I'd like to go on the record as the pessimist in the room. If you go down this path, I strongly believe that you're going to lose your shirt building a bankruptcy machine. In many ways, the markets are a mechanism for transferring your money to the pockets of people who started out with more money than you.
I'd strongly suspect that this guy is definitely in the upper middle, to begin with. "Why buy a Porsche when a BMW will do?", complaining about the duldrums of a six digit income... talking about being easily able to have quarter of a million in savings at age 24... etc, etc.
We could be charitable and assume that he graduated from high school and college in 6 years, and was immediately hired into a well-paying job at age 20. With four years of pre-tax income at $140k, $200k in savings isn't out of the question. (Assuming a 30% marginal tax rate we get a post-tax savings rate of 51%.) Not typical in the slightest, but not impossible, especially if you're from a pampered background.
That aside, claims like this show a lack of perspective and the slightest overconfidence can cut everyone down.
