My boss wants me to become a partner in his business. But his financial advice worries me.?

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... show more 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?
Update: 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... show more 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.
Update 2: P.S. My Home Equity Loan to consolidate debt is a long story. It was not due to my own irresponsibility. I had 3 heart attacks by my 25th birthday, and needed to make a life style change to save my life. I changed careers after a very successful 9-year career in Healthcare IT Management, to pursue a less... show more P.S. My Home Equity Loan to consolidate debt is a long story. It was not due to my own irresponsibility. I had 3 heart attacks by my 25th birthday, and needed to make a life style change to save my life. I changed careers after a very successful 9-year career in Healthcare IT Management, to pursue a less stressful, more active career in construction. To finance this, I built a basement in my house and took on 3 roommates so that - while I search for a new career - even if I am in between jobs, I will always be able to pay the mortgage / keep my house. It put me in debt quite a bit, but it is the "insurance" for my home for the career change that saved my life, quite literally. I bought the house when I was only 20; I'm 27 now and have around $125,000 in equity in it and no MIP.
Update 3: RE: By the way, if he's paying you under the table, does that mean you have unreported income also? Doesn't that put you in the same boat with him as far as not paying taxes, etc. Just a thought. I plan to report my income. I even report my roommate income. I anticipate and save for a hefty tax bill at... show more RE: By the way, if he's paying you under the table, does that mean you have unreported income also? Doesn't that put you in the same boat with him as far as not paying taxes, etc. Just a thought.

I plan to report my income. I even report my roommate income. I anticipate and save for a hefty tax bill at the end of the year.

RE: And, if you do report the income, you are letting the IRS know about this guy - so you're sort of in a no win situation.

I have thought about this as well. I guess I should have a talk with him.
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