#21 Alessandro Chesser: Democratizing Wealth Protection

Alessandro Chesser, Founder and CEO of Dynasty Trust Company, shares his journey from scaling Carta’s sales to founding a startup that simplifies Nevada trusts. He discusses leveraging technology to make asset protection affordable, the challenges of B2C markets, and the impact of AI on sales.He is helping people protect and pass on wealth using modern trust structures. A Silicon Valley native, he spent 10 years in financial services before joining Carta as the first sales hire, helping grow it to $300M+ ARR. Now he’s bringing billionaire-level estate tools to everyone.Links: https://www.getdynasty.com/About Federico Ramallo:Software Engineering Manager | Founder of DensityLabs.io & PreVetted.ai | Connecting U.S. teams with top nearshore LATAM engineers.- 💼 https://www.linkedin.com/in/framallo/- 🌐 https://densitylabs.io- ✅ https://prevetted.aiPreVetted Podcast:- 🎙 https://prevetted.ai/podcastCHAPTERS00:00 - Introduction to PreVetted Podcast00:17 - Guest Introduction: Alessandro Chesser00:33 - Founding Dynasty: Identifying the Market Gap01:39 - Challenges in Building a Consumer Startup02:27 - Benefits of Nevada Trusts for Asset Protection04:27 - Transferring Assets to a Nevada Trust05:22 - Combining Trusts with LLCs for Optimal Structure06:20 - Tax Benefits of Qualified Small Business Stock07:46 - Measuring Success at Dynasty: Revenue and Metrics09:23 - Raising Venture Capital for Dynasty10:13 - Scaling Carta’s Sales Team: Lessons Learned19:57 - Impact of AI on Business and Sales23:22 - Advice for Aspiring Sales Professionals27:51 - Using Voice AI Agents at Dynasty29:55 - Future Goals for Dynasty: Becoming a Household Name31:03 - Closing Remarks and Episode Wrap-Up