If you buy ESPP through your company, do you sell immediately every 6-month period?

likehelpful
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Manager 1 doesn’t understand how ESPP works lol

almost always sell immediately then repurchase other stocks and diversify.

the 15% discount or whatever discount you get, the IRS taxes as ordinary income. you only pay taxes on the discount, not the entire stock purchase.

only time I keep the stake is if I feel the stocks are gonna jump up in price within the next 3-4 months. i wait for the growth then sell. the 15% is free money and i treat it like a bonus. if your company gave you a 15% bonus for free, you go look at options to sell it

likesmart

Not selling immediately. My company’s stock has increased so much it’d be stupid to buy anything else.

No. I try to wait over 1 year for long term gains rate

likefunny

That's not how it works

like

How much faith do you have in the future of the company? If the future looks mid, sell. If it looks rosy, keep.

like

You can hold it until the expiration date to exercise

like

Yes. If you sell immediately there’s either a small capital gain or loss depending on if the stock is up or down for the day. Typically the amount is already considered ordinary income and stock has been sold to cover taxes before you get it. Do what works best for your situation and risk tolerance.

like

Our ESPP has an 18-month RSU lockup. Selling prior to the 18 months is penalized.

I hold 1.5k shares of general stock. I just take my dividends and reinvest it through ESPP to continue to grow the position but don't spend more than that.

It'd a 5% early liquidation fee and then you get dinged on the taxes as ordinary income not capital gains per IRS. Which at any modest person is easily 24-32% of your gains.

I just joined the ESPP program, I however think it makes sense to put my money in my company for the long term. I see how it is interesting to sell just after getting them, you only pay taxes on the % discount, but if one doesn't have immediate cash needs and your company has good prospects, it makes sense to hodll

no -__- it makes sense to diversify. do you see warren buffett buying stock in only ONE company?

the key to surviving economic downturn is diversity. never put all your eggs in one basket.

unless stocks are low and you can tell theyll bounce back in 3-4 months then hold and sell. never hold on for too long. if stocks are high or normal, then sell immediately and repurchase other stocks or crypto.

diversify your portfolio. if not, then best of luck

I sell if I need the money. Last time sold it to buy a vehicle. Next batch I won’t sell, because I have no need for the money and the company is on a good path. However, make sure you have some savings elsewhere in case the stock crashes, so you don’t lose it all.

I sell immediately

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