The difference between success and failure -- closing an early customer, raising capital, making a key hire -- often boils down to simply making the ask. And this makes a lot of founders wildly uncomfortable.
As one CEO asked me a few months ago, while complaining that his fundraising calls were stalling out, "we all know we're here to fuck, so why do I have to explicitly ask?"
Dude, even at 2a, one person still has to ask the other to go home with them. And it's usually the person who wants it more.
If you want something for your startup, it pays to be clear as day about it.
"I want you to invest in my company."
"I want you to hire me as a coach."
"I want you to join my startup and help me have a huge impact on the world."
The more you say it, the easier it gets. So start practicing today.