Plan for your liquidity event before it happens.
A tender offer, an IPO, or an acquisition turns years of illiquid equity into a decision with a deadline — and a tax bill attached. We build the plan before the window, so you can execute calmly within it rather than reverse-engineer it under pressure.
// The Problem
The decision is rare, the deadline is real, and there’s no rerun.
A liquidity event is the moment that equity that was previously locked up — waiting for a tender offer, an IPO, or an acquisition — becomes sellable, usually inside a fixed window.
At some companies a tender offer comes around on a schedule, even twice a year, and starts to feel routine. For most people an IPO or an acquisition happens once.
Either way, equity that took years to build can turn into a taxable decision in a matter of weeks.
The hard part usually isn’t the headline number. It’s that the choices get made on someone else’s timeline — and most of them don’t come with a second take.
The goal isn’t to predict the price, it’s to be ready when the window opens.
// The Goal
A plan built before the window. Executed calmly within it.
Good liquidity planning means most of the decisions are made before the event — so the window is for executing a plan, not building one under a deadline.
That turns a singular, high-pressure moment into something closer to the routine the calmest holders already treat it as: a step that was mapped in advance and simply gets carried out.
// The Three Events
Three events. Each with its own window.
Liquidity tends to arrive in one of three forms — a tender offer, an IPO or direct listing, or an acquisition — and each carries a different window, a different tax profile, and a different set of decisions.
// Tender offer
Sell into a company-run window
A chance to sell some shares before any public listing — at some companies, on a recurring schedule. The decisions: how much to tender, and from which lots. Company-specific guides (such as the one for Anthropic) go deeper.
Often recurring
// IPO & direct listing
The once-in-a-company event
Going public restricts selling through a lockup for a set period, and the stock can move while you wait. The planning — exercise timing, a Day-1 plan, hedging locked shares — starts well before the listing.
Usually once
// Acquisition
Cash, stock, or a mix
An acquisition may pay you in cash, in the acquirer’s stock, or both — each taxed differently. Receiving stock can simply swap one concentrated position for another you didn’t choose.
One-time
// What We Do
Most of the work happens before the window.
A liquidity-event plan spans three phases — preparing before the event, executing during the window, and cleaning up after the proceeds land.
// Before the event
Set the table
Exercise and tax planning, pre-event gifting or charitable moves where they fit, and residency considerations.
// During the window
Execute the plan
Hedging locked-up shares and selling on a systematic, pre-set schedule — a 10b5-1 plan where you’re an insider.
// After it closes
Diversify the proceeds
Lot selection, setting aside the tax, and diversifying so one concentration doesn’t quietly become the next.
The specifics live on the event pages and in our concentrated-position toolkit — this is the shape of the plan, not the full tactic list.
// THE RISKS OF DIY
Decisions you can't undo.
Some financial decisions can be revised or revisited — you can rebalance, amend a return, or wait for the next cycle. Liquidity-event decisions are largely one-shot.
No take-backs on the offer
Once shares are tendered at the offer price, there’s no amended return that pulls them back.
No re-do on the price
If the stock falls while you’re locked up and you didn’t hedge, the price you could have protected is gone.
No unwinding the tax year
Exercise without modeling the AMT or the tax year, and the bill arrives with no way to reset the timing.
The risk quietly rebuilds
Acquirer stock held out of inertia can rebuild the single-stock exposure you just worked to exit.
// First principles
Plans are nothing; planning is everything.
— Dwight D. Eisenhower
// The Team
Advisors who’ve been through the window.
Prospero’s advisors are former tech and startup professionals who have experience navigating tender offers, IPOs, and acquisitions — not generalists reading from a script. Our team has navigated these kinds of decisions personally, and guided clients at companies like Stripe, Anthropic, and SpaceX with these decisions too.
// Next Step
Let’s build the plan before the window opens.
A first conversation is about your situation, not a sales pitch — what you hold, when an event is likely, and how to be ready before the decision is due.
// FAQ
Questions we get about liquidity events.
What is a liquidity event?
A liquidity event is when equity that couldn’t easily be sold — private-company shares, RSUs, or options — becomes sellable, usually through a tender offer, an IPO or direct listing, or an acquisition.
Should I sell everything when the window opens?
Not necessarily. How much to sell depends on how concentrated you are, your tax picture, and your goals; in many cases a plan sells in stages rather than all at once.
What is a lockup, and can I do anything during it?
A lockup is a period after an IPO when employees generally can’t sell their shares. In some cases locked shares may be hedged to manage the risk of a price decline before they can be sold, though hedging carries its own costs and risks.
How are the proceeds from an acquisition taxed?
It depends on what you receive. Cash is generally treated as a taxable sale, while a stock-for-stock exchange may be tax-deferred in certain structures. The treatment varies with the deal terms and your situation, so confirm with your tax advisor.
Do I need to plan before the event, or can you help during the window?
Ideally before — that is when the most options are available. In practice we often work with people mid-window, building the plan around the time that is left.
