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by pfarrell
1491 days ago
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Short answer: greed. They didn’t want to give up any shares. To pay for the tax they owed between strike price and current market value, they should done a cashless transfer and sold off a portion to cover the taxes and then held the remaining for a year to get capital gains tax treatment. I think ultimately they didn’t think the party would end. I had some coworkers there who had sold stock when they could and were thought of as leaving money on the table because the stock can only go up. Those ended up being the smart ones. But hindsight is 20/20 |
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Greed by the taxman.
It would be a non-issue if the tax authorities collected the tax at the point those shares are converted to something else, or used as collateral to a loan. But to tax them without any ability for the employee to extract value from them - especially relevant for privately listed companies with glacially illiquid stock - is abhorrent.
But instead the taxman has to always be the first to eat the pie. Even if that pie never turned into anything real.
In the UK it is horrid- share options of any meaningful value are taxed at ~%63 (including all hidden National Insurance taxes) and it could be years before you can cash your shares, if at all.