Getting a chunk of stock options with huge upside seems palatable vs guaranteed shares at a large tech company. Offering me a 15% discount seems insignificant.

Getting a chunk of stock options with huge upside seems palatable vs guaranteed shares at a large tech company. Offering me a 15% discount seems insignificant. The moment you go public, everyone is going to buy all the shares available. How do you decide how many each person can buy? If I buy before an exit event, I am taking on even more risk than the option because now I am paying all of the taxes. This offers no benefits, but increased tax risk and I'm paying more to buy shares in the first place.