Preserving Generational Wealth With Josh Kanter of Leaf Planner: The Missing Piece Isn’t Paperwork

The Questions No One Can Answer After Dad Dies

A man spends his life building a sophisticated estate plan—brilliant strategies, impeccable legal work, a network of trusted advisors, and layers upon layers of entities. His son is a lawyer. He even gets 18 months to prepare before his father passes.

And yet, within days of his death, people start asking questions he can’t answer.

That story belongs to Josh Kanter, founder of Leaf Planner—and it’s exactly why Bruce and I wanted to bring him to The Money Advantage Podcast. Because if a prepared, trained, deeply involved son can still feel “in the dark,” what does that mean for the rest of the family?

That’s where preserving generational wealth gets real.

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Why Preserving Generational Wealth Requires More Than Paperwork

In this blog (and podcast), we’re talking about preserving generational wealth in a way most families never hear about. Not just the legal structures. Not just the investments. Not just the “where are the documents?”

We’re talking about the part that causes the most damage when it’s missing: communication, context, and continuity.

You’ll walk away with:

• A practical view of why family wealth communication matters as much as financial strategy
• A healthier way to think about transparency with kids (hint: it’s not “tell them everything” or “tell them nothing”)
• A simple framework for preventing generational wealth erosion
• A clear explanation of what Leaf Planner is and why it’s different from a spreadsheet or document vault

And yes—if preserving generational wealth is your goal, you’ll see why the “why” behind your plan may be the most valuable asset you pass down.

Preserving generational wealth starts with the real erosion risk

Bruce said something on the show that cuts straight to the heart of the issue:

If you’re going to have generational wealth, you have to make sure there’s no erosion to that wealth.

Most people assume erosion is mainly taxes, market losses, or poor returns. Those matter. But what surprises families is how often the real erosion comes from people—especially family members—who don’t have shared understanding, shared language, and shared purpose.

You can have the best legal instruments in the world and still lose your family unity.

Josh’s experience in the family office world (and inside his own multi-branch family) reinforced this: documents alone don’t preserve families. And if the family fractures, the wealth typically follows.

That’s why preserving generational wealth is never only financial—it’s relational.

Preserving generational wealth means planning is dynamic, not a “final destination”

Bruce also brought up another critical point: families often treat planning like you “arrive.”

But wealth planning isn’t a one-and-done event. It’s a living system.

Your assets change.
Your family changes.
Your kids grow up.
Advisors retire.
Health shifts.
Life happens.

Preserving generational wealth requires ongoing communication—especially before crisis hits—so your family has the muscle memory to navigate pressure without panic.

Josh shared a line that stuck with me: don’t make decisions at dusk—when you think you can see, but you can’t. That’s what crisis does. It blurs judgment.

So the goal is to practice communication in times of calm—so your family can function in times of stress.

Family governance and family wealth communication are the foundation

When Bruce asked Josh to boil it down—what’s the one thing families must cover to avoid erosion—Josh answered with something many people don’t expect:

Communication.

And not just “let’s have a meeting.”

He was talking about family wealth communication that includes:

• Values
• Shared purpose
• Decision-making norms
• Conflict navigation
• Role clarity (who is speaking as parent vs co-owner vs trustee vs sibling)

He told a story from Jay Hughes about “switching hats.” In one moment, you might be the boss. In another, you’re dad. Families get in trouble when they don’t know which role is driving the conversation.

That’s family governance in practice—how a family makes decisions together, especially when money and relationships overlap.

If you want to preserve wealth across generations, you can’t ignore how your family communicates. Because the biggest “risk” isn’t the market.

It’s misunderstanding that turns into resentment.

It’s silence that turns into assumptions.

It’s a lack of clarity that turns into conflict.

How to prevent generational wealth erosion with a “transparency continuum”

One of the most helpful concepts Josh shared was what he called a transparency continuum.

Most parents ask, “When should we tell the kids what the balance sheet is?”

As if transparency is a binary choice:

• Show everything
• Show nothing

Josh pushed back: transparency isn’t binary. It’s a continuum.

Here’s what that means in real life:

You can teach values before numbers.
You can teach decision-making before net worth.
You can teach stewardship before statements.

And when families do that, the “numbers conversation” becomes far less emotionally charged—because the kids already understand the principles.

I loved this because it connects so closely with what we teach: you don’t start with a trust. You start with meaning.

If your kids don’t know why your family does what it does, a pile of assets will never feel like a blessing. It will feel like confusion—or worse, a weapon.

How to talk to your kids about family wealth without creating entitlement

This is where preserving generational wealth becomes deeply practical.

Josh shared a personal example: he and his wife make significant annual gifts to their kids (in their 20s), and he has zero hesitation that they’ll handle it wisely.

Why?

Because they’ve been having these conversations for years.

That’s the entire point of the transparency continuum: you prepare long before you transfer.

If you want your kids to steward wealth well, start by inviting them into responsibility early:

• household contribution
• work ethic
• saving
• generosity
• delayed gratification
• clear expectations

Then, over time, you build their capacity for larger stewardship.

What is a family office and do I need one

Josh offered a definition that’s refreshing and accessible: if you have wealth that could become multi-generational, you’re functioning like a family office—at some level—because coordination matters.

Most families don’t need a traditional single-family office.

But many families do need a family office model:

• Someone coordinating the moving pieces
• A system to organize documents, accounts, entities, advisors, and responsibilities
• A way to reduce dependency on “the hub” person who knows everything

Because here’s what Josh saw after his father died:

Information was either everywhere or nowhere.

