First Builders
The First Builders Podcast from The Council dives into the stories of those who go first—founders, funders, and early operators who helped build category-defining companies before they were household names. Hosted by General Partner Amber Illig and Partner Rachel Tsui, each episode brings a candid, practical conversation with someone who has helped shape companies before there was a playbook.
First Builders
Democratizing Wealth: Alessandro Chesser on Building Dynasty and Lessons from Carta’s Early Days
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.
FOLLOW ALESSANDRO CHESSER
LinkedIn: https://www.linkedin.com/in/alessandrochesser
Dynasty: https://getdynasty.com
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