For owners within ~5 years of a sale
Most of the money is won or lost before the letter of intent.
By signing, the structure is fixed. Which entity holds the stock, how long it has been held, where you were resident when it closed — nearly all of it is already decided, and most of it cannot be undone.
- Fee-only fiduciary · CRD 314416
- This firm earns no commissions
- Operator, not just an adviser
What is timing worth on your sale?
Ten seconds. No email, no signup.
What you put in. Founders are often close to zero.
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Five things that decide the number.
All of them are settled before closing. Most of them cannot be revisited afterwards.
The domicile gate
Gain on an intangible is sourced to residency at sale. Often the single largest line in the whole transaction — and the one most often done badly. The full sequencing analysis →
Section 1202 / QSBS
Can exclude a large share of the gain on qualifying C-corp stock. Turns on facts fixed years earlier, and was materially amended in 2025.
Instalments and deferral
Spreading proceeds keeps you out of the top bracket, but carries credit risk — and does not move the source of the gain.
One asset, all of it
Your whole net worth sits in an illiquid position whose value depends on you turning up. No risk questionnaire has anything useful to say about that.
The Monday after
A number you have never had to invest, no business to absorb your attention, and every institution in the country wanting a meeting.
3–5 years out
Early enough to change the structure. At twelve months some doors are shut but domicile and instalment questions are live. If you are further out than five years, there is usually nothing to do yet — and I will say so.
Thirty minutes, no cost, no pitch.
If the timing is wrong or another adviser fits you better, you will hear that in the first conversation rather than the third.
Zachary Wolfson
Founder, Wolfson Private Wealth
Most advisers who market to business owners have never made a payroll or carried a receivable. Alongside this firm I operate other companies — so the conversation about what your business costs you and what it would take to leave it is one I can have from experience rather than from a brochure.
Zach Wolfson owns and operates other businesses outside this firm, including insurance agencies that earn commissions on health and Medicare insurance. Wolfson Private Wealth sells no insurance, earns no commission on anything, and is paid only the advisory fee its clients pay it. The firm does not recommend that its clients buy insurance through those agencies, and any policy a client buys anywhere is outside this engagement and is never billed under it. These outside businesses take time and attention, which is a conflict worth knowing about. They are disclosed in Item 4 of Zach's Form ADV Part 2B and Item 10 of Part 2A, which you can read at adviserinfo.sec.gov under CRD 314416.
- Florida-registered · CRD 314416
- Individual CRD 6584857
- Fee-only firm
- Series 7 & 66
Verify at adviserinfo.sec.gov. Registration does not imply any level of skill or training.
How this estimate works, and what it cannot do
Criteria and methodology
- The estimate takes the gain (sale price less basis), applies the federal long-term capital gains rates on a stacked basis and the 3.8% net investment income tax, and then applies your current state’s top marginal rate to the same gain.
- The figure it reports is that state layer — the amount sourced to your state of residence, which is the part that changes if the sale closes after a completed change of domicile. The federal amount is owed either way and is shown as such.
Assumptions and limitations
- Your state’s TOP marginal rate applied to the whole gain. Real liability reflects graduated brackets, local taxes and any state-specific treatment, so the true figure will usually differ.
- A completed and defensible change of domicile. The saving depends entirely on that being genuine — not on the arithmetic. A change of address is not a change of domicile.
- It does not model Section 1202 / QSBS. That provision was materially amended in 2025, runs two parallel regimes, and turns on facts this form does not collect. A QSBS figure derived from three inputs would be a guess.
- It does not model instalment sales, earn-outs, escrow, equity compensation (which is sourced to where the work was performed), state statutory-residence day-count tests, alternative minimum tax, or any state estate tax.
- It assumes the entire gain is long-term capital gain to one joint filer with no other income. Real transactions rarely are.
Investments considered
- This tool considers no investments. It compares tax regimes on a single transaction and neither recommends nor selects any security, fund, manager or product.
Applies to every result this tool produces
- Results are hypothetical in nature. They are produced by a model, not by any account, and no client obtained them.
- Results vary with each use and over time — with the figures you enter, with the assumptions above, and with changes in tax and Medicare law, which change annually.
- This tool does not consider your full circumstances and is not investment, tax, or legal advice. Using it does not create an advisory relationship.