Author Topic: Exercising Private Equity Options  (Read 89723 times)

mizzourah2006

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Exercising Private Equity Options
« on: September 13, 2022, 10:24:03 AM »
I am leaving a company and part of my compensation was a partial ownership in the company vesting over 7 years or immediately upon sale. We are still about 12 months from selling, but given the valuations the company is getting I want to exercise the options before I leave. One of the founders mentioned I might owe some taxes upon exercising the options. Do privately held company's shares get taxed at the Finance groups estimated valuation? If so, if it sells for less than that and the gains are taxed as ordinary income do I subtract the loss from my current year's income? Seems odd that you would owe taxes when there is no official market for the shares at this point. For all I know they could actually be worth $0.

Any insights into this would be helpful.

MustacheAndaHalf

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Re: Exercising Private Equity Options
« Reply #1 on: September 13, 2022, 10:48:08 AM »
You exercise options by paying the low share price you were given upon joining.  But the company values those shares at a higher value. I believe you owe taxes on the difference.  (It might even be short-term capital gains, regardless of how long you held the options, but let a professional confirm/deny that)  EDIT: Actually AMT

You might want to beg your company for an estimate of the shares value now, before you leave the company.  It's probably very difficult to get once you've left, and you will need it for your taxes next year.
« Last Edit: September 14, 2022, 05:58:01 AM by MustacheAndaHalf »

seattlecyclone

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Re: Exercising Private Equity Options
« Reply #2 on: September 13, 2022, 12:23:49 PM »
Are these Incentive Stock Options? If so, here's how it works in a nutshell:

Now:
* You pay your strike price to the company for the shares.
* No income is realized under the regular income tax formula.
* The difference between the current valuation and your strike price is considered income under the AMT formula. These option exercises often cause pretty large tax liability in the year of exercise due to the AMT piece.

When you sell (if the sale is more than a year after you buy the shares, and more than two years after the option was granted):
* The difference between the sale price and your strike price is a long-term capital gain (or loss) under the regular tax formula.
* Under the AMT formula the difference between the sale price and the value on exercise date is a long-term capital gain (or loss).
* If you don't owe AMT in that future year, you can claim a tax credit against the AMT you paid this year, up to the difference between what the regular tax formula says you owe and what the AMT formula says you owe.

As an example, let's say you have 10,000 shares with a strike price of $1, current valuation of $5, and eventual sale price of $10.

This year you pay the company $10,000. You need to report $40,000 of income for AMT purposes only. The amount of tax this will cause you to pay really depends on your individual circumstances outside of this stock transaction, but let's suppose it's $10,000.

Suppose the company is sold in late 2023, more than 12 months from when you bought the shares. You'll claim a $90,000 long-term gain under the regular tax formula, but only a $50,000 gain under the AMT formula because you were already taxed on that other $40,000 under the AMT in 2022. You will likely not owe any AMT in 2023 just because your AMT income is so much lower than your regular-formula income.

Now you need to take a look at the difference between your tax under the regular formula and your tax under the AMT formula (the "tentative minimum tax" on Line 9 of your Form 6251). If this difference is more than the $10,000 AMT you paid last year, you likely get to claim the whole $10,000 as a tax credit on Form 8801. If the difference is less than $10,000, you likely get to claim the full difference, leaving the remainder to carry over for a possible tax credit in 2024 or subsequent years. This can potentially drag on for a long time. I exercised some ISOs in 2013-14 and finally got the last of my AMT refunded a year or two ago.

If the sale is less than 12 months from when you buy the shares (or less than two years from when you were granted the option), different rules apply that I'm less familiar with because I was never personally subject to them.

See IRS Publication 525 for more info about all this.

mizzourah2006

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Re: Exercising Private Equity Options
« Reply #3 on: September 14, 2022, 07:50:17 AM »
Thank you both. Seattle the depth you provided allowed me to review my grant paperwork and see that I do not have ISOs, I have NSOs, but it appears that they work similarly only it doesn't look like I can ever qualify for LTCGs. It appears it will always be taxed as ordinary income. But it's good to know that I will be taxed off of my own company's private valuation of each share. My understanding is they have had a few investment banks to external valuations as they prepare to go to market, so hopefully it's somewhat accurate given the current landscape.

