I’ve done it, you have to have executive authority over the issuing company to do it, as other directors and their legal counsel are too uninspired to do anythi

I’ve done it, you have to have executive authority over the issuing company to do it, as other directors and their legal counsel are too uninspired to do anything outside of the norm. Your IRA is a legal entity and you can grant an option to it. It needs the cash to exercise it. Options can have shares at any price in them, such as discounted to nothing but it comes down to which consequences you care about. Making a potentially screwy 409a valuation isn't a big deal, but also avoided if done before other investors come in. Either way it can be a tolerable level of consequence.