>I owned a nice home, a beautiful vacation (lake) home, a big office building, 2 Mercedes Benz (wife's SUV, my car) [. . .] It all went away (except for my primary home) by the time I was 35.
One lesson here might be to not buy the fancy, expensive stuff and the lifestyle that goes with it. I bet things would've been a lot smoother with fewer gee-gaws and more cash in the bank.
I get the point here, and I'm not advocating never spending money or doing anything with your money, but the vacation house and expensive cars seem like unforced errors that don't really add much to one's life, especially relative to their costs.
Indeed. To put it another way: when your income variance is high, averaging (smoothing out expenses) seems pretty important -- at least, it would be to me. Calling a cavalier lifestyle intrinsic to entrepreneurs (in general) seems misplaced. It sounds more OP's individual choice.
One lesson here might be to not buy the fancy, expensive stuff and the lifestyle that goes with it. I bet things would've been a lot smoother with fewer gee-gaws and more cash in the bank.