A conversation kicked up in the entrepreneur section of Reddit a week or so ago where a business owner was fielding ideas on a potential domain he was considering purchasing. Let’s say it was insureatlanta.com. Like most business owners, his hopes were instantly dashed when he went to his domain registrar only to find his dream domain had already been registered. So naturally, he wanted to know if he should just register one of the other recommended options, pop in a hyphen or call up his cousin Guido to take a wrench to the domain owner’s knees. I piped in to say none of the above, and thought thousands of business owners were probably caught in this same no-win situation so why not flesh out the pitfalls of the domain name choice and ultimately how to identify the right one.

The domain name is a very critical decision for every business owner. It follows you for the life of your business on the web. Most people put about ten minutes worth of thought into the decision, and normally don’t consult any knowledgeable resources before staking their claim on this slice of virtual real estate.

Stay Away From Hyphens – Unless your brand already incorporates hyphens (a la Chick-Fil-A), don’t even think about. Years ago, hyphens became in vogue as Google and Yahoo skewed their search results to boost the ranking of websites with keywords embedded in the domain name higher than comparable domains without them. That advantage was ultimately short lived and anyone who tied their horse to that short-sighted strategy are now carrying around a disjointed domain name. Name me five websites you visit on a regular basis that have a hyphen in the domain name. Anyone? Ok, can you name me one? The same will go for your potential customers. When you tell them to go to insure-atlanta.com, they are going to naturally forget the hyphen and skirt right on over to insureatlanta.com. Bam, you just sent your competition a customer. You are a benevolent soul.

Target a .com or a .net Domain – So you’ve plugged your perfect domain name into Godaddy only to find out its already been registered. The friendly bot tries to sell you on an alternate domain extensions like .co or .info. Steer clear of any domains that don’t end in .com or .net (.org is fine and often preferable if you are a non-profit organization). .co was all the rage a couple years ago. Godaddy used their Super Bowl ad millions to tout the new extensions and even Overstock.com temporarily changed their name to O.co (notice I said temporarily). The bud fell off that rose very quickly, and it shows you the dangers of being a first mover in one of these off-the-wall domain extensions. There are exceptions to the rule. The .me extension seems to have found a kindred spirit in the app development community, and I see .io popping up regularly on the Y-combinator domains (ex: robinhood.io). There are a proliferation of extensions set for release in the coming year (.clothing, .photography, .web, .apple) which has the potential to change the domain landscape forever, transitioning it into a more branded approach. I just wouldn’t want to be the pioneer in this space. By choosing a .com or a .net, you are picking an extension that people know and feel comfortable doing business with. If you saw insureatlanta.com sitting side-by-side in the search results with insureatlanta.cc, which one are you going to click on?

The Dinner Party Test – If you want to encapsulate all of these maxims into one easy rule of thumb it is the dinner party test. Say you attend a dinner party this Saturday night, and you are discussing your business with a new acquaintance. By sheer luck, he just happens to be in the market for your product. Usually you have a slew of business cards on you, but they didn’t make their way into your wallet this evening. You tell him to checkout your website. Is your website memorable enough that he’s going to remember it the next morning? Say you told him to go to insureatlanta.co. He’s most likely going to end up typing insureatlanta.com into his browser. Say you got clever and try to switch it up by registering atlantainsure.com. Again that sounds off to your potential customer, and his brain is naturally going to try to flip it around so that it flows like he think it should — fingers typing insureatlanta.com.

Well this is all nice and good and all, but my dream domain has still been registered. What now?

Explore Who Owns the Domain – Just because the domain is registered, doesn’t mean it is lost to you. What is the status of the domain? Is it sitting on a parked page? If there isn’t an active business residing on the site, you need to contact the domain owner to see if they are interested in selling it. Fair or not, there is an entire industry called domaining built around registering domains to sell at a later date for hopefully more than what they paid for it. Domains are virtual real estate, and these enterprising individuals are the land barons of the Internet. It can be a very lucrative trade if you know what you’re doing. Often there will be a link on the parked page allowing you to inquire about the sale of the domain. How to negotiate a domain purchase is a pretty extensive topic in and of itself so I’ll save that morsel for a future article.

