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Reggie Vanderbilt was born into a family of bitter feuds, fragile egos, and impossible expectations. Everything went downhill from there. When Reggie’s great-grandfather, Cornelius “Commodore” Vanderbilt died in 1877, the New York Daily Tribune wrote an editorial predicting the legacy of the world’s richest man: The Vanderbilt case is an impressive lesson in the folly of attempting to “found a family” upon no better basis than the possession of money. The ruling idea of the Old Commodore’s latter years was to amass a huge fortune which should stand for generations as a monument to the name of Vanderbilt, and make the head of the house a permanent power in American society. There is no country in the world where fortunes are made so quickly … and none in which inherited money has done so little for its possessors. The Vanderbilt money is certainly bringing no happiness and no greatness to its present claimants, and we have little doubt that in the course of a few years, it will go the way of most American fortunes; a multitude of heirs will have the spending of it, and it will be absorbed in the vast circulating system of the country. The plans of the dead railway king will come to naught; and if he ever revisits the earth to look after what he had so much at heart in his last years, he will be satisfied that the art of founding a family was one of the things that he did not know. This harsh opinion underestimated what was to come. Cornelius Vanderbilt left his heirs the inflation-adjusted equivalent of something like $300 billion. Within 50 years it was gone. In between sat three generations whose primary purpose was to compete on who could build the largest house and marry the bluest blood. The first heirs had some entrepreneurial sense of running the family business; over time the “family business” became insecurity and resentment. In 1875 an op-ed said socialites “devote themselves to pleasure regardless of expense.” A Vanderbilt responded that actually they “devote themselves to expense regardless of pleasure.” It was a game that couldn’t be won, so everyone lost. Reggie was one of the last Vanderbilts to inherit significant wealth. On his 21st birthday he received $12.5 million, or about $350 million in today’s dollars. Family biographer Arther Vanderbilt writes: Self-indulgent, lazy, lackadaisical, Reggie had absolutely no sense of responsibility or purpose other than to keep himself from being bored … [he was] never employed and never did a lick of work. Somewhat at a loss when asked his occupation, he usually responded, ‘Gentleman.’ … The only way Reggie could distinguish himself was to live the life of a rich playboy. And this he did with dedication and consummate skill. Reggie’s two loves were brandy and gambling. The first left him dead at age 45, with cirrhosis so severe the blood flow from his liver was cut off and pushed up to his esophagus, where the veins abruptly ruptured and left him choking in a pool of blood. The latter left him broke – after repaying debts Reggie’s will was nearly irrelevant, as he had nowhere near the amount of money promised to his heirs. Reggie’s grandson – Anderson Cooper – was one of the first Vanderbilts who was never promised dynastic wealth. It may have been a blessing. Cooper once said of inheritance: “I think it’s an initiative sucker. I think it’s a curse. From the time I was growing up, if I felt like there was some pot of gold waiting for me, I don’t know if I would have been so motivated.” It’s like he was the first Vanderbilt to be set free. – Money is fungible in the sense that my dollar bill is indistinguishable from your dollar bill. But the value people get out of a dollar varies wildly, even among people with the same income and net worth. I’m always interested in the difference between getting rich and staying rich. They are completely different things, and many of those skilled at the former fail at the latter. Part of this topic is knowing the difference between rich and wealthy. These definitions are my own, but here’s the distinction: Rich means you have cash to buy stuff. Wealth means you have unspent savings and investments that provide some level of intangible and lasting pleasure – independence, autonomy, controlling your time, and doing what you want to do, when you want to do it, with whom you want to do it with, for as long as you want to do it for. What I find fascinating are stories like the Vanderbilts, who were the richest people on earth but, by my definition, some of the least wealthy. Money to them was less of an asset and more of a social liability, indebting them to a status-chasing life that left most of them seemingly miserable. George Vanderbilt spent six years building the 135,000-square-foot Biltmore house – with 40 master bedrooms and a full-time staff of nearly 400 – but allegedly spent little time there because it was “utterly unaddressed to any possible arrangement of life.” The house nevertheless cost so much to maintain it nearly ruined Vanderbilt. Ninety percent of the land was sold off to pay tax debts, and the house was turned into a tourist attraction. There are so many similar stories from the Vanderbilt family that you begin to ask, “What was the point?” The point, as the New York Daily Tribune realized early on, was not to live a great life. It was to be rich – to be valued “upon no better basis than the possession of money.” Rather than using money to build a life, their life was built around money; rather than an asset, their inheritance was an insurmountable lifestyle debt, passed to the next generation until there was mercifully nothing left. In his 1903 book The Quest for the Simple Life, William Dawson writes: The thing that is least perceived about wealth is that all pleasure in money ends at the point where economy becomes unnecessary. The man who can buy anything he covets, without any consultation with his banker, values nothing that he buys. Nassim Taleb echoes a similar point when he says, “The record shows that, for society, the richer we become, the harder it is to live within our means. Abundance is harder for us to handle than scarcity.” You become a victim of your own success. The Vanderbilts are an extreme example, but I think they were just a magnified version of what so many regular people deal with today. Average household incomes adjusted for inflation have more than doubled in the last 70 years, but it doesn’t feel that way because expectations have more than doubled. Part of the reason home affordability is lower today than in previous generations is because the average new home is a third larger than it used to be; millions of Americans haven’t saved enough to retire, but just a few generations ago the entire concept of retirement was a dream. I want to be rich, because I like nice stuff. But what I value far more is to be wealthy, because I think independence is one of the only ways money can make you happier. The trick is realizing that the only way to maintain independence is if your appetite for stuff – including status – can be satiated. The goalpost has to stop moving; the expectations have to remain in check. Otherwise money has a tendency to be a liability masquerading as an asset, controlling you more than you use it to live a better life.

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