I did, but for most of my tenure the company’s valuation was pretty low, meaning my original grants were pennies and the company’s fair market value was depressed, so taxes were manageable.
The way I thought of it when exercising was who cares if I lost a few thousand buying lotto tickets.
Some of my former coworkers didn’t exercise regularly and are now semi golden handcuffed*
*The company extended the exercise period to 10y shortly after I left.
Yes, I exercised regularly so my tax bill was manageable.
The company's trajectory looked more like a hockey stick, so my taxes were negligible until later years — and by then my original grants were exercised, leaving only my relatively expensive refreshers with a lower delta to fair market value
I spent most of my 20s (7+ years) at a startup that is currently a “unicorn”, and consequently have an ok amount of shares locked up in the same situation.
As the company’s valuation grew higher and higher the equity grants became significant lower. It was balanced out by my pay becoming more and more competitive vs other large companies. But eventuality I decided ~80% was as fully vested as I’ll ever be — Not to mention my boss and commute were driving me insane — and because I joined so early my options were cheap enough to exercise over time, so I called it quits.
Now I’m at a boring public company, commute via train, but with no hope of ever making big $$$ someday.
My overall mental health seems a lot better now. I hope I made the right call letting go of that 20%.
The way I thought of it when exercising was who cares if I lost a few thousand buying lotto tickets.
Some of my former coworkers didn’t exercise regularly and are now semi golden handcuffed*
*The company extended the exercise period to 10y shortly after I left.