A couple of almost-random thoughts about domain names (like jimdugan.com):

1. Choose it carefully

Here is my best advice on choosing domain names:

.com is best almost always (as opposed to .net, .info, .org, etc.) . People remember it, it is commercial (so not best for non profits). It’s the default.

Choose the shortest.

Choose the easiest to remember and SPELL. (Write your radio ad. Do you have to spell the domain name? Repeat it? If so, change the domain name.)

Maybe you have some cool foreign word you want to use? OK but it’s likely to be hard for your customers to spell. So it might be a liability in the domain name. Deal with it and don’t say I didn’t warn you. OK, there are exceptions (google, skype, etc.) but they succeed for their own reasons (short, catchy, lots of startup money).

Brainstorm on it and come up with a bunch of alternatives then ask friends. Go for ease of use, not cute or cool.

1b. Do your searching carefully

One odd thing you have to watch out for: There are many places on the internet to “check availability” of a domain name. Some of them are legitimate; some not so much. Some sites appear to capture the domain names being searched and either use them or sell them. How does this work? Let’s say today you search for “somedomain.com” and it’s available. If you grab it then, you’re fine. If you think on it for 24 hours, someone else has grabbed it. They’ll put some ads on it and sit on it for a while, checking to see if there’s traffic potential.

There’s an odd loophole in domain registration that makes this possible: when you register a name, you have a few days to undo the registration and get your money back. They’re taking advantage of this, grabbing a domain for a few days to see if it’s worth anything.

How to know if a site is doing this? Ask around for reputable hosting. I like dreamhost.com and it’s NOT one that I have heard mentioned as doing the above highjinks.

Some quick background basics here: To have a web site, you need at least two things: domain name and hosting. Hosting is the space on a computer where your site lives and is available to the internet 24/7 (we hope). Hosting companies have buildings full of computers (servers), most of them running many different web sites. The domain name on the other hand (jimdugan.com, google.com, etc.) needs to be registered. The company doing this may or may not be the same as the hosting company. Years ago, there was only one registrar: NetworkSolutions.com. That monopoly broke up but NS still does both registration and hosting. Bottom line: if you have a website, be sure you understand the difference between hosting and registration and keep both of them up-to-date.

2. Guard it carefully

Most domain registrations are renewed annually and a good hosting company will automate the process nicely for you, so you hardly have to think about it. But many things get in the way of this:

• We think that “handy reminder” email is some kind of spam
• We’ve changed email and/or snailmail addresses, so don’t get the notices
• We don’t recognize the name of the registrar

In fact, I’ve spent most of today dealing with a situation where all of the above were true. It’s been a nightmare.

My friend Pedro (not his real name) signed up for several years of registration all at once, to save a few bucks. By the time he needed to renew (Jan. 2, 2010) he had:

• completely forgotten that his domain needed to be registered annually
• forgotten any relation to the company that was asking him to renew
• moved twice, changed banks and credit cards
• ignored or deleted the emails asking him to renew, assuming they were spam
• And when his domain went down due to registration not being renewed, the only email address that the registrar had on record failed to work.

So he was in deep water. Luckily, after several calls to the registrar, a solution: fill out a form and send it with a scan of a government issued photo ID to this address. Wait three days.

We’ll see.

3. Make sure you actually own it.

One other thing to be careful about is companies that register a domain but keep your name off the registration. This is less common these days but it used to be the norm for some outfits. I lost two domain names for just this reason. The company that I asked to register the names went out of business, with their email address as the only contact name attached to the domain.

4. Can Search Engines Read the Domain Name?

Yes, no, maybe, probably. They’re doing a pretty good job but they can’t do much to parse odd words. Google probably doesn’t know whether jimdugan.com is about someone named “Jim Dugan” or “Ji Mdugan” but they would if it was jim-dugan.com. Likewise mainekayaking.com should probably be hyphenated if Google is your main concern. But personally, I’m not crazy about hyphenating a domain name. It always seems awkward to say “JimHyphenDuganDotCom.” Ick.

Your domain name is your brand, your address, the way for people to find you and find out everything they need to know about you. So make sure it’s not a struggle. Make it fun and memorable but this above all: make it easy.