In summary, everything.
When we were coming up with names of our first child, one of my main criteria was that there was absolutely no possibility of the name being used to as a joke or a tease. This rule made it easy to rule out some of the obviously bad choices (such as Pilot Inspektor and Zelda) but it still didn’t make picking a name easier.
As Guy talks about in his book, coming up with an original name for your web site makes all the difference in the world. Coming up with something original is tough and making it work as a web site name is next to impossible. Usually the rule is keep is simple, but tell that to the “Go Tahoe” folks at www.gotahoe.com.
There is absolutely nothing worse then coming up with the prefect name that not only fits your business plan and is really, really, really cool only to find out someone beat you there first. Even worse, is to find out they are not doing anything with the site but are willing to sell it to you for only 10k! No problem if you got some cash to get things started, but when you are on a shoe string budget, it really hurts.
Nevertheless, thanks to my amazing wife and several friends, we have a couple of great ideas to chose from. Now all we have to do is pick one.