Productizing QSBS Trust Stacking
Alessandro Chesser, CEO of Dynasty, on supercharging QSBS for founders & investors
The key shift is that QSBS trust stacking moved from bespoke estate planning for already wealthy insiders into a startup onboarding product. Before software wrapped the process, a founder needed an estate lawyer, a licensed trustee, and a valuation firm just to move cheap early shares into trusts, which made the strategy practical mainly for people who had already had exits, fund carry, or a family office paying the bills.
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The old workflow was expensive in very concrete ways, about $25,000 per trust for legal setup, $8,000 to $10,000 per trust each year for a third party trustee, and about $30,000 for valuation work. Creating three or four trusts could mean a first year bill in the low six figures or higher.
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That cost mattered because timing is the whole game. The best moment to gift shares is when they are worth almost nothing. Once a company reaches Series A or Series B and the stock has real paper value, the founder burns through the lifetime gift exemption much faster and loses most of the stacking room.
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This is why vertical integration matters. Dynasty and peers like Valur are not just selling documents. They are compressing trust formation, valuation, and administration into one product, similar to how Secfi turned option exercise planning from a specialist service into software for a much larger set of startup employees and founders.
The market is heading toward incorporation era tax infrastructure, where setting up a trust sits alongside the 83(b) election as an early cap table decision. If that behavior becomes standard, the winning company will be the one that captures founders when equity is still cheap, then keeps the relationship as those trusts turn into cash, investments, and multigenerational wealth.