So from what I can tell I'm going to have to pay about ~$60k to exercise these options once you factor in taxes. I guess the good thing is that the tax bill isn't due for ~6 months, lol.

MustacheAndaHalf

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Re: Exercising Private Equity Options
« Reply #4 on: September 14, 2022, 11:57:16 AM »
@seattlecyclone - I wonder if you can shed light on my experience with pre-IPO stock options from many years ago (I'd like to be vague to avoid identifying where I've worked).

I joined a certain company and was granted stock options at a very low price/share.  The stock options vested over 4 years, with the first 1/4th cliff vesting after 12 months.

My company allowed employees to pay to exercise stock options before those options vested.  So although I didn't own any of my stock options, I could pay to exercise them.  At the time, a friend had done the same for the tax benefit.  I believe my pre-exercise incurred short-term capital gains.

When I went to HR with a check, they said my check was too small.  They said the value of the company's shares had increased, so I needed a larger check.  A day or two later I brought a larger check and they accepted it (and my form).  A larger stock value meant more short-term capital gains to pay.

Does my experience make sense, based on what you know of IRS rules from many years ago?

seattlecyclone

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Re: Exercising Private Equity Options
« Reply #5 on: September 14, 2022, 12:17:01 PM »
I joined a certain company and was granted stock options at a very low price/share.  The stock options vested over 4 years, with the first 1/4th cliff vesting after 12 months.

Yeah a four-year grant with a one-year cliff is pretty standard in the startup world.

Quote
My company allowed employees to pay to exercise stock options before those options vested.  So although I didn't own any of my stock options, I could pay to exercise them.  At the time, a friend had done the same for the tax benefit.  I believe my pre-exercise incurred short-term capital gains.

I've never worked at a place with an early exercise option. Tax-wise it doesn't make any sense to me that you would have owed short-term capital gains if you had merely purchased shares and not sold them. Looks like ordinary income is a possibility with NQSOs though. Perhaps if they withheld some shares to cover the tax withholding that would have resulted in capital gains from those shares being deemed sold, not sure.

Quote
When I went to HR with a check, they said my check was too small.  They said the value of the company's shares had increased, so I needed a larger check.  A day or two later I brought a larger check and they accepted it (and my form).  A larger stock value meant more short-term capital gains to pay.

The stock options I've personally heard of all have fixed strike prices. Could an agreement potentially be written to make early exercise available at a variable price that depends on the company's current valuation? Maybe, I don't know of any reason why not. A higher valuation could cause your tax liability to be higher, so if they felt they had an obligation to withhold for that they could demand a higher check amount for that reason.

MustacheAndaHalf

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Re: Exercising Private Equity Options
« Reply #6 on: September 14, 2022, 04:27:16 PM »
I joined a certain company and was granted stock options at a very low price/share.  The stock options vested over 4 years, with the first 1/4th cliff vesting after 12 months.

Yeah a four-year grant with a one-year cliff is pretty standard in the startup world.

Quote
My company allowed employees to pay to exercise stock options before those options vested.  So although I didn't own any of my stock options, I could pay to exercise them.  At the time, a friend had done the same for the tax benefit.  I believe my pre-exercise incurred short-term capital gains.

I've never worked at a place with an early exercise option. Tax-wise it doesn't make any sense to me that you would have owed short-term capital gains if you had merely purchased shares and not sold them. Looks like ordinary income is a possibility with NQSOs though. Perhaps if they withheld some shares to cover the tax withholding that would have resulted in capital gains from those shares being deemed sold, not sure.

Quote
When I went to HR with a check, they said my check was too small.  They said the value of the company's shares had increased, so I needed a larger check.  A day or two later I brought a larger check and they accepted it (and my form).  A larger stock value meant more short-term capital gains to pay.

The stock options I've personally heard of all have fixed strike prices. Could an agreement potentially be written to make early exercise available at a variable price that depends on the company's current valuation? Maybe, I don't know of any reason why not. A higher valuation could cause your tax liability to be higher, so if they felt they had an obligation to withhold for that they could demand a higher check amount for that reason.
I think that might be it, they could have been Non-Qualified Stock Options.  For some reason I only recall them being "non-ISO".  These stock options had a fixed strike price and fixed number of shares.  They had an expiration date 10 years in the future.

