It is no secret at this point that I love being an entrepreneur, and it’s a profession that I would recommend to virtually anyone. At the first mention of job-related trouble, the de facto advice I’ll dispense is to quit your job: burn the bridge behind you and don’t look back. I’ve given away more copies of The 4-Hour Workweek than I can count.

I am often asked, “what is the hardest part of starting a business?”

Like most things in life, the process of starting a business seems impossibly complex until you actually begin to undertake it – what appears from afar to be a mysterious black art becomes fairly simple and straightforward upon closer examination.

With my companies, I have negotiated distribution deals with Amazon.com, manufactured life-or-death components for 200 mph race cars in China, and managed 1,650+ different SKUs – without any full-time employees or a background in engineering, and all while living in South America for a six month stretch…without a cell phone.

Having said that, I can tell you – without hesitation – that the hardest part of starting a business is naming it. And, thanks to a booming startup market and the shrinking availability of .com domains, it is getting harder every day.

But fear not, my friends – while the proliferation of tech startups has certainly dwindled the supply of available .coms, it has also given birth to a series of fantastic tools and resources for solving this frustrating problem.

Below, we’ll go over some rules of naming, and subsequently I’ll divulge my heretofore secret arsenal that will turn you into a dark wizard in the mysterious and elusive art of startup naming.

Let me start by saying that I am well aware that there are dozens of successful startups that break all of these rules – visual.ly, ustream.tv, awe.sm, tumblr.com, to name a few. While you certainly can be successful with an unconventional domain, I maintain that doing so creates a barrier to adoption that should be avoided when you have the luxury of naming your startup from scratch.

And so, without further ado…

The 5 Rules of Startup Naming

1. It has to be a .com. My knee-jerk reaction to any alternate (.co, .net, etc) domain is that the founders got lazy and gave up looking.
2. Eight characters or less. There are, of course, exceptions to this rule – but by and large, more than eight characters rarely yields a great name.
3. Phonetic. If you have to explain the spelling, you’ve already lost (e.g. “coffeee.com“, like ‘coffee’ but with an extra e at the end).
4. Easy to pronounce. Say it three times fast and see if it becomes a tongue-twister. There’s a trend of taking words and slapping suffixes (-ate, -ly, -ify, etc) on…but it often ends up awkward and difficult to pronounce. Spotify = good. Spotately = not so much.
5. Intuitive. People should be able to extrapolate your domain name from your company name. It should be yourcompanyname.com, with nothing else added – naming your apparel startup ‘Apple,’ with the domain name ‘appleapparel.com,’ requires that you dictate your domain every time you direct someone to your site.

Tools and Resources for Naming Your Startup

Now that the rules are out of the way, let’s move on to my favorite tools and resources.

• Lingzini.com. This is an awesome tool – just enter a bunch of words that are related to your startup, choose from a list of prefixes and suffixes, and Lingzini will smash them together. Best of all, it automatically checks each combination for availability of .com, .net, and .org domains (though I urge you to hold out for a .com and resist the temptation of the latter two).
• Onelook.com’s reverse dictionary. Simply enter a word or concept, and Onelook’s reverse lookup will return a list of related words or phrases. This is broader than a thesaurus, yielding results that are only tangentially relevant – for example, the search “automotive” brings up words such as “gear” and “downshift.” I’d highly recommend going here first to come up with a list of words to try on Lingzini.
• Google Chat. When all else fails, get a group of friends together in a chat and start a brainstorming session. Quantity and shamelessness are the objectives here – make it clear that there are no bad ideas, and just start spitting out names rapid-fire. At the end of the session, copy down all of the names into Excel and divide each name into unique words, prefixes, and suffixes. Plug them all back into Lingzini to check every available combination.
  

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Now, go forth, name your startup, and make your millions – but be sure to pay it forward by sharing this post on Facebook.

Got a secret strategy, rule, or tool for naming a startup? Post it in the comments below and I’ll update this post with the best of the best.