Legacy in the Small Moments: What Piccolo Pete Races Teach Us About Family Wealth

By Mike Schmitt, Rubra Group

Last week, our neighborhood in Southern California lit up the street—not with fireworks in the sky, but with fireworks on wheels. Children and grandparents, uncles and teenagers, stood along a blocked-off street cheering on toy cars strapped with Piccolo Pete fireworks, duct-taped to skateboards, store bought toys, and home made sleds zipped and whistled their way to glory (or possibly into infamy).

They call it the Piccolo Pete Races, a tradition that started, like so many good things, as a spontaneous summer idea and became a fixture, 21 years later, it’s one of those events where the stories are more important than the outcome, where everyone knows “who crashed last year” and “who taped theirs too tight.”

Last year we even got written up in Autoweek written by Mark Vaughn:  What Happens When You Duct-Tape 135 Piccolo Petes To a Skateboard

Reading Mark’s article, I couldn’t help but think: This is legacy work in its purest form.

At Family Fortune, we spend our days helping families build governance structures, succession plans, and strategic frameworks. But every so often, life reminds us that the true glue of family legacy is made in simpler, louder, sillier moments—moments like these races.

Building Legacy with Duct Tape and Laughter

Family enterprises are often advised to “think long-term.” But it’s not just about asset allocations and shareholder agreements, it’s about creating continuity between generations.

The Piccolo Pete Races do something profound without meaning to:

• They give every generation a role - from building to racing to telling the tales.

• They cement stories into the family identity - so that “fourth cousins twice removed” still feel like part of something bigger.

• And they bridge the distance between generations not with lectures, but with laughter.

There’s no entry fee, no financial payoff - just a simple, joyful act of being together, creating a shared experience that will be recalled at future weddings, memorials, and holiday tables.

Isn’t that exactly what we hope our family businesses will do?

Memory Capital and Leadership Capital: Two Sides of the Same Coin

In the Family Fortune model, we speak often about financial capital, intellectual capital, human capital, and social capital. But events like the Piccolo Pete Races remind us of two more forces at work:

Memory Capital - the stockpile of joy and belonging that keeps families close. Leadership Capital - the early, often overlooked cultivation of initiative, resilience, and healthy risk-taking.

These traditions don’t just build closeness - they train future leaders in the safest, most natural way possible.

Think about it:

• A child who designs their own racing contraption, takes a few tumbles, and improves it year after year is learning resilience.

• A teenager who organizes the next race or mentors younger cousins is practicing leadership and responsibility.

• A family member who steps up to referee, coordinate, or narrate builds confidence in public roles.

By making play a structured, recurring part of family life, we cultivate leadership muscles, people willing to take risks, handle setbacks, and show up for others. These are the very traits required to steward enterprises, manage transitions, and uphold family traditions for generations to come.

From Street Races to Enterprise Legacy

You don’t need Piccolo Petes to build this kind of memory and leadership capital. Every family has its version - a weekend cookout, a beach bonfire, an annual fishing trip, or maybe your own quirky “derby day.” What matters is that the tradition continues, adapts, and welcomes every generation.

These are the spaces where:

• Future board members first experience leadership.

• Young family members build safe, healthy risk tolerance - learning to try, fail, adjust, and try again.

• Family identity gets reinforced through action, not speeches.

These are the moments where legacy is made, not just inherited.

A Reflection for Your Summer Table

This summer, as you gather your family, consider this:

What is the “Piccolo Pete Race” in our family? Where are we giving the next generation a place to lead, to take initiative, to practice stewardship, not just of assets, but of moments and memories?

Because it’s in these small, joyful acts that we build the next generation of stewards, equipped with both head knowledge and heart connection.

One day, long after today’s balance sheets are forgotten, your family will thrive on the stories of who built the fastest cart, who laughed until they cried, and who took the lead when it was needed most.

📚 Read Family Fortune 📅 Book time with Mike Schmitt