Why does Tommy have so much debt?

I know I am probably reading too much into this. Why is Tommy so broke? If I am in constant contact with the CEO and vital to the operations of the business I would think I will make enough money to clear $500k on debt… those guys will be making at least high six figure/low seven figure?? He is effectively the COO of a company that is probably worth at least $1bn given that the owner is a billionaire…

Like CEO personal assistant will be making serious money so I find it hard to believe that Tommy still needs to live in a house share with 3 dudes… ha