Democratizing Wealth: Alessandro Chesser on Building Dynasty and Lessons from Carta’s Early Days
Description
What if the same wealth tools billionaires use were accessible to everyone?
In this episode of First Builders, hosts Amber Illig and Rachel Tsui sit down with Alessandro Chesser, Co-Founder & CEO of Dynasty, a licensed Nevada trust company helping founders and investors maximize equity value through smart ownership structures like QSBS stacking.
Before founding Dynasty, Alessandro spent eight years at Carta, joining as the company’s first sales hire and helping scale revenue from zero to $300M. Along the way, he learned how ownership structures shape outcomes—not just for investors, but for founders and employees too.
In this conversation, Alessandro shares:
– Lessons from building Carta’s early sales and culture
– Why trust and education are the missing pieces in equity strategy
– How Dynasty is democratizing complex wealth tools like Nevada trusts
– The risk and reward behind becoming a licensed trust company
– Why compassion and clarity are underrated founder superpowers
It’s a candid look at what it takes to build credibility, complexity, and culture—from a first builder who’s done it twice.
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LinkedIn: https://www.linkedin.com/in/alessandrochesser
Dynasty: https://getdynasty.com
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