Don't do options, just give the employees the stock and you eat the tax bill. If that tax bill becomes too large to be worth it, then it's time to give your em

Don't do options, just give the employees the stock and you eat the tax bill. If that tax bill becomes too large to be worth it, then it's time to give your employees RSUs. But you say, how about vesting and such? It's a waste to pay those taxes if the guy leaves after 2 years. You just paid 2 years of taxes for no reason! That means in practice you'll be giving RSUs around the series A or B funding point. Another option is you give the employees a non-recourse loan to 83b purchase their options on hiring. The loan is due on a liquidity event when it's higher than the price of the options. This makes it a tax optimal and zero-cost way to give stock to your employees. I don't know if that is legal although. Another option is to make your options just expire after 100 years.