Suppose I was granted 100,000 shares of ISO stock in a startup in the US with a strike price of $1/share and current valuate of $1.25/share. These shares are 100% vested when I leave the company and I now have 90 days to exercise.
If I were to initiate an exercise-and-hold (cash to buy stock) it would cost me $100,000. I don't have $100,000 lying around but fortunately the stock incentive plan allows for exercise-and-sell (cashless exercise for money). This would allow me to exercise and immediately sell the stock for a gain of $25,000 without putting any money down.
However I think the company will continue to do well and would like to keep my stock in the company (but I don't want to pay for it!). So I could initiate an exercise-and-sell-to-cover (cashless exercise for stock). This won't cost my anything but I'll end up with fewer shares.
If I want the most shares but don't enough money to buy all of my options, would there be any reason I couldn't initiate both an exercise-and-hold on half ($50,000) and an exercise-and-sell-to-cover on the remaining stock?
Another way to think about the question: can I perform multiple exercises during my 90 day window? (e.g. exercise 50% of the options, then the other 50%)
Note that this is just an example to illustrate my question: Would it be possible to exercise-and-hold on some shares of stock and exercise-and-sell-to-cover on the rest? I'm ignoring the tax implications for each scenario, etc.