Starting a business is never easy and odds of your success or failure are about even money. The fact is, approximately half of all small businesses fail within first four years. And a large percentage of those failures occur within first year. These are statistics that keep many entrepreneurs awake at night. Like Sisyphus, always pushing that boulder to top of hill only to have it tumble back to bottom each time, you never know when you're going to lose your grip on your business and have it tumble back over you.

OK, so far in this column I have managed to squeeze in references to modern American television and ancient Greek mythology. Enough highbrow beating around bush. Perform autopsy and learn from it. Only by knowing real reasons your business died can you identify and hopefully stave off those maladies before they take you down next time, if there is a next time. And if you're a true entrepreneur there will be a next time, trust me on this.

There are many reasons why businesses fail, but according to a recent survey by U.S. Bank, majority of business failures can be attributed to three reasons: bad management, bad financial planning, and bad marketing.

Bad management comes in many forms. The survey showed that seventy-eight percent of business failures examined were due in part to lack of a well-developed business plan and a business owner who had no business being in business he was in. In other words, business owner did not have an adequate knowledge or a thorough understanding of business he had chosen to start. This is why software entrepreneurs like me don't start shoe stores. I have feet, I wear shoes. That's not enough to qualify me to go into shoe business.

Next, seventy-three percent of business failures in survey were also manned by owners with rose colored calculators. These business owners over-estimated revenue projections (the number of expected sales) and under-estimated burn rate (the amount of money required to sustain business per month).

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.