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When you have that much money coming, I'm not at all surprised that he lost track of a million in the first year of employment and that is if he even ever looks at those types of things. Especially if there were signing bonuses or things like attendance or win threshold bonuses in place.
It also sounds like he has some going as personal income and then some going into an LLC - probably so that he can 'employ' family members and friends and reduce his tax burden. I've seen high earners, who make much less, do things with LLCs like have pictures of their kids taken and send them out on cards or put them on websites promoting whatever they are promoting and then max out their young children's 401Ks and IRAs.
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