With options, there's always a risk that they will be worth nothing, or very little.
I would rather have some options in several companies than a lot of options in one to increase the chance that some of them will be valuable. That approach does require you to buy the options, whereas staying at one company means you can delay the purchase
Strategy 1: Stay for four years and vest your entire initial grant. Strategy 2: Stay 1-2 years and vest 25%-50% of your initial grant, and repeat 3x-1x.
If all the companies you work for have similar likelihood of doing exceptionally well, you've paid 4 years and gotten either one lottery ticket worth X (strategy 1) or 2-4 lottery tickets each worth 50%-25% of X. When you don't already have "enough" money, 25% of X is still life-changing, and if you can get 2-4 shots at it instead of 1, that can be a very workable strategy.
Seriously. My brother received $1 million in Tesla stock options when they recruited him. They certainly aren’t worth that much anymore. Does he stay and hope the Musk will stop tanking the stock or jump ship?
Known from a friend, he could choose RSU’s, options or cash from Tesla. (You would get more options than RSU’s to compensate for risk). Also Tesla stock price 10xed in the year 2020, even after all the hits , it’s still like 6x from pre 2020. Your brother had to join after 2020, which is unlucky I guess.
I would rather have some options in several companies than a lot of options in one to increase the chance that some of them will be valuable. That approach does require you to buy the options, whereas staying at one company means you can delay the purchase