You can learn from this and never be played like a sucker again, but many people it takes 2 or 3 goes around to realize. But it's fine for the CEO, there'll be another 22-year-old around to take this deal in a year.
There are many examples where I don't think there's a strong connection between the level of professional experience with the familiarity with the startup environment/lingo/negotiation.
You already had 2 broken promises and you are still wondering if you should give the other person the benefit of doubt..
What's that they say about, "fool me once, shame on you.. fool me twice, shame on me"... not sure if they have something for "fool me thrice.. "
And how does your stake compare to theirs?
And are some of those larger shareholders also paid from the company on a monthly basis or do they work for free?
10K in the hands of an employee is a hell of a lot more valuable to them than another 10k is valuable to a millionaire/billionaire
* As opposed to no money, aka the types of companies where the real profit is in the difference between what they pay their employees and the market rate.
As an employee, for some of these equity packages you'd almost need an MBA to decipher if they're any good with all the things that can happen, so I usually don't even bother and just go to places that pay fairly or have interesting work.
Maybe a simple way to think about it: if your market salary is 100k, and they offer you 60k/yr and 2% of the company, is that 2% of the company worth 40k? (And how far can they dilute it?) To me that generally sounds like a bad deal, but your milage might vary depending on the circumstances.
Don't be a sucker, man