You should be distilling your elevator pitch down to a tweet as soon as you think about your idea. If your elevator pitch is timed for the 60th story then you’ve already lost. In today’s attention starved world you need your value propositions distilled down to short bites that build on one another, can be taken out of context, and are built to be passed around, liked, and retweeted.
It’s ok to start wordy. I’m a big believer in just writing down all sorts of possible plans, options, feature ideas, etc early on. When we first documented KickoffLabs it was a 4-5 page plan with a few slides for mockups. But then you have to cut, shorten, and cut more. Your goal should be a series of tweets that explain your idea and features in different ways.
Then the fun begins, these are the test messages you should be using when you meet people to discuss your latest venture in person. You’ll know which ones work and which don’t by the look on the faces of your audience.
I can’t tell you how many times I had to go back to the drawing board in my mind after seeing the confused look in someone’s face. But with practice and refinement you’ll find a message that people understand and is memorable at the same time. That’s when you know you’ve got a message you can start selling.