[IneffablePigeon]

I agree. I respect Troy enormously on the subject of security (and making that subject more accessible) but I saw one of his "Hack your career" talks last year and found it to be much too focused on money, along with a big dollop of survivorship bias.

[dustinmoris]

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).

[aswanson]

I'm not too far from his age range. The "blatant brag" kind of plays out by your late 20s. At least it should, IMO. It's mostly just signalling to females, anyway.

[dagw]

At least it should, IMO.

It obviously should, but a casual observation of the world around me seems to indicate that it doesn't.

[tcbawo]

I'm not sure if this plays a major part in his psyche, but having dependents changes the game considerably. Suddenly, you're worried about providing for someone else's future (kids, potential grandkids) even after you're gone. But, then again, that makes flashy purchases look selfish and wasteful.