When is a good time to sell RSUs and why?
1. Right when they get vested 2. After 1 year of vesting (to avoid short term capital gains tax) 3. Never.

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If you sell the day you vest, there’s no gain. I sell at vest (although I have some older holdings that I am keeping) because I don’t want to have more company stock.

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Immediately after and dump it into s&p is the optimal way to

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I wouldn't say there's an "optimal" way . There are a ton of different factors that would impact best path forward for someone

I would sell as soon as possible after they vest.

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So it depends on what your plan and/or goals are, and how the RSU’s play a part in your overall investment strategy. If you believe in the company that you work for, and believe that the shares will perform well long term, keep them. If you have a negative outlook of the company that you work for, I would suggest that you first reevaluatie why you work there and your long-term prospects, if you have a negative sentiment, prior to selling them.

In terms of timing, there are no immediate short-term, long-term gain considerations; when the shares vest, they are included as ordinary income in that year. However, if you dispose of the shares the same day, or next week, within one year, you may be subject to short-term capital gain/loss. Your cost-basis is the value of the shares when they vest. Over 1 year, they become long-term capital gain/loss.

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1. Don’t want an ERON situation, so sell all company stocks immediately upon vesting even if it costs a bit in the long run.

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Right after vesting. RSUs are taxable as ordinary income at vesting time and arrive with the basis of the price at time of vesting, so if you sell right away there's no tax.

You don't want to be holding individual stocks any longer than you have to. Reinvest in a diverse index allocation you can hold for the long term. :)

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2 seems like a good answer to me in general. Better tax treatment, some exposure but not too much to your company stock.

If that was your only investment it might be wise to sell some early and diversify. If you are already well diversified you certainly don't have to sell even at a year if you don't want to recognize the gains.

Correct. If you sell the date of vest the gain is zero.

FMV on vest = ordinary income no matter what.

Edit: you don’t decide to buy RSUs, they are granted to you in exchange for employment services. If you want to buy company stock… you can just buy it.

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