Doing this as a poor person is definitely more difficult. Most areas of work are heavily regulated and require tax fillings for permission/licensure. Once you become rich, you have more options though. The ultra wealthy funnel their money through foundations tax free. Others hold assets that appreciate while borrowing against them to avoid taxes. Sure you’re not free in the sense that you have to set up these complex systems, but these are all problems that are solved by just throwing money at them.