The other day, I sat down with Esther Dyson to interview her in advance of the Supernova2008 conference. Since Esther’s emails close with the saying, “Always make new mistakes,” I asked her if she often saw people making the same old mistakes, and what advice she had for them.

Now, I was thinking she might answer something along the lines of, I don’t know, venture capitalists still act like lemmings or entrepreneurs don’t give up on stupid ideas fast enough or something. Instead, she surprised me by saying, “I am appalled at the basics of email.” I asked for clarification, and the result comes out like a primer for pitching Esther, or anybody.

1. Remember the subject line – make it meaningful. Not just “Hi!”
2. Don’t go on and on, and hide the date you want the recipient to do something in the 6^th paragraph.
3. If you want results, you must accommodate the person you are approaching – don’t make them work. For example, re-attach the original document in a reminder message!
4. If you want an intro, write the email so that all the recipient has to do is forward it.
5. If the message takes four sentences, don’t add an attachment that they have to open.
6. If your company looks “just like” a company she’s already invested in, that doesn’t necessarily mean she wants to invest in number two!
7. If she says your company is not ready for prime time, don’t bother asking her to introduce you to John Doerr.

In brief, Esther says, “If people did email right, they’d get better responses.” I had to guiltily admit that I’ve perpetrated some of these sins; maybe even in the email I sent her asking for the interview in the first place. Shame!

Image caption: What Esther will look like if you send her good emails!

What about real spam? “The way to solve it is to put the burden on the sender, not the recipient. It’s too easy to send mail, and there’s no penalty.” She’s trying to solve this with Boxbe, a company she has invested in. Boxbe scores email from one to ten; Esther doesn’t look unless it’s below a 7.

How does Esther sift through all the emails she gets, in an age where we are all inundated with email? She suggests “self-restraint” – Don’t sign up for those lists. Learn how to filter better. Get better at saying no politely and promptly.

The theme for Supernova2008 is “Challenges of the Network Age” – and Esther suggests that the real challenge is human nature. She told me a brief anecdote about Conrad Hilton, founder of the Hilton Hotel chain, on the Tonight Show. Carson asked him (I’m paraphrasing), “You’ve played host to kings and queens, to captains of industry. Do you have any message for the world?” And Hilton replied, “Put the shower curtain inside the tub.” Esther’s message: approaching things from the recipient’s perspective costs you nothing and means so much.