Naming a startup is hard. Very hard. On the one hand, the pragmatic entrepreneur thinks: “I shouldn’t be wasting time on this — for every successful company with a great name, there’s one with a crappy name that did just fine. It doesn’t seem like a name has much influence on the outcome at all. I’m going to get back to writing code.” I sort of agree with this. You shouldn’t obssess about your name. But, you also shouldn’t dismiss it as unimportant. Part of the startup game is to try and remove unnecessary friction to your growth. Sure, you could build a spectacularly successful company despite having a lousy name — but why not stack the odds in your favor?
One more reason why spending calories on picking a great name is important: It’s a one-time cost to get a great name — but the benefit is forever. Conversely, if you short-change this and dismiss it completely, you’re going to incur what I’d call “branding debt”. Not bad at first, and maybe not a big deal for you ever, but every year, as you grow, you’ll have this small voice nagging inside your head “should I change the name of the company…”. It’s going to be annoying. And the longer you wait, the more expensive the decision is, and the less likely you are to do it. Save yourself some of that future pain, and invest early in picking a decent name. You may still get it wrong, but at least you’ll know you tried. 
One last note before we get started: Not all of these are weighted equally. And, remember that these are suggestions not laws. They’re also mutable.
The 17 Mutable Suggestions Of Startup Naming
1. Make sure it’s legal! This should be obvious, but it’s an important step that too many entrepreneurs skip. Before attaching yourself to a name, make sure that someone else doesn’t already have claim to it by way of a trademark. In the U.S., you should take a quick peek at http://uspto.gov. The good news is that if you satisfy some of the other conditions below (domain name, twitter handle, Facebook name), odds are relatively low that someone’s already using the name.
2. Hint At What You Do: You have two paths to go when picking a startup name. You can pick a name that is “synthetic” and made-up (example: Wufoo or Quora) or you can use somthing that is somewhat descriptive of what you do (example: Backupify or KISSmetrics). I lean a bit towards the descriptive side of the spectrum. But, a lot depends on what you’re building. Synthetic names are often great in the long, long-term (easily trademarkable, and you can truly “own” them and infuse them with meaning) — but most of the time, I’m more worried about surviving in the short-term. So, I like simple names that convey a bit of what the company actually does or stands for.
3. Make it easy to remember: How do you know whether a startup name is easy to remember? You don’t know. So, test it. Talk to people. Describe the company. At the end of a 2–10 minute conversation, casually ask them if they remember what the name of the company is. If it didn’t “register” it’s not a failure on their part (and make sure to tell them that), but a failure on your part for not having something that’s memorable enough.
4. Make it unambiguous when spoken: A quick way to test this is to ask friends and family what they think of the name over the phone — and ask them to spell it back to you. If a decent percent of them get it wrong — or are uncertain, you’ve got a problem.
5. Make it unambiguous in Google: Many of the tricks of the trade you’ll use to monitor conversations that mention your company on the web will involve doing some sort of search. If your name is something like “Pumpkin”, you’re going to have a harder time distinguishing when people are talking about the generic term, or when they’re talking about your company. Of course, there are plenty of examples where a startup started with a generic word and went on to be pretty successful (Mint.com jumps to mind). That’s why these are suggestions (not laws) and they’re mutable.
6. Start early in the alphabet. In the pre-Google world, this was done so that you’d show up earlier in a lists of things that are often sorted alphabetically (like when you win an award). In the post-Google world, a similar rationale applies, but what’s more important is the position of links to your website when it shows up in a list of things (like a directory). If possible, you want to be in the first page of a multi-page article that mentions a bunch of companies. The first page of a multi-page directory usually passes more SEO authority to your website than subsequent pages.
7. The “.com” has to be “gettable”. By “gettable”, I mean that it is either not registered yet — or, it is available for purchase at a price you’re willing to pay. Don’t play tricks with the domain name either — like including hyphens. Also, stay away from clever domain names like del.icio.us. The reason is simple: It’s not natural for people to type domains that way. (Note: Even del.icio.us eventually switched to the much easier domain, delicious.com).
8. The twitter handle has to be available. No tricks with numbers and underscores and stuff. You want the most natural, obvious twitter handle that matches your company name. This is not quite as hard as .com domain names — but getting harder every day.
9. The facebook page should be available: To test this, try visiting http://facebook.com/yourname and see if there’s something there. Or, do a search on Facebook and see what you find.
10. Keep it short. Always good advice, but particularly true in the age of Twitter. The more characters in your company name, the more characters in the tweets that people write that mention your company name. 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. Also, number of characters is not the only consideration, 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.
11. 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.
12. 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, this 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).
13. 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 demonstate some humility, but 99% 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. If you’re going to ask the world a favor, save it for the big stuff — not “can you please be sure to spell our company name with a lower-case letter”.
14. Don’t name your company after yourself. Yes, I know it’s tempting because it’s so easy. And, you might even think “hey, customers should know who they’re doing business with”. You might even make an argument like “there have been plenty of successful startups that were named after their founder.” Though that might all be true, on average, this is a losing approach. 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. The other reason is that 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.
15. 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.
16. 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. For example, when I started my first company (I was 24, and didn’t know what branding was), the name I picked violated many of the rules in this list. The company name was “Pyramid Digital Solutions”. But, it had a pretty good story. I started first with the acronym P.D.S. I wanted to name the company after my dad (whose initials are PDS). He’s a tad superstitious and didn’t want me to name the company after him (it’s a long story). And, wanting to prove him wrong I started with the acronym PDS. Then, for the first word, I picked “Pyramid” because I was passionate about strong, architectural software design. We were going to build products that stood the test of time — much like the Pyramids. The other two words (Digital Solutions) were sort fluff words. Summary: It’s OK to be purely scientific in your name selection, but a good story never hurts.
16. 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 is not terrible, but does cause 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.
17. 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. For more on the topic, you might want to check out Guy Kawasaki's article on the topic (makes some similar points, but he's a better writer). Also, hat tip to the "22 Immutable Laws of Branding" whose title was an inspiration for this blog post. More floating around in my head, but I’m a believer in the “release early, release often” mantra. So, what do you think? Any other tips or rules of thumb you use when coming up with startup names?
Oh, and I'm thinking of creating a simple web-based tool that assesses a name (which I think is hard to do via software). What do you think of that idea? What kind of features would you want to see?