I was on the Clubhouse domain investor chat organized by Jen Sale last Friday evening, and the topic of domain investing mistakes was brought up. I did not speak out in the Clubhouse room, but I want to share a domain investing mistake I have made many times and will continue to make in the future.
After selling a domain name to a buyer, I occasionally go out to look for similar domain names that I think could also be appealing to the buyer. By way of a hypothetical example, if I sold DomainInvesting.com, I might try to buy DomainInvestor.com or DomainInvestment.com in a private acquisition or future auction. Because of my past success selling the similar domain name, I tend to be more aggressive than normal in buying the subsequent domain name(s). After all, I have my own comparable sale to know the potential resale value.