I think the reverse: that entering a company based on "am I going to enjoy it here?" is a better bet. If you hate it there, you'll probably leave and never ves

I think the reverse: that entering a company based on "am I going to enjoy it here?" is a better bet. If you hate it there, you'll probably leave and never vest your equity. Even if you hang on and suffer through it to get your equity, it'll damage you in ways that money won't help with. If you hate it, chances are that everyone else does too, which means the good people will leave and the startup is less likely to succeed even if everything else is good. Most engineers enjoy interesting challenges, and this can be a big factor in choosing a role. If the startup is providing interesting challenges then it's doing interesting/difficult stuff. This is a factor in success - startups that aren't doing interesting/difficult stuff are easier to copy and have less barriers to entry for competitors. Even if you don't get lucky and win the equity lottery, you had a good job and probably learned some interesting things.