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Re:Ask HN: Anyone have stock option horror stories? by snypher on Wednesday March 16, 2022 @11:00PM (#30707158)
I think it is employee options, something like chunk of options convert to real shares (say $1m). Tax man asks hey, where's my eg $220k? Employee says it's ok, I have $1m (in shares). Something happens on the market and shares are now worth $0 (or sub-$220k). They still owe the $220k!
Re:Ask HN: Anyone have stock option horror stories? by systemvoltage on Wednesday March 16, 2022 @11:08PM (#30707225)
Can you not take $1M loss? At one point, you had owned $1M of stock. It went to $0. That's a personal loss of $1M.
Re:Ask HN: Anyone have stock option horror stories? by rocqua on Thursday March 17, 2022 @06:33AM (#30709569)
The 220k tax bill is on 'income' because it is employee compensation.

The 1M loss is 'capital gains' and therefore a separate category which cannot offset against the 220k income tax bill.

Re:Ask HN: Anyone have stock option horror stories? by thundergolfer on Wednesday March 16, 2022 @11:51PM (#30707473)
At least in Australia, capital losses do not entitle you to a refund on taxes owed or paid. They just just offset subsequent capital gains.
Re:Ask HN: Anyone have stock option horror stories? by trhway on Wednesday March 16, 2022 @11:27PM (#30707345)
[IANACPA] without 83b election the $1M gain on stock options on the moment of exercise goes into regular income while the $1M loss would go into capital loss. The limit on loss offset to the income is $3K/year. So in the first year there would be $997K of regular income to pay taxes from and $997K carry over loss. Without any other capital gains to use the loss against, it would take another 333 years to write that loss down.
Re:Ask HN: Anyone have stock option horror stories? by systemvoltage on Thursday March 17, 2022 @01:37AM (#30708016)
Example from [1], emphasis mine.

Suppose the stock market has a bad year. You sell a stock or mutual fund and realize a $20,000 loss with no capital gains that year. First, you'll use $3,000 of the loss to offset your ordinary income. The remaining $17,000 will carry over to the following year.

Next year, if you have $5,000 of capital gains, you can use $5,000 of your remaining $17,000 loss carryover to offset it. You can use another $3,000 to deduct against ordinary income, which would leave you with $9,000.

The remaining $9,000 will then carry forward to the next tax year. Assuming that you had no capital gains in the following three years, you could use up the remaining $9,000 loss, $3,000 at a time, over those three years.

[1] https://www.thebalance.com/can-a-capital-loss-carryover-to-t...

The $3000 stacks as an additional deduction from income. But if you had capital gains of $100k, that can totally be offset with a remaining balance of $900k. You can chew away your capital loss carryover with capital gains faster than 333 years.

Re:Ask HN: Anyone have stock option horror stories? by quickthrower2 on Wednesday March 16, 2022 @11:21PM (#30707301)
Tax years is the issue I assume