14 Ways VC Fundraising Is Like Dating

A lot of first-time entrepreneurs scrutinize the web-o-sphere and the blogs of folks wiser than I like Fred Wilson and Mark Suster for advice on how to come up with the perfect pitch to VCs, but they miss the most basic truth: VCs are people too, and people are all about relationships. So, in honor of February 14, Valentine's Day, I've put together a list of 14 ways VC fundraising is like that oldest of human relationships: dating (or love, if you want to get all historical on me):*

1. You start with coffee.
2. There are lots of "dates."
3. If you're not interested you try to let the other side down gently - "I don't want to lead you on."
4. The side that starts off aloof can be the side that ends up falling in love - and the one that gets its heart broken.
5. Begging the other side to give things another chance rarely works.
6. You can't reason your way into a relationship (aka He's Just Not That Into You)
7. There may be numbers involved but ultimately it's based on a feeling.
8. Timing is everything - "This just isn't the right time for me to get into a relationship."
9. "You remind me of an ex" (another company/investor that left a bad taste).
10. It's not about one side choosing the other but about both sides finding the right match.
11. You hope it's about more than the money.
12. The holy grail is a true partnership.
13. When the relationship is ready to be consummated there is paperwork to sign.
14. Moving too fast often produces bad results.

Happy Valentine's Day!

* Please have a sense of humor when reading these. They were written to play off of well-known stereotypes about dating rather than any opinion of how dating should be.