Trying to understand how you decide to sell shares
Where is the don't sell ever option?
If you would use your cash to buy company shares, than hold. The only difference is special tax treatment for long term gain on espp.
Wait so I’ve heard both 1 year and 2 year comments for capital gain vs long term... insight?
It is 2 years from the start of the period. If you get espp every 6 months for e.g. you would have to hold it 18 month after you got the shares. 18+6(to the start of period)=2 years
If you are just talking about buying stock on open market, it is 1 year from when you purchase it.
For my particular situation, I hold for the long term and when an arbitrary ratio of my net worth becomes disproportionately high in favor of my company, I sell RSUs that are in the long term capital gains picture and re-invest. Hate to have all of my eggs in one basket.
The amount you get after selling the ESPPs. It tax reduced from that?
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RSU is taxed as income at vesting. The bulk of the value will not qualify for long-term capital gains if you hold onto it.
It's equivalent to buying it. If you hold for a year then any further gains are taxed as long term. ESPP is also taxed as income for the part that we get a discount on, and you have to hold it for 2 yrs to qualify for long term capital gains on any FUTHER gains on it. No matter what the discount part is taxed as income.
If company stock generally goes up or buy backs are strong then I would hold stock, if the company stock doesn’t really appreciate then sell fast. But it’s risky because you are over invested in your employer potentially (income dependent on them and stocks based on how the companies doing)