Dynasty CEO explains QSBS trust stacking — how founders can get up to $100M in tax-free gains starting at $1,500/year
Nov 5, 2025 with Alessandro Chesser
Key Points
- Dynasty, a licensed Nevada trust company, enables founders to establish multiple QSBS-eligible trusts at $1,500 per year, allowing them to shield up to $100 million in capital gains from federal tax by acting at incorporation when share value is near zero.
- CEO Alessandro Chesser observed at Carta that successful founders consistently held equity across multiple trusts rather than individually, a tax arbitrage strategy previously accessible only to ultra-wealthy families willing to pay six-figure setup costs.
- Dynasty estimates 250,000 to 500,000 U.S. C-corporations qualify for QSBS tax sheltering beyond venture-backed tech, including plumbing manufacturers and sanitation companies, with a longer-term ambition to extend Nevada trust access to crypto holders and farm asset owners.
Summary
Alessandro, co-founder and CEO of Dynasty, built his thesis on an observation from his eight years at Carta, where he joined as the first sales hire in 2014 and helped scale the company from zero to $300 million in ARR. While onboarding thousands of cap tables, he noticed the most successful founders consistently held equity across multiple trusts rather than in their own names. The reason was structural arbitrage inside the tax code.
Qualified Small Business Stock (QSBS) exemptions allow each trust to shelter up to $10 million in capital gains from federal tax. A founder who establishes 10 trusts before meaningful equity appreciation can therefore shield up to $100 million in gains from taxation entirely. The catch is timing. Traditional trust setup costs run into six figures, pushing most founders to act too late, when gift tax implications from appreciated shares cap how many trusts can realistically be funded.
Dynasty's pitch is access at entry-level cost. A typical setup for a Y Combinator-stage founder involves four trusts for $1,500 per year, covering up to $40 million in QSBS eligibility. Beneficiaries are usually spouses, children, parents, or siblings. The optimal moment to act is at incorporation, when share value is effectively zero and no gift tax applies.
QSBS eligibility extends beyond venture-backed tech. Alessandro cites plumbing manufacturers and portable sanitation companies as examples. He estimates somewhere between 250,000 and 500,000 U.S. companies could qualify, provided they are structured as C-corps and fall outside excluded regulated industries such as financial services.
Dynasty operates as a licensed Nevada trust company, which Alessandro describes as the only venture-funded entity in that category. Nevada trust law is the draw for ultra-high-net-worth families nationally because of its advantages on taxes, asset protection, and privacy relative to states like California and New York. Dynasty's longer-term ambition is to extend Nevada trust access to a mass-market audience, including individuals with modest crypto holdings or farm assets, using an AI-powered platform. The current focus on founders is explicitly a wedge strategy.