2 ms·

> How is this a loss? They paid taxes on gains? Not sure what the badness is here. They cashed out and paid taxes. They didn't take real gains, they took illiq

> How is this a loss? They paid taxes on gains? Not sure what the badness is here. They cashed out and paid taxes. They didn't take real gains, they took illiquid paper gains and paid AMT (Alternative Minimum Tax). Example: Strike price was $1 / share, "on-paper" price was $20 / share. Employee had 20,000 shares, with a "paper" gain of $380,000. They had to pay the taxes on those gains even though the stocks were not publicly traded and therefore illiquid.

lmm 9y ago
So they were taxed on a best-effort valuation of the thing they received from their employer? That seems like how tax is supposed to work. (How else would you do it - in-kind taxes?) Illiquid investments are a risk, if you lose money on them then you lose money on them, and you don't get back the taxes you paid, just as you don't get back the taxes on income you lost at the card tables.
- seattle_spring 9y ago
  Then you must support paying unrealized gains on your home and stocks each year, even if you don't sell them? Because it's literally the same thing. > How else would you do it The same way every other investment works: Tax the gains when the asset is sold.
  - lmm 9y ago
    > Then you must support paying unrealized gains on your home and stocks each year, even if you don't sell them? Yes, I do. I think the whole notion that you pick and choose when to realise gains invites abuse.
    - seattle_spring 9y ago
      This would bankrupt so many homeowners.
      - lmm 9y ago
        Then prices would fall to the point where people could afford their homes, or governments would run massive surpluses and could lower their tax rates to remove the burden, or some combination of the two effects. It would remove the disincentive to trade homes which is bad for everyone: if I live next to your job and you live next to my job we'd both be better off if we bought and sold each other's houses, but at the moment we're discouraged from doing that because our tax bills would come due.

lmm 9y ago

So they were taxed on a best-effort valuation of the thing they received from their employer? That seems like how tax is supposed to work. (How else would you do it - in-kind taxes?) Illiquid investments are a risk, if you lose money on them then you lose money on them, and you don't get back the taxes you paid, just as you don't get back the taxes on income you lost at the card tables.

seattle_spring 9y ago
Then you must support paying unrealized gains on your home and stocks each year, even if you don't sell them? Because it's literally the same thing. > How else would you do it The same way every other investment works: Tax the gains when the asset is sold.
- lmm 9y ago
  > Then you must support paying unrealized gains on your home and stocks each year, even if you don't sell them? Yes, I do. I think the whole notion that you pick and choose when to realise gains invites abuse.
  - seattle_spring 9y ago
    This would bankrupt so many homeowners.
    - lmm 9y ago
      Then prices would fall to the point where people could afford their homes, or governments would run massive surpluses and could lower their tax rates to remove the burden, or some combination of the two effects. It would remove the disincentive to trade homes which is bad for everyone: if I live next to your job and you live next to my job we'd both be better off if we bought and sold each other's houses, but at the moment we're discouraged from doing that because our tax bills would come due.