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Startup Tools: Website Domain Names

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By Jason Calacanis

The name of your startup is critically important to its success, and in this email I am going to help you land an amazing name.Think of Google, Yahoo, EBAY, Mahalo, Meetup, Yammer and Mint -- are all six letters or under, generally easy to spell and certainly unique. This is not a coincidence.

Landing a short dotcom domain name in 2010 isn't easy, but it's certainly not impossible. I know this because I was able to buy for $11,000, for $30,000, for $70,000, for $15,000 and for $7,000.

That's not chump change, but given that the average angel round is $500-$1m, investing five to ten dimes is no big deal.

Great entrepreneurs tackle and solve challenging issues like naming their company well, and if you can't name your company well, you're simply not worth investing in.

I know it's harsh statement, but it is true. Better you hear it now while you still have a chance to hit a homerun.

If you go into a VC or angel meeting with a crappy name, they will look at it the same way they look at you unshaven with a stain on your shirt and a deck full of misspellings: that you lack focus and attention to detail.

For potential investors, critical hires and game-changing partners, the last thing you need is to tell them you lack focus.

Now, when someone shows up with a kick-ass domain, company name and logo, the first thing I think is: Dude is baller!

A stunning domain name paired with a world-class logo makes you look like a killer.

The first thing you will hear from people when you say, "Our company is named (or, or" is "how did you get that domain name?" or "how much did you pay for that?"

That is what you want when you're in a meeting asking people to give you money: credibility.

In fact, I'd rather have someone with a mustard stain on his shirt, smelling like a homeless guy, pitch me on over Andersen Cooper in a tight, fitted black t-shirt, pitch me on

No offense Andersen, you're totally dreamy and all, but if your domain name is not easy to spell, I'm not interested.

Lets take a look at the top 100 sites in the United States per Quantcast ( ).

You'll find that 100 of 100 are dotcoms (as you might expect).

In terms of length, the biggest sites in the USA have short ones:

Two letter: 2
Three letter: 8
Four letter: 9
Five letter: 15
Six letter: 11
Seven letter: 18
Eight letter: 9
Nine letter: 8
Ten letter: 4
Eleven: 6
Twelve: 3
Thirteen: 2
Fourteen: 2
Fifteen: 2
Sixteen: 0
Seventeen: 1

In summary: Six characters or less: 45%; Eight or less: 72%; Ten or less: 84%

Great companies have great names (and the associated domain names). It's not a coincidence.

Amazing names share the following basic qualities:
a) Short, less than eight characters
b) Easy to spell
c) Literal (i.e. or evocative (i.e. & Google)
d) Memorable after one exposure (i.e.,,

Good names tend to be:
a) Longer than eight characters
b) Require a question when you say them over the phone: "oh, it didn't come up... oh, it's with an 'e'
c) Sentences or phrases (i.e.,, etc).
d) Hipster misspellings (i.e.,,,, etc)
e) Memorable after two or three exposures

Bad Names tend to be:
a) Long
b) Require more than one explanation over the phone (i.e. "it's, with no spaces, no dashes, the number four and the letter u.")
c) Impossible to remember
d) So hard to remember that Google has a hard time finding them or correcting your spelling

Amazing names take a lot of work, sometimes months--even years--to land. They usually cost $10k to $100k - and even top $1 million on occasion.

Good to great names take weeks to get, and cost a couple of grand generally.

OK names can be bought for $8.95 right now on GoDaddy.

Under no circumstance should you settle for an OK or bad name, except if it's just a placeholder and you're NOT showing it to investors.

It's fine to have a good name when you're in your angel round, but when you're getting to scale as a company you're going to want to spend the money--even if it costs $100,000--to get a killer domain name.

How to get a great name
As a startup you need to learn how to acquire good and great domain names. There are a couple of steps, but here is what I like to do.

1. Brainstorm Words
Get your founders together and open up a bunch of dictionaries and laptops. Nick Denton turned me on to's "reverse dictionary," which lead me to the word It turns out it's an old word for a hobo or wander, and I was shocked when I found out in the Weblogs Inc. days that it was--gasp!--available for $8.95 on GoDaddy!

