It's comical how much of modern startup compensation is gymnastics around taxes.
My understanding is that the most basic problem is if the startup gives you stock that's viewed as income and you will need to pay tax on an illiquid asset, and ISO/NSO/RSU/409a's are resulting from various elaborate schemes to give you stock-like upside tomorrow without having to pay taxes on an illiquid today.
My understanding is that the most basic problem is if the startup gives you stock that's viewed as income and you will need to pay tax on an illiquid asset, and ISO/NSO/RSU/409a's are resulting from various elaborate schemes to give you stock-like upside tomorrow without having to pay taxes on an illiquid today.