How regular, little conversations set the stage for multi-generational wealth.
This piece by John Knowlton was originally published in Trusts & Estates on April 13, 2026.
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Family fortunes are hard to build, but they’re even harder to keep. We’ve all heard stories of wealth being squandered by the offspring of successful entrepreneurs. Here’s an example to refresh your memory: Cornelius Vanderbilt (1794-1877) established a 19th-century empire in shipping and railroads, which was worth an estimated $185 billion in today’s dollars. His son, William Henry Vanderbilt, doubled that fortune, but subsequent generations struggled to preserve it. Lavish spending, fragmented inheritance and a lack of financial discipline led to rapid decline. By the 1970s, none of the 120 descendants were millionaires. Grand mansions were sold or demolished, and the family’s stake in the New York Central Railroad was eventually lost. Though Gloria Vanderbilt and her son Anderson Cooper forged independent careers, the original fortune had largely dissipated, serving as a stark reminder that generational wealth requires stewardship, not just legacy. This family story is a powerful illustration of the “Shirtsleeves to shirtsleeves in three generations” proverb.
Good estate-planning documents protect assets. But good values protect beneficiaries. Your clients might not be Vanderbilts, but they’ve accumulated assets that are worth preserving. And this may be the key to making generational wealth last for generations: Transmitting family values along with family money. People who build wealth and great companies tend to focus on others’ needs. They’re sensitive to the problems of others. They’re aware of people’s desires. And they find a way to offer products, services and capital to help other people get what they want. In a free market, that approach leads to growth and financial success for the person or organization that delivers what people want and need. In his book, Hit Refresh, Satya Nadella of Microsoft says, “Innovation comes from having a deep sense of empathy for the unmet and unarticulated needs of customers.”
And to be clear, many people find financial success without being the founder or CEO of a company. Millions of managers, directors and executives work inside organizations that collectively solve problems and meet needs. As they attend staff meetings, collaborate to hit timelines and objectives or simply do good work, they’re adding value. Corporate efforts serve customers, clients or patients. And it’s this ethic that must be instilled in our clients’ children if they are to maintain the wealth their parents built.
This means that parents must be intentional about conveying values—consistently over time. The word “instilled” implies “drip by drip.” And transmitting the value of meeting people’s needs requires that parents talk about their work: what they do, how they interact in the world, who they work for and how they solve problems and meet needs. Much of our work as advisors and planners involves money: how to invest it, how to limit taxes and how to effectively pass it to the next generation. But we can serve our clients even better if we help them learn to talk and share with their kids.
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