I had a fascinating discussion with an entrepreneur a little while ago. Her company went down the drain and she bemoaned a series of “what ifs”. What if investor X would have put money into the company? What if person Y would have signed on as an advisor? What if company Z would have become a partner?
The thing which struck me was — she never actually asked. None of her “what ifs” were actually real missed opportunities where someone said “No”. They were all hypothetical mind games.
When asked why she didn’t ask, her answer was: The investor wouldn’t return her email anyway. The advisor wouldn’t consider speaking to her as he’s must be so busy. The company would surely not partner with a startup. So why bother?
I was blown away. Until I heard similar stories time and time again — often in the context of reaching out to “famous” people.
Do yourself a favor: Ask! If you don’t ask, the answer will always be no.