First up, he's a long time friend of mine, but not someone I ever will get along with in the same room for more than an hour. In the past, I've had a lots of insecurities and he used to be the proverbial pack leader that you always obey and don't piss off, because he could easily turn the other members of the pack (who are also extremely close to me, I like the others more than I like the pack leader) against you. This is the sort of relationship it used to be when we're 12-17.
We drifted off our own paths after 18. He's doing his thing, I'm doing mine. But the patronizing attitude of his really rubs me the wrong way every time he talks to this date. We're both 23 now.
I'm studying for an advanced degree (Masters) and he is not, but he always acts like a father-figure type of person who knows it all, except that he doesn't, and he's not a father figure. He just wants to let you know that he's better than you. I'm saying this not because I'm insecure, but because this has been made apparent in multiple conversations. He's an entrepreneur. I don't know what he's doing with his company. Whatever the progress maybe, I honestly, don't care. He could be a billionaire one day, or not accomplish much.
But he says something along the lines of 'We can hire you if you finish a post doc and an MBA'. Now I try to stay humble, by saying 'Thanks for the motivation man, I'll work super hard', when in actuality I have zero interest working for him because it feels like he doesn't know what he's doing with his company. He's still working on the idea! Inside my head, I really want to tell him 'Bro! Why on earth would I want to work for your company when, with those credentials, I could either start my own or end up in a place like Google?' I either ALWAYS come off as too rude, or too soft.
He's the sort of guy that would say something like 'I want you to implement this thing that only a post-doc researcher can do. We'll split the profits 70-30, I take 70 because I'm the CEO'.
I need to be able to tell him to not tell me what to do and not sound arrogant while doing so. Because he's continuing to send me actual images of his conversations where his advisors/HR consultants give him a salary quote for a position in his company and he can send it to me to 'motivate' me.