Boom. First of all, congrats on that success.
Second, I love hearing stories like this. I'm sure I'm biased because I'm in my late 30s but it's a nice break from all the tech wunderkind profiles in the media and the ageism of VCs & startups.
Turns out, almost all the uber successful tech entrepreneurs were over 30 when they hit their stride. The wunderkind thing is almost entirely a myth.
As for me? I'm out of luck.
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.
I sold IndexTank to LinkedIn among other things.
It was a gradual process for me that started with the first dot-com boom. It wasn't as big of a deal as I thought it would be.
I was 41.
Cashing out stock from public companies I've been at, selling consulting services before building IndexTank, selling IndexTank.
I don't think there is such a thing as overall happiness. I do live in the present more than I used to, but that's perhaps because I'm older. I do worry less about certain things, but the "worry hole" is always there asking to be filled. We all age, get sick, have family / relationship problems, need to stay motivated. I almost certainly enjoy life more than I would if I were forced to take an unpleasant job, but there are many other things a person can do to make life enjoyable besides trying to win the startup lottery.