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In our ongoing efforts to understand and master Twitter, we’ve come across a common problem: with a message limit of only 140 characters, how does one deal with long URL’s that can sap precious info-space?

There are more than a few options out there, so in the interest of sharing our experience, we’ve picked a representative (though admittedly not comprehensive—there are tons of them) sample of URL shortening services and broken them down in terms of branding, ease of use, and additional features.

Three Services Enter

Branding: (Fail) The least recognizable of the three. What’s the name supposed to mean, “is good”? Bah. Although, anyone who doesn’t use TinyURL seems to use it.

Ease of use: (Winner) Is.gd has a great little Firefox plugin that puts it in your right-click menu. Activate it anywhere on a page (you don’t have to select the URL at all) and it goes to your clipboard seamlessly.

Additional features: (Fail) None that I can think of, unless you have £1,000,000.

Branding: (Tie) Clever, evocative name—I can remember it. Dot-notation always bugs me, but it’s pretty minimal (not like del.icio.us; man, I hate typing that out). Although, other than Paul and myself, no one else I know uses it.

Ease of use: (Fail) Tr.im has a bookmarklet to convert a selected URL. It takes you to the Tr.im page and puts it in your clipboard. Two gripes: 1.) I don’t like having my browsing interrupted 2.) the clipboard copy doesn’t seem to work for me (I have FF3).

Additional Features: (Winner) Tr.im’s claim to fame is that it allows you to track how many people click each of your links. As far as I know, it’s as close as you can get to some form of Twitter analytics. Unfortunately, the interface is a little half baked (though improving), so other than raw clicks, you don’t get a whole lot of usable information. You’ll just feel better knowing someone looks at your feed.

Branding: (Tie) TinyURL is the first and the original; everyone knows it. I have no problem remembering or recognizing the name. One thing, though: TinyURL is two characters longer than the other two shorteners in the lineup—space matters!

Ease of use: (Fail) TinyURL conversion is automatic in Twitter, so it can’t get much easier. However, I find it to be a poor implementation and I just don’t trust it. You never know how short the new link will be until you post the tweet and you can easily end up over your character limit, which can butcher your text. Also, from time-to-time it’s been known to create broken URL’s. Finally, the bookmarklet is crummy like Tr.im’s; it doesn’t go to my clipboard properly.

Additional Features: (Fail) TinyURL does have this thoughtful feature that allows you to preview links before you go to them (saving you from embarrassing or at least unexpected stuff), but it requires sending you to another page.

Forget that. Just get the LongURL plugin for Firefox, which does the same thing as inline tooltip. In fact, LongURL will work for all of these shortening services—how about that?

…One Service Leaves

Okay, so there is no clear winner here. However, I’m going to go ahead and say that if you’re serious about Twitter, TinyURL is not that helpful.

Is.gd is very clean and easy to use, so if you’re a casual user, it’s got a gold star.

For now, we’re using Tr.im because there’s some value for us in understanding how effective our Tweets are. If they could fix the interface, it’d be an unconditional recommendation.

A Parting Question

With that out of the way, I’ve got a weekday ponderable in mind: Can someone explain to us how these things make money? I assume that, at the very least, they have to cover costs.

I see no ads on Tr.im or Is.gd and little more than a donate link on TinyURL. So are they collecting and selling data, adding their own affiliate codes to Amazon/eBay links, laundering spam, or what?