my god I wish my company had hired you to explain this to us instead.... they hired all these fancy people and I was falling asleep with all their fancy words you got straight to the point. thank you!
I've looked at a lot of online content about this and how to calculate the ordinary income portion of the profit and that graphic the best explanation that I've seen so far. Thanks!
I believe the retirement crisis will get even worse. Many struggle to save due to low wages, rising prices, and exorbitant rents. With homeownership becoming unattainable for middle-class Americans, they may not have a home to rely on for retirement either.
So, to take advantage of the lowest tax rate, it would make sense to hold the stocks for 1 (from the purchase date) or 2 years( from the offering date)and then sell them only if the actual price of the share increases in value or goes beyond the offering price. So I would say ordinary income has a higher tax rate than Long-term capital gain?
To your last question first: Yes, ordinary income is generally taxed at a higher rate than long-term capital gains. So strictly from a tax perspective, if the stock price went up during the offering period, the best tax treatment is after you've held the stock for 1 yr from purchase AND 2 yrs from the offering date. BUT if the stock price went down during the offering period, it can actually be worse to hold it past those two dates b/c the amount that gets treated as ordinary income goes up. All that said, the main consideration for trying to hold the stock for that length of time should be based on if you believe in the stock/company itself. The potential tax savings can easily be wiped out by a dip in the stock price.
Thank you for the clear example! I have a question for a different situation: If the price was $15 on the offering date and dropped to $10 on the purchase date, then I sold it at $20 after 2 years from the offering date, how much will become capital gain? $5 or $10?
So to simplify if I sell before two years i'm taxed on the discount plus the look back. After two years I'm only taxed on the discount. Either way the discount is taxed at ordinary income tax rate while the stock is taxed at normal capital gains rates whether it be STCG or LTCG. Is this correct? If the above is correct it seems like if the stock price went down over the ESPP period it would be a good idea to consider selling before the two-year window because you didn't gain any look back advantage. Edit: just rewatched @08:12 that my second statement is explained
That sounds mostly correct. Sorry to sound nitpicky, but I want to clarify for anyone else reading this. If you sell before it becomes qualifying: - The total spread (stock price on the purchase date - your purchase price) is taxed as income. - Any difference relative to the price on the purchase date is capital gain/loss. Long-term if > 1 year from the purchase date. Once it's qualifying: - Any gain from your purchase price of up to the discounted % (usually 15%) of the price at the beginning of the offering period is taxed as income. - Any gain above that is a long-term capital gain - If you sell at a price lower than you bought it, you don't realize any income & have a long-term capital loss. So you're right that if the stock went down during the offering period, it can potentially be worse to hold on past the two years b/c the amount that can be taxed as income is 15% of the higher beginning stock price.
Very helpful. My company has 4 purchase periods within each offering period. Have a doubt how does the look back apply during the 2nd purchase period - does it look back all the way back to the offering date or the start date of the 2nd purchase period?
question - if you buy shares in ESPP why would your companies payroll take ESPP tax repayment out of your paycheck? Wouldn't you only pay taxes when you sell the the stock ? Wouldn't this mean your being double taxed ?
There aren't any taxes related to ESPP withheld from your paycheck, just the cash being put aside to buy your company stock on the purchase date. You're correct that you don't realize any taxes until the year that you sell the stock. Did I explain that OK?
The picture helped a lot. So does that mean if it's $15 on the offering date and $10 purchase date, it wouldn't make a difference cashing out after 1 year?
Right, that's the scenario I mention at 8:15 where holding past the 2 years from offering is actually treated worse from a tax perspective b/c more would be considered income and not long-term capital gains. Quick clarification: it's not just after 1 year, but 1 year from purchase + 2 years from offering that this happens. Glad to hear this helped!
If ESPP fund is after tax fund, W2 Box 1 should not be included ESPP fund. So only at the time selling ESPP, the related oridinary income tax and Capital Gain tax need to be calculated.
So if the share price value goes down more than the discount, let’s say $5, then it doesn't matter if it is a disqualifying disposition or a qualified disposition, right?
It's still treated a little differently between the two. In a DD, you'd still realize $6.50 of income for the original discount ($15 - $8.50) + a $10 capital loss ($15 - $5). Note that capital losses can offset income, but it's limited to $3K a year and the rest gets carried forward to future tax years. In a QD, you would only have a long-term capital loss of $3.50 ($8.50 - $5).
