I've seen a lot of people lose a lot of money because they bought into the "value the equity at zero" mentality. It sure sounds great and edgy to be blasé and just take your pay, but if that was true, you'd be better off working at FAANG 99% of the time.
IMO if you work for a startup company, you should only do so because you believe in it, and if you believe in it, you should exercise your option as fast as you can, perhaps with an 83b election if you can afford it. Otherwise what's the point of taking a job at a startup with a lower TC and higher risk outlook than a FAANG job?
Hence, I think:
- only join startups you strongly believe in,
- only join startups that offer good equity package, have raised good rounds, have healthy cap tables,
- get as many options as you can,
- exercise them as fast as you can,
- work hard to make it worth something,
- leave if it doesn't work out.
That's kind of the whole point of joining a startup. You're joining a bet, where you've got a significant chance of influencing the outcome.