I told an entrepreneur friend of mine goodbye the other day. It was a sad moment since he and I often talked business together.

My friend didn't die or anything. He left for South America, where he has been invited to spend three years in church service. He is off to be entrepreneurial in another way.

Our parting was sad because he didn't take my advice about how to manage his business and money affairs. Yeah, I know - nobody likes to be told what to do in such matters. But in this case, I knew what I was talking about.

He owns a business that he figures is worth at least $10 million - and it may be worth even more. The trick is finding someone who will pay what the business is worth.

My friend had no problem finding someone who would buy it. The challenge came in negotiating the financial territory between what he felt it was worth and what someone else was willing to pay for it. His best offer was $7 million cash. The buyer knew my friend's business well, had the money and was excited to buy it and take over the complete operation. The sale would free my friend from the business and would solve his money worries for the rest of his life. But could I get my friend to accept the offer?

"No way, Jose," my friend said in his newly adopted language. "It is worth $10 million, and I am not selling it for a peso less."

I used every sales closing technique I have mastered during the past 35 years of business, but I still couldn't get him to "just say yes." Instead, he put the business in the hands of some of his employees, who will manage the business in his absence.

So what's the problem?

Well for me, I would much rather leave for three years with the remains of $7 million (after taxes) in the bank than have a $10 million asset that can be destroyed very easily by inexperienced management, changes in the industry, embezzlements or a dozen other unexpected calamities. Why leave with worries when you could be worry-free?

What is the difference between $7 million and $10 million anyway? How is his life going to be different whether he has $7 million or $10 million? You can only drive so many cars, have so many homes and go on so many cruises.

Furthermore, he may well not have either when he gets back. Leave an entrepreneurial venture in the hands of the wrong people and one could return to a business disaster.

And just a few months ago, President Bush made the decision even easier when he signed the new tax bill regarding capital gains. With that change, my friend would have picked up a tax savings of $350,000 or more, and with tools such as charitable remainder trusts, he could have structured the sale to be a non-taxable event.

But you know entrepreneurs. Sometimes they just won't listen. They are strong-minded and always think they are right (which they often are, or they wouldn't have valuable companies to sell).

Still, I think they need to listen to Kenny Rogers' "The Gambler": "You got to know when to hold 'em, know when to fold 'em, know when to walk away, and know when to run."

Seems like my friend is trying to hold them and walk away at the same time. Seems to me that is a real gamble!