Roundtable Recaps

Family Enterprise Thinking & the Integrated Advisor

 Discussion led by Josh Kanter, leafplanner

The founding of leafplanner was based on Josh Kanter's own family's trust real estate. Their experience lent itself to the expertise behind leafplanner today: 

• 3 generations / 3 family branches: Josh described the family enterprise he assumed responsibility for following his father's death.
  • 750 tax returns per year: The complexity of the family's entities and investments required approximately 750 annual tax filings.
  • 10,000 pages: Josh's father's estate tax return totaled approximately 10,000 pages.
• $2,500: Despite its complexity, the estate tax return was filed with an approximately $2,500 estate tax payment and ultimately received a no-change determination.
• 33 years: The family's civil tax dispute with the IRS began in 1979 and continued until 2012, 11 years after Josh's father's death.
• 7-2 U.S. Supreme Court decision: The family ultimately prevailed in a Supreme Court decision authored by Justice Ruth Bader Ginsburg.
• 1964-1994: Josh's father underwent annual IRS audits during this period.
• 1969: Some of the family's trusts date back to this period, illustrating the long-term impact estate planning decisions can have across generations.
• 50+ years: Josh used his family's continuing economic interest connected to the Embarcadero Hyatt in San Francisco as an example of why future generations need both financial information and the story and context behind longstanding family assets.
• $250 million family / $5 million umbrella policy: Josh shared an example of a family with approximately $250 million in wealth but only $5 million in umbrella liability coverage. The example illustrated how advisors working independently can miss risks that become apparent when someone looks at the family's complete financial picture.

The Family "Owner's Manual"

Josh described a recurring problem following his father's death: the family possessed extensive financial records and legal documents, but often lacked the context explaining why decisions had been made. This led to the concept of a family owner's manual designed to answer:

• What do we do?
• How do we do it?
• Where do we do it?
• Who do we do it with?
• Why do we do it this way?

That concept ultimately became leafplanner, a platform designed to organize not only documents and financial information, but also the institutional knowledge surrounding a family's assets, entities, advisors, decisions and legacy.

Preparing Assets vs. Preparing Heirs

Josh identified a common imbalance in multigenerational planning: families and advisors devote significant resources to preparing assets, but considerably less attention to preparing heirs.

He identified three broad areas of risk:

1. Financial management
2. Blind spots and planning
3. Family and legacy

Traditional planning often concentrates heavily on tax, estate, investment and financial strategies while giving less attention to family education, communication, continuity and the preparation of future generations.

"Canvas or Cage?"

Josh encouraged advisors and families to consider whether estate planning creates a "canvas or a cage" for future generations.

A "canvas" provides structure while allowing future generations flexibility to build productive lives and respond to circumstances that the original wealth creator could not anticipate. A "cage" can result when highly restrictive planning attempts to control beneficiaries for decades or generations after the original grantor's death.

The discussion emphasized balancing technical rigor and tax efficiency with flexibility, family values and human considerations.

Family Enterprise Thinking

Josh described family enterprise thinking as a broader approach to wealth that moves beyond accumulation and investment performance.

The goal is to coordinate areas including:

• Tax and estate planning
• Business ownership and succession
• Family education
• Philanthropy
• Risk and insurance
• Recordkeeping
• Lifestyle considerations
• Governance and decision-making
• Family history, values and institutional knowledge

The Integrated Advisor

Members discussed the challenges created when attorneys, CPAs, wealth managers, trustees, insurance professionals, real estate professionals and other advisors operate independently.

Important context often exists only in an individual advisor's files or memory, making it difficult for any one professional to see the family's complete picture.

The group discussed the value of an integrated advisor approach, including:

• Improving communication among a family's professional advisors.
• Identifying risks that may not appear when advisors evaluate issues independently.
• Preserving the reasoning behind previous planning and investment decisions.
• Creating continuity when advisors, trustees or family leadership change.
• Helping future generations understand both the family's assets and the history and purpose behind them.

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