Should I sell my pre-IPO shares?

There's no universal right answer — only the one that fits your finances, your company and your risk appetite. Here's an honest framework, with no financing product or marketplace we're nudging you toward.

The short version

Selling some pre-IPO shares makes sense when a large share of your net worth is tied up in one illiquid company and you'd value certainty over maximum upside. Holding makes sense when you have conviction in the company, can afford the risk, and the tax or discount cost of selling now is steep. Most people who sell don't sell everything — they take some risk off the table and keep upside.

Reasons to sell some now

Concentration. If most of your wealth is in one private company, a single bad outcome is catastrophic. Selling a slice diversifies that risk. See the concentration calculator.
You need or want the cash. A house, debt, or simply locking in life-changing money that's real rather than on paper.
The exit may be years away — or never. Companies stay private far longer than they used to, and many never IPO.
A fair window is open. A company tender or strong secondary demand may not come again soon.

Reasons to hold

Conviction and information. You believe in the company and may know more than an outside buyer.
The discount is steep. Secondary buyers pay below the last round price after illiquidity and minority discounts; selling now can mean leaving value behind.
Tax timing. Selling before you hit long-term or QSBS thresholds can sharply raise your tax bill.
You can afford the risk. If this equity is a small part of your wealth, there's less need to act.

How to decide, in four steps

Know what you hold. Vested shares vs options vs RSUs, your strike, and your cost to exercise. Value your equity.
Check you can sell. Your ROFR and transfer rules decide if a sale is even possible. Can I sell before exit?
Price it realistically. Expect a discount to the last round. What discount is fair?
Size the sale to your risk. Decide how much certainty you want versus upside. Partial sales are normal.

Our honest position: we don't earn anything on your decision. Taking some risk off the table when a fair window opens is rarely something people regret; betting everything on one illiquid outcome sometimes is. But the right amount is personal.

Frequently asked questions

Is it a bad idea to sell pre-IPO shares before an IPO?

Not inherently. Selling locks in real money and diversifies risk, at the cost of some upside and a discount to the last round price. For many employees with heavy concentration in one company, selling a portion is prudent. Selling everything just before a strong IPO can mean leaving money on the table — which is why partial sales are common.

How much of my equity should I sell?

There's no fixed rule, but many people sell enough to take meaningful risk off the table — covering taxes, debt, or a life goal — while keeping a stake for upside. The more concentrated your net worth is in the company, the stronger the case for selling a larger slice.

Will I regret selling if the company IPOs higher?

Possibly on that slice — but that's the price of certainty. Framing it as insurance helps: you're trading some potential upside for protection against a bad outcome. Keeping part of your stake lets you participate if the company soars.

Get the numbers before you decide

Free, no sign-up: estimate what your stake is worth, the cost to exercise, and whether you can sell.

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When you're ready to go deeper, there's an optional Equity Toolkit and Report.