Poll: ESPP participants. Do you typically take the money and run or hold for cap gaps treatment.

[sd_bear]

I can contribute 10% gross salary for a 15% discount.

Personally I always sell the ESPP immediately (assuming we aren’t in a blackout period). The way I see it, that 10% is my salary, and I don’t want to mess around with it and possibly end up making less than what I would have made had I not been in the ESPP at all. Luckily the stock more than doubled from the purchase price so I made out like a bandit anyway.

My stock options, however, I hold on to. Since it’s money I never had to begin with I’m much more comfortable taking a risk with it.

[pbnative]

I have an ESPP flip-it rule, because a 15% return makes me happy. Bird in the hand sorta thing. If I felt strongly about a rising stock price, I might hold some of it. (But of course, you have to be careful when you sell, making sure the sale is not based on any info you learned because you work there.)

[pbnative]

I have an ESPP flip-it rule, because a 15% return makes me happy. Bird in the hand sorta thing. If I felt strongly about a rising stock price, I might hold some of it. (But of course, you have to be careful when you sell, making sure the sale is not based on any info you learned because you work there.)

[pbnative]

I have an ESPP flip-it rule, because a 15% return makes me happy. Bird in the hand sorta thing. If I felt strongly about a rising stock price, I might hold some of it. (But of course, you have to be careful when you sell, making sure the sale is not based on any info you learned because you work there.)

[pbnative]

I have an ESPP flip-it rule, because a 15% return makes me happy. Bird in the hand sorta thing. If I felt strongly about a rising stock price, I might hold some of it. (But of course, you have to be careful when you sell, making sure the sale is not based on any info you learned because you work there.)

[pbnative]

I have an ESPP flip-it rule, because a 15% return makes me happy. Bird in the hand sorta thing. If I felt strongly about a rising stock price, I might hold some of it. (But of course, you have to be careful when you sell, making sure the sale is not based on any info you learned because you work there.)

[Doofrat]

If your stock doesn’t move much and is relatively safe, then I’d wait for the LT gains, but remember that the state (Ca.) still taxes you fully on it (I could be wrong about this, but unfortunately, probably not).

If you have options, you can exercise and sell those before selling the ESPP because you’ll get whacked on the ST gains anyway, that’s what I always try to do.

Of course my company had stock that was all over the place, so my perspective is different. I saw a lot of co-workers trying to save a some money on taxes get hit with AMT (buying options) or seeing the stock drop 50% before they sold their ESPPs or options.

So from my perspective with the volatile stock, if it’s a good time to sell, don’t think about the tax consequences.

[Doofrat]

If your stock doesn’t move much and is relatively safe, then I’d wait for the LT gains, but remember that the state (Ca.) still taxes you fully on it (I could be wrong about this, but unfortunately, probably not).

If you have options, you can exercise and sell those before selling the ESPP because you’ll get whacked on the ST gains anyway, that’s what I always try to do.

Of course my company had stock that was all over the place, so my perspective is different. I saw a lot of co-workers trying to save a some money on taxes get hit with AMT (buying options) or seeing the stock drop 50% before they sold their ESPPs or options.

So from my perspective with the volatile stock, if it’s a good time to sell, don’t think about the tax consequences.

[Doofrat]

If your stock doesn’t move much and is relatively safe, then I’d wait for the LT gains, but remember that the state (Ca.) still taxes you fully on it (I could be wrong about this, but unfortunately, probably not).

If you have options, you can exercise and sell those before selling the ESPP because you’ll get whacked on the ST gains anyway, that’s what I always try to do.

Of course my company had stock that was all over the place, so my perspective is different. I saw a lot of co-workers trying to save a some money on taxes get hit with AMT (buying options) or seeing the stock drop 50% before they sold their ESPPs or options.

So from my perspective with the volatile stock, if it’s a good time to sell, don’t think about the tax consequences.

[Doofrat]

If your stock doesn’t move much and is relatively safe, then I’d wait for the LT gains, but remember that the state (Ca.) still taxes you fully on it (I could be wrong about this, but unfortunately, probably not).

If you have options, you can exercise and sell those before selling the ESPP because you’ll get whacked on the ST gains anyway, that’s what I always try to do.

