I'm sure you can, at a discount. You probably won't find many/any banks willing to do that, but I imagine you can find private parties who are willing to give

I'm sure you can, at a discount. You probably won't find many/any banks willing to do that, but I imagine you can find private parties who are willing to give you $0.05 on the dollar for some options. I imagine the reason that "rich people" can borrow against their options is because they aren't common share options, or they have some sort of control over the destiny of those shares. For common shares there are several ways for them to become worthless, some of which people on this thread have mentioned (dilution & preference are the two big ones). If you're holding on-paper $100k worth of stock options, you probably couldn't get $10k for them except in very rare cases. If you were an early member of Uber, you can probably find institutions that want to buy shares, so maybe you can get money from them. But remember, that on-paper $100k has tax implications along with it when you buy them/sell them, so don't forget to set aside enough money to pay that.