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Let's say I have some stock options in my company that I can exercise for $x. And the company's value has been assessed by some external entity to revalue the stock to $x+y. The company is still private, but these have (supposedly) intrinsic value, right? So should there be a market for such a thing (e.g. is there?). Or if I purchase, will they just remain in my broker / Carta / whatever entity holds the options?

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It depends on the company charter. Some companies allow employees trading their shares in what is called "over the counter" (OTC) market. Not all companies allow that, some companies do not allow shares transfer without their prior approval. You'll need to check with your company what their policy is.

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Yes, though the actual mechanics depend on your company. Very few private companies allow OTC sales. They may occasionally have a tender offer, during a capital raise, to give employees the opportunity for some liquidity by having their institutional shareholders purchase directly from employees, or by doing a stock buyback.

For early-stage employees who wanted to get liquidity from my previous job’s shares, there were a lot of salespeople trawling LinkedIn trying to offer that service for you. The way it works is they give you a loan, with the shares as collateral, and a contract that you will transfer the shares to them as soon as there is the ability to do so. You will not get as much money as in a private sale or a tender offer! But that discount is the price you pay for this bespoke lending process. Be very sure you understand the contract.

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