Taking money off the table

Growing up around people who lost everything, job and savings, working at Enron, you should take all the money they’ll let you. You are structurally long your company already, because if they struggle you could lose your job. Diversify your wealth away from that concentrated position as much as possible if you’re offered a fair price.

Would you apply that similarly to RSUs at a public company as well? i.e. always sell your stock grant and diversify regardless of the company?

If they gave you cash instead, would you use it to buy stock in the company? That should answer the question.

I disagree. The answer for me is always half. And then next time, half again. Always take some out and leave some in, and an easy way to hedge your bets is to make both amounts half.

Yes, same principle. And with RSUs you can be even more confident that you’re selling at market rate than you can with a tender offer for illiquid equity.

You are welcome to your own perspective. I just want to point out to others that having even half of what was presumably a large fraction of your net worth in any single company is not considered well diversified, especially when you rely on that same company for your paycheck.