My force-ranked list of criteria:
#1. Who do I truly trust the most? This doesn’t mean who is the “best guy”, or smiley-est, or nicest. In fact, be wary of “grin frackers”. Find out — who can I truly trust? If any of them. You will be so, so, so much better off if you pick the one you can truly, really trust. So, so much better off. A different way to ask this question — is who will most have my back?
#2. Who can truly help the most? In later rounds, this doesn’t matter much, but in the earlier ones it does. Pick that one.
#3. Who will the Next Round VCs most want to follow? This is hard to know without really asking, but if you pick a VC that other great VCs want to follow, the next round will likely be much, much easier.
#4. Who can promote me the most and help me be Hot? Or At Least, Cool. Later this doesn’t matter but some VCs really can promote you and help attract the best hires, etc.
#5. Which partner has the most successes under her belt? Nothing wrong with a first-timer or new GP, but a GP without any wins under her belt yet is often … more … nervous.
#6. Who has a bigger checkbook? This doesn’t always matter, sometimes not at all. But it’s nice if they can give you more money, vs. being tapped out, or stressed about the next check.
#7. Who do my existing investors recommend? They may not know, or have biases. You may need to ignore this advice. But if they are really experienced in the space … they’ll know. Something good here at least.