Or put differently, assuming these were somehow mutually exclusive (they're not), and assuming similar pay, benefits, perks, location, etc, would you rather have stable employment, or interesting employment?
When I go home at night and my girlfriend is sat there, the last thing I want to say is "hunny, I'll have to find another job. Super awesome startup-v4 is out of cash, I'll probably have a new job in a month but we'll have to tighten our belts until then."
The question I have to ask myself is this: What's best for my future family? That I 100%, undoubtedly love my job, or that I 100% always put food on the table?
For me it's the latter. For most billionaires, it's probably the former.
And that's the crux of it, isn't it? I find that if my job is boring and my life outside of work is slow and uninteresting, I'm very unhappy. I need one or the other to be engaging on a regular basis. My wife is the strange sort of creature that is happiest in a very stable routine at work - one that I'd typically call monotonous.
Fortunately we already live happily on less than a third of our combined income, so it's actually lower risk for us happiness-wise if I pursue higher financial risk but more interesting employment. My lack of routine can often upset her, but it's much preferred to me being totally drained and demoralized at the end of a long and painfully boring workday.
This is enough to live by and enough to keep myself entertained but it isn't enough to be able to save, it's not a viable income level to be able to risk my home and my safety on a job I could lose in two months time.
... I should move to silicone valley. Things seem much easier out there.
The repeated references in this thread to "silicone valley" and the context which suggest that that reference might not really be what is intended lead me to point out that "Silicon Valley" is a region in northern California so-called for the predominance of computing-related tech firms (from the role of silicon in computer chips) and "Silicone Valley" is (as well as a not-infrequent misspelling of "Silicon Valley") a common joking name for southern California's San Fernando Valley that is a play on northern California's "Silicon Valley" and on the SFV's concentration of firms in the adult entertainment industry.
I go back and forth on this myself. The biggest thing keeping me from doing so is the cost of living. In South Carolina I rent a 1200 ft^2 (~110 m^2) 3 bedroom house on a third of an acre for less than $1,000 per month. I live about 10 minutes from the beach (Atlantic), and 15 minutes from work. My wife's a marine biologist and a yoga instructor. She'd be able to teach classes there, but it will take a while (if it's even possible) for her to get well-enough acquainted with the orgs in the area to continue her career as a biologist. That means to keep the same disposable income I'd need to cover both our salaries, plus the increased cost of living, and all the risk of our livelihood would be on me. The last time I ran the numbers I figured out that in order for us to have the same disposable income I'd need to make over $200k/yr or trade salary requirement for long commute times.
I'm on the other end of the scale - if I did move to Silicone Valley, my income would at least triple within the first couple of years... Assuming success and a visa.