I've seen this a thousand times. Guys who come from bad neighborhoods with nothing make it big, but have no idea how personal financing works.
Just another way our educational system is failing.
You actually think Nick and others like him paid attention or even attended school etc to have any idea about this?...
It is true that they don't really teach taxes but everyone knows about income tax and if they can't be bothered to learn how to do it themselves can easily get it done 3rd party.