I wouldn't be interested in selling my exercised options, but my unexercised ones that could work, but you would need to offer at least the purchase price. Unfortunately, only employees can own shares... :[
I simply don't believe you - if there were a hypothetical way you could have a $50 bill on your desk but, in case they end up worth something, your unexercised options are no longer yours, they're someone else's, and you didn't need to deal with anything else and it were easy legally - then I don't think you would actually want to do that, you wouldn't choose to make that trade.
Let me compare it with something else - say you already belonged to a gym but your employer as a christmas gift gave you a totally transferrable 50% off gift certificate (but that there's no particularly liquid market for, it's not like it has an obvious market price you can sell online) to a more expensive gym that is far from you, that you don't like for some reason because its focus doesn't match yours (maybe it's always fairly bustling and you like fewer people distracting you, whatever, in fact maybe you like going at times that that gym is closed!), and that is still more expensive after 50% off than your annually paid-up membership 15 minutes from your house and that you like: then you would be happy to give it to someone you know for, say $10 or if it'll make them happy or as a favor or for a sandwich. It really is something you value at closer to $0, and I judge that you would be glad to part with it for that amount or for free in that case.
I judge you wouldn't actually part with your options for $10 or $50 even if hypothetically it's legal and trivially easy for you. This is just my impression. I don't think you would do it. If you reflect on the two scenarios above (the first and the second paragraph of this comment) I think in your heart of hearts you see the difference. It's not a small difference.