Well, It's really not even at all comparable, but I have a remotely similar personal story.
When i was in grad school (studying computer science), and about to graduate, a couple of my peers started a company in Santa Barbara, called Warp 9. It was an internet ISP, at the time just a pool of around 50 dial-in modem lines with a T1 line to the rest of the internet (this was the late 90s)
I was one of the three founders, but I never wanted personally to put any money in and I was pretty dead-set on getting a job. I just didn't really think it would go anywhere and they'd just bankrupt themselves.
I went on and got a job, and the two of them did pretty well for themselves. Eventually, the company went public, called Roaming Messenger.
It was worth 100s of millions in its peak - hardly apple-levels, but still respectable.
Ultimately, though, it tanked and became a penny stock, now trading as WNYN.OB.
The company is still around -- the company was renamed back to warp 9 (our original name) and actually recovering somewhat last I looked, but anyway, I never felt quite as bad as the other founder of apple - but for a while there, I as kicking myself!
Ultimately the other two founders left too.
One of them was indicted by the SEC, and outed... I never really go the full story on guilt or innocence and we aren't in touch anymore, but ... it made me feel MUCH better about not staying around...
Money doesn't bring true happiness, after all.....