He's the owner of the company--it  is entirely his right what to pay through his business. He may elect to put all his expenses through the business if he likes.That said, if he breaks the tax law in some way, he can face substantial liability--fines, penalties, interest, and possibly jail time, too. The owner of a business may have the business pay all his expenses BUT non-business-related expenses cannot be deducted as business expenses...so if the apartment, for example, is used for visiting clients and for work, maybe that could be deducted, but not the homes if they have nothing to do with the company. Similarly, some entertainment and food is likely legitimate business expenses (e.g. meetings, client entertainment), but much is not. As long as he plays straight on what he deducts and what he doesn't, he's not breaking the law in this regard; but if he deducts non business expenses, he may be violating tax law.Also, while a company can reimburse someone for a business expense (i.e. business travel) without it being taxable income, alot of what you describe *would* be considered income that he has to pay taxes on. Again, as long as he pays the right taxes, he can do this; but he has to pay taxes on payments made on his behalf, such as, again, non-business expenses, which would constitute income.If you believe he is violatiing tax law, one option may be to contact the IRS, if you feel strongly enough about this.