It largely comes down to whether or not you direct and control the manner with which these maids work, which he certainly does. He has his maids wear branded uniforms, gives them a set checklist to follow, and has them bring a bottle of wine to each first-time customer. The fact that his maids have their own clients and use their own cleaning supplies does work in his favor, but overall he's still on the wrong side of the divide.

I'm not an employment lawyer, but I have been through a state employment classification audit, and I am pretty confident his maids would be reclassified if he came under scrutiny.

The IRS has a 20 point "Independent Contractor vs Employee" checklist, and he falls on the wrong side of a number of these items: http://www.webster.edu/about/policy/independent_contractor_c...