However, I'd argue that most people in the business really struggle as they don't understand what makes a good domain name and what's a bad domain name. While I do not work in this field full-time, I can say that I can make a living of it, but it's probably because I don't ask for absurd prices (e.g. randomword247.com domain name for $8000 is just unrealistic and won't happen) and therefore can sell domains easier. 
Where do I start? So I heard about bitcoin and I know it’s all the craze nowadays. Let’s start from there. I’ll hop on Google Trends and type in “bitcoin”. Google Trends basically tracks the popularity of search queries over time, it’s often a goldmine for discovering currently exploding or soon-to-explode topics/terms..etc. So here’s what it looks like:
As you can see just within expired domains they have over two million deleted .com domains. Now, this is obviously overwhelming if you’re trying to look for domains. So, you should use a few filters to make the search process a lot easier. To do that, click on the search filter button. Down here I like to click on the Only With A DMAS Entry because that just filters out sites that are really spammy. For sites that that have been in DMAS ever, it means that the site had to be of some quality.
Now, a lot of times these great domains that have pending delete will get snapped up in a flash. Okay? You want to use the same system that’s 500,000 domains so you can always sort them by whatever you want to do to make sure you’re only looking at quality domains and look at the link profile the same way. Once you find one that you like, you can’t just sit on your computer at Go Daddy and wait for it drop on 6/14 and expect to get it because there’s going to be a lot of other people gunning for that domain. You actually have to use a service like Snap Name.

That’s it for deleted domains which you can just pick up by heading over to your favorite registrar and registering it right away as long as it says, free and green here. If it says registered it’s obviously taken. This is obviously a cheap way to get some great links because let’s say, you know, this site we saw is not bad. It doesn’t have page rank, but that could be just because there was no content on the site. If it has a solid link profile, you can be sure that the page rank will come back and you can pick it up for about $10.
When you are selling a domain name, you don’t want to suffer because of failed transactions or being tricked by defaulters. Safeguard your monetary dealings; the best way to do this is to take the help of a secure domain transfer and escrow service. The escrow system is highly beneficial because a buyer has to deposit money at the trusted source prior to purchase, and the dealing between a buyer and a seller takes place through a secure domain transfer and escrow service. This makes the transaction safer for both parties with the involvement of a neutral third party.
This is similar to house flipping, where a home is purchased and fixed up in order to sell for a fast profit. Unlike house flipping, however, there is essentially nothing to be done with the domain name in order to increase its value. Therefore, the key to a successful domain flip is being in the right place at the right time in order to acquire a valuable domain name before it is given a higher price.

Simply put, domain flipping is the process of acquiring a domain name with a motive of selling it at a higher cost to someone else. This is very similar to flipping houses or cars, the only difference being that you can’t do much to increase the value of the asset by ‘fixing it up’ and then turning it over for a quick buck. Acquiring a valuable domain name before it is tagged with a premium price is the key to a successful domain flip. Raymond Hackney, a domain investor and consultant, successfully flipped a .website domain (his first on a new domain extension) for a decent profit. Read all about it here.
Prospective buyers can contact domain holders directly in cases where the desired domain is no longer available. Most registries openly publish the names and contact data of domain holders. Once this information is gained, buyers can get in touch with domain holders and make them an offer for the name. Sales are also known to occur even when the original domain owner may necessarily have never had any prior commercial ambitions
If your domain name is related to a particular niche, then you may find success by advertising in forums that are related to that niche. Simply placing a link in the signature of your posts can tremendously speed up the selling process. While it may be possible to find prospective webmasters on niche-specific forums, it is generally better to advertise on webmaster forums, where there is a high volume of potential customers.
There is a common misconception that domains expire on their expiration date. If a domain registration is not renewed by its expiration date, the domain simply goes into "expired" status, which means all services are shut off. Typically, we provide a 35-day grace period during which the current holder can still renew it for the standard renewal fee. For more information please review our domain deletion policy.
What about option #4 - Redirect your existing domain to the old domain? I bought an old domain that is 100% relevant to my current domain but currently has with very little content. It did have more content fours years ago. The old domain is 13 years old, pr=3, while my current is 7 months old pr=1 and a decent amount of content. The old domain I purchased was not expired though and I do not know if this makes a difference. What are the pros and cons of option #4? Am I correct to think that option #1 would result in no benefit from the old domain's age value and if so why is it not listed as a con, a MAJOR one. Its hard to believe that a 301 using option 1 would give my existing domain 13 years credit but I'll take it if it does.
The easiest and least time consuming option is to 301 redirect the old domain to your existing site. This tactic obviously works best if both sites are in the same sector and are targeting the same keywords; otherwise, if you have a pet supply site and you buy an old Texas Hold 'Em poker site, a redirect probably might raise some eyebrows among the search engines. If, however, your site is brandnamepets.com and you buy onlinepetsupply.com and 301 redirect the domain over, you're inheriting a lot of topical and appropriate links.
So how do you develop that instinct? NameBio maintains a database of over 500,000 historical domain sales (as of writing this post). They have interesting filtering features by which you can narrow down domains by price range, date sold, keywords and more. Simply sifting through the listings on NameBio long enough will quickly develop your domain appraisal “instinct”.
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