How to Transfer Wealth to Family Responsibly: Insights From the Long Angle Retreat
Building the 100-Year Family Through Family Enterprise Thinking
Josh Kanter, Founder & CEO of leafplanner
(Presented at the Long Angle Family Retreat)
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Table of Contents
The Problem Every Successful Family Eventually Faces
Redefine Wealth as a System (The First Step in Transferring Wealth to Family)
Governance Is Essential When Transferring Wealth to the Next Generation
Institutionalize Education & Engagement (Preparing Children to Receive Wealth)
Plan Early for Wealth Transfer Transitions
Build a System to Transfer Wealth Across Generations
Conclusion
Join the Conversation
Frequently Asked Questions
The Problem Every Successful Family Eventually Faces
After all of the strenuous effort required to build a business and grow wealth, many families assume the toughest challenges are behind them.
Wealth creation is often, unfortunately, the easy part. The hard part is what comes next.
When the first generation begins to engage the rising generation, and ultimately passes the baton, families are often blindsided by the complexity they’ve accumulated, dozens of entities, multiple trusts, hundreds of accounts, and people who “know how things work” but whose knowledge isn’t documented anywhere.
Josh lived this firsthand.
Josh worked directly with his father and thought he had a grasp of their complexity. When his father passed, Josh took on responsibility for 40 years of deals, 750 tax returns a year, a complex balance sheet, a multitude of relationships, multi-decade litigation, and a family wondering, “Where is everything?”
This experience led to one conclusion:
The family itself is a system, even a business in its own right, distinct from the family business. Josh calls this the business of the family. Passing along this separate enterprise so it thrives for generations requires a new kind of management: education, engagement, empowerment, and the ability to uncover blind spots that family leaders rarely see in their operating businesses or portfolios. It also demands a fresh approach to task and workflow management, and thoughtful preparation for transitions, not just of a CEO, but of the many people who collectively make up the family enterprise.
Josh calls this Family Enterprise Thinking.
Redefine Wealth as a System (The First Step in Transferring Wealth to Family)
Traditional wealth management (Wealth 1.0) was about diversification and returns. In other words, it was all about financial capital.
Modern wealth (Wealth 2.0) added family mission statements and “values.”
But the next evolution, Wealth 3.0, is about systems thinking: building a resilient enterprise that can adapt for 100 years. Continuing to build on the concepts of Wealth 2.0, it’s about using the family’s financial capital to grow and support the family’s other capitals - its legacy, social, intellectual, and human capital.
Families that thrive across generations treat themselves as a living system, not a static portfolio.
Action Items
The first (and easiest) steps you can take to ensure you are ready, look something like this:
Audit your family enterprise. List every entity, trust, property, investment, and role on a single map. Ask: Who owns this? Who understands it? Who could operate it if I couldn’t tomorrow?
Identify dependencies. Highlight anything that depends on a single person’s knowledge, an advisor, family member, or assistant. Those are continuity risks.
Define your purpose. Ask: What is our family’s enterprise for? Is it security? Opportunity? Impact? Shared experience? Write down your “why”, it’s your family’s North Star. Many wealthy families assume their advisors and family members are on the same page. The problem is they haven’t solidified their “why”, and most likely haven’t communicated it with key stakeholders.
Understand your risk. Risk in a family system goes far beyond market volatility. It hides in people, processes, and communication. Ask yourself: What would break if a key person were unavailable tomorrow? What decisions rely on unwritten knowledge or memory? Where do we lack clarity, documentation, or redundancy?
The most resilient families view risk management as more than investment strategy, it’s enterprise continuity. Understanding where your system is fragile is the first step to making it durable.
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Governance Is Essential When Transferring Wealth to the Next Generation)
Like businesses, families need governance. But governance in a family system operates differently. Will your governance journey be deliberate or accidental?
Family enterprise thinking reframes governance as the process by which families make decisions together, across generations, assets, and personalities. Involving family members and advisors in family governance helps the family move from paternalism to partnership.
Action Items
Create a Decision Charter for Wealth Transfer.
Outline what requires consensus, what can be made by committees, and what’s delegated to advisors.Understand and Assign roles formally.
Executor, trustee, beneficiary, investment lead, family education lead. Each should have a defined scope and successor.Install a feedback loop.
