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Chat.com Profitably Resold for 8 Figures

In March of this year, I reported on the sale of Chat.com. The domain name was acquired by HubSpot Co-Founder Dharmesh Shah for more than $10 million USD. The exact acquisition price wasn’t revealed by either party. That deal had been brokered by Hilco Digital’s Andrew Miller and Larry Fischer.

This morning, Dharmesh revealed that he resold the domain name for a profit, and he is donating $250,000 to Khan Academy:

YourRide.com Sold for $300k via Evergreen.com

I made an unexpected guest appearance this week on DomainSherpa. It’s the first time in many years I’ve been seen on the DS show with some of my favorite people in the domain industry – Jen Sale, Adam Strong, Ammar Kubba, and Jonathan Tenenbaum.

In this week’s episode, Jen Sale, who is CEO of Evergreen.com, announced her company brokered the sale of YourRide.com for $300,000. The domain name had been owned by Adam Strong’s company for nearly 20 years. Adam owns a large portfolio of tens of thousands of domain names and was also a cofounder of Evergreen.

Once the domain name sale is archived by NameBio and DNJournal, it will rank in the top 10 domain name sales of the year (to date). YourRide.com is a very nice domain name, and selling it for $300k is impressive.

I can’t embed the Domain Sherpa show, so you’ll have to visit the website to watch.

Chat.com Acquired for More than $10 Million


Last week, Hilco Digital’s Andrew Miller shared that he and Larry Fischer brokered the sale of the Chat.com domain name. Andrew mentioned that it was “the most significant domain asset transaction in our combined 50+ years investing in and advising on premium domain names.”

Given their involvement in the 2021 sale of Home.com coupled with the extraordinary value of Chat.com, my assumption has been that Chat.com sold for 8 figures ($10 million or more).

AI.com Now Forwarding to ChatGPT Website


Early this morning, Andy Booth tweeted about AI.com, asking if the domain name was acquired by ChatGPT. Andy presumably asked because the AI.com domain name is now forwarding to the ChatGPT website, a popular AI chatbot.

AI.com had long been owned by Future Media Architects (FMA). In September of 2021, I reported on the sale of AI.com. The deal was brokered by Saw.com, which has long represented FMA on its domain name sales. In my article about the sale, I shared what I understood to be the asking price of AI.com along with a comment from Saw.com Founder and CEO Jeff Gabriel:

Squadhelp Introduces AI Business Name Generator

Earlier this month when OpenAI’s ChatGPT chatbot was trending, I discussed some of the ways artificial intelligence (AI) could be used for domain investing. I cited a number of domain investors who shared the output of their ChatGPT queries on Twitter.

One area that wasn’t touched upon was how AI could be used to help people find brand names for their businesses. This morning, Squadhelp announced that it introduced an AI-based business name generation tool powered by GPT-3. The news was shared on Squadhelp’s Twitter page:

I Don’t Always Have to Win


I am a highly competitive person. Whether I am playing a tennis match against a friend or playing a board game with my family, I always want to win. This competitive drive often shows itself when I am negotiating to buy or sell a domain name. Like when I am playing boys against girls soccer with my family, sometimes it’s better to lose the competitive spirit for the betterment of all.

I regularly find myself in domain name negotiations where a gap exists between the price I’ve set and the “max” price a buyer has in mind. If the gulf is far too great, it’s easy to wish the prospect well and move on to other things. When the gap is more narrow, it sometimes comes down to who gives up first.

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