There is something to be said about the psychology around being afraid of getting an answer of NO. As a bootstrapping entrepreneur you have to know that most doors won’t just open for you, you’ll have to kick them down.
However, kicking down doors doesn’t work if you are afraid to ask for uncommon things because you think the answer will be NO anyway.
This morning I came across an awesome blog post from Mark Suster titled The One Word That Shouldn’t Exist in an Entrepreneur’s Vocabulary. Suster states that his mom taught him at an early age that if “You don’t ask, you don’t get.”
Suster also says about his mom:
She was a hustler. And a ball buster. And a natural sales person. She was never afraid of the word “no” even to the point of embarrassing me.
The key takeaway here is that closed mouths don’t get fed. You should definitely go read Suster’s full post over on his blog.