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. 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 ...