By the Time the Money Shows Up, the Work Is Done.

The people who keep a fortune when it lands all at once are almost never the smartest ones in the room. They are the ones who did the boring work before the money was real, back when it was still theoretical and nobody was excited. None of it is clever, and that is the point.

Start with the one that sounds too basic to bother with. Find out exactly what you own. Not the share count. The kind. Restricted units that settle the day the company goes public get taxed automatically, on a day you do not pick. Options work differently, and usually let you choose the day yourself, which is a lever. You cannot pull a lever you did not know you were holding. Which one you actually hold decides everything after it, and plenty of people cannot say for certain. So before any of it is worth a dollar, read the actual grant. The document, not the version of it in your head.

The tax is the part everyone assumes is handled. It is not. Your company usually holds back a stack of your shares to cover it, and that feels like the end of it. But what they hold back usually comes out at a flat rate the government sets for this kind of pay, and it has nothing to do with what you actually owe. For most people at this level, what you owe is the bigger number, and the difference is real money that is still yours to pay. That is not a surprise waiting in April, and some of it can be due sooner as estimated tax. It is arithmetic you can run now. So run it now with your tax preparer, and decide where the shortfall comes from before the bill has your attention.

The one that catches people is a tax on money you might never keep. With restricted units, you are taxed on what the shares were worth the day they became yours. If you are locked out of selling and the price slides across those months, the tax on that income holds at the high number while the shares do not. So do not assume you can sell the shares to pay the tax you owe on them. Assume you might not, and know where the cash comes from if they cannot be the ones to cover it.

All of this is boring, and it is boring at the exact moment your life finally feels like it is happening. Nobody wants to spend that week reading a grant agreement. I get it. It is also the one week you cannot afford to be reading it for the first time.

Talk Friday.

— Mateo