Your company is going public.
Going public is the event most people picture when they imagine the windfall. It’s also the one with the most moving parts, where the decisions on your options, your taxes, and your concentration get made on a clock you don’t control.
The AMT cliff, and the 10b5-1 plan you may need in place first.
An ISO exercise can trigger an alternative minimum tax bill even when you’ve sold nothing. And if you hold material nonpublic information, you generally can’t sell the day the lockup ends. A 10b5-1 plan is how insiders and many employees sell legally on a schedule. It only protects you if you set it up at a time when you hold no inside information, and your company’s policy may add its own limits. Then a cooling-off period has to pass before the first trade. The plan has to be in place well before you want the money, and a plan written under deadline pressure tends to encode whatever you were feeling that week.
We work the event in the same order we work everything else.
Protect. First we map what’s actually exposed. The AMT math on any exercise, the timing on a 10b5-1 plan, so it is in place before you need to sell, the lockup mechanics, and how much of your net worth is riding on one stock you’re not allowed to touch yet.
Subtract, then align. We clear the noise and point what remains in one direction, so your exercise strategy, your tax plan, and your sell schedule are coordinated instead of improvised.
Build. Then we build the plan for the money. A sell schedule that respects the rules and your concentration, what to do with the proceeds, and whether QSBS changes the math, with dates attached so nothing waits on you.
The Plan is $5,000 flat, built for delivery within 30 days of kickoff, and backed by the Plan Promise: a full refund, for any reason, if you ask in writing within 30 days after delivery. You keep the plan.
See what’s included and how pricing works →When should I exercise my options?
It depends on your basis, the spread, the AMT it would trigger, and what you can actually cover in cash, which is exactly why it needs to be modeled rather than guessed. The wrong year, or the wrong size, is where the avoidable tax bills come from.
Can I sell the moment the lockup ends?
Often not freely. If you hold material nonpublic information, you can’t sell until it’s public. The exception is a 10b5-1 plan you set up before you had that information, once its cooling-off period has run. The time to set it up is well before the date you’re counting on. If you hold no inside information and your company’s trading window is open, you generally don’t need a plan. Check your company’s trading policy before you sell.