Raising money is hard. VCs give out money for a living and put their email address next to it, so that should give you a sense of what their inboxes look like.
So how do you get in front of them? Once you do, how much badgering is ok? Is it persistence or annoyance?
Here are a few things I recommend but remember that every investor is different so there may be some disagreement.
1) Please stop introducing yourself in self-effacing ways. "You probably don't remember me" is the weakest opening line ever. Just tell me who you are, period. If I don't remember our previous conversation, then it's just customer feedback for you to make a stronger impression for next time. If I remember, I'll mention it, but at least you don't a) remind me that you're unmemorable or b) make me feel like a jerk.
2) Ask specific questions. Just getting "feedback" makes it seem like you're just poking around in the dark aimlessly. You should have two or three pressing questions at all times that are keeping you up at night. Ask me those, or did you just want me to toss up a big "9.5" placard like they do in the Olympics. Most conversations don't end in funding or even a follow up meeting, so your aim should be to get specific, helpful advice that moves you forward. If I'm interested from an investor perspective, I'll let you know. Plus, asking for short, pointed feedback lowers the bar for responding. I won't feel like I need to write an essay on the problems with your business and at least you'll get something from me.
3) Don't be afraid to nudge. If you emailed me and I didn't get back to you, just forward it back to me and say "Hey, not sure if you saw this." I'll prioritize responding to it and it makes me feel like you're persistent enough to close a sale or a hire. One and done emails make me think you're not aggressive enough to drive this company forward.
4) Do your homework. What is it about me that makes you want to pitch me? Figure out who I am and why I might like this business. Also, try to imagine the other businesses in the space I'm going to compare this to. When you're pitching for a million bucks "I've never heard of them" is not an acceptable answer for when I ask about the team that tried to do the same thing as you just two years ago. If you were leaders in your space, you'd know them.
5) Aim for me to hear about you before you pitch. Are you blogging really insightful takes on your industry? Submitting content to publications I read? Getting quoted? Do you know the industry experts that I know? Try to guess who my first due diligence call is for your company and get to them first before I bastardize your pitch to them.
6) The best in person approach I've ever see goes to Mike from Bre.ad. He saw that I was talking to other people at Techcrunch Disrupt to he quickly slips his card in and says "I just wanted you to match a name to a face. I'm Mike from Bre.ad and I'm going to email you later." Then he just walked away. It was so polite and respectful that I almost stopped him right there to talk more. He realized that rushed in person pitches don't do your company justice at all--especially when VCs are running to another meeting or trying to mingle and meet as many people as possible.
7) When being introduced to a VC, you follow up first, not them. This should be self-explanatory.
8) Handing VCs paper decks makes you seem like you just arrived from 1959--unless it's letter pressed on a vintage machine you and your ironic hipster cofounders maintain yourself in Williamsburg. Then, it's ok.
9) Don't start by asking if I invest in notes, blue websites, individual founders or some other random esoteric detail that isn't predictive of returns. Tell me how you're going to make a boatload of cash and then you can work down to those details. 99% of VCs invest in things that make boatloads of cash regardless of what they say they do.
10) Don't talk in generalities. "We're changing the way you think about life and existence." I'm sorry is this a startup or are you a Scientologist?
Other tips? Disagreements?