It also depends what you mean by rich - I'll assume you mean monetarily.

I know several who have inherited great wealth - so I won't count them.

1) One guy I know very well left school at 16 and became a carpenter. He bought a run down house and did it up on evenings and weekends - sold for a profit, bought a bigger house, did it up on the side etc. He later partnered with his friend who was an estate agent and they worked very successfully buying, doing up, and selling properties together. Net worth around £5 million. He's still working.

2) Another guy, a friend of my Dad's, bummed around after leaving school at 14, worked as a tram driver and taught himself plumbing on the side, basically worked 7 days a week. Then got a job at Heathrow loading bags on planes. He worked every shift he could and continued plumbing on the side. Bought a run down house, filled it with lodgers (mostly Irish navvies). Bought another run down house, filled it with lodgers. etc. Grafted like this into his 70s. Now retired. Net worth around £10 million.

3) Another guy I know was especially bright. Did a degree in Economics and German. Became an accountant. After a period doing auditing he moved into small company analysis, specializing in small German companies. Twenty years ago his bonus alone was more than a million a year. He bought a million+ pound house without a mortgage - then bought one that was probably three times the size of that. In the end he cut back on work, and now only works from home, and only does work that interests him. He pays his daughter to pretend to be him on Skype, so he can go off and play golf. Net worth, around £20+ million.

Couple of interesting points - the first guy never got married, never had kids, never really had a serious girlfriend for more than a few months - and is not particularly happy. Second guy was completely obsessive about not spending money, he drove around in a clapped out van, which he fixed himself, and never really enjoyed his money. Third guy was a real family man and met his wife (who is gorgeous) when he was a student with no money, and she was a nurse (with probably even less money!). All their happiness comes from each other and their three beautiful kids. But yes, they do live in a big house - but I suspect they would have been just as happy in a semi.

Funnily enough, none of the software engineers I know are particularly well off (financially)!

Outside of that, I know a few VC's and a few founders who have had successful exits. Of the ones who fall in the "founder" camp, I think they've all gone on to founding new companies since their exits. The VC guys are all still VC's as far as I know, although I haven't talked to most of those guys in a while.