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Challenges of Choosing a Domain Name for Your Startup


Picking a company name for your startup can be hard — but choosing a domain name for your startup can be even harder. What should you do when the .com domain for your dream name isn’t available? Should you entirely rethink your branding strategy to get the “perfect” .com address? Should you settle for a second-best .com option? Or should you go for a newer, hipper top-level domain like .io or .me?


Let’s take a look at how six US-based startups have handled three distinct challenges when choosing a domain name.


1. Domain Name Speculation


California startup Purple takes the gas station to you. Drivers in Los Angeles, San Diego, Seattle, and parts of Orange County can request a fill-up on-demand — while they’re at work, at the movies, or even at a backyard barbecue. While some modern motorists are breezing past the pump in Nissan Leafs, Teslas, and other sleek electric cars, Purple lets owners of more ‘traditional’ cars also avoid the hassles of fuelling up.


For a startup named Purple, it would make sense to try to acquire the domain name But it turns out that is already held by a ‘domainer’ — a slang term for someone who speculates in domain names, typically targeting generic words that can get organic traffic just by virtue of their simplicity. “Purple” is the perfect example of a common word that can generate organic traffic with no effort; according to’s FAQ, they receive about 15,000 views per day.


While it may seem that serves no purpose, its unknown proprietor(s) feel otherwise. Under their site’s FAQ, they state in no uncertain terms that the site IS used and is NOT for sale: is not for sale

We do use We understand that those who are not technically inclined nor in the know may not see that. That’s ok. We don’t think any less of those who don’t know our personal business.


The takeaway: I suppose I’m “not technically inclined nor in the know.”


The Purple startup handled the unavailability of (which has been held since 1994 by its current owners) by instead opting for the domain name This domain name is actually more descriptive than “purple” alone. And while the Purple startup doesn’t rank on the first page of Google results for the keyword “purple,” they do claim the top three spots on Google for the keyword “purple app”:


Google Search Results for "purple app"


Let’s look next at the case of Byword. Launched in 2012, Byword is a minimalist text editor for Mac and iOS that “makes writing more enjoyable with Markdown.” If you’ve never written in Markdown, you should seriously consider it. Markdown makes it crazy easy to focus on your text in a clean writing environment and then export your work to HTML, PDF, or even DOCx or ePub formats.


As you’ve probably guessed, was not available to the makers of the Byword text editing software. In fact, the domain “” is currently powered by UK-based Sedo’s commercial domain parking services. As per Sedo’s company website, they’ll help you “earn money with your unused domains and sell them even quicker.” In practice, this means that is a spammy page with five unhelpful “related links.”


Good SEO and a well-built site let Byword easily outrank their spammy imposter in Google search results. 7/10 of the first-page results on Google for the keyword “byword” are either links to an official Byword page or to a positive review of the Byword app.


There’s no need to panic if your startup’s name is currently occupied by a domain speculator in the .com realm. As we’ve seen with Purple and Byword, if your ideal .com domain is subject to domain name speculation there are two simple steps you can take:

  1. Try adding a descriptor to your name.
    • Purple —>
    • Byword —>
  2. Focus on SEO and ranking first on Google, not on getting the “perfect” domain name.
    • It’s easy to outrank spammy sites. Thoughtful keyword optimization and some quality content are all it takes for a legitimate company to rank first for their own name.



2. New Generic Top-level Domains


New generic top-level domains present new branding options for startups. While .io and .me have been especially popular lately, other top-level domains including .tech, .style, .chat, .design, and many others allow startups not only to find an available home on the web, but also to find a top-level domain that is more tailored to their niche than the generic .com.


Let’s look at the case of Bro, a social app for men that launched in 2015. It turns out that is home to the global company called Breault Research Organization (BRO). There’s no chance that people looking for a gay dating app will be confused by a multinational optics engineering company — but at the same time, it’s clear that the Bro app wasn’t going to be taking away an established multinational corporation’s domain.


Bro’s domain name is And the .dating top-level domain gives us additional information about what Bro is all about. In fact, I would argue that is a far better domain name for the Bro app than either or would be.


