You forget that their "singular vision and balls" would be useless if no engineers every actually implemented it. The point of stock allocation is to get people to do the work that needs to be done, and it's risky because at the time of hire the engineer doesn't know if the idea will be successful. Generous stock allocation, in my mind, is a token of good-will to the engineer and a recognition of the importance of the engineering phase of the project.
The problem is that as an engineer, he's depending upon his track record of past products to make sure he can get his next job. If the company fails, he suddenly has 2-5 years on his resume at a company that nobody's ever heard of, with a product that nobody uses, and the only thing people know about it is that it failed. Not exactly the best recommendation.
And even if your bosses give you a great recommendation, it can sometimes still hurt your career. After all, the company failed. Maybe these bozos recommending you were idiots too, and the fact that you were working for them means that you were also an idiot.
This attitude is thankfully pretty rare in Silicon Valley, but it can be quite common in other parts of the world. Early employees actually run more resume risk than founders do, because if the company fails, the founders can at least put "Founder & CEO" on their resume, but the engineers can only put "Software Engineer, company you've never heard of."
it can sometimes still hurt your career. After all, the company failed.
So? Every for-profit company I worked for from early 2001 through 2008 failed. Who blames the programmers for the failure of a company? In my experience, virtually no one.
Company you've never heard of - doesn't that apply for most companies? I still don't think that risk is comparable to losing the family fortune.
Anyway, it is all in the upfront negotiation. If engineer is unhappy with the conditions (ie not enough stock options), he should leave. To complain afterwards is lame (oh, they made a shitload of money - if only I had negotiated for more stock options...).
All I can say is that he knew it was a bad deal and he nonetheless took it.
One aspect was that he was having trouble finding interesting projects to work on. The JDAM precursor where he teamed with a major aerospace firm was I think lost due to politics. Simple GPS systems were a step or three down from that but were nonetheless more interesting than the other work he had been able to find for some years previous to that (losing the JDAM precursor contract was a last straw sort of thing).
