My key takeaways from this
- people are more willing to help when you ask specifically. be sure you are asking the right thing to the right person. Dont ask for investment advice. Ask if xyz is a good investment for you in their opinion.
- People get defensive so as to not hamper their relations with you and keep out the honest and risky parts. Also they usually dont admit or undermine the luck and timing factors that went into their own life.
- Give them enough reason to show why you are a worthy investment of their time and resources.
- Be clear that you do not expect anything more than advice and guidance from them. Demonstrate to them how their advice was useful to them (a quick text is all it takes).
I feel talking to people beyond your age, occupation, geography and economical status is more fruitful and enjoyable.