No One Sets Out to Waste It
What Is Wealth For? - Week 1
Jerry and Kathy live in Minneapolis and have two grown children. When the kids were young, Jerry started a brilliant business that digitized legal records. After selling the company for more than $100 million, Jerry realized he wasn’t just a good businessman—he was also a highly talented investor.
Jerry and Kathy wanted to look out for their kids, so they generously set aside $2 million in a trust for each of them. It was enough to cover medical needs and finance their grandchildren’s college education.
Over the next few decades, Jerry’s investments grew exponentially, ballooning from $100 million to more than $500 million. And all along, he had been giving generously to charity!
But there was a quiet, creeping problem. In tandem with growing his charitable giving, Jerry kept swelling his children’s trust funds, eventually moving them from the original $2 million to more than $10 million apiece.
Because of that staggering wealth, his kids didn’t need to work—so they didn't.
They bought expansive homes, acquired boats, and spent their days traveling to exotic locations. With no need to work and an endless amount of empty time on their hands, addictions crept in. Eventually, both of their marriages crumbled.
Horrified by what was happening, Jerry tried to undo what he’d done. He went to pull the money back out of their accounts.
But legally, the assets now belonged to his kids, not him. And his adult children did not appreciate their father asking to take back "their" money.
Meanwhile, in Massachusetts, another follower of Jesus named Andrew owned a major utility company. It grew massively, and today, Andrew’s family foundation alone holds assets north of $1 billion. Across New England, prominent medical centers and university buildings bear Andrew’s last name.
But in the process of scaling that business, Andrew admits that he lost his children.
His daughter follows Jesus, but his son does not. Desperate to foster some semblance of family unity, Andrew hit on an idea: “What if each of our three families gave away one-third of the foundation’s annual proceeds as they like?”
Like many patriarchs, Andrew envisioned leaving a multi-generational legacy. He pictured his children and grandchildren gathering to distribute the fortune. In his mind, long after he passed away, they would come together annually in a beautifully paneled boardroom, or around the Christmas tree, or at a long table in a Nantucket beach house. He imagined the kind things they might say about him for providing this opportunity, the deep discussions they’d share, and how they would conclude the night by raising a toast to his memory.
Or something like that.
But Andrew’s heirs are individuals with their own free will, concerns, and distinct agendas; their God-given purpose in life is not to carry on Andrew’s legacy.
Andrew’s idea of using money to manufacture family togetherness was well-intentioned, but it failed completely.
Today, Andrew’s daughter gives to Christian operations that Andrew loves. But his son deploys his third of the foundation's grants to fund social and political causes that Andrew would actively oppose. His son doesn't even attend the meetings meant to foster family togetherness, using his time instead to advocate for initiatives that break Andrew's heart.
Jerry, Kathy, and Andrew asked to remain anonymous so they wouldn't embarrass their families, but they explicitly wanted their stories told. They told me they wish they could go back in time and give themselves one piece of advice: Focus on meeting others' needs, not feeding your kids' greed.
Outside of the Christian world, the Vanderbilt family is the textbook example of this exact trajectory.
When Cornelius Vanderbilt died in 1877, he left behind a fortune estimated at roughly $100 billion in today's dollars. His heirs immediately treated the inheritance as a social competition. They built ten separate mansions on Fifth Avenue, threw the most absurdly extravagant parties of the Gilded Age, and chased catastrophic investments.
Within just 30 years of Cornelius's death, the vast fortune was entirely squandered. By 1907, not a single member of the Vanderbilt family was among the richest people in the United States. Within 48 years, one of his direct descendants died penniless.
When 120 Vanderbilt descendants gathered at Vanderbilt University in 1973 for a family reunion, not one person in the room was even a millionaire. Anderson Cooper, a direct Vanderbilt descendant, later reflected on the “corrosive, cancerous effects” of that inherited wealth on heirs who were simply "born into it" and falsely assumed it would last forever.
The Enemy Was Never Greed. It Was Assumption.
Left to ourselves, most of us just hold onto capital. Others—like Jerry, Kathy, and Andrew—try to automate our wealth and priorities into the next generation, often with devastating results.
We have to challenge the cultural architecture around wealth. The world tells us that the money in our bank accounts belongs to us and our descendants. For tax optimization, we are told to lock it up in trusts early so it transitions seamlessly when we die, perhaps dropping the rest into a perpetual foundation to be slowly parsed out over a century.
No one sets out to waste their wealth. But because we assume that wealth automatically translates into a legacy, we default to the cultural playbook. We work, we accumulate, we optimize, and we pass it down—unwittingly setting the stage for the exact same squandering that broke Jerry's family and emptied the Vanderbilt ledger.
If we want a different outcome, we have to start with a fundamentally different set of maps for how reality and wealth actually work.
This was week 1 of this month’s series “What is Wealth For?” Next week, we unlock the blueprint: "The Three Irrational Fears Keeping Your Wealth Frozen."
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