8 more mutable suggestions of startup naming

(Editor’s note: Dharmesh Shah is a serial software entrepreneur and the founder and CTO of HubSpot, which provides marketing software for small businesses. This column originally appeared on his blog.)

What’s in a name? A fair bit, actually, when it comes to the startup world.

Last week, I offered nine suggestions to keep in mind when you’re searching for the right name for your business. This week, I’ve got eight more. Like my previous story, these aren’t laws. They’re also not weighted equally and are mutable.

Keep it short.  That’s always good advice, but it’s particularly apt in the age of Twitter.  The more characters in your company name, the more characters it will consume in the tweets from people that write about you.  And the more characters your company name uses up, the less you can actually say in a tweet.  Generally, try to stay 10 characters or under.  It should be short when spoken as well (that is, have fewer syllables).  The fewer the syllables, the easier it is for people to say.  Great examples of one and two-syllable names:  Dropbox, Mint, FreshBooks, ZenDesk.  I’d shy away from anything that is over 3 syllables.

Don’t leave out vowels or add punctuation.  Just because Flickr was successful does not mean it’s OK for you to drop vowels from your name.  Name your company in whatever way is natural — for humans.  And don’t add punctuation (like an exclamation mark) to your name.  Yes, it’s distinctive and it worked for Yahoo! but there’s no sense spending calories on this.

Try to get your main keyword into the name.  This helps with SEO and signals to potential visitors what they might find on your site.  For example, my site is called OnStartups.com.  Not particularly creative, but you have to admit — it’s clear.  (And, is likely partly responsible for my high rankings in Google for a bunch of startup related words).

Start with an uppercase letter.  If it’s good enough for Google, Amazon and a thousand other really successful companies, it’s good enough for you.  Sure, starting with a lower-case letter is cute and might demonstrate some humility, but 99 percent of the people are going to spell it wrong and you’re going to spend too many cycles worrying about training them — and you’re still going to fail.

Don’t name your company after yourself. When customers hear something like “Dharmesh Shah Enterprises” (granted, your name is probably not as odd as mine), it doesn’t make them immediately think “Wow, that must be an awfully cool/successful/stable company”.  It sounds a bit amateurish right at the get go.  Also, if you name the company after yourself, too many people are going to want to talk to you.  That’s ok when you’re the only person in the company to talk to, but becomes problematic as your startup grows and there are other people trying to sell/support/market.

Don’t use an acronym: These were all the rage at various points in time — but I’m not a big fan.  It’s hard to get emotional about a three-letter acronym.  It’s hard to hug an acronym.  As a corollary to this, try not to have a company name with three words in it, because it’s long enough that people are going to be tempted to reduce it to an acronym.

Have a story.  When someone asks (and they will), so why did you pick X for your name, it’s nice to have something relatively interesting to say.  Names are a part of your personality, and the absence of a personality is rarely a good thing.

Pay attention to character sequences in multi-word names: This one’s a bit subtle.  But, if you have a name that is two words stuck together, then be mindful of what character ends the first word, and what starts the second.  I’d stay away from names where both of those letters are the same.  Example: If your company name is something like BetterReading, it’s sub-optimal (because Better ends with “R” and reading starts with “R”).  Normally, that’s OK, but when you type it out as a URL, people will often see:  betterreading.com — which causes the brain to “pause” for a micro-second because it feels a tad unnatural.  And, I’d be remiss if I didn’t bring up the widely popular example of unfortunate character sequences:  expertsexchange.com.  When capitalized properly, this name is just fine (ExpertsExchange) which is what the site owners intended.  But, it turns out, this can be confused as “ExpertSexChange” (which is not what was intended).  Make sure you think through the combinations properly.

Seek timeless instead of trendy: It seems that every generation of startups has their own “trendy” approach to names.  Examples are the dropping-vowels thing (like Flickr), the breaking up of words (like del.icio.us) or the newly fashionable “.ly” names.  I’d suggest that names that don’t necessarily indicate when you started are a good thing (on the off-chance that your company outlives that particular fad or trend).  Pick a name that is timeliness.  One that people will see 10 years from now and not think “Hey, they’re one of those companies…”.

That’s all I have for now. So, what do you think? Any other tips or rules of thumb you use when coming up with startup names?