First, let me just say I spent a decade working as a reporter for the NYT, the IHT, Bloomberg, Businessweek and others. For the last two years, I've done media relations for startups in one way or another. I'm not selling my services here.
Outdated info:
Alexia Tsotsis stepped down as co-editor of TechCrunch in May. She writes for them on a very occasional basis now.
https://recode.net/2015/05/20/techcrunchs-top-editor-tsotsis...
Robert Scoble, whose taste in fine alcohol Austen has highlighted, actually went on the wagon in January. Pushing him back toward his addiction is probably unadvised.
http://valleywag.gawker.com/robert-scoble-in-recovery-going-...
So the big lesson is: know your reporter. And I'm afraid to say that that doesn't scale. It's a lot of work by one human being, figuring out who covers what and how you can appeal to them.
That's why PR agencies exist. One small group of people does the grueling work of tracking down and getting to know reporters.
Unfortunately, PR agencies have a principle-agent problem. Most of their clients have no way to figuring whether they're doing their work well. They just know they're paying $15K per month. And in fact, more than half of all PR agencies suck, including some of the most famous ones. So you need to watch out.
One of the reasons they suck is they send out form emails, like the kind Austen is advocating here. Personalized emails don't really scale. Changing the names of the reporter and publication is not really personalization.
To be fair, Austen is right in saying you need a list of publications and reporters that may be interested in you, and you need to know where to situate those publications in a pyramid of importance. He's also right about the trickle-up effect. You want to start off Broadway, and offer increasing social proof of your newsworthiness as you move up the ladder (which keep going past TC to larger general-readership publications if you're lucky).
But if you send out a form email, you will piss off the people you want to please. They get 1000s of those per day, and they don't even bother to delete. Deletion itself would be too much effort. You have to understand that with the evisceration of the press in this country, the ratio of newsmakers to reporters has increased. The reporters are overwhelmed. You need to offer them something special.
And you need to do that from the subject line of your email -- that's your only chance to get any of them to spend an additional 5 seconds on your message.
And now I need to say something counterintuitive:
Your first message to a reporter shouldn't be about you. It should be about them. People approach PR way to late in the game, when they have a launch they need coverage for.
If you're smart, you'll start much earlier, when you don't need press, and you can simply offer someone help. Read their stories, figure out if you have information, insights or introductions you can make to help them do their job and look smart, and give them that.
It's better to start out giving rather than taking.
I wrote this free ebook for a startup where I worked two years ago. Some of the info may still be relevant and up to date.