Illustration by Matt Davidson.

When I first branded my consulting business “Jailbreak Media”, I didn’t think much of the fact that there was another Jailbreak Media out there. I owned the URL jailbreak-media.com and mapped it to WordPress; a Dallas-based marketer owned jailbreakmedia.com without the hyphen, which led to a site under construction. Barely a month after I registered the name, however, he contacted me. Turned out he was a consultant too. Unsurprisingly, he—and his attorney—asked that I stop using Jailbreak Media to avoid confusing our identities.

What to do?

Where it got tricky is that he had owned his URL for a longer period and filed for a trademark, but I had snagged the Twitter handles, both @jailbreakmedia and @jailbreak_media, and cranked out a handful of blogs as Jailbreak Media, which pulled up my company name before his in a Google search. Plus I had filed with the city of San Francisco and had rights to the name under California law. No doubt lawyers could have had fun sorting that one out for years.

In the end we negotiated a settlement. He paid me for two months of operational expenses; in exchange I gave him my URL, released my Twitter names, and renamed my business BCJstudios. Had one of us become greedy or unreasonable, the dispute would be dragging on to this day.

Advice to small business owners: To avoid colliding into your digital doppelgänger, take the following precautions.

1) If you don’t yet have a domain name for your business and someone already owns the .com for the one you want, don’t settle for the .net or .co, or some such. Chalk it up and find another name. You might not think it matters now, but it will down the line. LinkedIn, for examples, requires a .com in order to build a company page; WordPress allows subdomains only for URLs that end in .com, .org or .net. Finding an available .com can get frustrating, but if it takes a thousand tries, I’ll bet the last name you come up will be more original than the first.

2) When you settle on a domain name for your business, don’t just buy the .com. Buy the .net and .org too, or better yet buy every URL ending you can including .co, .info, .me, .mobi, .us, .biz, and steer them all to the same site. Think of the board game Monopoly. Owning more URL endings will dissuade others from pursuing it, and at the same time boost your rankings in search engines. If someone buys a different URL ending of your domain name and uses it to sell a line of adult toys—which actually happened to a friend of mine—you’ll wish you had taken the extra step.

3) Make sure the Twitter handle is available. If you plan to use social media to promote your business, you had better be able to tweet from it, or at least make sure no one else is tweeting from it. At one point I was set to change my FBN (fictitious business name) to Black Wave Studio, but after discovering that I couldn’t get anywhere close to obtaining the Twitter name (@BlackWaveStudio, @BWStudio, @BW_Studio, and @BWS were all taken), I stayed away. Facebook and LinkedIn will allow multiple individuals to use the same business name, but not Twitter.

4) Take a comprehensive approach to your business name in the real world. Whether your business is online or at home, part-time or full-time, you should register it at City Hall, run a notice in a local publication, and set up a DBA account (doing business as) with your bank. And if you really want to lawsuit-proof yourself, file a federal trademark. Doing so will solidify ownership of your business name and give you legal ammo against anyone who tries to use it, especially to sell a similar good or service.

5) If you ever try a sell a domain name, know that the greatest value is attached to names that are one-word and 5-6 letters or less. Slots.com, for example, sold for $5.5 million while dating.com netted $1.75 million. But, according to an online calculation, jailbreak-media.com—at two words, 14 letters plus a hyphen—is worth a paltry $48. Once someone has a vested interest in my name, however, the value changes accordingly. So if you find a potential buyer, let him or her name a price first. If it’s more than you expected, great. If it’s less, you can haggle. In the end a domain name is like digital real estate: It’s worth only what someone is willing to pay.

To keep up with domain news and discussion, visit TheDomains. Or if you want a good site to monitor auctions, try DomainTools.

Brian C. Jarvis is a freelance consultant in San Francisco.