strategy Regrets? Here Are A Few

One of the more popular songs of all time is My Way. The English lyrics, adapted by Paul Anka from the French original, into a version specifically for Frank Sinatra, include “Regrets I’ve had a few. But then again, too few to mention.”

That got me to thinking about regrets and domain name investing. I used the Google command to search for the word regret on NamePros. It found 646 results.

I read through those hundreds of entries, not all of which are truly about regrets. In some cases, people were talking about decisions they did not regret, while in others the author was using the term in the context of a disagreement with some business.

But many of the entries do talk about genuine regrets, things the investor wished they had done differently. I decided it would be improper to link specific regrets, but reading the entries, along with my personal list of regrets, informed the following sections.

Registering Junk

I did not do a numerical analysis, but I am pretty sure regrets over registering poor quality names are the most frequent. Especially during promotions, or shortly after you think of an idea, it is so easy to just keep registering name after name.

A few tips:
  • If you find the addictive side of acquiring names getting out of hand, set limits for yourself. For example allow only one acquisition per week, or wait until you sell a name before acquiring more names.
  • Periodically taking a total break from acquisitions can be a good idea. The NamePros Blog article Is It Time For A Break From Domain Names? may be a helpful resource.
  • The idea of having an accountability partner, mentioned in Don't Do It Alone can also be helpful.

Pricing Regrets

Regrets related to pricing, both selling too low and setting unrealistically high prices, were frequently mentioned.

Pricing is hard. Here is a link to NamePros discussions that used the tag ‘pricing’. Lots of good advice to be found on the linked discussions.

While you should not always price as others do, it can be helpful, and is relatively easy, to see how domain names similar to yours are priced: How Are Investors Pricing Their Domain Names?

Particularly if you sell domains in emerging technologies and trends, be sure to reprice your inventory periodically.

Regrets About Offers

There was some discussion on how stressful it is to reject high-value offers. If a truly significant offer, you might want to discuss it with a trusted friend within the domain community before deciding.

On the other side of the coin, several expressed regrets after accepting a modest offer, particularly if they subsequently learned the buyer had deep pockets.

When you accept an offer that is somewhat lower than you hoped, that can still be the right decision if you can do better things with those funds. Will accepting this offer allow me to build a stronger overall portfolio?

For this, as with many other regrets, once a decision is made, don’t second guess your decision.

Missed Opportunities

Domaining would be easy with a time machine. Some expressed regret over missing out on opportunities.

Those opportunities could be a term that suddenly became really hot, such as ‘ETH’, or an extension that grew in popularity, like .io some years ago or .xyz more recently.

The NamePros Blog article Catching Trains and Avoiding Train Wrecks may be helpful.

In other cases, regrets were expressed over not spending enough and letting a great name slip away.


While most of the domain name community is honourable, unfortunately a few have fallen for scams of one kind or another. It is always good to be cautious when dealing with significant amounts with someone, or some business, that you do not know.

Remember that NamePros has a Warnings and Alerts section.


Perhaps the hardest regrets to deal with are situations where you made a mistake. Maybe you acquired a misspelled name, or fell for the capital-I, small-l switch, or bid on a name without realizing that it carried a premium renewal fee.

I covered Avoiding Costly Mistakes As A Domain Investor.

Many mistakes can be avoided by simply copying the name from the registration box, or auction entry, and pasting it into a Google search.

Too many ignore fine print, but it is important to pay attention to the terms in all agreements, and the details on things like length of grace period.

Overlooking The Key Idea

It is easy to become attached to a name that you think is really clever, and lose sight of the key point: you want names that will be valuable to a business or an organization.

Searching terms from business names on LinkedIn or in the OpenCorporates directory should be part of your evaluation process. That is not to say that a term without much current use always has little value.

Not Knowing When To Let Go

The sunk cost fallacy can make us keep renewing names that we should liquidate, or even simply drop. It is hard when you have invested significantly in a domain name just to let it go, but that is sometimes the right decision.

Falling For Appraisal Valuations

Automated domain name appraisal systems are among the most hotly discussed topics within the community. It is so easy, and often free, to do them, that it can be hard not to consult automated appraisals. Some expressed regret at letting automated valuations influence their decisions to acquire, or not acquire, a domain name.

One suggestion I would make is do your own complete analysis on a domain name first, including a tentative decision on how much you are willing to bid or whether you want to register it, and only then check an appraisal as a second opinion.

Also, look at the appraisal not for price, but rather for additional information, such as on comparator sales or search statistics.

Regret Not Using Resources

When I wrote the guide Finding Expiring and Expired Domain Names, on using the site, I expressed the regret that I did not use the site from the very beginning of my domain investing career.

It is so easy to use tools and sites such as NameBio, dotDB, OpenCorporates and many others, there is no reason for any investor not to become proficient in the various tools and resources during the early months of the domaining journey.

I covered some of these tools in the following NamePros Blog articles:
Lost Time

Every day that you have a domain name is an opportunity. That may be the day the domain name is discovered by a potential buyer. Don’t miss opportunities through delay in listing on a marketplace or implementing an active lander. Of course the 60 day transfer lock may influence how you list in the early months.