Of course my company had stock that was all over the place, so my perspective is different. I saw a lot of co-workers trying to save a some money on taxes get hit with AMT (buying options) or seeing the stock drop 50% before they sold their ESPPs or options.

So from my perspective with the volatile stock, if it’s a good time to sell, don’t think about the tax consequences.

[Doofrat]

If your stock doesn’t move much and is relatively safe, then I’d wait for the LT gains, but remember that the state (Ca.) still taxes you fully on it (I could be wrong about this, but unfortunately, probably not).

If you have options, you can exercise and sell those before selling the ESPP because you’ll get whacked on the ST gains anyway, that’s what I always try to do.

Of course my company had stock that was all over the place, so my perspective is different. I saw a lot of co-workers trying to save a some money on taxes get hit with AMT (buying options) or seeing the stock drop 50% before they sold their ESPPs or options.

So from my perspective with the volatile stock, if it’s a good time to sell, don’t think about the tax consequences.

[stansd]

I’ve done a good amount of thinking on this. I think the best strategy in general is to do a rolling flip…accumulate a years worth and then flip immediately once it hits the capital gains window. Upside is the certainty of lower taxes and the potential for gain from stock increases. Downside is that you are further exposed to the risk of the company you work for.

That’s the ideal: In my situation, I’ve also had a fair amount of exposure to my company’s performance via bonuses or options. Because of this, I’ve been flipping it immediately.

It’s all about your risk tolerance. The highest expected value will come from holding it a year, but you have to weigh that against your tolerance and the other risk exposure you have to the company.

One other thought: if you pay $80 for $100 worth of stock, 10% decline wipes out $10 of wealth. Your tax savings are someing like 10% *$20 = $2. $2 isn’t insignificant, but you take on a good amount of risk to save it.

Stan

[stansd]

I’ve done a good amount of thinking on this. I think the best strategy in general is to do a rolling flip…accumulate a years worth and then flip immediately once it hits the capital gains window. Upside is the certainty of lower taxes and the potential for gain from stock increases. Downside is that you are further exposed to the risk of the company you work for.

That’s the ideal: In my situation, I’ve also had a fair amount of exposure to my company’s performance via bonuses or options. Because of this, I’ve been flipping it immediately.

It’s all about your risk tolerance. The highest expected value will come from holding it a year, but you have to weigh that against your tolerance and the other risk exposure you have to the company.

One other thought: if you pay $80 for $100 worth of stock, 10% decline wipes out $10 of wealth. Your tax savings are someing like 10% *$20 = $2. $2 isn’t insignificant, but you take on a good amount of risk to save it.

Stan

[stansd]

I’ve done a good amount of thinking on this. I think the best strategy in general is to do a rolling flip…accumulate a years worth and then flip immediately once it hits the capital gains window. Upside is the certainty of lower taxes and the potential for gain from stock increases. Downside is that you are further exposed to the risk of the company you work for.

That’s the ideal: In my situation, I’ve also had a fair amount of exposure to my company’s performance via bonuses or options. Because of this, I’ve been flipping it immediately.

It’s all about your risk tolerance. The highest expected value will come from holding it a year, but you have to weigh that against your tolerance and the other risk exposure you have to the company.

One other thought: if you pay $80 for $100 worth of stock, 10% decline wipes out $10 of wealth. Your tax savings are someing like 10% *$20 = $2. $2 isn’t insignificant, but you take on a good amount of risk to save it.

Stan

[stansd]

I’ve done a good amount of thinking on this. I think the best strategy in general is to do a rolling flip…accumulate a years worth and then flip immediately once it hits the capital gains window. Upside is the certainty of lower taxes and the potential for gain from stock increases. Downside is that you are further exposed to the risk of the company you work for.

That’s the ideal: In my situation, I’ve also had a fair amount of exposure to my company’s performance via bonuses or options. Because of this, I’ve been flipping it immediately.

It’s all about your risk tolerance. The highest expected value will come from holding it a year, but you have to weigh that against your tolerance and the other risk exposure you have to the company.

One other thought: if you pay $80 for $100 worth of stock, 10% decline wipes out $10 of wealth. Your tax savings are someing like 10% *$20 = $2. $2 isn’t insignificant, but you take on a good amount of risk to save it.

Stan

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