On the hand-holding point, it's really just about taking action and trusting that you will figure out how to see it through to completion. You don't have to know much to set up a meeting with a VC, but you do have to follow-up and actually set up the meeting.
It's amazing how few people in the real world follow through on things this simple. I have a friend who complains about his job every time I talk to him. I've offered many, many times to put him in touch with companies he might want to work for and even an HR specialist friend at Google for some free career coaching. He always says "sure!" but never follows through. This has gone on for years. Years!
Asking for advices is not bad as long as you process it and act on it accordingly. Pretending you know something that you don't, OTOH, is another form of arrogance. I've never heard anyone say "that guy's not arrogant enough."
One of the best feelings when handing a task to someone is when you know that once you've handed it off, it will either get done quickly, or it will spawn a rich bramble of e-mail conversations that only ends when someone in the network has figured out what needs to be done, and then the person will do it. And if nobody knows, they'll be on the phone with you telling it straight the moment they realize that fact.
That's a very difficult quality to discern in the context of interviews, unfortunately. One thing that's useful is to try to push all of your candidates beyond what they can reasonably handle, and see how they react - people that are quick to look for help when it's needed tend to deal with these situations honestly and quickly, admitting the limits of their knowledge. The worst will just wubble about endlessly, never realizing that something is beyond their reach.
Once I realized how attractive that "quick to admit ignorance" quality was in job candidates, I stopped feeling so nervous about being interviewed, and started just being rigorously honest about what I can't do and don't know. It's better for everyone that way, and most interviewers I've met with seem to appreciate it. The only downside is that I've lost some work that I genuinely wasn't qualified to do, which is not such a great loss anyways...