How to Transfer Wealth to the Next Generation: A Guide for Modern Families

Families often struggle with how to transfer wealth effectively and responsibly. We wanted to share insights from Josh Kanter, Founder and CEO of leafplanner and CEO of Chicago Financial, a multi decade single family office.

Drawing on over 20 years of experience managing complex family enterprises, Josh shared both his family story and guidance for families who want to transfer wealth responsibly. From navigating intricate entity structures to preparing heirs for leadership, he demonstrated that true wealth planning is about building an enduring family enterprise, not just managing an investment portfolio.

We wanted to recap his key lessons so every family in our community can benefit from his expertise and start putting these principles into practice while they are still building. These principles form the foundation of transferring wealth to the next generation with clarity and alignment.

If I had known these principles in my 30s, I would have gotten to where I am so much quicker. Starting early with the right approach would have accelerated our success and strengthened the next generation from the start.
— Josh Kanter

The Problem Every Successful Family Eventually Faces

After all the effort required to build a business and grow wealth, many families assume the toughest challenges are behind them.

Wealth creation is often the easy part. The hard part is what comes next.

When the first generation begins to engage the rising generation, 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.

When his father passed, Josh took on responsibility for decades of deals, 750 tax returns a year, a complex balance sheet, long standing 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.

Passing along this separate enterprise so it thrives for generations requires education, engagement, empowerment, and the ability to uncover blind spots. It also demands a fresh approach to task management, workflow management, and thoughtful preparation for transitions.

Josh calls this Family Enterprise Thinking.

1. Redefine Wealth as a System

Traditional wealth management (Wealth 1.0) focused on diversification and returns.

Wealth 2.0 added family mission statements and values.

Wealth 3.0 is systems thinking: building a resilient enterprise that can adapt for 100 years. It’s about using financial capital to grow and support legacy, social, intellectual, and human capital.

Families that thrive across generations treat themselves as a living system, not a static portfolio.

Action Items

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 relies on one person’s knowledge. These are continuity risks.

Define your purpose.
Clarify: What is our family’s enterprise for? Security, opportunity, impact, shared experience? Write it down and communicate it.

Understand your risk.
Risk hides in people, processes, and communication. Ask:
• What breaks if a key person is unavailable tomorrow?
• What relies on unwritten knowledge?
• Where do we lack documentation or redundancy?

2. Governance Is Essential for Transferring Wealth to the Next Generation

Families need governance, just like businesses. The question is whether governance develops deliberately or accidentally.

Family governance is the way families make decisions across generations, assets, and personalities. Involving family members and advisors helps the family move from paternalism to partnership.

Action Items

Create a decision charter.
Clarify what requires consensus, what committees handle, and what is delegated to advisors.

Assign roles formally.
Executor, trustee, beneficiary, investment lead, education lead — each needs a defined scope and successor.

Install a feedback loop.
Hold quarterly or semi annual family council meetings with an agenda: Review, Reflect, Decide.

Practice purposeful transparency.
Design a transparency continuum, for example:
• Ages 18–25: mission, values, organizational map
• Ages 25–35: governance exposure, asset overviews
• 35+: full access and participation

3. Institutionalize Education and Engagement

The biggest failure point in wealth transitions isn’t taxes or investments. It’s unprepared heirs.

Families that dissipate wealth often lacked communication, trust, education, engagement, or clarity of roles and responsibilities.

Preparedness means understanding how the family enterprise works and where each person fits.

Action Items

Build a Family Owner’s Manual.
Centralize key structures, accounts, advisors, responsibilities, and governance. Include both logistics and logic.

Design next gen engagement by stage.
Stage 1: Values, philanthropy, history
Stage 2: Financial literacy and context
Stage 3: Roles, responsibilities, and active participation

Empower, don’t control.
Shift from “we’ll tell them when they’re ready” to “we’ll prepare them to be ready.”

Simulate succession.
Run an exercise: If key decision makers were gone tomorrow, what breaks first? Document the answers.

4. Plan Early for Wealth Transfer Transitions

Leading families don’t just plan who inherits; they plan how the transition happens.

That includes continuity of decision-making, information, and relationships.

Action Items

Map your critical path.
Identify the people, accounts, and documents that hold everything together. Create redundancy.

Rehearse the future.
Treat succession as a process. Run an annual simulation of a major event such as a leadership change or liquidity event.

Identify the trigger.
Choose a realistic transition event and define the key decisions and stakeholders involved.

5. Build a System to Transfer Wealth Across Generations

Complexity without structure breaks families.

Spreadsheets can help early on, but they don’t scale. Families need a system to:

• See what they own and how everything connects
• Document processes, relationships, and responsibilities
• Identify blind spots before they become crises
• Create continuity plans that work during unexpected transitions

This is why Josh created leafplanner, a digital platform that acts as the hub of family information, bringing together every moving part of the family: entities, trusts, assets, documents, people, and next gen engagement.

Ultimately, transferring wealth is not a transaction. It is stewardship.

Frequently Asked Questions

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 map their entities, roles, and responsibilities transfer wealth with far more clarity and confidence.

How do we prepare children to receive wealth responsibly?
Begin with values and purpose, then build toward financial literacy and decision-making. Prepared heirs understand the why before the what.

When should we start wealth transfer planning?
Earlier than you think. Planning while you are still building gives the next generation time to learn, ask questions, and gradually take on responsibility.

How do we reduce emotional conflict during wealth transfer?
Create governance. Define decision making processes, communication cadence, and clear roles. Families rarely struggle because of assets; they struggle because expectations were never aligned.

Closing Thought

Families that endure for 100 years don’t just protect assets. They protect alignment.

They build governance before they need it.
They teach before they transfer.
They plan while they are still building.

“It’s about long term thinking,” Josh reminded the audience. “Great leaders set up their organizations to succeed beyond their own lifetimes.”

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