But at the time the employee is negotiating this has already been decided. The company has some valuation and you are offering some known percentage of that scarce resource. You could argue that the valuation itself is the thing being manipulated (which is partially true), but that doesn't change the cost of the offer to the company in units of equity %
If you think about the amount of money given up as a startup employee you will definitely get some winnings.
For example, say as a startup employee you are earning/being compensated 80,000 a year in equity. If you bought $80,000 of lottery ticket’s each year how much would you win. Depends on the lottery but most lottery’s have a rough payout of approximately 50-70%. Let’s say it’s 50%. So you would expect to receive back $40,000 per year.
Do half of all startups equity turn into cash, I think not. So probably more likely to make money from the lottery.
The purpose is to trade EV for a small probability of high payout. It's less extreme than the big ticket lotteries but more extreme than a scratcher. If that's not for you, don't do it
Also your last point is either obviously not true (if you're talking about big lottery winnings) or trivially true (if you're talking about $1000 scratcher prizes). More people made life changing money from a single company (Facebook) than all California lottery winners combined across all time
But most startup people don’t work at most startups.
Also…the lottery and startups work very differently.
"You can't write me a check?" I said, "No, I -- a check? Hell yeah, I can write you a check! I thought you needed money. Tell you what, I'm just gonna pay the whole thing off right now! I'm gonna be a congressman when I grow up."