A few founders recently told me they keep many challenges to themselves because they don't want their VCs to think they're inexperienced or ineffective. IMHO it's better to tell existing investors everything if you trust them. They're *very* aligned w/your success & want to help.

Sharing challenges with investors and advisors is like asking questions in class: you can worry about perception, or you can focus on learning and improving.

Building startups is very hard, and there are no dumb questions.

As a VC, I'd much rather help someone try to figure out a problem -- even if that problem is one that most people would know how to solve -- than have them struggle unnecessarily for weeks or months.

Addendum: fwiw there are many things I don't know that you may expect VCs to know. For example, I'm not great w/cap tables & haven't managed or fired people firsthand. For me, the most effective approach when I face a new problem is to ask a few smart people how they'd solve it.