Poking around, I guess it was some combination of exercising NQSOs, and the 83(b) election mentioned below.

"Exercising nonqualified stock options is a taxable event. At exercise, the compensation element, or difference between the FMV at exercise and the strike price is taxable as ordinary income and subject to payroll tax."
https://darrowwealthmanagement.com/blog/early-exercise-stock-options/

"When making an 83(b) election, you request that the IRS recognize income and levy income taxes on the acquisition of company shares when granted, rather than later upon vesting."
https://www.nerdwallet.com/article/investing/83b-election

mizzourah2006

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Re: Exercising Private Equity Options
« Reply #7 on: April 24, 2023, 02:22:40 PM »
UPDATE

You all were so helpful with this I thought I'd bring it back up and see if you have any insights into the update to this situation.

So I ended up exercising them and they added the difference between my option price and their estimate of the strike price to my earned income for 2022 in box V of the W-2.

I just received word that they have agreed to sell the company and the share price sale will only be about 70% of what they said was the fair market value only 5 months ago, which is insanely frustrating and what I was afraid of. So it looks like I will have ended up paying taxes on about $38k in earned income/short term capital gains I'll never receive.

So my question is, is my only option to carry it forward as a loss for the next 13 years and right off $3k in earned income each year?

Again, it seemed you all were very knowledgeable about this and I figured it was worth a shot asking for thoughts and insights.

seattlecyclone

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Re: Exercising Private Equity Options
« Reply #8 on: April 24, 2023, 02:54:53 PM »
So my question is, is my only option to carry it forward as a loss for the next 13 years and right off $3k in earned income each year?

Sounds like you have a capital loss, yes. How long you carry it forward depends on if you realize some other gains in the meantime. Capital losses cancel out capital gains. Might be a good time to get out of some other taxable investment you'd prefer not to be in anymore.

mizzourah2006

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Re: Exercising Private Equity Options
« Reply #9 on: April 24, 2023, 02:59:18 PM »
So my question is, is my only option to carry it forward as a loss for the next 13 years and right off $3k in earned income each year?

Sounds like you have a capital loss, yes. How long you carry it forward depends on if you realize some other gains in the meantime. Capital losses cancel out capital gains. Might be a good time to get out of some other taxable investment you'd prefer not to be in anymore.

But it would make the most sense for it to be short term to short term, right? I don't have a ton of short term gains right now. I had some losses last year, so I sold out to match.

seattlecyclone

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Re: Exercising Private Equity Options
« Reply #10 on: April 24, 2023, 04:19:37 PM »
So my question is, is my only option to carry it forward as a loss for the next 13 years and right off $3k in earned income each year?

Sounds like you have a capital loss, yes. How long you carry it forward depends on if you realize some other gains in the meantime. Capital losses cancel out capital gains. Might be a good time to get out of some other taxable investment you'd prefer not to be in anymore.

But it would make the most sense for it to be short term to short term, right? I don't have a ton of short term gains right now. I had some losses last year, so I sold out to match.

Yes and no. You'll benefit more from canceling out a short-term gain this year vs. a long-term gain this year, but if your comparison is long-term gain this year vs. regular income in a decade, the analysis might look different. That amount you carry forward doesn't get adjusted upward for inflation every year.

mizzourah2006

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Re: Exercising Private Equity Options
« Reply #11 on: April 25, 2023, 07:53:53 AM »
So my question is, is my only option to carry it forward as a loss for the next 13 years and right off $3k in earned income each year?

Sounds like you have a capital loss, yes. How long you carry it forward depends on if you realize some other gains in the meantime. Capital losses cancel out capital gains. Might be a good time to get out of some other taxable investment you'd prefer not to be in anymore.

But it would make the most sense for it to be short term to short term, right? I don't have a ton of short term gains right now. I had some losses last year, so I sold out to match.

Yes and no. You'll benefit more from canceling out a short-term gain this year vs. a long-term gain this year, but if your comparison is long-term gain this year vs. regular income in a decade, the analysis might look different. That amount you carry forward doesn't get adjusted upward for inflation every year.

Good point.

 

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