Ask HN: Employees who exersised stock options: how did it go?

I had some in-the-money options. I operated on what you might call the principle of least regret. I wanted to get at least something from them, in case it went down. But I wanted to get more if it went up. So I sold part of my options when they were in the money. Then, after it went up some more, I sold some more. Then, after it went up some more, I sold some more. I finally sold it all in about five or six waves.

Could I have had more money if I had waited to sell? Sure... or I could have gotten nothing, if the stock had done something other than what it did.

Having worked at Google, I'm pretty sure that most of us only took stock because that was simply "how it was done"; it saves the company money versus paying you in cash (I guess! not an expert here). There is an infinite amount of paperwork that results from being paid in stock, and while it's obviously worth it for $200,000 a year on top of your base salary and bonus... it is still kind of a hassle. You have to file with the IRS your plan for selling shares (so they know you're not making insider trades), you can only access your money inside trading windows (unless you set up the aforementioned auto-sale or other trading plan), and your taxes become a $700 ordeal with tax professionals every year. Honestly, I just did my taxes myself and I messed them up one year. It takes the IRS 3 or so years to notice, and then one day you have a sternly-worded letter from the government demanding $60,000 immediately because your brokerage sent the IRS incorrect paperwork. Then you pay someone to fix that, then your state says "whoa, the IRS just got $60,000 from you! we want our cut!" and then you say "no no, those papers I mailed you a year ago show that they were wrong", then you wait a year... and get a $30 check in the mail because it turns out they owe YOU money. It's a big pain. My TL;DR is you don't know how much you owe, the government doesn't know how much you owe, and you will have to pay someone to take a guess that the IRS agrees with, and hope they agree. If they don't, be ready to pay even more money to persuade them that they are wrong.

I miss the days where I got a W-2 and filed a 1040EZ. It's ultimately worth it to take the stock, of course, but it's kind of a hassle. My advice is to find an accountant your first year at a FAANG and let them handle everything. Don't do it yourself.

My options? "Extinguished" in some "event" 18 years ago. My guess is that's the event where they screwed as many employees as they could.