What is the best jail time free black market job you ever had?

i've been a good boy my whole life- went to school, graduated with honors ,got a career in IT but have now learned that making ends meet in a rat racing 9 -5 vicious cycle will give me heart failure before I turn 26. So what was the best jail time free black market job you ever had? What are legal loopholes that make people rich today without having to ever get a job or work? Yes I'm turning lazy and yes I don't mind risking my life or freedom anymore.