When should I pitch?

The answer is almost always too early and too often.

It sounds counter intuitive but here are a few reasons why you should present your story at the beta stage of your pitch. Keep in mind I typically hear founders pitch at the Pre-seed, Seed and Series A. The further along the company is, the more the founders think they’ve nailed their presentation and don’t need a beta pitch. They’re usually wrong.

1. Practice makes perfect of course. For the parts of the pitch you have down pat, the story that makes sense and the facts that you’ve already got right I say “practice, practice, practice.” I do not believe it’s possible to over-practice (not be confused with over rehearsing).
2. For the parts of the story that you haven’t nailed, now is the time to try out a few new versions. It’s not that you should go into any pitch being completely unprepared but there will always be nuances that haven’t been ironed out it. Questions such as “Should I talk about the team first or last?” or “How detailed should I get when discussing our defensibility?” can all be figured out and settled on during the beta pitch with slightly friendlier recipients on the other side of the table.
3. Data comes across in different ways at different stages of a company’s existance. It’s not that investors don’t want companies to produce revenue early on (at least I sure do) but the earlier the company is the less meaning that revenue has. If you launch your company and hit it big on ProductHunt or Reddit or sell out via the Digg Store or Woot it’s likely not repeatable. Practicing your pitch over a month or two can help to nail down the metrics that hold the most truth and value. LTV starts to have meaning as customers churn out, CAC is real when there’s an actual measurable cost and margins begin to hold serious power when you’ve figure out how to calculate them correctly (I like this post on the margin topic from Mark Suster a lot).

As I mentioned, over time you’ll be able to hone the pitch — your beta pitch. People on the other side of the table will begin nodding along and pounding the table in agreement instead of constantly poking holes in your story. As this happens you’ll realize the difference in power your presentation holds. This is when your pitch graduates from beta to v1 and, likely, when you close your first check.