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Why not target a full time role?
He has no exp. To OP, yes. Any exp is good exp.
You’re not supposed to need experience for an entry level role. He’d be doing roughly the same thing as an intern that he’d do as a new analyst, so what’s the harm in targeting an actual job?
Yes, but gradually. If you expect to see this person a few times in the future, I’d start by casually asking him about his work, how he got there, etc. Mention that you’re wanting to learn more about the field but don’t know where to start. Emphasize your eagerness to talk to people and learn. Ask him if he knows anyone who might be a good person to talk to who are in roles you want to learn more about (banking, PE, other family offices, etc.). That way you can feel out how receptive he is to helping you and you don’t just swing for an internship right out the gates.
Also a MBA might be worth considering for someone in your shoes. Good luck!
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Just ask
Given he has explicitly expressed interest in helping you, I would definitely go ahead and ask him. How you directly ask is up to you but personally I would regret not asking if I were in your shoes. The added context you provided definitely supports the idea of asking rather than not. So, you have my support, good luck!
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