I have a large percentage my total investment as employer stock either granted through RSUs or through ESPP (Employee Stock Purchase Plan). I figured there are two many ways of reducing the tax burden as I diversify:
1. Bundle up sales of the stock with sales of other stock I have which has lost money. In that case, I should sell the company shares with **highest cost basis** such that I am able to get rid of the most total dollar value of stock with minimum capital gains.
2. Donate shares to charity. If doing this, donate the company shares with **lowest cost basis**
And lastly, do the above steps sooner rather than later, even considering tax implications.
For the future, I would guess the recommended action to be: sell any granted stock right as it is granted such that capital gains is effectively 0 and I can diversify tax-free?