That’s what happens when everything lives in one person’s brain, one email inbox, one file cabinet, one assistant, one advisor relationship.

And that’s exactly where preserving generational wealth becomes fragile.

Leaf Planner: a family office portal built for real life, not just death

At this point in the conversation, I asked Josh to explain Leaf Planner—because many families have heard of tools that store documents or list accounts.

He acknowledged those tools and even named examples like spreadsheets, Box/Dropbox/Drive, and other organizers.

But he explained what Leaf Planner aims to do differently:

Not just store information—map it.

Leaf Planner is designed like a living “mind map” of a family’s world:

• entities
• trusts
• assets
• advisors
• insurance
• properties
• responsibilities
• tasks
• stories
• the “why” behind decisions

It answers questions families don’t realize they’ll have until they’re in the moment:

• Why did mom pick Bruce as trustee?
• Why is Rachel the trust protector?
• Where is the fine art insurance?
• Which auction house relationship matters if we sell?
• Which advisor touches which decision?
• What happens if the 80-year-old lawyer retires?

This is the difference between a document vault and a family office portal.

A vault says, “Here are the documents.”

A portal says, “Here is how the whole system connects—and why.”

How to organize estate planning documents for heirs without losing the story

Josh shared something that matters deeply: it’s not only about preserving wealth.

It’s about preserving family.

He said families don’t end up in the news because they missed 10 basis points of performance.

They end up there because siblings sue each other.

And often the root is simple: they didn’t understand what mom and dad did and why they did it.

Leaf Planner helps families document that context:

• Why were roles assigned unevenly (POA, healthcare proxy, trustee, etc)
• How decisions connect to values
• What stories sit behind long-standing assets

He gave an example of a family receiving an annual check from a hotel relationship that dates back decades. The check matters—but the story matters more. The story is what turns “money showing up” into identity, meaning, and continuity.

That’s legacy planning—not just financial planning.

Preserving generational wealth requires planning for advisor transitions too

One of the most overlooked risks Josh mentioned is this:

Families plan for “what if mom and dad die,” but they rarely plan for “what if a key advisor disappears.”

He shared that his family had an independent trustee for 53 years—an unusually long relationship. When that trustee became ill, Leaf Planner allowed Josh to quickly audit everything that person touched, across decades.

If you’re serious about preserving generational wealth, you need a plan for:

• advisor retirement
• trustee changes
• key staff leaving
• shifting responsibilities inside the home

Because continuity breaks when knowledge walks out the door.

A practical checklist for wealth transfer communication

If you want an immediate starting point, here’s a simple “do this next” checklist based on the conversation:

Preserving generational wealth begins here

1. Identify the “hub” person
   Who holds the knowledge right now? You? Your spouse? An assistant? An advisor?
2. Document the “why,” not just the “what”
   For every major decision (trusts, roles, entities), capture the reason.
3. Create a family governance rhythm
   Regular family meetings in calm seasons build communication capacity.
4. Teach stewardship before disclosures
   Start with values, contribution, decision-making—then graduate to numbers.
5. Build a continuity map
   List advisors, responsibilities, accounts, documents, and where things live.

This is how you reduce “information everywhere or nowhere.”

This is how you reduce drama after death.

This is how you preserve family unity—and protect the wealth from relational erosion.

The Real Way to Preserve Generational Wealth

Preserving generational wealth is not mainly an investment problem.

It’s a clarity problem.

It’s a communication problem.

It’s a continuity problem.

Josh Kanter’s story is proof: even high preparation and excellent legal work can still leave a family without enough context to navigate the next chapter.

Bruce and I want more for you than “good paperwork.”

We want you to build a family system that lasts:

• where your kids understand the values behind the wealth
• where roles are clear and explained
• where decision-making is practiced
• where information is accessible
• where your legacy is more than money

Because if you preserve the wealth but lose the relationships, what did you really preserve?

Listen to the Full Episode With Josh Kanter (Leaf Planner)

If preserving generational wealth is important to you, go listen to the full episode with Josh Kanter.

In this conversation, you’ll hear:

• Why legal instruments aren’t enough on their own
• How to prevent generational wealth erosion through communication and family governance
• The idea of a transparency continuum (and why it’s better than “all or nothing”)
• How Leaf Planner functions as a living family office portal—not just a document organizer
• Why capturing the story behind decisions protects relationships, not just assets

And if you want to learn more about Josh’s work, visit Leaf Planner and explore the assessments he mentioned, or reach out to his team through their website.

Most importantly: don’t wait for crisis to build the system your family will depend on.

Preserving generational wealth starts now—while you can still explain the “why.”

Book A Strategy Call

We offer two powerful ways to help you create lasting impact:

Legacy Strategy Call – If you want to uncover your family values, mission, and vision, and create a legacy that’s about more than just money, we can guide you through the process of financial stewardship and family leadership. Save time coordinating your family’s finances while building a legacy that lasts for generations. Book a Legacy Strategy Call to learn more about how we can help.
If this stirred something in you, don’t default to the path of least resistance. The default path is expensive. It sends more of your life’s work to taxes than you ever intended.

Financial Strategy Call – Discover how Privatized Banking, alternative investments, tax-mitigation, and cash flow strategies can accelerate your time and money freedom while improving your life today. Let us show you how to align your financial resources for maximum growth and efficiency. Book a Strategy Call with our team today.

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