Have you seen Billy Madison starring Adam Sandler?  Do you remember the premise? His dad built a massive business and wanted to hand it over to his son… while Billy was busy having a full argument between shampoo and conditioner.

It’s funny because it’s exaggerated. But it also lands because there’s a real question underneath it.

What happens when something significant gets handed to someone who isn’t ready for it?

There’s a statistic that gets quoted often in our industry. Roughly 70% of wealthy families lose their wealth by the second generation, and about 90% by the third.

Not because people didn’t work hard. Not because there wasn’t enough. But because something didn’t carry forward.

So the real question isn’t just how to pass wealth on.

It’s this:

How do you prepare them for it?
How do you make sure what you built is amplified—not quietly diluted—in the next generation?

And when you’ve spent decades getting here, that question matters.

A client said something to me recently that stuck.

“We’ve spent decades building this. I’m just not sure our kids understand what it represents.”

Not from a control standpoint. From a place of respect for what it took to build it. If you step back for a moment, what you’ve built didn’t happen by accident. It took discipline, trade-offs, tough decisions that weren’t always obvious in the moment and staying steady when things were uncertain.

You earned the position you’re in. And because of that, your kids have grown up with more stability, more options and fewer constraints.

That’s something to be proud of.

At the same time, it creates a natural gap. They didn’t have to go through what you did to get here.

So it’s worth asking:

• What are they picking up from that difference?
• How do they view money, effort, and responsibility?
• Do they see this as something to build on—or something that will always be there?

Not because anything is wrong. But because they’ve had a different starting point.

And that shapes how things are interpreted.

The Real Question

The wealth didn’t just appear. It followed a way of operating.

Consistency, discipline, integrity and a willingness to do hard things over time. The ability to stay steady when others didn’t. Those weren’t side traits. They were the reason it worked.

So it’s fair to ask:

If those don’t carry forward, why would we expect the outcome to?

And if they did carry forward, what might that make possible?

Start Here

Most people have never actually defined what drove their success. They lived it, but they haven’t put clear language around it.

A simple place to begin:

Look backward.

Think about decisions you’re proud of. Not financially—personally. What did those moments have in common?

Then separate results from behavior.

The outcome isn’t the lesson. The behavior that created it is.

And make it clear. Not just “work ethic,” but what that actually looked like in your life.

If it’s clear to you, it becomes easier for someone else to understand.

And once that clarity is there, the next step becomes more practical.

Then, Over Time

This isn’t about one conversation. It’s about what gets seen and picked up along the way.

Let them see how you think through decisions. Not just what you chose, but how you got there.

Give them responsibility in ways that fit where they are. Confidence tends to follow experience.

Connect money to purpose. What it’s for, what it supports, what it doesn’t replace. And bring them along gradually. Not all at once, but not all at the end either.

Over time, that builds something more valuable than information. It builds judgment. And this is where planning starts to look a little different.

At our firm, this is part of the conversation. Not just the numbers, not just the portfolio, but how everything connects to the people behind it. Because a well-built plan isn’t just about growing assets. It’s about preparing the people those assets are meant to serve.

You

Over the next few months, pay attention to the moments where your values naturally show up. When you make a decision, when something doesn’t go as planned or when you choose the harder path.

Instead of letting those moments pass, make them visible. A quick explanation or a story when it fits. Letting them see how you think in real time. If you did that consistently, what might they begin to understand? Not just about money. But about how to operate when it matters.

If more families approached it this way, wealth would carry something more with it. Not just assets, but understanding.

We’d likely see more examples of it being built upon, not just maintained—or lost. Not because the opportunities were different, but because the people stepping into them were ready.

That’s what ultimately determines whether something lasts.

And if this is something you’ve been thinking about, give us a call.  It’s worth continuing the conversation. Because getting this right doesn’t happen by accident—and it’s too important to leave to chance.

Jeremy Heavey

AIF ® , NSSA ® | FINANCIAL ADVISOR

Securities and Investment Advisory Services offered through M Holdings Securities, Inc., a Registered Broker/Dealer and Investment Advisor, Member FINRA/SIPC. Rose Street Advisors, LLC is independently owned and operated. File #5321675

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