Check out the article The Many Ways That People Might Discover Your Domain Name.

Getting on the registration stream through a fast transfer network helps improve visibility of your name. We covered that in Domain Investing: Just the Basics - Part 2.

Ignoring Competition

Both in acquisition decisions, and in pricing, I regret that in the early years I did not adequately consider names on the market that would be direct competition. This is particularly important if you are considering a name in a TLD other than .com.

The price you can probably get for say a .co or .net will depend on the status of the same term in extensions such as .com, .io, .org and .xyz. You may have a great term in .net, but if the same term in .com is listed for sale at $3500, that will limit the price you can ask, unless there is some reason that the .net is a particularly appropriate match with the term.

While we should probably redo the poll, the article After .COM What Comes Next? is one view of the relative ordering of popular general-purpose TLDs.

Your ideal situation is when the .com is developed and not available for sale, and other strong alternatives are highly priced, or developed as well.

Not Adequately Appreciating Flexible Names

Some rather narrow names do sell at high prices. However, the longer I have been in domain investing, the more I have come to appreciate names that are elegant and special, but in addition could be applied in multiple sectors and niches. I regret some of the narrow application choices I made.

When I am seriously acquiring a domain name, I now try to write down at least five different reasonable applications for that name.

This doesn’t take long, and it really helps me focus on both whether the name has legitimate business use and how many different ways the name could be used. For example, on a name I recently acquired my list was: “cybersecurity, coaching, reputation management, consulting, industrial safety.”

Keeping Reflective Records

Even though I always kept records, I have come to regret that sometimes those records were not sufficiently complete.

It should be possible to go back months or years later, and have a clear view of the metrics when you acquired the name, and your rationale for acquisition. What sectors did you see as applications? How many businesses was the term used in? What was the status of competitor names?

A different type of record is related to keeping track of every offer or price request on a name, what buy-it-now pricing you had in place, what your counter offer was, and so on. You will need precise information on invested costs for tax purposes.

Most of us operate alone, but work as though you must report and justify each decision to a boss.

Not Being On NamePros

Someone expressed the regret that they did not start on NamePros earlier. Being part of a domain community can help you learn, make connections, stay realistic, and avoid many of the regrets mentioned above.

NamePros helps you stay on top of opportunities, get second opinions, be open to new ideas, and think more clearly about strategy. Taking part in a discussion, justifying a position in writing, will help you become an even better domain investor.

Of course NamePros can also help you do many other things, including buy or sell domain names.

Don’t Regret Your Regrets

It is important not to dwell on the past, what could have been.

Yes, reflection on what you regret can help you become a stronger domain name investor in the future. But don’t beat yourself up over regrets for past decisions.

The essential way to learn most things includes struggling, making a few mistakes along the way. Domain investing is no different.

The song ends with these lyrics The record shows I took the blows And did it my way. While none of the authors of the song had domain investing in mind, the idea of finding your own way, informed by the experiences of others, but not following them exactly, certainly applies to domain investing.

I hope this article has helped to focus on what we can learn from regrets. But it is just the beginning. Please share below your own regrets, and what you did in response.

A sincere thank you to all who shared their regrets across the past pages of NamePros, and those who will do so in this discussion. Thanks for making NamePros an incredible online community.
The views expressed on this page by users and staff are their own, not those of NamePros.
I liquidated several Squadhelp premiums a year ago for around $50 each. In the last couple months 2 have sold for $3000-$4500. You win some you lose some unfortunately.
This is very valuable thank you. I have a lot of domains that I have bought over the years with the intention of developing them into websites. However, I was recently been approached by a domain broker who made me a high offer for one of my domains ($2000). While I was not actively looking to sell my domains, I looked further in to it and discovered a whole new world. I am shocked that people make this much money over domain names!
Can you pay for this human or A.I.-operated service?
I may misunderstand the question. My proposal did not see engaging a paid service, but rather pair up with another domainer, or more simply someone not in domains. It is usually good to explain rationale and plans to someone, even if they do not know domains in detail. For many of us that happens naturally with a family member. For others, they engage with another domainer to talk through plans.

There is in principle nothing wrong with a paid service. Consultants and experts exist in almost anything. One would want to be sure the person has your best interests in mind, is knowledgeable, someone you feel comfortable working with.

NamePros, and domainer events, provide a great means for interacting.

Could AI be helpful. Possibly. In same way that investing and early stage legal investigations draw upon smart systems, it is possible here too. Not sure if such exist, beyond the appraisal systems, that most consider not very sophisticated or smart.

Could AI be helpful. Possibly. In same way that investing and early stage legal investigations draw upon smart systems, it is possible here too. Not sure if such exist, beyond the appraisal systems, that most consider not very sophisticated or smart.
For me it would be helpful to remove all emotion and excuses from the equation, being an emotional barrel of excuses. When you go to the bank and ask to borrow money they require one of two things, collateral or a profitable business. I'd prefer, insofar as a mentor, to interact with an emotionless machine. Human inputs her or his objectives and machine outputs a plan (based within your time and financial limitations). Your relationship with the machine is based on it checking that you completed activities set out in its plan. Something like that could change this industry. Does it exist? If no how could it be built?
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