I think I’d try my damnedest to live a middle class lifestyle, even if I was sitting on upwards of a billion dollars in assets. After all, if I don’t spend it, it just grows larger.
With that, I think I’d make the boys mow the yard and do all the other menial tasks that my wife and I had to do in order to earn money. There’s a lot to be learned from busting your ass for very little, and yet being happy to have that little bit that you earned yourself. Especially if your parents take the tack (which mine did) that money you earn yourself is free to be spent how you see fit- your parents didn’t earn it. Of course, this freedom ultimately comes with some painful lessons in spending your hard-earned kid cash on stuff that isn’t worth it, or that doesn’t last, or whatever, but better to learn as a 11 year old than a 31 year old.
I think I’d also try and resolutely avoid buying them everything they want; if they want an Xbox, they have to save up for it, or go in with their brother, or otherwise not expect me to just cough up 500 bucks, even if I could do that as a billionaire the same way I buy a coke today.
Ultimately the point would be for them to live a life free from serious worry about shelter, food and environmental factors like that (I doubt it does children any good to worry about whether they’re going to get to eat, or if they’re going to have a home to live in.), but without very much in the way of rich-kid toys or treatment. They’d have to drive shitty cars in high school and college, unless they can afford newer ones.
I went to high school at an affluent private school. I hesitate to say “rich”, as most of my classmates were from upper-middle class families, mostly doctors’ sons, lawyers’ sons and small businessmen’s sons. But even they got some stuff that was just outrageous by the standards of my solidly middle/lower-middle upbringing. And a lot of it came with the typical high school aged obliviousness and arrogance, so there was pretty much no awareness that not everyone lived like that.
I don’t think it would have hurt me to not have to have worn Sears Outlet clothing in middle and high schools (or garage sale clothing like my wife did), but I do think that growing up in an environment where Mom and Dad bought me plenty of whatever clothing was fashionable at the time wouldn’t have done me any favors either. There’s a middle ground, and I think that’s what I’d aim for. No stress about environmental stuff like housing, food, college tuition, but not too much in the way of mollycoddling and spoiling either.