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.
2500$ is 1M now
That 25k would be 10M now per year, or $40M in your example
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
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.