“Leave your children enough so they can do anything, but not enough that they can do nothing.”
— Warren Buffett
70% of wealthy families lose their wealth by the second generation, and 90% lose it by the third.
Most parents with serious wealth spend their careers obsessing over deal flow, asset allocation, and tax strategy.
Then they hand everything to their kids — and watch it disappear inside a generation or two.
This isn’t a cynical take.
It’s backed by research.
A 20-year study by the Williams Group, covering more than 3,200 families, found that 70% of wealthy families lose their wealth by the second generation, and 90% lose it by the third.
The Rockefellers are the famous exception — not the rule.
What made the Rockefeller model work wasn’t just the trusts.
It was the family governance, the conversations around money, and the structured education of every heir about values, stewardship, and purpose.
The families that keep wealth do it through intention.
The ones who lose it usually just assumed it would work itself out.
I’ve spoken with over 2,500 high-net-worth investors.
One question keeps surfacing — from surgeons, business owners, successful entrepreneurs — that has nothing to do with deal structure: How do I raise my kids around wealth without ruining them?
It’s one of the most important questions I hear.
And most parents have no real plan.
Start With Financial Education Early
One of the lowest-hanging fruits is Robert Kiyosaki’s Cashflow board game.
Designed to teach concepts of accounting, finance, and investing, the game’s core objective is to “get out of the rat race” by building passive income that exceeds expenses.
There’s even a kids’ version.
You can turn a Saturday afternoon into one of the best financial education moments your child will ever have.
I didn’t really grasp passive income until I was around 35.
Imagine what it would mean for your kids to understand it at 13.
That gap alone could change their entire financial trajectory.
Beyond games, if you have investments — talk about them.
If you have a business, bring your kids into the conversation.
Most families treat money as a taboo subject.
That silence doesn’t protect kids from entitlement; it just leaves them unprepared.
Families that maintain multi-generational wealth tend to communicate with their children in an open, direct way — detailing their intentions rather than leaving heirs to guess.
The Conversation That Most Families Skip
Here’s what I’ve seen work inside The Wealth Forum — our in-person mastermind for serious investors — and it’s not complicated: the families winning at generational wealth have defined their values around money, not just their holdings.
What does that mean in practice?
In the Hill family, we have specific conversations about what money is for, how we give, and what we believe about it.
These aren’t lectures.
They’re ongoing conversations.
Kids internalize what they observe, so if the only thing they see is consumption, consumption is what gets passed down.
Warren Buffett has a line that cuts to the heart of this.
His approach: leave your children enough so they can do anything, but not enough that they can do nothing.
That’s not just a clever quote.
It’s a framework for how to think about wealth transfer.
As you grow your assets, ask yourself: what capacity am I trying to create in my kids — not just what comfort am I handing them?
What the Rockefellers Got Right
The families that have kept wealth across generations — the Rockefellers being the most studied example — didn’t just build legal structures.
The Rockefeller dynasty trust was built around a central philosophy: educating heirs on financial literacy, philanthropy, and responsible stewardship.
The money followed the values, not the other way around.
That’s a model any family can adapt regardless of portfolio size.
Hold regular family conversations about investing.
Define what your family stands for financially.
Make wealth an ongoing topic — not a secret, not a status symbol, but a tool that serves your values.
These are exactly the conversations we dive into at The Wealth Forum — alongside deal strategy, tax planning, and investor education.
It keeps coming up because the people in the room are serious enough to ask the harder question: What does it mean to truly leave something behind?
Building wealth takes decades of discipline, hard work, and smart decisions.
Preserving it — and passing it forward with purpose — takes deliberate family culture.
If you’re not having values-based conversations around money with your kids, you’re leaving the most important part of your estate plan undone.
Our next Wealth Forum Live event is June 25–26 in Orange County, California.
If legacy, community, and serious investing conversations matter to you, check out what we have planned and come connect with us.
We’d love to have you in the room.
