How to get TechCrunch to call you hipsters.
There are a few things I learned in getting this write-up from TechCrunch (http://tcrn.ch/9CU2MC) that I thought might be helpful to other founders:

1) Have something worth covering: This one's already decided by the time you're looking for press. Is your product novel, decently designed, work without breaking too much? Is your product interesting to the typical TC reader? You need to find the right jumping off point where you feel ready enough to 'show the world' and can scale requests, but still benefit from early adopter feedback.

1) Be human: TC is going to get hundreds of PR firms every day giving them press releases for every last product launched. What small or big company doesn't want to be covered? Think about what would catch your attention and keep you engaged. Your title, your product description, bio, and any other content should be as interesting as possible. Stand out.
i. Be funny. Maybe you are trying to be serious and you provide security tools for enterprise and it's just not funny business. I'm sorry. If you're doing a consumer orientated startup why not loosen up a bit and have the Jersey Shore crew demo your product? (http://youtu.be/B8qJPHBIxOs?hd=1) If you're going to be telling a story, make it compelling.
ii. Show them who you are. Tell them a bit about the human side of you. If you're going for the scrappy startup story then let them know you're bootstrapped and work out of your mom's garage. Send them a picture if you want.

3) Be persistent: I initially just submitted the contact form but got an out of office email. So I improvised and submitted the same content to tips@. Still no response. I sent them one more email saying we are pushed for timing on this launch. They finally replied and the process got going. It still took some time for them to slot us in, but it all worked out. Just be persistent, without being annoying.
i. Consider giving them the exclusive. They like new news... See here: http://news.ycombinator.com/item?id=198797

4) Be genuine and nice: these writers are doing their jobs sorting through all the days information to curate the right content for their readers. If MG wants to write about Twitter, that's his prerogative. You aren't there to tell them how to do their jobs. It turns out they can write pretty darn well and captivate a readership. All you can do is present a genuine portrait of your product and company. Being a jerk in the process will likely get you no where.

5) Be interesting: while there is always a ton of news going on in the tech world, give them enough interesting content about your product and team that they can create a narrative. We didn't tell them Plannr was for hipsters. We happen to send in a funny picture of the team, a video of the iPhone app being used by the Jersey Shore crew, and a product description. They are creative people, they came up with a better article tagline then we ever would.

6) Read this: straight from the source http://techcrunch.com/2010/08/01/how-to-get-our-attention-a-case-study/

In a way, this is all common sense. Yet, sometimes I think we have trained ourselves to act like PR drones when we can really out PR the drones by showing that there are in fact humans behind the product.

Obviously TechCrunch coverage isn't everything. It is not a new feature for your product or a new set of paying users. What it does do is get you in front of a bunch of early adopters for a couple days and you can get a flood of good feedback. I've heard it also does wonders for SEO if that's an issue for you. This did feel pretty awesome to see: http://yfrog.com/n7mwrp