Check Five Numbers Before Selling Startup Shares in a Tender

You are holding unlisted startup shares, and a tender offer asks how much of your vested shares, the shares you have earned, to sell. The decision is a number. You are comparing a certain price today against an uncertain future price, a cap on what you can sell, and your own balance sheet.

A tender can feel like a gift: cash now, before a public listing. The trap is treating it as a full exit. The rule is to size a partial exit before you sign.

A tender is a partial exit

OpenAI reportedly bought back $7 billion of employee shares in a tender that valued the company at $852 billion. The tender valuation matched OpenAI's March financing, which added $122 billion to the company. The last round is the reference point for whether the tender is a discount, a fair price, or a premium.

Before the latest deal, OpenAI had offered employees a $6.6 billion sale at a $500 billion valuation in October and a $1.5 billion sale in 2024. The October valuation was lower than the latest tender valuation. In that October tender, roughly 75 sellers reached the $30 million cap, while the other 525 split $4.35 billion for an average of about $8.3 million each. The cap changed the decision for each seller, even though the price was the same.

Anthropic completed an April 2026 tender at a $350 billion valuation before a new round, alongside a $30 billion Series G that brought its valuation after the round to $380 billion. A tender next to a financing lets you check the tender price against the round price, which sharpens the comparison.

Five numbers size the sale

Multiple-criteria decision analysis is a way to compare options when several goals conflict. A repeatable framework reduces guesswork and points you to the option that fits your criteria. The framework is a whiteboard: list the goals, compare the options, and choose the amount that fits the whole set. For a tender, the goals are cash now, upside later, tax cost, and concentration risk.

The spread between the tender price and the last round sets the price. Below the last round, you are being paid to exit early. Above it, you are being paid to reduce risk before the next event. At the same price, the cap and your personal finances decide the size.

A participation cap is the maximum the company will honor, not a suggestion. A cap can turn a large intended sale into a smaller one. If your desired sale is larger than the cap, the question changes from how much to sell to whether the cap is enough to make the position safer. If the cap is not enough, you may hold more than you want, but you should know that before signing.

IPO timing, the timing of a public listing, is the hardest number because it is often a range, not a date. A filing is a step, not a calendar. A confidential filing can mean the company is preparing, but it can also mean the listing is far away or not happening soon. OpenAI filed an IPO prospectus with the SEC, the securities regulator, in June but did not state a listing date. The checklist does not ask you to predict the market. It asks you to state what you believe and then size the sale so you are not forced to guess.

Concentration is the personal number. The same share count can be a rounding error for one person and a life-changing position for another. For a large position, selling part of the shares can reduce the chance that a single company's next event controls your life. For a small position, holding may be easier. Tax basis matters because the same sale can be a small gain for one person and a large tax cost for another.

Run the checks in order. The first two set the price, the third sets the size, and the last two set the personal cost.

• Last-round price: Find the most recent financing price per share and compare it to the tender price.
• Tender price: Calculate the per-share price you would receive and note whether it is below, equal to, or above the last round.
• Participation cap: Check the maximum amount you may sell and decide whether that amount is enough to reduce risk.
• IPO timing: Ask whether a listing is expected soon, whether a filing exists, and whether the company has given a date.
• Personal concentration and tax: Measure how much of your net worth is in the shares and note your tax basis, the cost you paid for them.

The checklist becomes a sell amount

The tender versus IPO question is about timing and concentration. Below the last round, the default is to sell less. Above it, sell more, but only up to the cap and only if your concentration is high. A close IPO may make holding worth the wait. An unclear IPO makes a partial cash-out the safer move.

Sell enough to reduce risk, hold enough to keep upside, and write down the reason before the offer expires.