Could you elaborate more on the cashing out of stock from public companies point? You sold IndexTank for 1.6 million dollars. I don't really consider that "never work again rich" in this day in age. Were the sales of your stock significant?
It's the same as getting between 30 and 40 years of an experimented developer's average salary where I work, so it would mean that I can live exactly as I do now (and I can't complain), but at home without needing to work anymore. Just good money to spend with family, travelling or improving your knowledge. Seems like a good deal to me.
http://www.crunchbase.com/organization/indextank
The acquisition would be much more than that.
If your position before the liquidity event is "making low six figures per year in salary," 1.6 million dollars will at least give you an ~10 year buffer in which to make it to your next liquidity event with relatively little risk.
And that one's probably the one that lets you stay in bed for the rest of your life, if that's what you really want (but it probably isn't).
even so, $1.6million is 'never work again rich'-- at modest 10% return, with capital gains taxes, you would be making enough to pay your family's expenses.