(maybe the other party was bored by these conversations, idk, but they seemed to happen pretty smoothly)
One of the things I noticed as I got older, is that for any number of reasons, lots of people wind up spending 40 hours a week doing something other than what they hoped and dreamed they would be doing.
And they tend to not enjoy talking that much about it when they're off the clock.
People will tell you about what they do, but lots of people aren't interested in answering follow up questions, or making conversation about their job flow very smoothly; often the conversation gets stilted pretty quickly.
I make a point to never ask, unless it's a work scenario (conference/meetup). Besides, there's usually something more interesting to talk about.
Why? The goal of most social conversations is to find a common thread, and if your commonality with this mustache twirling yacht owning theoretical is that you have a little canoe you enjoy taking duck hunting, then you at least have the beginnings of your thread.
Wealth and it's presence or absence is not indicative of social or moral worth, nor is socializing about "besting" the other person with your knowledge of imported French brandy. You may well talk to the person for five minutes, get through the usual pleasantries, and find you have nothing at all in common and part ways - or you might both settle on talking about small game hunting.
unfortunately there is a lot of baggage wrapped up in one's occupation (social status, money, etc.). if, as a software dev, you start asking someone who works at a pizza place all kinds of questions about their work, it could be a very different dynamic.
btw, i used to work in a pizza place and i had devised all kinds of strategies to optimize every aspect of my job. i loved when people would give me the opportunity to talk about it, but i know a lot of my coworkers were very unsatisfied with their job and place in the world, and would not be happy to be asked about it by someone who obviously made a lot more money.