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I want to send one to a comedian that would be performing at a venue, but I don't know when to send it. How many days before they perform would you send it? Lets say the perform the 20th of this month, what would be the appropriate time to send it?

I'm no expert on VV, but I would say that a week to a week and a half out is a good time to send. You have to figure the time it will take to reach the venue, hit their mail room, get sorted and then passed on to the performer.

For instance, I sent to performers just last month who were going to be playing a venue on 7/24 and I mailed it too late on 7/16. I never received anything back (granted there's still a slight chance of me getting a reply, but I've seen other successes from that venue and I have yet to see anything in my mailbox). I should have sent probably on the 12th to ensure that it would get sorted and delivered on time. Hope I helped. Good luck!