Buying Domain Names

I don’t closely track the percentage of domain extensions in my portfolio. I could have 75% .com or I could have 99% .com domain names in my portfolio, and the only implication is higher (in general) renewal costs. Because I buy more domain names that I sell, my portfolio has been growing each year, so tracking the increase in renewal costs isn’t really helpful in seeing how the percentage of .com domain names is changing.

I’ve primarily invested in .com domain names since I started my business 20 years ago. I think great one and two word .com domain names are the most desirable assets for businesses around the world, and I have always wanted to invest in domain names like these that sell themselves.

In early February, I noticed that Kicks.com changed hands. The valuable one word .com domain name had been owned by Reflex, and transferred to a registrant called Domain Licenses Limited, which I believe is an entity that acquires and/or holds domain names on behalf of other companies.

I detected this Whois change with the help of the DomainTools Registrant Monitor.

Looks like https://t.co/d4ITR8l1j0 changed hands.

The domain name was previously registered at Namecheap and owned by Reflex. It is now registered at Com Laude and owned by Domain Licenses Limited.

The domain name does not yet resolve.

Spotted via @DomainTools.

— Elliot Silver (@DInvesting) February 3, 2025

HubSpot Founder Dharmesh Shah announced another domain name acquisition today. Dharmesh acquired OS.ai for $150,000. He announced the acquisition and shared his rationale for buying the domain name in a post on X:

LEAKED NEWS: I acquired the domain name os .ai for $150,000 (just saw the transaction reported on some online sources).

It’s the only two character domain name I own and one of the handful of .ai domains I’ve bought over the years.

I have some ideas on what kind of… pic.twitter.com/9g98fjD6Jo

— dharmesh (@dharmesh) March 12, 2025

The post received numerous responses, as Dharmesh invited people to share their ultra-premium domain names, offering to give a valuation from a new Agent.ai agent that is under development.

One response to the post didn’t include a domain name to evaluate. Aravind Srinivas, CEO of Perplexity, replied to Dharmesh to let him know he would like to buy OS.ai:

I have a $20/month paid account at OpenAi. I primarily use it to access ChatGPT – and I always use Chat.com to navigate to the website. One of the ways I use the platform is to generate keyword lists that I use to search for and register domain names.

Oftentimes, these keyword lists revolve around a specific topic, and I will append the lists to a different keyword. For instance, and this is just a made up example based on a current “hot” trend, I might ask Chat.com to generate a list of 100 popular scientific keywords that an 8th grader would know and then append AI.com to the end. I always give an example, such as MeteorAI.com in this case, so the tool can understand exactly what I am seeking.