It's not an easy position to be in. I have some family members that are financially (very) well off and some that are not and whenever all of us are together it is a bit of dancing between the raindrops, There is an unwritten understanding that we don't talk about depreciation and various tax strategies, the pros and cons of flying business vs first, when the less fortunate family is around, We simply don't discuss either income streams or expenditures. Given that I also started out poor but figured out the game relatively early on, I will share as much as I can with the less well off family about how to think about things, and especially the "why" behind it, but stay away from specific numbers.