I started at Apple in 1994. I left to found a startup in 1997. It was an delightful and educational disaster; I learned that I loved startups but didn't have the constitution to lead them.
My tenures at these startups were anywhere from 18 months (acquired for modest payout) to 8 years (IPO for modest payout).
I keep doing it because of the reasons listed in the article. Flexibility, ability to have significant influence, get to work on cutting-edge stuff, have to furiously learn new stuff. Plus I enjoy the recruiting and team building -- I am an extrovert. :)
Yes, I have one kid. I tutor math at her elementary school. (See 'flexibility', above.)
Apple IPO'ed in 1980, at a $1.8 billion ($5.2 billion inflation-adjusted) valuation. 1994 was fourteen years after that, when the organization was in decline.
I know. There was a (now deleted) comment between yours and mine that said "wow, you were an early Apple employee, what was it like?" I figured that poster didn't realize how old Apple is.
I've done about half that many. Start-ups can be nice in many ways. I'd still love everyone considering a start-up to read the linked essay, because a flood of over-optimistic employees can drive down wages and working conditions. Demand good wages, demand good working conditions, don't let "we are a start-up" be an excuse for someone getting you to eat a shit sandwich.