The very popular file sharing service, formerly known as YouSendIt, has now changed their name to Hightail.  No, keep reading…I’m serious.

This is what their homepage takeover message looks like:

So the obvious question is…why?  And let me qualify that question with some color.

Why, if you’re a file sharing service, a service that allows YOU to take a large file and SEND IT to someone else (for free on the basic plan, I might add) change your name from YouSendIt to, well, anything else?

Why, if you’ve invested all this time and money for nine years in the back end cloud storage virtualized pool infrastructure, and invested in acquisitions and technological upgrades, and invested in marketing and advertising, would you change your name from YouSendIt to, well, anything else?

Why, even if you’re announcing broadening your offering from file sharing into digital file collaboration services, would you change your name from YouSendIt to, well, anything else?

Why, when there’s nine years of brand equity built up, when you’ve outlasted some pretty high profile would-be competitors, (including the flailing DropBox,) when you’ve gotten 4 out of 5 stars from PC Magazine, when you’re finally turning a profit on the premium services, when you’ve become the generic term for Internet file sharing services (literally, people verb-ize file sharing as “I’ll YouSendIt to you later,”) would you change your name from YouSendIt to, well, anything else?

It could be a number of things.  It could be new CEO Brand Garlinghouse (formerly of Yahoo!) putting his fingerprint on the company he’s been appointed to run.

It could be that YouSendIt doesn’t sound sexy or silly enough, and they wanted to sound more like Yahoo!, or Hulu, or Etsy or whatever.

YouSendIt could have done a lot of things to refresh – which they’ve done with Hightail.  New, HTML5-coded website.  New features.  New look and feel.  Heck, they could have updated the logo.

And the folks at Hightail know the name thing is an issue.  It merits above-the-fold position on their homepage with a message that says “watch this short video to learn why we changed our name.”  Yes.  Let’s:

Okay, but still, the new name thing confounds me.  In the video, you hear some of the talking heads saying things like “the name YouSendIt constrained us in terms of our vision.”  [Tell THAT to Google.]  And “we don’t want a name that holds us back.”  And my favorite “we finally have a second chance to make a first impression.”  And that’s the quote that really stands out for me.

Because here’s the dirty little secret about branding that nobody teaches you in b-school.  You don’t get a second chance to make a first impression.  You only get one chance to make one impression to one prospect at a time.  And in my opinion, Hightail doesn’t make a bad impression.  It does something far worse.  It makes no impression at all.  It confuses rather than clarifies.

Don’t get me wrong.  I get “hightail” as a verb.  “I’ll hightail it over to you.”  Or “you hightail it over to me.”  But we’re not talking about meetings here.  [Really, “I’ll hightail it over to you” means “I’ll be right there.”  Not “I’ll get you that large file right away.”  So there’s even a semantics issue. Ugh.] Plus, it’s such a hipster-cum-corporate-acceptable piece of jargon. I wonder if they’re now headquartered in Dumbo?

From a pure brand perspective, the truth is that YouSendIt was a GREAT name for a brand.  It was functional.  It was short and sweet.  But mostly, and bestly (?) it conveyed a promise (You.  Send.  It. ) which, after all, is the heavy lifting of a brand.

Let’s watch and see what happens together.