In a recent episode of The Growth Capital Podcast, Josh Kanter, founder and CEO of leafplanner, joins host Justin Dixon to explore the nuanced challenges of managing wealth across generations—and the intentional strategies that can help families preserve and grow their legacies.
The conversation opens with a familiar phrase: “You get an owner’s manual with a toaster, but not with a kid.” Josh expands on this concept, pointing out that families of wealth often inherit even more complexity—but are rarely given the tools to navigate it. That realization inspired the founding of leafplanner, a platform designed to act as a family-facing “owner’s manual” that brings clarity, structure, and continuity to the often-fragmented world of family wealth.
Why Families of Wealth Need Their Own Owner’s Manual
Josh and Justin discuss how leafplanner fills a unique gap in the private wealth landscape. While there are countless tools for data aggregation, portfolio reporting, and investment tracking, those systems often miss the most important elements of legacy building: people, relationships, knowledge transfer, and family governance.
leafplanner doesn’t replace those systems—it complements them. By organizing critical information, clarifying roles and responsibilities, and connecting the dots across a family’s full ecosystem of advisors, fiduciaries, and assets, Leafplanner helps families operate with the alignment and clarity often reserved for formal family offices.
Designed for Families Across the Wealth Spectrum
Importantly, this episode highlights how leafplanner serves not just established family offices, but families across the wealth continuum. Whether a family is newly navigating complexity or well into a multigenerational journey, leafplanner is built to scale with their needs. It enables intentional planning, communication, and education—key elements in avoiding the common pitfalls that cause wealth and family harmony to erode over time.
From Corporate Law to Entrepreneurship
Josh also opens up about his own career path—from corporate lawyer to venture capitalist to single-family office principal—before launching leafplanner later in life. Justin probes into the lessons Josh carried from those experiences and how they shaped his approach as a first-time founder. His reflections provide insight not only into leafplanner's origins, but also into the mindset required to solve real problems for complex families.
Personal Reflections
As is tradition on The Growth Capital Podcast, Justin wraps up with a few personal questions. Josh shares that Pillars of the Earth is a favorite book, and How I Built This is his go-to podcast for inspiration. When he’s not building leafplanner, his favorite way to spend time is anything involving his family and dogs—and his favorite vacation spot is the serene beaches of Great Abaco.
Listen to the Full Episode
This episode is a valuable listen for family office professionals, advisors, and high-net-worth families alike. It’s a thoughtful discussion on how legacy, leadership, and long-term thinking come together to shape the future of wealth stewardship.
