Bingo. And how generous is a "generous equity package"? Is this the founder / management team's first rodeo? Because things could _look_ rosy but still be cr

Bingo. And how generous is a "generous equity package"? Is this the founder / management team's first rodeo? Because things could _look_ rosy but still be crappy compared to that "safe job". What if you join this hot new startup and things look great only to have them screw you in some manner? It happens. "The only job security is the security you create for yourself." Sure. For some that might be to work for a startup. For some it might be to found a startup. For some it might be to work for a "safe" company doing something innovative (it happens). Risk ultimately is weighing the probability of some amount of loss versus some amount of gain. It is subjective and historically informed. The OP stated "Think about it: when is the hardest in your life that you’ve worked? For me, it was when everything was on the line. Not just my job, but my income, my children’s schooling, and our groceries. I wasn’t working hard to impress my boss, get a promotion, or avoid a negative performance review. I was working hard to make ends meet." That's fine for him. I would rather not be in a position where my children's education is on the line. Does that mean I don't potentially hit the high gains the OP has? Maybe. Or perhaps others are making more informed decisions or slightly different risk-based decisions (maybe that key hire ended up going to a company who already has their series A or B, has better revenue / pipeline, and is going for a slightly lower equity package..that's still risky it's just not as risky what OP seems to be suggesting)