Advice

A few years ago, my wife jokingly described my daily work lifestyle as leisurely. In some ways, I thought of that as a badge of honor. I built my business in a way that gave me ample time during the day to run, play tennis, ride my bike, drive the kids after school, run errands, go out for lunch, and basically set my own schedule. I have time to do the things that I want and the things that help my family.

I sometimes think about a 2009 John Chow article and video about the “.com lifestyle” and it was something I hoped to emulate. I don’t really take many walks in the park or trips to the playground anymore, but my days are flexible. Quick sidebar – I stopped checking in on Chow’s videos when he (wrongly) declared domain investing dead in 2011.

Trenton Hughes posted a domain name question that drew more than 50 replies in the last two days. Trenton is launching a business called UnFounded Ventures, and he asked for feedback about which domain name he should use. The two domain name options, which he appears to already own, are UnFounded.CO and UnFoundedVentures.com:

I could use your help… Finally about to officially launch UnFounded Ventures!

Which domain should we use? https://t.co/wobPkxpgSA

Orhttps://t.co/tcYWjWeRGm

Appreciate your help!

— Trenton Hughes (@trentjhughes) April 8, 2024

My personal opinion is that he should go with the brand matching UnFoundedVentures.com domain name for the business website. There are several reasons for why I would choose this option.

Recently, I started buying non .com domain names here and there when I see a keyword that I think well-matches the extension. I’m not interested in sharing specifics with you, but I have bought .AI, .IO, .CO, .APP, and .DEV domain names in auction, in addition to .XYZ that I previously wrote about. Non .com domain names is a small percentage of my portfolio and a fraction of a percentage of inventory cost.

One word of caution is that some extensions have rules that need to be followed in order to use the domain name. I learned this after winning a .Dev domain name in auction at Namecheap. A day or two after setting the nameservers to Afternic, the domain name did not resolve to a landing page. I checked in with Afternic and the domain name was set up correctly there. I submitted a ticket at Namecheap to see what was preventing the domain name from resolving, and here’s what I was told:

Some deals take a very long time to finalize. I have had acquisition and sale negotiations that have gone on for years. Some deals get done and others die on the vine. If you don’t receive a response to an email you sent to a contact at a company, it is a good idea to check LinkedIn to see if they still work there.

I have been involved in many long term negotiations to buy domain names. Oftentimes, the domain name is not being used, so I follow-up every year or so to inquire if anything has changed. If the person with whom I am communicating has left the company, usually there will be some sort of email deliverability notice indicating an email address doesn’t function. This is not always the case. Here’s one such example.