If I hold the stock for 2 years, how do I claim the offset additional tax I have already paid for the portion between 10 to 15. I assume that during the purchase date year, when I file taxes - my company reports the 8.50 to 15 as income right ??
So are you saying that if your numbers 10 and 15 are swapped ($15 on offering/start date and $10 on purchase date) then you would pay less taxes between 1-2 years than you would keeping it 2 or more years? I don’t understand how or why you would be taxed more.
That's correct. Once it becomes qualifying, it will always calculate the income portion using the offering date price instead of the purchase date. It's wildly confusing, even for many financial / tax pros. I made a visual of how it works in both scenarios, posted on LinkedIn: www.linkedin.com/posts/mikezung_confused-about-how-your-espp-is-taxed-youre-activity-7005624126816100352-uZdh
In the context of how ESPP stock is taxed, dividends don't factor in. Dividends are taxed in their own way when they're paid & you can't manipulate that timeline in any way. The decision whether to hold vs. sell your company stock should be more about how much you have tied up in your company + the expected total performance, dividends being a part of that. A good test is asking yourself "if you had $X, would you go buy your company stock with that money?".
I retired (100% Normal S.S.) in 2022. Have 5 years (2018 to 2022) of ESPP at cost basis of $36,000 ($7,200 ave. X 5 years). Current stock value is $136,000. Don’t need to sell, but wanted to sell over a few years to minimize taxes. Should i ladder the sales to take advantage of the 2 year long-term period?
I can't answer for you specifically b/c there are a lot of other factors to consider for that type of question. A few considerations: - Taxes should inform, but not drive a decision to sell. A relatively small dip in stock price easily negates tax savings - Most of this is already past the qualifying period, so spreading sales out for tax reasons only matters if the total long-term gains would trigger the additional 3.8% NIIT or go into the 20% LTCG bracket. - For the ones that haven't reached 2 years, look to see what the ESPP did during the offering period. If it went down, it's actually better from a tax perspective to sell it before you hit the 2-year mark. Hope that all helps!
my ESPP is subject to a 1 year holding period after the purchase date - is that some new requirement or just specific to my company? I looked into doing it but didn't because of this holding requirement - I didn't trust the share price to hold above what the purchase price is (the stock looks like it trending down despite good EPS)
Generally yes, but it doesn't show up until the year in which the stock is sold since the amount that is considered income depends on how long it was held.
@Java Wealth Is there any good reason to purchase DSPP (direct stock purchase plan) as opposed to ESPP? My son just got a job in a FAANG that offers DSPP but it offers no discount. He already has exposure to the company through normal 401k fund allocations (over 6%), and through his Robinhood (no brokerage fee). Is it worth it for him in any way to make DSPP purchases? Thank you.
Good question. There are a couple of ways to calculate it. Here's how I think about it: - $6,000 to buy shares at $8.50 (discount price) = 705.88 shares - 705.88 * $15 (current value) = $10,588 - $10,588 - $6,000 = $4,588 gain
My W2 shows ESPP amount X in box 14. My broker statement just shows cost basis(not adjusted) and TurboTax says that adjustment is normal for ESPP. Do I need to enter my ESPP amount in W2 for adjustment?
Sorry, I can't give any specific advice on how to fill out your return. Here is an article that may be helpful: www.forbes.com/sites/brucebrumberg/2021/03/23/6-big-tax-return-errors-to-avoid-with-employee-stock-purchase-plans
Step by step video with visuals on exactly what you're talking about. Not my video but literally watched it myself earlier today. th-cam.com/video/DzVonqRwXqY/w-d-xo.html
my god I wish my company had hired you to explain this to us instead.... they hired all these fancy people and I was falling asleep with all their fancy words you got straight to the point. thank you!
I've looked at a lot of online content about this and how to calculate the ordinary income portion of the profit and that graphic the best explanation that I've seen so far. Thanks!
I appreciate that. I'll admit I was pretty happy w/ that visual too :).
Thank you for the visual. After several videos I was so confused on the tax implications but the graphic made complete sense.
This is the best ESPP explanation I have seen on TH-cam
Thank you for this, it was very helpful and you did a great job breaking the ESPP process down!
I believe the retirement crisis will get even worse. Many struggle to save due to low wages, rising prices, and exorbitant rents. With homeownership becoming unattainable for middle-class Americans, they may not have a home to rely on for retirement either.
8:15 - exactly what I'm looking for in this time where most tech stocks have been going down. Thank you!
Bestestest explanation so far 🎉
always learn the stuff about stocks so much better when I look at your vides. Thanks for doing these!
