Sellers routinely anchor on price per share and discover the rest at closing. The rest is knowable in advance. Here is the checklist, in the order the money moves.
Getting to sellable shares
If you hold options rather than shares, selling usually means exercising first: paying the strike price, and — depending on option type and timing — potentially triggering tax at exercise. Some transactions net this out (exercise and sale settle together); others require cash up front. Know which yours is before agreeing to terms.
Transaction costs
Expect some combination of platform or broker fees, legal or processing charges, and — in some deals — a discount for the buyer’s diligence burden. Ask for the all-in cost as a percentage of proceeds; honest counterparties can answer in one line.
Taxes, in broad strokes
For most U.S. holders, selling shares is a capital-gain event: proceeds minus your basis, taxed at long-term rates if you’ve held the shares more than a year, short-term (ordinary) rates if not — and the holding-period clock has its own rules when options are involved. Two more items belong on your radar screen: qualified small business stock (QSBS) treatment, which can exclude substantial gain on eligible early-stage shares if strict requirements are met, and state taxes, which follow their own rules. None of this is advice — it is a map of the questions to bring to a tax professional before the sale, when structure can still change the answer.
Timing and mechanics
Between signing and settlement sit the company’s consent process and any right of first refusal — the full lifecycle is here — so plan on weeks. Funds should reach you through escrow or custody settlement, never a counterparty’s personal account.
The one-page worksheet
Before you say yes: sale price × shares, minus exercise cost, minus fees, minus estimated tax — equals what this decision is actually worth. Ten minutes with that arithmetic prevents most seller’s remorse. When you’re ready to think about process, For Shareholders covers your side of the transaction.
Educational only. InvestNow is a demonstration platform. This page is general information, not investment, legal, or tax advice, and not an offer or solicitation of any security. Private-market investments are speculative, illiquid, and can lose their entire value. Consult a qualified professional about your circumstances.