For the great unicorns, not that early. If you join as a senior engineer it’s relatively easy to get 250-400k in equity per year, so you just need to wait for the company to do 10X in order to make $3-5M a year. The math is different from the stock options you mention, we are talking about joining very late in the game, once the companies are already in the unicorn status. By that stage they don’t even give options anymore, just illiquid RSUs. The people who joined really early of course won the lottery and you have rank and file employees sitting on high 8 figures.

There are some interesting numbers here: https://iporegrets.com/

I know several people from AirBnB, Doordash, Snowflake who all joined around 2018 and made bank.

I was an early employee at a smaller startup that is still illiquid and my stock options (fully exercised) are worth $6M. They could still all go to $0.

Just by looking at myself and my immediate network, I wouldn’t say playing the startup game is necessarily like a lottery, the odds are better (but note that I still chose FAANG lately, as mentioned above). YMMV.