I was just chatting with a friend that is a successful entrepreneur, advisor, and angel investor. He has 1700 unread emails in his inbox. 1700!

This happens to him every month or two. All it takes is a few days of vacation, a company emergency, a funding round, or any other real life issue. Email just loads up on him. He's always trying new GTD strategies, collaborative software, inbox fixer programs. They all help to some degree, but the reality remains that he receives a shit ton of email.

You know who else receives email like this? Every VC you've ever emailed. Every angel investor. Every biz dev contact at company XYZ.

I get a lot of email, but nothing at this level. I've got my inbox zero strategy, my gmail labels and filters. It's all basically manageable for me. But not for investors. Investors are constantly flirting with suffocation from email overload. Every once in awhile they just delete and start over

If you're trying to reach one of these guys to pitch for investment, advice, or a deal, you need to be conscious of their needs. Email etiquette from company founders often just sucks. And when you receive no response back from an investor, you'll never know that it was your email etiquette that sunk you, not his actual disinterest.

You need to assume several key realities about the target of your email. He has received 300 other emails that day. He has temporarily forgotten how you met. He has temporarily forgotten everything you've already talked about. He has 20 seconds to spend on your email before deciding to handle it later (which may mean never). He probably won't click any links or open any attachments.

All of this is irrespective of the fact that he may indeed care about you and your startup. But email is such a burden on his life that he just can't be accomodating when it comes to triaging hundreds of emails.

So a few email etiquette tips:

Subject Lines Matter

A lot. Your subject line should be uber-concrete and descriptive. Bad: "Re: fundraising advice". Good: "Seeking fundraising advice for my startup FlightCaster (as per intro from John Smith). If you can fit the entire question into the header, just do it and include #eom at the end, which means 'end of message'. Yes, it feels weird. Do it anyways.

Use Your Company Email Address

Everyone has multiple email addresses now. When you randomly email or respond from your personal gmail account, you make it harder for your target to search his archives for context on your conversation. If you don't include your company name, he won't even know what you do!

Remind Him of Context

You met him at a conference and had this fabulous conversation about your startup, and he totally got it. You just know he got it. Guess what? He's had 137 conversations with other entrepreneurs in the last 3 weeks. Remind him of where you met, what exactly you do, and how you met.

Limit Your Entire Email to 5 sentences or Less Seriously. I know it's painful. You have so many important things to say. However, getting it read is more important than getting all that explanation in there. Preferably it's 3 sentences. Your goal is to make it easy for him to respond immediately from his smartphone. Make Your Ask Explicit If you want a meeting, ask for a meeting. Provide some time options and ask for a specified length. If you want an introduction, ask for an introduction. If you're looking for funding, tell him you're currently fundraising and ask to meet to show him your pitch. Don't be sly. Don't hint. Make the process ridiculously easy by just asking for what you want. Respond Immediately Show your target respect by responding to everything immediately. Just because the VC you're emailing might not get back to you immediately, doesn't mean that you have the same privilege. Ron Conway famously makes immediately email responses a pre-condition for investment. Include a Short, Professional Signature My standard signature includes my name, company, blog, Twitter, and LinkedIn. If I want a phone call or fax or meeting, it'll include phone number, fax, address.