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.ai

PreVetted Podcast:

- 🎙 https://prevetted.ai/podcast

CHAPTERS

00:00 - Introduction to PreVetted Podcast

00:17 - Guest Introduction: Alessandro Chesser

00:33 - Founding Dynasty: Identifying the Market Gap

01:39 - Challenges in Building a Consumer Startup

02:27 - Benefits of Nevada Trusts for Asset Protection

04:27 - Transferring Assets to a Nevada Trust

05:22 - Combining Trusts with LLCs for Optimal Structure

06:20 - Tax Benefits of Qualified Small Business Stock

07:46 - Measuring Success at Dynasty: Revenue and Metrics

09:23 - Raising Venture Capital for Dynasty

10:13 - Scaling Carta’s Sales Team: Lessons Learned

19:57 - Impact of AI on Business and Sales

23:22 - Advice for Aspiring Sales Professionals

27:51 - Using Voice AI Agents at Dynasty

29:55 - Future Goals for Dynasty: Becoming a Household Name

31:03 - Closing Remarks and Episode Wrap-Up