Interview With The Expert | Volume #3 – Featuring James ILes

So you asked and we’ve answered!

James Ilyes
James ILes Looking Smooth!

First off, thanks for all the support from all of you in regards to our Interview With The Expert series. We’ve gotten great responses whether it’s through this blog, emails or through forums. Since you all enjoy these little segments, we will continue to bring them to you!

If you missed the first 2 interviews you can find them here:

Today, we’ve been lucky enough to interview James ILes. James and I have had various conversations over at Namepros forum and he agreed to answer a few questions in regards to domain names. The guy is cool and knows his stuff. Get ready to take some notes.

Let’s dig in…

1. How did you find out about domaining? Was it something you were looking for to make extra money or something you stumbled upon by accident?

I stumbled across a domain name whilst browsing eBay. It was the domain name for a famous singer from the UK who I happened to like a the time. I decided to buy the name without knowing anything about domain names at all. A few months later, Warner Bros signed the singer and approached me with an offer to buy the domain, which I accepted.

After that, I spent the money from the sale on a lot of 64 domain names from eBay which were terrible domains that I ended up dropping a year later.

2. When looking at a domain name  to purchase, what are the key factors that help you determine whether or not it is worth buying?

I have a number of criteria which I use to determine whether or not I should bid on or buy a domain they include:

  • The TLD. I usually invest in .COM domains only
  • End users. Do any companies use similar domains or TLDs? If there’s an active website on a .NET domain, then I may consider acquiring the matching .COM domain and selling it to the .NET owners.
  • Age. I like older domain names from early 2000s and 1990s.

If I’m interested in a domain name, I’ll also repeat the name to myself a few times or even type it out a few times. If it’s easy for me to say or type, then that’s a plus!

3. What mistakes have you made that you can share with our readers to help them from making the same mistakes.

I’ve made so many mistakes in domain investing, but I’ll mention just a couple here. Buying a misspelled domain name was a mistake (I thought I was backordering, whereas I actually backordered and ended up paying $69 for it).

I must also confess that I fell victim to the Domain Appraisal scam before I knew anything about domain names. I was approached one day by someone offering $35,000 for one of my domains. I ended up paying for an appraisal, and never heard from them again.

4. How many hours a day do you put into your domain business?

I spend an hour or so looking at expiring domains, and usually around the same amount of time researching potential buyers for my own domains. I also spend around 1 or 2 hours writing for and conducting interviews for upcoming blog features.

5. What has been your greatest domain sale to date? Can you disclose the name? If not, can you disclose the overall profit you made on the domain name?

I can’t disclose details of the domain sale publicly, but it was a five figure sale from a domain name that I bought for $69 around 10 months before. It was sold to a fitness startup.

6. What are your thoughts on the new GTLDs?

I have a grand total of three new gTLD domains (one .club, two .online). I prefer to stick to .COM domain names for now, but I may look to buy a few .web names when they’re released.

7. Everyone wants to learn how to sell their domain. What’s your advice for someone who has a good name and wants to sell it? Should they do outbound sales (contact potential buyers) wait for offers to come to them, list them on auction websites such as Godaddy, Flippa etc. What works for you?

I am someone who conducts quite a lot of outbound sales, as I think the best chance of you getting the largest ROI for your domain name is by selling it to an end user. I’ve only used Flippa once to sell a domain, and that was to raise funds for another purchase.

8. If you had to sit with someone completely new to this business, what would be the best piece of advice you could give them?

Don’t buy a domain name until you’ve watched every video on and have read active threads on Both DomainSherpa and NamePros are full of free advice from some of the most successful domainers. I’d also recommend browsing daily to see the latest domain sales. It’ll give you a good idea of what sells and for how much.

9. What are your thoughts on hand registering a domain name? Do you find value with them or would you rather purchase your domain names from the aftermarket?

I don’t hand register domain names. As I stick to .COM domain names (which probably make up around 90% of my domain portfolio), I believe that the best opportunities for making real money from .COM domains is to buy on the aftermarket – NameJet, SnapNames or private acquisitions.

My typical strategy is to flip domain names – acquire and sell immediately – and I don’t believe that this is possible with hand registered domains.

10. Where can the audience find you if they would like to learn more about you?’s blog is probably the best place to find out more about me. I regularly write for (find my profile here) on a number of topics, and often share personal domaining stories there, too. Other than that, my book Domain Investing 101 ( may be a good place.

There ya have it. Another great interview in the books with James ILes.

So you have any questions for James? Would you like to send a quick thanks for him taking the time out to answer these questions? Let him know below!

Don’t forget, more interviews could be found here.

Looking for a domain broker? Maybe we can help. Find out more here.

*Quick Note: We’ve actually purchased James eBook and it is well worth the money. Anyone just starting or who is advanced could learn from the strategies he shares. No, were not making money from giving praise about his ebook. We just highly recommend it.*

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Omar is the CEO & Co-Owner of The Limitless Legacy Network LLC, where his company focuses on buying and selling online properties. He also handles the companies domain acquisition, brokerage and media relations. Stay updated to their blog by joining their free newsletter here

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If you are interested in viewing their domain portfolio, visit their company website here.

19 thoughts on “Interview With The Expert | Volume #3 – Featuring James ILes

  1. Thanks for the interview James and for providing us with some very useful tips and advice. Not too mention how great your Ebook is. I finished reading it and was exposed to awesome methods of reaching out to end users as well as some very useful tools I was not even aware existed!

    Goes to show you, there will always be something to learn in this industry and it will be very important to continue educating yourself.

    – Will

  2. Will and Omar,

    Just wanted to say keep up the great work guys. The site so far is terrific. Even though, I’m pretty much a beginner to the wonderful world of domaining, this blog is pretty helpful and the videos are humorous and original. I really dig the spin and the style you guys put out and the interviews have been informative as well.

    That said, there are a couple of things I would really like more knowledge about and would appreciate seeing on the site. A reference or library page with resources/tools/websites/glossary (possibly including suggestions of books that have been helpful to you guys) would be AWESOME for anyone interested in domaining of all levels, but especially newbies like myself, I envision it as kind of like a quick start guide– everything all in one place. Not sure if you guys are interested in something like this.

    Either way, thanks again for the great content. I look forward to seeing what you guys have in store for the future.


  3. Great article and interview! I’m just getting back into domaining and really appreciate articles that give real advice on how to avoid the early “traps”. I excited to see the industry is still alive and well and hoping some of the new GTLD’s prove to be great opportunities. I’ll be doing the research you mentioned on Namepros and DomainSherpas.

    • Hey Nathan.

      Thanks for stopping by. Glad you liked the article and advice. Let’s see what happens with the GTLD’s!

      We’ve got more interviews lined up, stay tuned.


    • Hey James.

      No no, thank you for sharing your wisdom with all of us! We are soaking up all of the knowledge you’ve dropped on us. Your book was VERY good as well. Picked up several tips from you and also confirmed a lot of things I was doing on my end and wondered if others were doing it. I suggest more people pick up a copy. Hope you can be a part of another segment some time soon!


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