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What happens when you mix an early-stage VC investor, an art collector, a legal strategist, and a family office principal with a 100-year vision?
You get the origin story of leafplanner.
Josh recently joined the Superclusters podcast with David Zhou to unpack the complexity behind generational wealth, and how most families are missing a critical component: context.
“Most people don’t plan for when shit hits the fan. For those who do, their in-case-of-emergency plan focuses on what to do, not why or how.”
On the surface, this episode is about how family offices operate. But underneath, it’s a playbook for anyone building something intended to last. Whether you're a venture-backed startup founder, a wealth creator, or the steward of your family’s legacy—Josh drops insight after insight that will challenge how you think about time, responsibility, and what truly matters.
From Art to Venture to Legacy
Josh shares his journey, starting with his passion for art (and sculptor Jun Kaneko), through his early days as a lawyer, to overseeing a complex single family office. And yes, he also touches on his family’s 33 year battle with the internal revenue service and a trip to the U.S. Supreme Court.
But the turning point came when Josh realized that the “what” wasn’t enough. The next generation wasn’t going to get the full picture just by inheriting a list of assets or a set of legal documents. What they needed was context, a guide to why decisions were made, how responsibilities were divided, and what should be prioritized.
So he built leafplanner.
More Than a Fire Drill Plan
Josh describes most estate and succession planning documents as “in-case-of-emergency files”technical, disconnected, and stripped of nuance.
“Every one of those systems [Dropbox, Box, Google Drive] relies on the brain that built the architecture of how you organize them.”
That “brain” disappears when a principal passes. And without that knowledge, the next generation is left guessing: Which fund matters more? Which asset carries sentimental weight? What relationships are worth protecting?
leafplanner was built to capture and communicate all of that. Not just the what and where, but the why and how.
Where Do You Start?
Josh doesn’t pretend this is easy. In fact, most families don’t even know where to begin. His advice?
“Start with something you can see visually in your head along with all of its connections.”
From that entry point, whether it’s a trust structure, an investment entity, or a set of values, leafplanner helps families unpack, organize, and explain their entire enterprise. And perhaps more importantly, it helps families identify their motivation.
“That’s something our team helps figure out.”
Financial Capital Is Just the Fuel
One of the most powerful takeaways from the episode is Josh’s emphasis on the five types of family capital—a framework developed by Jay Hughes and embraced at leafplanner:
- Intellectual
- Human
- Social
- Financial
- Spiritual
At leafplanner, financial capital isn’t the end goal. It’s the fuel. The point is to use it to grow the other capitals: the knowledge, people, and networks that make a family stronger over generations.
“Success is more important than my ego.”
That mindset defines how Josh operates, and how leafplanner guides families in creating a legacy built on intention, not just instructions.
Give it a listen…
