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Alessandro Chesser is the founder and CEO of Dynasty, a startup focused on making Qualified Small Business Stock (QSBS) trust stacking accessible to founders. Before launching Dynasty, he led sales at Carta from the early days to roughly $300M in ARR, gaining hands-on insight into equity workflows, 409A dynamics, and how distribution is built around real, recurring needs. Dynasty offers a subscription service—$1,500 per year for up to four family trusts—that includes trust creation, annual administration, and tax return filing, turning a traditionally bespoke, high-cost process into something founders can set up early in their journey.

In this episode, we unpack the mechanics and timing that make—or break—QSBS outcomes. We cover the core tests (acquiring shares before $50M in assets, five-year hold, qualified C-corp status), state-level differences (New York recognizes QSBS; California does not), and why early planning can start both the QSBS and long-term capital gains clocks while avoiding later surprises.

Chesser talks about trust stacking—gifting shares into multiple family trusts so each may pursue its own QSBS exclusion—and notes practical guardrails and expert advice for dong it right. Beyond the tax planning, Chesser shares go-to-market lessons from Carta and Dynasty: using the network effect (e.g., certificates signed), creating urgency with must-do workflows (like 409A), iterating growth levers monthly, hiring decisively, and using social + creator partnerships instead of traditional cold outbound. The result is clear: tactical advice for founders on when to exercise, when to gift, how to document, and how to avoid the common QSBS pitfalls discussed in the conversation.

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Key topics covered

- QSBS allows startup shareholders to sell up to $15 million tax-free.
- Most startups qualify for QSBS, but there are specific criteria.
- Holding shares for at least five years is crucial for QSBS eligibility.
- The new rules under the big beautiful bill change QSBS eligibility timelines.
- Dynasty helps founders maximize QSBS benefits through trust stacking.
- Early exercise of stock options can prevent alternative minimum tax issues.
- Filing an 83B election is essential for QSBS qualification.
- Social media is a powerful tool for startup growth and marketing.
- Building partnerships with influencers can enhance visibility and credibility.
- The cost of setting up trusts for QSBS is significantly lower with Dynasty.

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In This Episode, We Cover

(00:00) Introduction to QSBS and Its Importance

(06:35) Understanding QSBS Eligibility and Benefits

(13:08) The Role of Dynasty in Maximizing QSBS Benefits

(16:29) Alessandro's Journey and the Birth of Dynasty

(18:36) Growth Strategies and Lessons from Carta

(27:14) Leveraging Social Media for Growth

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Where to Find Alessandro Chesser:

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LinkedIn: https://www.linkedin.com/in/alessandro-chesser-84763748

X: https://x.com/SandroChess

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Where to Find Dynasty:

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Website: https://www.getdynasty.com

LinkedIn: https://linkedin.com/company/getdynasty

X: https://x.com/getdynasty_com

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Where to Find David Phillips:

X: https://x.com/davj

LinkedIn: https://www.linkedin.com/in/davjphillips