[singron]

This is has actually been used before.

Ports would tax ships on the value of their cargo. It wasn't viable for the port to create valuations themselves, so they left it up to the ship, but the port had the right to buy the cargo at that price.

The scheme kind of works well if it's liquid commodities (e.g. grain, oil, lumber) and the purchasing right is held by a non-capricious authority (i.e. one that only exercises that right to call a bluff).

Taking a down-round on an IPO can be very damaging to a company. Since employee equity is based on options, that puts those options underwater and means employees will make nothing in the IPO. Internally, the company is doing 409a valuations and admits in writing that the valuation is down.

[Gigachad]

I wonder how this works for items that have far more value to the owner than the market value. Say shipping my personal belongings to another country. The value of my stuff is probably quite low, but it would be incredibly inconvenient and disruptive if it was purchased at it's market value and flipped on ebay.

[lokar]

Do many companies pay in options anymore? I’ve only seen RSU for years now.

[singron]

Basically all early stage startups use ISOs. Public companies typically use RSUs. Some startups transition to RSUs before their IPO.

RSUs are kind of unworkable if the valuation will increase significantly before the shares become liquid since you owe taxes on their value as they vest whereas ISOs let you defer taxes until at least exercise if not sale.