Questions for chairman of one of the largest developers in the US?

This shouldn't intimidate me, because I already work in the industry and I constantly "network" to begin with. And I know this has been asked 100 times on here.

But I'll try it anyway. Through a family friend I will soon get to sit down with the former (yes, he's retired ... but still very involved in the industry and very influential) chairman/ceo of one of the largest developers in the US.

Thing is, I probably don't really want to follow his path. He went to grad school, whereas I hope to never go. He joined a prestigious company and got promoted, whereas I would rather start my own or work somewhere small. I don't really have any great questions for him - I already know how his company operates, where their capital comes from, what sort of deals they do. Not really any mystery there.

Basically, he's a huge deal in my town. Imagine someone like Jerry Buss. We sit down together, he asks, "Okay ... impress me with your insightful questions. What do you want to know?" I don't have a great list. I've also heard he's kind of an asshole.