I feel like legal manipulation is very bad for the startup ecosystem. Even here, at the YC forums, people assume their startup equity is worth $0 and advise you to go with a FAANG (or day that they broke even with friends at faangs after their exits). How is a legitimate startup supposed to recruit the best people under these conditions?
1. As a rule of thumb, you can't.
2. As an exception, you can if they really want to see you succeed (i.e. for your mission).
3. As an exception, you can if they're dissatisfied or bored with their FAANG career and the job represents growth or excitement that they want.
4. As an exception, you can splurge on a few key hires, in terms of salary and/or equity.
5. As an exception, you will find dark horses, people who are currently undervalued by themselves and others.
But as other posters mentioned, the reason I agree with the advice about pricing equity at $0 is because that's rationally the most likely outcome. Honesty about that fact is very much appreciated, but rationally the expected value is actually (approximately) zero.