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So I have already gotten a success from Tim McGraw via Redlight Management, and I have a few other (2 or 3) artists I would like to get autographs from and they are all with the same management company. Would it be okay for me to send again? Or does that seem greedy? I mean obviously they are for my personal collection, I'm not selling them or anything. And if I do send, should I send all 3 photos with 1 SASE, or do them separately like:

Artist
Red Light Management
123 S Street St.
Town, Zipcode

Opinions?

P.S, would this work VV for artists at the same show? If person A is the headliner and person B is an opening act?

There is no reason why you can't send to different artists within the same management.

Personally I always send a seperate envelope for each person, so if three are at the same agency I send 3 envelopes with 3 SASE's.

No problem doing it the same VV