Why the Uber Rich Are Often Uber Miserable

You can outsource almost everything — except the things that matter


Jack Calhoun

3 years ago | 7 min read

Sumner Redstone died recently.

You may, or may not, be familiar with him. Redstone was one of the true business moguls of the past half-century. When he died in August at the age of 97, he was still clinging to control of his vast $40 billion media empire that includes Viacom, CBS, theater chains, production companies, and more.

All this, despite being on a feeding tube and relegated to communicating in short phrases through an iPad the last few years of his life.

There’s a lot to be fascinated about when it comes to Sumner Redstone’s storied business career. But his personal life is more interesting to me, on a philosophical level, for two reasons.

First, Redstone survived a horrific hotel fire in Boston in 1979 by climbing out of the window of his third-floor room and clinging to the sill until he was rescued.

When firefighters finally reached him, Redstone’s hand and arm were literally in flames — but still he hung on. He suffered third-degree burns over 45 percent of his body and was in surgery for 35 hours.

Second, despite that experience and all the material wealth he enjoyed, Sumner Redstone was estranged from his only son and spent much of the past two decades at war with his only daughter over control of the family media empire.

The dichotomy between these two aspects of Redstone’s life is both sad and revealing. Here was a man who had such a tenacious will to live that he literally held on to a windowsill while he was on fire. It seems to me that anyone who survived such a traumatic event — literally a near-death experience — would have gained a profound appreciation for the fragility of life and, especially, for the people he loved.

And yet, according to those who were closest to him, Sumner Redstone’s only true love in life was his company. Acquiring, divesting, conquering and vanquishing, it seems, were the only things he really enjoyed. In a 2012 interview with Larry King, Redstone said, “I have no intention of either retiring or dying.”

Oh, well.

More money, more problems

The fact that Sumner Redstone achieved so much in his business life and lost so much in his personal life is particularly instructive against the backdrop of our current business climate.

Every day, it seems, we are presented with stories about technology startups that raised tens of millions of dollars in venture funding and are being swallowed up by huge competitors for hundreds of millions. Or the unicorns that finally came to market with their IPOs and spun out a fresh new batch of overnight billionaires.

For those of us who are engaged in entrepreneurial ventures — or aspire to be — these stories become siren songs that lure us into dreams of almost limitless wealth. With so much opportunity afoot today, it’s easy to believe that no sacrifice is too great in the short run if all our wildest dreams can be fulfilled in the long run.

Setting aside the reality that about 90 percent of start-ups fail, it’s worth contemplating whether the dream of one day winning the start-up lottery is really a goal worth pursuing. Because, in my experience, the reality of that life is frequently very different from the fantasy.

I spent two decades as an investment advisor to wealthy individuals and families, and many of my clients were successful entrepreneurs. A few were wildly successful, with a nine-figure net worth.

I became friends with most of my clients; they confided in me, often revealing worries and fears they didn’t tell anyone else, sometimes even their spouses.

While it was gratifying to be their confidant, it was also eye-opening to me on a personal level — because I got to see who was happy and who wasn’t. And the biggest revelation to me was that the old cliché, “more money, more problems,” was a cliché for a reason.

With rare exception, the greater the wealth my clients had, the more problems they had — and most of them were matters of the heart, not the head. They had small armies of professionals to handle the mechanics of their vast wealth; in addition to me, they had estate planning attorneys, accountants, insurance specialists and family office managers.

But, more often than not, what they also had was division and dysfunction within their families. Adult children who’d never worked a day in their lives. In-laws who had driven a wedge between them and whole branches of their family. Siblings they hadn’t spoken to in years. All the stereotypes were there.

There was a melancholy that pervaded many of these families, a palpable sadness, because they’d lost all hope of mending fences and repairing relationships with the people they loved. Estrangement and embitterment seemed more the norm than the exception.

The Redstone family saga is one very high-profile example of this, but there are countless others. In my hometown of Atlanta, one of the city’s wealthiest and most prominent families has been waging a very public war amongst themselves for years over control of their multi-billion-dollar family conglomerate and trust funds worth hundreds of millions. The local press has been filled with tawdry stories of sex addictions, infidelity, divorces and jury trials.

Children sued parents; parents obtained injunctions against their children. Ex-wives sued ex-husbands. It all read like a day-time soap opera, but it was real, and a painful thing to observe.

Vast wealth is like fissile material

I know what you’re thinking: “Cry me a river.” And I get it. When you consider how many people in this world lack access to the most basic life necessities — food, water, shelter — it’s hard to muster up much sympathy for the .001 percent who are worth more than the GDP of some countries, yet still manage to turn their personal lives into disasters. “Just give me a chance like that,” we tell ourselves, “and I’ll show you how to handle that kind of money the right way.”

But it’s not so easy, because vast wealth is like fissile material. If properly handled, it can be a tool of great construction; if not, it becomes a destroyer with a half-life that spans generations.

The irony of having that kind of money is that it creates an urgent need to protect yourself and your family from its corrosive effects — emotionally, spiritually — at a time when the temptations and distractions it enables are overwhelming.

It becomes easy to equate “experiences” with “meaning.” Every desire can be indulged, and almost every mundane aspect of life can be outsourced — except the part where relationships are nurtured and values are instilled.

That can only be done down in the trenches of daily life, and it often gets skipped over because there are empires to run and fun to be had. It is also the only thing keeping you and your family from becoming entitled, indulgent train wrecks.

When asked about how much money he planned to leave his children in his estate, billionaire investor Warren Buffet famously said: “A wealthy person should leave his kids enough money to do anything, but not enough to do nothing.” As with most things, Buffet cuts right to the heart of the matter.

Humans are the only species on earth with a need for meaning. We are hard-wired to seek a purpose — to accomplish things. We have an innate desire to be fulfilled, not just pleasured. If you deprive someone of the need to get out of bed every day and do something meaningful, they will turn into an aimless, neurotic wanderer.

Enough money or plane money?

It was not lost on me that my clients who seemed to be the happiest were those who had accumulated enough wealth to be debt-free and live a nice lifestyle, but not so much they had more than they could ever spend. They could eat out when they wanted to, take nice trips here and there, maybe have a vacation house they loved to spend time at. They were free of debt and didn’t have to worry about paying the bills. But they still had to be prudent and manage their nest egg appropriately.

They were in what I called “the sweet spot” — enough money to live the life they enjoyed, but not so much that temptations were always knocking on their door or their kids and grandkids didn’t have to make something of themselves. Not coincidentally, their family relationships tended to be healthy and robust.

Enough, but not too much. It sounds noble, but not many of us have that as our end goal. We want the brass ring, the big payout. “Plane money” as one of my industry colleagues put it. (I never really liked him.)

Yet when I read the stories of the IPO millionaires and billionaires who are being minted almost daily, I think of my former clients, the super-wealthy ones with all the stuff and all the family problems. I wonder if these new members of that elite club are ready for that kind of wealth and all it entails. Not just the mechanical aspects of managing it, but the wisdom and restraint that’s required to keep it from ruining your family, incrementally and inexorably, over time.

I doubt they are, because I’m not sure anyone can be. And that’s the sad part. Because if you get all that money and lose the people you love along the way — what was it all about in the first place?


Created by

Jack Calhoun

20+ years as managing principal of a wealth management firm. Currently helping people make amazing BBQ through SmokeBloq, an IoT cooking thermometer.







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