Domain Investing Mistake I Make Over and Over

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, I might try to buy or 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.

In many cases when I have done this, the buyer was either not interested in the other domain name or the price was beyond what the buyer was willing to pay. When the buyer was interested in an additional domain name, they typically expect a break on the price because of our past business. If I sold a domain name for $20,000, the buyer might only be willing to pay $10k or $15k for the other domain name, even if it is arguably better.

There are two primary reasons for why buyers don’t always want additional domain names. First, the domain name they bought from me was for a specific purpose. If the wanted the other domain name more, they probably tried to buy it. Second, the buyer already spent their budgeted funds on the domain name they bought from me. Allocating more spend for an additional domain name may not be feasible for them.

I would guesstimate that more than half the time I have tried this I have failed. I would also guesstimate that I’ve undersold the additional domain name(s) when I was successful. That said, I was happy to sell profitably, even less profitably than I hoped, when a buyer was interested.

Even though the fail rate is regularly high, it’s a mistake I make over and over again.

Elliot Silver
Elliot Silver
About The Author: Elliot Silver is an Internet entrepreneur and publisher of Elliot is also the founder and President of Top Notch Domains, LLC, a company that has closed eight figures in deals. Please read the Terms of Use page for additional information about the publisher, website comment policy, disclosures, and conflicts of interest. Reach out to Elliot: Twitter | Facebook | LinkedIn


  1. Elliot, I commend your courage for observing and speaking about your mistakes. We all make but keep our mouths shut afterwards. Thank you for teaching us valuable lessons in humility and self evaluation.

  2. I have been reading you blog for more than ten years now, but never heard you speak anywhere. Looking forward to hear your voice 🙂 Maybe we will see you in a DomainSherpa show soon?? Have a great day!

  3. yes…i had a short (4 letters) word (very common) in .ai that was acquired for xxxxx in january
    i also owned the same word in .io, and presented it to the company’s ceo after transaction closed

    they wanted it but nowhere near what they paid for the ,ai…which they used to rebrand the company from a 2 word .com

    • Hello Konstantinos,
      BINGO! ( Or maybe they just need only one Good domain )
      JAS 3/7/2021
      Gratefully and Respectfully, Jeff Schneider (CONTACT GROUP)
      We don’t Follow, We Create

  4. Hello Elliot,
    I appologize to you for firebombing your site , I am sure you remember it. If not , We felt the need to grab everyones attention on a vicious Lie perpetrated by , Well you know the story.
    Thanks for being upfront it will pay off in spades. We believe very strongly, that giving away Knowledge that you Covet, the world will come to your door. JAS 3/7/2021
    Gratefully and Respectfully, Jeff Schneider (CONTACT GROUP) We don’t Follow, We Create

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