If I was going to do a travel site today, for example, I would look up all the words around travel.

A ) Do a search for 'travel slang' and 'slang for travel' and 'slang for flight'( ). From that search I found that there is a travel slang website, and from that I browsed how someone just came up with the term 'salmoning' for folks biking the wrong way down a street. Neat! I just bought the domain name one had bought it. Salmoning is a little long, but very memorable and unique. It's also not that hard to spell and it evokes a radical, anti-establishment, individualistic brand--perfect for an adventure travel site. I'd say this is a certainly good, but arguably not great. We would have to MAKE IT great. That's the opportunity with a name like this or twitter--or google for that matter.

B ) Search and other domain resellers for travel domains. I've found some great stuff on these sites, and in fact in their travel category I just found a very fun "" for only $1,895. I can see the logo in my mind already: a funny guy picking up two suitcases. It's easy to spell, it's memorable as hell and it's only six characters. Bingo!

C ) Take all your fancy travel words and try adding suffixes and prefixes. Putting a Get or a Go in front of a word, and an -ist (as in or an -er (as in at the end, can land you a great word.

D ) Search other cultures for interesting sounding words that you can play with. Hawaiian words like "Wiki" and sounds like "oha" have spawned a lot of domains. is another great sound-based innovation.

E) Proper names are always worth considering. There are tons of great internet-era examples including Craigslist, Huffingtonpost and Dell. History is chock full of names like Disney, Levi's, McDonalds, Chanel and yes, even Walmart.

2. Vet your name
Once you have a contender, make sure you have a name that's built to last, and you aren't buying something that looks great at first, but is laden with "baggage." Once I had my travel site I would:

A) Bounce the name off a few friends to check for misspellings and mis-hearings that I might not have noticed.

B) Make sure the name doesn't have an unintended meaning in another language (google is your friend for this), and can be pronounced at least OK by non-English speakers. The Mazada Laputa is a cute little SUV that was named after a floating island in Gulliver's Travels--it also means "the whore" in Spanish.

C) Cool trick: try typing the name into google (of course), but click on the image search tab. Scroll through the photos and get a feeling of how your term is used. This is the zen of naming, try it on some random unused travel URLs and see what I mean, this one ( ) has a really different "vibe" than this( ) doesn't it.

D) Make sure you're not in conflict with some deep pocketed or very established foe. This is general naming/trademark stuff and there's tons of great info online on how to avoid problems, but do a quick search for obvious problems and save time before you get too attached.

3. Find the owner and buy the domain
Most of the great domains out that are owned, but not being used. In this case you need to do one two things: have a broker like Sedo buy the name for you or contact the person yourself.

First off, I'd suggest if you're going to contact the person you don't tell them it is for a huge startup that is going to change the world. Second, I would buy up similar domains. So, if you wanted from me, I would buy (like Jack Johnson did!) and (which he hasn't!).

Then, if you're not already a female, find a women and have them email and/or call and say:

"Hello, my name is Susan and I noticed you're not using the domain name It's a lovely name and I was wondering if you would be willing to part with it. I'd love to use it for my [ INSERT PROJECT HERE ]. If you're interested please email me back!!! Fingers crossed!!!"

Perhaps this sounds sexist, but in my experience most domain squatters are men. I don't know why that is, but I've bought a lot of domain names and not *once* was it a female. Strange, I know.

Additionally, some of these domain squatters take bizarre pleasure in having something you want to own. They string you along for weeks and month, change terms at the last minute and disappear.

In my experience, men are less confrontational and competitive with women then with other men. This difference really comes out when it comes to negotiating a possession of value (like a domain name).

Now, don't use that strategy if you're trying to buy that is owned by a serious domain broker. I'd use it for those dudes who are camping on domains that don't have a ton of value (i.e.

If the owner won't sell the domain be patient, be nice and thank them for their time. Then ask again in three months.

Don't offer equity in your startup unless it's a super premium domain and the person is reasonable. It's just a huge can of worms in my experience.

