Alessandro Chesser

What if estate planning didn’t feel intimidating, expensive, or like something you only did later in life?

Alessandro Chesser is quietly revolutionizing how we think about legacy. As the founder of Dynasty, he’s reimagined living trusts—one of the most powerful yet underutilized tools in personal finance—and made them accessible to everyday people through a beautifully simple digital platform.

But Alessandro didn’t get here by accident. After playing a key role in scaling Carta, one of the biggest names in cap table management, from zero to over $300 million in recurring revenue, he left to build something more personal. Dynasty isn’t just about paperwork; it’s about agency. It’s about making sure people—no matter their background—can protect what they’ve worked for and pass it on with intention.

This conversation isn’t just about estate planning. It’s about how you build trust in a space full of fear, confusion, and procrastination—and why Alessandro believes that clarity and simplicity are the most radical forms of innovation.