Top Advisor Podcast Episode #81 Summary

Generational Wealth Transfer: The 100 Year Family Strategy with Josh Kanter, JD

Date: January 22, 2025
Host: Bill Cates
Guest: Josh Kanter, JD – Principal at Josh Kanter Wealth Advisory Services; Founder of Leaf Planner

Episode Overview

In this engaging episode, Bill Cates sits down with Josh Kanter, a seasoned attorney and Family Office executive, to dive deep into the challenges and strategies of transferring generational wealth. The conversation covers unique concepts such as the "100 Year Family," the importance of family meetings, and the innovative tool Leaf Planner, which helps families manage complexity and continuity. Josh candidly shares his own family’s story, including a decades-long Supreme Court tax battle, and provides advisors with actionable ideas to strengthen their value proposition and relationships with multigenerational clients.

Key Discussion Points & Insights

1. Josh Kanter’s Personal and Professional Journey

• Background and Path into Family Office Work
  • Josh started as a corporate and securities lawyer, closely involved with his family's venture capital business.
  • After his father’s cancer diagnosis, Josh left his legal practice to help navigate a massively complex estate and tax structure, including a 33-year battle with the IRS that reached the Supreme Court.
  • This hands-on experience managing family harmony, legal intricacies, and multi-generational involvement influenced his eventual shift to advising other families and creating Leaf Planner.
• Notable Quote:
  • “My hands were a little full... trying to figure out how do you keep family harmony and get multiple generations to be educated and understand all the different things that are going on.”
    — Josh Kanter [03:59]

2. Lessons from the Supreme Court Saga

• The “Quarterback” Role in Holistic Advising
  • Josh did not argue before the Supreme Court but coordinated between multiple legal specialties, balancing sometimes conflicting advice.
  • Critical insight that a holistic, "quarterback" approach is vital for success in complex family enterprise matters.
• Notable Quote:
  • "If I had followed the advice of the estate tax lawyers, we would have lost the income tax case. And if I followed the advice of the income tax lawyers, we would have lost the estate tax case."
    — Josh Kanter [07:15]

3. The 100 Year Family Concept

• Definition & Origins
  • Not Kanter’s original phrase, but underscores thinking about wealth and family continuity over generations, not just preserving money, but relationships, legacy, and purpose.
  • Draws on long-term thinking; referenced Simon Sinek’s “The Infinite Game”—“the player's time runs out, the game continues.”
• Application for Advisors
  • Encourages advisors to help client families focus not only on financial assets but also on communication, education, and values to create sustainable legacies.
• Notable Quote:
  • “It's how do you preserve the family and support a family over multiple generations... what is this going to mean to future generations?”
    — Josh Kanter [09:16]

4. The Value of Family Meetings

• Reluctance Among Advisors
  • Many advisors avoid facilitating family meetings, seeing them as fraught, time-consuming, or outside their expertise.
  • Kanter’s perspective is the opposite; he loves facilitating these meetings and views them as critical for generational continuity.
• Expertise and Outsourcing
  • Advises that not every advisor should facilitate directly, but rather, find and partner with specialists who can.
  • Emphasizes the importance of matching families with facilitators suited to their unique dynamics (therapeutic expertise for high-conflict, etc).
• Advisor Opportunity
  • Family meetings foster communication, education, and relationship-building across generations—key for client retention during wealth transfer.
• Notable Quotes:
  • “It lets me be a little bit like a therapist except I get to have an opinion.”
    — Josh Kanter [11:47]
  • "If you really want to build a relationship with that next generation, what better way is there to do it?"
    — Josh Kanter [14:11]

5. Introducing Leaf Planner: The Family Owner’s Manual

• Genesis & Purpose
  • Developed after Josh realized, even with extensive training and preparation, he was unprepared to manage his family’s complexity post his father's death.
  • Leaf Planner provides structure far beyond "In Case of Emergency" files; acts as a comprehensive owner’s manual for a family enterprise.
• Core Functions
  • Captures financial, legal, practical, relational, and educational information.
  • Designed to be the central knowledge base for the family and advisors.
  • Enables advisors to be more holistic, integrated, and valuable.
• Notable Quote:
  • “How do you go exponentially past the in case of emergency file?... How do you describe what do we do, how do we do it, why do we do it, who do we do it with?”
    — Josh Kanter [17:35]

