You need to remember this is an old school guy (late 40s, early 50s?), coming from a time where driving a loud car is seen as a "cool" thing to do and a way of measuring your dick size. Troy is a great speaker and he certainly makes a good career out of it (and selling stolen passwords to companies), but he also loves to show off his wealth which is a bit old school and weird nowadays.

From my experience, the happiest people I know never show off their wealth or put a lot of value on materialistic things, because they just see them as a way of means, not the end goal itself. Troy has a more traditional/conservative/old school outlook on life where the wealth is the end goal itself and the definition of happiness (to him).