Sure, not so surprising that the high risk path is risky. What's surprising is the low risk path is so high reward.

Also, while it might be a lower risk path than the one you took, it certainly wasn't the lowest risk path available. The people who did really well had basically all their net worth tied up in one company's stock for many years.

That level of concentration risk is extremely ill-advised no matter how promising the company might be. Sure, it works out great when GOOG goes up 200%, but it could have just as easily gone the other way. And even if you want to gamble on it, you don't actually need to work there to make a lot more money than those employees did. Just load up on OOM LEAPs and relax on a beach somewhere until $100mm or more.

A really low risk option would have been to go to work for the Federal government or one of its contractors. Or maybe an established, traditional software firm like Oracle or Bloomberg.

To emphasis the risk aspect.

I worked at Yahoo for 3 years. I joined at a very fortunate time, and left at a very fortunate time that let me basically double my options. It wasn't a fortune, but it was a nice extra chunk.

But when I left, one of the guys reporting to me was still under water on the far larger chunk of options he had been granted prior to the dot-com bubble bursting. As far as I know they wouldn't have gotten over water at any point before they expired.

At the time I joined, Yahoo seemed like it was on a solid upwards trajectory. By the time I left you might have started seeing signs but things were still going the right way for a while, and had I not been offered a very interesting job I'd likely have stayed and lost a significant proportion of the value of my options.

Bloomberg wants tools[1], not people who expect to work 40 hours a week and then go have a life. If you're willing to put in that kind of time and can get into a T14 law school[2], then doing biglaw for a few years in a contract or patent practice would open a lot of doors in a lot of places, plus make it very difficult to lose your job to offshoring.

The federal government has an annoying habit of preferring contractors for technical work, both because it's easier than directly paying people what they're worth and because it allows them to claim that the government is smaller than it actually is. Nonetheless, there are pockets of good technical jobs: CIA DS&T; NSA (RF, signals analysis, cryptanalysis); DHS (CISA). You won't be laid off, and there's lots of interesting and useful work; but even if you don't want to go contractor you're likely to run away from the HR departments that seem to view their job as preventing everyone else from doing theirs or the lack of external training opportunities, and at least in the intelligence community agencies are as headquarters-centric as Google and Facebook were ten years ago.

The risk of contracting can vary wildly. Some contracts have a new prime every five years; some go fifty years or more without a changeover. There are definitely contractors and contracts that are low risk, but in general the same rules apply as in SV: stability is being able to find another job, not a guarantee of continuing the same one.

[1]: In the MIT sense.

[2]: Spoiler: if you have a high enough GPA to convince Bloomberg that you'd be a good tool, you can get into a T14 law school.

> Bloomberg wants tools, not people who expect to work 40 hours a week and then go have a life.

I worked there for almost 5 years and that was not my experience at all.