should I contact this person for help?

I don't have any direct WS connections, and I am thinking of contacting someone who does. However I am concerned that it might be strange to do so considering the circumstances:
I went to a prep school for high school and there was a person who sent all his kids there and was involved in the school affairs. I didn't really know any of his kids that well. He was a big donor though, and I knew how powerful he was even then. I thought about sending him a letter (at his company) asking if I could speak with him about prop shops, etc.
He is somewhat famous on WS, and has big connections. If I mentioned his name (which I will not) some here will know he is.
Is this a silly thing to do considering I never spoke with him directly before?

 

nah that's what networking is all about..i'm in the process of contacting people from my school and i've never spoken with them before.

say you went to a high school where he donated too and ask him if you could speak to him on the phone or in person about trading or w/e.

 

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