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[Crossposted from Medium

When I was writing my book, the first draft was the easiest. Each blank page really was a carte blanche; there were no precedents and no limits.

The fifth draft was the hardest. A cutting draft, only I was having trouble making cuts. I could no longer distinguish between the sentences and scenes that had value and those that were merely sentimental. I felt like one of Borges’ cartographers; I could only hope the real landscape would eventually tear away the weaker parts of my map.

I experienced that fifth draft feeling again last week. A month ago, it had been decided that our app would be getting a new name to match its new platform (iOS) and audience (enterprises using Exchange).

Initially, I’d balked at this decision. I’d liked the old name, Gander. (I’m a sucker for homographs, I guess.)

I warmed up to it pretty quickly, though. Partially because it made a lot of sense from a morale and identity standpoint, and partially because, well, coming up with new names is fun!

And it is; it is fun. First-draft anything-goes limitless fun.

Followed by second draft cut-n-cull, still kinda fun but also kinda anxiety-inducing, because what if you cut the wrong ones?

Followed by third draft constrained brainstorming, because after a night’s sleep the ones you’ve culled seem kinda terrible, to be honest.

Followed by fourth draft cut-n-cull, now hair yankingly-frustrating because everything sucks. Everything! There’s a spectrum of snore-inducing to oh-how-post-modern-of-you, and all of your names occupy one end or the other.

Followed by a fifth draft of reasoned-turned-feverish constrained brainstorming, just one more time, just in case you happen to create some passable cubic zirconia, in the form of compact verbal metaphors. Which, hallelujah, you do.

You give it a day, and yep. You might actually wear this.*

Not all of your team agrees. There is a suggestion that the name ought to be descriptive, immediately identifiable as an email app. Something with “mail” or “box.”

A name with “box” is added to the pile of cubic zirconia. Now it is time to test.

Testing is nothing like writing a novel; testing is like writing a math formula, and then applying it to a dataset. The formula has two parts, one quantitative and one qualitative.

The quantitative test consists of:

· Launchrock landing pages that have different titles and tag lines, but the same copy, images, and layouts.

· Google adwords campaigns tied to each landing page. The ads have different titles, same copy, same keywords, and different urls (obviously).

· To assess, we tally the number of impressions, click-throughs, and sign-ups.

The qualitative test consists of:

· Photoshopped landing page mocks for each name, each with completely different copy, style, and images.

· Five second tests for each mock, after which the testers are given a series of questions about what they just saw. The questions are the same for each mock.

· To assess, we give each response a score of 0-2 or 0-1, depending on whether accuracy is nuanced or binary.

We run the tests for three days. Word to the wise—Google doesn’t like when you tie adwords campaigns to websites that exist only gather peoples’ information. But you should get about three days before they ding you, provided you don’t mention any Google product in the ad text.

The descriptive name wins the quantitative test by a handsome measure, and comes in a fairly close second on the qualitative test. When I express surprise about this, my coworker hypothesizes that perhaps the names that receive so much media love are not all that resonant outside the Bay Area and New York.

I get to work researching domain names and twitter handles, though every so often, my hand goes to my neck, twirls a strand of imaginary cryssals.

Is that the end, then? That descriptive names > metaphoric names, unless your app is specifically tailored to a Silicon place?

Maybe for some. For us, as it turns out, the original descriptive name isn’t going to work, so we’re going with another “box” name. One that happens to already be a key feature of our app.

Aka yes, it was under my nose this whole time.

Occam’s Razor, you have a new convert.

*Cryssals are light and fifty dollars. Plus they’re diamonds.