The brand name Hipmunk – among many other characteristics it has like internationality, memorability and searchability – does something very simple that has been a mantra of web companies ever since their market got called 2.0: it breaks a norm.
Breaking naming conventions or norms is actually not a simple task, if you want to do it in a constructive way. Of course you have to be aware of all the conventions in the brand space that you will likely operate in, and then break some. But gently. Because you don't want to try to break your potential customer's habitualization up too much. Read on to find out what habitualization is and why I suggest not to break it up too much.
Habitualization occurs when regular, frequent, routine interaction with something tends to render the way we respond to this thing a matter of habit, something we largely aren’t aware of anymore because we have come to accept that we simply don’t have to pay it any substantial attention. In other words: To reduce complexity, our brain stops thinking about it. This happens with people, places and even with brands and purchase transactions (one of the reasons why phishing is so successful).
Try to remember the last time you bought a pack of toilet paper. Did you make an educated choice, or could it be that you just grabbed the pack you always grab? That's called habitualization.
The same goes with brands. The problem? If you're new to the game, people who are frequently booking flights with Site X probably won't give much of a thought about you and go ahead and book with the site they have always booked with.
De-habitualization helps your company by stopping people for a second and making them think again. In that brief moment of open-mindedness and mental activity, the consumers have time for your brand of toilet paper – or flight booking service. Hipmunk's name does exactly that: in a sea of conventional names, it makes you stop and think "What the heck – that's a silly name!"
The only problem I see with Hipmunk's name is that it crosses the fine line of de-habitualizing a bit too much. Sure, the name appeals to you-n-me-customers, but if they want to ever penetrate the largest market of flight bookings, they will face a problem because of their naming:
Frequently flying buttoned-up businessmen and companies probably won't like their secretaries booking flights at a site called Hipmunk with a cutesy logo.
See the answer on Quora: