The work is done before the exit, not after.

You may not need trust planning, and if so we will say so. You still need to know that the stock qualifies, where each tranche sits against the holding period, and that there is a basic estate plan behind it. For many founders under the cap, that is the whole engagement: a QSBS Qualification Review and a family plan, with no trust at all.

Then the planning question changes, and it is better to have asked it early. Transfers to family members or to trusts are valued when they are made, so the options are widest while the stock's value is still low. A review done now records where you stand, which makes it quicker to revisit after a strong round. It does not commit you to any structure.

It depends on when each share was acquired. For stock acquired after 4 July 2025, the exclusion is tiered: 50% after three years, 75% after four, and 100% after five. For stock acquired on or before that date, there is no exclusion unless the stock has been held more than five years.

In some cases a Section 1045 rollover, which defers gain by reinvesting the proceeds in other qualified small business stock, is worth evaluating. Whether it is available, and whether it makes sense, depends on your facts and on the deal.

Each tranche is governed by the regime in force when it was acquired, with its own holding-period rule and its own figures, as the two regimes above set out. How the two interact for stock of the same company, and which shares to sell first if you have a choice, are among the things the review works through.

Yes. Stock received when an LLC converts to a C corporation can qualify, but generally the holding period starts at the conversion, and only gain that builds after the conversion is eligible for the exclusion. The conversion documents, the value at that date, and how the conversion was carried out all matter, so we ask for them early.

Usually not, but the available options are narrower and the cost of using them is higher, because transfers are valued at what the stock is worth when they happen. We would rather look at your facts than answer in the abstract. There is often useful work to do on documentation, entity hygiene, and the foundation plan even when the most aggressive structures are off the table.

No, and we would treat a confident answer to that question as a warning sign. The benefit available under Section 1202 depends on facts that are unresolved at the time planning is done: whether the company satisfies every requirement at every relevant moment, whether a sale occurs, in what form, at what price, under the law in force on that date, and how the structure is viewed if it is examined.

What we can tell you is what the statute makes available on facts like yours, what the structure would require of you, what it would cost, and where the risk sits.

That is the first question we answer, and it is not always yes. Qualification turns on the entity's form, whether the stock was acquired at original issue, the nature of the company's business, the company's gross assets immediately after the stock was issued, the company's redemption history, and how long you have held each tranche. Several of those are facts fixed in the past.

The numbers themselves also depend on when you acquired the stock, which is what the two regimes above set out. Where the answer is no, or unclear, we will tell you that directly, along with what, if anything, can still be done.

Because the federal analysis is only part of it. Washington State is a community property state. The District of Columbia and Maryland are not. Maryland also imposes its own estate tax at a threshold well below the federal exemption, and levies an inheritance tax on certain beneficiaries, neither of which the federal exemption addresses. State law affects whether stock is separate or community property, where a trust can be administered, and what a transfer costs at the state level.

State taxes are a design input, not an afterthought. A structure that looks efficient federally can carry a state-level cost that was never weighed. Chad R. Vickery is admitted to practice in all three jurisdictions, which is why we can look at the whole picture rather than only the federal law.

Your corporate counsel represents the company; we represent you and your family. Planning that the corporate record does not support may not survive diligence, so we would rather coordinate with them from the beginning on transfer restrictions, board consents, stock certificates, and the cap table than hand everyone a surprise later.

We provide flat fees in writing before any drafting begins, not an hourly rate or an open-ended estimate. What the work costs depends on which structures actually fit your facts, how many entities and accounts are involved, and how much corporate cleanup the cap table needs, so fees are discussed on the first call, once the situation is clear.

The review itself is quoted up front too, so you are never billed into a decision you have not made. We are happy to talk about the range your situation is likely to fall into on the first call.

It depends on your question. If it is about your equity, whether your stock qualifies, where your holding periods stand, or whether trust planning is worth doing, start with the QSBS Qualification Review.

If you already have a family estate plan and want to see whether it is funded and still fits, start with the free Estate Plan Check-Up. It runs in your browser and collects nothing. Many founders end up doing both.

Yes, with your consent. Your CPA keeps the returns. We coordinate on basis, holding periods, valuation, and gift reporting, so the returns and the structure tell the same story.

No. We coordinate with your CPA, who prepares the returns, including any trust fiduciary or gift tax returns.