Is the Domain Set to Expire? – I seem to have a brilliant business idea about once a day. I think it just goes along with the territory of being an entrepreneur. The problem is most of those ideas show themselves to be turds wrapped in gold foil after I’ve started really turning them around in my head. So lots of domains that started out with the best of intentions will fall back into the domain pool once the owner decides that business was fool hardy, and allows the domain to subsequently expire. To check the expiration date of a domain, simple go to Godaddy Whois and type in the domain that you are targeting. It will bring up all sorts of handy information regarding when the domain was originally registered, when its expiration date is and the contact information of the owner. Sometimes this last bit will be shrouded in a bit of secrecy as the owner has used a proxy service to shield their details from prying eyes. Domain Tools has a helpful feature where you can register for a free account, and it track the status of up to 100 domains. If that one-in-a-million domain is set to expire, you’ll get an email letting you know.

Take a Spin on the Aftermarket – A lot of the domain registrars have a marketplace where domain holders can sell their existing domains. Sedo and Godaddy are two of the biggest in this space. You can search their inventory for available domains for sale based on your keywords, domain extensions, traffic and all sorts of helpful delineators. If it is a high demand domain, expect there to be a hefty price tag sitting along side it. Many listings will allow you to make an offer to the domain holder so feel free to throw something out there to see if he’ll bite. I wouldn’t start with your best offer though as he’s likely to counter offer instead of just accepting the first thing to come across his plate.

Search Domain Auctions for Expiring Domains – This is one of the spaces that I feel has the most potential, but isn’t for someone operating on a tight time frame. Domains drop everyday. The problem is, just because a domain is dropping doesn’t mean you will automatically get it. Most large registrars use a clearing house for their expiring domains (Godaddy, NameJet and Snapnames). Before a domain gets dropped back into the public domain, people are allowed to bid on them eBay-style to snap them up before they ever become available for public consumption. I’d say 95+% of these go ignored for good reason (you really should see some of the crap people register), but there are always hidden gems amongst the rubble.

Great domains take on many forms. Maybe its a nice keyword combination that perfectly fits your business. Often though, you are benefiting from the work of others. Most businesses start on the web at ground zero with no backlinks, no authority — just a random domain fighting for relevance in the vastness of cyberspace. What if I told you that you could jump ahead two or three years along with the PR and promotion that goes along with it? A lot of these expiring domains have that and that link juice and authority will carry over to the new domain holder. You do need to view it with a discerning eye to ensure that the domain’s backlink profile is organic, and that the past owner didn’t spam it into oblivion. Majestic SEO is a good tool for doing such research. If the domain makes sense for your brand, registering an expiring domain can be a savvy way to catapult yourself ahead of your competition.

One huge caveat that must be mentioned here is to check the trademark status of any domain you are registering at auction. You don’t want to drop a couple thousand dollars on the perfect domain only to find out the trademark holder’s legal team is now coming after you. These are headaches you don’t need. That is the perfect segue into…

Is Someone Squatting on Your Trademark? – Few businesses will fall into this category, but if you do its essential that you know your rights. If someone is making money off your registered trademark, its time to fight back. You can find out who the domain owner is by doing a whois search. I use Godaddy, but there are a ton of these services out there. Type in the domain name, and usually all the contact information will come up. Sometimes, this information will be shielded by a privacy service, but there should always be a pass through email address which will be routed to the actual domain holder. Also in these situations, denote the name servers as that will tell you who hosts the domain in case you need to funnel a contact email through their webhosting company.

Your best course of action is to have your lawyer script a letter informing the owner of the trademark infringement and threatening legal action if they don’t relinquish the domain immediately. Cybersquatting penalties can run up to $100,000 plus attorney’s fees per offense so its not an empty threat you are sending. If the domain holder ignores you or tells you to f$%k off, look to file a UDRP (Uniform Dispute Resolution Process) against the owner. You’ll be required to show that the domain name was registered in bad faith with an intent on profiting on your trademark. The domain must be identical or be similar enough to cause confusion by potential customers. This normally costs $1200 to $1500 whereas filing legal action can start at $5000.

While it really rubs me the wrong way in trademark disputes, you could pay the domain holder for the domain if the asking price was below that $1200 threshold (amount needed to file the UDRP). I don’t think you should reward cybersquatters for bad behavior, but it is a viable option if cash is an issue.

As you can tell, this topic is very complex and there are lots of missteps you can take when choosing a domain name. Take the time to properly research your options. We’ve helped companies identify their best domain fit in the past. It can take some time as well as sifting through an array of options, but we’ve always settled on an interesting option that the company ultimately embraced. With a little work, you too can have virtual real estate that is memorable, and you can feel comfortable building on that bedrock for your future success on and off the web.