Consider the time frame in which these anecdotes took place. My understanding is that most people "in the know" believe the environment has changed such that you'll never get a early Facebook employee type payout anymore. Founders, VCs and their lawyers have developed a plethora of tricks that disguise the way you're getting screwed or ensure that, through some future trickery, you will. You're best bet is to command a high salary worthy of your skills, choose a company that has a culture you'll enjoy and assume that your options are worthless.
Sometimes you get lucky and get a mid 6-fig payout (me and a friend did in a medium-sized acquisition), but most of the money I and most of my friends make is from RSUs, high salary, and year-end bonuses that are actually somewhat tied to company performance.
Playing the lottery is all well and good, but a stable high-paying job will yield a higher EV.
Honestly, in this field, even a $1m payout isn't hugely life changing. By your late 20s you should be making at least 150k/yr + bonuses/etc, and with proper investment you'll be fine for retirement.
