The Billionaire Trust Strategy You've Never Heard Of | Dan Pascone with Alessandro Chesser | Ep #35

Alessandro Chesser spent his first decade in banking, at Bank of America, Wells Fargo, and Washington Mutual, working the sales side of high-net-worth banking: deposits, loans, and investments. That's where he first learned how trust documents work and why wealthy families rely on them.

He then spent nearly eight years as Carta's first sales hire, helping grow the company from nothing to more than $300 million in annual recurring revenue. Dynasty, the company he later founded with two former Carta colleagues, combines both halves of that career: trust knowledge from banking, and the software instinct to make a historically expensive, paperwork-heavy process available to a much wider group of startup founders and early employees.

Alessandro's starting point is one we make to clients regularly: a will alone routes your estate through probate, a court process that typically runs 12 to 18 months and can stretch to five or six years if a family disagrees or someone contests it. A basic revocable trust lets a successor trustee you name settle your estate privately, without a judge, and without the delays and legal fees probate can generate. It's the entry-level move most families are missing, not an advanced strategy reserved for the wealthy.

Beyond a simple revocable trust, Alessandro's business is built around irrevocable trusts formed under Nevada or South Dakota law, two states with legal frameworks he describes as the best in the country for asset protection and taxes. Properly drafted, these trusts can be difficult for creditors or plaintiffs in a lawsuit to reach, carry no state income tax at the trust level, and can hold assets across multiple generations without triggering estate tax at each transfer the way a standard estate might.

The tradeoff is real: irrevocable means exactly what it says. Once assets are gifted into the trust, the grantor gives up direct ownership and control, in exchange for that asset protection and tax treatment.

Qualified Small Business Stock, under Section 1202 of the tax code, lets founders, early employees, and certain investors exclude a meaningful slice of capital gains from federal tax when they sell stock in a qualifying company. Alessandro puts the number at roughly $10 million to $15 million depending on when the shares were issued. To qualify, the company generally needs to be a C-corporation, not an LLC or S-corp, can't be primarily a services business, and the stock needs to be held for at least five years.

The exclusion applies per taxpayer, per company. Alessandro's business is built around a specific extension of that idea: a properly structured, independently trusteed irrevocable trust can potentially hold its own separate QSBS exclusion for the same company's stock, which is why gifting shares into several trusts, for a spouse, children, or other beneficiaries, can multiply the total amount of gain that's eligible for exclusion.

The instinct is to treat this as a paperwork exercise: set up a few trusts, gift some shares, and the tax savings follow automatically. In practice, QSBS trust stacking sits in a technical, closely watched corner of the tax code. The IRS and courts have scrutinized aggressive versions of these arrangements, particularly when a grantor keeps effective control over trust assets or the trusts aren't administered as genuinely separate, independent entities. The strategy is legitimate when it's done correctly, with real gifts, real independent trustees, and documentation that holds up, but “correctly” is doing a lot of work in that sentence.

That's exactly why this kind of planning needs a coordinated team: a securities attorney to confirm QSBS eligibility, a tax professional to model the gift and exemption impact, and an independent trustee, not a single vendor promising a shortcut. Alessandro's own advice reflects this: Dynasty doesn't make your stock QSBS-eligible in the first place, a lawyer and a platform like Carta do that work first.

Consider two hypothetical founders of the same company, three years apart in when they act. The first gifts shares into a handful of irrevocable trusts in year one, when the company is worth next to nothing. That gift uses up almost none of her roughly $14 million lifetime gift and estate tax exemption, and all the future growth happens inside the trusts, growth that, if the underlying stock qualifies, can later come out tax-free under each trust's own QSBS exclusion.

The second founder waits until after a Series B, when his shares are worth $8 million. Gifting the same percentage into trusts now uses up more than half his lifetime exemption in a single transaction, and he has far less flexibility left for future estate planning. Same strategy, same paperwork, a very different result, because he waited for certainty instead of acting while the stock was cheap.

We see the trust side of this conversation constantly with founders and executives who hold concentrated, appreciating equity, whether that's pre-IPO stock, RSUs, or a business they built themselves. A properly structured trust, revocable or irrevocable, is one tool in a much larger plan, alongside your tax strategy, your liquidity timeline, and your estate documents, not a stand-alone fix. We cover the full toolbelt, SLATs, GRATs, ILITs, and QSBS timing, in our own trust playbook for high earners, and the broader exit-planning sequence, including QSBS stacking specifically, in how founders turn a valuation into an actual legacy.

Alessandro's rule of thumb: anyone who owns roughly 2% or more of a non-services C-corp with real exit potential, founders, co-founders, some early employees, and some early investors. On a $1 billion exit, 2% is $20 million; without trust planning, everything above your personal $10 million QSBS cap is taxed at full rates. Recent tax law changes have also moved the ground under this planning: the federal lifetime gift and estate exemption expanded starting in 2026, and QSBS itself saw enhancements in the same legislation, both of which change the math on when and how much to gift. We break down what else changed for executives here.

This episode lines up closely with a meaningful slice of our own clients: founders and early employees at venture-backed or fast-growing C-corp companies who hold real equity and are years, not months, from an exit. If that's you, the lesson isn't to run out and set up trusts on your own; it's to get your equity, your tax exposure, and your estate documents in front of a coordinated team while your shares are still cheap enough that acting is easy.

If you're further along, already through a liquidity event or managing concentrated stock from years of vesting, the underlying principle still applies: get appreciating assets positioned correctly before the growth happens, not after.

Whether you're a founder years from an exit or an executive sitting on concentrated stock today, the trusts, the tax exclusions, and the timing only work if they're coordinated with the rest of your plan. Book a free Wealth Strategy Call and we'll look at your equity, your timeline, and your estate documents together: no product pitch, just a clear-eyed conversation about your hybrid retirement.