First, some humility.  Choosing a business name is HARD.  You are deep inside your business; you know it better than anyone else, and that familiarity robs you of much-needed perspective.  Screwing it up is probably the expected result, if you're being honest.

But if you're gonna screw it up, at least try to make fresh and interesting mistakes. There are already plenty of examples of bad names with big mistakes out there to learn from. So let's take a look at a few, and see if we can't make your next name a little better, or at least, bad in an interesting way.

This article is part of a series in How To Screw Up Your Business. The author has precious little experience in how to truly succeed in business, but ample experience in the opposite, and can be considered a qualified resource.

#1: Picking a name that's impossible to search for

Look, I love Drip, I really do. And when you search for "drip", they are the number one search result.  Good for them! But it didn't always used to be like that.  They had to sink a tremendous amount of marketing energy and dollars to get there.  It's a short, funny, business-appropriate name that added so much extra work onto their plate.  And until you're at the top of the pile, common searches that customers will do to learn more about you or how to use your app will return absolute garbage results, making it more frustrating than it has to be.

A big caveat, obviously: This has actually worked out really well for Drip, as they now completely own a common term in their segment.  For certain common searches, like "drip email", they're the top two spots (as of time of writing).  This is incredibly powerful, since customers looking for general information will get funnelled to you directly.

But it's not all roses.  If you search for "drip campaign", Drip isn't even above the fold. And Drip has had years to work on this. If you're just getting started, strongly consider not picking a name that you're going to have to fight tooth and nail to get any sort of search presence for, especially if you don't have a war chest to fuel that particular fight.

#2: Picking a name that's impossible to spell

You might think it's really clever to name your digital product delivery business "e-sayle-er" (it's like a retailer, but an e-tailer, and we do sales, like an e-sale-er, but with a funky twist!) but just try spelling that to someone you meet IRL.

"Well, it's e, like the letter, than a hyphen, then 'sail', well, with a 'y' and an 'e', no, in the middle, well, I mean, not both.  Look, it's s-a-y-l-e... right.  Then another hyphen, and then 'er'.  Yes, 'e-r'. No, you forgot one of the hyphens, right after the e.  No, the first e!"

Obviously this is a manufactured example, but I have heard (and come up with) some whoppers myself.  The best example I have ever seen was Cuil, a search engine whose pronunciation and spelling had to be explained every time it came up in conversation.  (Incidentally, it's pronounced "cool", just "cool." Yes, you're correct, that's not actually very cool at all.)

Not to mention, accents exist!  The way you say "s" could sound like an "f" or even a "z", if you're talking to a hard-of-hearing Canuck.

You're going to get really tired of that "clever" name the fiftieth time you've had to spell it to a stranger.

#3: Picking a name with a tonal mismatch

Unless your target audience is "everybody", they'll probably have a pretty specific opinion of themselves.  They're professionals, or they're mavericks, or they're fun, or they're serious, etc.  If the name you choose doesn't match how your customers feel about themselves, you're going to have a hard time selling to them.

Say, for example, you're selling accounting software for small businesses.  There are excellent examples of good names for this category, like Freshbooks or Quickbooks. But you probably wouldn't want to pick something like "Full Accounting" or "Fussybooks".  Small business owners don't want to spend all day doing accounting, they want to just get it done and move on.

Similarly, you want to make sure you don't mismatch the stage of business you're targeting.  If you're looking to attract enterprise customers, you need an enterprisey-sounding name.  Would you sign up for "Quik-kat's Security Toolz" to perform security audits on your hundred-million dollar enterprise?

#4: Pigeonholing yourself

It's not strictly important that people be able to immediately and exactly tell what you do from your name.  If you heard the names "Google", "Twitter", "Apple", or "Amazon" today, would you know what they do without being told? No, and it doesn't really matter. They've been able to grow and expand their brands to essentially whatever they want.

What can be a danger, though, is picking a name that pigeonholes you into too-small a market. Imagine if Stripe was called EasySubscribe.  You'd definitely still expect to be able to accept subscription payments through them, and easily, too! But what about one-off purchases? What about in-person payments? You wouldn't even given them a second look.

#5: Picking a name you can't get the .com for

First off, if someone else already has the dot-com for your name, you might be running into trademark issues, which can be a real speedbump when you're just starting to gain momentum. If someone is already operating under that name, pick a different name.

But aside from that obvious hard-and-fast rule, you probably still want to pick a different name even if someone is only parked on the dotcom domain.

Having a dotcom radiates authority, at least in most cases.  For example, .org is great if you're a non-profit, and .io seems to have been reasonably accepted as a "techie" domain name, but .net, .app, .biz and all the others tend to read as second-stringers.

Country-specific TLDs have their own host of issues, too. If you're not actually a resident of that country, you could run into trouble if that country ever decides to change eligibility rules about who can own a domain there. Plus, you run the risk of dissuading people who are not from that country from doing business with you. Yes, you may be able to register something like "" (actually you can't, I checked), but if you're not offering Canadian-specific tax advice, you will probably scare off any non-Canadian customers you might have had.

Besides, people will tend to assume the dotcom anyway.  If someone is trying to remember your site address and you have "" or "", they can go from "prospective customer" to "frustrated prospector" really quickly.

(Oh, and if you go with "", you are going to get customers assuming your business is called "getyourname" not just "yourname".  It is a guarantee.)

Eventually, you are probably going to want to purchase that parked domain, only now that there's a sigificant brand interested in it, the price will have gone up. Do yourself a favour and get a dotcom first.

Photo by Austin Kirk on Unsplash

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