Your boss seems to be an energetic , good hearted individual, and a hard worker, with lots of people skills. You sound like opposite personalities, and perhaps he would like more of your conservatism in his business structure, which is why he asked you to be his partner. If more sound business structure would make you comfortable, why don't you prepare a written point by point proposal of conditions under which you'd like to work. Like reporting income, and paying taxes and health care insurance benefits:) Build on his positive attributes, and don't forget to start off with mentioning your appreciation of them when you talk to him about a possible partnership that would benefit both of you. Ideally you can help him avoid a lot of potential aggravation and misery from the IRA down the road, while helping make the business prosper.