Drift Away Coffee offers a second example of a startup that has harnessed a new top-level domain to great effect. Drift Away delivers coffee straight to your door as a subscription service. Their goal is to “upgrade your morning routine” by introducing Americans to a diverse range of brews that most people have never even considered. They get you started with a tasting kit that lets you sample their four “taste profiles” (Fruity, Classic, Balanced, and Bold), and from there on out it’s a journey of discovery. Actually, after writing about Drift Away Coffee I really want try out their service! [The Ethiopia Shoye Sidama sounds especially appealing with its Tasting Notes: Peach, Honey Floral.]


While Drift Away Coffee’s original domain name — — wasn’t bad, it was definitely not as descriptive as their new domain name — The .coffee top-level domain was introduced by ICANN on 28 December 2013, and in April 2014 Drift Away Coffee migrated their site to the new .coffee top-level domain.


When choosing a memorable domain name for your startup, you’re limited in the number of words and characters you can effectively work with. Potential customers are much more likely to recall three words — “drift away coffee” — than they are to remember a long string of words such as “personalized coffee subscription service .com.” And with new top-level domains not only is it possible to find shorter names, it’s also possible to make every character of your domain name count. We’ve finally reached an age where we’re realizing that .com is terribly generic, and doesn’t actually describe the purpose or function of most websites.


The most common holdup when it comes to choosing a new top-level domain name is concerns about SEO. Will Google favor over Will .florist or .flowers help a budding flower shop grow their web presence?


While we don’t have definitive answers from Google, it seems safe to say that a new top-level domain will not harm your standing on the web. While moving from to may not drive more traffic to your site, if you’re building a new business (or just a new site) from scratch, it’s worth considering the wide range of new top-level domain options.


Consider these two questions when choosing a top-level domain for your startup:

  1. Is there a descriptive top-level domain for your particular industry or niche?
    • Dating, healthcare, insurance, finance, photography, coffee, and even pizza top-level domains are now available. If you can choose a meaningful word in place of the generic .com, then go for it.
  2. Who is your target audience?
    • Millennials and youth may be more receptive to new top-level domains like .io or .me. People from older generations may find new top-level domains like .io — that hold no specific meaning for them — confusing (for now), although domains like .healthcare and .bank may add greater clarity.



3. Dictionary Words vs. Invented Names

Wooden cubes with letters of the alphabet.

Some startups make up names such as Uber, Zenefits, Expensify, and Zulily. They can’t be found in the dictionary (at least not yet), but they’re short and sweet. Other startups join together two dictionary words to derive names such as LendingHome, ZenDesk, PostMates, and CloudFlare. Finally, some startups choose names straight out of the book, using just one dictionary word such as Slack, Stripe, Pocket, or Buffer.


What are the pros and cons of choosing a domain name — and a brand name — for your startup that’s not built of dictionary words? Is Webster’s actually useful for startups?


Domain names, as well as registered company names, should be (1) unique, (2) memorable, and (3) searchable. As we saw in our very first example, Purple has a memorable name, but it is neither unique nor is it especially searchable — a Google search for “purple” ranks results related to the color purple higher than results related to the on-demand startup.


Let’s take a look at two startups that have taken opposite approaches to naming — one employing a common dictionary word and another making up a name entirely from scratch — and see how they have taken advantage of their particular strategy on the web.


Simple is “The way banking should be: smart, mobile, Simple.” It’s a bank without physical branches, but with free cash withdrawals at many different ATMs throughout the US (you can easily find a local ATM with the app). While big-name banks like Wells Fargo offer apps with services like mobile check deposit, Simple offers a cleaner, more refined app with fewer bugs. Their website is modern and elegant. Everything is made simple — your bank account number is easily available to copy/paste; direct deposit forms can be generated in a few clicks, then handed directly to your accounting department.


Simple stresses the simplicity of their service through and through. And nothing’s simpler than an everyday dictionary name. It’s easy to remember (and hard to forget), it’s descriptive, and most importantly it describes exactly what we all want our banking interactions to be like.


