Practice makes perfect. Whether memorizing lines for a play, learning to play a rockin’ guitar solo, or pitching your company, practice is an important part of getting your message across. Everyone knows this, so everyone practices as much as they can.
I rarely come across an entrepreneur who hasn’t practiced his pitch to some degree of satisfaction. What I do see, sometimes, is what I believe to be the opposite problem: too much practice.
How can too much practice be detrimental? When it erodes the spontaneity of a performance.
What makes a great jazz performance, for instance, isn’t the melody at the beginning and end, but the improvisation in the middle. When a jazz performance is too planned out, it shows. It lacks a certain element of authenticity and engagement. In excess, practice sucks the magic out of what could otherwise be a great performance.
In venture capital, this is why second meetings are more important than first meetings. In the first meeting, all the jokes are funny. The vision is novel, and the team is pumped up to make a good first impression. The first questions that come to mind are the obvious ones, i.e. the questions the team is most prepared to answer.
Second meetings are more enlightening because, by comparing them to the first meeting, it becomes pretty obvious what has been practiced, and what has been improvised. While some things should sound practiced (biographies, financials, etc), I get a bit nervous when 90% of the pitch sounds that way.
There is a fine line to walk between polished and perfunctory. Don’t be afraid to go off book from time to time.