6. Leaf Planner in Practice

• How It Works
  • A question-driven process (potentially thousands) mapping every aspect of the family enterprise—trusts, business entities, roles, responsibilities, personal details.
  • Functions like a “mind map” for family and wealth complexity.
• Criteria for Use
  • Driven by complexity, not just wealth—families with numerous trusts, properties, business entities, etc.
  • Upcoming "Complexity Calculator" tool will help advisors and clients self-assess their need.
• Advisor Differentiation
  • Sets advisors apart by offering a truly holistic, single-family office level of insight, building deep multi-generational relationships.
• Notable Quotes:
  • "It's really about taming complexity and the integrated parts. In the leaf planner context it's asking... thousands of questions."
    — Josh Kanter [23:36]
  • "There is nothing else that does this... something like Leaf Planner is going to differentiate you and is going to be a really interesting business development tool."
    — Josh Kanter [29:06]

7. Client Acquisition and Kanter’s Motivation

• How Clients Find Him
  • Receives most referrals from other advisors and industry word-of-mouth.
  • Only works with a few families each year; prioritizes fit and complementarity with existing advisors.
• What Drives Josh Kanter
  • Passion to help families avoid the confusion and conflict he experienced.
  • Desire to model hard work and purpose for his children.
  • Personal ambition to “build something”—Leaf Planner consolidates his decades of professional learning.
• Notable Quotes:
  • “My passion... I'm passionate about helping families. Whether it's through my consulting practice or Leaf Planner, the more families I can help, the more that drives me every single day.”
    — Josh Kanter [32:37]

Memorable Moments & Quotes (with Timestamps)

• “I was about as prepared as somebody could get and as educated as perfectly as somebody could get to step into this role. And yet... I realized how ill prepared I was.”
  — Josh Kanter [17:45]
• “You get an owner's manual with a toaster but not with a kid. Well, you don't get one with a family of wealth either.”
  — Josh Kanter [18:12]
• “It's complexity driven, not wealth driven... you could be worth $10 million and have a couple homes and a couple trusts ... you’re pretty complex.”
  — Josh Kanter [26:20]
• “If you really want to build a relationship with that next generation, what better way is there to do it than to think about having that deep relationship that will sustain?”
  — Josh Kanter [14:11]
• “All these things that I've done over 35 years as a professional have led me to the ability to do this and that... will help me check that box. But those are the things that probably drive me the most.”
  — Josh Kanter [33:22]

Important Segment Timestamps

• Personal Background & Family Story: [03:30]–[06:02]
• Supreme Court Case & Holistic Advising Lessons: [06:02]–[08:09]
• 100 Year Family Concept: [08:58]–[10:49]
• Family Meetings – Value & Practice: [11:39]–[16:44]
• Leaf Planner: Origins & Purpose: [17:18]–[20:15]
• Leaf Planner: Features & Criteria for Use: [23:24]–[28:28]
• Client Acquisition & What Drives Josh: [29:40]–[33:44]

Resources Mentioned

• Leaf Planner Website: leafplanner.com
  • Includes assessment tools and, by the time of release, a complexity calculator.
• Contact Josh Kanter: joshoshkanter.com
• Book Mentioned: Simon Sinek’s The Infinite Game [09:25]

Takeaways for Advisors

• Embrace the long-term, holistic approach—the "100 Year Family"—as both a philosophy and differentiator.
• Consider leveraging or partnering with family meeting facilitators to foster relationships and retention across generations.
• Complexity is often the true reason families and advisors need deeper structures like Leaf Planner—not always just asset size.
• Tools like Leaf Planner help institutionalize family knowledge, support continuity, and position advisors as indispensable, integrated partners—especially vital during the multi-trillion dollar generational wealth transfer.

This episode offers invaluable practical wisdom and inspiration for any advisor seeking to elevate their multigenerational practice and better serve families of real complexity.