Our default advice is that buying domains doesn't work. The owner either wants a ridiculous price, or doesn't want to sell, or doesn't answer your emails. There are also plenty of good names still untaken. We can often find one in a few minutes using instantdomainsearch.
Net marketing guru John Reese has a tale of how he sold his first domain for $1,000. After the paperwork was signed, the domain broker let him in on a secret. He was actually buying the domain on behalf of a VC firm for $1 million. =)
The trick would be (if it still works) to always use a no-name broker or middleman to get the lowest price... but I'm no expert either.
A problem is of course giving away the idea, but often one can probably formulate it general enough to not do much harm.
I went for it and I'm really glad I did. Would I do it for $3K? Not sure. $4K? I don't want to think about it.
On the other hand it seems inevitable that in the long run people will get used to other TLDs, because not every valid business will be able to aquire a good .com-name.
.tv is different enough from .org/.com to be memorable, and can be quite descriptive about what you are offering.
Closer to home, I imagine this was the strategy employed by Loopt and scribd too.
Then again, if the exist strategy is getting bought by Google or Yahoo, perhaps the name doesn't matter much - it can be changed after the acquisition anyway (ie scripts.google.com).
I just went through this myself. I started negotiating with the squatter and I came to find out that we went to the same school and we travel in the same circles. Even still we were not able to agree on the price so I walked away.
Last week I finally had a new inspiration for the name. It's just one character longer than the perfect name. I was able to buy .com .org and .net with this minor variation from a registrar (not a squatter)!
Keep thinking!
Which raises the question, would you ever buy a domain name (for that kind of price)? Something in me doesn't want to do it, but then again it is hard to find good names that aren't taken. 4500$ is too much for me at this stage of the project, but in principle?
Here's how I would go about negotiating the price:
Subject: Interested in buying a domain name
Date: 2007-04-28
To: squatter1; squatter2; squatter3; ... ; squatter50
I am thinking about purchasing one of the following
domains. According to the WHOIS information, you are the
owner of one or more of them. If you are interested in
selling, please reply back with domain name and the price
you want for it. In order to give everybody enough time to
respond, I will wait a few days collect the responses I get
before I make a decision. I promise I will not disclose
your offer to anybody.
Thank you!
domain1.com - squatter1
domain2.com - squatter2
...
domain50.com - squatter50
Subject: RE: Interested in buying a domain name
Date: 2007-05-10
To: squatter
Thanks for your reply. I cannot afford the price you gave
me. If you still are interested in selling, please reply
back with a smaller price. Thanks again!
Subject: RE: Interested in buying a domain name
Date: 2007-05-25
From: me
To: squatter
Thanks for your numerous replies. I guess my expectations
are unrealistic because I didn't want to pay more than $100
for this project. I am not interested in the other
variations (.net, .org, etc.) you offered me. Please let me
know if you will accept $100 for just .com.
Subject: RE: Interested in buying a domain name
Date: 2007-05-30
From: me
To: squatter
Sorry, $ is too much for me. I will pay $200 if you throw
in the other variations too. I want to finish this up soon
so please reply back with the payment/escrow information.
buy a thesaurus instead.
I'm building the web 2.0 version of this company now and I am starting with a memorable domain that has over 200,000 backlinks already built-in.
If you are a web business, your domain name is your most important asset.
Can you really count on people manually typing in familiar urls today? Even organic search results are not as crucial as they once were.
Was it a bad deal for 'freedrive.com'? Depends on the specifics of the situation and how the company leverages their name recognition.
I would never get a domain 15 characters long
I actually got a great one today :)