I was counseled years ago to be VERY careful about these conversations. You can’t encourage, or come off as encouraging, any employee to exercise or not — if t

I was counseled years ago to be VERY careful about these conversations. You can’t encourage, or come off as encouraging, any employee to exercise or not — if the bet goes the wrong way (company succeeds but empmdidnt exercise or vice versa) you / the company could be sued and it’s an SEC violation. One thing you should do is support early exercise (meaning exercise any time, even before you’ve vested; company can repurchase and the same price any unvested shares if you leave). This is especially good for early hires when the price is extremely low and 83(b) means you avoid a tax bill until you sell. In later stage companies this doesn’t help as much though. I do agree with the author that comp secrecy is not just stupid but destructive.