Should I sell some or all of my equity?

This is usually the real question once you've decided a sale is possible. The answer is almost never 'all' or 'nothing' — it's a number that fits your risk and goals.

Think in terms of risk, not prediction

You can't know whether the company will soar or stall. So size the sale around how much certainty you want, not a forecast. A useful frame: how much would you need to sell to feel secure regardless of what happens next — and how much would you keep to still benefit if it succeeds?

What should push you to sell more

High concentration — most of your net worth in one private company. Measure it.
Near-term needs — a house, debt, family, or simply locking in life-changing money.
A long or uncertain road to exit.
A rare, fairly-priced window that may not return soon.

What should push you to keep more

Strong conviction and good information about the company.
A steep discount to sell now, or tax clocks you haven't yet reached (long-term, QSBS).
Already-diversified wealth, so this equity is a smaller slice of your risk.

A practical approach

Decide the cash figure that would make you feel secure (taxes, debt, a cushion, a goal).
Sell roughly enough to reach it, net of tax — no more than a fair window and any caps allow.
Keep the rest for upside. Revisit at the next window.

Selling in tranches across multiple windows also spreads your tax and your timing risk — you needn't decide the whole thing at once.

Frequently asked questions

Is it smart to sell only part of my equity?

Very often, yes. A partial sale lets you lock in real money and cut concentration risk while keeping a stake for upside. Most employees who sell don't sell everything — they take enough off the table to feel secure and hold the rest.

How do I decide how much to sell?

Start from the cash amount that would make you feel financially secure — covering taxes, debt and a cushion — and sell roughly enough to reach it after tax. Weight toward selling more if you're heavily concentrated, and less if your wealth is already diversified.

Can I sell equity in stages?

Often yes, if your company runs repeated tenders or there's ongoing secondary demand. Selling in tranches spreads your tax across years and reduces the risk of mistiming a single large sale.

Get the numbers before you decide

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