4. Fake it until you make it
If you can't get the exact dotcom you want, but you think the person might budge for a bigger number, you can always fake it until you make it with an OK to Good domain. For example, Joshua Schachter got away with using the horrible until he could afford the ransom for It's a testament to how great his product was that such a horrible domain worked so well for so long!

Or maybe the name was so horrible it became the dotcom version of the movie "Showgirls": so unusual and strange that you couldn't get it out of your head. I don't advise startups to do this--you are, after all, not Joshua Schachter.

Or Elizabeth Berkley.

Now if you are one of the greatest entrepreneurs in history on the way to being living legend then you can take what I call the "Steve Irwin" approach, where you try to do something literally impossible with both hands tied behind your back. Do this only if you are extremely talented and a thrill-seeking junkie.

In my experience, it's a lot of fun to take a walking disaster domain like and make it a category killer, but don't try this at home, kids, you're not me either.

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5. Non-dotcoms are fine *if*
In this day an age having a non-dotcom is becoming more acceptable. I chose to use for the new Launch Conference and Newsletter for example, and I'm using a .co for another unannounced project. is being used by Naval at AngelList and it's a killer domain in my mind (and I'm not just saying that because they sponsored This Week in Startups--I loved before that!). is super memorable, and my domain shortener is the awesome

Don't use .net or .org however, those kind of suck in my mind. The 'cool' new domains like .ly, .is and .co are hipster unique--that's sort of why they work. Oh yeah, be careful about how you use these .ly domains since, well, certain governments might care how you actually use the domain!

If you do go with a non-dotcom domain you better make sure it's a GREAT word however. is lame, but or are both great. I think you get the idea.

It's going to be a ton of hard work to get really good, and sometimes great, domain names. It will take tons of debate, hours and hours of making lists, and countless emails reaching out to folks to buy a domain.

Branding is hard.

Acquiring great domains is hard.

That's why investors, customers, partners, the press and potential hires pay attention to it.

People judge books by their covers, and investment deals by their domains and logos.

Oh yeah, we didn't discuss making a kick-ass logo... let's save that for next email. :-)

Epilogue: Domain Name Survey
I did a little domain survey on my blog today ( ), and asked my twitter followers to take it.

In it I asked three questions:

1. If you were running a startup about gadgets, and you've raised $250k in seed money, which option below would you choose below?
------------------ for $175,000 for $8.95 for $1,000 for $5,000 for $14,000 for $2,000 for $750

2. Which is the best name?

3. How important is each factor in naming your company?
Having the .com domain
Being able to spell the name easily after hearing it
Being eight characters or under
Being literal (i.e.,
Being unique (i.e. Google, Yahoo, Bing)

The correct answers for these questions are:

1. Gadgets for $175k, since you have $250k in seed money and could easily raise more with a killer domain like that. Additionally, you could finance the domain purchase over five years. Owning would be a once-in-a-lifetime opportunity. The other ones on the list are all solid: OK, good or great, depending on how you develop the brand.

GDGT is short, Engadget is memorable and, .us and .net are all great since they are memorable and short--despite not being a dotcom. You could win with all of them--but would be the easiest to win with.

2. This is a bit of a trick question because all of these domains are great. However, and are best because they are real word names everyone knows and search for. Despite those being greats names (and great companies!), they are worth a small fraction of what is worth. So, it's not always the name that matters!

3. Being able to spell the domain correctly and being short are the most important factors. You can be literal or unique--it doesn't really matter. Having the dotcom is preferable but not essential as we have learned.

~200 survey results can be seen here:

Thanks for reading!

all the best,


PS - ARE YOU STARTING A NEW COMPANY? Know anyone who is in stealth?
If so, please email me right now and tell me all about your product, as I'm in the middle of selecting 40+ companies to present at the LAUNCH Conference on Feb. 23 and 24 in San Francisco. More information here:

PS2 - If you would like to attend the event, please sign-up at and use the code JasonNation for 10% any of the three ticket types (bootstrap startup: $400; standard $1,000; VIP/Backstage $4,000).

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