A: The first thing you need to do, Jeff, is determine if this money would be offered to your son in form of a gift, loan or investment. The very wording of your question tells me that you have not yet made that all-important distinction.

It sounds like your wife wants to make a gift of money, expecting nothing in return but undying love of her last born son.

You, on other hand, don't know if you should offer money as a loan (should I loan him money) or as an investment (worried that my investment will be lost).

Until you can make that distinction, your money should remain in bank.

I have a very simple rule when it comes to loaning money to relatives: NEVER, EVER loan money to anyone you might have to sit next to at Thanksgiving dinner.

"Son, pass me that dressing and tell everybody story of how you blew your old dad's retirement money..."

A loan from a relative is no different than a loan from a bank. You, Mr. Banker, are giving your son, Mr. Borrower, use of your money for a specific period of time and you fully expect loan to be paid back under specific terms, even if his business goes south. Sure, you will probably be a little more forgiving than a bank when loan goes unpaid, but damage to your personal relationship could be extreme and hard to repair.

A: Gene, I hope that I have never given anyone impression that having your own business is a walk in park. To contrary, I'm like proverbial Chicken Little when it comes to warning readers of obstacles and pitfalls that await those considering entrepreneurial plunge.

To quote myself from a column I wrote earlier this year, "If it was easy, my friend, everybody would do it."

Just to make sure we're in agreement, let me reiterate standard warnings once again. Starting a business is incredibly hard work. It takes long hours and deep pockets. It demands unbridled passion and unquestioned commitment. It requires that you give of yourself until you often feel there is nothing left to give. And sometimes, even after you've done all that you can do and given all that you can give, business fails.

Period.

Blood, sweat, and tears can only carry you so far in business world. Good intentions and grand ideas won't pay office rent. You can not make payroll with Monopoly money.

I certainly don't mean to make light of your situation. In fact, I know exactly how you feel. I failed so miserably my first time in business that I swore I would never think about working for myself again. All I wanted to do was to find a nice, secure 9-to-5 job that provided me with a nice steady paycheck. I yearned for opportunity to grow fat and happy on someone else's payroll for a change.

I never again wanted to have to think about customers or employees or withholding taxes or accounts receivable or anything else even remotely associated with being in business.

I just wanted to crawl in a hole and die because my business had failed, and in my All-American, macho male, "you are what you do" brain that meant that I was a failure, too.

Getting over failure of a business can be extremely difficult, especially if you are one of those entrepreneurs (like I was) who wrongly relates success or failure of a business to success or failure of you as a person.