I believe that "lottery ticket" thinking is really dangerous.

It leads to making really awful financial decisions. At many companies, people don't do enough math to realize how little their options are worth. And so slog it out for years thinking it is a good deal.

And many companies will argue that paying below market is justified because they're giving you options. If you do the math, you might find out that the lottery ticket, spread out over 4 years, diluted by liquidity preferences and successive rounds don't come close to the aggregate bonuses from a 'regular' job.

True story:

At my last startup, as I was leaving, I created a spreadsheet that took everything into account (liq. pref., multiple rounds, etc.) so you could plug in the options you had and an acquisition price and see what you'd make.

I went and showed it to some folks to make sure I'd done all of the crazy math right. It turns out that

a. No one quite knew, because

b. No one else had done it

and that

c. Everyone wanted a copy of the spreadsheet