> The opportunity cost of the down payment making you unable to early exercise some startup equity could on the other hand leave you pretty full of regret. Sta

> The opportunity cost of the down payment making you unable to early exercise some startup equity could on the other hand leave you pretty full of regret. Startup equity of the kind that produces fuck you-money returns shouldn't cost that much to early exercise since it's usually early stage, that's kind of the whole point of early exercise and filing the 83b before the imaginary value goes up in subsequent funding rounds. When it's late stage enough for exercising to cost a pile of money, people usually don't bother with exercising and simply wait for a liquidity event to occur, assuming accelerated vesting will accompany it, and pay the exercise cost and taxes directly from the shares AIUI. But I suppose it's nice to be able to exercise and leave if you wanted to before a liquidity event, since the options tend to expire in what... 90 days? Preserving that option with a pile of cash on hand is useful, handcuffs are annoying regardless of their color.