[Podcast Episode #18] What’s Your 500 Year Plan?

Too often, when we talk about legacy, we shrink it down to money in a trust fund or a building with our name on it. But true legacy—lasting legacy—requires a deeper vision.

Entrepreneurs are trained to chase quarterly profits and rapid growth. The pressure is always short-term: grow faster, hit the next target, win the market. But history tells us something different. Families and leaders who left behind something that lasted for centuries took a far broader view.

The Medici family of Renaissance Florence is our case in point. Six hundred years after Cosimo de’ Medici walked the streets of Florence, millions still visit to admire what his family built. Their legacy wasn’t just banking success—it was a deliberate diversification into politics, art, architecture, and even spiritual influence. They built more than wealth; they built a cultural ecosystem that shaped generations.

And here’s the key difference: “An inheritance is something you leave to people. A legacy is something you leave in people.” Wealth transfers often fail within a few generations because money without wisdom quickly disappears. Legacy, on the other hand, is about values, vision, and character being passed down alongside resources. It is about forming people, not just funding them.

This means we must shift our mindset from ownership to stewardship. When we first start a business, it’s natural to think, This is my company, my team, my dream. But legacy calls for a bigger perspective. We are temporary stewards of resources that can impact far beyond our lifetime. That shift changes everything—how we structure wealth, how we prepare our children, and how we define success.

The Medicis understood something most entrepreneurs ignore today: beauty matters. They didn’t stop at commerce; they became patrons of art, commissioning works by Michelangelo, Leonardo da Vinci, and Donatello. Those works still inspire millions of people centuries later. What if part of your legacy wasn’t just financial success but also beauty and inspiration that outlive you?

Legacy planning isn’t about a quick handoff. It’s what Cris and Philip call “500-year thinking.” It sounds absurd, but it forces us to slow down and ask different questions: What values do we want to embed into our families and businesses? How do we structure assets so they serve generations we’ll never meet? How do we leave something that will outlast even our memory?

We may never know exactly how the future will unfold, but if we think like Cosimo did—if we create with stewardship, values, and beauty in mind—we stand a far greater chance of leaving not just wealth, but meaning. And that is a legacy worth building.