Preserving Generational Wealth With Josh Kanter of Leaf Planner: The Missing Piece Isn’t Paperwork
2.2.2026
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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.
https://www.youtube.com/live/hCA_R52ZyrQ
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.
The Questions No One Can Answer After Dad DiesWhy Preserving Generational Wealth Requires More Than PaperworkPreserving generational wealth starts with the real erosion riskPreserving generational wealth means planning is dynamic, not a “final destination”Family governance and family wealth communication are the foundationHow to prevent generational wealth erosion with a “transparency continuum”How to talk to your kids about family wealth without creating entitlementWhat is a family office and do I need oneLeaf Planner: a family office portal built for real life, not just deathHow to organize estate planning documents for heirs without losing the storyPreserving generational wealth requires planning for advisor transitions tooA practical checklist for wealth transfer communicationPreserving generational wealth begins hereThe Real Way to Preserve Generational WealthListen to the Full Episode With Josh Kanter (Leaf Planner)Book A Strategy CallFAQ How do you prevent generational wealth erosion?When should you tell your kids your net worth?What is a family office and do I need one?How do you organize estate planning documents for heirs?How do you talk to your kids about family wealth?What is Leaf Planner?
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.
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