The sad thing is I'd wager 95-99% of startup employees put in work hoping for some kind of similar payout, only to never find it.
But that's assuming they held onto all that stock for all this time, which is probably did not happen in the vast majority of cases. My guess is that most sold it for less than 10x within 10 years.
10years was 50x
2500$ is 1M now
That 25k would be 10M now per year, or $40M in your example
I think Jobs was a special and good leader in many ways, but also a total jerk.
Imagine if Jobs were to have kept notes and been more coherent in his feedback i.e. "I don't like the menus. Don't distract the team now but analyze it, and I want a plan for adjust them in X weeks. Then, push it into the schedule".
There may actually be some benefit in keeping your devs. on a 1 or 2 weeks sprint dogleash but I doubt it. Keeping them on pace but not needlessly diverting them is good.
And Hardware leaders not understanding refactoring is bad. I mean, we never really estimate it well, but still.
I think it shows us how far marketing goes with respect to how we understand a company as much as it's products.
In fact, maybe it's gotten worse. When I worked for Apple in the 1980s and 1990s I lived in Cupertino and walked to the office every day. The last time they tried recruiting me, the offer was not enough for me to do that (Cupertino has gotten more expensive to live in). Maybe if the offer had been enough to do that, I would have bitten; I liked most of my time at Apple, and I loved living in Cupertino and walking to work. Some people I like and respect are reportedly still there.
I don't think big salaries are the draw at Apple. Some of what recruits candidates is moonbeams and fairy dust, just like in the games and movie and music industries. In the cold light of reason, that stuff shouldn't justify a discount on the payscale, but in the real world it apparently does.
This is what being passionate is all about.