Excellent explanation, very clear and easy to understand. Thank you!
This was so helpful, thank you so much!!! :) My first ESPP plan so this was so helpful for figuring out when I should sell them.
Glad it was helpful!
This helped a lot. thank you :)
Really straight forward explanation! Thanks
The chart is pretty amazing, thank you very much. I will subscribe your channel.
Enrollment just started. This was helpful. Thank you.
Glad to hear it, thanks!
great visual aid. easy to understand
I appreciate that!
Great video!
At 5:12, why is cost basis the blue line and not the 8.50 line? Thanks!
So, to take advantage of the lowest tax rate, it would make sense to hold the stocks for 1 (from the purchase date) or 2 years( from the offering date)and then sell them only if the actual price of the share increases in value or goes beyond the offering price. So I would say ordinary income has a higher tax rate than Long-term capital gain?
To your last question first: Yes, ordinary income is generally taxed at a higher rate than long-term capital gains. So strictly from a tax perspective, if the stock price went up during the offering period, the best tax treatment is after you've held the stock for 1 yr from purchase AND 2 yrs from the offering date. BUT if the stock price went down during the offering period, it can actually be worse to hold it past those two dates b/c the amount that gets treated as ordinary income goes up.
All that said, the main consideration for trying to hold the stock for that length of time should be based on if you believe in the stock/company itself. The potential tax savings can easily be wiped out by a dip in the stock price.
Thank you for the clear example! I have a question for a different situation: If the price was $15 on the offering date and dropped to $10 on the purchase date, then I sold it at $20 after 2 years from the offering date, how much will become capital gain? $5 or $10?
So to simplify if I sell before two years i'm taxed on the discount plus the look back. After two years I'm only taxed on the discount. Either way the discount is taxed at ordinary income tax rate while the stock is taxed at normal capital gains rates whether it be STCG or LTCG. Is this correct?
If the above is correct it seems like if the stock price went down over the ESPP period it would be a good idea to consider selling before the two-year window because you didn't gain any look back advantage.
Edit: just rewatched @08:12 that my second statement is explained
That sounds mostly correct. Sorry to sound nitpicky, but I want to clarify for anyone else reading this.
If you sell before it becomes qualifying:
- The total spread (stock price on the purchase date - your purchase price) is taxed as income.
- Any difference relative to the price on the purchase date is capital gain/loss. Long-term if > 1 year from the purchase date.
Once it's qualifying:
- Any gain from your purchase price of up to the discounted % (usually 15%) of the price at the beginning of the offering period is taxed as income.
- Any gain above that is a long-term capital gain
- If you sell at a price lower than you bought it, you don't realize any income & have a long-term capital loss.
So you're right that if the stock went down during the offering period, it can potentially be worse to hold on past the two years b/c the amount that can be taxed as income is 15% of the higher beginning stock price.
Very helpful. My company has 4 purchase periods within each offering period. Have a doubt how does the look back apply during the 2nd purchase period - does it look back all the way back to the offering date or the start date of the 2nd purchase period?
Nicky explained... 👍
question - if you buy shares in ESPP why would your companies payroll take ESPP tax repayment out of your paycheck? Wouldn't you only pay taxes when you sell the the stock ? Wouldn't this mean your being double taxed ?
There aren't any taxes related to ESPP withheld from your paycheck, just the cash being put aside to buy your company stock on the purchase date. You're correct that you don't realize any taxes until the year that you sell the stock. Did I explain that OK?
The picture helped a lot. So does that mean if it's $15 on the offering date and $10 purchase date, it wouldn't make a difference cashing out after 1 year?
Right, that's the scenario I mention at 8:15 where holding past the 2 years from offering is actually treated worse from a tax perspective b/c more would be considered income and not long-term capital gains.
Quick clarification: it's not just after 1 year, but 1 year from purchase + 2 years from offering that this happens.
Glad to hear this helped!
If ESPP fund is after tax fund, W2 Box 1 should not be included ESPP fund. So only at the time selling ESPP, the related oridinary income tax and Capital Gain tax need to be calculated.
Is ESPP after tax fund or before tax fund ?
Is there ever a good time to cash out of the ESPP?
In your example, Is the $6k that is held in escrow added to your income on your W2? Thank you.
Yeah, that's just regular old income.
So if the share price value goes down more than the discount, let’s say $5, then it doesn't matter if it is a disqualifying disposition or a qualified disposition, right?
It's still treated a little differently between the two.