A search for “simple” ranks this fintech startup first in Google results, meaning they’ve proven themselves one step above Merriam-Webster as an authority on this term.


Now let’s take a look at another startup that took a completely different approach to choosing a name. Quora, founded in 2009, is a completely made-up word for the site that boasts “the best answer to any question.” Though only six years old, Quora is probably the web’s most well-known question and answer website, and received a $900 million valuation in 2014.


Naturally, I took to Quora to discover the origins of the name. In answer to the question “Why is Quora called Quora?” one of Quora’s founders, Charlie Cheever, says the following:


We [Charlie Cheever and Adam D’Angelo] both independently came up with pretty similar criteria for what we wanted:

  • Something that probably was two syllables long
  • Ideally something you could spell after hearing it
  • A word that wasn’t commonly used by anything else, so you could search for it easily and not get false positives
  • Starts with an unusual letter
  • Ideally something with double Os in it for good luck (Yahoo, Google, Facebook)
  • Something that made sense for what we were working on

. . .

We’ve been really happy with Quora.  Sometimes people have trouble pronouncing the name or spelling the name when they hear it, but overall, it is short and pretty easy to remember and spell and evokes a lot of the feeling that we wanted.


This is solid advice. Note that one of Cheever’s and D’Angelo’s criteria for a name was that it shouldn’t be commonly used by anything else, so when you search you only find their service. In fact, a Google search for “quora” proves that ALL links on the first three pages of results refer to the Quora Q&A service. (At the other extreme, Purple doesn’t even make the top three pages for their own name.)


Rich Barton, whom Cheever mentions in his response above, also points out that Quora “starts with Q and ends with A (question and answer).” According to Barton, “Quora is a killer brand name.” And a great brand name and a great domain name can be nearly the same thing, especially when your startup IS a web service.


Here’s a comparison of the pros and cons of going with an invented name versus a dictionary name for your brand name and domain name:


Inventing a Name Using a Dictionary Name
  • Domain names are more likely to be available.
  • You can be reasonably certain that your name is unique (especially if you do the necessary research).
  • You’re free to invent anything that has the tone and feel that you’re aiming for.
  • Dictionary words are already known, and therefore easy to remember.
  • You can potentially capitalize on organic traffic just because of salience (how common the word is in the language).
  • Dictionary words have known secondary and often tertiary (or more) meanings that can be used to your advantage in branding and marketing.
  • Customers likely won’t get what your startup does just by hearing the name for the first time.
  • Your name may be difficult to remember (so invent it carefully!)
  • If you’re not careful, people might have trouble spelling your name and finding you on Google or the app store.
  • It’s not new. It’s not innovative.
  • Everyone has access to a dictionary, so your name is less likely to be unique.
  • Non-primary connotations of words can sometimes backfire if you’re not careful.



To come up with a killer domain name, consider the following:

  1. Do any other services/brands/companies use this name?
    • Google the names you’re thinking of. Do you find any results for the word? If not, then the web’s wide open for you.
  2. Is it easy to remember?
    • Cheever and D’Angelo wanted a word with two syllables that could be spelled after hearing it.
  3. Does it make sense?
    • Even if it’s not a ‘real’ world, does it evoke the right feeling? What’s the tone of the word? Does it contain any hints or ‘real’ words lying behind it?




Choosing a domain name for your startup can be a stressful process, and the availability of domain names can be a limiting factor when choosing your startup’s brand name and marketing strategy. We’ve identified three particular challenges for startups when choosing a domain name: domain name speculation/ parked domains, new generic top-level domains, and the struggle between dictionary words and unique inventions.


The examples of Purple, Byword, Bro, Drift Away Coffee, Simple, and Quora can help us see how to overcome these domain name challenges. Always keep in mind that ultimately the quality of your site, your SEO strategy, and word of mouth marketing do mean more than that elusive “perfect” domain name address. Dropbox started out at before eventually acquiring, and their rise certainly wasn’t stalled by this initial inconvenience.


That said, choosing a domain name is no trivial matter. It takes a lot of research and creative thinking to come up with a truly killer name.


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