How to date a VC?

There are a lot of advisors, bankers, networks, lawyers, and people who will gladly take money from entrepreneurs to get them "in" with a VC. To the inexperienced entrepreneur this seems like pure gold—worth it at any price. But let's face it, they're not getting you into see the Pope—or Mick Jagger. In this case, the VC wants to meet you as much as you want to meet them—at least until they have heard your pitch. ;-) For sure, a warm introduction is a key first step to get in, but it seems to surprise many entrepreneurs that VCs sometimes answer their emails (well, not that often, I suppose). Anyway, they are in the business of investing in entrepreneurs, so in a sense you are their customer. (Well…also their product, or at least the raw material for it.) The key is to do your homework. Verify that the fund is into the space you are in and find out which partner is the most entrepreneur-centric (for the first meeting, this would be my personal bias). Look through the portfolio to see what else they have invested in. If you have access to one of the venture data bases, great; if not, connect with a portfolio CEO or lawyer who does. Otherwise, just search for the historical announcements of deals and build a perspective on the founders and companies that this particular VC has favored. Then, connect with those founders to get their personal experience with the VC. These founders are also likely to be great sources of the much-needed warm intro needed to meet the VC as a prelude to the first date. :-)

Sending a business plan cold into a VC firm is a waste of time—it may get into the hands of an analyst more as a training exercise than anything, but it's a low percentage shot. You must be far more targeted than that; a partner in a good firm will see thousands of pitches in a year (actually looking at hundreds) and fund a couple. You must have the warm introduction. Your service providers, corporate counsel, patent attorney, accounting firm, landlord, banker, and your CEO friends are all great sources of warm intros. Also, VCs you failed to win—if your idea has any merit—will usually refer you to one or more of their buddies to hear the pitch. Ideally, you should send your contact a really simple, short teaser email about what you do that is cheeky enough to catch the VC's attention and make them want to know more. A full-blown business plan won't do this (a 10-slide deck might), but a short paragraph that encapsulates the elevator pitch will almost certainly be read. That, combined with who is sending it to them, is usually enough to get you in to the first meeting.