Don’t. That’s my first reaction when I think about how to pitch a startup to a complete stranger. But that’s not the entire story.

I get pitched a fair amount from people with startups or startup ideas. Oftentimes they’re interested in learning about how to raise financing. I try my best to read all the emails and respond (at least to the better ones). And the truth is, I’ve been pitched “randomly” in the past on some pretty good stuff. So it’s interesting.

But I think it’s also helpful to have a de facto blog post that I can send people to before or after they pitch me to say, “This is what you need to do when pitching strangers.”

So here’s what I’d be looking for when you pitch me. These points are relevant when pitching others as well. Perhaps even more so if you’re going to try and pitch the big players and more popular bloggers like Fred Wilson, Mark Suster, Chris Dixon, etc.

1. Don’t be a stranger. There’s no reason that we have to be strangers. Comment on this blog. There are lots of posts here about raising capital, starting companies, etc. Become an active member of this community. Follow me on Twitter. It’s so easy these days to interact, and the better we know each other, even at arm’s length, the more receptive I’ll be to a pitch.
2. A short email. Long emails are killer. No one is going to read a super long email from a stranger. You need to boil the pitch down to its bare minimum and make sure it grabs my attention.
3. A well-written email. Emails with typos, poorly worded sentences, messed up spacing, etc. will be deleted almost instantly. It’s a necessary filter mechanism. I’ll take into account situations where English isn’t a person’s first language, but even still — you need to be able to write and communicate effectively. Not doing so generally gives the impression that you don’t care enough to try. And if you don’t care, I don’t either (and no one else will.)
4. A strong executive summary. Since I’ve asked for short emails, how are you going to get me all the information I want? A pitch deck isn’t a great idea, it’s too long. You need a teaser. The executive summary is that teaser. It’s 1-2 pages in length. It’s a PDF, nicely styled (but doesn’t have to be designed by a graphics wizard), well-written and to the point. Having an executive summary also demonstrates your basic understanding of the financing process. Marco Messina has a good executive summary template for you to look at. You can also check out Guy Kawasaki’s thoughts on executive summaries (he’s right — it’s about selling not describing) and this presentation by Andy Forbes (although I don’t agree with all his points.)
5. Clear sense of the competition. There’s a good chance that I don’t know a ton about your industry (whatever it might be.) So when pitching, you need to make sure I can get up to speed very quickly. One of the key areas for that is competition. Too often, entrepreneurs will say, “There isn’t any competition.” Wrong. And too often, even when they know there’s competition they won’t address it head on. Bad. Address the competition head on, explain why you’re different (and better?!?) so that I can learn about what you’re doing very quickly. One of the best ways for me to understand your space is to look at the competition. And if you don’t tell me who they are, I’ll go Google them anyway.
6. You’ve done your homework. It’s so easy to see what things I’m interested in by reading my blog and Twitter stream. The same holds true with almost all angel investors, venture capitalists and entrepreneurs. Most of them are blogging, and almost all of them are on Twitter. So once you’ve done your homework you can tailor the pitch. Find an angle that you know will pique my curiosity. Don’t pitch me something completely out of left field with no reference point or indication that I know or care about it. I’ll be lost, disinterested and a bit grumpy about the experience.

Those are the basics. That’s the minimum of what I’d like to see when you’re pitching me as a stranger.

Ultimately it’s infinitely better to get a referral. Without a doubt, if you pitch strangers you should have very, very, very low expectations. Getting referrals is possible. It takes work and time, but it also shows a capacity for doing what it takes to succeed. I don’t want to completely discourage people from pitching complete strangers, but if you’re going to (and if you’re going to pitch me), I hope you follow the above minimum requirements.