This came up during the Pinny Arcade 101 panel on Thursday (in the context of getting community pins recognized as official) and the response was none too optimistic.
(Complete speculation on my part)
I imagine the answer to your question is not just money, but also a certainly popularity requirement. Penny Arcade likely charges a licensing fee to be able to use their trademark. On top of that they also likely have certain requirements as to who they will license use of the mark to. They want pins to be exciting and the best way to do that is to attach them to popular IP. If they license out to unknown developers/parties then it starts to diminish the excitement of the brand.
I couldn’t find a good point of contact for PA’s business end of things but the only way you’re going to get an actual answer is by making a professional inquiry. Hopefully someone else here can point you in the right direction.
BekerChild's Play Program DirectorSeattleRegistered User, Penny Arcade Staffregular
Since there are also likely some community's thinking about pins that might be browsing these threads, let me say that you also need to be an entity that can legally sign a contract. So like, an actual legal organization of some sort. Or theoretically an individual could also do it, but outside of someone wanting a pin for themselves (like an bandland artist of streamer or something) the process is really set up for organizations.
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(Complete speculation on my part)
I imagine the answer to your question is not just money, but also a certainly popularity requirement. Penny Arcade likely charges a licensing fee to be able to use their trademark. On top of that they also likely have certain requirements as to who they will license use of the mark to. They want pins to be exciting and the best way to do that is to attach them to popular IP. If they license out to unknown developers/parties then it starts to diminish the excitement of the brand.
I couldn’t find a good point of contact for PA’s business end of things but the only way you’re going to get an actual answer is by making a professional inquiry. Hopefully someone else here can point you in the right direction.
TLDR: you probably need money and street cred