These days as a professional domainer I do very little selling. I don't like to, nor do I need to.
I have come to the conclusion that the longer I hold something the more it is going to be worth. Just look at three-letter .com's, .net's, .org's, .us's, and .biz's. There are zero left "out in the wild" to be registered. (Three letter domains I am talking about here, not three-character domains, though all three-character .com's have been registered as well).
These three-letter domains always go for, well, let's just say much more than the registration fee. regardless of the extension.
As the value of good generic names keeps increasing, there is very little reason to sell your domains names at this stage at the game. Yet, people do. You would do well to learn one thing concerning the domain name market very early:
PATIENCE. If you are eager to spend money then there will be sharks salivating and lining up, happy to take it from you. The point is, that you don't want to spend money just to spend it, you need to make sure the buys you are making are quality buys.
However, if you do come to a time and place that you want to sell your domain name, you need to keep a few things in mind.
If you are going to make a business out of domains and you are going to open your own company, you need to make enough to pay any taxes that may be incurred. This is a big area of debate and I'm not a tax expert, so consult your tax adviser.
You obviously need to make enough to cover the original purchase price, but you may also need to factor in other expenses such as renewal fees, how much PayPal, escrow fees (sedo or other escrow company) are going to take from you when you make the domain sale.
Can your domain names make more money if you wait a bit longer for a different person who may want this more?
Is there a big enough market to where other people would be willing to buy this name so they had an "edge" on the competition?
Or are you selling to a "reseller"? (a person just as yourself who is buying the name to hold and resell later).
Is it really the "right" time to sell your domain, if you wait will the product/service/etc become more widely known or will the domain bring in more traffic?
Do you really even "need" to sell or do you just want to? You may need money for other ventures, but if you don't, then what is the point?
Is it an offer that you just cannot refuse?
I have had offers on domain names that I could not refuse before, it's not common but it happens. I had just registered about 20 .us domain names and shortly thereafter someone got a hold of me and offered $500 off the bat for one of them. Considering that I just registered the domain name, and the mere fact that the .us market has really not picked up, it was probably a good decision to sell. I sold him the domain for $500 total. That sale paid for the purchase of the other 19 .us's and also the renewal fee for them along with some money to spare.
In a case like the above, unless what you just registered is a true gem, there is probably no reason to decline the offer. But before you sell make sure a transaction will even be worth your time. If the same guy came to me and said he would have given me $40 for the domain name (and that would be as high as he would go), then there would have been very little reason for me to sell.
Remember, your time is worth money too. However, if you are a "time" person, then these are the types of sales you need to target and you need to target them over and over again until you reach a healthy base with domain name parking revenue. Once you become a "money" person, these types of things are not worth your time at all in the slightest. Remember, you want to become a money person as soon as possible.
So if you decide to keep your domain names or not which is completely up to you. Just be sure to make a well thought out decision.
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