There’s a saying that goes: “Shirtsleeves to shirtsleeves in three generations.”

It means the first generation builds the wealth, the second preserves it, and by the third — it’s gone. Sadly, history backs this up. Families like the Vanderbilts went from being among the richest in the world to leaving little more than a famous name.

But here’s the truth: losing wealth isn’t inevitable. It happens when families forget what built it in the first place — education, communication, and stewardship.

It’s Not About the Money — It’s About the Mindset

Generational wealth isn’t just about dollars. It’s about values, habits, and understanding. I see it most clearly in farming families. Grandpa works hard, makes sacrifices, and builds something incredible. His children — generation two — watch those sacrifices firsthand. They learn by seeing the struggle and the discipline it takes to succeed.

But by generation three, the story starts to change. They didn’t see the stress, the sleepless nights, or the tough decisions. They only see the results — the farm, the business, the lifestyle. Without education and context, it’s easy to lose appreciation for what built the wealth. And once that understanding is lost, so is the legacy.

The Education Gap

The biggest reason families lose wealth isn’t bad luck or bad markets — it’s a lack of education. If you hand someone money without teaching them how to manage it, protect it, or grow it, you set them up for failure. But when every generation is taught why the family’s wealth exists and how to be a good steward of it, everything changes.

That’s why regular family meetings about money matter. That’s why we teach our kids where the wealth came from — not just how to spend it. And that’s why financial literacy within the family is just as important as the financial strategy itself.

Learning from History: Rockefellers vs. Vanderbilts

The Rockefellers and Vanderbilts started with similar fortunes. One family’s legacy faded; the other still thrives generations later. The difference? The Rockefellers treated their wealth like a family enterprise. They established education systems, meetings, and structures to ensure each generation understood their role as stewards, not spenders. You don’t have to be a Rockefeller to build that kind of structure. You just have to start with intention — and a system.

Family Banking: The Key to Long-Term Legacy

One of the most powerful ways to preserve and grow wealth across generations is through family banking. Instead of sending your dollars away to traditional banks, you create a private banking system that your family controls. That means when someone in the family needs capital for a business, investment, or farm equipment, they borrow from the family — and repay it with interest, keeping the wealth circulating internally.

Family banking creates accountability, structure, and ownership — the same principles that built the wealth in the first place.

Legacy Starts Now

Generational success doesn’t begin with the third generation — it starts today. It starts with education. It starts with systems. And it starts with someone in the family choosing to lead with intention. Whether it’s setting up a family trust, hosting family financial meetings, or building your own family banking system, you can create a legacy that lasts for generations — not just years.


Ready to Build a Legacy That Lasts?

If you want to learn how family banking can preserve and multiply your family’s wealth, let’s talk.
Together, we can design a system that keeps your legacy strong, your family united, and your wealth working for generations to come.

👉 Schedule a conversation with Wade Borth today.

Learn how time, money, and purpose is paramount in securing your financial future.