Uber is pre-IPO and is currently issuing RSUs? Facebook also issued RSUs before IPO as far as I know. Right, that approach might not be possible for early startups. The Pinterest & Quora approaches here are pretty great and the companies have put in the time to have useful, rigorous discussion to validate the approach. Quite the opposite of what Uber seems to have done here with the ISO conversion & improper communication.
Another option for early startups is to support 83(b) and to, well, bonus the employee the strike so they can exercise immediately. I've seen a case where a key employee demanded they get a big bonus to cover a large strike in a new, large grant. (And he got it, and was butthurt over the bonus unexpectedly putting him in a higher tax bracket...). Facebook has handed out $100k signing bonuses to new grads... On one hand this all makes employee comp more expensive, on another hand there's the absurdity of CEOs and investors making several orders of magnitude more than the most influential employees.
Another option for early startups is to support 83(b) and to, well, bonus the employee the strike so they can exercise immediately. I've seen a case where a key employee demanded they get a big bonus to cover a large strike in a new, large grant. (And he got it, and was butthurt over the bonus unexpectedly putting him in a higher tax bracket...). Facebook has handed out $100k signing bonuses to new grads... On one hand this all makes employee comp more expensive, on another hand there's the absurdity of CEOs and investors making several orders of magnitude more than the most influential employees.