In a DD, you'd still realize $6.50 of income for the original discount ($15 - $8.50) + a $10 capital loss ($15 - $5). Note that capital losses can offset income, but it's limited to $3K a year and the rest gets carried forward to future tax years.
In a QD, you would only have a long-term capital loss of $3.50 ($8.50 - $5).
Hello!
In this example, are ether or these plans qualified or non-qualified plans?
This is describing qualified plans
If I hold the stock for 2 years, how do I claim the offset additional tax I have already paid for the portion between 10 to 15.
I assume that during the purchase date year, when I file taxes - my company reports the 8.50 to 15 as income right ??
No taxes are withheld or income realized until the shares are sold. All of it happens when you sell the shares. Thx for the question, hope this helps!
So are you saying that if your numbers 10 and 15 are swapped ($15 on offering/start date and $10 on purchase date) then you would pay less taxes between 1-2 years than you would keeping it 2 or more years? I don’t understand how or why you would be taxed more.
That's correct. Once it becomes qualifying, it will always calculate the income portion using the offering date price instead of the purchase date. It's wildly confusing, even for many financial / tax pros.
I made a visual of how it works in both scenarios, posted on LinkedIn: www.linkedin.com/posts/mikezung_confused-about-how-your-espp-is-taxed-youre-activity-7005624126816100352-uZdh
Wouldn’t the cost basis be the $8.50 and not $15?
Is it better to hold the stock if there are dividends offered?
In the context of how ESPP stock is taxed, dividends don't factor in. Dividends are taxed in their own way when they're paid & you can't manipulate that timeline in any way.
The decision whether to hold vs. sell your company stock should be more about how much you have tied up in your company + the expected total performance, dividends being a part of that. A good test is asking yourself "if you had $X, would you go buy your company stock with that money?".
I retired (100% Normal S.S.) in 2022. Have 5 years (2018 to 2022) of ESPP at cost basis of $36,000 ($7,200 ave. X 5 years). Current stock value is $136,000. Don’t need to sell, but wanted to sell over a few years to minimize taxes. Should i ladder the sales to take advantage of the 2 year long-term period?
I can't answer for you specifically b/c there are a lot of other factors to consider for that type of question. A few considerations:
- Taxes should inform, but not drive a decision to sell. A relatively small dip in stock price easily negates tax savings
- Most of this is already past the qualifying period, so spreading sales out for tax reasons only matters if the total long-term gains would trigger the additional 3.8% NIIT or go into the 20% LTCG bracket.
- For the ones that haven't reached 2 years, look to see what the ESPP did during the offering period. If it went down, it's actually better from a tax perspective to sell it before you hit the 2-year mark.
Hope that all helps!
If for partial sales, would IRS treat taxable proceeds using First in, first out method? @@JavaWealth
my ESPP is subject to a 1 year holding period after the purchase date - is that some new requirement or just specific to my company? I looked into doing it but didn't because of this holding requirement - I didn't trust the share price to hold above what the purchase price is (the stock looks like it trending down despite good EPS)
This didn’t mention how the income is reported. Isn’t the discount reported on the w2?
Generally yes, but it doesn't show up until the year in which the stock is sold since the amount that is considered income depends on how long it was held.
@Java Wealth Is there any good reason to purchase DSPP (direct stock purchase plan) as opposed to ESPP? My son just got a job in a FAANG that offers DSPP but it offers no discount. He already has exposure to the company through normal 401k fund allocations (over 6%), and through his Robinhood (no brokerage fee). Is it worth it for him in any way to make DSPP purchases? Thank you.
Hi how do you calculate the 4500 gain?
Good question. There are a couple of ways to calculate it. Here's how I think about it:
- $6,000 to buy shares at $8.50 (discount price) = 705.88 shares
- 705.88 * $15 (current value) = $10,588
- $10,588 - $6,000 = $4,588 gain
My W2 shows ESPP amount X in box 14. My broker statement just shows cost basis(not adjusted) and TurboTax says that adjustment is normal for ESPP. Do I need to enter my ESPP amount in W2 for adjustment?
Sorry, I can't give any specific advice on how to fill out your return. Here is an article that may be helpful: www.forbes.com/sites/brucebrumberg/2021/03/23/6-big-tax-return-errors-to-avoid-with-employee-stock-purchase-plans
Step by step video with visuals on exactly what you're talking about. Not my video but literally watched it myself earlier today.
th-cam.com/video/DzVonqRwXqY/w-d-xo.html
ESPP taxes are weird. Selling at disqualifying disposition can make more sense in a declining market.