Why don’t more entrepreneurs drive to the money? I think it’s because just about everyone would rather engage their inner artist/creator over their inner salesperson.
Don’t feel bad about it- we’re just wired that way.
That said, if you want to buck the odds and make yourself a successful entrepreneur you need to diverge from the herd. One such divergence is asking for money sooner and more often than you’d like- for most of us, a lot sooner and a lot more often.