conversation about another domain name deal he's got in the works that he hopes can be even higher profile. "You don't know how bummed I am," he said.

Fischer, a 62-year-old Brooklyn native, steered us to another of his favorite nearby haunts on 153rd Avenue. As pasta alla genovese and a carafe of Montepulciano arrived, Fischer, one of the world's leading domain brokers, uncorked the details on his next blockbuster project: the sale of AI.com, which he thinks can fetch more than $100 million. (He will begin accepting offers this weekend.)

"If somebody is looking to sell a top-tier domain, I am the guy they call," said Fischer. "I have a reputation for being able to get the best price."

Fischer has spent nearly 30 years buying, selling, and brokering deals for marquee internet domains. On top of Messenger.com, his greatest hits include selling Skincare.com to L'Oréal in 2015, selling Teams.com to Microsoft in 2020, and selling Chat.com in 2022 to HubSpot co-founder Dharmesh Shah, who quickly flipped it to OpenAI.

But a nine-figure deal wouldn't just be an order of magnitude larger than any of those sales—it would be the largest known domain sale ever, surpassing MicroStrategy's $30 million sale of Voice.com in 2019. Of course, it's hard to know for certain because the buying and selling of domains usually occurs in an opaque gray market through brokers like Fischer, who ranks in a small group handling the largest sales.

"I've been drooling about the day that AI.com would sell," said Fischer, who is also working on finding buyers for VR.com, Coding.com, and Kitchen.com. "The owner has a winning lottery ticket, and the only thing left is determining what that jackpot is."

Fischer won't reveal who owns AI.com but agreed to pass on a note from the owner to me. In the note, the owner said purchasing the domain "didn't have anything to do with the growth of Artificial Intelligence in recent years, it was just simply to have a vanity domain name that so happened to be my initials....I happened to be there ahead of its time. I'm truly blessed."

To begin attracting attention from prospective buyers, the owner has adopted a clever sales tactic in the last few months, continually redirecting AI.com to new sites. For a while, it went to ChatGPT's website. These days, it goes to DeepSeek's. The ploy has had an amusing ripple effect: A slew of headlines has mistakenly claimed that one of these companies had already secured the domain.

Still, even with the AI craze as manic as it is, the market value of AI.com—and whether it's worth nine figures—is anyone's guess. "I don't think it's going to get there, but if it does get there, I think it's a good sign that we might be starting to get back into a dot-com bubble," said Ron Berman, a Wharton School associate professor who focuses on digital advertising. Most of the data around purchase prices and traffic are shrouded in privacy, Berman added. "I'm not aware of any science that gives us valuations for these things," he said. “I don't think there's even research that tries to say what makes them more or less valuable."

Big fish like OpenAI, Microsoft, Google, Meta Platforms, or, yes, DeepSeek would be logical buyers for AI.com. They're among the few firms or people who could afford such a purchase. HubSpot's Shah paid $15.5 million for Chat.com (who later suggested he sold it to OpenAI for that amount of equity in the company). Fischer said he's also thinking a crypto mogul in the market for collectibles could be a potential buyer.

If anyone can get $100 million for AI.com, it's Fischer, who started honing his salesperson's instincts even before domains became important. As he bounced between accounting and headhunting jobs in the early '90s, Fischer called phone companies to secure hundreds of phone numbers and then struck deals with several newspapers allowing them to use the numbers for the dating personals ads.

In 1995, he put an old newspaper clipping from The Wall Street Journal about domain names on his shelf. Two years later, he stumbled on the clipping again when the shelf "literally fell" on his head, he recalled. Next thing he knew he was snapping them up for $100 a piece. Among the first names he bought were Brothers.com, Sisters.com, and Stockquotes.com.

Initially, Fischer struggled to figure out how to sell his stockpile. "My wife put her foot down: If I couldn't turn this into something that generated cash flow, it was over." But Portuguese.com changed his luck. Fischer sold it for $3,000, and soon after, he sold Return.com for a "low six-figure" sum after buying each for $100. That put him "back on top and officially on a roll."

Unsurprisingly, the dot-com crash stifled Fischer's momentum for a few years. But in the early 2000s, he and a prominent attorney in the domain world, Ari Goldberger, started a new venture called SmartName.com. The business helped domain owners or "domainers" generate revenue from advertisers who paid to stick their links on the domain's plain and unremarkable landing pages (Stockquote.com, for example, is still set up like this). The business grew to manage more than 100,000 domains and sold in 2006 for $16.5 million.

Around that time is when Fischer started ramping up his brokerage services. Over the years, he has represented clients that bought or sold iconic names like MyWorld.com, Friend.com, and Marketing.com. He closed most deals from the unfinished basement of a Park Slope neighborhood Brooklyn townhouse he has owned since 1993, with wood-paneled walls and "ugly shag pink carpeting," his son Jeff Fischer said. (The younger Fischer, who owns Jeffrey.org, has been helping out with his dad's business part-time since he was a teenager.)

Leon Bensonoff, another veteran domainer who regularly buys and sells domains on his own, said he has turned to Fischer over the years for help with "impossible deals." Fischer helped him buy Chat.com off CBS in 2014 and then sell it eight years later. Fischer has a knack for convincing people who don't want to part ways with a domain that it's time to sell, Bensonoff said. He also has a way of making buyers feel like he's doing them a favor by selling them domains at whatever price they're paying, Bensonoff added.

Over the years, Fischer himself has developed an attachment to certain names he's unwilling to part with. He grew up an avid follower of pop art but could never afford his favorite artists' work. So in 1997, he bought Andy Warhol.com and has been sitting on it ever since, despite several attempts from the Andy Warhol Foundation to claw it back. "It's my painting. It's my artwork," he said. (The site is the same Warhol fan page Fischer set up 26 years ago.)

After scores of deals, Fischer said he's addicted to the feeling of outdoing himself, driven by the high he gets from closing seven and eight-figure deals. "It's just like when my kids are born. It's the same feeling."

As we finished dinner and got up from the table, I asked how he'll feel when AI.com sells. "Triplets," he said.