My boss owns his business and wants me to become his partner. I enjoy the work I do and see opportunity to make money with him, but his "financial advice" seems awful. Does this make him a bad person to partner with? His suggestions for me to save money: (1) Drop my private health insurance, (2) Reduce auto insurance from full coverage to liability, and (3) cash in my IRA to pay off my debt - a 43% tax penalty rather than the 5% tax deductible interest home equity loan that I took out to consolidate. These seem, to me, to be some of the worst financial decisions one could make. To me, they are risky and represent "living for today". I feel that doing these things would be financially irresponsible and gambling with my future. He doesn't pay taxes (cash business), doesn't use banks, cashes customer checks at a check cash place that doesn't report, registers his home and vehicles in his wife's name out of state, and pays me under the table. Am I crazy for even considering his offer?
Additional Details
Everyone thinks I am crazy when I describe it. But, with the exception of his dishonesty with the government, he is an honest guy - very rare in the contractor / home improvement industry I'm now in. He doesn't rip people off but makes a good living, every customer he works for loves him and refers him to others, has a decent customer base, and is a very moral person (again with the exception of the dishonesty to the government thing). There are certainly some things that bother me. He is licensed and insured, but if I were to get hurt and couldn't work right now, I'd have no disability or worker's comp or anything like that. If I became a partner - or maybe even if I don't - I'm guessing I might want to get some sort of private disability insurance or something so that I wouldn't lose my house and everything I've spent the past 10 years working for - if I couldn't make the payments for a few months because I fell off a roof or something.