Lessons from Living the Problem: Josh Kanter on Family Complexity, Legacy, and Leadership
High-net-worth families often talk about legacy, succession, and wealth planning, but few have truly lived the problem. Josh Kanter, founder of leafplanner, has. Growing up in a family led by a world-renowned tax lawyer and venture capitalist, Josh learned early that wealth brings not just opportunity, but extraordinary complexity.
We were filing 750 tax returns a year for our family alone. When my father died, I realized, even as a trained lawyer, I was unprepared for what it would take to hold it all together.
It was during the 18 months he spent with his father after a cancer diagnosis that Josh saw the challenge, and the opportunity, clearly. He had firsthand insight into the intricate, multi-generational systems that shape family wealth. But more than finances, he learned the emotional and relational lessons that come with guiding a family through high stakes.
Growing Up in the Shadow of a Giant
Josh’s father was an extraordinary figure in law and finance, and growing up in that shadow was both inspiring and intimidating. “You see these giants, and it gives you an unrealistic perspective of what you should be, what you should achieve,” Josh says. That environment shaped his sense of self-doubt, but it also instilled rigor, discipline, and a sense of responsibility that he carries to this day.
From Doubt to Trust
Doubt, Josh admits, was constant, especially when the idea for leafplanner first came up. Turning a family insight into a platform felt overwhelming. “I doubted myself every second,” he says. The turning point came through trust: trusting his own judgment, trusting his instincts, and trusting the people around him.
I’ve learned I don’t know everything. Surrounding yourself with smart people who have been there and done that is not just helpful, it’s essential.
For HNW families, this lesson extends beyond business. Delegating, trusting advisors, and empowering the next generation are as much about relationship management as wealth management.
Avoiding Mission Creep
One of Josh’s clearest lessons is the danger of chasing every opportunity. It’s tempting to expand too quickly or pursue every appealing idea, but clarity of focus matters.
You can’t say yes to everything and still deliver your core value, he reflects.
Families face a similar challenge. Keeping priorities aligned, knowing when to say no, and protecting the family’s core vision and values are critical to long-term success.
Passing on Values and Understanding Legacy
For Josh, legacy is not just financial, it’s about values. Education, philanthropy, kindness, and contribution are what he hopes to pass on to his children and future generations.
Life is limited. We’re leaving this life to the next generation. My kids are my inspiration.
His pride in the next generation is palpable: cousins who are engaged, responsible, and thoughtful, carrying forward the lessons instilled by their grandparents.
Lessons from a Life Lived Fully
Josh’s story is also a testament to lifelong learning. Law school, corporate law, venture capital, family offices, each chapter taught him critical skills, from analytical thinking to emotional intelligence. Yet he notes that the most profound lessons often come from life itself: being present with family, making decisions under pressure, and balancing leadership with humility.
Industry Trends Families Should Note
The landscape of multi-generational wealth is changing. Transparency and education are becoming essential. Josh observes a clear shift: families now prioritize understanding relational dynamics, preparing rising generations, and fostering communication to avoid conflicts that can arise from opaque decisions.
You don’t end up in the newspapers because of 10 more basis points. You end up there because family members didn’t understand why decisions were made.
Why Families Should Listen
Josh Kanter’s story is more than a founder’s journey. It’s a window into the realities that wealthy families face every day: complexity, succession, trust, and legacy. His insights illuminate not just how to manage wealth, but how to do so in a way that strengthens relationships, passes on values, and inspires the next generation.
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