Thoughts
AI & Domain Names
In March 2023, we oversaw the sale of Chat*com to Hubspot Founder Dharmesh Shah, for a now known $15.5M. Dharmesh is one of the savviest tech entrepreneurs of our generation and he has been known to acquire strategic, ultra-premium domain names such as Chat*com. Last week, he rolled out phase 1 of an experimental, AI driven domain name appraisal agent on his Agent*ai platform. When I first tested it, I texted Dharmesh some concerns about the results and he replied immediately that he was working on enhancing it and it was just underway. I have tested it several times since and it is much improved already. Here is my issue with this, which Dharmesh acknowledged. The most valuable exact match and category domains that we invest in and advise on, such as Chat*com, are, well, the most valuable, and since almost every transaction involving them since the Internet started is confidential, even the all powerful OZ (AI) is limited, at least until it can see behind confidentiality agreements. With that said, I love seeing the most innovative people investing in the domain name space. We are the lead investor in Atom, and they are on the cutting edge of deploying AI in the domain name industry.
Tried & True
Our team at Hilco Digital Assets advises on many of the most significant domain name asset sales and acquisitions that transact. I myself, have also been a 2X founder of market leading, category domain branded companies, as well as an investor in many more ultra-premium domains, which does carry weight with those we are negotiating a purchase or sale for/with. However, there is nothing more valuable than the CEO/Founders/Investors who are peers to those we are advising, discussing the different reasons why their exact match, category domain acquisition has been the most important strategic business decision they have made. To that end, we have added a page to our website, https://lnkd.in/eFS_NYXp, that features some of these CEO/Founders. These are articles, tweets, and videos, to go along with the end user guests I have on my Random Thoughts podcast. If you are senior management, an investor, or an aspiring entrepreneur, these stories from Gold*com, Home*com, Extend*com, Gravity*com, Teamwork*com, Public*com, to name a few, are very important.
All articles
- October 27, 2025
- October 19, 2025
- October 12, 2025
- October 5, 2025
- September 28, 2025
- September 21, 2025
- September 14, 2025
- September 7, 2025
- August 24, 2025
- August 17, 2025
- August 10, 2025
- August 3, 2025
- July 27, 2025
- July 20, 2025
- July 13, 2025
- July 6, 2025
- June 29, 2025
- June 22, 2025
- June 15, 2025
- June 8, 2025
- June 1, 2025
- May 25, 2025
- May 18, 2025
- May 11, 2025
- May 4, 2025
- April 27, 2025
- April 20, 2025
- April 13, 2025
- April 6, 2025
- March 30, 2025
- March 23, 2025
- March 16, 2025
- March 9, 2025
- March 2, 2025
- February 23, 2025
- February 9, 2025
- February 2, 2025
- January 26, 2025
- January 19, 2025
- January 12, 2025
- January 5, 2025
- December 29, 2024
- December 22, 2024
- December 15, 2024
- December 8, 2024
- December 1, 2024
- November 24, 2024
- November 17, 2024
- November 10, 2024
- November 3, 2024
- October 27, 2024
- October 20, 2024
- October 13, 2024
- October 6, 2024
- September 29, 2024
- September 22, 2024
- September 15, 2024
- September 8, 2024
- September 2, 2024
- August 25, 2024
- August 18, 2024
- August 11, 2024
- August 4, 2024
- July 28, 2024
- July 21, 2024
- July 14, 2024
- July 7, 2024
- June 30, 2024
- June 23, 2024
- June 16, 2024
- June 9, 2024
- June 2, 2024
- May 26, 2024
- May 19, 2024
- May 12, 2024
- May 5, 2024
- April 28, 2024
- April 21, 2024
- April 14, 2024
- April 7, 2024
- March 31, 2024
- March 24, 2024
- March 17, 2024
- March 10, 2024
- March 3, 2024
- February 25, 2024
- February 11, 2024
- February 4, 2024
- January 28, 2024
- January 21, 2024
- January 14, 2024
- January 7, 2024
- December 31, 2023
- December 24, 2023
- December 17, 2023
- December 10, 2023
- December 3, 2023
- November 26, 2023
- November 19, 2023
- November 12, 2023
- November 5, 2023
- October 29, 2023
- October 22, 2023
- October 15, 2023
- October 8, 2023
- October 1, 2023
- September 24, 2023
- September 10, 2023
- September 3, 2023
- August 27, 2023
- August 20, 2023
- August 13, 2023
- August 6, 2023
- July 30, 2023
- July 23, 2023
- July 16, 2023
- July 9, 2023
- July 2, 2023
- June 25, 2023
- June 18, 2023
- June 11, 2023
- June 4, 2023
- May 28, 2023
- May 21, 2023
- May 14, 2023
- May 7, 2023
- April 30, 2023
- April 23, 2023
- April 16, 2023
- April 9, 2023
- April 2, 2023
- March 26, 2023
- March 19, 2023
- March 12, 2023
- March 5, 2023
- February 26, 2023
- February 19, 2023
- February 12, 2023
- February 5, 2023
- January 29, 2023
- January 22, 2023
- January 15, 2023
- January 8, 2023
- January 1, 2023
- December 25, 2022
- December 18, 2022
- December 11, 2022
- December 4, 2022
- November 27, 2022
- November 20, 2022
- November 13, 2022
- November 6, 2022
- October 30, 2022
- October 23, 2022
- October 16, 2022
- October 9, 2022
- October 2, 2022
- September 25, 2022
- September 18, 2022
- September 11, 2022
- September 4, 2022
- August 28, 2022
- August 21, 2022
- August 14, 2022
- August 7, 2022
- July 31, 2022
- July 24, 2022
- July 17, 2022
- July 10, 2022
- July 3, 2022
- June 26, 2022
- June 19, 2022
- June 12, 2022
- June 5, 2022
- May 29, 2022
- May 22, 2022
- May 15, 2022
- May 8, 2022
- May 1, 2022
- April 24, 2022
- April 17, 2022
- April 10, 2022
- April 3, 2022
- March 27, 2022
- March 20, 2022