A Tale of Two Winners

“Leo” had a good strategy for handling big paydays. Throughout his career, whenever he received a big chunk of income, the first thing he did was carve out an amount sufficient to cover the income taxes he would have to pay on it and put the money in a special bank account.

The result, of course, was invisible, because the potential problem (having to cough up an unexpected number of dollars at tax time) never became an actual problem. Leo would then set aside 90 percent of the remaining money to expand his ever-increasing financial cushion. And with the remaining 10 percent, he indulged himself and his family with whatever luxuries their hearts desired.

I don’t believe I’ve ever known anyone who planned his financial life so carefully and followed through in such a disciplined manner. Leo did, in fact, hit a string of crises in the mid-eighties that might have put most wealthy people under. But thanks to his taxes-first, cushion-second, luxuries-third approach to allocating income, he was able to weather each and every adversity.

Today, Leo lives in a $35 million oceanfront mansion in Bermuda. Prior to moving to Bermuda full-time, he sold his home in Aspen for a cool $19.75 million, which The Wall Street Journal reported to be the biggest residential real estate sale in the history of Colorado.

I guess you’d say that because of his approach to finances, Leo is the consummate financial winner. Which brings me to another friend whom I had always placed in the same category as Leo.

Jack was the epitome of success – a go-go entrepreneur, always on the move, always making deals, always enthusiastic and positive. Like Leo, he owned two magnificent homes (in Florida and Wisconsin), not to mention a fishing lodge in Panama.

Just as important, Jack was a superb human being – kind, honest, and gracious to a fault. He was one of those lucky people who possess a natural quality that makes everyone instantly like and trust them.

Back in the early eighties, Jack and I were involved in a cellular-telephone deal together, and, as one of the financial requirements for filing cellular-licensing applications, he had to submit his personal financial statement. It was an impressive $32 million – a very liquid $32 million.

As the years passed, I moved abroad and got caught up in other matters. As a result, I lost contact with Jack. I did think about him from time to time and wondered how his life was going. But those “I’ll have to give him a call sometime” thoughts never manifested themselves into reality.

I vividly recall saying to my wife on one occasion, when Jack’s name happened to come up in conversation, “Knowing what a magic touch Jack has, I wouldn’t be surprised if his $32 million net worth has grown to more than a hundred million by now.” Just the thought made me feel happy for him, because it couldn’t have happened to a nicer guy.

Recently, I received an e-mail from Jack’s youngest son, Jay, saying that his father had passed away. Jay and I subsequently spoke by phone, and what he told me nearly took my breath away.

Jack had died penniless in a nursing home. About seven years after my last contact with him, the IRS presented him with a huge tax bill that forced him to sell most of what he owned at the time, including his palatial homes.

Dementia had begun to set in, followed by a stroke, then confinement to a wheelchair. The last several years of his life, Jack couldn’t speak at all and had to be fed and cared for by a nurse.

I was touched beyond words when Jay told me about the last time he saw his father alive.

Family members had warned him that Jack was so far gone he wouldn’t even recognize his own son. But they were wrong. Though he couldn’t speak, tears rolled down Jack’s cheeks when Jay entered the room.

It is impossible for me to focus on a mental picture of Jack confined to a wheelchair, unable to speak, his brain deadened – and penniless, to boot. For me, he will always be vibrant, confident, and the picture of prosperity.

I don’t know the details of Jack’s IRS problems, but sometimes the unforeseen circumstances Fate places in our path are just too much to handle. In this regard, Jack’s sad end reminds me of the words of Baltasar Gracian, the seventeenth century Jesuit priest who cautioned, “Place your winnings under cover when they are sufficient or large. … Fortune soon tires of carrying anyone long on her shoulders.”

The words on Forrest Gump’s T-shirt put it more bluntly: “S___ happens.” And it happens so frequently that a rational person has no choice but to recognize it as an integral part of life.

What’s especially irritating about it is that no matter how smart you are, no matter how successful you may be, and no matter how carefully you plan your financial affairs, there will likely be unforeseen circumstances that will register 8.4 at your epicenter.

All anyone can do to prepare for a seismic life shock of that magnitude is never forget that Fate sits on the other side of the Table of Life, plotting her next move. Make your financial moves very carefully, and never underestimate the unforeseen circumstances that she surely has in store for you.

Overconfidence is a dangerous card to play. And arrogance is as close as one can come to playing a fatal card. It’s a good idea to operate your life on the assumption that unforeseen circumstances are lurking in the shadows, just around the next bend. Fortune does not carry anyone on her shoulders indefinitely.

You should always try to hold a clear picture in your mind of the end result you’re after. And to the degree you become adept at this skill, you’re likely to end up with a very good batting average – payable in dollars. Nevertheless, it’s all for naught if you fail to make allowances for the roadblocks that are sure to be placed in your path by that fickle trickster known to humankind as Fate.

[Ed. Note: You can learn how to keep Fortune on your side with Robert Ringer’s powerful personal-development package, The Magic of Synchronicity. In it, you’ll find out how to achieve prosperity, purpose, and peace of mind by getting all areas of your life in sync.]

Robert Ringer

Robert Ringer is a New York Times #1 bestselling author and host of the highly acclaimed Liberty Education Interview Series, which features interviews with top political, economic, and social leaders. He has appeared on Fox News, Fox Business, The Tonight Show, Today, The Dennis Miller Show, Good Morning America, The Lars Larson Show, ABC Nightline, and The Charlie Rose Show, and has been the subject of feature articles in such major publications as Time, People, The Wall Street Journal, Fortune, Barron's, and The New York Times.