Trusts Build Fortunes! How Alessandro Chesser Scaled Dynasty with Ackman & TikTok

Most people don't realize that the wealthiest individuals quietly use trusts to protect and transfer their assets—while everyone else gets stuck in probate court, paying unnecessary fees and taxes. In this episode of Resilient Riches, Yair and David Klyman sit down with Alessandro Cheeser, founder of Dynasty, a tech-forward trust company that's turning the traditional legal industry on its head. After building Carta into a multibillion-dollar startup, Alessandro turned his attention to the outdated world of estate planning—and built a scalable, VC-backed disruptor doing 30,000+ trusts in just 2 years. You'll learn: Why revocable trusts are one of the most powerful (and underused) tools in personal finance How Alessandro's team digitized trust creation—making it as easy as updating your social profile The difference between revocable vs. irrevocable trusts—and how the wealthy use them to protect assets from lawsuits, creditors, and taxes How to raise capital from elite investors like Bill Ackman and the founder of Insight Partners—even if you're a first-time founder Why traditional Facebook ads are dead, and how influencers + TikTok are reshaping customer acquisition The smart strategy behind giving away your product for free—and making money elsewhere What startup founders can do to eliminate $10M+ in capital gains taxes Alessandro also shares his personal journey—from working as a bank teller at 16 to building legal tech companies that are reshaping industries. If you're a founder, advisor, or simply someone who wants to understand how real wealth is built and protected, this episode is a must-listen.