05/08/2010 05:12 am ET | Updated May 25, 2011

"Can't-Lose" Business Investments

"Funny how falling feels like flying, for a little while."

- Academy Award Winner Jeff Bridges in Crazy Heart

I've been making the final edits on my upcoming book, Big Money and Why People Blow It, and came across a fascinating statistic.

A Sports Illustrated article called "How (and Why) Athletes Go Broke" noted "that only one out of 30 highest-caliber investment deals works out as advertised."

You can do better than that by playing slot machines or scratch-off lottery tickets.

If only one of out 30 of the highest-caliber deals work out, what chance does the bar your brother-in-law is dying to start have?

Like, zero.

I see this all the time. Not just from the rich and famous, but from anyone who comes into a reasonable sum of money.

There is always someone who has a "can't-miss" business idea.

And there is usually a sucker out there willing to finance it.

I knew a guy who lost his shirt as a partner in a used car lot. After it went under, he asked me what went wrong.

He was in a business he didn't know anything about, with people he didn't know very well. He had partners making the decisions and draining his bank account.

Not the way I want to handle my investments.

My friend learned from his mistake. His "second act" in business made him a millionaire.

He now runs his own show and uses his own money. He's in a business he knows backwards and forwards and doesn't have any partners.

In particular, he doesn't have "partners" who want the other "partner" to put up all the seed money.

Athletes and entertainers are natural targets. They rarely have any background or experience handling big money and often have large entourages. Also, many are adventure seekers.

They consider things like stocks, bonds, annuities and bank accounts boring. Even though boring is what they need the most.

Public figures are in the same boat as injury victims and lottery winners. They aren't going to get a second chance to earn big, big money.

If you are a professional football player, your chance to earn millions stops the day your knee blows out.

If you have a conservative nest egg waiting for you, retirement from sports is not bad. If you have your money tied up in a restaurant or the invention of the week, you had better like signing stuff at memorabilia shows since that is what you are going to be doing for the rest of your life.

I've spent 27 years in the structured settlement business and I constantly see the same dynamics that doom professional athletes and entertainers.

A person will get a settlement or judgment designed to take care of them for the rest of their lives. A greedy friend or relative (it is almost always a friend, relative, or new-found "love interest") will come up a "business idea." It's usually in a business that none of them knows about (restaurants, bars and car washes seem to pop up often) and it goes broke about 2 years later - if it lasts even that long.

The money is all gone, but the injury victim is still injured. Usually the "friends" seem to be gone, too.

I've lent money to "friends." They don't call anymore. Or write. Or send Christmas cards.

Or make any moves towards paying me back.

I guess they are no longer considered "friends."

Like my buddy who got slammed with the used car lot, I got the best education that money could buy: Experience.

Which means I won't make the same mistakes again.

I'm in a career where I had an opportunity to keep on earning at a high rate. People who get "Big Money" aren't.

The word "conservative" means to hang on to what you have.

Which is exactly the thought that should be first and always on the minds of people who get a large sum.

Don McNay, CLU, ChFC, MSFS, CSSC is one of the world's leading authorities in helping people deal with "Big Money" issues.

McNay is an award winning, syndicated financial columnist and Huffington Post Contributor.

You can read more about Don at

McNay founded McNay Settlement Group, a structured settlement and financial consulting firm, in 1983 and Kentucky Guardianship Administrators LLC in 2000. You can read more about both at

McNay has Master's Degrees from Vanderbilt and the American College and is in the Eastern Kentucky University Hall of Distinguished Alumni.

McNay has written two books. Most recent is Son of a Son of a Gambler: Winners, Losers and What to Do When You Win The Lottery

McNay is a lifetime member of the Million Dollar Round Table and has four professional designations in the financial