Plan Your Exit for Both Unlock Dates in a Tiered IPO Lockup

The trap is one exit date

If you hold startup equity, a tiered IPO lockup can split your exit into two separate decisions. The first is whether to sell any shares in the offering itself. The second is what to do when the remaining shares become freely tradable. If you treat both as one event, you may sell too early or wait too long.

Anthropic is weighing an IPO structure in which existing shareholders can sell part of their holdings at the offering, while at least some investors and employees remain restricted from selling for more than 180 days. Some insider shares would stay locked well beyond 180 days and might not be freely sellable until mid-2027. The offering would also mix new shares that raise cash for the company with a secondary piece where current holders sell stock they already own.

Bankers have discussed a $1.5 trillion valuation, and The New York Times has reported the offering could value the company at $2 trillion. That range matters because your exit plan should be built before the price is known, not after the market moves.

Price the two decisions separately

Use three tests: price control, liquidity certainty, and cost. Price control asks whether you choose the sale price. Liquidity certainty asks whether the sale will actually happen. Cost includes lost upside, tax cost, and the risk of selling into a weak market.

• Day-one secondary sale: You accept the price set for the deal, but the sale is part of the offering, so liquidity is high. The price risk is selling before the public market has fully priced the company, which can leave money on the table after a strong debut.
• Hold to the later unlock: You can sell in the open market after restrictions lift, but liquidity is lower until that date. A tiered structure can push some shares into a much later window. The main cost is carrying company risk while waiting for a better price.
• Use a 10b5-1 trading plan: A 10b5-1 plan is a prearranged schedule that determines the size and dates of later sales ahead of time. You set the schedule, not the market price. The tradeoff is flexibility: you may sell into a weak market or miss a strong one because the plan is already running. Anthropic has weighed a policy where ordinary employees would follow predetermined 10b5-1 trading plans after the listing.

Do not try to pick the best price. Match each sale to the kind of certainty you need. A day-one sale gives you cash before the market has a chance to move. A later sale gives you more price control, but only if the shares are actually unlocked and you are allowed to sell them.

Build the two-date plan before the stock moves

Draw two boxes on the whiteboard. Box one is the offering date. Box two is the later unlock date. Decide what you will sell in each box before the IPO, not after the stock starts moving.

For box one, ask whether you need cash now. If yes, sell a small amount in the secondary offering. If no, leave more shares for the later unlock. Sell only enough to cover a real need, not to chase a price you cannot control.

For box two, model the post-lockup sale as a separate decision. Set a target range, a minimum sale, and a floor for selling if the stock falls hard. If the company requires a 10b5-1 plan, follow the schedule. If it does not, use one only when you want to remove emotion from the sale.

Check whether a 10b5-1 plan has already set your amount and timing. If it has, confirm the schedule still fits your cash needs, tax situation, and risk tolerance. If it has not, write the schedule before the unlock date. If the plan allows changes, review it later, adjust the amount, and sell without guessing on the day.

Employee liquidity is the real prize, but it arrives in pieces. Read the plan documents before you assume every share is yours to sell on day one. The documents will show which shares are in the offering, which are locked, and which have a trading plan.

The two-unlock exit plan: decide the day-one secondary sale before pricing, model the post-lockup sale as a separate decision, and check whether a 10b5-1 plan has already set the amount and timing.