Working for a startup is inherently risky, but it’s not gambling because in gambling you can estimate the odds, and unlike gambling the odds cannot be changed after you win. Any employment contract that does not allow equity cash out at the price from the last funding round, or allows take backs, is worse than gambling, and founders that believe contracts that don’t provide those guarantees are reasonable are likely malicious and intending on doing that in future.
I do not understand a mentality that says “as a founder I should be able to get money out of the business but the people who work for me, who are also taking significant risk and below market compensation should not be permitted to do that”