Establish a quarterly or semi-annual “Family Council” meeting with an agenda: Review, Reflect, Decide. Treat it as your board meeting.Practice transparency on purpose.
Build a “Transparency Continuum.” This could be based on something as simple as age, or something more thoughtful. This is not always static, but a good starting point.
Example:
Ages 18–25 → access to the family’s mission, values, and organizational map.
Ages 25–35 → exposure to governance, asset overviews, and advisor roles.
35+ → full access and participation in decision-making.
Institutionalize Education & Engagement (Preparing Children to Receive Wealth)
When people search for how to transfer wealth to family, they often jump straight to tactics. The #1 failure point in transitions isn’t taxes or investments, it’s unprepared heirs. Families that dissipate wealth or familial relationships are often failing to create trust, to communicate effectively, to educate, to engage, to empower, to understand roles and responsibilities, etc. As you move from running the family business to running the business of the family, you are face-to-face with these staggering challenges. What can you do about it?
Families often mistake financial literacy for readiness. But real preparedness means understanding how the family enterprise operates and where they fit within it.
Action Items
Build a Family Owner’s Manual. Centralize your key structures, accounts, advisors, responsibilities, and governance in one place. Include both logistics (what exists) and logic (why it exists).
Design next-gen engagement by stage.
Stage 1: Introduce values, philanthropy, and family history.
Stage 2: Educate - financial literacy is about more than the balance sheet.
Stage 3: Define roles and responsibilities, and provide opportunities for engagement.
Empower, don’t control. Replace the paternalistic mindset: “we’ll tell them when they’re ready”, with partnership: “we’ll prepare them to be ready”.
Simulate succession. Do a tabletop exercise: If the primary decision-makers were gone tomorrow, what would break first? Document the answers.
Plan Early for Wealth Transfer Transitions
The best families don’t just have plans for who inherits, they plan for how the transition happens. That means clarifying not only estate mechanics but the continuity of decision-making, information, and relationships.
Action Items
Map your “critical path.” Identify the handful of people, accounts, or documents that hold everything together. Create redundancy. Advisors, Trustees, Partners, etc.
Document “how things work” for the next generation. Who pays which bills? Where is the master list of advisors? Who holds the passwords? This is where families most often fail.
Rehearse the future. Treat succession as a process, not an event. Hold an annual “future simulation”, leadership change, sale, or liquidity event, to surface weak points.
Identify the Trigger: Choose a realistic event, leadership change, sale, or liquidity event, based on your families’ structure and priorities.
List Key Decisions: Outline the major choices that would need to be made, such as succession appointments, fund allocations, or stakeholder approvals.
Map Stakeholders & Consequences: Determine who is involved, who needs to be informed, and potential risks or conflicts to surface during the exercise.
Build a System to Transfer Wealth Across Generations
Complexity without structure breaks families. Families’ first step usually starts in spreadsheets. This is okay to start thinking about the complexities, but it often falls short. Families need to build a system to:
See what they actually own and how it connects.
Document processes, relationships, and responsibilities.
Identify blind spots before they become crises.
Create continuity plans that work when life changes.
That’s why Josh evangelizes about family enterprise thinking, and why he created leafplanner, a digital platform that acts as the hub of family information to help you start walking through these actions, bringing together every moving part of your family: entities, trusts, assets, documents, people, and next-gen engagement.
Because ultimately, transferring wealth to family is not a transaction, it’s a system of stewardship.
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Frequently Asked Questions About Successful Business Communities Communities
Q: What is the most effective way to transfer wealth to family?
Start by looking at wealth as a system, not a balance sheet. Families who take the time to map their entities, roles, and responsibilities are far more successful at transferring wealth to the next generation with confidence and clarity.
Q: How do we prepare children to receive wealth responsibly?
Begin with education and shared values, not account balances. Introduce family history and purpose, then build toward financial literacy and decision-making. Prepared heirs understand the why before they manage the what.
Q: When should we start planning wealth transfer for our family?
Earlier than you think. Planning while you are still building gives the next generation time to learn, ask questions, and practice taking on responsibility gradually instead of inheriting everything at once.
Q: How do we reduce emotional conflict during wealth transfer?
Create governance. Define who makes which decisions, establish a communication cadence, and ensure everyone understands their role. Families rarely struggle because of assets. They struggle because expectations were never aligned.
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