I am writing a book on what I have learned by interviewing millionaires. I mentioned some conclusions of this study on Quora, a few times before. One of the things I learned right away is that some of the children of the people I interviewed had a totally different mindset: for them, hustle was not necessary and actually “looked bad”. I am actually friends with a son of a multi-millionaire in the region where I am setting a few businesses, in Portugal. His father looks like a regular John, who works his butt off, from 6am to 6pm. His son, and my friend, looks like a rich kid who got everything he wanted in life, without working for it. Hard work is good for the human soul. Many successful people hustled their way to the top, starting from nothing. For the most part, they had a huge reason to sucessed. Some had to feed their children. Some saw their parents having the worst living ever, even though they worked super hard. They raised their standards and worked hard, motivated by a big reason to succeed. They gave to their children what they never had before and as a result they became spoiled and above all, they never had a true reason to fight for a better life. In 1810, future magnate "Commodore" Vanderbilt borrowed $100 from his mother and struck out as an entrepreneur. He found success in steamboats, then built an empire in railroads. By the time of his death, Vanderbilt's net worth exceeded that of the US Treasury! His son William Henry Vanderbilt inherited most of the family fortune and doubled it by the time of his death. But that fateful third generation hit. The money was split between two of the Commodore's grandsons: Cornelius Vanderbilt II and William Kissam Vanderbilt. The latter noted, "Inherited wealth is a real handicap to happiness... It has left me with nothing to hope for, with nothing definite to seek or strive for." Houses, parties, sport, philanthropy — these came to dominate all heirs' interests. And as railroads declined in significance, there was no one left to marshal the Vanderbilts' considerable resources and connections to secure a bright future for the family's railroad-based fortune. In the mid-20th century, the great Vanderbilt houses were torn down, and while their name lives on at Vanderbilt University, the influence and prominence of the family itself has fallen out of sight almost entirely. Building a business empire is hard and very time-consuming. Bill Gates was sleeping under his desk in his office in the early days of Microsoft, for example. During this time when you don't see your family, who is taking care of the kids? Probably a babysitter who loves them but is most certainly not infusing them with work ethic, resourcefulness, perseverance and business savvy they will need to maintain or grow the vast amount of money. You can try to hire advisors, set up trusts and make “dead man” provisions in your will to control the money even after you're gone. But, those kids now are like fat little penguins and are super vulnerable. There isn't enough money in the world that cannot be pissed away by a dedicated heir. So, the only way to overcome this, is to raise kids as a business project with the specific goal to give them skills and character traits to maintain the fortune And grandkids. It's not easy!