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When I read "Missed their big payday" I assume they've been screwed out of their shares via convertible shares or liquidation preferences.

They didn't get to sell the top on the post-SPAC debut. Their Bs are being converted to As, but it's not as fast as they want. They are missing their maximal payday (assuming BZFD shares don't recover) but there is nothing here about them not getting their shares and being about to sell.

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The strike price is now higher than the sale price for most employees and former employees so practically they cannot sell.

Uh, could you not harvest the capital loss against gains elsewhere?

I think their point is that they should have a loss in the first place.

If you have options with a strike of $8 and a market price of $6, you could exercise your option at $8, sell at $6, and bank a capital loss to use against gains elsewhere.

Or, wildly better, you could hold the options unexercised, and use that $2 per share for whatever you want, including paying capital gains taxes on other gains.

Burning up options on 100 shares to generate $200 in losses (and actually losing $200 of cash in the process!) to offset gains that will result in $30-60 worth of tax liability makes no sense.

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