Alessandro Chesser

In this enlightening discussion, Alessandro Chesser, Co-founder and CEO of Dynasty, shares his extensive experience from his years as a sales executive at Carta. He explains why South Dakota is a key location for setting up trusts and the benefits of choosing between revocable and irrevocable options. Discover innovative tax strategies for entrepreneurs, including significant savings through qualified small business stock provisions. Chesser also emphasizes the importance of trusts for financial protection, especially for startups generating substantial revenue.

Alessandro Chesser, a tax strategist from Get Dynasty, dives into the world of Qualified Small Business Stock (QSBS) – a powerful tool that can enable entrepreneurs to sell their companies tax-free. He explains who qualifies and how specific industries can benefit, along with recent changes that raised exclusion limits and introduced strategic planning around trusts. Listen to learn about the best timing for QSBS and how to turn a transition from LLC to C-Corp into substantial tax savings!

In this chat, Alessandro Chesser, CEO of Dynasty and former sales leader at Carta, discusses his journey from navigating sales challenges to launching a fintech platform. He stresses the importance of syncing business and product teams, revealing lessons learned from Carta's setbacks. Alessandro shares how TikTok is driving organic growth, emphasizing the power of viral content to engage younger audiences. Lastly, he dives into the complexities of automating trust creation, highlighting both legal hurdles and the potential to revolutionize asset management.