Twelve decisions, in order, from years before the letter of intent to years after the wire. Owners who can check every box tend to keep more, negotiate better, and sleep through diligence. Owners who cannot now know exactly where to start.
The highest-leverage phase. Everything here is cheap to do early and expensive or impossible to do once a buyer is at the table.
Section 1202 can exclude up to the greater of $10 million or 10x basis from federal gain, but only for qualifying C-corporation stock held five years. A structural review two or more years out is the difference between qualifying and reading about it afterward.
Work backward from the annual spending your next chapter requires to the after-tax proceeds that must fund it. Until that number exists, you cannot know whether an offer is good, only whether it is large.
Asset versus stock treatment, installment potential, charitable gifting capacity, and state residency should be mapped while every option is still open. Tax strategy negotiated after the letter of intent is mostly tax acceptance.
CPA, deal counsel, investment banker, and wealth advisor should be in the same conversation before the process starts, not introduced mid-diligence. A coordinated team catches structure problems while they are still drafting notes rather than closing conditions.
Terms, not just price. The economics of a transaction live in its structure, and structure is only negotiable while the ink is wet.
Two offers at the same price can differ by millions after tax depending on asset versus stock treatment, purchase-price allocation, and earnout terms. Model each offer to net proceeds before comparing them.
Seller notes can spread gain across tax years and generate interest income, but they also carry buyer credit risk. Choose the structure against your independence number and your risk tolerance, not the buyer's convenience.
Rolling equity into the buyer's entity defers tax and keeps upside, but it also keeps a slice of your net worth concentrated and illiquid. Size it as you would any single-company position: intentionally and with limits.
A move to a lower-tax state can meaningfully change the outcome, but only if the change of domicile is genuine and established before the gain is recognized. Timelines, documentation, and state rules decide this, so it is planned early or not at all.
The transaction ends. The stewardship begins. What the sale created is protected here or not at all.
Tax reserves, near-term commitments, and an operating cash buffer are defined in advance so the proceeds land into a structure rather than a checking account. The first ninety days after a sale are when unforced errors happen.
Moving from one concentrated private asset to a diversified portfolio is a process measured in quarters, with entry points and allocations agreed in advance. A schedule replaces the two classic mistakes: deploying everything at once and deploying nothing for years.
Documents drafted when your wealth was a private company rarely fit a balance sheet of liquid capital. Titling, trust funding, and exemption planning should be revisited within months of close, not at the next decade's review.
Liquidity is visible in ways an operating company never was, which changes insurance needs, creditor exposure, and how the next generation encounters the money. Governance, education, and protection structures turn a windfall into a foundation.
Bring your situation. We will identify which of the twelve points are done, which are open, and which are urgent.
