Well, not sure of the policies in Wisconsin, but it sounds like you are most definitely bending if not just flat out breaking the law. How much does this guy make? If it's over $600 per year, he is an employee. There is no way you can consider him a subcontractor. So you should be paying taxes on his income and unemployment, etc. You might be required to carry WC on him as well. Just because you are an LLC and have an EIN does not make you legit.