It probably would be that simple. When you issue a 1099 to an LLC, it's not like you report the number of employees or even have to know how many employees that

It probably would be that simple. When you issue a 1099 to an LLC, it's not like you report the number of employees or even have to know how many employees that LLC has. Additionally, if that one man company is a C Corp, you don't even have to issue a 1099. So the state would have no record at all of you paying that company. And before anyone says that a c corp is a lot harder to form, it's not really. A little bit extra on legal zoom and that's about it. Additionally, as an LLC, you can elect to file taxes as a C Corp. Which again, absolves the "employer" from needing to file a 1099 at all.