// Expertise
Liquidity Events
Your company just announced something that changes your financial picture. The window to get things right is small. The potential tax consequences may be big.
// THE CLOCK IS RUNNING
Something Big Is Coming.
Now What?
01
You just found out. A tender offer window opened. An S-1 was filed. An acquisition is in the works. After months or years of holding illiquid equity, there's suddenly a number attached to it — and a deadline attached to the number.
This should feel like good news. Mostly it feels like a fire drill. How much should you sell? What are the tax implications? How does this interact with the rest of your financial picture? And why does the decision window always close before you've had time to think?
You're not behind. But the decisions you make in the next few weeks may have more financial impact than anything you do for the rest of the year.
// WHICH EVENT ARE YOU FACING?
Three Events, One Problem
02
Different mechanics. Same underlying challenge: illiquid equity becomes liquid, and you have a limited window to act.
Tender offers
Pre-IPO Liquidity Window
Your company opens a window for employees to sell shares. You choose how many, at what price, and from which tax lots. Miss the window, and you're back to waiting — with no guarantee another one comes.
IPOs & Direct Listings
Going Public
Lockup periods restrict selling for 90–180 days. The planning starts well before the listing: exercise timing, concentration exposure, Day 1 strategy — and the stakes compound if the stock swings while you're locked up.
mergers & Acquisitions
Being Acquired
The payout may be cash, acquirer stock, or a mix — each with different tax treatment. Receiving acquirer stock just swaps one concentration problem for another, with a ticker you didn't choose.
// what makes this different
One Shot. No Do-Overs.
03
Many financial decisions can be adjusted after the fact. You can rebalance a portfolio. You can file an amended return or extend a deadline. You get multiple cycles to refine.
Liquidity events aren't like that. They're singular, time-bound, and largely irreversible. And the real cost isn't the obvious mistake — it's the interactions people miss under time pressure:
These are the scenarios we encounter most often — smart people who who are top performers in their organizations, potentially leaving significant money on the table if they make the wrong choice.
// why prospero
We've Been In Your Seat
04
Prospero's advisors are former tech professionals. We've held illiquid equity, watched 409A valuations swing, and made exercise decisions under uncertainty. When your company announces a tender offer or files an S-1, we've been in your seat.
// what we build
The mechanics of each event type are learnable. What's hard to learn from a blog post is how these events interact with everything else — your concentrated position, your tax situation, your vesting schedule, your career timeline, and your goals.
That integration is what we build. Ideally before the event, but effectively during it when clients come to us mid-window.
// NEXT STEPs
If your company has announced a liquidity event — or one is on the horizon — the best time to start planning was before the announcement. The second best time is now.
