insights & thought leadership

Notes on the Challenges of Wealth

Every lasting family business meets the same three questions: how to stay unified, how to preserve what matters, and how to move through change without losing each other. Families love to wander into distracting special projects — anything to avoid discussing the real issues. These are John's reflections drawn from decades spent inside family boardrooms and living rooms alike.

the Inheritance Project

Navigating the Greatest Family Wealth Transfer in History

Through the Inheritance Project, John explores the challenges of family wealth transfer, offering practical insights from decades of advising high-performing families. This unique offering provides a framework for navigating inheritance conversations with greater clarity. By optimizing outcomes, John helps families pass on their wealth and preserve family relationships.

All Posts
Family Communication
Resolving Family Conflict
Strengthening Leadership
Effective Governance
Growth & Strategy
Next-Generation
Wealth Transfer & Inheritance
Family Values

All Posts

Affluent Parenting: Building Confidence and Competence in the Next Generation

Drawing on four decades of advising high-performing families, this article explores the principles of raising capable, grounded heirs. Topics include the Seven C's of Confident Parenting, aligning parenting around shared values, sharing your family's "good struggle," avoiding entitlement and affluenza, communicating expectations and consequences, coaching the next generation through today's unique challenges, and preparing future family leaders to steward wealth with purpose

Family Communication

1 min read

Family Behaviors that Enhance or Inhibit Wealth Creation: What to Look for, What to Look Out for

Successful family enterprises are built on more than financial performance—they are sustained by healthy family behaviors. This article explores the leadership practices, governance structures, and communication strategies that strengthen family unity, foster entrepreneurial growth, prepare the next generation, and preserve wealth across generations.

Next-Generation

1 min read

The Inheritance Project

With more than $100 trillion expected to pass from one generation to the next over the coming decades, families face increasingly complex questions about the inheritance decision facing every UHNW family. Through the Inheritance Project, John guides families through a multiplicity of family issues surrounding inherited wealth, longevity, fairness, timing and more. What are other high performing families doing? John knows.

Wealth Transfer & Inheritance

1 min read

Achieving Optimal Liquidity Selling the Family Business

Family business advisor John Messervey on selling the family enterprise: navigating family dynamics, avoiding the 15 most common seller mistakes, and preparing the next generation.

Wealth Transfer & Inheritance

8 min read

Complex Family Business Succession: Why Talent and Vision Matter

Family business succession is more than a generational shift in title and responsibility. It is most often a powerful transfer of values, talent and vision. For some families it is a time of great upheaval, for others, a smooth passing of the baton. In this interview, John shares his advice on this especially challenging transition across generations.

Wealth Transfer & Inheritance

8 min read

Difficult Conversations: Eight Discussions that Every High-Performing Family Should Have

This article explores the eight essential discussions that help families navigate wealth, leadership, and legacy with greater clarity and trust. From motivating the next generation and defining the responsibilities of inherited wealth to communicating through conflict and addressing sensitive topics such as family business roles and prenuptial agreements, these practical insights are designed to help families move beyond being "stuck" and toward lasting unity and continuity.

Family Communication

2 min read

A family (two men and a woman) working together and smiling

Challenges Facing High-Performing Families

Why do even the most successful families become stuck? John explores the behaviors, conversations, and patterns that strengthen family harmony—and the obstacles that quietly undermine it.

Resolving Family Conflict

7 min read

Accelerating Wealth: Removing Family Obstacles from Wealth Creation

Sustaining wealth requires more than financial strategy—it requires removing the family obstacles that limit growth. Drawing on decades of experience advising entrepreneurial families, this article explores how unresolved conflict, ineffective governance, succession challenges, and misaligned leadership can inhibit wealth creation, while offering practical insights to help families build stronger relationships, unlock opportunity, and accelerate long-term success.

Effective Governance

8 min read

The Real Reasons Behind the Loss of Family Wealth

Family wealth is rarely lost because of markets or taxes. John examines the deeper causes of generational decline—and what enduring families do differently to preserve both wealth and relationships.

Resolving Family Conflict

8 min read

In Defense of Mediation and the Absurdity of Family Business Litigation

Conflict within family business is inevitable and perhaps even healthy. From small misunderstandings to major disagreements, what separates the long lived family business from the casualties is not just their approach, but their response to resolving differences.

Resolving Family Conflict

8 min read