re: RSU strategies

You are thinking about it correctly, that is my current strategy.

I went 7 years without selling a single share and the stock has massively appreciated, so now I’m stuck with a huge chunk of stock and a huge tax bill. Trading restrictions make selling this stock tough.

I’ve been selling all new RSU grants since 2021, but still holding the ones prior.

I think it all comes down to risk tolerance. My decision in the early days netted me huge returns (and now huge taxes). The correct move is to sell immediately, but I rolled the dice and so far it worked. But working double time this year to reduce my exposure.