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 depress

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.