Wow, so many different answers. What a great thread.
I am the cheerleader type of person, and hope that all my friends have the best life they can. I am completely self made, so I feel like anyone can do it. So I find myself sometimes talking too much, too excitedly, about my great deals or multiple rentals. I think it's a bit off-putting for some, especially the ones burdened by short sighted spendthrift habits. I still make the mistake of thinking that people aren't actually running credit card balances, eating sushi when they have no money, etc etc.
But truthfully, I"m so darn HAPPY to be where I am in life that it's hard to restrain. I don't talk about net worth, because I know mine is pretty high, but I constantly talk about getting ahead through rentals, investments, prudent shopping, etc. It is such a focus of my life-- that I forget such happiness and excitement over the way that things are, exactly, right now, can be an enviable position.