A lot of folks start their fundraising efforts by targeting their first choice prospect and working down the list.  It’s instinctively the most natural thing to do. 

But unless you are a really good fundraiser and know that the process will be a slam dunk, I think this is exactly the wrong approach. 

Practice makes perfect, and fundraising is no different.

Fundraising unfortunately is as much about how well you tell your story as it is about the content.  And most people only get better at telling their story the more times they do it.

You also can iterate along the way and figure out how to best communicate yourself in a way that is enticing to your audience.  This also requires market testing and can’t be done in a vacuum. 

Instead, I’d recommend actually starting the fundraising process by targeting folks in the middle of your prospect list, or even guys who you know will give you real feedback but are long shots.  It hurts to hear no early on, but it’s important to practice and battle test your pitch when there is little on the line. 

I wouldn’t do this too much, or your story will get stale in the market.  But I think you definitely shouldn’t walk into a meeting with your favorite VC and give your pitch for the first time.  Get your story straight, know the questions you are likely to get and prepare for them, and even create some heat around the investment by getting one or two others excited first.