Why quit? Most people will mess up #2 or execute badly on #3 or even then #4 is unlikely to happen when FAANGs can just copy you and put you out of business instead of buying you out and rewarding this behavior.
#5 will almost certainly happen even if you keep doing #1, earning a huge salary.
The numbers and risks just don’t make sense anymore.
...because there's a glut of investor money chasing "AI", raising money for your new AI startup is not particularly hard if you are linked with any of the big names in AI.
Even if the startup "fail", the founder could have been paying themselves a market-rate salary with the added possibility of an FU-money exit. The downsides are limited.
I think you underestimate the probability of little to no return, and ignore opportunity cost.
I've seen several startup founders pay themselves below market for years because they have all that equity. Only to find out, a couple down rounds later, it wasn't worth it. They tried though.
#5 will almost certainly happen even if you keep doing #1, earning a huge salary.
The numbers and risks just don’t make sense anymore.