Another key lesson in fundraising: you gotta ask for what you want! VCs expect you to be pushy and they love when you are aggressive. It is a signal that you will get the job done. It’s hard because you its easy to fear that being pushy shows that you’re desperate and thats, of course, the kiss of death. This is not true though. In dating and in fundraising, it’s the same thing: you gotta know what you’re worth and what you want and you’re not bashful about making it happen. Any other kind of stance is usually some form of posturing which never works.
This was a particularly tough learning for me because of my VC to entrepreneur transition. As a VC, you train yourself to rarely lever “ask for what you want” because as a VC you generally think this will sneak into the valuation negotiations or the interpersonal power dynamics. In reality, this line of thinking and being is an illusion, both for VCs and for entrepreneurs.
Looking back, most of the successes I’ve had in my life (closing deals, finding my wife, buying my home etc) were when I saw what I wanted and went for it. So the moral of the story is if you finally find a VC you really like, you gotta go for it. It’s this kind of self-effacing push that’s always worthwhile and creates results.
But, of course, you gotta be careful about not coming on too strong. As my mother-in-law is known to say, “keep it light”. With a lighthearted but direct approach, you can’t lose.