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They may want to sell for $0.01, but they may not be able to and you won't be able to buy. See also: articles of incorporation, minutes & bylaws, shareholder agreements.

Of course. But in many cases they will. And even in cases where there are restrictions....there are often things that can be done. But that's not really the point.

My point is calling something illiquid worth "nil" is often silly. Maybe don't consider it worth its face value. Certainly don't go spending money you don't have yet. But automatically writing everything down to zero is dumb.

> not yet liquid stock that they would like to sell me

That's... isn't that impossible by definition?

When it comes to company stock liquidity isn't really binary. There are degrees.

You can't transfer the stock, but you can sell a contract promising to sell at a specific price once it's liquid.

Except if the company has a right of first refusal.

And in some cases, eg financial services companies, this can be a major violation.

Isn't that essentially shorting the stock?

It’s a put option.

If I sell it for $0.01 can I write off the difference?