It's Adam Lisagor whose video production company Sandwich Video works on lots of startup videos http://sandwichvideo.com/
1. These guys have produced numerous videos for businesses that have gone viral and spread to millions of people. That's not to say that others can't do the same thing -- just that these guys have a history of success, which suggests that not possessing an "everyman" aesthetic may not be such a bad thing.
2. Most companies that use Sandwich for their videos are early stage startups looking for early adopters. Lots of early adopters work in tech and live in the Bay Area. So at this stage, making a video that would appeal to this niche of people makes perfect sense.
3. Being different (hipster) makes the audience remember the video, and hence the product, which is the purpose of the video.
"It's easy to think that the ads are designed to draw in the demo shown in the ads, but that's not the way advertising works, and consequently that's not how America works. If you're watching it, it's for you. These ads play heavy during late and late late night talk shows: the target is boring middle aged white people. Blackberry isn't targeting gays and limber blondes, it's pretending they are already on board so you don't feel like a dork without a touch screen."